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

Abstract

The invention discloses an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. The organic compound has a structure as shown in a general formula (1): # imgabs0 #. The organic compound is easy to purify, the purity of the organic compound is improved, the luminous efficiency of the organic light-emitting device is improved, and the service life of the organic light-emitting device is prolonged.

Description

Technical Field

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

[0002] At present, organic electroluminescent elements such as organic light-emitting diodes (OLEDs) generally have an anode, a cathode, and an organic layer 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 the organic electroluminescent element, the organic layer is often multi-layered, and the organic matter of each layer is different. Specifically, the organic layer mainly includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the anode and the cathode of the organic electroluminescent element, the anode injects holes into the organic layer, and the cathode injects electrons into the organic layer. The injected holes meet with the electrons to form excitons, and the excitons emit light when they transition back to the ground state, thereby realizing the luminescence of the organic electroluminescent element. The organic electroluminescent element has the characteristics of autonomous luminescence, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast, and high response. Therefore, organic electroluminescent devices have broad application prospects.

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

[0004] In order to overcome the above problems, the existing technology is usually based on various material combinations of organic compounds, such as composite excited state materials, thermally activated delayed fluorescence (TADF) materials, etc., trying to use reverse internal conversion to achieve high efficiency comparable to phosphorescent organic electroluminescent elements. However, the performance improvement of traditional organic compounds with TADF is limited in terms of efficiency and life, resulting in difficulty in improving the luminous efficiency and service life of organic electroluminescent elements using organic compounds with TADF. Summary of the invention

[0005] The embodiments of the present application provide an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. The organic compound is easy to purify and has high purity, which is beneficial to improving the luminous efficiency and service life of the organic light-emitting device.

[0006] In order to achieve the above object, the present invention provides an organic compound having a structure as shown in the general formula (1):

[0007]

[0008] Among them, Ar 1 A group selected from any one of formula (A-1) to formula (A-7):

[0009]

[0010] Ar 2 A group selected from any one of formula (B-1) to formula (B-10):

[0011]

[0012] X is selected from O, S, N-CH 3 , N-Ph or C(CH 3 ) 2 ;

[0013] n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0014] R 0 is selected from an alkyl group having 1 to 4 carbon atoms or Ar 1 or Ar 2 Group, R 0 It can also combine with the benzene ring to form Ar 1 or Ar 2 Group;

[0015] n0 is selected from 1, 2 or 3;

[0016] R 1selected from H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear silicon group having 1 to 20 carbon atoms, a branched silicon group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, 0 branched thioalkoxy group, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a trimethylsilyl group, a triphenylsilyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF 3 , Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms.

[0017] In one embodiment of the present application, Ar 2 A group selected from any one of the formulas (B-9) to (B-10);

[0018] Or, when Ar 2 When selected from the group represented by the formula (B-10), Ar 1 A structure selected from any one of the above formulae (A-1) to (A-7).

[0019] In one embodiment of the present application, R 0 is selected from an alkyl group having 1 to 4 carbon atoms, and n0 is selected from 1, 2 or 3;

[0020] In one embodiment of the present application, R 1 It is selected from H, D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, and a cyclic alkyl group having 3 to 10 carbon atoms.

[0021] In one embodiment of the present application, R 1 It is selected from H, D, a straight-chain alkyl group having 1 to 4 carbon atoms, and a branched-chain alkyl group having 3 to 5 carbon atoms.

[0022] In one embodiment of the present application, when Ar 1 When it is a group represented by the formula (A-2), the group represented by the formula (B-2) is selected from:

[0023] as well as At least one of .

[0024] In one embodiment of the present application, the organic compound is a blue light-emitting material.

[0025] According to the above-mentioned purpose of the present application, an embodiment of the present application also provides a mixture, which includes the organic compound and at least one organic functional material, and the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes.

[0026] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a composition, which includes the organic compound and at least one organic solvent, or the composition includes the mixture and at least one organic solvent.

[0027] According to the above-mentioned purpose of the present application, the embodiment of the present application further provides an organic light-emitting device, which includes:

[0028] a first electrode;

[0029] a second electrode, disposed opposite to the first electrode; and

[0030] an organic functional layer, located between the first electrode and the second electrode;

[0031] The material of the organic functional layer includes one or more of the organic compounds, or the material of the organic functional layer includes the mixture, or the material of the organic functional layer includes the combination.

[0032] In one embodiment of the present application, the organic functional layer includes a light-emitting layer, and the material of the light-emitting layer includes a host material and a guest material, and the guest material includes one or more of the organic compounds.

[0033] In one embodiment of the present application, the mass ratio of the host material to the guest material ranges from 99:1 to 70:30.

[0034] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a display panel, which includes the organic light-emitting device.

[0035] The present application provides an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. By introducing a large group and a multi-C1-C4 alkyl group, such as an alkyl silicon group and a dibenzofuran group, into the hydrazine of the boron nitrogen compound benzothiophene, or introducing a silicon-containing group, an indenecarbazole group, an indolecarbazole group, a fluorenecarbazole, a triazine, a dicarbazolylphenyl group, a 2,6-diphenylphenyl group and a phenyl group into the para position of the boron, the organic compound is easy to purify, thereby improving the purity of the organic compound, and further improving the luminous efficiency and service life of the organic light-emitting device made of the organic compound.

[0036] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0037] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for use in the description of the embodiments. Obviously, the drawings described below are only some embodiments of the present application, and those skilled in the art can obtain other drawings based on these drawings without creative work.

[0038] 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.

[0039] Figure 1 is a hydrogen nuclear magnetic resonance spectrum of the organic compound M1 provided in the examples of the present application;

[0040] Figure 2 is a hydrogen nuclear magnetic resonance spectrum of the organic compound M2 provided in the examples of the present application;

[0041] Figure 3 This is a schematic diagram of the first structure of an organic light-emitting device provided in an embodiment of the present application;

[0042] Figure 4 This is a schematic diagram of the second structure of the organic light-emitting device provided in the embodiment of the present application.

[0043] Description of reference numerals:

[0044] 100. Organic light-emitting device; 110. Substrate; 101. First electrode; 102. Second electrode; 103. Organic functional layer; 104. Hole injection layer; 105. Hole transport layer; 106. Electron blocking layer; 107. Light-emitting layer; 108. Electron transport layer; 109. Electron injection layer. DETAILED DESCRIPTION

[0045] The present application provides an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. In order to make the purpose, technical solution and effect of the present application clearer and more specific, the present application is further described in detail with reference to the accompanying drawings and examples. It should be understood that the specific embodiments described herein are only used to explain the present application and are not used to limit the present application.

[0046] It should be noted that the description order of the following embodiments is not intended to limit the preferred order of the embodiments.

[0047] Unless otherwise defined, all terms (including technical and scientific terms) used in this article have the same meaning as commonly understood by ordinary technicians in the field to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as their meanings consistent with their meanings in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly defined in this article.

[0048] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0049] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0050] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0051] In the present application, when the same substituent appears multiple times, it can be independently selected from the same or different groups. If the general formula contains multiple R, then R can be independently selected from different or the same groups.

[0052] 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 group, isocyano group, nitro group or halogen (e.g., F, Cl, Br or I), alkyl group 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 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 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 group, isocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group. Preferably, R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen (such as F, Cl, Br or I), alkyl group 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, 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 may be further substituted by substituents acceptable in the art.

[0053] 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.

[0054] In the present application, "aryl" or "aromatic group" refers to an aromatic hydrocarbon group whose ring atoms derived from an aromatic ring compound by removing a hydrogen atom are all carbon atoms. It 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, perylenyl, naphthyl, fluorenyl, acenaphthene and its derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (for example, based on the total number of atoms in the system, the non-aromatic units preferably contain <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0055] In the present application, "heteroaryl" or "heteroaromatic group" means that at least one carbon atom on the ring skeleton is replaced by a non-carbon atom on the basis of the aryl, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. That is, the ring atoms of the heteroaryl include one or more non-carbon atoms selected from N atoms, O atoms, and S atoms. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to 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 is optionally further substituted. Suitable examples include, but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidine yl, triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, furidinyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0056] In this application, "alkyl" may refer to a fully saturated straight chain, branched chain and / or cyclic aliphatic hydrocarbon 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 "C1-9 "Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, each occurrence of which can be independently C 1 Alkyl, C 2 Alkyl, C 3 Alkyl, C 4 Alkyl, C 5 Alkyl, C 6 Alkyl, C 7 Alkyl, C 8 Alkyl or C 9 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, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyl decyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like.

[0057] In the present application, the abbreviations of substituents correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me-methyl, Et-ethyl, Pr-propyl, Bu-butyl, Am-n-pentyl, Hx-hexyl, Cy-cyclohexyl.

[0058] In this application, "amino" refers to an amine derivative having the formula -N(X) 2 The structural features of wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amine groups include -NH 2 、-N(alkyl) 2、-NH(alkyl), -N(cycloalkyl) 2 、-NH(cycloalkyl), -N(heterocyclic) 2 、-NH(heterocyclic group), -N(aryl group) 2 , -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), and the like.

[0059] Herein, the term "cycloalkyl" or "cyclic alkyl" refers to a monovalent group having one or more saturated rings in which all ring members are carbon, wherein the term "alkyl" has the same meaning as described above.

[0060] In the present application, the term "heterocyclyl", "heterocyclic" or "heterocycle" refers to a fully saturated or partially unsaturated, but non-aromatic cyclic group having one or more oxygen, sulfur, silicon or nitrogen heteroatoms in the ring, the nitrogen and sulfur heteroatoms may be optionally oxidized and the nitrogen heteroatom may be optionally quaternized. The heterocyclic group may be attached at any atom or carbon atom of the ring or ring system and may be unsubstituted or substituted with one or more moieties as described above for the aryl group.

[0061] In the present application, unless otherwise specified, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, and amino refers to -NH 2 , formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (wherein Z represents a halogen (e.g., F, Cl, Br or I)), carbamoyl refers to -C(=O)NH 2 , isocyanate group refers to -NCO, and isothiocyanate group refers to -NCS.

[0062] In the present application, the term "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above is connected to another group via an oxygen atom. Phrases containing this term, suitable examples include but are not limited to: methoxy (-O-CH 3 or -OMe), ethoxy (-O-CH 2 CH 3 or -OEt) and tert-butyloxy (-OC(CH 3 ) 3 or -OtBu).

[0063] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0069] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0070] In this application, “two adjacent R 1 or two R 3 or two R 5 "Inter-loop" means that two adjacent R 1 or two adjacent R 3 or two adjacent R 5 The ring system can be selected from aliphatic hydrocarbon ring, aliphatic heterocyclic ring, aromatic hydrocarbon ring or aromatic heterocyclic ring.

[0071] The present application provides an organic compound having a structure as shown in general formula (1) or general formula (2):

[0072]

[0073] Among them, Ar 1 A group selected from any one of formula (A-1) to formula (A-7):

[0074]

[0075] The dotted line is Ar 1 The solid line is the attachment point of the group. 1 The attachment point of the substituent group. 2 A group selected from any one of formula (B-1) to formula (B-10):

[0076]

[0077] X is selected from O, S, N-CH 3 , N-Ph or C(CH 3 ) 2 ;

[0078] n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0079] R 0 is selected from an alkyl group having 1 to 4 carbon atoms or Ar 1 or Ar 2 Group, R 0 It can also combine with the benzene ring to form Ar 1 or Ar 2 Group;

[0080] n0 is selected from 1, 2 or 3;

[0081] R 1 selected from H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear silicon group having 1 to 20 carbon atoms, a branched silicon group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, 0 branched thioalkoxy group, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a trimethylsilyl group, a triphenylsilyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, CN, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF 3 , Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms.

[0082] The embodiments of the present application introduce large groups and multiple C1-C4 alkyl groups, such as alkyl silicon groups and dibenzofuran groups, into the hydrazine of the boron nitrogen compound benzothiophene, or introduce silicon-containing groups, indenecarbazole groups, indolecarbazole groups, fluorenecarbazole, triazine, dicarbazolylphenyl, 2,6-diphenylphenyl and phenyl groups into the para position of boron, so that the organic compound is easy to purify, thereby improving the purity of the organic compound, and further improving the luminous efficiency and service life of the organic light-emitting device made of the organic compound.

[0083] It should be noted that the large group at the para-boron position in the general formula (1) is an alkyl silicon group or a dibenzofuran group), or a silicon-containing group, an indene carbazole group, an indole carbazole group, a fluorene carbazole, a triazine, a dicarbazolylphenyl group, a 2,6-diphenylphenyl group or a phenyl group is introduced at the para-boron position, which is beneficial to the purification of the organic compound, thereby improving the purity of the organic compound, and thus improving the efficiency and life of the organic light-emitting device made of the organic compound. The large group at the para-boron position in the general formula (2) is triphenylsilicon, which can effectively narrow the half-peak width of the luminescence spectrum of the organic light-emitting device made of the organic compound.

[0084] In some embodiments, two adjacent R 1 form a ring with each other; further, two adjacent R 1 They are mutually annulated to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R 1 Mutual ring formation Wherein, * indicates the connection site.

[0085] In some embodiments, Ar 2 A group selected from any one of formula (B-9) to formula (B-10).

[0086] In some embodiments, when Ar 2 When Ar is selected from the group represented by formula (B-10), 1 A structure selected from any one of formula (A-1) to formula (A-7).

[0087] In some embodiments, R 0 is selected from an alkyl group having 1 to 4 carbon atoms, and n0 is selected from 1, 2 or 3.

[0088] In some embodiments, R 1 Selected from H, D, a straight-chain alkyl group with 1 to 10 carbon atoms, a branched-chain alkyl group with 3 to 10 carbon atoms, and a cyclic alkyl group with 3 to 10 carbon atoms; by introducing an alkyl group into the organic compound, it is beneficial to improve the solubility of the organic compound in processes such as inkjet printing, and improve the product quality of the organic light-emitting device using the organic compound.

[0089] Furthermore, in some embodiments, R 1 It is selected from H, D, a straight-chain alkyl group having 1 to 4 carbon atoms, and a branched-chain alkyl group having 3 to 5 carbon atoms.

[0090] In some embodiments, when Ar 1 When it is a group represented by the formula (A-2), the group represented by the formula (B-2) can be selected from:

[0091] as well as At least one of;

[0092] The above-mentioned groups can increase the overall molecular weight of the organic compound, making the intermolecular gaps of the organic compound larger, which is not conducive to molecular stacking, but is conducive to the transfer of holes and electrons, making the molecular hole and electron transfer capabilities of the organic compound stronger, thereby improving the luminous efficiency and service life of the organic light-emitting device made of the organic compound.

[0093] In some embodiments, the organic compound is a blue light-emitting material, and the blue light-emitting material may include one or more of the organic compounds in the above embodiments.

[0094] In some embodiments, the organic compound may be selected from the following compounds:

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112] Furthermore, the embodiments of the present application also provide a method for preparing the above-mentioned organic compound, and provide the following Examples 1 to 19 to describe in detail the preparation process of the organic compound provided in the embodiments of the present application.

[0113] Example 1

[0114] The synthetic route of organic compound M1 is as follows:

[0115]

[0116] Synthesis of intermediate 1-3:

[0117] Compound 1-1 (10 mmol), compound 1-2 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 1-3 with a molar weight of 8.89mmol and a yield of 88.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-3 was: MS (ASAP) = 392.

[0118] Synthesis of intermediate 1-5:

[0119] Compound 1-3 (10 mmol), compound 1-4 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 1-5 with a molar weight of 8.71mmol and a yield of 87.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-5 was: MS (ASAP) = 794.

[0120] Synthesis of intermediate 1-7:

[0121] Intermediate 1-5 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100° C. under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 1-7 with a molar weight of 8.04 mmol and a yield of 80.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-7 was: MS (ASAP) = 1016.

[0122] Synthesis of intermediate 1-9:

[0123] Intermediate 1-7 (10 mmol), compound 1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 1-9, with a molar weight of 7.75 mmol and a yield of 77.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-9 was: MS (ASAP) = 1204.

[0124] Synthesis of organic compound M1:

[0125] In a 250 ml three-necked flask, 10 mmol of intermediate 1-9 and 100 ml of dry tert-butylbenzene were added. 2The reaction mixture was cooled to -30°C in an atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction mixture was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C and 42 mmol After the addition of N,N-diisopropylethylamine was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120°C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent therein was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder of the product, i.e., organic compound M1, with a yield of 48.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M1 was: MS (ASAP) = 1178; and the nuclear magnetic resonance hydrogen spectrum of organic compound M1 was as follows Figure 1 shown. 1 H NMR(400MHz,Chloroform-d)δ8.58(s,1H),8.11(s,2H),7.91(s,1H),7.81(s,2H),7.67(s,2H),7.47(d,J=9.5Hz,2H),7.38-7.33(m,6H),7.30(d,J=7 .0Hz,7H),7.21(s,13H),7.10(d,J=7.6Hz,4H),7.03(s,5H),6.89(s,1H), 6.68(s,1H),6.52(s,1H),6.13(s,1H),1.29(s,9H),1.14(t,J=2.8Hz,9H).

[0126] Example 2

[0127] The synthetic route of organic compound M2 is as follows:

[0128]

[0129] Synthesis of intermediate 2-2:

[0130] Intermediate 1-5 (10 mmol), compound 2-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 2-2 with a molar weight of 8.75 mmol and a yield of 87.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-2 was: MS (ASAP) = 1016.

[0131] Synthesis of intermediate 2-3:

[0132] Intermediate 2-2 (10 mmol), compound 1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 2-3, with a molar weight of 7.31 mmol and a yield of 73.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-3 was: MS (ASAP) = 1204.

[0133] Synthesis of organic compound M2:

[0134] In a 250 ml three-necked flask, 10 mmol of intermediate 2-3 and 100 ml of dry tert-butylbenzene were added. 2The reaction mixture was cooled to -30°C in an atmosphere, and a n-hexane solution of t-BuLi (tert-butyl lithium) (21 mmol) was added dropwise. The temperature was raised to 60°C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure. The reaction mixture was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction mixture was then cooled to 0°C and 42 mmol After the addition of N,N-diisopropylethylamine was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120°C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent therein was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder of the product, i.e., organic compound M2, with a yield of 55.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M2 was: MS (ASAP) = 1178; and the nuclear magnetic resonance hydrogen spectrum of organic compound M2 was as follows Figure 2 shown. 1 H NMR(400MHz,Chloroform-d)δ8.59(s,1H),8.23-8.19(m,2H),7.99-7.91(m,1H),7.83(s,2H),7.69(s,2H),7.42(m,8H) ,7.25(m,23H),7.06-6.95(m,7H),6.65(s,1H),6.54(s,1H),6.13(s,1H),1.29(d,J=4.1Hz,9H),1.14(d,J=4.3Hz,9H).

[0135] Example 3

[0136] The synthetic route of organic compound M3 is as follows:

[0137]

[0138] Synthesis of intermediate 3-2:

[0139] Compound 1-3 (10 mmol), compound 3-1 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 3-2 with a molar weight of 8.96mmol and a yield of 89.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 3-2 was: MS (ASAP) = 608.

[0140] Synthesis of intermediate 3-3:

[0141] Intermediate 3-2 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 3-3 with a molar weight of 8.55 mmol and a yield of 85.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 3-3 was: MS (ASAP) = 830.

[0142] Synthesis of intermediate 3-4:

[0143] Intermediate 3-3 (10 mmol), compound 1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 3-4, with a molar weight of 7.19 mmol and a yield of 71.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 3-4 was: MS (ASAP) = 1018.

[0144] Synthesis of organic compound M3:

[0145] In a 250 ml three-necked flask, 10 mmol of intermediate 3-4 and 100 ml of dry tert-butylbenzene were added. 2atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M4, with a yield of 41.7%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M3: MS (ASAP) = 992;

[0146] Example 4

[0147] The synthetic route of organic compound M4 is as follows:

[0148]

[0149] Synthesis of intermediate 4-1:

[0150] The intermediate 3-2 (10 mmol), compound 2-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain the intermediate 4-1 with a molar weight of 8.32 mmol and a yield of 83.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 4-1 was: MS (ASAP) = 830.

[0151] Synthesis of intermediate 4-2:

[0152] Intermediate 4-1 (10 mmol), compound 1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 4-2, with a molar weight of 7.86 mmol and a yield of 78.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 4-2 was: MS (ASAP) = 1018.

[0153] Synthesis of organic compound M4:

[0154] In a 250 ml three-necked flask, 10 mmol of intermediate 4-2 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M4, with a yield of 36.7%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M4: MS (ASAP) = 992;

[0155] Example 5

[0156] The synthetic route of organic compound M5 is as follows:

[0157]

[0158] Synthesis of intermediate 5-2:

[0159] Compound 1-1 (10 mmol), compound 5-1 (10 mmol), Pd (dba) 2(bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 5-2 with a molar weight of 8.32mmol and a yield of 83.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 5-2 was: MS (ASAP) = 448.

[0160] Synthesis of intermediate 5-3:

[0161] Compound 5-2 (10 mmol), compound 1-4 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 5-3 with a molar weight of 8.21mmol and a yield of 82.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 5-3 was: MS (ASAP) = 850.

[0162] Synthesis of intermediate 5-4:

[0163] Intermediate 5-3 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 5-4 with a molar weight of 8.27 mmol and a yield of 82.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 5-4 was: MS (ASAP) = 1072.

[0164] Synthesis of intermediate 5-5:

[0165] Intermediate 5-4 (10 mmol), compound 1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 5-5, with a molar weight of 7.22 mmol and a yield of 72.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 5-5 was: MS (ASAP) = 1260.

[0166] Synthesis of organic compound M5:

[0167] In a 250 ml three-necked flask, 10 mmol of intermediate 5-5 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M5, with a yield of 42.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M5 was: MS (ASAP) = 1234;

[0168] Example 6

[0169] The synthetic route of organic compound M6 is as follows:

[0170]

[0171] Synthesis of intermediate 6-1:

[0172] The intermediate 5-2 (10 mmol), compound 2-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain the intermediate 6-1 with a molar weight of 8.65 mmol and a yield of 86.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 6-1 was: MS (ASAP) = 1072.

[0173] Synthesis of intermediate 6-2:

[0174] The intermediate 6-1 (10 mmol), compound 1-8 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain the intermediate 6-2, with a molar weight of 7.61 mmol and a yield of 76.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 6-2 was: MS (ASAP) = 1260.

[0175] Synthesis of organic compound M6:

[0176] In a 250 ml three-necked flask, 10 mmol of intermediate 6-2 and 100 ml of dry tert-butylbenzene were added. 2atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M6, with a yield of 52.5%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M6: MS (ASAP) = 1234;

[0177] Example 7

[0178] The synthetic route of organic compound M7 is as follows:

[0179]

[0180] Synthesis of intermediate 7-1:

[0181] Compound 5-1 (10 mmol), compound 3-1 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 7-1 with a molar weight of 8.39mmol and a yield of 83.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-1 was: MS (ASAP) = 664.

[0182] Synthesis of intermediate 7-2:

[0183] Intermediate 7-1 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 7-2 with a molar weight of 8.19 mmol and a yield of 81.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-2 was: MS (ASAP) = 886.

[0184] Synthesis of intermediate 7-3:

[0185] The intermediate 7-2 (10 mmol), compound 1-8 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain the intermediate 7-3, with a molar weight of 8.76 mmol and a yield of 87.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 7-3 was: MS (ASAP) = 1074.

[0186] Synthesis of organic compound M7:

[0187] In a 250 ml three-necked flask, 10 mmol of intermediate 7-3 and 100 ml of dry tert-butylbenzene were added. 2atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M7, with a yield of 44.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M7 was: MS (ASAP) = 1048;

[0188] Example 8

[0189] The synthetic route of organic compound M8 is as follows:

[0190]

[0191] Synthesis of intermediate 8-1:

[0192] Intermediate 7-1 (10 mmol), compound 2-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 8-1 with a molar weight of 8.93 mmol and a yield of 89.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 8-1 was: MS (ASAP) = 886.

[0193] Synthesis of intermediate 8-2:

[0194] The intermediate 8-1 (10 mmol), compound 1-8 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain the intermediate 8-2, with a molar weight of 8.49 mmol and a yield of 84.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 8-2 was: MS (ASAP) = 1074.

[0195] Synthesis of organic compound M8:

[0196] In a 250 ml three-necked flask, 10 mmol of intermediate 8-2 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M8, with a yield of 42.1%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M8: MS (ASAP) = 1048;

[0197] Example 9

[0198] The synthetic route of organic compound M9 is as follows:

[0199]

[0200] Synthesis of intermediate 9-2:

[0201] Compound 1-1 (10 mmol), compound 9-1 (10 mmol), Pd (dba) 2(bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 9-2 with a molar weight of 8.56mmol and a yield of 85.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-2 was: MS (ASAP) = 504.

[0202] Synthesis of intermediate 9-3:

[0203] Compound 9-2 (10 mmol), compound 1-4 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 9-3 with a molar weight of 8.63mmol and a yield of 86.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-3 was: MS (ASAP) = 906.

[0204] Synthesis of intermediate 9-4:

[0205] Intermediate 9-3 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 9-4 with a molar weight of 8.52 mmol and a yield of 85.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-4 was: MS (ASAP) = 1128.

[0206] Synthesis of intermediate 9-5:

[0207] Intermediate 9-4 (10 mmol), compound 1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 9-5, with a molar weight of 7.68 mmol and a yield of 76.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-5 was: MS (ASAP) = 1316.

[0208] Synthesis of organic compound M9:

[0209] In a 250 ml three-necked flask, 10 mmol of intermediate 9-5 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M9, with a yield of 49.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M9 was: MS (ASAP) = 1290;

[0210] Example 10

[0211] The synthetic route of organic compound M10 is as follows:

[0212]

[0213] Synthesis of intermediate 10-1:

[0214] Intermediate 9-2 (10 mmol), compound 2-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 10-1 with a molar weight of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 10-1 was: MS (ASAP) = 1128.

[0215] Synthesis of intermediate 10-2:

[0216] Intermediate 10-1 (10 mmol), compound 1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 10-2, with a molar weight of 8.27 mmol and a yield of 82.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 10-2 was: MS (ASAP) = 1316.

[0217] Synthesis of organic compound M6:

[0218] In a 250 ml three-necked flask, 10 mmol of intermediate 10-2 and 100 ml of dry tert-butylbenzene were added. 2atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M10, with a yield of 34.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M10 was: MS (ASAP) = 1290;

[0219] Embodiment 11

[0220] The synthetic route of organic compound M11 is as follows:

[0221]

[0222] Synthesis of intermediate 11-1:

[0223] Compound 9-1 (10 mmol), compound 3-1 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 11-1 with a molar weight of 8.81mmol and a yield of 88.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 11-1 was: MS (ASAP) = 720.

[0224] Synthesis of intermediate 11-2:

[0225] Intermediate 11-1 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 11-2 with a molar weight of 8.37 mmol and a yield of 83.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 11-2 was: MS (ASAP) = 942.

[0226] Synthesis of intermediate 11-3:

[0227] Intermediate 11-2 (10 mmol), compound 1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 11-3, with a molar weight of 8.11 mmol and a yield of 81.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 11-3 was: MS (ASAP) = 1130.

[0228] Synthesis of organic compound M11:

[0229] In a 250 ml three-necked flask, 10 mmol of intermediate 11-3 and 100 ml of dry tert-butylbenzene were added. 2atmosphere, cooled to -30°C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60°C for reaction for 2 hours, and the n-hexane solvent was removed under reduced pressure; the reaction solution was cooled to -30°C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0°C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was complete, the temperature was raised to room temperature and stirred, and the temperature was further raised to 120°C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M11, with a yield of 43.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M11 was: MS (ASAP) = 1104;

[0230] Example 12

[0231] The synthetic route of organic compound M12 is as follows:

[0232]

[0233] Synthesis of intermediate 12-1:

[0234] Intermediate 11-1 (10 mmol), compound 2-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 12-1 with a molar weight of 8.38 mmol and a yield of 83.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-1 was: MS (ASAP) = 942.

[0235] Synthesis of intermediate 12-2:

[0236] Intermediate 12-1 (10 mmol), compound 1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 12-2, with a molar weight of 8.49 mmol and a yield of 84.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 12-2 was: MS (ASAP) = 1130.

[0237] Synthesis of organic compound M12:

[0238] In a 250 ml three-necked flask, 10 mmol of intermediate 12-2 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M12, with a yield of 43.8%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M12: MS (ASAP) = 1104;

[0239] Embodiment 13

[0240] The synthetic route of organic compound M13 is as follows:

[0241]

[0242] Synthesis of intermediate 13-2:

[0243] Intermediate 1-3 (10 mmol), compound 13-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 13-2 with a molar weight of 6.54 mmol and a yield of 65.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 13-2 was: MS (ASAP) = 614.

[0244] Synthesis of intermediate 13-3:

[0245] Intermediate 13-2 (10 mmol), compound 2-1 (10 mmol) Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 13-3, with a molar weight of 7.28 mmol and a yield of 72.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 13-3 was: MS (ASAP) = 792.

[0246] Synthesis of intermediate 13-4:

[0247] Intermediate 13-3 (10 mmol), compound 1-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 13-4, with a molar weight of 7.87 mmol and a yield of 78.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 13-4 was: MS (ASAP) = 980.

[0248] Synthesis of intermediate 13-5:

[0249] The intermediate 13-4 (10 mmol), pinacol borate (20 mmol), palladium acetate (0.1 mmol) and potassium acetate (30 mmol) were dissolved in 1,4-dioxane, heated to 100°C and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain the intermediate 13-5 with a molar weight of 7.88 mmol and a yield of 78.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 13-5 was: MS (ASAP) = 1072.

[0250] Synthesis of intermediate 13-7:

[0251] Intermediate 13-5 (10 mmol) and intermediate 13-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh 3 ) 4 (0.1mmol) and potassium carbonate (30mmol), under a nitrogen atmosphere, the temperature was raised to 100°C and stirred for 6h; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was column chromatographed and recrystallized to obtain an intermediate 13-7 with a molar weight of 8.24mmol and a yield of 82.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 13-7 was: MS (ASAP) = 1185.

[0252] Synthesis of organic compound M13:

[0253] In a 250 ml three-necked flask, 10 mmol of intermediate 13-7 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M13, with a yield of 47.3%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M13: MS (ASAP) = 1159;

[0254] Embodiment 14

[0255] The synthetic route of organic compound M14 is as follows:

[0256]

[0257] Synthesis of intermediate 14-2:

[0258] Intermediate 13-5 (10 mmol) and intermediate 14-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh 3 ) 4 (0.1mmol) and potassium carbonate (30mmol), under a nitrogen atmosphere, the temperature was raised to 100°C and stirred for 6h; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was column chromatographed and recrystallized to obtain an intermediate 14-2 with a molar weight of 8.35mmol and a yield of 83.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 14-2 was: MS (ASAP) = 1198.

[0259] Synthesis of organic compound M14:

[0260] 10 mmol of intermediate 14-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M14, with a yield of 39.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M14 was: MS (ASAP) = 1172.

[0261] Embodiment 15

[0262] The synthetic route of organic compound M15 is as follows:

[0263]

[0264] Synthesis of intermediate 15-2:

[0265] Intermediate 13-5 (10 mmol) and intermediate 15-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh 3 ) 4 (0.1mmol) and potassium carbonate (30mmol), under a nitrogen atmosphere, the temperature was raised to 100°C and stirred for 6h; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was column chromatographed and recrystallized to obtain an intermediate 15-2 with a molar weight of 8.17mmol and a yield of 81.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the intermediate 15-2 was: MS (ASAP) = 1352.

[0266] Synthesis of organic compound M15:

[0267] In a 250 ml three-necked flask, 10 mmol of intermediate 15-2 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M15, with a yield of 40.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M15 was: MS (ASAP) = 1326.

[0268] Example 16

[0269] The synthetic route of organic compound M16 is as follows:

[0270]

[0271] Synthesis of intermediate 16-2:

[0272] Intermediate 13-4 (10 mmol), intermediate 16-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 16-2 with a molar weight of 8.72 mmol and a yield of 87.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 16-2 was: MS (ASAP) = 1276.

[0273] Synthesis of organic compound M16:

[0274] In a 250 ml three-necked flask, 10 mmol of intermediate 16-2 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M16, with a yield of 32.3%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M16: MS (ASAP) = 1250.

[0275] Embodiment 17

[0276] The synthetic route of organic compound M17 is as follows:

[0277]

[0278] Synthesis of intermediate 17-2:

[0279] Intermediate 13-4 (10 mmol), intermediate 17-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 17-2 with a molar weight of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 17-2 was: MS (ASAP) = 1276.

[0280] Synthesis of organic compound M17:

[0281] In a 250 ml three-necked flask, 10 mmol of intermediate 17-2 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M17, with a yield of 35.1%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M17: MS (ASAP) = 1250.

[0282] Embodiment 18

[0283] The synthetic route of organic compound M18 is as follows:

[0284]

[0285] Synthesis of intermediate 18-2:

[0286] Intermediate 13-4 (10 mmol), intermediate 18-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 18-2 with a molar weight of 8.26 mmol and a yield of 82.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 18-2 was: MS (ASAP) = 1276.

[0287] Synthesis of organic compound M18:

[0288] In a 250 ml three-necked flask, 10 mmol of intermediate 18-2 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M18, with a yield of 53.9%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M18: MS (ASAP) = 1250.

[0289] Embodiment 19

[0290] The synthetic route of organic compound M19 is as follows:

[0291]

[0292] Synthesis of intermediate 19-2:

[0293] Intermediate 13-4 (10 mmol), intermediate 19-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 19-2 with a molar weight of 8.57 mmol and a yield of 85.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 19-2 was: MS (ASAP) = 1227.

[0294] Synthesis of organic compound M19:

[0295] In a 250 ml three-necked flask, 10 mmol of intermediate 19-2 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, the temperature was raised to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M19, with a yield of 42.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M19 was: MS (ASAP) = 1201.

[0296] Embodiment 20

[0297] The synthetic route of organic compound M20 is as follows:

[0298]

[0299] Synthesis of intermediate 20-2:

[0300] Compound 20-1 (10 mmol), compound 1-4 (10 mmol), Pd (dba) 2(bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 20-2 with a molar weight of 8.36mmol and a yield of 83.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 20-2 was: MS (ASAP) = 739.

[0301] Synthesis of intermediate 20-3:

[0302] Compound 20-2 (10 mmol), compound 1-1 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 20-3 with a molar weight of 8.62mmol and a yield of 86.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 20-3 was: MS (ASAP) = 963.

[0303] Synthesis of intermediate 20-5:

[0304] Intermediate 20-3 (10 mmol), compound 20-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 20-5 with a molar weight of 8.18 mmol and a yield of 81.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 20-5 was: MS (ASAP) = 1071.

[0305] Synthesis of intermediate 20-7:

[0306] Intermediate 20-5 (10 mmol), compound 20-6 (10 mmol) and cesium carbonate (80 mmol) were dissolved in DMF, heated to 140°C and stirred for 12 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 20-7 with a molar weight of 7.32 mmol and a yield of 73.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 20-7 was: MS (ASAP) = 1218.

[0307] Synthesis of organic compound M20:

[0308] In a 250 ml three-necked flask, 10 mmol of intermediate 20-7 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M20, with a yield of 51.5%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M20: MS (ASAP) = 1192;

[0309] Embodiment 21

[0310] The synthetic route of organic compound M21 is as follows:

[0311]

[0312] Synthesis of intermediate 21-2:

[0313] Intermediate 20-3 (10 mmol), compound 21-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 21-2 with a molar weight of 8.56 mmol and a yield of 85.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 21-2 was: MS (ASAP) = 1113.

[0314] Synthesis of intermediate 21-3:

[0315] Intermediate 21-2 (10 mmol), compound 20-6 (10 mmol) and cesium carbonate (80 mmol) were dissolved in DMF, heated to 140°C and stirred for 12 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 21-3 with a molar weight of 7.13 mmol and a yield of 71.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 21-3 was: MS (ASAP) = 1260.

[0316] Synthesis of organic compound M21:

[0317] In a 250 ml three-necked flask, 10 mmol of intermediate 21-3 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M21, with a yield of 52.8%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M21: MS (ASAP) = 1234;

[0318] Embodiment 22

[0319] The synthetic route of organic compound M22 is as follows:

[0320]

[0321] Synthesis of intermediate 22-1:

[0322] Intermediate 20-3 (10 mmol), compound 13-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 22-1 with a molar weight of 8.95 mmol and a yield of 89.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 22-1 was: MS (ASAP) = 1202.

[0323] Synthesis of organic compound M22:

[0324] 10 mmol of intermediate 22-1 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phases were combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M22, with a yield of 56.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M22 was: MS (ASAP) = 1176;

[0325] Embodiment 23

[0326] The synthetic route of organic compound M23 is as follows:

[0327]

[0328] Synthesis of intermediate 23-2:

[0329] Compound 23-1 (10 mmol), compound 1-8 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 23-2 with a molar weight of 8.85mmol and a yield of 88.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 23-2 was: MS (ASAP) = 337.

[0330] Synthesis of intermediate 23-3:

[0331] Compound 23-2 (10 mmol), compound 1-4 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 23-3 with a molar weight of 8.52mmol and a yield of 85.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 23-3 was: MS (ASAP) = 739.

[0332] Synthesis of intermediate 23-4:

[0333] Compound 23-3 (10 mmol), compound 1-1 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 23-4 with a molar weight of 8.13mmol and a yield of 81.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 23-4 was: MS (ASAP) = 963.

[0334] Synthesis of intermediate 23-5:

[0335] Intermediate 23-4 (10 mmol), compound 20-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 23-5 with a molar weight of 8.67 mmol and a yield of 86.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 23-5 was: MS (ASAP) = 1071.

[0336] Synthesis of intermediate 23-6:

[0337] The intermediate 23-5 (10 mmol), compound 20-6 (10 mmol) and cesium carbonate (80 mmol) were dissolved in DMF, heated to 140°C and stirred for 12 h under a nitrogen atmosphere; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain the intermediate 23-6 with a molar weight of 6.43 mmol and a yield of 64.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 23-6 was: MS (ASAP) = 1218.

[0338] Synthesis of organic compound M23:

[0339] In a 250 ml three-necked flask, 10 mmol of intermediate 23-6 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M23, with a yield of 52.1%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M23: MS (ASAP) = 1192;

[0340] Embodiment 24

[0341] The synthetic route of organic compound M24 is as follows:

[0342]

[0343] Synthesis of intermediate 24-2:

[0344] Compound 1-1 (10 mmol), compound 24-1 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 24-2 with a molar weight of 8.33mmol and a yield of 83.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 24-2 was: MS (ASAP) = 426.

[0345] Synthesis of intermediate 24-3:

[0346] Compound 24-2 (10 mmol), compound 1-4 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 24-3 with a molar weight of 8.17mmol and a yield of 81.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 24-3 was: MS (ASAP) = 828.

[0347] Synthesis of intermediate 24-5:

[0348] Compound 23-3 (10 mmol), compound 24-4 (10 mmol), Pd (dba) 2 (bis(dibenzylideneacetonepalladium, 0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 24-5 with a molar weight of 8.67mmol and a yield of 86.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 24-5 was: MS (ASAP) = 997.

[0349] Synthesis of intermediate 24-7:

[0350] Intermediate 24-5 (10 mmol), compound 24-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 24-7 with a molar weight of 8.39 mmol and a yield of 83.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 24-7 was: MS (ASAP) = 1238.

[0351] Synthesis of organic compound M24:

[0352] In a 250 ml three-necked flask, 10 mmol of intermediate 24-7 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M24, with a yield of 38.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M24 was: MS (ASAP) = 1212;

[0353] Embodiment 25

[0354] The synthetic route of organic compound M25 is as follows:

[0355]

[0356] Synthesis of intermediate 25-2:

[0357] Intermediate 24-5 (10 mmol), compound 25-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, heated to 100°C under a nitrogen atmosphere and stirred for 6 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography to obtain intermediate 25-2 with a molar weight of 7.43 mmol and a yield of 74.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 25-2 was: MS (ASAP) = 1238.

[0358] Synthesis of organic compound M25:

[0359] In a 250 ml three-necked flask, 10 mmol of intermediate 25-2 and 100 ml of dry tert-butylbenzene were added. 2 atmosphere, cooled to -30 ° C, t-BuLi (tert-butyl lithium) (21 mmol) n-hexane solution was added dropwise, the temperature was raised to 60 ° C for reaction for 2 hours, and the n-hexane solvent was evaporated under reduced pressure; the reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours, and then the reaction solution was cooled to 0 ° C, 42 mmol N, N-diisopropylethylamine was added, and after the addition was completed, the temperature was raised to room temperature and stirred, and then the temperature was further raised to 120 ° C and stirred for 3 hours, and the reaction solution was cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate and the organic phase was combined, and the solvent was evaporated to obtain a crude product, which was purified by rapid silica gel column to obtain a pure product; recrystallized with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M25, with a yield of 37.3%, and the atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M25: MS (ASAP) = 1212;

[0360] In the embodiments of the present application, large groups such as alkyl silicon groups and dibenzofuran groups are introduced into the hydrazine of the boron nitrogen compound benzothiophene, or silicon-containing groups, indenecarbazole groups, indolecarbazole groups, fluorenecarbazole, triazine, dicarbazolylphenyl, 2,6-diphenylphenyl and phenyl groups are introduced into the para position of boron, so that the organic compound is easy to purify, thereby improving the purity of the organic compound, and further improving the luminous efficiency and service life of the organic light-emitting device made of the organic compound.

[0361] An embodiment of the present application also provides a mixture, which includes the organic compound described in the above embodiment and at least one organic functional material; in some embodiments, when the mixture provided by the embodiment of the present application is used in an organic light-emitting device, the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes.

[0362] In addition, embodiments of the present application further provide a composition, which includes the organic compound described in the above embodiments and at least one organic solvent, or the composition includes the mixture described in the above embodiments and at least one organic solvent.

[0363] In some embodiments, the composition may be a solution or a suspension, and the composition may include a dispersant and a dispersant, wherein the dispersant is one or more of the organic compounds described above and at least one organic solvent, or the dispersant is a mixture described above, and the dispersant is used to disperse the dispersant.

[0364] In the composition, the mass fraction of the organic compound as described above may be 0.3% to 30%, preferably 0.5% to 20%, more preferably 0.5% to 15%, further preferably 0.5% to 10%, most preferably 1% to 5%.

[0365] When the composition is used in a printing process, the composition can be an ink, and the viscosity and surface tension of the ink are important parameters. The surface tension parameters of the appropriate ink are suitable for a specific substrate and a specific printing method. In some embodiments, the surface tension of the ink at the working temperature or at 25°C ranges from 19 dyne / cm to 50 dyne / cm; preferably 22 dyne / cm to 35 dyne / cm; more preferably 25 dyne / cm to 33 dyne / cm, which is advantageous for use in an inkjet printing process. In some embodiments, the viscosity of the ink at the working temperature or at 25°C ranges from 1 cps to 100 cps; preferably 1 cps to 50 cps; more preferably 1.5 cps to 20 cps; most preferably 4.0 cps to 20 cps, which is advantageous for use in an inkjet printing process.

[0366] In some embodiments, the Hansen solubility parameter of the dispersant is within the following range: the δd (dispersion force) of the dispersant is between 17.0 and 23.2 MPa. 1 / 2 The range is preferably 18.5 to 21.0 MPa 1 / 2 Range; δp (polar force) is 0.2~12.5MPa 1 / 2The range is preferably 2.0 to 6.0 MPa. 1 / 2 The range of δh (hydrogen bond force) is 0.9~14.2MPa 1 / 2 The range is preferably 2.0 to 6.0 MPa. 1 / 2 range.

[0367] In some embodiments, the boiling point of the dispersant is greater than or equal to 150° C., preferably greater than or equal to 180° C., more preferably greater than or equal to 200° C., more preferably greater than or equal to 250° C., further preferably greater than or equal to 275° C., and most preferably greater than or equal to 300° C. The boiling point of the dispersant is at least greater than or equal to 150° C., which is beneficial to preventing the nozzle of the inkjet print head from being blocked during inkjet printing, and the higher the boiling point, the more beneficial it is to preventing blockage.

[0368] The dispersant may include at least one organic solvent, which may be evaporated from the solvent system to form a film containing the functional material. The organic solvent may be selected from aromatic or heteroaromatic. Specifically, the organic solvent may be selected from p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, Benzene, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0369] The organic solvent can also be selected from aromatic ketone solvents. Specifically, the organic solvent can be selected from 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0370] The organic solvent can also be selected from aromatic ether solvents. Specifically, the organic solvent can be selected from 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl 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, ethyl-2-naphthyl ether, etc.

[0371] The organic solvent can also be selected from aliphatic ketones, such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, such as amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0372] The organic solvent can also be selected from organic ester solvents. Specifically, the first solvent can be selected from alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0373] The organic solvent can also be selected from one or more of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and the like.

[0374] In addition to the dispersoid and the dispersant, the composition may also include one or more components such as surfactant compounds, lubricants, wetting agents, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0375] In addition, please refer to Figure 3, an embodiment of the present application further provides an organic light-emitting device 100, the organic light-emitting device 100 comprising: a first electrode 101 and a second electrode 102; an organic functional layer 103 located between the first electrode 101 and the second electrode 102; wherein the material of the organic functional layer 103 comprises one or more of the organic compounds described in the above embodiments, or the material of the organic functional layer 103 comprises the mixture described in the above embodiments, or the material of the organic functional layer 103 comprises the combination described in the above embodiments.

[0376] In some embodiments, the first electrode 101 may be an anode, and the second electrode 102 may be a cathode.

[0377] In some embodiments, the organic light-emitting device 100 can be used for an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting cell, an organic field effect transistor, an organic light-emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emission diode, etc., preferably an organic light-emitting diode, an organic light-emitting cell, and an organic light-emitting field effect transistor.

[0378] In some embodiments, the organic light-emitting device 100 can be applied to a variety of electronic devices, such as display panels, lighting devices, light sources, etc.

[0379] In some embodiments, the organic functional layer 103 may be a single layer. In this case, the organic functional layer 103 is a mixture layer, and the mixture layer includes a first compound and a second compound. The first compound is selected from one or more of the organic compounds described above, and the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, luminescent guest materials, luminescent host materials, and organic dyes. Detailed descriptions of various organic functional materials included in the organic functional layer 103 are detailed in WO2010135519A1, US20090134784A1, and WO 2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0380] The luminescent guest material is selected from a singlet luminescent body (fluorescent luminescent body), a triplet luminescent body (phosphorescent luminescent body) and a TADF material.

[0381] When the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, light-emitting host materials, and organic dyes, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.

[0382] When the second compound is a light-emitting guest material, the mass ratio of the first compound to the second compound is 99:1 to 70:30, preferably 99:1 to 90:10.

[0383] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is multiple layers, the organic functional layer 103 at least includes a light-emitting layer 107; preferably, the organic functional layer 103 includes a hole injection layer 104, a hole transport layer 105, an electron blocking layer 106, a light-emitting layer 107, an electron injection layer 109, and an electron transport layer 108; in other embodiments of the present application, the organic functional layer 103 may further include a hole blocking layer disposed between the light-emitting layer 107 and the electron transport layer 108.

[0384] In some embodiments, the organic light-emitting device 100 may be a blue organic light-emitting device, a green organic light-emitting device or a red organic light-emitting device, and the light-emitting layer 107 may include a host material and a guest material, the guest material is one or more of the organic compounds described above, and the host material includes a condensed aromatic derivative or a heteroaromatic compound.

[0385] The light emitting wavelength of the organic light emitting device 100 is between 300nm and 1000nm; further, the light emitting wavelength of the organic light emitting device 100 is between 350nm and 900nm; further, the light emitting wavelength of the organic light emitting device 100 is between 400nm and 800nm; further, the light emitting wavelength of the organic light emitting device 100 is within the wavelength range of blue light.

[0386] In some embodiments, the host material includes at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. Preferably, the host material is a blue light host material used in a blue organic light-emitting device; when the host material is a blue light host material, the host material is preferably an anthracene organic compound.

[0387] In some embodiments, the mass ratio of the host material to the guest material ranges from 99:1 to 70:30, such as 90:10, 85:15, 80:20, 75:25, etc.; preferably 99:1 to 90:10, such as 97:3, 96:4, 95:5, 93:7, 92:8, etc. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 99:1 to 70:30, which is conducive to inhibiting the crystallization of the light-emitting layer 107 and inhibiting concentration quenching caused by high concentration of the guest material, thereby improving the luminous efficiency of the organic light-emitting device 100.

[0388] In some embodiments, the anode is an electrode for injecting holes, and the anode can inject holes into the organic functional layer 103, such as: the anode injects holes into the hole injection layer, the hole transport layer or the light-emitting layer. The anode may include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) energy level or valence band energy level of the p-type semiconductor material as the hole injection layer, or the HOMO (Highest Occupied Molecular Orbital) energy level or valence band energy level of the p-type semiconductor material in the hole injection layer and the hole transport layer or the electron blocking layer are less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The material of the anode includes but is not limited to at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), etc., or other suitable and known anode materials, which can be easily selected and used by ordinary technicians in this field. The material of the anode can be deposited using any suitable technology, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be patterned, such as: patterned ITO conductive substrates are available on the market and can be used to prepare the organic light-emitting device 100 of the present application.

[0389] In some embodiments, the cathode is an electrode for injecting electrons, and the cathode can inject electrons into the organic functional layer, such as: the cathode injects electrons into the electron injection layer, the electron transport layer, or the light-emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of an n-type semiconductor material as an electron injection layer, or the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of an n-type semiconductor material of an electron injection layer and an electron transport layer or a hole blocking layer are less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes of organic electronic devices may be used as cathode materials of the device of the present application, and the materials of the cathode include but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF 2 / at least one of Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The material of the cathode can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0390] In some embodiments, the hole injection layer 104 is used to promote the injection of holes from the anode to the light-emitting layer 107, and the hole injection layer 104 includes a hole injection material, which is a material that can receive holes injected from the positive electrode at a low voltage, and preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the material of the anode and the HOMO of the functional material of the film layer (such as the hole transport material of the hole transport layer) into which the holes are injected away from the anode. The hole injection material includes but is not limited to at least one of metal porphyrin, oligothiophene, organic material based on arylamine, organic material based on hexanitrile hexaazatriphenylene, organic material based on quinacridone, organic material based on perylene, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc.

[0391] In some embodiments, the hole transport layer 105 can be used to transport holes to the light-emitting layer 107. The hole transport layer 105 includes a hole transport material, which receives holes transmitted from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material with high hole mobility known in the art, and the hole transport material may include but is not limited to at least one of an organic material based on arylamine, a conductive polymer, a block copolymer having both a conjugated part and a non-conjugated part, and the like.

[0392] In some embodiments, the electron transport layer 108 is used to transport electrons, and the electron transport layer 108 includes an electron transport material, which receives electrons injected from the negative electrode and transfers the electrons to the light-emitting layer 107. The electron transport material is a material with high electron mobility known in the art, and the electron transport material may include but is not limited to: at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), and a benzimidazole-based compound.

[0393] In some embodiments, the electron injection layer 109 is used to inject electrons, and the electron injection layer 109 includes an electron injection material, and the electron injection material preferably has the ability to transport electrons, has the effect of injecting electrons from the negative electrode, has an excellent effect of injecting electrons into the light-emitting layer 107 or the light-emitting material, and has the ability to prevent the excitons generated by the light-emitting layer 107 from moving to the hole injection layer, and also has an excellent ability to form a thin film. The electron injection material includes, but is not limited to, at least one of 8-hydroxyquinoline lithium (LiQ), fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, pyrazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc.

[0394] In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode, and can generally be formed under the same conditions as the hole injection layer 104. The hole blocking layer includes a hole blocking material, which includes but is not limited to at least one of diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like.

[0395] In some embodiments, the organic light-emitting device 100 further includes a substrate 110, and the first electrode 101, the hole injection layer 104, the hole transport layer 105, the electron blocking layer 106, the light-emitting layer 107, the electron transport layer 108, the electron injection layer 109, and the second electrode 102 are sequentially stacked on the substrate 110. The substrate 110 may be a transparent substrate or an opaque substrate. When the substrate 110 is a transparent substrate, a transparent organic light-emitting device 100 may be manufactured; the substrate 110 may be a rigid substrate or a flexible substrate with elasticity, and the material of the substrate 110 may include but is not limited to plastic, polymer, metal, semiconductor wafer or glass. Preferably, the substrate 110 includes at least one smooth surface for forming the anode on the surface. More preferably, the surface has no surface defects. Preferably, the material of the substrate 110 is a polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material), and the glass transition temperature of the substrate 110 is greater than or equal to 150°C, preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, and most preferably greater than or equal to 300°C.

[0396] In some embodiments, the organic light-emitting device 100 may be a solution-type organic light-emitting device, that is, at least one of the organic functional layers is prepared by printing (eg, inkjet printing).

[0397] In some embodiments, the mixture layer or the luminescent layer can be formed by a printing or coating process of the composition. The printing or coating process includes 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 or pad printing, slit extrusion coating, etc. Preferably, it is gravure printing, nozzle printing and inkjet printing.

[0398] Furthermore, the examples of the present application calculate the HOMO energy level, LUMO energy level, S1 energy level and T1 energy level of the organic compounds shown in the above-mentioned Examples 1 to 25 and the comparative compound 1 in Comparative Example 1 to verify the performance of the organic compounds provided by the examples of the present application.

[0399] The structural formula of comparative compound 1 is:

[0400]

[0401] As shown in Table 1 below, the HOMO (Highest Occupied Molecular Orbital) energy level, LUMO (Lowest Unoccupied Molecular Orbital) energy level, T1 (first excited triplet state) energy level, and S1 (first excited singlet state) energy level of the compounds M1 to M25 obtained in Examples 1 to 25 and the comparative compound 1 in Comparative Example 1 can be obtained by quantum calculation. Specifically, TD-DFT (time-dependent density functional theory) is used through Gaussian09W (Gaussian Inc.). The specific simulation method can be found in WO2011141110. First, the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / SpinSinglet) is used to optimize the molecular geometry. Then the energy structure of the organic molecule is calculated by TD-DFT (time-dependent density functional theory) and "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO energy level and the LUMO energy level are calculated according to the following calibration formula, and the S1 energy level and the T1 energy level are used directly.

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

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

[0404] Among them, HOMO, LUMO, T1 and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree.

[0405] Table 1 Calculation results of HOMO energy levels of organic compounds

[0406]

[0407]

[0408] From the results in Table 1, it can be seen that the T1 energy level and S1 energy level of the organic compounds M1 to M25 provided in Examples 1 to 25 of the present application are higher than the T1 energy level and S1 energy level of the comparative compound 1. This further indicates that compared with the comparative compound 1, the blue light emitted by the organic compounds M1 to M25 provided in the examples of the present application is more inclined to dark blue, which is beneficial for the blue organic light-emitting device using the organic compounds M1 to M25 as the guest material in the light-emitting layer to obtain better color coordinates.

[0409] For further information, please refer to Figure 4 , the embodiments of the present application provide Figure 4 The exemplary manufacturing steps of the organic light-emitting device 100 are shown in the following exemplary embodiment 1.

[0410] Example 1

[0411] In the organic light-emitting device provided in this embodiment, ITO (indium tin oxide) is used as the anode 101, PEDOT (polyethylene dioxythiophene, Clevios TM AI4083) is used as the material of the hole injection layer 104, PVK (poly (9-vinyl carbazole, Sigma Aldrich, average Mn 25,000-50,000) is used as the material of the hole transport layer 105, BH-1 to BH-3 (whose structural formulas are shown below) are respectively used as the host materials in the light-emitting layer 107 of the corresponding organic light-emitting device, the organic compounds M1 to M25 in Examples 1 to 29 and the comparative compound 1 in Comparative Example 1 are respectively used as the guest materials in the light-emitting layer 107 of the corresponding organic light-emitting device, ET and Liq (8-hydroxyquinoline lithium) are used as the materials of the electron transport layer 108, and Al is used as the cathode 102. The specific preparation steps are as follows:

[0412] a. Cleaning of the ITO anode 101: using chloroform, acetone and / or isopropyl alcohol to clean the ITO conductive glass, and then performing ultraviolet ozone treatment;

[0413] b. Forming the hole injection layer 104: Spin-coating the hole injection layer material PEDOT (polyethylene dioxythiophene, Clevios TM AI4083), and treated on a hot plate at 180°C for 10 minutes, the thickness of the hole injection layer 104 is 40 nm;

[0414] c. Forming the hole transport layer 105: Spin-coating a toluene solution of PVK (Sigma Aldrich, Mn 25,000-50,000) with a concentration of 5 mg / ml on the hole injection layer 104, and then treating on a hot plate at 180° C. for 60 minutes. The thickness of the hole transport layer 105 is 20 nm.

[0415] d. Forming the light-emitting layer 107: In a nitrogen glove box, spin-coating the light-emitting layer 107 material on the hole transport layer 105, and then treating it on a hot plate at 140° C. for 10 minutes, the main material in the light-emitting layer 107 of different organic light-emitting devices corresponds to BH-1, BH-2 or BH-3, respectively, and the guest material in the light-emitting layer 107 of different organic light-emitting devices corresponds to one of organic compounds M1 to organic compounds M25, respectively, the solvent is methyl benzoate solution, the mass ratio of the main material to the guest material is 95:5, the concentration of the material of the light-emitting layer 107 is 15 mg / ml, and the thickness of the light-emitting layer 107 finally formed is 40 nm.

[0416] e. Forming the electron transport layer 108: In a vacuum chamber, on the light-emitting layer 107, ET and Liq are placed in different evaporation units and heated in a high vacuum (1×10 -6 ET and Liq are co-deposited at a weight ratio of 50:50 in an environment of 200 mbar to form an electron transport layer 108 with a thickness of 20 nm;

[0417] f. Forming the cathode layer 102: depositing Al on the electron transport layer 108 to obtain an Al cathode 102 with a thickness of 100 nm;

[0418] g. Packaging: The device is packaged with UV-curable resin in a nitrogen glove box.

[0419] Specifically, in this embodiment, the above steps are used to obtain organic light-emitting devices 1 to 27 and comparative elements 1 to 3. Among them, the guest materials used in the organic light-emitting devices 1 to 25 are organic compounds M1 to M25, respectively, and the host material used in the organic light-emitting devices 1 to 25 is BH-1; the guest material used in the organic light-emitting devices 26 and 28 is organic compound M1, and the host materials used in the organic light-emitting devices 26 and 28 are BH-2 and BH-3, respectively; the guest material used in the organic light-emitting devices 27 and 29 is organic compound M18, and the host materials used in the organic light-emitting devices 27 and 29 are BH-2 and BH-3, respectively; the guest material used in the comparative elements 1 to 3 is comparative compound 1, and the host materials used in the comparative elements 1 to 3 are BH-1, BH-2 and BH-3, respectively.

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

[0421]

[0422] In this embodiment, the current-voltage (JV) characteristic test was performed on the organic light-emitting devices 1 to 29 and the comparative elements 1 to 3, and the CIE color coordinates (x, y), the driving voltage at 1 knits brightness (voltage @ 1 knits [V]), and the current density of 10 mA / cm 2 The luminous efficiency (CE@1knits[cd / A]) obtained when the luminance is reduced from the initial brightness of 1knits to 90% of the initial brightness (LT90@1knits[h]) is shown in Table 2.

[0423] Table 2 Performance data of organic light-emitting devices

[0424]

[0425]

[0426] As can be seen from Table 2, the organic light-emitting devices 1 to 29 of the present application using guest materials M1 to M25 in the light-emitting layer have better color coordinates than the comparative elements 1 to 3; further, the luminous efficiency of the organic light-emitting devices 1 to 29 is 5.7-6.4 cd / A, indicating that the luminous efficiency is much higher than the luminous efficiency of the comparative elements 1 to 3; further, the time taken for the brightness of the organic light-emitting devices 1 to 29 to decrease from the initial brightness of 1 knits to 90% of the initial brightness is in the range of 129-183 h, compared with the time taken for the brightness of the comparative elements 1 to 3 to decrease from the initial brightness of 1 knits to 90% of the initial brightness, the improvement is 50% to 100%, indicating that the organic light-emitting devices 1 to 29 have a significantly improved lifespan.

[0427] At the same time, compared with Comparative Example 1, the organic compounds M1 to M25 introduce large groups (alkyl silicon groups, dibenzofuran groups) into the hydrazine of the boron nitrogen compound benzothiophene, or introduce triphenylsilicon, indenecarbazole, indolecarbazole groups, fluorenecarbazole, triazine, dicarbazolylphenyl, 2,6-diphenylphenyl and multiple C1-C4 alkyl groups into the para position of boron, so that the overall molecular solubility is better and the compound purification is easy, thereby improving the purity of the compound and further improving the efficiency and life of the manufactured organic light-emitting device.

[0428] In addition, the organic light-emitting devices 1-4, 20-25 are in the range of 6.1 to 6.5 cd / A, and their lifespans are all around 180 h. This is because compared with the guest materials in other organic light-emitting devices, the introduction of large groups, namely silicon groups and carbazole groups, into the hydrazine of the boron nitrogen compound benzothiophene improves the solubility and hole conduction capability of the guest material, and further improves the luminous efficiency and lifespan of the organic light-emitting device.

[0429] The organic light-emitting device disclosed in the embodiments of the present application improves material properties, improves the luminous efficiency of the organic light-emitting device and prolongs the service life of the organic light-emitting device by using boron nitrogen compounds and introducing biphenyl + benzothiophene aromatic amines and silicon-containing groups that make the overall conjugation of the compound greater, or introducing triphenylsilicon, indenecarbazole, indolecarbazole groups, fluorenecarbazole, triazine, dicarbazolylphenyl, 2,6-diphenylphenyl, phenyl and poly-C1-C4 alkyl groups at the para position of boron.

[0430] The embodiment of the present application further discloses a display panel, which includes the organic light-emitting device described in the above embodiment.

[0431] In some embodiments, the display panel may further include an array substrate located on one side of the organic light-emitting device, and an encapsulation layer located on a side of the organic light-emitting device away from the array substrate and covering the organic light-emitting device. The display panel also includes a polarizer layer located on a side of the encapsulation layer away from the organic light-emitting device, and a cover layer located on a side of the polarizer layer away from the organic light-emitting device.

[0432] In some embodiments, the polarizer layer may be replaced by a color filter layer, and the color filter layer may include a plurality of color resists and a black matrix located on both sides of the color resists.

[0433] The display panel disclosed in the embodiment of the present application uses an organic light-emitting device containing a boron nitrogen compound, and introduces a silicon-containing group and a poly-C1-C4 alkyl group into the boron nitrogen compound to make the overall conjugation of the compound greater, thereby enhancing the conjugation effect of the material used in the organic light-emitting device, improving the material performance, improving the luminous efficiency of the display panel and extending the service life of the display panel.

[0434] In the above embodiments, the description of each embodiment has its own emphasis. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0435] The above is a detailed introduction to an organic compound, a mixture, a composition, an organic light-emitting device and a display panel provided in the embodiments of the present application. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the technical solution and its core idea of ​​the present application. Ordinary technicians in this field should understand that they can still modify the technical solutions recorded in the aforementioned embodiments, or make equivalent replacements for some of the technical features therein; and these modifications or replacements do not make the essence of the corresponding technical solution deviate from the scope of the technical solution of the embodiments of the present application.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in general formula (1): Wherein, Ar1 is selected from the group represented by any one of formula (A-1) to formula (A-7); Ar2 is selected from the group represented by any one of formula (B-1) to formula (B-10): X is selected from O, S, N-CH3, N-Ph or C(CH3)2; n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; R0 is selected from an alkyl group having 1 to 4 carbon atoms or an Ar1 group or an Ar2 group, and R0 can also be combined with the benzene ring to form an Ar1 group or an Ar2 group; n0 is selected from 1, 2 or 3; R1 is selected from H, D, a linear alkyl group having 1 to 20 carbon atoms, a linear silicon group having 1 to 20 carbon atoms, a branched silicon group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a trimethylsilyl group, a triphenylsilyl group, a carbon atom the ketone group having 1 to 20 carbon atoms, the alkoxycarbonyl group having 2 to 20 carbon atoms, the aryloxycarbonyl group having 7 to 20 carbon atoms, the olefin group having 1 to 20 carbon atoms, CN, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms.

2. The organic compound according to claim 1, characterized in that Ar2 is selected from the group represented by any one of the formulas (B-9) to (B-10); When Ar2 is selected from the group represented by the formula (B-10), Ar1 is selected from the group represented by any one of the formulas (A-1) to (A-7).

3. The organic compound according to claim 1, characterized in that R0 is selected from an alkyl group having 1 to 4 carbon atoms, and n0 is selected from 1, 2 or 3.

4. The organic compound according to claim 1, characterized in that R1 is selected from H, D, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, and a cyclic alkyl group having 3 to 10 carbon atoms.

5. The organic compound according to claim 1 or 4, characterized in that R1 is selected from H, D, a linear alkyl group having 1 to 4 carbon atoms, and a branched alkyl group having 3 to 5 carbon atoms.

6. The organic compound according to claim 1, characterized in that When Ar1 is a group represented by the formula (A-2), the group represented by the formula (B-2) is selected from: as well as At least one of .

7. The organic compound according to claim 1, characterized in that The organic compound is a blue light emitting material.

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

9. A mixture, characterized in that The mixture comprises the organic compound according to any one of claims 1 to 8 and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes.

10. A composition, characterized in that The composition comprises the organic compound according to any one of claims 1 to 8 and at least one organic solvent, or the composition comprises the mixture according to claim 9 and at least one organic solvent.

11. An organic light-emitting device, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; as well as an organic functional layer, located between the first electrode and the second electrode; The material of the organic functional layer comprises one or more of the organic compounds described in any one of claims 1 to 8, or the material of the organic functional layer comprises the mixture described in claim 9, or the material of the organic functional layer comprises the composition described in claim 10.

12. The organic light emitting device according to claim 11, characterized in that: The organic functional layer includes a light-emitting layer, and the material of the light-emitting layer includes a host material and a guest material, and the guest material includes one or more of the organic compounds.

13. The organic light emitting device according to claim 12, characterized in that: The mass ratio of the host material to the guest material ranges from 99:1 to 70:

30.

14. A display panel, characterized in that: The display panel comprises the organic light emitting device according to any one of claims 11 to 13.

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