Organic compounds, compositions, organic electroluminescent devices and display panels

Abstract

The application discloses an organic compound, a composition, an organic electroluminescent device and a display panel. The organic compound has high thermal stability, can emit short-wavelength fluorescent light, and has a narrow half-peak width in a light emission spectrum, can realize deep blue light emission, and can be used as a blue fluorescent light-emitting material of an organic electroluminescent device. The composition comprises at least one organic compound and at least one organic solvent. The organic electroluminescent device comprises a cathode layer, an anode layer and an organic light-emitting layer, the organic light-emitting layer is located between the cathode layer and the anode layer, and the material of the organic light-emitting layer comprises an organic compound or is prepared from a composition.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of display, in particular to an organic compound, a composition, an organic electroluminescent device and a display panel. BACKGROUND

[0002] An organic electroluminescent device (OLED) is widely used because it has the characteristics of self-emission, high brightness, low driving voltage, wide viewing angle, high contrast, high response, etc. The organic electroluminescent device generally includes a positive electrode, a negative electrode, and an organic layer between the positive electrode and the negative electrode. The organic layer generally includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. When a voltage is applied between the positive electrode and the negative electrode of the organic electroluminescent device, the positive electrode injects holes into the organic layer, and the negative electrode injects electrons into the organic layer. The holes and the electrons meet in the light-emitting layer to form excitons, and the excitons transition to the ground state to emit light.

[0003] The existing light-emitting layer of a blue organic electroluminescent device mainly adopts a host-guest doping structure. The blue light host material of the light-emitting layer mostly adopts a condensed ring derivative based on anthracene, and the blue light guest compound mostly adopts an aryl vinyl amine compound. However, these compounds have poor thermal stability and are easy to decompose, thereby resulting in poor service life and stability of the blue organic electroluminescent device. At the same time, these compounds have poor color purity and are difficult to realize deep blue light emission, which cannot realize full-color display of the display.

[0004] Therefore, it is necessary to propose a new technical solution to solve the above technical problems. SUMMARY

[0005] The purpose of the present application is to provide an organic compound to solve the problem of poor thermal stability of the existing blue light-emitting layer material and the inability to realize deep blue light emission.

[0006] To solve the above problems, the technical solution of the present application is as follows:

[0007] In a first aspect, the present application provides an organic compound, which has a chemical structure as shown in general formula (I):

[0008]

[0009] wherein,

[0010] R1is selected from hydrogen, deuterium, a linear alkyl group, a linear alkoxy group, a linear thioalkoxy group, a branched or cyclic alkyl group, a branched or cyclic alkoxy group, a branched or cyclic thioalkoxy group, a silyl group, a keto group, an alkoxycarbonyl group, an aryloxycarbonyl group, a substituted or unsubstituted aromatic group or a heteroaromatic group, an aryloxy or heteroaryloxy group, a cyano group, a carbamoyl group, a halogen formyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, a trifluoromethyl group, chlorine, bromine, fluorine, iodine, or a combination thereof;

[0011] n is any integer from 1 to 8;

[0012] Ar1and Ar2are independently selected from a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted non-aromatic ring system;

[0013] A1and A2independently represent a chemical structure as shown in general formula (2-1) or general formula (2-2):

[0014]

[0015] wherein,

[0016] the dotted line in general formula (2-1) is the connecting site to nitrogen;

[0017] the dotted line in general formula (2-2) is the connecting site to nitrogen;

[0018] R2is independently selected from hydrogen, deuterium, a linear alkyl group, a linear alkoxy group, a linear thioalkoxy group, a branched or cyclic alkyl group, a branched or cyclic alkoxy group, a branched or cyclic thioalkoxy group, a silyl group, a keto group, an alkoxycarbonyl group, an aryloxycarbonyl group, a substituted or unsubstituted aromatic group or a heteroaromatic group, an aryloxy or heteroaryloxy group, a cyano group, a carbamoyl group, a halogen formyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, a trifluoromethyl group, chlorine, bromine, fluorine, iodine, or a combination thereof;

[0019] m is any integer from 1 to 4.

[0020] Further, R1is selected from hydrogen, deuterium, a linear alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination thereof.

[0021] Further, the general formula (I) is any one of the following general formula (II-1), general formula (II-2), general formula (II-3), and general formula (II-4):

[0022]

[0023] Further, R1in Formula (II-1) and Formula (II-2) is selected from deuterium, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, iso-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, iso-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, or 2-(2-methyl)butyl.

[0024] Further, Ar1and Ar2are each independently selected from one of the following groups:

[0025]

[0026] wherein,

[0027] * indicates the site of attachment to the nitrogen;

[0028] n2is selected from any integer from 0 to 3;

[0029] R2, R3, and R4are independently selected from hydrogen, deuterium, a straight chain alkyl group having 1 to 8 carbon atoms, a branched or cyclic alkyl group having 3 to 8 carbon atoms, phenyl, pyridyl, pyrimidyl, or naphthyl.

[0030] Further, R2, R3, and R4are independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, iso-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, iso-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-(2-methyl)butyl, phenyl, pyridyl, pyrimidyl, or naphthyl.

[0031] Further, Ar1and Ar2are independently selected from the following groups:

[0032]

[0033]

[0034]

[0035]

[0036] wherein,

[0037] tAm is a tert-amyl group;

[0038] tBu is a tert-butyl group;

[0039] “*” is a linking site linked to nitrogen.

[0040] In a second aspect, the present application provides a composition, which comprises the organic compound according to any one of the preceding technical solutions, and at least one organic solvent.

[0041] In a third aspect, the present application provides an organic electroluminescent device, comprising a cathode layer, an anode layer, and an organic light-emitting layer, wherein the organic light-emitting layer is located between the cathode layer and the anode layer, and the material of the organic light-emitting layer comprises the organic compound according to any one of the preceding technical solutions, or is prepared from the composition according to any one of the preceding technical solutions.

[0042] In a fourth aspect, the present application provides a display panel, which comprises the organic electroluminescent device according to any one of the preceding technical solutions.

[0043] The organic compound provided by the present application has a better conjugated system, higher thermal stability, can emit short-wavelength fluorescence, and has a narrow half-peak width in the emission spectrum, and can realize deep blue light emission. When the organic compound provided by the present application is used as a blue fluorescent light-emitting material of an organic electroluminescent device, the luminous efficiency and service life of the light-emitting device can be effectively improved, and deep blue light emission of the organic electroluminescent device can also be realized. BRIEF DESCRIPTION OF DRAWINGS

[0044] Figure 1 is a schematic diagram of an organic electroluminescent device provided by an embodiment of the present application.

[0045] Reference signs:

[0046] 100, an organic electroluminescent device;

[0047] 110, a substrate; 120, an anode layer; 130, a hole injection layer; 140, a hole transport layer; 150, a light-emitting layer; 160, an electron transport layer; and 170, a cathode layer. DETAILED DESCRIPTION

[0048] The terms used in the specification and the claims, unless otherwise defined, have the meanings that would be given to them by a person of ordinary skill in the art to which this application belongs. The terms used in the specification and the claims are used only for the purpose of describing and understanding this application, and are not intended to limit this application to the specific terms used in the specification and the claims.

[0049] It should be noted that in this application, the composition, printing ink or ink have the same meaning and can be interchangeable.

[0050] In this application, the aromatic group, aromatic, aromatic ring system have the same meaning and can be interchangeable.

[0051] In this application, the heteroaromatic group, heteroaromatic, heteroaromatic ring system have the same meaning and can be interchangeable.

[0052] In this application, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

[0053] In this application, the same substituent appears multiple times can be independently selected from different groups. For example, the general formula contains multiple R1, R1 can be independently selected from different groups.

[0054] In this application, "substituted or unsubstituted" means that the defined group can be substituted or not substituted. When the defined group is substituted, it is understood to be substituted by an acceptable group in the art, which specifically includes: C 1-30 alkyl, heterocyclyl containing 3 to 20 ring atoms, aryl containing 5 to 20 ring atoms, heteroaryl containing 5 to 20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halogenformyl, formyl, -NRR', cyano, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, nitro or halogen, and the above groups can be further substituted by an acceptable substituent in the art.

[0055] It can be understood that R and R' in -NRR' are independently substituted by an acceptable group in the art, and the substituent group includes H, C 1-6 alkyl, cycloalkyl containing 3 to 8 ring atoms, heterocyclyl containing 3 to 8 ring atoms, aryl containing 5 to 20 ring atoms, or heteroaryl containing 5 to 10 ring atoms.C 1-6 alkyl, cycloalkyl containing 3 to 8 ring atoms, heterocyclyl containing 3 to 8 ring atoms, aryl containing 5 to 20 ring atoms, or heteroaryl containing 5 to 10 ring atoms are substituted by one or more of the following groups:C 1-6 alkyl, cycloalkyl containing 3 to 8 ring atoms, heterocyclyl containing 3 to 8 ring atoms, halogen, hydroxyl, nitro or amino.

[0056] In the present application, the "number of ring atoms" means the number of atoms constituting a ring itself in a structural compound obtained by bonding atoms into a ring, for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound. When the ring is substituted with a substituent, the atoms included in the substituent are not included in the ring-forming atoms. The same applies to the "number of 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 thiophene group is 5.

[0057] In the present application, "alkyl" can mean straight chain, branched chain, and / or cyclic alkyl. The number of carbons of alkyl can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. In the present application, examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldodecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyihexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n- heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n- octacosyl, n-nonacosyl, n-triacontyl, and the like.

[0058] In the present application, "aryl, aralkyl, or aralkyl group" means a hydrocarbon group containing at least one aromatic ring. "Heteroaromatic or heteroaromatic group" means an aromatic hydrocarbon group containing at least one heteroatom. The heteroatom is selected from at least one of silicon, nitrogen, phosphorus, oxygen, sulfur, and germanium.

[0059] In the present application, a fused ring aromatic group refers to an aromatic group whose ring can have two or more rings, in which two carbon atoms are shared by two adjacent rings, i.e., a fused ring. A fused heteroaromatic group refers to a fused ring aromatic hydrocarbon group that contains at least one heteroatom. For the purposes of the present application, an aromatic group or a heteroaromatic group includes both aromatic ring systems and non-aromatic ring systems. Pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, and the like are also considered aromatic groups or heteroaromatic groups for the purposes of the present application. For the purposes of the present application, a fused aromatic or fused heteroaromatic ring system includes a polyaromatic or polyheteroaromatic group interrupted by short non-aromatic units, such as carbon, nitrogen, or oxygen atoms. For example, 9,9'-spirobifluorene, 9,9-dialkylfluorene, triarylamine, diaryl ether, and the like are also considered fused aromatic ring systems in the present application.

[0060] In the present application, the aromatic group is selected from the group consisting of benzene, naphthalene, anthracene, fluoranthene, phenanthrene, benzophenanthrene, pyrene, tetracene, chrysene, benzopyrene, acenaphthene, fluorene, and derivatives thereof; and the heteroaromatic group is selected from the group consisting of triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furanopyrrole, furanofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, phenanthroline, quinoxaline, phenanthridine, berberine, quinazoline, quinazolinone, dibenzothiophene, dibenzofuran, carbazole, and derivatives thereof.

[0061] The present application provides an organic compound having a chemical structure as shown in general formula (I):

[0062]

[0063]

[0064] wherein R1is selected from the group consisting of hydrogen, deuterium, straight chain alkyl, straight chain alkoxy, straight chain thioalkoxy, branched or cyclic alkyl, branched or cyclic alkoxy, branched or cyclic thioalkoxy, silyl, keto, alkoxycarbonyl, aryloxycarbonyl, substituted or unsubstituted aromatic group or heteroaromatic group, aryloxy or heteroaryloxy, cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, amine, trifluoromethyl, chlorine, bromine, fluorine, iodine, or a combination thereof; n is any integer from 1 to 8; Ar1and Ar2are independently selected from the group consisting of substituted or unsubstituted aromatic group, substituted or unsubstituted heteroaromatic group, substituted or unsubstituted non-aromatic ring system;

[0065] A1and A2independently represent a chemical structure as shown in general formula (2-1) or general formula (2-2):

[0066]

[0067] wherein the dotted line in general formula (2-1) is a connection site with nitrogen; the dotted line in general formula (2-2) is a connection site with nitrogen; R2is independently selected from hydrogen, deuterium, a linear alkyl group, a linear alkoxy group, a linear thioalkoxy group, a branched or cyclic alkyl group, a branched or cyclic alkoxy group, a branched or cyclic thioalkoxy group, a silyl group, a keto group, an alkoxycarbonyl group, an aryloxycarbonyl group, a substituted or unsubstituted aromatic group or heteroaromatic group, an aryloxy group or heteroaryloxy group, a cyano group, a carbamoyl group, a halogen formyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, a trifluoromethyl group, chlorine, bromine, fluorine, iodine, or a combination thereof; and m is any integer from 1 to 4.

[0068] Specifically, adjacent R1may form a ring with each other.

[0069] Specifically, adjacent R2may form a ring with each other.

[0070] Specifically, the linear alkyl group has 1 to 20 carbon atoms, the linear alkoxy group has 1 to 20 carbon atoms, the linear thioalkoxy group has 1 to 20 carbon atoms, the branched or cyclic alkyl group has 3 to 20 carbon atoms, the branched or cyclic alkoxy group has 3 to 20 carbon atoms, the branched or cyclic thioalkoxy group has 3 to 20 carbon atoms, the keto group has 1 to 20 carbon atoms, the alkoxycarbonyl group has 2 to 20 carbon atoms, the aryloxycarbonyl group has 7 to 20 carbon atoms, the substituted or unsubstituted aromatic group has 5 to 60 ring atoms, the heteroaromatic group has 5 to 60 ring atoms, the aryloxy group has 5 to 60 ring atoms, and the heteroaryloxy group has 5 to 60 ring atoms.

[0071] In the present application, an organic compound having a better conjugated system, higher thermal stability, capable of emitting short-wavelength fluorescence, and narrow half-peak width, and capable of realizing deep blue light emission is provided. When the organic compound provided in the present application is used as a blue fluorescent light-emitting material for an organic electroluminescent device, the light-emitting efficiency and the service life of the light-emitting device can be effectively improved, and deep blue light emission of the organic electroluminescent device can be realized.

[0072] In one embodiment of the present application, in the general formula (I), R1 is selected from hydrogen, deuterium, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination thereof.

[0073] In one embodiment of the present application, R1 is selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, or 2-(2-methyl)butyl.

[0074] In one embodiment of the present application, R1 is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, t-butyl, or t-pentyl. In other embodiments, R1 can also be selected from other straight-chain alkyl groups having 1 to 10 carbon atoms, branched alkyl groups having 3 to 10 carbon atoms, such as n-propyl, n-butyl, sec-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, or 2-(2-methyl)butyl. It is understood that when R1 is selected from other straight-chain alkyl groups having 1 to 10 carbon atoms, branched alkyl groups having 3 to 10 carbon atoms, the performance of the organic compound is similar to that when R1 is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, t-butyl, or t-pentyl.

[0075] In the present application, n is selected from 0, 1, 2, 3, or 4; specifically, n is selected from 0, 2, or 4; further, n is selected from 2. It is noted that in the embodiments provided in the present application, n is selected from 2, and in other embodiments, n can also be selected from 1, 3, or 4, and the performance of the organic compound when n is 1, 3, or 4 is similar to that when n is 2.

[0076] In the present application, m is selected from 0, 1, 2, 3 or 4; specifically, m is selected from 1, 2 or 4; further, m is selected from 1. It is to be noted that in the examples provided in the present application, m is selected from 1, and in some other embodiments, m can also be selected from 2, 3 or 4, and when m is 2, 3 or 4, the performance of the organic compound is similar to that when m is 1.

[0077] In one embodiment of the present application, m is selected from 0.

[0078] In one embodiment of the present application, the general formula (I) is any one of the general formula (II-1), general formula (II-2), general formula (II-3) and general formula (II-4) as shown below:

[0079]

[0080] Specifically, R1in the general formula (II-1) and general formula (II-2) is independently selected from deuterium, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 10 carbon atoms, an aromatic group having 5 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, or a combination of the above groups.

[0081] Specifically, R1in the general formula (II-1) and general formula (II-2) is independently selected from deuterium, a straight-chain alkyl group having 1 to 8 carbon atoms, or a branched or cyclic alkyl group having 3 to 8 carbon atoms.

[0082] Specifically, R1in the general formula (II-1) and general formula (II-2) is selected from deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl or 2-(2-methyl)butyl.

[0083] Specifically, when R1occurs multiple times, it is selected from the same group.

[0084] In the present application, Ar1and Ar2are independently selected from a substituted or unsubstituted aromatic group containing 6 to 14 C atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 14 ring atoms.

[0085] In one embodiment of the present application, Ar1and Ar2are independently selected from a substituted or unsubstituted aromatic group containing 6 to 60 carbon atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a substituted or unsubstituted non-aromatic ring system containing 3 to 30 ring atoms.

[0086] In particular, Ar1and Ar2are independently selected from one of the following groups:

[0087]

[0088] wherein,

[0089] X is selected from CR2or N;

[0090] Y is selected from NR3, CR3R4, SiR3R4, O, S, S=O or SO2;

[0091] R2, R3and R4are independently selected from hydrogen, nitrogen, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a halogen formyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a trifluoromethyl group, a chlorine atom, a bromine atom, a fluorine atom, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination thereof.

[0092] It is noted that when X is a linking site, X is selected from a C atom.

[0093] In one embodiment of the present application, Ar1and Ar2are independently selected from one of the following groups:

[0094]

[0095] wherein, * indicates a linking site to nitrogen; n2 is selected from any integer from 0 to 3;

[0096] R2, R3 and R4 are independently selected from hydrogen, deuterium, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of the above groups.

[0097] Furthermore, R2, R3, and R4 are independently selected from hydrogen, deuterium, a straight-chain alkyl group having 1 to 8 carbon atoms or a branched or cyclic alkyl group having 3 to 8 carbon atoms, or phenyl, pyridyl, pyrimidinyl, or naphthyl.

[0098] Specifically, R2, R3, and R4 are independently selected from hydrogen, deuterium, 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-butyl Hexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl or 2-(2-methyl)butyl, phenyl, pyridyl, pyrimidinyl or naphthyl.

[0099] Specifically, R2, R3, and R4 are independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, or naphthyl.

[0100] In the embodiments of this application, R2 is selected from hydrogen, deuterium, or methyl. In another embodiment, R2 may also be selected from ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, or naphthyl. When R2 is selected from ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, or naphthyl, the properties of the organic compound are similar to those of the organic compound when R2 is selected from hydrogen, deuterium, or methyl.

[0101] In the embodiments of this application, R3 and R4 are independently selected from hydrogen or deuterium. In other embodiments, R3 and R4 may also be selected from straight-chain alkyl groups having 1 to 8 carbon atoms, branched or cyclic alkyl groups having 3 to 8 carbon atoms, phenyl, pyridyl, pyrimidinyl, or naphthyl groups. When R3 and R4 are selected from straight-chain alkyl groups having 1 to 8 carbon atoms, branched or cyclic alkyl groups having 3 to 8 carbon atoms, phenyl, pyridyl, pyrimidinyl, or naphthyl groups, the properties of the organic compound are similar to those of the organic compound when R3 and R4 are independently selected from hydrogen or deuterium.

[0102] Ar1and Ar2are independently selected from the following groups:

[0103]

[0104]

[0105]

[0106] wherein tAmis a tert-amyl group; tBu is a tert-butyl group; and "*" is a linking site to nitrogen.

[0107] In an embodiment of the present application, when Ar1and Ar2appear simultaneously, they are selected from the same group.

[0108] In an embodiment of the present application, when Ar1and Ar2appear simultaneously, they are independently selected from different groups.

[0109] In an embodiment of the present application, the organic compound is any one of the following structures:

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] It should be noted that in the above structures, tAmis a tert-amyl group; tBu is a tert-butyl group; iPr is an iso-propyl group; Et is an ethyl group; and Ph is a phenyl group.

[0119] Based on the organic compound provided in the embodiments of the present application, the present application further provides a composition, which comprises the organic compound provided in any one of the embodiments of the present application, and at least one organic solvent.

[0120] Specifically, the organic compound provided in the present application is a blue light-emitting material in the composition.

[0121] Specifically, the organic solvent is selected from at least one of aromatic or heteroaromatic solvents, ester solvents, aromatic ketone solvents, aromatic ether solvents, aliphatic ketone solvents, alicyclic compound solvents, olefin compound solvents, borate solvents, phosphate compound solvents.

[0122] Further, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0123] Specifically, the aromatic or heteroaromatic solvent refers to a solvent containing aromatic or containing heteroaromatic. The aromatic or heteroaromatic solvent is selected from at least one of p-diisopropylbenzene, amylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-cymene, dipentylbenzene, tri-pentylbenzene, 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, p-cymene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorobenzyl, 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-isopropyl naphthalene, quinoline, isoquinoline, methyl 2-furoate, and ethyl 2-furoate.

[0124] The aromatic ketone solvent refers to a solvent containing aromatic ketone. The aromatic ketone solvent is selected from at least one of 1-tetralone, 2-tetralone, 2-(phenyloxy)tetralone, 6-(methyloxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone.

[0125] The aromatic ether solvent refers to a solvent containing aromatic ether. The aromatic ether solvent is selected from at least one of 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-ethylbenzyl 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-butyl anisole, trans-p-allylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxy methyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether.

[0126] The ester solvent refers to a solvent containing an ester group. The ester solvent includes octanoic acid alkyl ester, sebacic acid alkyl ester, stearic acid alkyl ester, benzoic acid alkyl ester, phenylacetic acid alkyl ester, cinnamic acid alkyl ester, oxalic acid alkyl ester, maleic acid alkyl ester, alkyl lactone, oleic acid alkyl ester, and the like. At least one of octanoic acid octyl ester, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0127] The aliphatic ketone solvent refers to a solvent containing an aliphatic ketone. The aliphatic ketone solvent is selected from at least one of 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, pivalone, isopivalone, di-n-pentyl ketone, and the like; or an aliphatic ether such as at least one of pentyl 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, and tetraethylene glycol dimethyl ether.

[0128] In one embodiment of the present application, the organic solvent is selected from at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, and indene.

[0129] The Hansen solubility parameter of the organic solvent of the present application is in the following ranges:

[0130] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, specifically in the range of 18.5 to 21.0 MPa1 / 2;

[0131] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, specifically in the range of 2.0 to 6.0 MPa1 / 2;

[0132] δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa1 / 2, specifically in the range of 2.0 to 6.0 MPa1 / 2.

[0133] Specifically, the boiling point of the organic solvent is greater than or equal to 150°C; specifically, the boiling point of the organic solvent is greater than or equal to 180°C; further, the boiling point of the organic solvent is greater than or equal to 200°C; further, the boiling point of the organic solvent is greater than or equal to 250°C; further, the boiling point of the organic solvent is greater than or equal to 275°C or greater than or equal to 300°C.

[0134] In the present application, the composition is a solution.

[0135] In the present application, the composition is a suspension.

[0136] The composition includes 0.01wt% to 20wt% of the organic compound provided in any of the embodiments provided in the present application.

[0137] Further, the mass fraction of the organic compound in the composition is 0.1wt% to 15wt%.

[0138] Further, the mass fraction of the organic compound in the composition is 0.2wt% to 5wt%.

[0139] Further, the mass fraction of the organic compound in the composition is 0.25wt% to 3wt%.

[0140] Specifically, the mass fraction of the organic compound in the composition is 0.25wt%, 0.30wt%, 0.5wt%, 0.9wt%, 1.0wt%, 1.2wt%, 1.5wt%, 1.6wt%, 1.7wt%, 1.8wt%, 2.0wt%, 2.1wt%, 2.5wt%, 2.6wt%, 2.7wt%, 2.8wt%, 2.9wt%, 3.0wt%.

[0141] The composition provided in the present application can be used as a coating or printing oil for the preparation of organic electronic devices, and specifically, the organic electronic device can be prepared by a printing or coating preparation method.

[0142] Based on the composition provided in the present application or based on the organic compound provided in the present application, the present application further provides an organic electroluminescent device 100, comprising a cathode layer 170, an anode layer 120 and an organic light-emitting layer 150, the organic light-emitting layer 150 is located between the cathode layer 170 and the anode layer 120, and the material of the organic light-emitting layer 150 comprises any one of the organic compounds provided in the embodiments of the present application, or is prepared from any one of the compositions provided in the embodiments of the present application.

[0143] Specifically, the organic electroluminescent device 100 further comprises a substrate 110, a hole injection layer 130, a hole transport layer 140 and an electron transport layer 160. The light emitting layer 150 is located between the hole transport layer 140 and the electron transport layer 160. The anode layer 120, the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160 and the cathode layer 170 are sequentially stacked on the substrate 110.

[0144] The substrate 110 is a transparent substrate or an opaque substrate. The substrate is a rigid substrate or an elastic substrate.

[0145] The material of the substrate 110 is plastic, metal, semiconductor wafer or glass.

[0146] The substrate 110 has a smooth surface.

[0147] In one embodiment of the present application, the substrate 110 is a flexible substrate, the material of which is polymeric film or plastic, and the glass transition temperature Tg is greater than or equal to 150°C. Specifically, the glass transition temperature of the substrate 110 is greater than or equal to 200°C. Specifically, the glass transition temperature of the substrate 110 is greater than or equal to 250°C. Specifically, the glass transition temperature of the substrate 110 is greater than or equal to 300°C. The material of the flexible substrate is poly(ethylene terephthalate) (PET) or polyethylene glycol (2,6-naphthalene) (PEN).

[0148] The material of the anode layer 120 is known in the art for anode, such as conductive metal, conductive metal oxide or conductive polymer, etc. The anode layer 120 can easily inject holes into the hole injection layer 130, the hole transport layer 140 or the light emitting layer 150. In one embodiment, the work function of the anode layer 120 is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV, from the absolute value of the difference between the HOMO energy level or the valence band energy level of the light emitting body in the light emitting layer 150 or the p-type semiconductor material in the hole injection layer 130, the hole transport layer 140 or the electron blocking layer. The material of the anode layer 120 can be selected from at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO and aluminum-doped zinc oxide (AZO). The material of the anode layer 120 can be formed by using a method known in the art for forming an anode, such as radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. in physical vapor deposition.

[0149] The material of the cathode layer 170 is a material known in the art for cathodes, such as a conductive metal or a conductive metal oxide. The cathode layer 170 can readily inject electrons into the electron injection layer, the electron transport layer 160 or the light emitting layer 150. In at least one embodiment, the work function of the cathode layer 170 is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV from the absolute value of the difference between the work function of the cathode layer 170 and the LUMO level or the conduction band level of the n-type semiconductor material in the light emitting layer 150 or the electron injection layer, the electron transport layer 160, or the hole blocking layer. All materials that can be used as a cathode layer for an organic electroluminescent device (OLED) can be used as a cathode material for the device of the present application. The material of the cathode layer 170 is selected from 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 cathode layer 170 can be formed into the cathode layer 170 using a method known in the art for forming a cathode layer, such as radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like.

[0150] The organic electroluminescent device 100 further comprises other functional layers, such as an electron injection layer, or a hole blocking layer.

[0151] The organic electroluminescent device 100 emits light in a wavelength range of 300 nm to 1000 nm; specifically, the organic electroluminescent device 100 emits light in a wavelength range of 350 nm to 900 nm; specifically, the organic electroluminescent device 100 emits light in a wavelength range of 400 nm to 800 nm.

[0152] Based on the organic electroluminescent device provided in any one of the above embodiments, the present application further provides a display panel, which comprises the organic electroluminescent device provided in any one of the above embodiments.

[0153] Embodiment 1

[0154] The synthetic route of the organic compound 1 is as follows:

[0155]

[0156] Synthesis of the intermediate compound 1-3:

[0157] Synthesis of intermediate compound 1-3: 10 mmol of compound 1-1, 10 mmol of compound 1-2, 0.1 mmol of Pd catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography with dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 9.07 mmol of intermediate compound 1-3, with a yield of 90.7%, MS (ASAP) = 209.

[0158] Synthesis of organic compound 1:

[0159] Synthesis of organic compound 1: 20 mmol of intermediate compound 1-3, 10 mmol of compound 1-4, 0.1 mmol of Pd catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography with dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 9.07 mmol of intermediate compound 1-3, with a yield of 90.7%, MS (ASAP) = 209.

[0160] Example 2

[0161] Synthesis route of organic compound 2:

[0162]

[0163] Synthesis of intermediate compound 2-2:

[0164] Synthesis of intermediate compound 2-2: 10 mmol of compound 1-1, 10 mmol of compound 2-1, 0.1 mmol of Pd catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography with dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 9.07 mmol of intermediate compound 1-3, with a yield of 90.7%, MS (ASAP) = 209.

[0165] Synthesis of organic compound 2:

[0166] 20 mmol of intermediate compound 2-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 1 in a yield of 69.4% and MS (ASAP) = 700.

[0167] Example 3

[0168] The synthetic route for organic compound 3 is as follows:

[0169]

[0170] Synthesis of intermediate compound 3-2:

[0171] 10 mmol of compound 3-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine), and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain 8.64 mmol of intermediate compound 3-2, with a yield of 86.4% and MS (ASAP) = 299.

[0172] Synthesis of organic compound 3:

[0173] 20 mmol of intermediate compound 3-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 3 in 80.5% yield. MS (ASAP) = 880.

[0174] Example 4

[0175] The synthetic route for organic compound 4 is as follows:

[0176]

[0177] Synthesis of intermediate compound 4-2:

[0178] 10 mmol of compound 4-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography using a developing agent of dichloromethane and petroleum ether in a volume ratio of 10:1 to obtain 8.84 mmol of intermediate compound 4-2, with a yield of 88.4%, MS (ASAP) = 299.

[0179] Synthesis of organic compound 4:

[0180] 20 mmol of intermediate compound 4-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography using a developing agent of dichloromethane and petroleum ether in a volume ratio of 10:1 to obtain organic compound 4, with a yield of 68.7%, MS (ASAP) = 880.

[0181] Example Five

[0182] The synthesis route of organic compound 5 is as follows:

[0183]

[0184] Synthesis of intermediate compound 5-2:

[0185] 10 mmol of compound 5-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography using a developing agent of dichloromethane and petroleum ether in a volume ratio of 10:1 to obtain 7.46 mmol of intermediate compound 5-2, with a yield of 74.6%, MS (ASAP) = 299.

[0186] Synthesis of organic compound 5:

[0187] The intermediate compound 5-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography with dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain the organic compound 5, with a yield of 77.9%, MS (ASAP) = 880.

[0188] Example Six

[0189] The synthesis route of the organic compound 6 is as follows:

[0190]

[0191] Synthesis of intermediate compound 6-2:

[0192] The intermediate compound 5-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography with dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain the organic compound 5, with a yield of 77.9%, MS (ASAP) = 880.

[0193] Synthesis of the organic compound 6:

[0194] The intermediate compound 5-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography with dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain the organic compound 5, with a yield of 77.9%, MS (ASAP) = 880.

[0195] Example Seven

[0196] The synthesis route of the organic compound 7 is as follows:

[0197]

[0198] Synthesis of intermediate compound 7-2:

[0199] 10 mmol of compound 7-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography using a column chromatography developing agent of dichloromethane and petroleum ether in a volume ratio of 10:1 to obtain 6.80 mmol of intermediate compound 7-2, with a yield of 68.0%, MS (ASAP) = 315.

[0200] Synthesis of organic compound 7:

[0201] 20 mmol of intermediate compound 7-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography using a column chromatography developing agent of dichloromethane and petroleum ether in a volume ratio of 10:1 to obtain organic compound 7, with a yield of 58.7%, MS (ASAP) = 912.

[0202] Example Eight

[0203] The synthesis route of organic compound 8 is as follows:

[0204]

[0205] Synthesis of intermediate compound 8-2:

[0206] 10 mmol of compound 8-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography using a column chromatography developing agent of dichloromethane and petroleum ether in a volume ratio of 10:1 to obtain 7.96 mmol of intermediate compound 8-2, with a yield of 79.6%, MS (ASAP) = 325.

[0207] Synthesis of organic compound 8:

[0208] 20 mmol of intermediate compound 8-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 8 in a yield of 69.3% and MS (ASAP) = 932.

[0209] Example 9

[0210] The synthetic route for organic compound 9 is as follows:

[0211]

[0212] Synthesis of intermediate compound 9-2:

[0213] 10 mmol of compound 9-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine), and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain 8.35 mmol of intermediate compound 9-2, with a yield of 83.5% and MS (ASAP) = 312.

[0214] Synthesis of Organic Compound 9:

[0215] 20 mmol of intermediate compound 9-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 9 in 80.6% yield. MS (ASAP) = 906.

[0216] Example 10

[0217] The synthetic route for organic compound 10 is as follows:

[0218]

[0219] Synthesis of intermediate compound 10-2:

[0220] 10 mmol of compound 10-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography using a column chromatography developing agent of dichloromethane and petroleum ether in a volume ratio of 10:1 to obtain 7.53 mmol of intermediate compound 10-2, with a yield of 75.3%, MS (ASAP) = 374.

[0221] Synthesis of organic compound 10:

[0222] 20 mmol of intermediate compound 10-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography using a column chromatography developing agent of dichloromethane and petroleum ether in a volume ratio of 10:1 to obtain organic compound 10, with a yield of 54.9%, MS (ASAP) = 1030.

[0223] Example 11

[0224] The synthesis route of organic compound 11 is as follows:

[0225]

[0226] Synthesis of intermediate compound 11-2:

[0227] 10 mmol of compound 11-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated, and the organic phase was separated by column chromatography using a column chromatography developing agent of dichloromethane and petroleum ether in a volume ratio of 10:1 to obtain 9.07 mmol of intermediate compound 11-2, with a yield of 90.7%, MS (ASAP) = 285.

[0228] Synthesis of organic compound 11:

[0229] 20 mmol of intermediate compound 11-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 11 in 79.6% yield. MS (ASAP) = 852.

[0230] Example 12

[0231] The synthetic route for organic compound 12 is as follows:

[0232]

[0233] Synthesis of intermediate compound 12-2:

[0234] 10 mmol of compound 12-1, 10 mmol of compound 2-1, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine), and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain 8.43 mmol of intermediate compound 12-2, with a yield of 84.3% and MS (ASAP) = 315.

[0235] Synthesis of organic compound 12:

[0236] 20 mmol of intermediate compound 12-2, 10 mmol of compound 12-3, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 12 in 79.3% yield. MS (ASAP) = 828.

[0237] Example 13

[0238] The synthetic route for organic compound 13 is as follows:

[0239]

[0240] Synthesis of intermediate compound 13-2:

[0241] 10 mmol of compound 13-1, 10 mmol of compound 2-1, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 7.91 mmol of intermediate compound 13-2, with a yield of 79.1%, MS (ASAP) = 325.

[0242] Synthesis of organic compound 13:

[0243] 20 mmol of intermediate compound 13-2, 10 mmol of compound 12-3, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain organic compound 13, with a yield of 65.7%, MS (ASAP) = 848.

[0244] Example 14

[0245] The synthesis route of organic compound 14 is as follows:

[0246]

[0247] Synthesis of intermediate compound 14-2:

[0248] 10 mmol of compound 14-1, 10 mmol of compound 2-1, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 8.33 mmol of intermediate compound 14-2, with a yield of 83.3%, MS (ASAP) = 374.

[0249] Synthesis of organic compound 14:

[0250] 20 mmol of intermediate compound 14-2, 10 mmol of compound 12-3, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 14 in 73.6% yield. MS (ASAP) = 946.

[0251] Example 15

[0252] The synthetic route for organic compound 15 is as follows:

[0253]

[0254] Synthesis of intermediate compound 15-2:

[0255] 10 mmol of compound 15-1, 10 mmol of compound 2-1, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine), and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain 7.92 mmol of intermediate compound 15-2, with a yield of 79.2% and MS (ASAP) = 312.

[0256] Synthesis of organic compound 15:

[0257] 20 mmol of intermediate compound 15-2, 10 mmol of compound 12-3, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 15 in a yield of 65.3% and MS (ASAP) = 822.

[0258] Example 16

[0259]

[0260] Synthesis of intermediate compound 16-3:

[0261] Compound 16-1 (10 mmol), compound 16-2 (10 mmol), Pd(dba)2(0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, stirred at 100 °C under nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (10:1, by volume) as the developing solvent to obtain 8.15 mmol of intermediate compound 16-3, with a yield of 81.5%. MS (ASAP) = 327.

[0262] Synthesis of intermediate compound 16-4:

[0263] Compound 16-3 (10 mmol), compound 12-3 (10 mmol), Pd(dba)2(0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, stirred at 100 °C under nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (10:1, by volume) as the developing solvent to obtain 8.73 mmol of intermediate compound 16-4, with a yield of 87.3%. MS (ASAP) = 605.

[0264] Synthesis of intermediate compound 16-7:

[0265] Compound 16-5 (10 mmol), compound 16-6 (10 mmol), Pd(dba)2(0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, stirred at 60 °C under nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (10:1, by volume) as the developing solvent to obtain 5.92 mmol of intermediate compound 16-7, with a yield of 59.2%. MS (ASAP) = 343.

[0266] Synthesis of compound (16):

[0267] Compound 16-4 (10 mmol), compound 16-7 (10 mmol), Pd(dba)2(0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (10:1, by volume) as the developing solvent to obtain compound 16, with a yield of 45.3%. MS (ASAP) = 868.

[0268] Example 17

[0269] The synthetic route of organic compound 17 is as follows:

[0270]

[0271] Synthesis of intermediate compound 17-2:

[0272] Compound 17-1 (10 mmol), compound 2-1 (10 mmol), Pd catalyst Pd(dba)2(0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (10:1, by volume) as the developing solvent to obtain 7.32 mmol of intermediate compound 17-2, with a yield of 73.2%, MS (ASAP) = 210.

[0273] Synthesis of organic compound 17:

[0274] Compound 17-1 (10 mmol), compound 2-1 (10 mmol), Pd catalyst Pd(dba)2(0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (10:1, by volume) as the developing solvent to obtain 7.32 mmol of intermediate compound 17-2, with a yield of 73.2%, MS (ASAP) = 210.

[0275] Example 18

[0276] The synthetic route of organic compound 18 is as follows:

[0277]

[0278] Synthesis of intermediate compound 18-2:

[0279] 10 mmol of compound 18-1, 10 mmol of compound 2-1, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 7.11 mmol of intermediate compound 18-2, with a yield of 71.1%, MS (ASAP) = 321.

[0280] Synthesis of organic compound 18:

[0281] 20 mmol of intermediate compound 18-2, 10 mmol of compound 12-3, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain organic compound 18, with a yield of 67.1%, MS (ASAP) = 840.

[0282] Example 19

[0283] The synthesis route of organic compound 19 is as follows:

[0284]

[0285] Synthesis of intermediate compound 19-2:

[0286] 10 mmol of compound 19-1, 10 mmol of compound 2-1, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 6.69 mmol of intermediate compound 19-2, with a yield of 66.9%, MS (ASAP) = 259.

[0287] Synthesis of organic compound 19:

[0288] 20 mmol of intermediate compound 19-2, 10 mmol of compound 12-3, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 19 in a yield of 61.3% and MS (ASAP) = 716.

[0289] Example 20

[0290] The synthetic route for organic compound 20 is as follows:

[0291]

[0292] Synthesis of intermediate compound 20-2:

[0293] 10 mmol of compound 20-1, 10 mmol of compound 2-1, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine), and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain 7.21 mmol of intermediate compound 20-2, with a yield of 72.1% and MS (ASAP) = 315.

[0294] Synthesis of organic compound 20:

[0295] 20 mmol of intermediate compound 20-2, 10 mmol of compound 12-3, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 20 in 71.8% yield. MS (ASAP) = 828.

[0296] Example 21

[0297] The synthetic route for organic compound 21 is as follows:

[0298]

[0299] Synthesis of intermediate compound 21-2:

[0300] 10 mmol of compound 21-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 8.18 mmol of intermediate compound 21-2, with a yield of 81.8%, MS (ASAP) = 316.

[0301] Synthesis of organic compound 21:

[0302] 20 mmol of intermediate compound 21-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain organic compound 21, with a yield of 60.1%, MS (ASAP) = 914.

[0303] Example 22

[0304] Synthesis route of organic compound 22:

[0305]

[0306] Synthesis of intermediate compound 22-2:

[0307] 10 mmol of compound 22-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 8.56 mmol of intermediate compound 22-2, with a yield of 85.6%, MS (ASAP) = 300.

[0308] Synthesis of organic compound 22:

[0309] 20 mmol of intermediate compound 22-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 22 in a yield of 54.2% and MS (ASAP) = 882.

[0310] Example 23

[0311] The synthetic route for organic compound 23 is as follows:

[0312]

[0313] Synthesis of intermediate compound 23-2:

[0314] 10 mmol of compound 23-1, 10 mmol of compound 2-1, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butylphosphine), and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain 6.51 mmol of intermediate compound 23-2, with a yield of 65.1% and MS (ASAP) = 309.

[0315] Synthesis of organic compound 23:

[0316] 20 mmol of intermediate compound 23-2, 10 mmol of compound 12-3, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene. The mixture was stirred at 100 °C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane and washed with water. The organic phase was separated by column chromatography using a dichloromethane and petroleum ether eluent in a volume ratio of 10:1 to obtain organic compound 23 in a yield of 57.3% and MS (ASAP) = 816.

[0317] Example 24

[0318] The synthetic route for organic compound 24 is as follows:

[0319]

[0320] Synthesis of intermediate compound 24-2:

[0321] 10 mmol of compound 24-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butyl phosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 8.22 mmol of intermediate compound 24-2, with a yield of 82.2%, MS (ASAP) = 375.

[0322] Synthesis of organic compound 24:

[0323] 20 mmol of intermediate compound 24-2, 10 mmol of compound 1-4, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain organic compound 24, with a yield of 74.3%, MS (ASAP) = 1032.

[0324] Example 25

[0325] The synthesis route of organic compound 25 is as follows:

[0326]

[0327] Synthesis of intermediate compound 25-2:

[0328] 10 mmol of compound 25-1, 10 mmol of compound 1-2, 0.1 mmol of palladium catalyst Pd(dba)2, 0.2 mmol of TTBP (tri-tert-butyl phosphine) and 30 mmol of sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, and after cooling, the solvent was removed by rotary evaporation. The organic phase was extracted with dichloromethane, and the organic phase was washed with water and separated. The organic phase was separated by column chromatography using dichloromethane and petroleum ether (volume ratio 10:1) as the developing agent to obtain 7.62 mmol of intermediate compound 25-2, with a yield of 76.2%, MS (ASAP) = 375.

[0329] Synthesis of organic compound 25:

[0330] The 20 mmol intermediate compound 25-2, 10 mmol compound 1-4, 0.1 mmol palladium catalyst Pd(dba)2, 0.2 mmol of TTBP and 30 mmol sodium tert-butoxide were dissolved in toluene solvent, stirred at 100°C under nitrogen atmosphere for 6h, after cooling, the solvent was removed by rotary evaporation, the organic phase was extracted with dichloromethane, and the organic phase was washed with water, and column chromatography was carried out with dichloromethane and petroleum ether (volume ratio 10:1) as column chromatography developing agent to separate the organic compound 25, the yield was 67.9%, MS (ASAP) = 1032.

[0331] The energy levels HOMO, LUMO, T1 and S1 of the organic compounds 1 to 25 synthesized in Examples 1 to 25 and the comparative compound 1 were calculated.

[0332] Among them, the chemical structural formula of the comparative compound 1 is as follows:

[0333]

[0334] Calculation method:

[0335] The TD-DFT (Time-Dependent Density Functional Theory) was used by Gaussian 09W (Gaussian Inc.), first the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet) was used to optimize the molecular geometry, then the energy structure of the organic molecule was calculated by the TD-DFT (Time-Dependent Density Functional Theory) method "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels were calculated according to the following calibration formula, and S1, T1 and the resonance factor f(S1) were directly used.

[0336] HOMO (eV) = ((HOMO(G) x 27.212) - 0.9899) / 1.1206;

[0337] LUMO (eV) = ((LUMO(G) x 27.212) - 2.0041) / 1.385.

[0338] Where HOMO, LUMO, T1 and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree. The results are shown in Table 1 below.

[0339] Table 1:

[0340] Materials HOMO [eV] LUMO [eV] T1 [eV] S1 [eV] Compound 1 -5.15 -2.49 1.81 2.93 Compound 2 -4.99 -2.52 1.80 2.95 Compound 3 -5.03 -2.51 1.83 2.92 Compound 4 -5.06 -2.54 1.78 2.91 Compound 5 -4.99 -2.54 1.83 2.89 Compound 6 -5.10 -2.56 1.85 2.95 Compound 7 -5.07 -2.49 1.77 2.93 Compound 8 -5.02 -2.43 1.79 2.96 Compound 9 -4.99 -2.47 1.82 2.91 Compound 10 -4.96 -2.59 1.80 2.89 Compound 11 -5.17 -2.52 1.81 2.85 Compound 12 -5.12 -2.51 1.80 2.86 Compound 13 -5.13 -2.49 1.85 2.81 Compound 14 -5.07 -2.53 1.79 2.83 Compound 15 -5.15 -2.54 1.79 2.93 Compound 16 -5.06 -2.52 1.83 2.95 Compound 17 -4.91 -2.49 1.82 2.91 Compound 18 -4.93 -2.41 1.81 2.93 Compound 19 -5.03 -2.44 1.83 2.91 Compound 20 -5.01 -2.44 1.83 2.95 Compound 21 -5.11 -2.43 1.83 2.97 Compound 22 -5.13 -2.47 1.78 2.98 Compound 23 -5.07 -2.51 1.83 2.91 Compound 24 -5.04 -2.50 1.81 2.91 Compound 25 -5.03 -2.43 1.81 2.91 Comparative Compound 1 -5.10 -2.07 2.61 2.98

[0341] The organic compounds 1 to 25, comparative compound 1 synthesized using the above-mentioned preparation examples 1 to 25 were used to prepare the following organic light emitting devices OLED-1, OLED-2, OLED-3, OLED-4, OLED-5, OLED-6, OLED-7, OLED-8, OLED-9, OLED-10, OLED-11, OLED-12, OLED-13, OLED-14, OLED-15, OLED-16, OLED-17, OLED-18, OLED-19, OLED-20, OLED-21, OLED-22, OLED-23, OLED-24, OLED-25, OLED-Ref1, and comparative OLED-Ref1 according to the following preparation procedures:

[0342] a. An ITO (indium tin oxide) conductive glass substrate was provided, cleaned with a cleaning agent (chloroform), and then subjected to ultraviolet ozone treatment;

[0343] b. In a clean room, a PEDOT (polyethylene dioxythiophene, Clevios AI4083) solution was spin-coated on the ITO conductive glass substrate, and then treated on a hot plate at 180°C for 10 minutes to obtain a hole injection layer with a thickness of 40 nm; TM c. In a nitrogen glove box, a TFB or PVK (Sigma Aldrich, average Mn 25,000-50,000) solution with a concentration of 5 mg / ml in toluene was spin-coated on the hole injection layer, and then treated on a hot plate at 180°C for 60 minutes to obtain a hole transport layer with a thickness of 20 nm;

[0344] d. In a nitrogen glove box, an organic compound 1 to 25, comparative compound 1 was spin-coated on the hole transport layer, and then treated on a hot plate at 180°C for 60 minutes to obtain a light emitting layer with a thickness of 20 nm;

[0345] d. spin-coating a mixture of organic light-emitting materials on the hole transport layer in a nitrogen glove box, followed by treatment on a hot plate at 140°C for 10 minutes to obtain an organic light-emitting layer with a thickness of 40 nm, wherein the solvent in the mixture of organic light-emitting materials is methyl benzoate, the host material is BH, and the guest materials are organic compound 1 to organic compound 25 and comparative compound 1, respectively, and the weight ratio of the host material to the guest material is 95:5;

[0346] e. transferring the substrate into a vacuum chamber, placing ET (chemical structure as follows) and Liq (chemical structure as follows) in different evaporation units, and co-depositing them at a ratio of 50wt% in high vacuum (1x10-6 mbar) to form an electron transport layer with a thickness of 20 nm on the organic light-emitting layer, followed by depositing an Al cathode with a thickness of 100 nm to obtain OLED devices, respectively;

[0347] f. encapsulating the OLED device with a resin cured by ultraviolet light in a nitrogen glove box.

[0348] The di-substituted indene-based organic compound 1 corresponds to the devices OLED-1-25 and OLED-Ref1, respectively.

[0349] The chemical structure of the BD comparative compound in step d is as follows:

[0350]

[0351] The chemical structure of the BH in step d is as follows:

[0352]

[0353] The chemical structure of the ET in step e is as follows:

[0354]

[0355] The chemical structure of Liq is as follows:

[0356]

[0357] The current-voltage (J-V) characteristics of the organic electroluminescent devices OLED-1 to OLED-25 and OLED-Ref1 were characterized by a characterization device, and important parameters such as luminous efficiency (CE@1 knits) and lifetime (LT90@1 knits) were recorded, and the results are shown in Table 2.

[0358] Table 2:

[0359] Device Guest material Color coordinates Luminous efficiency (cd / A) Lifetime (h) OLED-1 Compound 1 0.146,0.083 8.9 494 OLED-2 Compound 2 0.146,0.083 8.7 487 OLED-3 Compound 3 0.146,0.083 8.6 505 OLED-4 Compound 4 0.146,0.089 9.1 493 OLED-5 Compound 5 0.145,0.081 8.8 476 OLED-6 Compound 6 0.145,0.081 8.5 468 OLED-7 Compound 7 0.146,0.089 8.9 481 OLED-8 Compound 8 0.145,0.081 8.5 471 OLED-9 Compound 9 0.145,0.081 8.3 473 OLED-10 Compound 10 0.145,0.086 8.3 470 OLED-11 Compound 11 0.144,0.083 8.9 469 OLED-12 Compound 12 0.144,0.086 8.4 489 OLED-13 Compound 13 0.146,0.089 8.4 468 OLED-14 Compound 14 0.145,0.088 8.6 486 OLED-15 Compound 15 0.144,0.089 9.2 503 OLED-16 Compound 16 0.146,0.086 8.1 466 OLED-17 Compound 17 0.145,0.087 8.1 453 OLED-18 Compound 18 0.145,0.087 8.1 459 OLED-19 Compound 19 0.145,0.083 8.4 456 OLED-20 Compound 20 0.144,0.083 8.7 451 OLED-21 Compound 21 0.144,0.081 8.1 456 OLED-22 Compound 22 0.146,0.081 8.1 478 OLED-23 Compound 23 0.145,0.087 8.4 469 OLED-24 Compound 24 0.144,0.089 8.5 445 OLED-25 Compound 25 0.146,0.085 8.3 458 OLED-Ref1 Comparative Compound 1 0.148,0.145 4.3 193

[0360] As shown in Table 2, the color coordinates of the organic electroluminescent device prepared by using the organic compound 1-25 provided by the embodiments of the present application as the light-emitting material in the organic light-emitting layer are more superior to those of the organic electroluminescent device prepared by using the comparative compound 1 as the light-emitting material.

[0361] In addition, the organic electroluminescent device prepared by using the organic compound 1-25 provided by the embodiments of the present application as the light-emitting material in the organic light-emitting layer has a light-emitting efficiency in the range of 8-9 cd / A, and has more superior light-emitting efficiency. This is because, compared with the comparative compound 1, the organic compound provided by the embodiments of the present application has a better conjugated system, and the introduction of the cyclopentyl group enhances the solubility of the compound, thereby improving the purity of the compound, so as to improve the performance of the device. In addition, compared with the comparative compound 1, the indene group in the organic compound provided by the present application is superior to the phenyl group in the comparative compound 1 in terms of stability after film formation.

[0362] Further, in terms of the service life of the organic electroluminescent device, the organic electroluminescent device prepared by using the organic compound 1-25 as the light-emitting material in the organic light-emitting layer has a more superior service life than the organic electroluminescent device prepared by using the comparative compound 1 as the light-emitting material.

[0363] The specific embodiments of the present application are described in detail above. The above-described embodiments disclosed by the present application are only preferred embodiments of the present application, and those of ordinary skill in the art can make many variations and improvements without departing from the concept of the present application. These variations and improvements fall within the scope of the claims of the present application.

Claims

1. An organic compound characterized in that, The organic compound has a chemical structure as shown in general formula (I): （I） wherein, R1is selected from hydrogen, a linear alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms; n is any integer from 1 to 8; Ar1and Ar2are each independently selected from one of the following groups: ； * indicates the connection site to nitrogen; n2is selected from any integer from 0 to 3; A1and A2independently represent a chemical structure as shown in general formula (2-1) or general formula (2-2): （2-1）（2-2） wherein, the dotted line in general formula (2-1) is the connection site to nitrogen; the dotted line in general formula (2-2) is the connection site to nitrogen; R2, R3and R4are independently selected from hydrogen, a linear alkyl group having 1 to 8 carbon atoms, a branched or cyclic alkyl group having 3 to 8 carbon atoms, phenyl, pyridyl; m is any integer from 1 to 4.

2. The organic compound according to claim 1, wherein The general formula (I) is any one of the following general formulae (II-1), general formula (II-2), general formula (II-3) and general formula (II-4): 。 3. The organic compound according to claim 2, wherein R1in general formula (II-1) and general formula (II-2) is selected from hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyl-octyl, 2-hexyl-octyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl or 2-(2-methyl)butyl.

4. The organic compound according to claim 1, wherein R2, R3and R4are independently selected from hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyl-octyl, 2-hexyl-octyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-(2-methyl)butyl, phenyl or pyridyl.

5. The organic compound according to claim 1, wherein The Ar1and Ar2are independently selected from the following groups: ； wherein, tAm is t-amyl; tBu is t-butyl; "*" is the connection site to nitrogen.

6. A composition characterized in that, comprising the organic compound according to any one of claims 1 to 5 and at least one organic solvent.

7. An organic electroluminescent device, characterized by An organic electroluminescence device comprising a cathode layer, an anode layer, and an organic light-emitting layer between the cathode layer and the anode layer, a material of the organic light-emitting layer comprising the organic compound according to any one of claims 1 to 5, or prepared from the composition according to claim 6.

8. A display panel, characterized by, An organic electroluminescence device according to claim 7.

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