Organic compound, organic light-emitting device and display panel

Abstract

The invention relates to an organic compound, an organic light-emitting device and a display panel, the chemical structural formula of the organic compound is as shown in the formula M: # imgabs0, the organic compound can be used as a light-emitting material to be applied to the organic light-emitting device, the light-emitting efficiency of the organic light-emitting device can be improved, and the service life of the organic light-emitting device can be prolonged.

Description

Technical Field

[0001] The present application relates to the field of display technology, and in particular to an organic compound, 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, an electron injection layer, etc. 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 a 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 prior art 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 the difficulty in improving the luminous efficiency and service life of organic electroluminescent elements using organic compounds with TADF. Therefore, there is an urgent need for an organic compound for organic light-emitting devices to solve the above technical problems. Summary of the invention

[0005] The embodiments of the present application provide an organic compound, an organic light-emitting device and a display panel. The organic compound can be used as a light-emitting material in the organic light-emitting device to improve the light-emitting efficiency and service life of the organic light-emitting device.

[0006] In order to achieve the above object, according to the first aspect of the present application, an organic compound is provided, and the chemical structural formula of the organic compound is shown in Formula M:

[0007]

[0008] wherein Ar1 is selected from 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;

[0009] Ar2 is selected from a substituted or unsubstituted aromatic group having 6 ring atoms;

[0010] R1 is selected from -H, -D, a linear alkyl group having 1 to 20 carbon atoms, a linear or 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 ketone group having 1 to 20 carbon atoms The invention also comprises any one or more combinations of: -C1, -Br, -F, -C2, -C1, -Br, -F, -C1, -C2, -C12, -C13, -C14, -C15, -C16, -C17, -C18, -C19, -C20, -C21, -C22, -C23, -C24, -C25, -C26, -C27, -C28, -C29, -C29, -C21, -C22, -C23, -C24, -C29, -C29, -C21, -C22, -C23, -C24, -C25, -C26, -C29 ...

[0011] According to a second aspect of the present application, an organic light-emitting device is provided, the organic light-emitting device comprising a first electrode, a second electrode and an organic functional layer; the second electrode is arranged opposite to the first electrode, and the organic functional layer is located between the first electrode and the second electrode;

[0012] Wherein, the material of the organic functional layer includes at least one of the organic compounds mentioned above.

[0013] According to a third aspect of the present application, a display panel is also provided, comprising the organic light-emitting device described above.

[0014] In the organic compound, organic light-emitting device and display panel of the embodiment of the present application, a seven-membered ring spirofluorene structure that increases the overall conjugation of the organic compound is introduced into the boron nitrogen compound, and then a boron nitrogen compound containing a seven-membered ring spirofluorene group, a carbazole group and a pyrrole group is formed (i.e., an organic compound represented by Formula M). Since the seven-membered ring structure has a large planar structure, the organic compound is easier to purify, which is beneficial to improve the purity of the organic compound, and further improves the luminous efficiency and service life of the organic light-emitting device using the seven-membered ring structure.

[0015] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] 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.

[0017] Figure 1 is a schematic structural diagram of an organic light-emitting device provided in an embodiment of the present application;

[0018] Figure 2 It is a schematic diagram of the structure of another organic light-emitting device provided in an embodiment of the present application.

[0019] Figure numerals: 100, organic light-emitting device; 110, substrate; 101, first electrode layer (anode); 102, second electrode layer (cathode); 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

[0020] The present application provides an organic compound, 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, and the description order of the following embodiments is not used as a limitation on the preferred order of the embodiments.

[0021] Unless otherwise defined, all terms (including technical and scientific terms) used in this document have the same meaning as commonly understood by one of ordinary skill in the art 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 having a meaning consistent with their meaning 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 so defined herein.

[0022] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0023] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0024] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] 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, and each occurrence may be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 2-Hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-tridecyl, 2-tetradecyl, 2-pentadecyl, 2-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-octadecyl, 2-octadecyl, 2-nonadecyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, 2-heneicosyl, 2-heneicosyl, 2-heconicosyl, 2-docosyl, 2-tricosyl, 2-tetracosyl, 2-pentacosyl, 2-hexacosyl, 2-heptacosyl, 2-octacosyl, 2-nonacosyl, 2-triacontyl, etc.

[0031] 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, ph-phenyl.

[0032] In the present application, "amino" refers to an amine derivative having the structural characteristics of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amines include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0033] 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.

[0034] 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.

[0035] In the present application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (wherein Z represents a halogen (e.g., F, Cl, Br or I)), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0036] In the present application, the term "alkoxy" refers to a group having a structure of "-O-alkyl", i.e., an alkyl group as defined above is connected to other groups via an oxygen atom. Phrases containing the term, suitable examples include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-OC(CH3)3 or -OtBu).

[0037] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0043] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0044] In the present application, "two adjacent R1 or two adjacent R3 or two adjacent R5 form a ring with each other" means a ring system formed by two adjacent R1 or two adjacent R3 or two adjacent R5 connected to each other, and the ring system can be selected from aliphatic hydrocarbon ring, aliphatic heterocycle, aromatic hydrocarbon ring or aromatic heterocycle. Preferably,

[0045] The present application embodiment provides an organic compound, the chemical structure of the organic compound is shown in Formula M:

[0046]

[0047] wherein Ar1 is selected from 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;

[0048] Ar2 is selected from a substituted or unsubstituted aromatic group having 6 ring atoms;

[0049] R1 is selected from -H, -D, a linear alkyl group having 1 to 20 carbon atoms, a linear or 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 ketone group having 1 to 20 carbon atoms The invention also comprises any one or more combinations of: -C1, -Br, -F, -C2, -C1, -Br, -F, -C1, -C2, -C12, -C13, -C14, -C15, -C16, -C17, -C18, -C19, -C20, -C21, -C22, -C23, -C24, -C25, -C26, -C27, -C28, -C29, -C29, -C21, -C22, -C23, -C24, -C29, -C29, -C21, -C22, -C23, -C24, -C25, -C26, -C29 ...

[0050] In some embodiments, R1 is selected from any one or more of -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.

[0051] In some embodiments, R1 is selected from any one or more combinations of -H, -D, a linear alkyl group having 1 to 4 carbon atoms, and a branched alkyl group having 3 to 5 carbon atoms.

[0052] In some embodiments, the R1 is selected from -H, -D, a straight chain alkyl group having 1 to 14 carbon atoms, a branched chain alkyl group having 1, 6, 12 or 14 carbon atoms.

[0053] 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.

[0054] In some embodiments, two adjacent R1s are mutually cyclic; further, two adjacent R1s are mutually cyclic to form a 6-membered aromatic ring or aliphatic ring; further, two adjacent R1s are mutually cyclic to form Wherein, * indicates the connection site.

[0055] In some embodiments, Ar1 is selected from any one of the following structures:

[0056]

[0057] wherein V is selected from CR7 or N;

[0058] W is selected from NR8, CR8R9, SiR8R9, O, S, S=O or SO2;

[0059] R7, R8 and R9 are selected from -H, -D, or a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, a 2 to 20 C atom The invention also includes any one or more combinations of alkoxycarbonyl having 7 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, substituted or unsubstituted aryloxy groups having 5 to 60 ring atoms, and substituted or unsubstituted heteroaryloxy groups having 5 to 60 ring atoms.

[0060] In some embodiments, Ar2 is selected from an aromatic group having 6 ring atoms substituted by a phenyl group or an alkyl group having 1 to 5 carbon atoms.

[0061] In some embodiments, the organic compound is selected from any one of the following compounds:

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069] It can be understood that the organic compound represented by formula M provided in the embodiments of the present application is not limited to the structures listed above, and these structures can be arbitrarily substituted.

[0070] The aromatic amine organic compound shown in Formula M provided in the embodiment of the present application can be used as an organic functional material in the organic functional layer of an electronic device. The organic functional layer includes but is not limited to a hole injection layer (HIL), a hole transport layer (HTL), an electron injection layer (EIL), an electron transport layer (ETL), a prime layer, a hole blocking layer (HBL) and an emission material layer (EML).

[0071] In some embodiments, the organic compound described in the embodiments of the present application is used in a light-emitting layer of an electronic device.

[0072] In a specific embodiment, the material of the light-emitting layer includes a host material and a guest material, and the guest material includes at least one organic compound represented by Formula M.

[0073] In some embodiments, the organic compound is a TADF material.

[0074] In a specific embodiment, the guest material is a green light material, that is, the light-emitting layer emits green light.

[0075] It is understandable that the organic compounds provided in the embodiments of the present application are not limited to green light guest materials.

[0076] The organic compound provided in the embodiment of the present application is a boron-nitrogen organic compound, and structures such as seven-membered ring spirofluorene, dibenzofuran, dibenzothiophene, carbazole, benzopentacyclic ring, triphenylene and / or naphthalene are introduced into the boron-nitrogen compound, so that the overall molecular conjugation of the organic compound is greater, and the luminous efficiency and service life of the organic light-emitting device using the organic compound are improved. At the same time, the introduction of structures such as tetralin and / or indane into the boron-nitrogen compound makes the molecule more soluble in processes such as inkjet printing, and is easy to purify the organic compound, which is beneficial to improve the purity of the organic compound, and further improves the luminous efficiency and service life of the organic light-emitting device using the organic compound.

[0077] The embodiment of the present application also provides a polymer, wherein the monomer of the polymer includes an organic compound represented by formula M.

[0078] The present application also provides a mixture, the mixture comprising at least one of the organic compounds described above and at least one organic functional material. The organic functional material is selected from at least one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes.

[0079] like Figure 1 and Figure 2 As shown, the embodiment of the present application further provides an organic light-emitting device 100, the organic light-emitting device 100 includes a first electrode 101, a second electrode 102 arranged opposite to the first electrode 101, and an organic functional layer 103 located between the first electrode 101 and the second electrode 102. The material of the organic functional layer 103 includes at least one of the organic compounds described above, or the organic functional layer 103 is made of the mixture described above.

[0080] In a specific embodiment, the first electrode 101 is an anode, and correspondingly, the second electrode 102 is a cathode.

[0081] In some embodiments, the organic light-emitting device 100 can be used for organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors (OLEFETs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPEDs). Preferably, the organic electronic device is an organic electroluminescent device, such as an OLED, an OLEEC, or an OLEFET.

[0082] 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.

[0083] 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, wherein the first compound is selected from one or more of the organic compounds represented by the above formula M, 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. For detailed descriptions of various organic functional materials included in the organic functional layer 103, see WO2010135519A1, US20090134784A1, and WO 2011110277A1, and the entire contents of these three patent documents are incorporated herein by reference.

[0084] In some embodiments, the light-emitting guest material is selected from a singlet light emitter (fluorescent light emitter), a triplet light emitter (phosphorescent light emitter), and a TADF material.

[0085] When the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, luminescent host materials, and organic dyes, the mass ratio of the first compound to the second compound is in the range of 1:99 to 30:70. Preferably, the mass ratio of the first compound to the second compound is in the range of 1:99 to 10:90.

[0086] When the second compound is a luminescent guest material, the mass ratio of the first compound to the second compound is in the range of 99:1 to 70:30. Preferably, the mass ratio of the first compound to the second compound is in the range of 99:1 to 90:10.

[0087] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 includes multiple layers, the organic functional layer 103 includes at least a light emitting layer 107 .

[0088] In a specific embodiment, Figure 1 As shown, the organic functional layer 103 includes a hole injection layer 104 , a hole transport layer 105 , a light emitting layer 107 and an electron transport layer 108 .

[0089] In another specific embodiment, Figure 2 As shown, the organic functional layer 103 includes a hole injection layer 104 , a hole transport layer 105 , an electron blocking layer 106 , a light emitting layer 107 , an electron transport layer 108 , and an electron injection layer 109 .

[0090] 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.

[0091] In some embodiments, the light emitting wavelength range of the organic light emitting device 100 is 300nm to 1000nm; further, the light emitting wavelength range of the organic light emitting device 100 is between 350nm and 900nm; further, the light emitting wavelength range 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 green light.

[0092] In a specific embodiment, the organic light-emitting device 100 is a green organic light-emitting device, and the light-emitting layer 107 may include a host material and a guest material, and the guest material is one or more organic compounds represented by the above formula M. It can be understood that, at this time, the organic compound represented by formula M is a green light guest material.

[0093] In some embodiments, the host material includes a fused aromatic derivative or a heteroaromatic compound.

[0094] In a specific embodiment, the host material includes at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, triazine derivatives, and pyrimidine derivatives. Preferably, the host material is a green light host material used in green organic light-emitting devices; when the host material is a green light host material, the host material is preferably an anthracene organic compound.

[0095] In some embodiments, the mass ratio of the host material to the guest material ranges from 99:1 to 70:30. For example, the mass ratio of the host material to the guest material is 90:10, 85:15, 80:20, 75:25. Preferably, the mass ratio of the host material to the guest material ranges from 99:1 to 90:10, for example, the mass ratio of the host material to the guest material is 97:3, 96:4, 95:5, 93:7, 92:8.

[0096] 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 beneficial to inhibiting the crystallization of the light-emitting layer 107 and inhibiting concentration quenching of the guest material due to high concentration, thereby improving the luminescence efficiency of the organic light-emitting device 100.

[0097] In some embodiments, the first electrode (anode) 101 is an electrode for injecting holes, and the first electrode 101 can inject holes into the organic functional layer 103, such as: the first electrode 101 injects holes into the hole injection layer, the hole transport layer or the light emitting layer. The first electrode 101 may include at least one of a conductive metal, a conductive metal oxide, and a conductive polymer. Preferably, the work function of the first electrode 101 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 first electrode 101 includes but is not limited to at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), or other suitable and known anode materials, which can be easily selected and used by a person skilled in the art. The material of the first electrode 101 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 first electrode 101 can be patterned, such as a patterned ITO conductive substrate, which is commercially available and can be used to prepare the organic light-emitting device 100 of the present application.

[0098] In some embodiments, the cathode of the second electrode (cathode) 102 is an electrode for injecting electrons, and the second electrode 102 can inject electrons into the organic functional layer, such as: the second electrode 102 injects electrons into the electron injection layer, the electron transport layer, and the light-emitting layer. The second electrode 102 may include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the second electrode 102 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, and 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 is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes of organic electronic devices may be used as cathode materials of the organic light-emitting device of the present application, and the material of the second electrode 102 includes but is not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO. The material of the second electrode 102 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, etc.

[0099] In some embodiments, the hole injection layer 104 is used to promote the injection of holes from the first electrode 101 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 first electrode 101 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 first electrode 101 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 first electrode 101. 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.

[0100] 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 first electrode 101 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.

[0101] In some embodiments, the electron transport layer 108 is used to transport electrons, and the electron transport layer 108 includes an electron transport material, and the electron transport material receives the electrons injected from the second electrode 102 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.

[0102] 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.

[0103] In some embodiments, the hole blocking layer is used to block holes from reaching the second electrode 102, 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.

[0104] In some embodiments, the organic light-emitting device 100 also 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 stacked in sequence on the substrate 110.

[0105] 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. 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 first electrode 101 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). 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.

[0106] 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 (such as inkjet printing).

[0107] 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, pad printing, slit extrusion coating, etc. Preferably, the mixture layer or the luminescent layer is formed by gravure printing, nozzle printing or inkjet printing.

[0108] The composition may be a solution or a suspension, and 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, and the dispersant is used to disperse the dispersant.

[0109] In the composition, the mass fraction of the organic compound as described above ranges from 0.3% to 30%, preferably from 0.5% to 20%, more preferably from 0.5% to 15%, further preferably from 0.5% to 10%, and most preferably from 1% to 5%.

[0110] For example, in the composition, the mass fraction of the organic compound represented by formula M is 0.3%, 0.5%, 0.8%, 1%, 2%, 5%, 8%, 10%, 12%, 15%, 18%, 20%, 22%, 25%, 28% or 30%.

[0111] 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 from 22 dyne / cm to 35 dyne / cm; more preferably from 25 dyne / cm to 33 dyne / cm, which is advantageous for application in an inkjet printing process.

[0112] In some embodiments, the viscosity of the ink at working temperature or 25° C. ranges from 1 cps to 100 cps; preferably from 1 cps to 50 cps; more preferably from 1.5 cps to 20 cps; and most preferably from 4.0 cps to 20 cps, which is advantageous for application in inkjet printing processes.

[0113] In some embodiments, the Hansen solubility parameter of the dispersant is within the following range: the δd (dispersion force) of the dispersant is between 17.0 and 23.2 MPa. 1 / 2 The range is preferably 18.5 to 21.0 MPa 1 / 2 Range; δp (polar force) is 0.2~12.5MPa 1 / 2 The range is preferably 2.0 to 6.0 MPa. 1 / 2 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.

[0114] 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 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.

[0115] The dispersant includes at least one organic solvent, and the organic solvent can be evaporated from the solvent system to form a film containing a functional material.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] 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.

[0120] 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.

[0121] 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.

[0122] 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.

[0123] The present application will be described below in conjunction with preferred embodiments, but the present application is not limited to the embodiments described below. It should be understood that the attached claims summarize the scope of the present application. Under the guidance of the concept of the present invention, those skilled in the art should realize that certain changes made to the various embodiments of the present application will be covered by the spirit and scope of the claims of the present application. Specific embodiments

[0125] The organic compound and the preparation method thereof of the present application are further described in detail below in combination with Examples 1 to 12.

[0126] Example 1

[0127] The synthetic route of organic compound M1 is as follows:

[0128]

[0129]

[0130] Synthesis of intermediate 1-3:

[0131] Compound 1-1 (10 mmol), compound 1-2 (10 mmol), Pd(PPh3)2Cl2 (0.1 mmol), CuI (0.2 mmol) and Et3N (30 mmol) were dissolved in tetrahydrofuran (THF), and the reaction solution was heated to 80°C under a nitrogen atmosphere and stirred for 12 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction was performed and the liquid was washed with water, and the intermediate 1-3 was obtained by organic phase column chromatography with a molar weight of 8.17 mmol and a yield of 81.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-3 was: MS (ASAP) = 290.

[0132] Synthesis of intermediate 1-5:

[0133] Intermediate 1-3 (10 mmol), compound 1-4 (10 mmol), Pd(OAc)2 (0.1 mmol), TTBP (tricyclohexylphosphine, 0.2 mmol) and potassium carbonate (30 mmol) were dissolved in N-methyl-2-pyrrolidone (NMP), and the reaction solution was heated to 110°C and stirred for 5 h under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 1-5 was obtained by organic phase column chromatography 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 1-5 was: MS (ASAP) = 431.

[0134] Synthesis of intermediate 1-8:

[0135] Compound 1-6 (10 mmol), compound 1-7 (10 mmol), and cesium carbonate (50 mmol) were dissolved in N,N-dimethylformamide (DMF), and the reaction solution was heated to 140°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the intermediate 1-8 was obtained by organic phase column chromatography, with a molar weight of 8.63 mmol and a yield of 86.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-8 was: MS (ASAP) = 485.

[0136] Synthesis of intermediate 1-9:

[0137] Intermediate 1-5 (10 mmol), intermediate 1-8 (10 mmol), and cesium carbonate (50 mmol) were dissolved in DMF, and the reaction solution was heated to 140° C. and stirred for 6 h under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. Intermediate 1-9 was obtained by organic phase column chromatography, with a molar weight of 8.25 mmol and a yield of 82.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-9 was: MS (ASAP) = 896.

[0138] Synthesis of intermediate 1-11:

[0139] In a double-necked flask, under nitrogen atmosphere, the intermediate 1-9 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 1-10 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 1-9 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, and then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as a developing solvent to obtain an intermediate 1-11 with a molar weight of 7.59 mmol and a yield of 75.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 1-11 was: MS (ASAP) = 980.

[0140] It should be noted that in the chemical synthesis method described in the present application, M is an abbreviation for mol / L, so 1M represents 1 mol / L.

[0141] Synthesis of organic compound M1:

[0142] In a 250 ml three-necked flask, 10 mmol of intermediate 1-11 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30°C in a nitrogen atmosphere. A n-hexane solution of tert-butyl lithium (t-BuLi) (21 mmol) was added dropwise. The temperature was raised to 60°C for reaction for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30°C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120° C. with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M1, with a yield of 37.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M1 is: MS (ASAP) = 954.

[0143] Example 2

[0144] The synthetic route of organic compound M2 is as follows:

[0145]

[0146] Synthesis of intermediate 2-2:

[0147] Intermediate 1-3 (10 mmol), compound 2-1 (10 mmol), Pd(OAc)2 (0.1 mmol), TTBP (tricyclohexylphosphine, 0.2 mmol) and potassium carbonate (30 mmol) were dissolved in NMP, and the reaction solution was heated to 110°C under a nitrogen atmosphere and stirred for 5 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 2-2 was obtained by organic phase column chromatography with a molar weight of 7.89 mmol and a yield of 78.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-2 was: MS (ASAP) = 381.

[0148] Synthesis of intermediate 2-3:

[0149] Intermediate 2-2 (10 mmol), intermediate 1-8 (10 mmol), and cesium carbonate (50 mmol) were dissolved in DMF, and the reaction solution was heated to 140°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction was performed and the liquid was washed with water, and the intermediate 2-3 was obtained by organic phase column chromatography, 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 2-3 was: MS (ASAP) = 846.

[0150] Synthesis of intermediate 2-4:

[0151] In a double-necked flask, under nitrogen atmosphere, the intermediate 2-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 1-10 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 2-3 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, and then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as a developing solvent to obtain an intermediate 2-4 with a molar weight of 7.34 mmol and a yield of 73.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 2-4 was: MS (ASAP) = 930.

[0152] Synthesis of organic compound M2:

[0153] In a 250 ml three-necked flask, 10 mmol of intermediate 2-4 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M2, with a yield of 41.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M2 is: MS (ASAP) = 904.

[0154] Example 3

[0155] The synthetic route of organic compound M3 is as follows:

[0156]

[0157] Synthesis of intermediate 3-2:

[0158] Intermediate 1-3 (10 mmol), compound 3-1 (10 mmol), Pd(OAc)2 (0.1 mmol), TTBP (tricyclohexylphosphine, 0.2 mmol) and potassium carbonate (30 mmol) were dissolved in NMP, and the reaction solution was heated to 110°C under a nitrogen atmosphere and stirred for 5 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 3-2 was obtained by organic phase column chromatography with a molar weight of 8.63 mmol and a yield of 86.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 3-2 was: MS (ASAP) = 431.

[0159] Synthesis of intermediate 3-3:

[0160] Intermediate 3-2 (10 mmol), intermediate 1-8 (10 mmol), and cesium carbonate (50 mmol) were dissolved in DMF, and the reaction solution was heated to 140°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 3-3 was obtained by organic phase column chromatography, with a molar weight of 8.14 mmol and a yield of 81.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 3-3 was: MS (ASAP) = 896.

[0161] Synthesis of intermediate 3-4:

[0162] In a double-necked flask, under nitrogen atmosphere, the intermediate 3-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 1-10 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 3-3 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated, and the compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as a developing solvent to obtain an intermediate 3-4 with a molar weight of 7.53 mmol and a yield of 75.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 3-4 was: MS (ASAP) = 980.

[0163] Synthesis of organic compound M3:

[0164] In a 250 ml three-necked flask, 10 mmol of intermediate 3-4 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M3, with a yield of 39.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M3 is: MS (ASAP) = 954.

[0165] Example 4

[0166] The synthetic route of organic compound M4 is as follows:

[0167]

[0168] Synthesis of intermediate 4-2:

[0169] Intermediate 1-3 (10 mmol), compound 4-1 (10 mmol), Pd(OAc)2 (0.1 mmol), TTBP (tricyclohexylphosphine, 0.2 mmol) and potassium carbonate (30 mmol) were dissolved in NMP, and the reaction solution was heated to 110°C and stirred for 5 h under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated, and the intermediate 4-2 was obtained by organic phase column chromatography, 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 4-2 was: MS (ASAP) = 481.

[0170] Synthesis of intermediate 4-3:

[0171] Intermediate 4-2 (10 mmol), intermediate 1-8 (10 mmol), and cesium carbonate (50 mmol) were dissolved in DMF, and the reaction solution was heated to 140°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 4-3 was obtained by organic phase column chromatography, with a molar weight of 8.53 mmol and a yield of 85.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 4-3 was: MS (ASAP) = 946.

[0172] Synthesis of intermediate 4-4:

[0173] In a double-necked flask, under nitrogen atmosphere, the intermediate 4-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 1-10 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 4-3 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, and then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as a developing solvent to obtain an intermediate 4-4 with a molar weight of 7.28 mmol and a yield of 72.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 4-4 was: MS (ASAP) = 1030.

[0174] Synthesis of organic compound M4:

[0175] In a 250 ml three-necked flask, 10 mmol of intermediate 4-4 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M4, with a yield of 45.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M4 is: MS (ASAP) = 1004.

[0176] Example 5

[0177] The synthetic route of organic compound M5 is as follows:

[0178]

[0179] Synthesis of intermediate 5-2:

[0180] Intermediate 1-3 (10 mmol), compound 5-1 (10 mmol), Pd(OAc)2 (0.1 mmol), TTBP (tricyclohexylphosphine, 0.2 mmol) and potassium carbonate (30 mmol) were dissolved in NMP, and the reaction solution was heated to 110°C and stirred for 5 h under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated, and the intermediate 5-2 was obtained by organic phase column chromatography, with a molar weight of 8.16 mmol and a yield of 81.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 5-2 was: MS (ASAP) = 481.

[0181] Synthesis of intermediate 5-3:

[0182] Intermediate 5-2 (10 mmol), intermediate 1-8 (10 mmol), and cesium carbonate (50 mmol) were dissolved in DMF, and the reaction solution was heated to 140°C and stirred for 6 hours under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 5-3 was obtained by organic phase column chromatography, with a molar weight of 8.28 mmol and a yield of 82.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 5-3 was: MS (ASAP) = 946.

[0183] Synthesis of intermediate 5-4:

[0184] In a double-necked flask, under nitrogen atmosphere, the intermediate 5-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 1-10 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 5-3 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated, and the compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as a developing solvent to obtain an intermediate 5-4 with a molar weight of 7.03 mmol and a yield of 70.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 5-4 was: MS (ASAP) = 1030.

[0185] Synthesis of organic compound M5:

[0186] In a 250 ml three-necked flask, 10 mmol of intermediate 5-4 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120° C. with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M5, with a yield of 33.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M5 is: MS (ASAP) = 1004.

[0187] Example 6

[0188] The synthetic route of organic compound M6 is as follows:

[0189]

[0190] Synthesis of intermediate 6-2:

[0191] Intermediate 1-3 (10 mmol), compound 6-1 (10 mmol), Pd(OAc)2 (0.1 mmol), TTBP (tricyclohexylphosphine, 0.2 mmol) and potassium carbonate (30 mmol) were dissolved in NMP, and the reaction solution was heated to 110°C and stirred for 5 h under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated, and the intermediate 6-2 was obtained by organic phase column chromatography, with a molar weight of 7.57 mmol and a yield of 75.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 6-2 was: MS (ASAP) = 387.

[0192] Synthesis of intermediate 6-3:

[0193] Intermediate 6-2 (10 mmol), intermediate 1-8 (10 mmol), and cesium carbonate (50 mmol) were dissolved in DMF, and the reaction solution was heated to 140°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 6-3 was obtained by organic phase column chromatography, 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 6-3 was: MS (ASAP) = 852.

[0194] Synthesis of intermediate 6-4:

[0195] In a double-necked flask, under nitrogen atmosphere, the intermediate 6-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 1-10 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 6-3 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, and then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as a developing solvent to obtain an intermediate 6-4 with a molar weight of 7.61 mmol and a yield of 76.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 6-4 was: MS (ASAP) = 936.

[0196] Synthesis of organic compound M6:

[0197] In a 250 ml three-necked flask, 10 mmol of intermediate 6-4 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M6, with a yield of 42.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M6 is: MS (ASAP) = 910.

[0198] Example 7

[0199] The synthetic route of organic compound M7 is as follows:

[0200]

[0201] Synthesis of intermediate 7-2:

[0202] Intermediate 1-3 (10 mmol), compound 7-1 (10 mmol), Pd(OAc)2 (0.1 mmol), TTBP (tricyclohexylphosphine, 0.2 mmol) and potassium carbonate (30 mmol) were dissolved in NMP, and the reaction solution was heated to 110°C under a nitrogen atmosphere and stirred for 5 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 7-2 was obtained by organic phase column chromatography, with a molar weight of 8.34 mmol and a yield of 83.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-2 was: MS (ASAP) = 371.

[0203] Synthesis of intermediate 7-3:

[0204] Intermediate 7-2 (10 mmol), intermediate 1-8 (10 mmol), and cesium carbonate (50 mmol) were dissolved in DMF, and the reaction solution was heated to 140°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 7-3 was obtained by organic phase column chromatography, with a molar weight of 7.63 mmol and a yield of 76.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-3 was: MS (ASAP) = 836.

[0205] Synthesis of intermediate 7-4:

[0206] In a double-necked flask, under nitrogen atmosphere, the intermediate 7-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 1-10 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 7-3 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as the developing solvent to obtain an intermediate 7-4 with a molar weight of 7.27 mmol and a yield of 72.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 7-4 was: MS (ASAP) = 920.

[0207] Synthesis of organic compound M7:

[0208] In a 250 ml three-necked flask, 10 mmol of intermediate 7-4 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M7, with a yield of 48.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M7 is: MS (ASAP) = 894.

[0209] Example 8

[0210] The synthetic route of organic compound M8 is as follows:

[0211]

[0212] Synthesis of intermediate 8-2:

[0213] Intermediate 1-3 (10 mmol), compound 8-1 (10 mmol), Pd(OAc)2 (0.1 mmol), TTBP (tricyclohexylphosphine, 0.2 mmol) and potassium carbonate (30 mmol) were dissolved in NMP, and the reaction solution was heated to 110°C under a nitrogen atmosphere and stirred for 5 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 8-2 was obtained by organic phase column chromatography, with a molar weight of 7.17 mmol and a yield of 71.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 8-2 was: MS (ASAP) = 471.

[0214] Synthesis of intermediate 8-3:

[0215] Intermediate 8-2 (10 mmol), intermediate 1-8 (10 mmol), and cesium carbonate (50 mmol) were dissolved in DMF, and the reaction solution was heated to 140°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 8-3 was obtained by organic phase column chromatography, with a molar weight of 7.46 mmol and a yield of 74.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 8-3 was: MS (ASAP) = 936.

[0216] Synthesis of intermediate 8-4:

[0217] In a double-necked flask, under nitrogen atmosphere, the intermediate 8-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 1-10 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 8-3 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, and then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as a developing solvent to obtain an intermediate 8-4 with a molar weight of 88.3 mmol and a yield of 88.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 8-4 was: MS (ASAP) = 1020.

[0218] Synthesis of organic compound M8:

[0219] In a 250 ml three-necked flask, 10 mmol of intermediate 8-4 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M8, with a yield of 40.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M8 is: MS (ASAP) = 994.

[0220] Example 9

[0221] The synthetic route of organic compound M9 is as follows:

[0222]

[0223] Synthesis of intermediate 9-2:

[0224] Intermediate 1-3 (10 mmol), compound 9-1 (10 mmol), Pd(OAc)2 (0.1 mmol), TTBP (tricyclohexylphosphine, 0.2 mmol) and potassium carbonate (30 mmol) were dissolved in NMP, and the reaction solution was heated to 110°C under a nitrogen atmosphere and stirred for 5 h; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 9-2 was obtained by organic phase column chromatography, with a molar weight of 7.17 mmol and a yield of 71.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-2 was: MS (ASAP) = 546.

[0225] Synthesis of intermediate 9-3:

[0226] Intermediate 9-2 (10 mmol), intermediate 1-8 (10 mmol), and cesium carbonate (50 mmol) were dissolved in DMF, and the reaction solution was heated to 140°C under a nitrogen atmosphere and stirred for 6 hours; after the reaction solution was cooled, the solvent was removed by rotary evaporation, and then extraction and water washing were performed, and the liquid was separated. The intermediate 9-3 was obtained by organic phase column chromatography, with a molar weight of 7.46 mmol and a yield of 74.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-3 was: MS (ASAP) = 1011.

[0227] Synthesis of intermediate 9-4:

[0228] In a double-necked flask, under nitrogen atmosphere, the intermediate 9-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 1-10 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 9-3 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, and then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as a developing solvent to obtain an intermediate 9-4 with a molar weight of 88.3 mmol and a yield of 88.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 9-4 was: MS (ASAP) = 1095.

[0229] Synthesis of organic compound M9:

[0230] In a 250 ml three-necked flask, 10 mmol of intermediate 9-4 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120° C. with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M9, with a yield of 40.5%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M9 is: MS (ASAP) = 1069.

[0231] Example 10

[0232] The synthetic route of organic compound M10 is as follows:

[0233]

[0234]

[0235] Synthesis of intermediate 10-2:

[0236] In a double-necked flask, under nitrogen atmosphere, the intermediate 1-9 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 10-1 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of the intermediate 1-9 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, and then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as a developing solvent to obtain an intermediate 10-2 with a molar weight of 8.56 mmol and a yield of 85.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 10-2 was: MS (ASAP) = 1092.

[0237] Synthesis of organic compound M1:

[0238] In a 250 ml three-necked flask, 10 mmol of intermediate 10-2 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120° C. with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M10, with a yield of 48.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M10 is: MS (ASAP) = 1066.

[0239] Embodiment 11

[0240] The synthetic route of organic compound M11 is as follows:

[0241]

[0242] Synthesis of intermediate 11-2:

[0243] In a double-necked flask, under nitrogen atmosphere, the intermediate 2-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 11-1 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 2-3 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as the developing solvent to obtain an intermediate 11-2 with a molar weight of 8.41 mmol and a yield of 84.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 11-2 was: MS (ASAP) = 990.

[0244] Synthesis of organic compound M11:

[0245] In a 250 ml three-necked flask, 10 mmol of intermediate 11-2 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120° C. with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M11, with a yield of 35.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M11 is: MS (ASAP) = 1016.

[0246] Example 12

[0247] The synthetic route of organic compound M12 is as follows:

[0248]

[0249] Synthesis of intermediate 12-2:

[0250] In a double-necked flask, under nitrogen atmosphere, the intermediate 3-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added, and the reaction was carried out at this temperature for 1 hour. Compound 12-1 (10 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of intermediate 3-3 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as the developing solvent to obtain an intermediate 12-2 with a molar weight of 7.19 mmol and a yield of 71.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of the intermediate 12-2 was: MS (ASAP) = 1008.

[0251] Synthesis of organic compound M12:

[0252] In a 250 ml three-necked flask, 10 mmol of intermediate 3-4 and 100 ml of dry tert-butylbenzene were added. The mixture was cooled to -30 °C in a nitrogen atmosphere. A solution of tert-butyl lithium (21 mmol) in n-hexane was added dropwise. The temperature was raised to 60 °C for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine is completed, the temperature is raised to room temperature with stirring, and the temperature is further raised to 120°C with stirring for 3 hours, and the reaction solution is cooled to room temperature; sodium carbonate aqueous solution and ethyl acetate are added to quench the reaction; the aqueous phase is extracted with ethyl acetate and the organic phases are combined, and the solvent therein is evaporated to obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product; recrystallization is performed with toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M12, with a yield of 44.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound M12 is: MS (ASAP) = 982.

[0253] Comparative Example

[0254] An organic compound Ref is used as a comparative example of the above-mentioned embodiments 1 to 12, and the structural formula of the organic compound Ref is:

[0255]

[0256] As shown in Table 1, the highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, the first excited triplet state (T1) energy level, and the first excited singlet state (S1) energy level of the organic compounds M1 to M12 obtained in Examples 1 to 12 and the organic compound Ref in the comparative example can be obtained by quantum calculation. Specifically, time-dependent density functional theory (TD-DFT) 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.

[0257] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0258] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0259] Among them, HOMO, LUMO, T1 and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree.

[0260] Table 1: Calculation results of HOMO energy level, LUMO energy level, S1 energy level and T1 energy level of organic compounds

[0261] Compound HOMO[eV] LUMO[eV] T1[eV] S1[eV] Example 1 Organic compound M1 -5.18 -2.81 1.79 2.26 Example 2 Organic Compound M2 -5.16 -2.84 1.80 2.25 Example 3 Organic Compound M3 -5.16 -2.81 1.80 2.27 Example 4 Organic Compound M4 -5.09 -2.82 1.83 2.28 Example 5 Organic Compound M5 -5.11 -2.86 1.84 2.28 Example 6 Organic Compound M6 -5.13 -2.89 1.81 2.29 Example 7 Organic Compound M7 -5.13 -2.81 1.83 2.28 Example 8 Organic Compound M8 -5.18 -2.79 1.80 2.27 Example 9 Organic Compound M9 -5.14 -2.81 1.83 2.26 Example 10 Organic Compound M10 -5.14 -2.83 1.86 2.25 Embodiment 11 Organic Compound M11 -5.13 -2.82 1.84 2.21 Example 12 Organic Compound M12 -5.15 -2.83 1.85 2.26 Comparative Example Organic CompoundsRef -5.21 -2.93 1.96 2.41

[0262] It can be seen from Table 1 that the T1 energy level and S1 energy level of the organic compounds M1 to M12 provided in Examples 1 to 12 of the present application are lower than the T1 energy level and S1 energy level of the organic compound Ref provided in the comparative example, which shows that compared with the organic compound Ref, the green light emitted by the organic compounds M1 to M12 is more inclined to dark green, which is conducive to obtaining better color coordinates for green organic light-emitting devices using the organic compounds M1 to M12 as guest materials in the light-emitting layer.

[0263] The exemplary manufacturing steps of the organic light-emitting device 100 provided in the embodiment of the present application are shown in the following exemplary embodiment.

[0264] Exemplary Embodiments

[0265] In the method for preparing an organic light-emitting device provided in the exemplary embodiment of the present application, indium tin oxide (ITO) is used as an anode material, polyethylene dioxythiophene (PEDOT, Clevios TM AI4083) is used as a material for the hole injection layer, poly (9-vinyl carbazole) (PVK, Sigma Aldrich, average Mn 25,000-50,000) is used as a material for the hole transport layer, GH-P and GH-N (whose structural formulas are shown below) are used as host materials in the light-emitting layer of the corresponding organic light-emitting device, the organic compounds M1 to M12 in Examples 1 to 12 and the organic compound Ref in the comparative example are used as guest materials in the light-emitting layer of the corresponding organic light-emitting device, ET and Liq (8-hydroxyquinoline lithium) are used as materials for the electron transport layer, and Al is used as a cathode material.

[0266] The specific preparation steps of the organic light-emitting device are as follows:

[0267] a. Cleaning of ITO anode: Use chloroform, acetone and / or isopropyl alcohol to clean the ITO conductive glass, and then perform UV ozone treatment;

[0268] b. Forming a hole injection layer: spin-coating a hole injection layer material PEDOT on the ITO anode and treating it on a hot plate at 180° C. for 10 minutes to form a hole injection layer with a thickness of 40 nm;

[0269] c. Forming a hole transport layer: Spin-coat a 5 mg / ml PVK toluene solution on the hole injection layer, and then treat on a hot plate at 180° C. for 60 minutes to form a hole transport layer with a thickness of 20 nm;

[0270] d. Forming a light-emitting layer: In a nitrogen glove box, spin-coat the light-emitting layer material on the hole transport layer, and then treat it on a hot plate at 140° C. for 10 minutes. The main materials in the light-emitting layer of the organic light-emitting device are GH-P and GH-N, and the guest materials in the light-emitting layers of different organic light-emitting devices correspond to one of organic compounds M1 to M12, respectively. The solvent is methyl benzoate solution. The mass ratio of GH-P, GH-N and the guest material is 42.5:52.5:5. The concentration of the material of the light-emitting layer is 15 mg / ml, and finally a light-emitting layer with a thickness of 40 nm is formed.

[0271] e. Forming the electron transport layer: In a vacuum chamber, above the light-emitting layer, ET and Liq are placed in different evaporation units and heated to 400 ℃ under high vacuum (1×10-6 ET and Liq were co-deposited at a weight ratio of 50:50 under a 200 mbar (mbar) environment to form an electron transport layer with a thickness of 20 nm;

[0272] f. Forming a cathode layer: depositing Al on the electron transport layer to obtain a cathode made of Al with a thickness of 100 nm;

[0273] g. Packaging: The device is packaged with UV-curable resin in a nitrogen glove box.

[0274] Organic light-emitting devices 1 (OLED-1) to 12 (OLED-12) and a comparative element (OLED-Ref) were obtained through the above steps. The guest materials used by OLED-1 to OLED-12 were organic compounds M1 to M12, respectively, the guest material used by OLED-Ref was organic compound Ref, and the host materials of these organic light-emitting devices were GH-P and GH-N.

[0275] Specifically, the chemical structures of GH-P, GH-N, ET and Liq are as follows:

[0276]

[0277] The present invention tests the current-voltage (JV) characteristics of OLED-1 to OLED-12 and OLED-Ref, and obtains the CIE color coordinates (x, y), the driving voltage at 1knits brightness (voltage @ 1knits [V]), and the current density of 10mA / cm 2 The luminous efficiency (CE@1knits[cd / A]) obtained when the luminance is reduced from the initial brightness of 1knits to 95% of the initial brightness (LT90@1knits[h]) is shown in Table 2.

[0278] Table 2: Performance data of OLED-1 to OLED-12 and OLED-Ref

[0279]

[0280] As can be seen from Table 2, the OLED-1 to OLED-12 obtained by using organic compounds M1 to M12 as guest materials of the light-emitting layer in the present application have better color coordinates than OLED-Ref. Furthermore, the luminous efficiency of OLED-1 to OLED-12 is 170 to 180 cd / A, which is much higher than the luminous efficiency of OLED-Ref. Furthermore, the time taken for the brightness of OLED-1 to OLED-12 to drop from the initial brightness of 1 knits to 95% of the initial brightness is in the range of 780 to 790 h, which is about 150% higher than the time taken for the brightness of OLED-Ref to drop from the initial brightness of 1 knits to 95% of the initial brightness, indicating that the service life of OLED-1 to OLED-12 has been significantly improved.

[0281] At the same time, compared with the organic compound Ref, the organic compounds M1 to M12 introduce a seven-membered ring spirofluorene structure into the boron nitrogen compound to make the overall conjugation of the compound greater, and then form a boron nitrogen compound containing a seven-membered ring spirofluorene group, a carbazole group and a pyrrole group. Since this seven-membered ring has a large planar structure, the overall molecular solubility of the organic compound is better, making the organic compound easier to purify, which is beneficial to improving the purity of the organic compound, and further beneficial to improving the luminous efficiency and service life of the organic light-emitting device using the organic compound.

[0282] An embodiment of the present application further discloses a display panel, which includes any of the above-mentioned organic light-emitting devices.

[0283] The display panel further includes an array substrate located on one side of the organic light-emitting device, and an encapsulation layer located on a side of the organic light-emitting device away from the array substrate and covering the organic light-emitting device. The display panel further 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. 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.

[0284] 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 seven-membered ring spirofluorene structure 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.

[0285] It is understandable that those skilled in the art can make equivalent substitutions or changes based on the technical solution and inventive concept of the present application, and all these changes or substitutions should fall within the protection scope of the claims attached to the present application.

Claims

1. An organic compound, characterized in that The chemical structural formula of the organic compound is shown in Formula M: wherein Ar1 is selected from 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; Ar2 is selected from a substituted or unsubstituted aromatic group having 6 ring atoms; R1 is selected from -H, -D, a linear alkyl group having 1 to 20 carbon atoms, a linear or 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 ketone group having 1 to 20 carbon atoms The invention also comprises any one or more combinations of: -C1, -Br, -F, -C2, -C1, -Br, -F, -C1, -C2, -C12, -C13, -C14, -C15, -C16, -C17, -C18, -C19, -C20, -C21, -C22, -C23, -C24, -C25, -C26, -C27, -C28, -C29, -C29, -C21, -C22, -C23, -C24, -C29, -C29, -C21, -C22, -C23, -C24, -C25, -C26, -C29 ...

2. The organic compound according to claim 1, characterized in that The R1 is selected from any one or more combinations of -H, -D, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, and a cyclic alkyl group having 3 to 10 carbon atoms.

3. The organic compound according to claim 1, characterized in that The R1 is selected from any one or more combinations of -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.

4. The organic compound according to claim 1, characterized in that The Ar1 is selected from any one of the following structures: wherein V is selected from CR7 or N; W is selected from NR8, CR8R9, SiR8R9, O, S, S=O or SO2; R7, R8 and R9 are selected from -H, -D, or a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, a 2 to 20 C atom The invention also includes any one or more combinations of alkoxycarbonyl having 7 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, substituted or unsubstituted aryloxy groups having 5 to 60 ring atoms, and substituted or unsubstituted heteroaryloxy groups having 5 to 60 ring atoms.

5. The organic compound according to claim 1, characterized in that The Ar2 is selected from an aromatic group having 6 ring atoms substituted by a phenyl group or an alkyl group having 1 to 5 carbon atoms.

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

7. An organic light-emitting device, characterized in that: It comprises a first electrode, a second electrode and an organic functional layer; the second electrode is arranged opposite to the first electrode, and the organic functional layer is located between the first electrode and the second electrode; Wherein, the material of the organic functional layer includes at least one of the organic compounds as described in any one of claims 1 to 6.

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

9. The organic light emitting device according to claim 8, characterized in that: The guest material is a green light emitting material.

10. A display panel, characterized in that: An organic light-emitting device comprising any one of claims 7 to 9.

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