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

Abstract

The invention relates to an organic compound, a mixture, a composition, a light-emitting device and a display panel, the chemical structural formula of the organic compound is as shown in a formula I, and Ar in the formula I is selected from a group as shown in a formula II: # imgabs0 #. The organic compound provided by the invention has high fluorescence quantum efficiency and enough high stability; when the organic compound is used as a luminescent material, the problems of aggregation quenching, light color shift, low quantum efficiency and the like can be solved, so that the luminous efficiency of a luminescent device can be effectively improved, and the service life of the luminescent device can be effectively prolonged.

Description

Technical Field

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

[0002] At present, organic electroluminescent elements generally include an anode, a cathode, and an organic functional layer located between the two, and use the organic material of the organic layer to convert electrical energy into light energy, thereby realizing organic electroluminescence. In order to improve the luminous efficiency and service life of organic electroluminescent devices, the organic functional layer often includes a multilayer structure, and the organic matter of each layer is different. Specifically, the organic functional layer generally includes but is not limited to a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. When the organic electroluminescent device is working, by applying voltage to the anode and the cathode, holes are injected from the anode to the organic layer, and electrons are injected from the cathode to the organic layer. The injected holes meet with the electrons to form excitons, and the excitons emit light when they return to the ground state through radiation transition, thereby realizing the luminescence of the organic electroluminescent device. With the characteristics of self-luminescence, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast, and high response, organic electroluminescent devices have broad application prospects and broad development potential.

[0003] In order to improve the luminous efficiency of organic electroluminescent devices, the industry has developed a variety of luminescent material systems based on fluorescence and phosphorescence. At present, for the blue light band with higher energy, the reliability of organic electroluminescent devices using blue light fluorescent materials is relatively higher, and at the same time, it can avoid the environmental pollution caused by the introduction of heavy metals (such as iridium and platinum), thereby effectively reducing costs. However, the development of blue light fluorescent materials with excellent photoelectric properties faces a huge challenge, and its performance indicators such as luminescent quantum efficiency, color purity and stability need to be improved. How to design new blue light fluorescent materials with better performance to improve the efficiency and life of light-emitting devices has always been a problem that needs to be solved urgently by those skilled in the art. Summary of the invention

[0004] The embodiments of the present application provide an organic compound, a mixture, a composition, a light-emitting device and a display panel. The organic compound has high fluorescence quantum efficiency and sufficiently high stability. When the organic compound is used as a light-emitting material, it can solve problems such as aggregation quenching, light color shift and low quantum efficiency, and can effectively improve the luminous efficiency and service life of the light-emitting device.

[0005] In order to achieve the above object, according to the first aspect of the present application, an organic compound is provided, and the chemical structural formula of the organic compound is shown in Formula I:

[0006]

[0007] Wherein, Ar is selected from the group shown in formula II;

[0008] Y is selected from -O-, -S- and -NR 6 Any one of -;

[0009] R 1 , R 4 and R 5 Selected from hydrogen, deuterium, straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, branched-chain alkyl groups having 3 to 20 carbon atoms, cyclic alkyl groups having 3 to 20 carbon atoms, branched-chain alkoxy groups having 3 to 20 carbon atoms, cyclic alkoxy groups having 3 to 20 carbon atoms, silyl groups, -CN, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0010] R 2 and R 3 is selected from hydrogen, deuterium, a linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a silyl group, -CN, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms, -NR 7 R 8 ;

[0011] R 6 , R 7 and R 8 Selected from a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0012] n1 and n5 are selected from any integer from 0 to 4; n2 is selected from any integer from 0 to 5; n3 and n4 are selected from any integer from 0 to 3;

[0013] * indicates the attachment site.

[0014] According to the second aspect of the present application, a mixture is provided, which contains at least one organic functional material and at least one organic compound as described above, and the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron injection materials, electron transport materials, luminescence auxiliary materials, hole blocking materials, organic light-emitting guest materials, organic host materials and organic dyes.

[0015] According to the third aspect of the present application, a composition is also provided, which comprises at least one organic solvent and at least one of the organic compounds mentioned above, or the composition comprises at least one of the organic solvents and at least one of the mixtures mentioned above.

[0016] According to the fourth aspect of the present application, a light-emitting device is also provided, which includes a first electrode, a second electrode and an organic functional layer located between the first electrode and the second electrode, the material of the organic functional layer includes at least one of the organic compounds described in any one of the above items, or the material of the organic functional layer includes the mixture described above, or the organic functional layer is made of the composition described above.

[0017] According to a fifth aspect of the present application, a display panel is also provided, comprising the light-emitting device described above.

[0018] In the organic compounds, mixtures, compositions, light-emitting devices and display panels of the embodiments of the present application, the main skeleton of the organic compound represented by Formula I is composed of an electron-deficient boron (B) atom, an electron-rich nitrogen (N) atom and a benzene ring arranged together, and the main skeleton cooperates with the heteroatom condensed ring to form a rigid conjugated planar skeleton with a multiple resonance effect, so that the organic compound has a high fluorescence quantum efficiency and sufficiently high stability. At the same time, the organic compound represented by Formula I has flexible modifiability and can be modified at different sites on the periphery of the skeleton (for example, R 1 , R 2 , R 3 , R 4 and R 5 The site where the group is replaced) introduces an inert or electron-donating / accepting substituent (e.g., R 1 , R 2 , R 3 , R 4 and R 5 Group), thereby providing important steric hindrance or charge transfer characteristics. When the organic compound is used as a luminescent material (e.g., a blue fluorescent doping material), it can solve the problems of aggregation quenching, light color shift, and low quantum efficiency. Therefore, when the organic compound represented by Formula I is applied to the light-emitting layer of a light-emitting device, the luminous efficiency and service life of the light-emitting device can be effectively improved, thereby achieving high luminous efficiency and high device life.

[0019] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] 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 figure numbers represent the same parts in the following description.

[0021] Figure 1 It is a schematic diagram of the structure of a light-emitting device provided in an embodiment of the present application.

[0022] Figure numerals: 1, substrate; 11, first electrode layer (anode); 12, hole injection layer; 13, hole transport layer; 14, light-emitting layer; 15, electron transport layer; 16, electron injection layer; 17, second electrode layer (cathode). DETAILED DESCRIPTION

[0023] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments in the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention. In addition, it should be understood that the specific implementation methods described herein are only used to illustrate and explain the present invention, and are not used to limit the present invention. In the present invention, unless otherwise specified, the directional words used, such as "upper" and "lower", generally refer to the upper and lower parts of the device in actual use or working state, specifically the drawing direction in the accompanying drawings; while "inside" and "outside" refer to the outline of the device. In the present invention, "optionally", "optional", and "optional" refer to optional, that is, to select any one of the two parallel schemes of "yes" or "no". If multiple "options" appear in a technical solution, if there is no special explanation, and there is no contradiction or mutual restriction, each "optional" is independent of each other. In the present invention, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0024] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0025] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0026] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0027] In the present application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0028] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano, isocyano, nitro, halogen, alkyl containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silane, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, , cyano, isocyano, nitro, halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from but not limited to: deuterium atom, cyano, isocyano, nitro, halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups can also be further substituted by substituents acceptable in the art.

[0029] In the present application, "ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) obtained by atoms bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0030] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For a polycyclic ring, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic group having 6 to 40 ring atoms" refers to an aromatic group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and the aromatic group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, fluorenyl, dinaphthylenyl, acenaphthene and its derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), such as acenaphthene, fluorene, or 9,9'-diarylfluorene, triarylamine, diaryl ether system should also be included in the definition of aromatic group.

[0031] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, Pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothienyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0032] In the present application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 2-Hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-tridecyl, 2-tetradecyl, 2-pentadecyl, 2-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-octadecyl, 2-octadecyl, 2-nonadecyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, 2-heneicosyl, 2-heneicosyl, 2-heconicosyl, 2-docosyl, 2-tricosyl, 2-tetracosyl, 2-pentacosyl, 2-hexacosyl, 2-heptacosyl, 2-octacosyl, 2-nonacosyl, 2-triacontyl, etc.

[0033] In the present application, "amino" refers to an amine derivative having the structural characteristics of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amines include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0034] In the present application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (wherein Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0035] In the present application, the term "alkoxy" refers to a group having a structure of "-O-alkyl", i.e., an alkyl group as defined above is connected to other groups via an oxygen atom. Phrases containing the term, suitable examples include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-OC(CH3)3 or -OtBu).

[0036] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0037] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as a linking site.

[0038] In the present application, when the fusion site is not specified in the group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the ortho position in the group are fusion sites.

[0039] In the present application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0040] 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 which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0041] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0042] The present application provides an organic compound, the chemical structure of which is shown in Formula I:

[0043]

[0044] Wherein, Ar is selected from the group shown in formula II;

[0045] Y is selected from -O-, -S- and -NR 6 Any one of -;

[0046] R 1 , R 4 and R 5Selected from hydrogen, deuterium, straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, branched-chain alkyl groups having 3 to 20 carbon atoms, cyclic alkyl groups having 3 to 20 carbon atoms, branched-chain alkoxy groups having 3 to 20 carbon atoms, cyclic alkoxy groups having 3 to 20 carbon atoms, silyl groups, -CN, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0047] R 2 and R 3 is selected from hydrogen, deuterium, a linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a silyl group, -CN, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms, -NR 7 R 8 ;

[0048] R 6 , R 7 and R 8 Selected from a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0049] n1 and n5 are selected from any integer from 0 to 4; n2 is selected from any integer from 0 to 5; n3 and n4 are selected from any integer from 0 to 3;

[0050] * indicates the attachment site.

[0051] In the embodiment of the present application, the main skeleton of the organic compound represented by Formula I is composed of an electron-deficient boron (B) atom, an electron-rich nitrogen (N) atom and a benzene ring, and the main skeleton cooperates with the heteroatom condensed ring to form a rigid conjugated planar skeleton with a multiple resonance effect, so that the organic compound has a high fluorescence quantum efficiency and sufficiently high stability. At the same time, the organic compound represented by Formula I has flexible modifiability and can be modified at different positions on the periphery of the skeleton (for example, R 1 , R 2 , R 3 , R 4 and R 5The site where the group is replaced) introduces an inert or electron-donating / accepting substituent (e.g., R 1 , R 2 , R 3 , R 4 and R 5 Group), thereby providing important steric hindrance or charge transfer characteristics. When the organic compound is used as a luminescent material (e.g., a blue fluorescent doping material), it can solve the problems of aggregation quenching, light color shift, and low quantum efficiency. Therefore, when the organic compound represented by Formula I is applied to the light-emitting layer of a light-emitting device, the luminous efficiency and service life of the light-emitting device can be effectively improved, thereby achieving high luminous efficiency and high device life.

[0052] It should be noted that in the organic compound represented by Formula I, the Ar group and R 3 The group is combined with the rigid conjugated plane skeleton described above to ensure the conjugated size and excited state energy level of the condensed ring molecule, and to ensure that the light color does not shift. Moreover, the synthesis process of the above-mentioned organic compound obtained is simple, low cost, and highly modifiable. In addition, the organic compound represented by Formula I can provide a steric group, an electron donor / acceptor group, which is conducive to changing the photoelectric properties of the molecule, thereby improving the key characteristics such as quantum efficiency and spectral half-peak width. Therefore, the organic compound provided by the embodiment of the present application is very suitable for being applied to organic electronic devices as a luminescent material.

[0053] In some embodiments, the organic compound is selected from any one of the compounds represented by Formula I-1 and Formula I-2:

[0054]

[0055] In some embodiments, R 1 Selected from tert-butyl or phenyl.

[0056] In some embodiments, R 4 and R 5 Any one selected from hydrogen, deuterium, methyl, tert-butyl and phenyl.

[0057] In some embodiments, the organic compound is selected from any one of the following compounds:

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066] It can be understood that the organic compounds represented by Formula I provided in the embodiments of the present application are not limited to the structures listed above, and these structures can be arbitrarily substituted.

[0067] The aromatic amine organic compound shown in Formula I provided in the embodiment of the present application can be used as an organic functional material in the organic functional layer of an electronic device. The organic functional layer includes but is not limited to a hole injection layer (HIL), a hole transport layer (HTL), an electron injection layer (EIL), an electron transport layer (ETL), a prime layer, a hole blocking layer (HBL) and an emission material layer (EML).

[0068] In some embodiments, the organic compound described in the embodiments of the present application is used in a light-emitting layer of an electronic device.

[0069] In a specific embodiment, the material of the light-emitting layer includes a main material and a doping material, and the doping material includes at least one organic compound represented by Formula I.

[0070] In a specific embodiment, the doping material is a blue light fluorescent doping material, that is, the above-mentioned light-emitting layer emits blue light. Of course, in other embodiments, the organic compound can also be used in a light-emitting layer that emits sky blue light or green light and serve as a doping material for the light-emitting layer.

[0071] It can be understood that the organic compounds provided in the embodiments of the present application are not limited to blue light doping materials.

[0072] An embodiment of the present application also provides a polymer, wherein the monomer of the polymer includes an organic compound shown in Formula I.

[0073] The present application also provides a mixture, which contains at least one organic compound as described above and at least one organic functional material. The organic functional material is selected from at least one of hole injection materials, hole transport materials, electron injection materials, electron transport materials, luminescence auxiliary materials, hole blocking materials, luminescent materials, organic luminescent guest materials, organic host materials and organic dyes.

[0074] The present application also provides a composition, comprising at least one first organic solvent and at least one organic compound as described above, or comprising at least one first organic solvent and at least one mixture as described above. The first organic solvent is selected from at least one of aromatic, heteroaromatic, ester, aromatic ketone, aromatic ether, aliphatic ketone, aliphatic ether, alicyclic, olefinic, boric acid ester or phosphate compounds.

[0075] In some embodiments, the first organic solvent is selected from aromatic or heteroaromatic based solvents.

[0076] In some embodiments, examples of aromatic or heteroaromatic solvents suitable for the present application include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbenzene, butylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, 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, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0077] In some embodiments, examples of aromatic ketone-based solvents suitable for the present application include, but are not limited to: 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.

[0078] In some embodiments, examples of aromatic ether-based solvents suitable for the present application include, but are not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0079] In some embodiments, examples of aliphatic ketone-based solvents suitable for the present application include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, 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.

[0080] In some embodiments, examples of ester-based solvents suitable for the present application include, but are not limited to: 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, and isononyl isononanoate are particularly preferred.

[0081] In some embodiments, the composition further comprises a second organic solvent, and the second organic solvent is selected from at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, and indene.

[0082] In some embodiments, solvents particularly suitable for the present application are solvents having a Hansen solubility parameter within the following ranges:

[0083] δd (dispersion force) is between 17.0 and 23.2 MPa 1 / 2 range, especially in the range of 18.5~21.0MPa1 / 2 scope;

[0084] δp (polar force) 0.2~12.5MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 scope;

[0085] δh (hydrogen bond force) is between 0.9 and 14.2 MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range.

[0086] The boiling point parameter of the organic solvent in the composition should be considered when selecting. In the embodiment of the present application, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; more preferably ≥250°C; and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head. The organic solvent can evaporate from the solvent system to form a film containing a functional material.

[0087] In some embodiments, the composition is a solution.

[0088] In some embodiments, the composition is a suspension.

[0089] In some embodiments, the content of the organic compound or the mixture in the composition ranges from 0.01wt% to 20wt%. Further, the content of the organic compound or the mixture in the composition ranges from 0.1wt% to 15wt%. Preferably, the content of the organic compound or the mixture in the composition ranges from 0.2wt% to 10wt%.

[0090] The present application also provides a use of the composition as a coating or printing ink in the preparation of an organic electronic device, and it is particularly preferred to prepare the organic electronic device by printing or coating.

[0091] In some embodiments, suitable printing or coating techniques include, but are not limited to, inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing, pad printing, slot extrusion coating, etc. Preferred are gravure printing, nozzle printing and inkjet printing. The solution or suspension may further include one or more components such as a surfactant, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, an adhesive, etc., for adjusting viscosity, film-forming properties, and improving adhesion, etc.

[0092] An embodiment of the present application further provides an organic electronic device, wherein the material of the organic electronic device comprises the above organic compound or the above mixture, or the organic electronic device is prepared from the above composition.

[0093] The organic electronic devices include, but are not limited to, organic light-emitting diodes (OLED), organic photovoltaic cells (OPV), organic light-emitting cells (OLEEC), organic field-effect transistors (OFET), organic light-emitting field-effect transistors (OLEFET), organic lasers, organic spin electronic devices, organic sensors and organic plasmon emitting diodes (OPED), etc. Preferably, the organic electronic device is an organic electroluminescent device, such as OLED, OLEEC or OLEFET.

[0094] In some embodiments, the organic electronic device is a light emitting device. Figure 1 As shown, the light-emitting device includes a first electrode 11, a second electrode 17, and an organic functional layer located between the first electrode 11 and the second electrode 17, wherein the material of the organic functional layer includes at least one of the organic compounds represented by the above formula I, or the material of the organic functional layer includes the mixture described above, or the organic functional layer is prepared using the organic compound, mixture or composition described above.

[0095] In one embodiment, the first electrode 11 is an anode, and the second electrode 17 is a cathode.

[0096] Specifically, the organic functional layer is selected from at least one of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a light-emitting auxiliary layer and an organic light-emitting layer. Preferably, the organic functional layer at least includes an organic light-emitting layer.

[0097] Specifically, the light emitting device further includes a substrate 1 , and the first electrode 11 is arranged on the substrate 1 .

[0098] In a specific embodiment, the organic functional layer includes a hole injection layer 12, a hole transport layer 13, a light-emitting layer 14, an electron transport layer 15 and an electron injection layer 16 stacked in sequence on the first electrode layer 11, wherein the material of the light-emitting layer 14 is selected from at least one organic compound represented by formula I.

[0099] In a specific embodiment, the material of the light-emitting layer 14 includes a host material and a doping material, and the doping material includes at least one of the organic compounds shown in Formula I.

[0100] In some embodiments, the organic compound can be applied to a light-emitting layer that emits blue light, sky blue light or green light, and can be used as a doping material for the light-emitting layer.

[0101] In some embodiments, the above-mentioned light emitting device (especially OLED) includes a substrate, an anode, at least one light emitting layer and a cathode. It can be understood that the substrate is equivalent to Figure 1 The substrate 1 shown, the anode is equivalent to Figure 1 The first electrode 11 shown, the light-emitting layer is equivalent to Figure 1 The light-emitting layer 14 shown, the cathode is equivalent to Figure 1 The second electrode 17 is shown.

[0102] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. The substrate preferably has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred example, the substrate is flexible and can be selected from a polymer film or plastic, and its glass transition temperature Tg is above 150°C, preferably above 200°C, more preferably above 250°C, and preferably above 300°C. Examples of suitable flexible substrates are poly(ethylene terephthalate) (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0103] The anode may include a conductive metal, a metal oxide, or a conductive polymer. The anode can easily inject holes into the HIL, HTL, or EML. In one example, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer or the p-type semiconductor material as the HIL, HTL, or EBL is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide, etc. Other suitable anode materials are known and can be easily selected for use by a person 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, etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare light-emitting devices according to embodiments of the present application.

[0104] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material as the EIL or ETL or HBL is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs may be used as cathode materials for the device of the present invention. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material 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, etc.

[0105] In a specific embodiment, the organic light-emitting layer of the light-emitting device is prepared by the above composition.

[0106] In some embodiments, the light emitting device provided in the embodiments of the present application has a light emitting wavelength ranging from 300 nanometers (nm) to 1000 nm.

[0107] In a specific embodiment, the light emitting device has a light emitting wavelength ranging from 350 nm to 900 nm.

[0108] In another specific embodiment, the light emitting device has a light emitting wavelength ranging from 400 nm to 800 nm.

[0109] The embodiments of the present application also provide an application of the above-mentioned organic electronic device in various electronic devices, and the electronic devices include but are not limited to display devices, lighting devices, light sources, sensors, etc.

[0110] An embodiment of the present application further provides an electronic device using the above-mentioned organic electronic device, and the electronic device includes but is not limited to a display device, a lighting device, a light source, a sensor, etc.

[0111] The present application will be described below in conjunction with preferred embodiments, but the present application is not limited to the embodiments described below. It should be understood that the attached claims summarize the scope of the present application. Under the guidance of the concept of the present invention, 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

[0113] The organic compound and its preparation method of the present application are further described in detail below in conjunction with specific examples. The raw materials used in the following examples are all commercially available products unless otherwise specified.

[0114] (I) Organic Compound Synthesis Example

[0115] Example 1

[0116] The synthetic route of organic compound P2-1 is as follows:

[0117]

[0118] Synthesis of intermediate P2-1-3:

[0119] Compound P2-1-1 (0.1 mol) and compound P2-1-2 (0.1 mol) were weighed and placed in a clean three-necked flask, and cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, and the nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 140° C. and refluxed for 4 hours (h) under a nitrogen atmosphere; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and spin-dried, and the intermediate P2-1-3 was obtained by column chromatography with a yield of 83%; the electrospray ionization mass spectrometry (ESI-MS) result of the intermediate P2-1-3 was: m / z [H + ]=463.

[0120] Synthesis of intermediate P2-1-5:

[0121] Compound P2-1-3 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (tri(dibenzylideneacetone)dipalladium, 1.0 mmol), TTBP (tri-tert-butylphosphine, 2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask, and the nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, the organic phase was dried and then spin-dried, and the intermediate P2-1-5 was obtained by column chromatography with a yield of 91%. The m / z [H + ]=719.

[0122] Synthesis of organic compound P2-1:

[0123] Weigh compound P2-1-5 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (boron tribromide, 40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the reaction solution was naturally cooled to room temperature, and then sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and then ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P2-1 with a yield of 14%. The m / z [H + ]=693.

[0124] Example 2

[0125] The synthetic route of organic compound P3-1 is as follows:

[0126]

[0127] Synthesis of intermediate P3-1-2:

[0128] Compound P2-1-1 (0.1 mol) and compound P3-1-1 (0.1 mol) were weighed and placed in a clean three-necked flask, and cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times, and the reaction solution was heated to 140° C. and refluxed for 4 hours under a nitrogen atmosphere; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate P3-1-2 was obtained by column chromatography with a yield of 66%. The m / z [H + ]=522.

[0129] Synthesis of intermediate P3-1-3:

[0130] Compound P3-1-2 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times, and the reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere; after the reaction solution was naturally cooled, the solution was washed with water and separated, the organic phase was dried and then spin-dried, and the intermediate P3-1-3 was obtained by column chromatography with a yield of 92%. The m / z [H + ]=779.

[0131] Synthesis of organic compound P3-1:

[0132] Weigh compound P3-1-3 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) n-hexane solution dropwise, raise the temperature to 60 ° C after natural temperature rise, and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally raise the temperature to room temperature, and continue to react for 0 .5h, then the reaction solution was cooled to 0°C, N,N-diisopropylethylamine (80mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120°C for 3h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and the crude product was obtained by column chromatography, and then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P3-1 with a yield of 15%. The m / z of the organic compound P3-1 [H + ]=752.

[0133] Example 3

[0134] The synthetic route of organic compound P1-3 is as follows:

[0135]

[0136] Synthesis of intermediate P1-3-3:

[0137] Compound P1-3-1 (0.1 mol) and compound P1-3-2 (0.1 mol) were weighed and placed in a clean three-necked flask, and cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times, and the reaction solution was heated to 140° C. and refluxed for 4 hours under a nitrogen atmosphere; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate P1-3-3 was obtained by column chromatography with a yield of 90%. The m / z [H + ]=523.

[0138] Synthesis of intermediate P1-3-4:

[0139] Compound P1-3-3 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask, Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, the reaction solution was heated to 100° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, the solution was washed with water and separated, the organic phase was dried and then spin-dried, and the intermediate P1-3-4 was obtained by column chromatography with a yield of 85%. The m / z [H + ]=779.

[0140] Synthesis of organic compounds P1-3:

[0141] Weigh compound P1-3-4 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, raise the temperature to 60 ° C after natural temperature rise, and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally raise the temperature to room temperature, and continue the reaction 0.5h, then the reaction solution was cooled to 0°C, N,N-diisopropylethylamine (80mmol) was added dropwise, the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120°C for 3h; after the reaction was completed, the mixture was naturally cooled to room temperature, sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, ethyl acetate was added to extract, the organic phases were combined, the organic phases were spin-dried, and a crude product was obtained by column chromatography, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P1-3 with a yield of 19%. The m / z [H + ]=753.

[0142] Example 4

[0143] The synthetic route of organic compound P1-5 is as follows:

[0144]

[0145] Synthesis of intermediate P1-5-2:

[0146] Compound P1-5-1 (0.1 mol) and compound P3-1-1 (0.1 mol) were weighed and placed in a clean three-necked flask, and cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times, and the reaction solution was heated to 140° C. under a nitrogen atmosphere for 6 hours; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate P1-5-2 was obtained by column chromatography with a yield of 82%. The m / z [H + ]=599.

[0147] Synthesis of intermediate P1-5-3:

[0148] Compound P1-5-2 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times, and the reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere; after the reaction solution was naturally cooled, the solution was washed with water and separated, the organic phase was dried and then spin-dried, and the intermediate P1-5-3 was obtained by column chromatography with a yield of 72%. The m / z [H + ]=856.

[0149] Synthesis of organic compound P1-5:

[0150] Weigh compound P1-5-3 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, raise the temperature to 60 ° C after natural temperature rise, and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally raise the temperature to room temperature, and continue to react for 0 .5h, then the reaction solution was cooled to 0°C, N,N-diisopropylethylamine (80mmol) was added dropwise, the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120°C for 3h; after the reaction was completed, the mixture was naturally cooled to room temperature, sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, ethyl acetate was added to extract, the organic phases were combined, the organic phases were spin-dried, and a crude product was obtained by column chromatography, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P1-5 with a yield of 15%. The m / z of the organic compound P1-5 [H + ]=829.

[0151] Example 5

[0152] The synthetic route of organic compound P2-13 is as follows:

[0153]

[0154]

[0155] Synthesis of intermediate P2-13-2:

[0156] Compound P2-13-1 (0.1 mol) and compound P2-1-2 (0.1 mol) were weighed and placed in a clean three-necked flask, and cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate P1-3-3 was obtained by column chromatography with a yield of 83%. The m / z [H + ]=497.

[0157] Synthesis of intermediate P2-13-3:

[0158] Compound P2-13-2 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate P2-13-3 was obtained by column chromatography with a yield of 90%. The m / z [H + ]=754.

[0159] Synthesis of intermediate P2-13-5:

[0160] Compound P2-13-3 (0.1 mol) and compound P2-13-4 (0.12 mol) were weighed and placed in a clean three-necked flask, and Pd(dppf)Cl2 ([1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, 2.0 mmol), potassium acetate (0.4 mol) and solvent 1,4-dioxane were added to the three-necked flask, and the nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere; after the reaction solution was naturally cooled, the solution was washed with water and separated, the organic phase was dried and then spin-dried, and the intermediate P2-13-5 was obtained by column chromatography with a yield of 82%. The m / z [H + ]=845.

[0161] Synthesis of intermediate P2-13-7:

[0162] Weigh compound P2-13-5 (60 mmol) and compound P2-13-6 (60 mmol) into a clean three-necked flask, and add Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium, 3.0 mmol) and potassium carbonate (0.24 mol) into the three-necked flask. The reactants are dissolved in 300 mL of toluene, 150 mL of ethanol and 150 mL of water. The nitrogen in the three-necked flask is replaced three times. The reaction solution is heated to 100 ° C. and refluxed for 12 h under a nitrogen atmosphere. After the reaction solution is cooled naturally, the separated liquid is washed with water, the organic phase is dried and then spin-dried, and the intermediate P2-13-7 is obtained by column chromatography with a yield of 76%. The m / z [H + ]=1073.

[0163] Synthesis of organic compound P2-13:

[0164] Weigh compound P2-13-7 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, raise the temperature to 60 ° C after natural temperature rise, and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally raise the temperature to room temperature, and continue to react for 0 .5h, then the reaction solution was cooled to 0°C, N,N-diisopropylethylamine (80mmol) was added dropwise, the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120°C for 3h; after the reaction was completed, the mixture was naturally cooled to room temperature, sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, ethyl acetate was added to extract, the organic phases were combined, the organic phases were spin-dried, and a crude product was obtained by column chromatography, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P2-13 with a yield of 10%. The m / z of the organic compound P2-13 [H + ]=1046.

[0165] Example 6

[0166] The synthetic route of organic compound P1-18 is as follows:

[0167]

[0168] Synthesis of intermediate P1-18-1:

[0169] Compound P2-1-1 (0.1 mol) and compound P1-3-2 (0.1 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate P1-18-1 was obtained by column chromatography with a yield of 89%. The m / z [H + ]=447.

[0170] Synthesis of intermediate P1-18-3:

[0171] Compound P1-18-1 (0.1 mol) and compound P1-18-2 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 16 h under a nitrogen atmosphere. After the reactant was cooled naturally, the liquid was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate P1-18-3 was obtained by column chromatography with a yield of 59%. The m / z [H + ]=779.

[0172] Synthesis of organic compound P1-18:

[0173] Compound P1-18-3 (20 mmol) was weighed and placed in a clean three-necked flask, 200 mL of dry tert-butylbenzene was added, and the nitrogen in the three-necked flask was replaced three times. The reaction solution was cooled to -30 ° C. under a nitrogen atmosphere; tert-butyl lithium (40 mmol) n-hexane solution was added dropwise, and the temperature was raised to 60 ° C. after natural temperature rise, and the reaction was continued for 2 h, and then the n-hexane solvent was removed by vacuum rotary evaporation; the reaction solution was cooled to -30 ° C. again, BBr3 (40 mmol) was added, and the temperature was raised to room temperature naturally after continuous stirring, and the reaction was continued for 0.5 h, then the reaction solution was cooled to 0°C, N,N-diisopropylethylamine (80 mmol) was added dropwise, the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120°C for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, ethyl acetate was added to extract, the organic phases were combined, the organic phases were spin-dried, and a crude product was obtained by column chromatography, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P1-18 with a yield of 14%. The m / z of the organic compound P1-18 [H + ]=753.

[0174] Example 7

[0175] The synthetic route of organic compound P3-18 is as follows:

[0176]

[0177] The synthesis of intermediate P3-1-2 is referred to Example 2 and will not be described in detail here.

[0178] Synthesis of intermediate P3-18-1:

[0179] Compound P3-1-2 (0.1 mol) and compound P1-18-2 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 16 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate P3-18-1 was obtained by column chromatography with a yield of 53%. The m / z [H + ]=855.

[0180] Synthesis of organic compound P3-18:

[0181] Weigh compound P3-18-1 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then heated to 120 ° C. for reaction for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P3-18 with a yield of 12%. The m / z [H + ]=828.

[0182] Example 8

[0183] The synthetic route of organic compound P2-21 is as follows:

[0184]

[0185] Synthesis of intermediate P2-21-1:

[0186] Compound P1-3-1 (0.1 mol) and compound P2-1-2 (0.1 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. and refluxed for 4 h under a nitrogen atmosphere; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate P2-21-1 was obtained by column chromatography with a yield of 88%. The m / z [H + ]=539.

[0187] Synthesis of intermediate P2-21-3:

[0188] Compound P2-21-1 (0.1 mol) and compound P2-21-2 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate P2-21-3 was obtained by column chromatography with a yield of 81%. The m / z [H + ]=832.

[0189] Synthesis of organic compound P2-21:

[0190] Weigh compound P2-21-3 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, raise the temperature to 60 ° C after natural temperature rise, and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally raise the temperature to room temperature, and continue the reaction 0.5h, then the reaction solution was cooled to 0°C, N,N-diisopropylethylamine (80mmol) was added dropwise, the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120°C for 3h; after the reaction was completed, the mixture was naturally cooled to room temperature, sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, ethyl acetate was added to extract, the organic phases were combined, the organic phases were spin-dried, and a crude product was obtained by column chromatography, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P2-21 with a yield of 10%. The m / z [H + ]=805.

[0191] Example 9

[0192] The synthetic route of organic compound P2-26 is as follows:

[0193]

[0194] The synthesis of intermediates P2-13-2, P2-13-3 and P2-13-5 is referred to Example 5 and will not be repeated here.

[0195] Synthesis of intermediate P2-26-2:

[0196] Weigh compound P2-13-5 (60 mmol) and compound P2-26-1 (60 mmol) and place them in a clean three-necked flask, add Pd(PPh3)4 (3.0 mmol) and potassium carbonate (0.24 mol) into the three-necked flask, and dissolve the reactants in 300 mL of toluene, 150 mL of ethanol and 150 mL of water. Replace nitrogen in the three-necked flask three times, and heat the reaction solution to 100 ° C under a nitrogen atmosphere and reflux for 12 h; wash the separated liquid with water after natural cooling, dry the organic phase and spin dry it, and obtain the intermediate P2-26-2 by column chromatography with a yield of 79%. The m / z [H + ]=962.

[0197] Synthesis of organic compound P2-26:

[0198] Weigh compound P2-26-2 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P2-26 with a yield of 11%. The m / z [H + ]=935.

[0199] Example 10

[0200] The synthetic route of organic compound P1-30 is as follows:

[0201]

[0202] Synthesis of intermediate P1-30-1:

[0203] Compound P2-13-1 (0.1 mol) and compound P1-3-2 (0.1 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate P1-30-1 was obtained by column chromatography with a yield of 83%. The m / z [H + ]=481.

[0204] Synthesis of intermediate P1-30-2:

[0205] Compound P1-30-1 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask, Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere; after the reaction solution was naturally cooled, the solution was washed with water and separated, the organic phase was dried and then spin-dried, and the intermediate P1-30-2 was obtained by column chromatography with a yield of 85%. The m / z [H + ]=738.

[0206] Synthesis of intermediate P1-30-4:

[0207] Compound P1-30-2 (0.1 mol) and compound P1-30-3 (0.11 mol) were weighed and placed in a clean three-necked flask. Pd132 (di-tert-butyldichloro-(4-dimethylaminophenyl)phosphine palladium (II), 3.0 mmol), X-Phos (6.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 110° C. and refluxed for 3 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, the separated liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate P1-30-4 was obtained by column chromatography with a yield of 93%. The m / z [H + ]=983.

[0208] Synthesis of organic compound P1-30:

[0209] Weigh compound P1-30-4 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was carried out for 0.5 h, and then the reaction solution was cooled to 0°C, N,N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120°C for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and subjected to column chromatography to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P1-30 with a yield of 8%. The m / z [H + ]=956.

[0210] Embodiment 11

[0211] The synthetic route of organic compound P2-35 is as follows:

[0212]

[0213]

[0214] The synthesis of intermediate P2-21-1 is referred to Example 8 and will not be described in detail here.

[0215] Synthesis of intermediate P2-35-2:

[0216] Compound P2-21-1 (0.1 mol) and compound P2-35-1 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 4 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate P2-35-2 was obtained by column chromatography with a yield of 88%. The m / z [H + ]=851.

[0217] Synthesis of intermediate P2-35-4:

[0218] Compound P2-35-2 (0.1 mol) and compound P2-35-3 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, the solution was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate P2-35-4 was obtained by column chromatography with a yield of 82%. The m / z [H + ]=1039.

[0219] Synthesis of organic compound P2-35:

[0220] Weigh compound P2-35-4 (20 mmol) and place it in a clean three-necked flask. Add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was carried out for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P2-35 with a yield of 14%. The m / z [H + ]=1012.

[0221] Example 12

[0222] The synthetic route of organic compound P1-56 is as follows:

[0223]

[0224] The synthesis of intermediate P1-3-3 is referred to Example 3 and will not be described in detail here.

[0225] Synthesis of intermediate P1-56-2:

[0226] Compound P1-3-3 (0.1 mol) and compound P1-56-1 (0.1 mol) were weighed and placed in a clean three-necked flask, Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 100° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the water was washed and the liquid was separated, the organic phase was dried and then spin-dried, and the intermediate P1-56-2 was obtained by column chromatography with a yield of 81%. The m / z [H + ]=667.

[0227] Synthesis of intermediate P1-56-4:

[0228] Compound P1-56-2 (0.1 mol) and compound P1-56-3 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate P1-56-4 was obtained by column chromatography with a yield of 85%. The m / z [H + ]=876.

[0229] Synthesis of organic compound P1-56:

[0230] Weigh compound P1-56-4 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, raise the temperature of the reaction solution to 60 ° C after natural temperature rise, and continue to react for 2 hours, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally raise the temperature to room temperature, and continue the reaction 0.5h, then the reaction solution was cooled to 0°C, N,N-diisopropylethylamine (80mmol) was added dropwise, the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120°C for 3h; after the reaction was completed, the mixture was naturally cooled to room temperature, sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, ethyl acetate was added to extract, the organic phases were combined, the organic phases were spin-dried, and the crude product was obtained by column chromatography, which was then recrystallized three times using toluene and ethyl acetate to obtain organic compound P1-56 with a yield of 13%. The m / z [H + ]=849.

[0231] Example 13

[0232] The synthetic route of organic compound P2-62 is as follows:

[0233]

[0234] The synthesis of intermediate P2-13-2 is referred to Example 5 and will not be described in detail.

[0235] Synthesis of intermediate P2-62-2:

[0236] Compound P2-13-2 (0.1 mol) and compound P2-62-1 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate P2-62-2 was obtained by column chromatography with a yield of 88%. The m / z [H + ]=774.

[0237] Synthesis of intermediate P2-62-3:

[0238] Compound P2-62-2 (0.1 mol) and compound P1-30-3 (0.11 mol) were weighed and placed in a clean three-necked flask, Pd132 (3.0 mmol), X-Phos (6.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 110° C. and refluxed for 3 h under a nitrogen atmosphere; after the reaction solution was cooled naturally, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate P2-62-3 was obtained by column chromatography with a yield of 93%. The m / z [H + ]=1019.

[0239] Synthesis of organic compound P2-62:

[0240] Weigh compound P2-62-3 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P2-62 with a yield of 11%. The m / z [H + ]=992.

[0241] Embodiment 14

[0242] The synthetic route of organic compound P3-71 is as follows:

[0243]

[0244] Synthesis of intermediate P3-71-2:

[0245] Compound P2-1-1 (0.1 mol) and compound P3-71-1 (0.12 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.4 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 12 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate P3-71-2 was obtained by column chromatography with a yield of 62%. The m / z [H + ]=634.

[0246] Synthesis of intermediate P3-71-3:

[0247] Compound P3-71-2 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask, Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere; after the reaction solution was naturally cooled, the solution was washed with water and separated, the organic phase was dried and then spin-dried, and the intermediate P3-71-3 was obtained by column chromatography with a yield of 80%. The m / z [H + ]=891.

[0248] Synthesis of organic compound P3-71:

[0249] Weigh compound P3-71-3 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was carried out for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound P3-71 with a yield of 14%. The m / z [H + ]=864.

[0250] Embodiment 15

[0251] The synthetic route of organic compound Q1-1 is as follows:

[0252]

[0253] Synthesis of intermediate Q1-1-2:

[0254] Compound P2-1-1 (0.1 mol) and compound Q1-1-1 (0.1 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate Q1-1-2 was obtained by column chromatography with a yield of 94%. The m / z [H + ]=447.

[0255] Synthesis of intermediate Q1-1-3:

[0256] Compound Q1-1-2 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q1-1-3 was obtained by column chromatography with a yield of 89%. The m / z [H + ]=703.

[0257] Synthesis of organic compound Q1-1:

[0258] Weigh compound Q1-1-3 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, raise the temperature to 60 ° C after natural temperature rise, and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally raise the temperature to room temperature, and continue the reaction 0.5h, then the reaction solution was cooled to 0°C, N,N-diisopropylethylamine (80mmol) was added dropwise, the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120°C for 3h; after the reaction was completed, the mixture was naturally cooled to room temperature, sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, ethyl acetate was added to extract, the organic phases were combined, the organic phases were spin-dried, and a crude product was obtained by column chromatography, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound Q1-1 with a yield of 22%. The m / z [H + ]=677.

[0259] Example 16

[0260] The synthetic route of organic compound Q2-6 is as follows:

[0261]

[0262] Synthesis of intermediate Q2-6-3:

[0263] Compound Q2-6-1 (0.1 mol) and compound Q2-6-2 (0.1 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate Q2-6-3 was obtained by column chromatography with a yield of 88%. The m / z [H + ]=615.

[0264] Synthesis of intermediate Q2-6-4:

[0265] Compound Q2-6-3 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q2-6-4 was obtained by column chromatography with a yield of 78%. The m / z [H + ]=872.

[0266] Synthesis of organic compound Q2-6:

[0267] Weigh compound Q2-6-4 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then heated to 120 ° C. for reaction for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound Q2-6 with a yield of 15%. The m / z [H + ]=845.

[0268] Embodiment 17

[0269] The synthetic route of organic compound Q3-12 is as follows:

[0270]

[0271] Synthesis of intermediate Q3-12-3:

[0272] Compound Q3-12-1 (0.1 mol) and compound Q3-12-2 (0.1 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate Q3-12-3 was obtained by column chromatography with a yield of 78%. The m / z [H + ]=724.

[0273] Synthesis of intermediate Q3-12-4:

[0274] Compound Q3-12-3 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q3-12-4 was obtained by column chromatography with a yield of 83%. The m / z [H + ]=981.

[0275] Synthesis of organic compound Q3-12:

[0276] Weigh compound Q3-12-4 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then heated to 120 ° C. for reaction for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound Q3-12 with a yield of 11%. The m / z [H + ]=954.

[0277] Embodiment 18

[0278] The synthetic route of organic compound Q2-14 is as follows:

[0279]

[0280] Synthesis of intermediate Q2-14-1:

[0281] Compound P2-13-1 (0.1 mol) and compound Q2-6-2 (0.1 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate Q2-14-1 was obtained by column chromatography with a yield of 89%. The m / z [H + ]=497.

[0282] Synthesis of intermediate Q2-14-2:

[0283] Compound Q2-14-1 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q2-14-2 was obtained by column chromatography with a yield of 81%. The m / z [H + ]=754.

[0284] Synthesis of intermediate Q2-14-3:

[0285] Compound Q2-14-2 (0.1 mol) and compound P2-13-4 (0.12 mol) were weighed and placed in a clean three-necked flask. Pd(dppf)Cl2 (2.0 mmol), potassium acetate (0.4 mol) and solvent 1,4-dioxane were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100°C and refluxed for 6 hours under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q2-14-3 was obtained by column chromatography with a yield of 88%. The m / z [H + ]=845.

[0286] Synthesis of intermediate Q2-14-5:

[0287] Weigh compound Q2-14-3 (60 mmol) and compound Q2-14-4 (60 mmol) and place them in a clean three-necked flask. Add Pd(PPh3)4 (3.0 mmol) and potassium carbonate (0.24 mol) to the three-necked flask, and dissolve the reactants in 300 mL of toluene, 150 mL of ethanol and 150 mL of water. Replace the nitrogen in the three-necked flask three times, and heat the reaction solution to 100 ° C under a nitrogen atmosphere and reflux for 12 hours; after the reaction solution is naturally cooled, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain the intermediate Q2-14-5 by column chromatography with a yield of 90%. The m / z [H + ]=961.

[0288] Synthesis of organic compound Q2-14:

[0289] Weigh compound Q2-14-5 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was carried out for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and the crude product was obtained by column chromatography, and then recrystallized three times using toluene and ethyl acetate to obtain an organic compound Q2-14 with a yield of 8%. The m / z [H + ]=934.

[0290] Embodiment 19

[0291] The synthetic route of organic compound Q2-16 is as follows:

[0292]

[0293] The synthesis of intermediates Q2-14-1, Q2-14-2 and Q2-14-3 refers to Example 18 and will not be repeated here.

[0294] Synthesis of intermediate Q2-16-2:

[0295] Weigh compound Q2-14-3 (60 mmol) and compound Q2-16-1 (60 mmol) and place them in a clean three-necked flask. Add Pd(PPh3)4 (3.0 mmol) and potassium carbonate (0.24 mol) to the three-necked flask. The reactants are dissolved in 300 mL of toluene, 150 mL of ethanol and 150 mL of water. Replace nitrogen in the three-necked flask three times. Heat the reaction solution to 100 ° C under a nitrogen atmosphere and reflux for 12 hours. After the reaction solution is cooled naturally, wash with water and separate the liquid. Dry the organic phase and spin dry it. Column chromatography is used to obtain the intermediate Q2-16-2 with a yield of 61%. The m / z [H + ]=978.

[0296] Synthesis of organic compound Q2-16:

[0297] Weigh compound Q2-16-2 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound Q2-16 with a yield of 11%. The m / z [H + ]=951.

[0298] Embodiment 20

[0299] The synthetic route of organic compound Q1-20 is as follows:

[0300]

[0301] The synthesis of intermediate Q1-1-2 refers to Example 15 and will not be described in detail here.

[0302] Synthesis of intermediate Q1-20-2:

[0303] Compound Q1-1-2 (0.1 mol) and compound Q1-20-1 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. The reaction solution was naturally cooled and then washed with water for separation. The organic phase was dried and then spin-dried. The intermediate Q1-20-2 was obtained by column chromatography with a yield of 83%. The m / z [H + ]=667.

[0304] Synthesis of intermediate Q1-20-3:

[0305] Compound Q1-20-2 (0.1 mol) and compound P2-35-3 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 8 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q1-20-3 was obtained by column chromatography with a yield of 85%. The m / z [H + ]=856.

[0306] Synthesis of organic compound Q1-20:

[0307] Weigh compound Q1-20-3 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was carried out for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound Q1-20 with a yield of 11%. The m / z [H + ]=829.

[0308] Embodiment 21

[0309] The synthetic route of organic compound Q3-27 is as follows:

[0310]

[0311] Synthesis of intermediate Q3-27-1:

[0312] Compound P2-13-1 (0.1 mol) and compound Q3-12-2 (0.1 mol) were weighed and placed in a clean three-necked flask. Cesium carbonate (0.2 mol) dissolved in N,N-dimethylformamide was added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 140° C. and refluxed for 4 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q3-27-1 was obtained by column chromatography with a yield of 89%. The m / z [H + ]=556.

[0313] Synthesis of intermediate Q3-27-2:

[0314] Compound Q3-27-1 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q3-27-2 was obtained by column chromatography with a yield of 86%. The m / z [H + ]=813.

[0315] Synthesis of intermediate Q3-27-3:

[0316] Compound Q3-27-2 (0.1 mol) and compound P2-13-4 (0.12 mol) were weighed and placed in a clean three-necked flask. Pd(dppf)Cl2 (2.0 mmol) and potassium acetate (0.4 mol) dissolved in 1,4-dioxane were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q3-27-3 was obtained by column chromatography with a yield of 83%. The m / z [H + ]=904.

[0317] Synthesis of intermediate Q3-27-5:

[0318] Weigh compound Q3-27-3 (60 mmol) and compound Q3-27-4 (60 mmol) and place them in a clean three-necked flask. Add Pd(PPh3)4 (3.0 mmol) and potassium carbonate (0.24 mol) to the three-necked flask and dissolve them in 300 mL of toluene, 150 mL of ethanol and 150 mL of water. Replace nitrogen in the three-necked flask three times. Heat the reaction solution to 100 ° C under nitrogen atmosphere and reflux for 12 h. After the reaction solution is cooled naturally, wash with water and separate the liquid. Dry the organic phase and spin dry it. Column chromatography to obtain intermediate Q3-27-5 with a yield of 76%. The m / z [H + ]=1037.

[0319] Synthesis of organic compound Q3-27:

[0320] Weigh compound Q3-27-5 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was carried out for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound Q3-27 with a yield of 14%. The m / z [H + ]=1010.

[0321] Embodiment 22

[0322] The synthetic route of organic compound Q3-30 is as follows:

[0323]

[0324]

[0325] The synthesis of intermediates Q3-27-1 and Q3-27-2 refers to Example 21 and will not be described in detail here.

[0326] Synthesis of intermediate Q3-30-1:

[0327] Compound Q3-27-2 (0.1 mol) and compound P1-30-3 (0.11 mol) were weighed and placed in a clean three-necked flask. Pd132 (3.0 mmol), X-Phos (6.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 110° C. and refluxed for 3 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q3-30-1 was obtained by column chromatography with a yield of 88%. The m / z [H + ]=1058.

[0328] Synthesis of organic compound Q3-30:

[0329] Weigh compound Q3-30-1 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30°C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60°C and continue to react for 2 hours, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30°C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound Q3-30 with a yield of 12%. The m / z [H + ]=1031.

[0330] Embodiment 23

[0331] The synthetic route of organic compound Q1-35 is as follows:

[0332]

[0333] Synthesis of intermediate Q1-35-1:

[0334] Compound P1-3-1 (0.1 mol) and compound Q1-1-1 (0.1 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate Q1-35-1 was obtained by column chromatography with a yield of 89%. The m / z [H + ]=523.

[0335] Synthesis of intermediate Q1-35-2:

[0336] Compound Q1-35-1 (0.1 mol) and compound P2-35-1 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 4 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q1-35-2 was obtained by column chromatography with a yield of 81%. The m / z [H + ]=835.

[0337] Synthesis of intermediate Q1-35-3:

[0338] Compound Q1-35-2 (0.1 mol) and compound P2-35-3 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q1-35-3 was obtained by column chromatography with a yield of 80%. The m / z [H + ]=1023.

[0339] Synthesis of organic compound Q1-35:

[0340] Weigh compound Q1-35-3 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 hours, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and continue The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain an organic compound Q1-35 with a yield of 11%. The m / z [H + ]=996.

[0341] Embodiment 24

[0342] The synthetic route of organic compound Q1-69 is as follows:

[0343]

[0344] Synthesis of intermediate Q1-69-2:

[0345] Compound P2-1-1 (0.1 mol) and compound Q1-69-1 (0.1 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate Q1-69-1 was obtained by column chromatography with a yield of 65%. The m / z [H + ]=523.

[0346] Synthesis of intermediate Q1-69-3:

[0347] Compound Q1-69-2 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), sodium tert-butoxide (0.2 mol) and solvent toluene were added to the three-necked flask. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q1-69-3 was obtained by column chromatography with a yield of 88%. The m / z [H + ]=779.

[0348] Synthesis of compound Q1-69:

[0349] Weigh compound Q1-69-3 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, and then continue The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was cooled to 120 ° C. and reacted for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain compound Q1-69 with a yield of 13%. The m / z [H + ]=753.

[0350] Embodiment 25

[0351] The synthetic route of organic compound Q2-72 is as follows:

[0352]

[0353] Synthesis of intermediate Q2-72-2:

[0354] Compound P2-1-1 (0.1 mol) and compound Q2-72-1 (0.1 mol) were weighed and placed in a clean three-necked flask, cesium carbonate (0.2 mol) and solvent N,N-dimethylformamide were added to the three-necked flask, nitrogen was replaced three times in the three-necked flask, and the reaction solution was heated to 140° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, the liquid was washed with water, the organic phase was dried and then spin-dried, and the intermediate Q2-72-2 was obtained by column chromatography with a yield of 90%. The m / z [H + ]=472.

[0355] Synthesis of intermediate Q2-72-3:

[0356] Compound Q2-72-2 (0.1 mol) and compound P2-1-4 (0.1 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1.0 mmol), TTBP (2.0 mmol), and sodium tert-butoxide (0.2 mol) were added to the three-necked flask and dissolved in toluene. The nitrogen in the three-necked flask was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere. After the reaction solution was cooled naturally, it was washed with water and separated. The organic phase was dried and then spin-dried. The intermediate Q2-72-3 was obtained by column chromatography with a yield of 93%. The m / z [H + ]=729.

[0357] Synthesis of compound Q2-72:

[0358] Weigh compound Q2-72-3 (20 mmol) and place it in a clean three-necked flask, add 200 mL of dry tert-butylbenzene to the three-necked flask, replace the nitrogen in the three-necked flask three times, and cool the reaction solution to -30 ° C under a nitrogen atmosphere; add tert-butyl lithium (40 mmol) in n-hexane solution dropwise, and after the reaction solution naturally heats up, raise the temperature to 60 ° C and continue to react for 2 h, then remove the n-hexane solvent by vacuum rotary evaporation; cool the reaction solution to -30 ° C again, add BBr3 (40 mmol), stir continuously and naturally heat to room temperature, The reaction was continued for 0.5 h, and then the reaction solution was cooled to 0 ° C., N, N-diisopropylethylamine (80 mmol) was added dropwise, and the mixture was stirred continuously and naturally heated to room temperature, and then the reaction solution was heated to 120 ° C. for 3 h; after the reaction was completed, the mixture was naturally cooled to room temperature, and sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction, and ethyl acetate was added to extract and the organic phases were combined. The organic phases were spin-dried and column chromatography was performed to obtain a crude product, which was then recrystallized three times using toluene and ethyl acetate to obtain compound Q2-72 with a yield of 24%. The m / z [H + ]=702.

[0359] Comparative Example

[0360] The present application also provides comparative examples 1 and 2. The organic compounds in comparative examples 1 and 2 are respectively recorded as "comparative compound Ref 1" and "comparative compound Ref 2", and their chemical structural formulas are as follows:

[0361]

[0362] (II) Energy level calculation of organic compounds

[0363] In the examples of the present application, the energy level of the organic compound plays a key role. The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, the first excited singlet state (S1) energy level, and the first excited triplet state (T1) energy level of the organic compounds obtained in Examples 1 to 25 of the present application and the comparative compounds Ref 1 and Ref 2 provided in the comparative examples can be obtained through theoretical calculations.

[0364] Specifically, the theoretical calculation part is mainly calculated by Gaussian 09W (Gaussian Inc.) software package, and the specific simulation method can be found in WO2011141110 or described in the following embodiments. It should be noted that the values ​​of HOMO, LUMO, S1, and T1 depend on the measurement method or calculation method used, and even for the same method, different evaluation methods, such as the starting point and peak value on the CV curve, can give different HOMO / LUMO values. Therefore, a reasonable and meaningful comparison should be carried out with the same measurement method and the same evaluation method. In the description of the embodiments of the present application, the ground state (S0) configuration is calculated according to the density functional theory (DFT) under the B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p) basis set, and the HOMO, LUMO, S1, and T1 values ​​of the material are calculated according to the optimized S0 structure using the time-dependent density functional theory (TD-DFT) under the B3PW91 / 6-31G(d) or B3PW91 / 6-31G(d,p) basis set, and the unit is Hartree.

[0365] The calculation results of the HOMO energy level, LUMO energy level and S1 energy level of the organic compounds obtained in Examples 1 to 25 of the present application and the comparative compounds Ref 1 and Ref 2 provided in the comparative examples are shown in Table 1.

[0366] Table 1

[0367]

[0368]

[0369] As can be seen from Table 1, the S1 energy levels of the organic compounds provided in Examples 1 to 25 of the present application are maintained at the same level as the S1 energy levels of the comparative compounds Ref 1 and Ref 2, indicating that the light colors of these organic compounds are similar; and the HOMO energy levels of the organic compounds provided in Examples 1 to 25 of the present application are all maintained at -4.9 to -5.2 eV, indicating that these organic compounds can be combined with other organic conjugated materials to form a good potential barrier for use in OLED devices.

[0370] (III) Preparation and characterization of OLED devices

[0371] by Figure 1 Taking the preparation of the OLED device shown in the figure as an example, the preparation method of the OLED device using the organic compound of the present application is described in detail below through specific embodiments.

[0372] In the following method for preparing an OLED device, ITO conductive glass is used as an anode substrate, PEDOT:PSS (poly(3,4-ethylenedioxythiophene)-poly(styrene sulfonic acid), CleviosTM) is used as a hole injection material, PVK (poly(9-vinylcarbazole), Sigma Aldrich, number average molecular weight 25,000-50,000) is used as a hole transport material, BH is used as a host material of the light-emitting layer, ET and 8-hydroxyquinoline lithium (Liq) are used as electron transport materials, Liq is used as an electron injection material, and Al is used as a cathode material. In addition, the organic compounds of the aforementioned synthetic examples are used as doping materials for the light-emitting layer to prepare the corresponding OLED devices.

[0373] Among them, the chemical structures of BH, ET and Liq are as follows:

[0374]

[0375] The preparation process of an OLED device using the above materials is described in detail below through specific examples.

[0376] Taking the method for preparing an OLED device using organic compound P2-1 as the doping material of the light-emitting layer as an example, the prepared OLED device is recorded as “OLED-1 device.” The method for preparing the OLED-1 device includes steps a to h.

[0377] Step a: ITO conductive glass substrate (equivalent to Figure 1 An ITO conductive glass substrate is provided, and the substrate is ultrasonically cleaned using one or more cleaning agents such as deionized water, acetone, isopropanol or chloroform to improve the work function of the anode 11.

[0378] Step b: spin-coating the hole injection material PEDOT:PSS on the anode 11, and then heat-treating it on a hot plate at 180°C for 10 minutes to obtain a hole injection layer 12 with a thickness of 20 nm.

[0379] Step c: Spin-coat a 5 mg / mL toluene solution of hole transport material PVK on the hole injection layer 12, and then heat-treat on a hot plate at 180°C for 60 min to obtain a hole transport layer 13 with a thickness of 40 nm.

[0380] Step d: Spin-coat the light-emitting layer 14 on the hole transport layer 13. Using BH as the main material and the organic compound P2-1 provided in Example 1 of the present application as the doping material, a 15 mg / mL methyl benzoate solution is prepared, wherein the mass ratio of BH to the organic compound P2-1 provided in Example 1 of the present application is 97:3, and after spin coating, heat treatment is performed on a heating plate at 140° C. for 10 minutes to obtain a light-emitting layer 14 with a thickness of 35 nm.

[0381] Step e: forming an electron transport layer 15 on the light emitting layer 14. In a vacuum chamber, the electron transport material ET and Liq are placed in different evaporation crucibles and placed in a high vacuum environment (1×10 -6 ET and Liq were co-deposited at a weight ratio of 5:5 under 300 mbar to form an electron transport layer 15 with a thickness of 30 nm on the light-emitting layer 14.

[0382] Step f: forming an electron injection layer 16 on the electron transport layer 15. The electron injection material Liq is evaporated on the electron transport layer 15 at an evaporation rate of to obtain an electron injection layer 16 with a thickness of 1 nm.

[0383] Step g: forming a cathode 17 on the electron injection layer 16. The cathode material Al is evaporated on the electron injection layer 16 at an evaporation rate to obtain a cathode 17 with a thickness of 100 nm.

[0384] Step h: placing the obtained device in a nitrogen atmosphere glove box and encapsulating it with a UV-curable resin to finally obtain an OLED-1 device.

[0385] The structure of the prepared OLED-1 device is: ITO / PEDOT:PSS (20 nm) / PVK (40 nm) / BH:organic compound P2-1 (3%, 35 nm) / ET:Liq (5:5, 30 nm) / Liq (1 nm) / Al (100 nm).

[0386] The preparation of OLED-2 to OLED-25 devices refers to the preparation method of device OLED-1, except that the organic compounds corresponding to sequence numbers 2 to 25 in Table 1 are used as doping materials for the light-emitting layer of the OLED device, and OLED-2 to OLED-25 devices are prepared accordingly. It can be understood that in the preparation methods of devices OLED-1 to OLED-25, except for the different doping materials for the light-emitting layer, other experimental conditions are the same.

[0387] Similarly, referring to the preparation method of OLED-1 device, comparative compounds Ref 1 and Ref 2 were used as doping materials of the light-emitting layer, respectively, to prepare comparative example OLED-Ref 1 and OLED-Ref 2 devices. Compared with the preparation method of OLED-1 device, the preparation methods of OLED-Ref 1 and OLED-Ref 2 devices are the same except that the doping materials of the light-emitting layer are different.

[0388] In the embodiments of the present application, the current-voltage (JV) characteristics of OLED-1 to OLED-25, OLED-Ref 1 and OLED-Ref 2 devices are characterized, and important parameters are recorded, including CIE color coordinates (x, y), luminous efficiency (CE, cd / A) and life (LT90, h). Among them, CE is the relative value obtained when the brightness is 1knits, and LT90 is the time taken for the brightness of the device to drop from the initial 1knits to 90% under constant current. The performance test was carried out in an environment with a temperature of 25°C and a humidity of 40%, and the performance test results are shown in Table 2.

[0389] Table 2

[0390]

[0391]

[0392] As can be seen from Table 2, the luminous efficiency and life of the devices OLED-1 to OLED-25 prepared by using the organic compound provided in the embodiment of the present application as the doping material of the light-emitting layer are higher than those of the devices OLED-Ref 1 and OLED-Ref 2, and the light colors of these OLED devices are similar. This is because the organic compound provided in the embodiment of the present application has the multiple resonance effect brought by the boron atoms and nitrogen atoms, so that the molecules maintain the local excitation characteristics, resulting in high luminous efficiency and deep blue emission. At the same time, the heteroatom fused ring structure in the organic compound brings a rigid molecular skeleton while maintaining a sufficiently high excited state energy level, so that the vibration relaxation is weakened, thereby enhancing the stability of the organic compound molecules. When the organic compound is applied to the light-emitting layer, it is beneficial to improve the service life of the light-emitting device. In summary, as a doping material for the light-emitting layer, the organic compound provided in the embodiment of the present application can more effectively improve the luminous efficiency and service life of the light-emitting device.

[0393] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0394] The above-described embodiments only express several implementation methods of the present application, which is convenient for understanding the technical solutions of the present invention in detail, but cannot be understood as limiting the scope of protection of the present application. It should be pointed out that, for those of ordinary skill in the art, without departing from the inventive concept of the present application, several variations and improvements can be made, which all belong to the scope of protection of the present application. It should be understood that the technical solutions obtained by those skilled in the art through logical analysis, reasoning or limited experiments on the basis of the technical solutions provided in the present application are all within the scope of protection of the claims attached to the present application. Therefore, the scope of protection of the present application shall be based on the contents of the attached claims, and the specification can be used to interpret the contents of the claims.

Claims

1. An organic compound, characterized in that The chemical structural formula of the organic compound is shown in Formula I: Wherein, Ar is selected from the group shown in formula II; Y is selected from -O-, -S- and -NR 6 Any one of -; R 1 , R 4 and R 5 Selected from hydrogen, deuterium, straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, branched-chain alkyl groups having 3 to 20 carbon atoms, cyclic alkyl groups having 3 to 20 carbon atoms, branched-chain alkoxy groups having 3 to 20 carbon atoms, cyclic alkoxy groups having 3 to 20 carbon atoms, silyl groups, -CN, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms; R 2 and R 3 is selected from hydrogen, deuterium, a linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a silyl group, -CN, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms, -NR 7 R 8 ; R 6 , R 7 and R 8 Selected from a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms; n1 and n5 are selected from any integer from 0 to 4; n2 is selected from any integer from 0 to 5; n3 and n4 are selected from any integer from 0 to 3; * indicates the attachment site.

2. The organic compound according to claim 1, characterized in that The organic compound is selected from any one of the compounds represented by Formula I-1 and Formula I-2:

3. The organic compound according to claim 1 or 2, characterized in that R 1 is selected from tert-butyl or phenyl, R 4 and R 5 Any one selected from hydrogen, deuterium, methyl, tert-butyl and phenyl.

4. The organic compound according to claim 1 or 2, characterized in that The organic compound is selected from any one of the following compounds:

5. A mixture, characterized in that The mixture comprises at least one organic functional material and at least one organic compound as described in any one of claims 1 to 4, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron injection materials, electron transport materials, luminescence auxiliary materials, hole blocking materials, organic light-emitting guest materials, organic host materials and organic dyes.

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

7. A light emitting device, characterized in that: The light-emitting device includes a first electrode, a second electrode, and an organic functional layer located between the first electrode and the second electrode, wherein the material of the organic functional layer includes at least one of the organic compounds described in any one of claims 1 to 4, or the material of the organic functional layer includes the mixture described in claim 5, or the organic functional layer is made of the composition described in claim 6.

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

9. The light emitting device according to claim 8, characterized in that: The doping material is a blue light fluorescent doping material.

10. A display panel, characterized in that: The light emitting device comprises the light emitting device as claimed in any one of claims 7 to 9.

Images