Organic compounds and mixtures, compositions and organic electronic devices comprising the same

Abstract

The present application discloses an organic compound and mixtures, compositions and organic electronic devices comprising the organic compound, the organic compound having a structure as shown in general formula (I): The organic compound is used in organic electronic devices, in particular as light-emitting material in the light-emitting layer of organic electronic devices, to improve the efficiency and lifetime of organic electronic devices.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of light-emitting materials, in particular to an organic compound, and a mixture, a composition and an organic electronic device comprising the organic compound. BACKGROUND

[0002] In flat panel display and lighting applications, organic light-emitting diodes (OLEDs) have the advantages of low cost, light weight, low operating voltage, high brightness, color tunability, wide viewing angle, easy assembly and low energy consumption, and thus become the most potential display technology.

[0003] The principle of light emission of an organic electronic device is organic electroluminescence, which refers to the phenomenon of converting electrical energy into light energy by using organic substances. An organic electroluminescent device utilizing organic electroluminescence generally has a positive electrode and a negative electrode and a functional layer containing organic substances therebetween. In order to improve the efficiency and service life of the organic electroluminescent element, the functional layer has a multi-layer structure, and each layer of the functional layer contains different organic substances. Specifically, it includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer or an electron injection layer, etc. In the organic electroluminescent device, a voltage is applied between the two electrodes, then holes are injected from the positive electrode to the organic layer, and electrons are injected from the negative electrode to the organic layer. When the injected holes and electrons meet, an exciton is formed, and light is emitted when the exciton transitions to the ground state. Such an organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, high response, etc.

[0004] In order to improve the light-emitting efficiency of organic light-emitting diodes, various fluorescent and phosphorescent light-emitting material systems have been developed. Among them, the organic light-emitting diode using fluorescent materials has the characteristics of high reliability, but its internal electroluminescence quantum efficiency is limited to 25% under electrical excitation, because the branching ratio of singlet and triplet excited states of excitons is 1:3. The organic light-emitting diode using phosphorescent materials has achieved almost 100% internal electroluminescence quantum efficiency, but there is a big problem with phosphorescent OLEDs: roll-off effect, i.e. the light-emitting efficiency decreases rapidly with the increase of current or brightness, which is particularly disadvantageous for high brightness applications.

[0005] So far, the phosphorescent materials with practical value are iridium and platinum complexes, which are rare and expensive raw materials, and the synthesis of complexes is very complex, so the cost is also quite high. In order to overcome the above problems, Adachi proposed the concept of reverse internal conversion, which can utilize organic compounds, i.e. not utilize metal complexes, to achieve high efficiency comparable to phosphorescent OLEDs. This concept has been realized through various material combinations, such as: 1) using composite excited states; 2) using thermally excited delayed fluorescence (TADF) materials.

[0006] Traditional red and green TADF materials have achieved good results in various aspects of performance, but compared with phosphorescent light emitting materials, there is still a certain gap in performance in terms of efficiency or service life. SUMMARY

[0007] Therefore, the present application provides an organic compound as a new type of light emitting material for use in organic electronic devices, aiming to improve the problems of low luminous efficiency and short service life of organic electronic devices.

[0008] The technical solution of the present application is as follows:

[0009] An organic compound has a structure as shown in general formula (I):

[0010]

[0011] wherein m is 0, 1, 2, 3 or 4;

[0012] Ar1, Ar2, Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, or alkyl groups having 1 to 30 carbon atoms;

[0013] X1, X2, X3 are independently selected from CR6 or N, and at least one of X1, X2, X3 is selected from N;

[0014] R1, R2, R3, R4, R5, R6 are independently selected from -H, -D, straight-chain alkyl groups having 1 to 20 C atoms, straight-chain alkoxy groups having 1 to 20 C atoms, straight-chain thioalkoxy groups having 1 to 20 C atoms, branched alkyl groups having 3 to 20 C atoms, or cyclic alkyl groups having 3 to 20 C atoms, branched alkoxy groups having 3 to 20 C atoms, or cyclic alkoxy groups having 3 to 20 C atoms, branched thioalkoxy groups having 3 to 20 C atoms, or cyclic thioalkoxy groups having 3 to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, aryloxycarbonyl groups having 7 to 20 C atoms, alkenyl groups having 1 to 20 C atoms, -CN, carbamoyl, halogen formyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms, or combinations of these groups, each occurrence.

[0015] Correspondingly, the application further provides a mixture comprising the organic compound and at least one organic functional material selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an emitter, a host material or an organic dye.

[0016] Correspondingly, the application further provides a composition comprising the organic compound or the mixture and at least one organic solvent.

[0017] Correspondingly, the application further provides an organic electronic device comprising at least one functional layer, wherein the functional layer comprises the organic compound or the mixture, or the functional layer is prepared from the composition.

[0018] Compared with the prior art, the organic compound has the following beneficial effects:

[0019] The organic compound has a D-A system, and when applied to an organic electronic device as a green light host material, the efficiency and the service life of the organic electronic device can be effectively improved. BRIEF DESCRIPTION OF DRAWINGS

[0020] In order to more clearly illustrate the technical solutions in the embodiments of the application, the drawings needed in the embodiment description will be briefly introduced below. Obviously, the drawings in the following description are only some embodiments of the application, and other drawings can be obtained by those skilled in the art without any creative effort on the basis of these drawings.

[0021] Figure 1 is a structural schematic diagram of an organic electronic device provided by the embodiments of the application. DETAILED DESCRIPTION

[0022] The technical solutions in the embodiments of the present application will be described clearly and completely in the embodiments of the present application in combination with the drawings in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all the embodiments of the present application. Based on the embodiments in the present application, all the other embodiments obtained by a person of ordinary skill in the art without creative effort belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation described herein is only used for illustration and explanation of the present application, and is not used to limit the present application. In the present application, the orientation words such as "upper" and "lower" generally refer to the upper and lower in the actual use or working state of the device, and specifically refer to the drawing surface direction in the drawings. In addition, in the description of the present application, the term "comprising" means "including but not limited to", the term "multiple" means "two or more", and the term "and / or" includes any and all combinations of one or more related listed items. Various embodiments of the present application can exist in the form of a range; it should be understood that the description in the form of a range is only for the convenience and brevity, and should not be understood as a hard limit on the scope of the present application; therefore, it should be considered that the described range has been specifically disclosed all possible sub-ranges and single values within the range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the described range, such as 1, 2, 3, 4, 5 and 6, regardless of the range. In addition, whenever a numerical range is indicated in the present application, it refers to any cited number (fraction or integer) within the indicated range.

[0023] In the present application, the composition, printing ink, and ink have the same meaning and can be interchangeable.

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

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

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

[0027] In the present application, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple R1, R1 can be independently selected from different groups.

[0028] In the present application, "substituted or unsubstituted" means that the defined group can be substituted or unsubstituted. When the defined group is substituted, it is understood that the defined group can be substituted with one or more substituents R selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen, an alkyl group having 1 to 20 C atoms, a heterocyclic group having 3 to 20 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, -NR'R", a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halogen carboxyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups can be further substituted with an acceptable substituent in the art; it is understood that R' and R" in -NR'R" are each independently selected from, but not limited to, H, D (deuterium atom), a cyano group, an isocyano group, a nitro group, or a halogen, an alkyl group having 1 to 10 C atoms, a heterocyclic group having 3 to 20 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms. Preferably, R is selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen, an alkyl group having 1 to 10 C atoms, a heterocyclic group having 3 to 10 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halogen carboxyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups can be further substituted with an acceptable substituent in the art.

[0029] In the present application, "ring atom number" means the number of atoms among the atoms constituting a ring itself of a structural compound obtained by bonding atoms into a ring (e.g., 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 atoms. The same is true for the "ring atom number" described below, unless otherwise specified. For example, the ring atom number of a benzene ring is 6, the ring atom number of a naphthalene ring is 10, and the ring atom number of a thiophene group is 5.

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

[0031] In the present application, "heteroaryl or heteroaromatic group" refers to a group in which at least one carbon atom in an aryl group is replaced by a non-carbon atom, which can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted; suitable examples include, but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, perylenyl, phenanthridinyl, perimidinyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.

[0032] In the present application, "alkyl" can represent a straight chain, branched chain, and / or cyclic alkyl group. The number of carbons in the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing 1-9 carbon atoms, which can be Ci alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl, each occurrence of which is independent of the other and is optionally substituted as defined herein. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, i-propyl, n-butyl, s-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-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyidecyl, 2-butyidecyl, 2-hexyidecyl, 2-octyidecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethyihexadecyl, 2-butyihexadecyl, 2-hexyihexadecyl, 2-octyihexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyieicosyl, 2-butyieicosyl, 2-hexyieicosyl, 2-octyieicosyl, n- heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n- octacosyl, n-nonacosyl, n-triacontyl, adamantyl, and the like.

[0033] In the present application, substituent abbreviation correspondences are: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-met, p-para, Me-methyl, Et-ethyl, Pr-propyl, Bu-butyl, Am-n-amyl, Hx-hexyl, Cy-cyclohexyl.

[0034] In the present application, "amine group" refers to derivatives of amines, having the structural feature of the formula -N(X)2, where each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, and the like. Non-limiting types of amine groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl)2, -NH(heterocyclyl), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), and the like.

[0035] In the present application, "*" attached to a single bond indicates a connection or a fused site.

[0036] In the present application, when no connection site is indicated in a group, it means that any optional connectable site in the group is taken as the connection site.

[0037] In the present application, when no fused site is indicated in a group, it means that any optional fused site in the group is taken as the fused site, preferably two or more sites in the group in ortho position are taken as the fused site.

[0038] In the present application, when there are multiple substituents with the same symbol on the same group, each substituent can be the same as or different from each other, for example 6 R 1 may be the same as or different from each other.

[0039] In the present application, a single bond connecting a substituent runs through the corresponding ring, which means that the substituent can be connected to any optional position of the ring, for example R is connected to any substitutable position of the benzene ring, such as means may be connected to any optional substitutable position to form a naphthalene ring.

[0040] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0041] The technical solutions of the present application are as follows:

[0042] An organic compound having a structure as shown in general formula (I):

[0043]

[0044] wherein m is 0, 1, 2, 3 or 4;

[0045] Ar1, Ar2, Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, or alkyl groups having 1 to 30 carbon atoms;

[0046] X1, X2, X3 are independently selected from CR6 or N, and at least one of X1, X2, X3 is selected from N;

[0047] R1, R2, R3, R4, R5, R6are each independently at each occurrence selected from the group consisting of -H, -D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, an alkenyl group having 1 to 20 C atoms, -CN, a carbamoyl group, a halogenformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups.

[0048] Further, the compound of formula (I) is selected from the group consisting of the structures shown in formula (II):

[0049]

[0050] In one embodiment, the compound of the present application is selected from any one of the structures shown in formula (III-1) to (III-6):

[0051]

[0052] In one embodiment, R1, R2, R3, R4, R5, R6are each independently at each occurrence selected from the group consisting of -H, -D, a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, or a cyclic alkyl group having 3 to 10 C atoms, a silyl group, -CN, an isocyano group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups.

[0053] In one embodiment, each occurrence of R1, R2, R3, R4, R5, R6is independently selected from -H, -D, a linear alkyl group having from 1 to 10 C atoms, a branched alkyl group having from 3 to 10 C atoms, or a cyclic alkyl group having from 3 to 10 C atoms, a silyl group, -CN, isocyano, hydroxyl, nitro, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having from 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having from 5 to 10 ring atoms, or a combination of these groups.

[0054] The "substituted or unsubstituted" meaning is as described above.

[0055] In one embodiment, each occurrence of R1, R2, R3, R4, R5, R6is independently selected from -H, -D, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-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, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triazinyl, pyridyl, pyrimidyl, imidazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, diphenzo-thiophenyl, diphenzo-furanyl, phenyl-substituted carbazolyl, fluorenyl, alkyl-substituted fluorenyl having from 1 to 10 C atoms.

[0056] In one embodiment, each occurrence of R1, R2is independently selected from -H, -D, a linear alkyl group having from 1 to 4 C atoms, a branched alkyl group having from 3 to 6 C atoms, or a cyclic alkyl group having from 3 to 6 C atoms, a substituted or unsubstituted aromatic group having from 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having from 6 to 10 ring atoms, or a combination of these groups.

[0057] In one embodiment, R1and R2are selected from the same group; further, R1and R2are both selected from -H, methyl, ethyl, i-propyl, t-butyl, cyclohexyl, or phenyl.

[0058] In one embodiment, each occurrence of R3, R4is independently selected from -H, -D, a linear alkyl group having from 1 to 4 C atoms, a branched alkyl group having from 3 to 6 C atoms, or a cyclic alkyl group having from 3 to 6 C atoms, a substituted or unsubstituted aromatic group having from 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having from 6 to 10 ring atoms, or a combination of these groups.

[0059] In one embodiment, R3 and R4 are selected from the same group. Further, R3 and R4 are both selected from -H, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, or phenyl. Even further, R3 and R4 are both selected from methyl.

[0060] In one embodiment, each occurrence of R5 is independently selected from -D, a straight-chain alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, an aromatic group having 6 to 10 substituted or unsubstituted cyclic atoms, a heteroaromatic group having 6 to 10 substituted or unsubstituted cyclic atoms, or a combination of these groups.

[0061] In one embodiment, m is selected from 0 or 1; further, m is selected from 0.

[0062] In one embodiment, each occurrence of R6 is independently selected from -H, -D, a straight-chain alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, an aromatic group having 6 to 10 substituted or unsubstituted cyclic atoms, a heteroaromatic group having 6 to 10 substituted or unsubstituted cyclic atoms, or a combination of these groups.

[0063] In one implementation, X1, X2, and X3 are independently selected from N or CH. In a specific embodiment, X1, X2, and X3 are all selected from N.

[0064] In one example, Ar1, Ar2, and Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 25 ring atoms, and substituted or unsubstituted heteroaromatic groups having 6 to 25 ring atoms.

[0065] In one specific embodiment, Ar1, Ar2, and Ar3 are independently selected from the following groups:

[0066]

[0067] in:

[0068] Each time X appears, it is independently selected from CR7 or N;

[0069] Each occurrence of Y is independently selected from CR8R9 and NR. 10 , SiR8R9, O, S, Se, S=O, S(=O)2 or PR 10 ;

[0070] R7, R8, R9, R 10each occurrence, independently, is selected from the group consisting of: -H, -D, a straight-chain alkyl group having 1 to 20 C atoms, a straight-chain alkoxy group having 1 to 20 C atoms, a straight-chain thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, an alkenyl group having 1 to 20 C atoms, -CN, 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, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups;

[0071] when X is a point of attachment, X is selected from C; when Y is a point of attachment, Y is selected from N.

[0072] In a particular embodiment, Ar1, Ar2, Ar3are independently selected from the following groups:

[0073]

[0074] wherein: * indicates a point of attachment.

[0075] In a particular example, R7, R8, R9, R 10 each occurrence, independently, is selected from the group consisting of: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a cyano group, a nitro group, -CF3, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 10 ring atoms.

[0076] More particularly, Ar1, Ar2, Ar3are each occurrence, independently, selected from the following groups:

[0077]

[0078]

[0079] * indicates a point of attachment.

[0080] In a certain embodiment, Ar3is selected from Further, Ar3is selected from In one embodiment, R7is selected from the group consisting of: -H, -D, a linear alkyl group having 1 to 4 C atoms, a branched or cyclic alkyl group having 3 to 6 C atoms; further, R7is selected from the group consisting of: -H, -D, methyl, isopropyl, tert-butyl or phenyl.

[0081] In one embodiment, Ar1, Ar2are selected from the group consisting of

[0082] In one embodiment, the organic compound is selected from formula (IV-1) or (IV-2) or (IV-3):

[0083]

[0084] Preferably, X in formula (IV-1) or (IV-2) or (IV-3) is selected from CR7or N at each occurrence. In one embodiment R7is selected from the group consisting of: -H, -D, a linear alkyl group having 1 to 4 C atoms, a branched or cyclic alkyl group having 3 to 6 C atoms; further, R7is selected from the group consisting of: -H, -D, methyl, isopropyl, tert-butyl or phenyl.

[0085] As an example, in some embodiments, the organic compound of the present application can be selected from, but not limited to, any one of the following structures:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] It can be understood that H in the structural formula of the above-mentioned organic compound can be further substituted.

[0098] In some embodiments, the organic compounds of the present application can be applied as organic functional material in a functional layer of an organic electronic device, in particular in a functional layer of an OLED device. The organic functional material can be, but is not limited to, a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), an Emitter, a Host Emitter and an organic dye.

[0099] In some embodiments, the organic compounds of the present application are used in an emitting layer, preferably the organic compounds of the present application are used as emitting layer guest material in an emitting layer.

[0100] The present application further relates to a mixture comprising at least one organic compound as described above and at least one further organic functional material. The further organic functional material is selected from the group consisting of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, Emitters, Host Emitters and organic dyes. A detailed description of various organic functional materials is given in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire content of these three patent documents is hereby incorporated by reference.

[0101] The present application further relates to a mixture comprising at least one organic compound as described above and at least one further organic functional material. The further organic functional material is selected from the group consisting of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, Emitters, Host Emitters and organic dyes. A detailed description of various organic functional materials is given in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire content of these three patent documents is hereby incorporated by reference.

[0102] The organic solvent is selected from at least one of an aromatic or heteroaromatic based solvent, an ester based solvent, an aromatic ketone based solvent, an aromatic ether based solvent, an aliphatic ketone, an aliphatic ether, an alicyclic compound, an olefinic compound, a boronate ester compound and a phosphonate ester compound.

[0103] In at least one embodiment, the organic solvent in the composition is selected from an aromatic or heteroaromatic based solvent.

[0104] The aromatic or heteroaromatic based solvent can be selected from, but not limited to, 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, dinaphthyl, 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-methylaniline, 4-isopropylbiphenyl, a,a-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.

[0105] The ester based solvent can be selected from, but not limited to, 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 lactate, oleic acid alkyl ester, and the like. Particularly preferred are at least one of octanoic acid octyl ester, diethyl sebacate, diallyl phthalate, and isononyl isononanoate.

[0106] The aromatic ketone based solvent can be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenyloxy)tetralone, 6-(methyloxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof. Among these, as examples, the derivatives can be selected from, but not limited to, at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0107] The aromatic ether based solvent can be selected from, but not limited to, 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, and ethyl-2-naphthyl ether.

[0108] The aliphatic ketone-based solvent can be selected from, but not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4- nonanone, fenchone, p-methylphenylacetone, di-n-pentyl ketone, and the like; or an aliphatic ether, such as at least one of amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.

[0109] It can be appreciated that the organic solvent can be used alone or as a mixed solvent of two or more organic solvents.

[0110] In some embodiments, the composition of the present application includes at least one organic compound or mixture as described above, and at least one organic solvent, and can further include another organic solvent.

[0111] The another organic solvent can be selected from, but not limited to, 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 (DMSO), tetralin, decalin, and indene.

[0112] In some embodiments, the organic solvent suitable for the present application is a solvent having a Hansen solubility parameter in the following ranges:

[0113] δd (dispersion force) in the range of 17.0-23.2 MPa1 / 2, especially in the range of 18.5-21.0 MPa1 / 2;

[0114] δp (polar force) in the range of 0.2-12.5 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2;

[0115] δh (hydrogen bonding force) in the range of 0.9-14.2 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2.

[0116] In some embodiments, the organic solvent in the composition according to the present application is selected taking into account the boiling point. In at least some embodiments, the boiling point of the organic solvent is ≥ 150°C; preferably ≥ 180°C; more preferably ≥ 200°C; even more preferably ≥ 250°C; most preferably ≥ 300°C. A boiling point in these ranges is beneficial to prevent clogging of the nozzles of the inkjet print head.

[0117] It is appreciated that the organic solvent can be evaporated from the solvent system to form a thin film comprising the organic compound.

[0118] In some embodiments, the composition is a solution. In yet some embodiments, the composition is a suspension. The solution or suspension can further comprise additives for adjusting viscosity, adjusting film forming properties, improving adhesion, etc. The additives can be selected from, but not limited to, at least one of a surface active compound, a lubricant, a wetting agent, a dispersing agent, a hydrophobic agent, and a bonding agent.

[0119] The content of the organic compound or mixture in the composition is 0.01-10 wt%, preferably 0.1-5 wt%, more preferably 0.2-5 wt%, and most preferably 0.25-3 wt%.

[0120] The present application also relates to the use of the composition as a coating or printing ink in the preparation of an organic electronic device. In some embodiments, the composition is used in the preparation of an organic electronic device by a printing or coating method. The printing or coating method can be, but is not limited to, inkjet printing, gravure printing, inkjet printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse-roller printing, offset lithography printing, flexographic printing, rotogravure printing, spray coating, brush coating, pad printing, slit extrusion coating, etc. Preferred are gravure printing, inkjet printing, and inkjet printing.

[0121] The present application also relates to the use of an organic compound, mixture, or composition as described above in an organic electronic device. In particular, the organic electronic device comprises at least one functional layer comprising at least one organic compound or mixture as described above, or is prepared from the composition described above.

[0122] An organic electronic device comprises at least one functional layer. The functional layer comprises at least one organic compound or mixture as described above, or is prepared from the composition described above.

[0123] Further, the organic electronic device comprises a cathode, an anode, and at least one functional layer. The functional layer comprises at least one organic compound or mixture as described above, or is prepared from the composition described above.

[0124] The functional layer can be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer, an electron blocking layer, an electron injection layer (EIL), an electron transport layer (ETL), or a hole blocking layer. Preferably, the functional layer is an emitting layer.

[0125] The organic electronic device can be, but is not limited to, an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, an organic spintronics device, an organic sensor, and an organic plasmon emitting diode (Organic Plasmon Emitting Diode), etc. Particularly preferred are OLEDs, organic light emitting field effect transistors, and the like. Further particularly preferred are OLEDs.

[0126] In one embodiment, the organic electronic device comprises a substrate and, in the order given, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode. The light emitting layer comprises at least one organic compound or mixture as described above, or the light emitting layer is prepared from a composition as described above. It is understood that the structure of the organic electronic device is not limited to this.

[0127] The substrate can be transparent or non-transparent. A transparent substrate can be used to make a transparent light emitting device. See, for example, Bulovic et al. Nature 1996, 380, p29, and Gu et al. Appl. Phys. Lett. 1996, 68, p2606. The substrate can also be rigid or flexible. In some embodiments, the substrate is plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface, and substrates without surface defects are particularly desirable. In a preferred embodiment, the substrate is flexible, and can be selected from polymeric films or plastics having a glass transition temperature Tg of 150°C or higher, preferably 200°C or higher, more preferably 250°C or higher, and most preferably 300°C or higher. Examples of suitable flexible substrates are poly(ethylene terephthalate) (PET) and polyethylene glycol 2,6-napthalate (PEN).

[0128] The anode is a hole-injecting electrode, and the anode can easily inject holes into a hole-injection layer, or a hole-transport layer, or a light-emitting layer. The anode can comprise a conductive metal, a conductive metal oxide, or a conductive polymer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or the valence band level of the light-emitter in the light-emitting layer or the HOMO level of a p-type semiconductor material as a HIL or a HTL or an electron-blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known to those skilled in the art and can be readily selected for use. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio-frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate devices according to the present application. The cathode is an electron-injecting electrode, and the cathode can easily inject electrons into an electron-injection layer, or an electron-transport layer, or a light-emitting layer. The cathode can comprise a conductive metal or a conductive metal oxide. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or the conduction band level of the light-emitter in the light-emitting layer or the LUMO level of an n-type semiconductor material as an electron-injection layer (EIL) or an electron-transport layer (ETL) or a hole-blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. In principle, all materials that can be used as a cathode of an organic electronic device can be used as a cathode material of a device according to the present application. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio-frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like.

[0129] The hole-injection layer is a layer for facilitating injection of holes from the anode to the light-emitting layer, and the hole-injection material is a material that can proficiently receive holes injected from the positive electrode at a low voltage, and preferably, the highest occupied molecular orbital (HOMO) of the hole-injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole-injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexacyno-hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline-based and polythiophene-based conductive polymer, and the like, but are not limited thereto.

[0130] The hole transport layer can be used to smoothly transport holes. The hole transport material for the hole transport layer known in the art is suitably a material having a high hole mobility, which can receive holes transported from the anode or hole injection layer and transfer the holes to the light emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions, etc., but are not limited thereto.

[0131] The electron blocking layer can be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, a spiroindolacridine-based compound or a material known in the art can be used.

[0132] The light emitting layer can emit red, green, or blue light, and can be composed of a phosphorescent material or a fluorescent material. The light emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region, and is preferably a material having a good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimer styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole-based, benzothiazole-based, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; rubrene, etc., but are not limited thereto.

[0133] Examples of the host material for the light emitting layer include fused aromatic ring derivatives or heterocycle-containing compounds, etc. Specifically, examples of the fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of the heterocycle-containing compounds include carbazole derivatives, diphenylfuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but examples thereof are not limited thereto.

[0134] When the light-emitting layer emits red light, the following can be used as the light-emitting dopant: phosphorescent materials such as bis(l-phenylisoquinoline)acetylacetone iridium (PIQIr(acac)), bis(l-phenylquinoline)acetylacetone iridium (PQIr(acac)), tris(l-phenylquinoline)iridium (PQIr), or octaethylporphyrin platinum (PtOEP); or fluorescent materials such as tris(8-hydroxyquinoline)aluminum (Alq3), but the light-emitting dopant is not limited thereto. When the light-emitting layer emits green light, phosphorescent materials such as fac-tris(2-phenylpyridine)iridium (Ir(ppy)3) or fluorescent materials such as tris(8-hydroxyquinoline)aluminum (Alq3) can be used as the light-emitting dopant, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits blue light, the following can be used as the light-emitting dopant: phosphorescent materials such as (4,6-F2ppy)2Irpic; or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), a PFO-based polymer, or a PPV-based polymer, but the light-emitting dopant is not limited thereto.

[0135] The electron transport layer can be used to smoothly transport electrons. The electron transport material is suitably a material having a high electron mobility, which can receive electrons injected from the negative electrode and transfer the electrons to the light-emitting layer. Specific examples thereof can include, but are not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic radical compound, a hydroxyflavone-metal complex, lithium 8-hydroxyquinoline (LiQ), and a benzimidazole-based compound.

[0136] The electron injection layer can be used to smoothly inject electrons. The electron injection material is preferably a material having the ability to transport electrons, having the effect of injecting electrons from the negative electrode, and having an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, preventing excitons generated by the light-emitting layer from moving to the hole injection layer, and also having an excellent ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, and the like and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

[0137] The hole blocking layer is a layer that blocks holes from reaching the negative electrode, and can generally be formed under the same conditions as those of the hole injection layer. Specific examples thereof include diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

[0138] The organic electronic device emits light having a wavelength of between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0139] In one embodiment, the organic electronic device described herein is a solution-processed organic electronic device, wherein one or more functional layers are prepared by printing; further, the solution-processed organic electronic device is a solution-processed OLED.

[0140] The present application also relates to the use of an organic electronic device according to the present application in various electronic devices, which can be, but are not limited to, display devices, lighting devices, light sources, sensors, etc.

[0141] The present application also relates to electronic devices comprising the organic electronic device. The electronic devices can be, but are not limited to, display devices, lighting devices, light sources, sensors, etc.

[0142] The present application will be described in more detail by specific working examples. The following examples are only a part of the present application and are not a limitation of the present application. Specific embodiments

[0144] Example 1

[0145] The synthetic route of the organic compound 1 of the present example is as follows:

[0146]

[0147] Synthesis of intermediate 1-1:

[0148] Weigh 12,13-dihydro-12,12-dimethylindeno[2,1-a]phenoxazine (10 g, 33 mmol), iodobenzene (13.6 g, 69 mmol), Pd2(dba)3(tris(dibenzylideneacetone)dipalladium, 0.61 g, 0.67 mmol), t-Bu3P(tri-tert-butylphosphine, 0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE) to obtain white solid, which is intermediate 1-1, with a yield of 92%, MS (ASAP) = 375.2.

[0149] Synthesis of intermediate 1-2:

[0150] Weigh intermediate 1-1 (10 g, 26.6 mmol) in a 500 ml two-necked flask, add 200 ml of DMF until the solid is completely dissolved, weigh NBS(N-bromosuccinimide, 4.8 g, 26.6 mmol) in a constant pressure dropping funnel, dissolve with 100 ml of DMF(N,N-dimethylformamide), slowly drop, and react at room temperature for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE) to obtain white solid, which is intermediate 1-2, with a yield of 88%, MS (ASAP) = 453.1.

[0151] Synthesis of intermediate 1-3:

[0152] A dry 500 mL three-necked flask was prepared and the reaction apparatus was set up and evacuated and flushed with nitrogen. The flask was kept under a stream of nitrogen and 1,4-dibromobenzene (10 g, 42.6 mmol) was weighed in and THF (250 ml) was added. The flask was evacuated and flushed with nitrogen three times and cooled to -78 °C. n-Butyllithium solution (17.4 ml, 42.6 mmol) was added slowly to the flask and the reaction was allowed to proceed for 30 min at -78 °C. Dimethoxydiphenylsilane (10.4 g, 42.6 mmol) was added quickly to the flask. The reaction was allowed to warm up slowly to room temperature and was left to react for 12 h. Water was added and DCM was used to extract the product. The solvent was evaporated and the product was purified by column chromatography (eluent: PE) to give intermediate 1-3 as a colourless oil in 41% yield, MS (ASAP) = 368.0.

[0153] Synthesis of intermediate 1-4:

[0154] A dry 250 mL three-necked flask was prepared and the reaction apparatus was set up and evacuated and flushed with nitrogen. The flask was kept under a stream of nitrogen and intermediate 1-2 (6.0 g, 13 mmol) was weighed in and THF (100 ml) was added. The flask was evacuated and flushed with nitrogen three times and cooled to -78 °C. n-Butyllithium solution (5.3 ml, 13 mmol) was added slowly to the flask and the reaction was allowed to proceed for 60 min at -78 °C. Intermediate 1-3 (4.9 g, 13 mmol) was added quickly to the flask. The reaction was allowed to warm up slowly to room temperature and was left to react for 12 h. Water was added and DCM was used to extract the product. The solvent was evaporated and the product was purified by trituration with PE to give intermediate 1-4 as a white solid in 53% yield, MS (ASAP) = 711.2.

[0155] Synthesis of intermediate 1-5:

[0156] Intermediate 1-4 (7.1 g, 10 mmol), (Bpin)2 (3.8 g, 15 mmol), AcOK (potassium acetate, 9.8 g, 100 mmol), Pd(dppf)Cl2 (1,1'-bis(diphenylphosphino)ferrocene palladium(II) chloride, 0.74 g, 1.0 mmol) were weighed into a 250 mL three-necked flask and 100 ml of 1,4-dioxane was added. The flask was replaced with nitrogen and the reaction was left to proceed at 100 °C for 12 h. The solvent was evaporated and the product was purified by column chromatography (eluent: PE:DCM = 5:1) to give intermediate 1-5 as a white solid in 87% yield, MS (ASAP) = 759.3.

[0157] Synthesis of organic compound 1:

[0158] Take intermediate 1-5 (5.3 g, 7.0 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5 triazine (3.8 g, 14 mmol), K2CO3(12.8 g, 93 mmol), Pd(PPh3)4 (tetra (triphenylphosphine) palladium, 1.1 g, 0.93 mmol) in a 250 mL three-necked flask, add 100 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, 100 ℃ for 12 h. Spin dry, water washing, column chromatography (eluent is PE:DCM = 3:1) to get white solid, that is organic compound 1, the yield is 58%, MS (ASAP) = 864.3.

[0159] Example 2

[0160] The synthetic route of the organic compound 2 of the present example is as follows:

[0161]

[0162] Synthesis of intermediate 2-1:

[0163] Prepare a dry 500 mL three-necked flask, build a reaction device to vacuum, nitrogen circulation; keep the nitrogen flow in the reaction bottle, take 1, 4-dibromobenzene (10 g, 42.6 mmol), and add THF (250 ml), vacuum and nitrogen circulation three times, cool to-78 ℃; slowly drop the n-butyllithium solution (17.4 ml, 42.6 mmol) into the reaction bottle, -78 ℃ for 30 min, then quickly add dimethoxydi (4-tert-butylphenyl) silane (15 g, 42.6 mmol). Let the reaction system slowly rise to room temperature, react for 12 h. Add water, extract with DCM, spin dry the solvent, then use column chromatography (eluent is PE) to get colorless oil, that is intermediate 2-1, the yield is 33%, MS (ASAP) = 480.2.

[0164] Synthesis of intermediate 2-2:

[0165] Prepare a dry 250 mL three-necked flask, build a reaction device to vacuum, nitrogen circulation; keep the nitrogen flow in the reaction bottle, take intermediate 1-2 (4.5 g, 10 mmol), and add THF (100 ml), vacuum and nitrogen circulation three times, cool to-78 ℃; slowly drop the n-butyllithium solution (4.0 ml, 10 mmol) into the reaction bottle, -78 ℃ for 60 min, then quickly add intermediate 2-1 (4.8 g, 10 mmol). Let the reaction system slowly rise to room temperature, react for 12 h. Add water, extract with DCM, spin dry the solvent, then use PE to beat the pulp to get white solid, that is intermediate 2-2, the yield is 56%, MS (ASAP) = 823.3.

[0166] Synthesis of intermediate 2-3:

[0167] Take intermediate 2-2 (5 g, 7.1 mmol), (Bpin)2(2.2 g, 8.5 mmol), AcOK (7.0 g, 71 mmol), Pd(dppf)Cl2(0.74 g, 1.0 mmol), t-Bu3P (0.39 g, 1.94 mmol) in a 250 mL three-necked flask, add 100 ml of 1,4-dioxane, replace nitrogen, react at 100 ℃ for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 5:1) to obtain colorless oil, intermediate 2-3, yield 82%, MS (ASAP) = 871.5.

[0168] Synthesis of organic compound 2:

[0169] Take intermediate 2-3 (5 g, 5.7 mmol), 2-chloro-4,6-diphenyl-1,3,5 triazine (3.5 g, 13 mmol), K2CO3(9.1 g, 66 mmol), Pd(PPh3)4(0.77 g, 0.66 mmol) in a 250 mL three-necked flask, add 100 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100 ℃ for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 3:1) to obtain white solid, organic compound 2, yield 42%, MS (ASAP) = 976.5.

[0170] Example 3

[0171] The synthesis route of organic compound 3 of this example is as follows:

[0172]

[0173] Synthesis of intermediate 3-1:

[0174] Take 8,13-dihydro-8,8-dimethylindeno[1,2-a]phenoxazine (10 g, 33 mmol), iodobenzene (13.6 g, 69 mmol), Pd2(dba)3(0.61 g, 0.67 mmol), t-Bu3P (0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, react at 80 ℃ for 12 h. Spin dry, wash with water, column chromatography (eluent is PE) to obtain white solid, intermediate 3-1, yield 95%, MS (ASAP) = 375.2.

[0175] Synthesis of intermediate 3-2:

[0176] In a 500ml flask, put intermediate 3-1 (8g, 21mmol), add 200ml of DMF until the solid is completely dissolved, weigh NBS (3.8g, 21mmol) and put it in a constant pressure dropping funnel, dissolve it in 100ml of DMF, slowly drop, and react at room temperature for 12h. Spin dry, wash with water, and column chromatography (eluent is PE) to obtain white solid, intermediate 3-2, yield is 82%, MS (ASAP) = 453.1.

[0177] Synthesis of intermediate 3-3:

[0178] Prepare a dry 500ml three-necked flask, build a reaction device, vacuumize, and circulate nitrogen; keep the nitrogen flowing in the reaction flask, weigh 1,3-dibromobenzene (20g, 84.7mmol), and add THF (250ml), vacuumize and circulate nitrogen three times, and cool to -78℃; slowly drop n-butyllithium solution (35ml, 85mmol) into the reaction flask, react at -78℃ for 30min, and then quickly add dimethoxydiphenylsilane (20.7g, 85mmol). Slowly raise the reaction system to room temperature, and react for 12h. Add water, extract with DCM, spin dry the solvent, and then use column chromatography (eluent is PE) to obtain colorless oil, intermediate 3-3, yield is 46%, MS (ASAP) = 368.0.

[0179] Synthesis of intermediate 3-4:

[0180] Prepare a dry 250ml three-necked flask, build a reaction device, vacuumize, and circulate nitrogen; keep the nitrogen flowing in the reaction flask, weigh intermediate 3-2 (4.0g, 8.8mmol), and add THF (100ml), vacuumize and circulate nitrogen three times, and cool to -78℃; slowly drop n-butyllithium solution (3.5ml, 8.8mmol) into the reaction flask, react at -78℃ for 60min, and then quickly add intermediate 3-3 (3.3g, 8.8mmol). Slowly raise the reaction system to room temperature, and react for 12h. Add water, extract with DCM, spin dry the solvent, and then use PE to obtain white solid, intermediate 3-4, yield is 55%, MS (ASAP) = 711.2.

[0181] Synthesis of intermediate 3-5:

[0182] Take intermediate 3-4 (7.1 g, 10 mmol), (Bpin)2(3.8 g, 15 mmol), AcOK (9.8 g, 100 mmol), Pd(dppf)Cl2(0.74 g, 1.0 mmol) in a 250 mL three-necked flask, add 100 ml of 1,4-dioxane, replace nitrogen, react at 100°C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 5:1) to obtain white solid, which is intermediate 3-5, the yield is 76%, MS (ASAP) = 759.3.

[0183] Synthesis of organic compound 3:

[0184] Take intermediate 3-5 (5.9 g, 7.8 mmol), 2-chloro-4,6-diphenyl-1,3,5 triazine (4.1 g, 16 mmol), K2CO3(11 g, 78 mmol), Pd(PPh3)4(0.9 g, 0.78 mmol) in a 250 mL three-necked flask, add 100 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100°C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 3:1) to obtain white solid, which is organic compound 3, the yield is 53%, MS (ASAP) = 864.3.

[0185] Example 4

[0186] The synthesis route of organic compound 4 of this example is as follows:

[0187]

[0188] Synthesis of intermediate 4-1:

[0189] Take 11,13-dihydro-11,11-dimethylindeno[2,1-b]phenoxazine (10 g, 33 mmol), iodobenzene (13.6 g, 69 mmol), Pd2(dba)3(0.61 g, 0.67 mmol), t-Bu3P (0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, react at 80°C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE) to obtain white solid, which is intermediate 4-1, the yield is 87%, MS (ASAP) = 375.2.

[0190] Synthesis of intermediate 4-2:

[0191] In a 500ml flask, put intermediate 4-1 (12g, 32mmol), add 200ml of DMF until the solid is completely dissolved, weigh NBS (5.7g, 32mmol) into a constant pressure dropping funnel, dissolve with 100ml of DMF, slowly drop, and react at room temperature for 12h. Spin dry, wash with water, and column chromatography (eluent is PE) to obtain white solid, intermediate 4-2, yield is 81%, MS (ASAP) = 453.1.

[0192] Synthesis of intermediate 4-3:

[0193] Prepare a dry 250ml three-necked flask, set up the reaction device, vacuumize, and circulate nitrogen; keep the nitrogen flowing in the reaction flask, weigh intermediate 4-2 (5.0g, 11mmol), and add THF (100ml), vacuumize and circulate nitrogen three times, and cool to -78℃; slowly drop n-butyllithium solution (4.4ml, 11mmol) into the reaction flask, react at -78℃ for 60min, and then quickly add intermediate 3-3 (4.1g, 11mmol). Slowly raise the reaction system to room temperature, and react for 12h. Add water, extract with DCM, spin dry the solvent, and then use PE to make a slurry to obtain white solid, intermediate 4-3, yield is 42%, MS (ASAP) = 711.2.

[0194] Synthesis of intermediate 4-4:

[0195] Weigh intermediate 4-3 (5g, 7.0mmol), (Bpin)2 (3.6g, 14mmol), AcOK (3.4g, 35mmol), Pd(dppf)Cl2 (0.8g, 0.7mmol) into a 250ml three-necked flask, add 100ml of 1,4-dioxane, replace nitrogen, and react at 100℃ for 12h. Spin dry, wash with water, and column chromatography (eluent is PE:DCM = 5:1) to obtain white solid, intermediate 4-4, yield is 76%, MS (ASAP) = 759.3.

[0196] Synthesis of organic compound 4:

[0197] Weigh intermediate 4-4 (8g, 11mmol), 2-chloro-4,6-diphenyl-1,3,5 triazine (5.6g, 21mmol), K2CO3 (7.6g, 55mmol), Pd(PPh3)4 (1.3g, 1.1mmol) into a 250ml three-necked flask, add 100ml of toluene, 50ml of ethanol, and 50ml of water, replace nitrogen, and react at 100℃ for 12h. Spin dry, wash with water, and column chromatography (eluent is PE:DCM = 3:1) to obtain white solid, organic compound 4, yield is 42%, MS (ASAP) = 864.3.

[0198] Example 5

[0199] The synthetic route of the organic compound 5 of the present example is as follows:

[0200]

[0201] Synthesis of intermediate 5-1:

[0202] Put 7,13-dihydro-7,7-dimethylindeno[1,2-b]phenoxazine (10 g, 33 mmol), iodobenzene (13.6 g, 69 mmol), Pd2(dba)3(0.61 g, 0.67 mmol), t-Bu3P (0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80 °C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE) to obtain white solid, which is intermediate 5-1, with a yield of 94%, MS (ASAP) = 375.2.

[0203] Synthesis of intermediate 5-2:

[0204] Put intermediate 5-1 (5.5 g, 15 mmol) in a 500 ml two-necked flask, add 200 ml of DMF until the solid is completely dissolved, weigh NBS (2.6 g, 15 mmol) and place it in a constant pressure dropping funnel, dissolve it with 100 ml of DMF, slowly drop, and react at room temperature for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE) to obtain white solid, which is intermediate 5-2, with a yield of 78%, MS (ASAP) = 453.1.

[0205] Synthesis of intermediate 5-3:

[0206] Prepare a dry 250 mL three-necked flask, set up the reaction device, vacuumize, and pass nitrogen; keep the nitrogen flowing in the reaction bottle, weigh intermediate 5-2 (5.0 g, 11 mmol), and add THF (100 ml), vacuumize and circulate nitrogen three times, and cool to -78 °C; slowly drop n-butyllithium solution (4.4 ml, 11 mmol) into the reaction bottle, react at -78 °C for 60 min, and then quickly add intermediate 3-3 (4.1 g, 11 mmol). Slowly raise the reaction system to room temperature, react for 12 h, add water, extract with DCM, spin dry the solvent, and then use PE to make a slurry to obtain white solid, which is intermediate 5-3, with a yield of 38%, MS (ASAP) = 711.2.

[0207] Synthesis of intermediate 5-4:

[0208] Take intermediate 5-3 (5 g, 7.0 mmol), (Bpin)2(3.6 g, 14 mmol), AcOK (3.4 g, 35 mmol), Pd(dppf)Cl2(0.8 g, 0.7 mmol) in a 250 mL three-necked flask, add 100 ml of 1,4-dioxane, replace nitrogen, react at 100 ℃ for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 5:1) to obtain white solid, which is intermediate 5-4, the yield is 76%, MS (ASAP) = 759.3.

[0209] Synthesis of organic compound 5:

[0210] Take intermediate 4-4 (7.6 g, 10 mmol), 4-chloro-2-phenyl-6-naphthyl-1,3,5 triazine (6.3 g, 20 mmol), K2CO3(6.9 g, 50 mmol), Pd(PPh3)4(1.1 g, 1.0 mmol) in a 250 mL three-necked flask, add 100 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100 ℃ for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 3:1) to obtain white solid, which is organic compound 5, the yield is 52%, MS (ASAP) = 914.3.

[0211] Example 6

[0212] The synthesis route of organic compound 6 of this example is as follows:

[0213]

[0214] Synthesis of intermediate 6-1:

[0215] Take 5,8-dihydro-8,8-dimethylindeno[2,1-c]phenoxazine (10 g, 33 mmol), iodobenzene (13.6 g, 69 mmol), Pd2(dba)3(0.61 g, 0.67 mmol), t-Bu3P (0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, react at 80 ℃ for 12 h. Spin dry, wash with water, column chromatography (eluent is PE) to obtain white solid, which is intermediate 6-1, the yield is 94%, MS (ASAP) = 375.2.

[0216] Synthesis of intermediate 6-2:

[0217] In a 500ml flask, put intermediate 6-1 (5.5g, 15mmol), add 200ml DMF until the solid is completely dissolved, weigh NBS (2.6g, 15mmol) and dissolve in 100ml DMF, slowly drop, and react at room temperature for 12h. Spin dry, wash with water, and column chromatography (eluent PE) to obtain white solid, intermediate 6-2, yield 83%, MS (ASAP) = 453.1.

[0218] Synthesis of intermediate 6-3:

[0219] Prepare a dry 250ml three-necked flask, set up the reaction device, vacuumize, and circulate nitrogen; keep the nitrogen flowing in the reaction flask, weigh intermediate 6-2 (4.5g, 9.9mmol), and add THF (100ml), vacuumize and circulate nitrogen three times, and cool to -78℃; slowly drop n-butyllithium solution (4.0ml, 9.9mmol) into the reaction flask, and react at -78℃ for 60min, then quickly add intermediate 1-3 (3.7g, 9.9mmol). Slowly raise the reaction system to room temperature, and react for 12h. Add water, extract with DCM, spin dry the solvent, and then use PE to obtain white solid, intermediate 6-3, yield 32%, MS (ASAP) = 711.2.

[0220] Synthesis of intermediate 6-4:

[0221] Weigh intermediate 6-3 (5g, 7.0mmol), (Bpin)2 (3.6g, 14mmol), AcOK (3.4g, 35mmol), Pd(dppf)Cl2 (0.8g, 0.7mmol) into a 250ml three-necked flask, add 100ml 1,4-dioxane, replace nitrogen, and react at 100℃ for 12h. Spin dry, wash with water, and column chromatography (eluent PE:DCM = 5:1) to obtain white solid, intermediate 6-4, yield 73%, MS (ASAP) = 759.3.

[0222] Synthesis of organic compound 6:

[0223] Weigh intermediate 6-4 (7.6g, 10mmol), 4-chloro-2-phenyl-6-biphenyl-1,3,5 triazine (6.9g, 20mmol), K2CO3 (6.9g, 50mmol), Pd(PPh3)4 (1.1g, 1.0mmol) into a 250ml three-necked flask, add 100ml toluene, 50ml ethanol, and 50ml water, replace nitrogen, and react at 100℃ for 12h. Spin dry, wash with water, and column chromatography (eluent PE:DCM = 3:1) to obtain white solid, organic compound 6, yield 52%, MS (ASAP) = 940.4.

[0224] Example 7

[0225] The synthetic route of the organic compound 7 of the present example is as follows:

[0226]

[0227] Synthesis of intermediate 7-1:

[0228] Take 5,12-dihydro-12,12-dimethylindeno[1,2-c]phenoxazine (10 g, 33 mmol), iodobenzene (13.6 g, 69 mmol), Pd2(dba)3(0.61 g, 0.67 mmol), t-Bu3P (0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent is PE) to obtain white solid, which is intermediate 7-1, with a yield of 89%, MS (ASAP) = 375.2.

[0229] Synthesis of intermediate 7-2:

[0230] Place intermediate 7-1 (10 g, 27 mmol) in a 500 ml two-necked flask, add 200 ml of DMF until the solid is completely dissolved, take NBS (4.8 g, 27 mmol) and place it in a constant pressure dropping funnel, dissolve it with 100 ml of DMF, slowly drop, and react at room temperature for 12 h. Spin dry, wash with water, and column chromatography (eluent is PE) to obtain white solid, which is intermediate 7-2, with a yield of 89%, MS (ASAP) = 453.1.

[0231] Synthesis of intermediate 7-3:

[0232] Prepare a dry 250 mL three-necked flask, set up the reaction device, vacuumize, and pass nitrogen; keep the nitrogen flowing in the reaction bottle, take intermediate 7-2 (5.8 g, 13 mmol), and add THF (100 ml), vacuumize and circulate nitrogen three times, and cool to -78°C; slowly drop n-butyllithium solution (5.1 ml, 13 mmol) into the reaction bottle, react at -78°C for 60 min, and then quickly add intermediate 1-3 (4.7 g, 13 mmol). Let the reaction system slowly warm up to room temperature, react for 12 h. Add water, extract with DCM, spin dry the solvent, and then use PE to make a slurry to obtain white solid, which is intermediate 7-3, with a yield of 28%, MS (ASAP) = 711.2.

[0233] Synthesis of intermediate 7-4:

[0234] Take intermediate 7-3 (5 g, 7.0 mmol), (Bpin)2(3.6 g, 14 mmol), AcOK (3.4 g, 35 mmol), Pd(dppf)Cl2(0.8 g, 0.7 mmol) in a 250 mL three-necked flask, add 100 ml of 1,4-dioxane, replace nitrogen, react at 100°C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 5:1) to obtain white solid, which is intermediate 7-4, the yield is 62%, MS (ASAP) = 759.3.

[0235] Synthesis of organic compound 7:

[0236] Take intermediate 7-4 (7.6 g, 10 mmol), 4-chloro-2-phenyl-6-(2-dibenzofuran)-1,3,5 triazine (7.1 g, 20 mmol), K2CO3(6.9 g, 50 mmol), Pd(PPh3)4(1.1 g, 1.0 mmol) in a 250 mL three-necked flask, add 100 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100°C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 3:1) to obtain white solid, which is organic compound 7, the yield is 48%, MS (ASAP) = 954.3.

[0237] Example 8

[0238] The synthesis route of organic compound 8 of the present example is as follows:

[0239]

[0240] Synthesis of intermediate 8-1:

[0241] Take 5,12-dihydro-12,12-dimethylindeno[1,2-c]phenoxazine (10 g, 33 mmol), p-tert-butyl bromobenzene (14 g, 67 mmol), Pd2(dba)3(0.61 g, 0.67 mmol), t-Bu3P (0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, react at 80°C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE) to obtain white solid, which is intermediate 8-1, the yield is 89%, MS (ASAP) = 431.2.

[0242] Synthesis of intermediate 8-2:

[0243] In a 500ml flask, put intermediate 8-1 (10g, 23mmol), add 200ml DMF until the solid is completely dissolved, weigh NBS (4.1g, 23mmol) and dissolve in 100ml DMF, slowly drop, and react at room temperature for 12h. Spin dry, wash with water, and column chromatography (eluent PE) to obtain white solid, intermediate 8-2, yield 87%, MS (ASAP) = 509.1.

[0244] Synthesis of intermediate 8-3:

[0245] Prepare a dry 250ml three-necked flask, set up the reaction device, vacuumize, and circulate nitrogen; keep the nitrogen flowing in the reaction flask, weigh intermediate 8-2 (5.8g, 11mmol), and add THF (100ml), vacuumize and circulate nitrogen three times, and cool to -78℃; slowly drop n-butyllithium solution (4.5ml, 11mmol) into the reaction flask, and react at -78℃ for 60min, then quickly add intermediate 1-3 (4.2g, 11mmol). Slowly raise the reaction system to room temperature, and react for 12h. Add water, extract with DCM, spin dry the solvent, and then use PE to make a slurry to obtain white solid, intermediate 8-3, yield 28%, MS (ASAP) = 767.2.

[0246] Synthesis of intermediate 8-4:

[0247] Weigh intermediate 8-3 (3g, 3.9mmol), (Bpin)2 (2.0g, 7.8mmol), AcOK (3.8g, 39mmol), Pd(dppf)Cl2 (0.29g, 0.4mmol) into a 250ml three-necked flask, add 100ml 1,4-dioxane, replace nitrogen, and react at 100℃ for 12h. Spin dry, wash with water, and column chromatography (eluent PE:DCM = 5:1) to obtain white solid, intermediate 8-4, yield 64%, MS (ASAP) = 688.3.

[0248] Synthesis of organic compound 8:

[0249] Weigh intermediate 8-4 (3.2g, 4.7mmol), 4-chloro-2,6-di(3-pyridyl)-1,3,5 triazine (2.5g, 9.3mmol), K2CO3 (6.5g, 47mmol), Pd(PPh3)4 (0.54g, 0.47mmol) into a 250ml three-necked flask, add 100ml toluene, 50ml ethanol, and 50ml water, replace nitrogen, and react at 100℃ for 12h. Spin dry, wash with water, and column chromatography (eluent PE:DCM = 3:1) to obtain white solid, organic compound 8, yield 43%, MS (ASAP) = 922.4.

[0250] Example 9

[0251] The synthetic route of the organic compound 9 of this example is as follows:

[0252]

[0253] Synthesis of the organic compound 9:

[0254] Take intermediate 2-3 (5 g, 5.7 mmol), 4-chloro-2-phenyl-6-(3-phenanthryl)-1,3,5 triazine (4.2 g, 11.5 mmol), K2CO3 (7.9 g, 57 mmol), Pd(PPh3)4 (0.66 g, 0.57 mmol) in a 250 mL three-necked flask, add 150 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100 °C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 3:1) to get white solid, which is the organic compound 9, the yield is 49%, MS (ASAP) = 1076.5.

[0255] Example 10

[0256] The synthetic route of the organic compound 10 of this example is as follows:

[0257]

[0258] Synthesis of the organic compound 10:

[0259] Take intermediate 4-4 (5 g, 5.7 mmol), 10-1 (3.0 g, 11.4 mmol), K2CO3 (3.9 g, 28.5 mmol), Pd(PPh3)4 (0.66 g, 0.57 mmol) in a 250 mL three-necked flask, add 150 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100 °C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 3:1) to get white solid, which is the organic compound 10, the yield is 51%, MS (ASAP) = 864.3.

[0260] Example 11

[0261] The synthetic route of the organic compound 11 of this example is as follows:

[0262]

[0263] Synthesis of the organic compound 11:

[0264] Take intermediate 2-3 (8 g, 9.2 mmol), 4-chloro-2-(2-naphthalenyl)-6- phenylpyrimidine (5.8 g, 18 mmol), K2CO3(6.3 g, 46 mmol), Pd(PPh3)4(1.1 g, 0.92 mmol) in a 250 mL three-necked flask, add 150 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100 °C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 3:1) to obtain white solid, which is organic compound 11, the yield is 43%, MS (ASAP) = 1025.5.

[0265] Example 12

[0266] The synthetic route of organic compound 12 of this example is as follows:

[0267]

[0268] Synthesis of organic compound 12:

[0269] Take intermediate 7-4 (7.6 g, 10 mmol), 2-chloro-4,6-di(4-tert-butylphenyl)- 1,3,5 triazine (7.6 g, 20 mmol), K2CO3(6.9 g, 50 mmol), Pd(PPh3)4(1.1 g, 1.0 mmol) in a 250 mL three-necked flask, add 100 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100 °C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 3:1) to obtain white solid, which is organic compound 12, the yield is 43%, MS (ASAP) = 1032.5.

[0270] Example 13

[0271] The synthetic route of organic compound 13 of this example is as follows:

[0272]

[0273] Synthesis of intermediate 13-1:

[0274] Into a 500 mL three-neck flask, was placed 8,13-dihydro-8,8-dimethylindeno[1,2- a]phenoxazine (10 g, 33 mmol), 2-iodonaphthalene (16.8 g, 66 mmol), Pd2(dba)3 (0.61 g, 0.67 mmol), t-Bu3P (0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol), 200 mL of toluene, and the reaction was purged with nitrogen. The reaction was heated at 80 °C for 12 h. The reaction was concentrated, washed with water, and purified by column chromatography (eluent: PE) to give the white solid, intermediate 13-1, in 91% yield, MS (ASAP) = 427.2.

[0275] Synthesis of intermediate 13-2:

[0276] Into a 500 mL two-neck flask, was placed intermediate 13-1 (10 g, 23 mmol), 200 mL of DMF, and NBS (4.2 g, 23 mmol) dissolved in 100 mL of DMF was added dropwise over a period of 30 min. The reaction was stirred at room temperature for 12 h. The reaction was concentrated, washed with water, and purified by column chromatography (eluent: PE) to give the white solid, intermediate 13-2, in 86% yield, MS (ASAP) = 503.1.

[0277] Synthesis of intermediate 13-3:

[0278] Into a dry 250 mL three-neck flask, was placed intermediate 13-2 (5.0 g, 9.9 mmol), THF (100 mL), and the reaction was purged with nitrogen. The reaction was cooled to -78 °C, and n-BuLi (4.0 mL, 9.9 mmol) was added dropwise. The reaction was stirred at -78 °C for 60 min, and intermediate 1-3 (3.7 g, 9.9 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 12 h. The reaction was quenched with water, extracted with DCM, and the solvent was removed by rotary evaporation. The residue was triturated with PE to give the white solid, intermediate 13-3, in 65% yield, MS (ASAP) = 761.2.

[0279] Synthesis of intermediate 13-4:

[0280] Take intermediate 13-3 (7.6 g, 10 mmol), (Bpin)2(3.8 g, 15 mmol), AcOK (9.8 g, 100 mmol), Pd(dppf)Cl2(0.74 g, 1.0 mmol) in a 250 mL three-necked flask, add 100 ml of 1,4-dioxane, replace nitrogen, react at 100°C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 5:1) to obtain white solid, which is intermediate 13-4, the yield is 73%, MS (ASAP) = 809.4.

[0281] Synthesis of organic compound 13:

[0282] Take intermediate 13-4 (5.9 g, 7.3 mmol), 4-chloro-2-phenyl-6-(3-(9,9-dimethylfluorene))-1,3,5 triazine (6.1 g, 16 mmol), K2CO3(10 g, 73 mmol), Pd(PPh3)4(0.84 g, 0.73 mmol) in a 250 mL three-necked flask, add 100 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100°C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 3:1) to obtain white solid, which is organic compound 13, the yield is 51%, MS (ASAP) = 1030.4.

[0283] Example 14

[0284] The synthesis route of organic compound 14 of this example is as follows:

[0285]

[0286] Synthesis of intermediate 14-1:

[0287] Take 7,13-dihydro-7,7-dimethylindeno[1,2-b]phenoxazine (10 g, 33 mmol), 9-iodophenanthrene (20.1 g, 66 mmol), Pd2(dba)3(0.61 g, 0.67 mmol), t-Bu3P (0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, react at 80°C for 12 h. Spin dry, wash with water, column chromatography (eluent is PE) to obtain white solid, which is intermediate 14-1, the yield is 94%, MS (ASAP) = 475.2.

[0288] Synthesis of intermediate 14-2:

[0289] In a 500ml flask, put intermediate 14-1 (6g, 13mmol), add 200ml of DMF until the solid is completely dissolved, weigh NBS (2.2g, 13mmol) and put it in a constant pressure dropping funnel, dissolve it in 100ml of DMF, slowly drop, and react at room temperature for 12h. Spin dry, wash with water, and column chromatography (eluent PE) to obtain white solid, intermediate 14-2, yield 73%, MS (ASAP) = 553.1.

[0290] Synthesis of intermediate 14-3:

[0291] Prepare a dry 500ml three-necked flask, build the reaction device, vacuumize, and circulate nitrogen; keep the nitrogen flowing in the reaction flask, weigh 1,4-dibromobenzene (10g, 42.6mmol), and add THF (250ml), vacuumize and circulate nitrogen three times, and cool to -78℃; slowly drop n-butyllithium solution (17.4ml, 42.6mmol) into the reaction flask, react at -78℃ for 30min, and then quickly add dimethoxybis(4-tolyl)silane (11.5g, 42.6mmol). Slowly raise the reaction system to room temperature, and react for 12h. Add water, extract with DCM, spin dry the solvent, and then use column chromatography (eluent PE) to obtain colorless oil, intermediate 14-3, yield 36%, MS (ASAP) = 396.1.

[0292] Synthesis of intermediate 14-4:

[0293] Prepare a dry 250ml three-necked flask, build the reaction device, vacuumize, and circulate nitrogen; keep the nitrogen flowing in the reaction flask, weigh intermediate 14-2 (5.0g, 9.1mmol), and add THF (100ml), vacuumize and circulate nitrogen three times, and cool to -78℃; slowly drop n-butyllithium solution (3.6ml, 9.1mmol) into the reaction flask, react at -78℃ for 60min, and then quickly add intermediate 14-3 (3.6g, 9.1mmol). Slowly raise the reaction system to room temperature, and react for 12h. Add water, extract with DCM, spin dry the solvent, and then use PE to obtain white solid, intermediate 14-4, yield 43%, MS (ASAP) = 839.2.

[0294] Synthesis of intermediate 14-5:

[0295] Take intermediate 14-4 (5 g, 6.0 mmol), (Bpin)2(3.0 g, 12 mmol), AcOK (3.0 g, 30 mmol), Pd(dppf)Cl2(0.44 g, 0.6 mmol) in a 250 mL three-necked flask, add 100 ml of 1,4-dioxane, replace nitrogen, react at 100 ℃ for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 5:1) to obtain white solid, which is intermediate 14-5, the yield is 73%, MS (ASAP) = 859.4.

[0296] Synthesis of organic compound 14:

[0297] Take intermediate 14-5 (8.6 g, 10 mmol), 2-chloro-4,6-diphenylpyrimidine (5.3 g, 20 mmol), K2CO3(6.9 g, 50 mmol), Pd(PPh3)4(1.1 g, 1.0 mmol) in a 250 mL three-necked flask, add 100 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100 ℃ for 12 h. Spin dry, wash with water, column chromatography (eluent is PE:DCM = 3:1) to obtain white solid, which is organic compound 14, the yield is 57%, MS (ASAP) = 963.4.

[0298] Example 15

[0299] The synthesis route of organic compound 15 of the present example is as follows:

[0300]

[0301] Synthesis of intermediate 15-1:

[0302] Take 11,13-dihydro-11,11-dimethylindeno[2,1-b]phenoxazine (10 g, 33 mmol), 2- bromodibenzothiophene (17.3 g, 66 mmol), Pd2(dba)3(0.61 g, 0.67 mmol), t-Bu3P (0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, react at 80 ℃ for 12 h. Spin dry, wash with water, column chromatography (eluent is PE) to obtain white solid, which is intermediate 15-1, the yield is 89%, MS (ASAP) = 481.2.

[0303] Synthesis of intermediate 15-2:

[0304] In a 500ml flask, put intermediate 15-1 (10g, 21mmol), add 200ml of DMF until the solid is completely dissolved, weigh NBS (3.7g, 21mmol) into a constant pressure dropping funnel, dissolve with 100ml of DMF, slowly drop, and react at room temperature for 12h. Spin dry, wash with water, and column chromatography (eluent is PE) to obtain white solid, intermediate 15-2, yield is 78%, MS (ASAP) = 559.1.

[0305] Synthesis of intermediate 15-3:

[0306] Prepare a dry 250ml three-necked flask, set up the reaction device, vacuumize, and pass nitrogen; keep the nitrogen flowing in the reaction bottle, weigh intermediate 15-2 (5.0g, 8.9mmol), and add THF (100ml), vacuumize and circulate nitrogen three times, and cool to-78℃; slowly drop n-butyllithium solution (3.6ml, 8.9mmol) into the reaction bottle, react at-78℃ for 60min, and then quickly add 1-3 (3.3g, 8.9mmol). Slowly raise the reaction system to room temperature, and react for 12h. Add water, extract with DCM, spin dry the solvent, and then use PE to make a slurry to obtain white solid, intermediate 15-3, yield is 43%, MS (ASAP) = 817.2.

[0307] Synthesis of intermediate 15-4:

[0308] Weigh intermediate 15-3 (5.7g, 7.0mmol), (Bpin)2 (3.6g, 14mmol), AcOK (3.4g, 35mmol), Pd(dppf)Cl2 (0.8g, 0.7mmol) into a 250ml three-necked flask, add 100ml of 1,4-dioxane, replace nitrogen, and react at 100℃ for 12h. Spin dry, wash with water, and column chromatography (eluent is PE:DCM = 5:1) to obtain white solid, intermediate 15-4, yield is 79%, MS (ASAP) = 865.3.

[0309] Synthesis of organic compound 15:

[0310] Take intermediate 15-4 (8.7 g, 10 mmol), 4-chloro-2-phenyl-6-(2- dibenzothiophene)-1, 3, 5 triazine (7.5 g, 20 mmol), K2CO3(6.9 g, 50 mmol), Pd(PPh3)4(1.2 g, 1.0 mmol) in a 250 mL three-necked flask, add 100 ml of toluene, 50 ml of ethanol, 50 ml of water, replace nitrogen, react at 100°C for 12 h. Spin dry, water wash, column chromatography (eluent is PE:DCM = 3:1) to obtain white solid, which is organic compound 15, the yield is 52%, MS (ASAP) = 1076.3.

[0311] Example 16

[0312] The synthetic route of the organic compound 16 of the present example is as follows:

[0313]

[0314] Synthesis of intermediate 16-1:

[0315] Take 5, 8-dihydro-8, 8-dimethylindeno [2, 1-c] phenoxazine (10 g, 33 mmol), 3- bromobiphenyl (15.3 g, 66 mmol), Pd2(dba)3(0.61 g, 0.67 mmol), t-Bu3P (0.16 g, 0.8 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, react at 80°C for 12 h. Spin dry, water wash, column chromatography (eluent is PE) to obtain white solid, which is intermediate 16-1, the yield is 88%, MS (ASAP) = 451.2.

[0316] Synthesis of intermediate 16-2:

[0317] Place intermediate 16-1 (10 g, 22 mmol) in a 500 ml two-necked flask, add 200 ml of DMF until the solid is completely dissolved, take NBS (3.9 g, 22 mmol) and place it in a constant pressure dropping funnel, dissolve with 100 ml of DMF, slowly drop, react at room temperature for 12 h. Spin dry, water wash, column chromatography (eluent is PE) to obtain white solid, which is intermediate 16-2, the yield is 92%, MS (ASAP) = 529.1.

[0318] Synthesis of intermediate 16-3:

[0319] A dry 250 mL three-neck flask was prepared, and the reaction device was set up, vacuumed, and purged with nitrogen; the reaction flask was kept under a nitrogen flow, and intermediate 16-2 (6 g, 11 mmol) was weighed and added to THF (100 ml), which was vacuumed and purged with nitrogen three times, and then cooled to -78 °C; n-butyllithium solution (4.5 ml, 11 mmol) was slowly added to the reaction flask, and after reaction at -78 °C for 60 min, intermediate 1-3 (4.2 g, 11 mmol) was quickly added. The reaction system was slowly warmed to room temperature, and reacted for 12 h. Water was added, and extraction was performed with DCM, and after the solvent was spin-dried, the white solid, intermediate 16-3, was obtained by slurry with PE, with a yield of 43%, MS (ASAP) = 787.2.

[0320] Synthesis of intermediate 16-4:

[0321] Intermediate 16-3 (10 g, 12.7 mmol), (Bpin)2 (3.9 g, 15.2 mmol), AcOK (3.9 g, 40 mmol), Pd(dppf)Cl2 (0.95 g, 1.3 mmol) were weighed into a 250 mL three-neck flask, 100 ml of 1,4-dioxane was added, and the nitrogen was replaced, and the reaction was performed at 100 °C for 12 h. After spin-drying, water washing, and column chromatography (eluent: PE:DCM = 5:1), the white solid, intermediate 16-4, was obtained, with a yield of 83%, MS (ASAP) = 835.4.

[0322] Synthesis of organic compound 16:

[0323] Intermediate 16-4 (8 g, 9.6 mmol), 4-chloro-2-phenyl-6-biphenyl-1,3,5 triazine (6.6 g, 19 mmol), K2CO3 (6.9 g, 50 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol) were weighed into a 250 mL three-neck flask, 100 ml of toluene, 50 ml of ethanol, and 50 ml of water were added, the nitrogen was replaced, and the reaction was performed at 100 °C for 12 h. After spin-drying, water washing, and column chromatography (eluent: PE:DCM = 3:1), the white solid, organic compound 16, was obtained, with a yield of 51%, MS (ASAP) = 1016.4.

[0324] Comparative Example 1

[0325] The organic compound of this comparative example is GD (Ref), and its chemical structural formula is as follows:

[0326]

[0327] Preparation of an OLED device

[0328] The OLED device of the present embodiment comprises HATCN as a hole injection layer material, HT as a hole transport material, GP as an electron blocking layer material, GH as a host material of a light emitting material, the organic compounds in Examples 1-16 and Comparative Examples as a dopant material (GD) of a light emitting material, ET as an electron transport material, and Liq (lithium quinolate) as an electron injection material, and the device structure is ITO / HATCN / HT / GP / GH:GD / ET:Liq / Liq / Al.

[0329] The chemical structures of HATCN, HT, GP, GH, ET and Liq are as follows:

[0330]

[0331] The materials HATCN, HT, GP, GH, GD (ref), ET and Liq are commercially available or their synthesis methods are known in the art.

[0332] The schematic diagram of the OLED device is shown in Figure 1 The schematic diagram of the OLED device is shown in

[0333] The preparation process of the OLED device using the above materials is described in detail below through specific examples.

[0334] Device Example 1

[0335] The method for preparing the OLED device of the present embodiment comprises the following steps:

[0336] 1) Cleaning of the ITO (indium tin oxide) anode layer: clean the ITO conductive glass anode layer, then ultrasonically clean with deionized water, acetone and isopropanol for 15 minutes, and then treat in a plasma cleaner for 5 minutes to increase the electrode work function;

[0337] 2) Forming a hole injection layer: on the ITO anode layer, evaporate the hole injection layer material HATCN by vacuum evaporation, with a thickness of 30 nm and an evaporation rate of 0.2 A / s;

[0338] 3) Forming a hole transport layer: on the hole injection layer, evaporate the hole transport material HT by vacuum evaporation, with a thickness of 60 nm;

[0339] 4) Forming an electron blocking layer: on the hole transport layer, evaporate the electron blocking layer material GP, with a thickness of 10 nm;

[0340] 5) Forming a light-emitting layer: forming a light-emitting layer on the electron resistance layer, GH is a host material, organic compound 1 is a guest material, the mass ratio of GH and organic compound 1 is 100:8, and the thickness is 40 nm.

[0341] 6) Forming an electron transport layer: on the light-emitting layer, an electron transport material ET and Liq are evaporated by vacuum evaporation method, the mass ratio is 5:5, and the thickness is 30 nm;

[0342] 7) Forming an electron injection layer: on the electron transport layer, an electron injection layer Liq is vacuum evaporated, and the thickness is 1 nm;

[0343] 8) Forming a cathode layer: on the electron injection layer, a cathode Al layer is vacuum evaporated, and the thickness is 100 nm.

[0344] Device Examples 2-16

[0345] The device examples 2-16 are basically the same as the device example 1, except that the guest materials of the light-emitting layer of the device examples 2-16 are selected from the organic compounds of the examples 2-16, respectively.

[0346] Device Comparative Examples

[0347] The device comparative examples are basically the same as the device example 1, except that the guest material of the light-emitting layer of the device comparative examples is GD (Ref).

[0348] Performance detection and results

[0349] The current-voltage (J-V) characteristics of the OLED devices of the device examples 1-16 and the comparative examples were tested by using the characterization equipment, and important parameters such as luminous efficiency and lifetime were recorded. Among them, the luminous efficiency is the relative value obtained when the current density is 10 mA / cm 2 The lifetime is the time when the luminance decreases to 95% of the initial luminance @1000nits under a constant current of 10 mA / cm 2 In this application, the LT95 and the external quantum efficiency are calculated relative to the OLED-Ref-1 device of the comparative example 1, that is, the lifetime of the device of the comparative example 1 is 1, and the external quantum efficiency is 100%. The luminous efficiency and the lifetime of the OLED devices of the device examples 1-16 are relative to the OLED devices of the device comparative examples. The detection results are shown in Table 1.

[0350] Table 1:

[0351]

[0352]

[0353] As shown in Table 1, compared with the OLED device of the comparative example, the OLED device of the present application examples 1-16 has higher efficiency and longer lifetime.

[0354] The organic compound of the present application has a D-A system, and when applied to an organic electronic device as a green light host material, can effectively improve the efficiency and lifetime of the organic electronic device.

[0355] The organic compound, mixture, composition and organic electronic device provided by the present application are described in detail above, and the principles and implementation modes of the present application are described by applying specific examples; the above examples are only used to help understand the method of the present application and its core idea; at the same time, for those skilled in the art, according to the idea of the present application, the specific implementation mode and application range will be changed; in view of the above, the content of the specification should not be understood as a limitation of the present application.

Claims

1. An organic compound, characterized in that, It has a structure as shown in general formula (I): (I) Where: m is 4; Ar1, Ar2, and Ar3 are independently selected from any one of the following groups: ； Each time X appears, it is independently selected from CR7 or N; Each occurrence of Y is independently selected from CR8R9, O, or S; R7 is selected from -H, phenyl, or tert-butyl; R8 and R9 are selected from methyl groups; X1, X2, and X3 are independently selected from CH or N, and at least one of X1, X2, and X3 is selected from N; Each occurrence of R1 and R2 is independently selected from: -H and tert-butyl, respectively. R3 and R4 are selected from methyl groups; R5 is selected from -H.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from the structures shown in general formulas (III-1)-(III-6): 。 3. The organic compound according to claim 1, characterized in that, Ar1, Ar2, and Ar3 are independently selected from the following groups: 。 4. The organic compound according to claim 1, characterized in that, Each occurrence of Ar1, Ar2, and Ar3 is independently selected from the following groups: 。 5. The organic compound according to claim 1, characterized in that, The organic compound is selected from the structure shown in formula (IV-1), formula (IV-2), or formula (IV-3): 。 6. The organic compound according to claim 1, characterized in that, The organic compound is selected from the following structures: 。 7. A mixture, characterized in that: The mixture comprises the organic compound as described in any one of claims 1-6 and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes.

8. A composition, characterized in that: The composition comprises an organic compound as described in any one of claims 1-6 or a mixture as described in claim 7, and at least one organic solvent.

9. An organic electronic device comprising at least one functional layer, characterized in that: The functional layer comprises an organic compound as described in any one of claims 1-6, or a mixture as described in claim 7, or the functional layer is prepared from the composition as described in claim 8.

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