An organic compound and its application in organic electronic devices

Abstract

The present invention relates to an organic compound, which is selected from a seven-membered nitrogen heterocyclic core. The seven-membered nitrogen heterocycle has good electron-donating ability; it is connected to a terminal electron-withdrawing group A, enabling it to have good charge mobility, appropriate energy levels and good chemical stability, and is used as a small molecule acceptor material in organic solar cells to improve the photoelectric conversion efficiency of the device.

Description

Technical Field

[0001] The present invention relates to the field of organic solar cell materials, in particular to an organic compound and its application in organic electronic devices. Background Art

[0002] Organic Solar Cells (OPV) have attracted wide global attention due to their advantages such as low cost, light weight, simple preparation process, and large-area flexible preparation. An organic solar cell generally consists of five parts: an anode, an anode buffer layer, an active layer, a cathode buffer layer, and a cathode, where the active layer generally contains a donor material and an acceptor material. The working principle of an organic solar cell is as follows: When sunlight passes through the transparent substrate and the electrode and enters the active layer, the donor-acceptor material absorbs photons with energy greater than its bandgap energy. Electrons are excited from the highest occupied molecular orbital (HOMO) and jump to the lowest unoccupied molecular orbital (LUMO), and at the same time, corresponding holes are generated at the HOMO. Due to the relatively small relative dielectric constant of organic materials, the electrons and holes at this time exist in the form of bound excitons. Then, the excitons diffuse to the donor-acceptor interface, and under the drive of the energy level difference, the excitons dissociate to achieve charge separation. Subsequently, under the action of the built-in electric field, the free holes and electrons respectively transport along the continuous channels of the donor and acceptor materials to reach the anode and cathode, and are collected by the electrodes and output to the external circuit to form a current. Therefore, the selection of the active layer material is crucial for the efficiency of organic solar cell devices.

[0003] In the early and middle stages of the development of organic solar cells, fullerenes and their derivatives represented by PC61BM and PC71BM dominated the electron acceptor materials due to their high electron affinity, isotropic electron transport ability, and high electron mobility. This stage is usually referred to as the fullerene era. However, the limitations of the molecular structure of fullerene acceptors result in weak absorption in the visible light region and poor energy level tunability, which limit the efficiency improvement of organic solar cells. In recent years, the emergence of non-fullerene acceptor materials has overcome the deficiencies of fullerene acceptors to a certain extent, greatly improving the photoelectric conversion efficiency of devices and promoting the development of the field of organic solar cells. Most of the existing non-fullerene acceptor materials adopt large fused-ring cores, such as structures like ITIC and Y6. Although they exhibit excellent device performance, their structure synthesis is complex, the synthesis route is too long, the reaction yield is low, and the synthesis cost is high, which severely restricts the industrial development of organic solar cells.

[0004] Therefore, it is necessary to develop new non-fullerene acceptor materials for organic solar cells with high efficiency and easy synthesis to promote the industrial development of organic solar cells. Summary of the Invention

[0005] The object of the present invention is to provide a non-fused-ring acceptor organic compound, which is simple to synthesize and can be used as a small molecule acceptor material in organic solar cells, thereby improving the photoelectric conversion efficiency of the device.

[0006] To achieve the object of the present invention, the technical solution is as follows:

[0007] An organic compound, characterized in that it has a structure shown in the general formula (I):

[0008]

[0009] Wherein,

[0010] Ar 1 and Ar 2 are independently selected from the structural formula (A-1), structural formula (A-2), structural formula (A-3), structural formula (A-4), or a combination thereof:

[0011]

[0012] Wherein, W is selected from O, S, CR 11 R 12 or NR 13 ;

[0013] R 0 -R 13 Each occurrence is independently selected from: -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 alkylthio group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a branched or cyclic alkoxy group having 3 to 20 C atoms, a branched or cyclic alkylthio 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, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a group formed by combining the above groups;

[0014] * represents the connection site;

[0015] EG 1 and EG 2 are independently selected from electron-withdrawing groups.

[0016] Correspondingly, the present invention also provides a mixture, comprising the above-mentioned organic compound and at least one organic functional material, and the organic functional material is selected from an anode buffer layer material, a cathode buffer layer material, an active layer donor material, or an active layer acceptor material.

[0017] Correspondingly, the present invention also provides an electron acceptor material, and the electron acceptor material is selected from the above-mentioned organic compound or the above-mentioned mixture.

[0018] Correspondingly, the present invention also provides an organic electronic device, comprising at least one functional layer, and the functional layer material is selected from the above-mentioned organic compound or mixture.

[0019] Compared with the prior art, the present invention has the following remarkable advantages: providing a heptacyclic nitrogen heterocyclic organic compound, the heptacyclic nitrogen heterocyclic having good electron-donating ability; connecting with the terminal electron-withdrawing group A, so that it has good charge mobility, appropriate energy levels and good chemical stability, and being used as a small molecule acceptor material in an organic solar cell to improve the photoelectric conversion efficiency of the device. At the same time, the compound protected by the present invention has easily available raw materials, a simple synthesis route, low preparation cost, can be prepared in batches, and has good industrial application prospects. Detailed Embodiments

[0020] To make the objectives, technical solutions and effects of the present application clearer and more definite, the present application is further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present application and are not used to limit the present application.

[0021] As used herein, the term "and / or", "or / and", "and / or" includes any one of two or more related listed items, and also includes any and all combinations of the related listed items. The any and all combinations include any two related listed items, any more related listed items, or the combination of all related listed items. It should be noted that when at least two conjunctions selected from "and / or", "or / and", "and / or" are used to connect at least three items, it should be understood that in the present application, this technical solution undoubtedly includes the technical solution connected by "logical AND", and also undoubtedly includes the technical solution connected by "logical OR". For example, "A and / or B" includes three parallel solutions: A, B, and A + B. Another example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, D (that is, the technical solution connected by "logical OR"), and also includes any and all combinations of A, B, C, D, that is, it includes the combination of any two or any three of A, B, C, D, and also includes the four-item combination of A, B, C, D (that is, the technical solution connected by "logical AND").

[0022] In the present invention, organic photovoltaic device, organic solar cell, and OPV have the same meaning and can be used interchangeably.

[0023] In the present invention, aromatic group, aromatic, and aromatic ring system have the same meaning and can be used interchangeably.

[0024] In the present invention, heteroaromatic group, heteroaromatic, and heteroaromatic ring system have the same meaning and can be used interchangeably.

[0025] In the present invention, "heteroatom" is a non-carbon atom, which can be an N atom, an O atom, an S atom, etc.

[0026] In the present invention, "substituted" means that one or more hydrogen atoms in the substituent are replaced by a substituent.

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

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

[0029] In the present invention, "the number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself in a structural compound obtained by bonding atoms into a ring (for example, a monocyclic compound, a fused-ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below under the condition of no special explanation. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0030] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, a fused-ring aryl group, or a polycyclic aryl group. For a polycyclic ring species, 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 containing 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, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, dinaphthylphenyl, acenaphthylenyl and their derivatives. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (for example, <10% of non-H atoms, such as C, N or O atoms), specifically such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0031] "Heteroaryl or heteroaromatic group" means that at least one carbon atom in the aryl group is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted. Suitable examples include but are not limited to: thienyl, furyl, pyrrolyl, dioxazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, perimidinyl, quinazolinone, dibenzothienyl, dibenzofuryl, carbazolyl and its derivatives.

[0032] In the present invention, "alkyl" may represent straight-chain, branched-chain, and / or cyclic alkyl. The number of carbon atoms in the alkyl may be 1 to 50, 1 to 30, 1 to 20, 1 to 15, or 1 to 6. Phrases containing this term, for example, "C1-9 alkyl" refer to an alkyl containing 1 to 9 carbon atoms, and each occurrence may independently be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

[0033] "Amino group" refers to a derivative of an amine and has a 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 heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic group)2, -NH(heterocyclic group), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic group), -N(cycloalkyl)(heterocyclic group), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0034] In the present invention, unless otherwise defined, hydroxy refers to -OH, carboxy refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, halocarbonyl refers to -C(=O)z (where z represents a halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0035] The term "alkoxy" refers to a group having the structure "-O-alkyl", i.e., the alkyl group as defined above is connected to another group via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-O-C(CH3)3 or -OtBu). The term "alkylthio" refers to a group having the structure "-S-alkyl", i.e., the alkyl group as defined above is connected to another group via a sulfur atom.

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

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

[0038] In the present invention, when a group contains multiple substituents with the same symbol, the substituents can be the same or different from each other. For example The six Rs on the benzene ring can be the same or different from each other.

[0039] In the present invention, the expression "independently selected from" for one or more groups means that when one or more groups appear simultaneously and at multiple positions in a compound, they are all independently selected and can be the same or different.

[0040] In the present invention, the single bond to which a substituent is attached passes through the corresponding ring, indicating that the substituent can be connected to any optional position of the ring. For example In, R is connected to any substitutable site of the benzene ring.

[0041] In the present invention, "its combination", "any combination thereof", "any combination mode thereof", "combination", etc. include all suitable combination modes of any two, any three, or any three or more items in the listed groups.

[0042] In the present invention, terms such as "further", "even further", "especially", etc. are used for descriptive purposes and represent differences in content, but should not be construed as limiting the scope of protection of the present invention.

[0043] In the present invention, "optionally", "optional", and "option" mean that something is either present or absent, that is, either one of two alternative options of "present" or "absent" is selected. If the term "optional" appears multiple times in a technical solution, without special instructions, contradictions, or mutual constraints, each "optional" is independent of the others.

[0044] In the present invention, among the technical features described in an open-ended manner, it includes a closed technical solution composed of the listed features, as well as an open technical solution containing the listed features.

[0045] In the present invention, an electron-donating group is a group or atom with a stronger electron-donating ability than hydrogen, that is, it has an electron-donating inductive effect; while an electron-withdrawing group is a group or atom with a stronger electron-withdrawing ability than hydrogen, that is, it has an electron-withdrawing inductive effect. The inductive effect is the effect caused by the difference in polarity (electronegativity) of atoms or groups in a molecule, resulting in the movement of the bonding electron cloud in a certain direction along the atomic bond. The electron cloud moves towards the group or atom with a stronger electronegativity.

[0046] To achieve the object of the present invention, the specific technical solutions for solving the problem are as follows:

[0047] An organic compound having a structure represented by the general formula (I):

[0048]

[0049] Wherein,

[0050] Ar 1 、Ar 2 independently selected from structural formula (A-1), structural formula (A-2), structural formula (A-3), structural formula (A-4), or a combination thereof:

[0051]

[0052] Wherein,

[0053] W is selected from O, S, CR 11 R 12 or NR 13 ;

[0054] R 0 -R 13Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain alkylthio group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic alkylthio group having 3 to 20 carbon atoms, a silyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a group formed by combining the above groups;

[0055] * represents the connection site;

[0056] EG 1 and EG 2 are independently selected from electron-withdrawing groups.

[0057] EG 1 and EG 2 have a strong electron-withdrawing effect, and being located at both ends of the organic compound can enable the organic compound to have strong visible light absorption ability, high charge transport performance, and appropriate electron energy levels.

[0058] In one embodiment, the organic compound is selected from the general formula (II-1), general formula (II-2), general formula (II-3), or general formula (II-4):

[0059]

[0060]

[0061] In one embodiment, are independently selected from any one of the following groups:

[0062]

[0063] wherein:

[0064] Each occurrence of M is independently selected from O, S, or C(CN) 2 ;

[0065] Each occurrence of X is independently selected from CR 14 or N;

[0066] Each occurrence of Y is independently selected from O, S, or Se;

[0067] R14 , R 15 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 8 C atoms, a branched-chain alkyl group having 3 to 8 C atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, or a group formed by a combination of the above groups; any two adjacent Rs 14 Either form a ring or do not form a ring with each other;

[0068] * represents a connection site.

[0069] In one embodiment, the "any two adjacent Rs 14 forming a ring with each other" preferably forms a five-membered heteroaromatic ring which is substituted or unsubstituted by R * , or a six-membered aromatic group or heteroaromatic group which is substituted or unsubstituted by R * ; each occurrence of the R * is independently selected from: -D, a straight-chain alkyl group having 1 to 8 C atoms, a branched-chain alkyl group having 3 to 8 C atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, or a group formed by a combination of the above groups. In one embodiment, the "any two adjacent Rs 14 forming a ring with each other" preferably forms a six-membered benzene ring which is substituted or unsubstituted by R * , or a five-membered thiophene ring which is substituted or unsubstituted by R * .

[0070] In one embodiment, each occurrence of Y is independently selected from S.

[0071] In one embodiment, is independently selected from the following groups:

[0072]

[0073] Wherein: R 14 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 6 C atoms, a branched-chain alkyl group having 3 to 6 C atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, or a group formed by a combination of the above groups;

[0074] R 15 Each occurrence is independently selected from a straight-chain alkyl group having 1 to 6 C atoms, a branched-chain alkyl group having 3 to 6 C atoms.

[0075] Furthermore, each occurrence of R 14 is independently selected from -H, -D, methyl, ethyl, propyl, isopropyl, tert-butyl, -Cl, -Br, -F, -I, -CN, -NO 2 , or -CF 3 .

[0076] In one embodiment, Independently selected from the following groups:

[0077]

[0078]

[0079]

[0080] In one embodiment, Selected from the same group. In another embodiment, Selected from different groups.

[0081] In one embodiment, R 0 Is selected from: -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 alkylthio group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a branched or cyclic alkoxy group having 3 to 20 C atoms, a branched or cyclic alkylthio group having 3 to 20 C atoms, an aromatic group having 6 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms, or a group formed by combining the above groups; one or more H atoms in the above groups are unsubstituted or substituted by deuterium.

[0082] In one embodiment, R 0 Is selected from a straight-chain alkyl group having 1 to 15 C atoms, or a branched or cyclic alkyl group having 3 to 15 C atoms; one or more H atoms in the above groups are unsubstituted or substituted by deuterium.

[0083] In one embodiment, R 0 Is selected from methyl, ethyl, straight-chain or branched C 3 H 7 、straight-chain or branched C 4 H 9 、straight-chain or branched C 5 H 11 、straight-chain or branched C 6 H 13 、straight-chain or branched C 7 H 15 、straight-chain or branched C 8 H 17 、straight-chain or branched C 9 H 19 、straight-chain or branched C 10 H 21 、straight-chain or branched C 11 H 23 、straight-chain or branched C 12 H 25 、straight-chain or branched C 13 H27 - a straight-chain or branched-chain C 14 H 29 - a straight-chain or branched-chain C 15 H 31 ; one or more H atoms in the above groups are unsubstituted or substituted with deuterium.

[0084] In one embodiment, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 are independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain alkylthio group having 1 to 20 carbon atoms, a branched-chain or cyclic alkyl group having 3 to 20 carbon atoms, a branched-chain or cyclic alkoxy group having 3 to 20 carbon atoms, a branched-chain or cyclic alkylthio group having 3 to 20 carbon atoms, an aromatic group having 6 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms, or a group formed by combining the above groups.

[0085] In one embodiment, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 are independently selected from: -H, -D, a straight-chain alkyl group having 1 to 15 carbon atoms, a straight-chain alkoxy group having 1 to 15 carbon atoms, a straight-chain alkylthio group having 1 to 15 carbon atoms, a branched-chain or cyclic alkyl group having 3 to 15 carbon atoms, a branched-chain or cyclic alkoxy group having 3 to 15 carbon atoms, a branched-chain or cyclic alkylthio group having 3 to 15 carbon atoms, an aromatic group having 6 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms, or a group formed by combining the above groups.

[0086] In one embodiment, R 1 -R 2Independently selected from -H, -D, a straight-chain alkyl group having 1 to 15 C atoms, a branched-chain alkyl group having 3 to 15 C atoms, or a group formed by combining the above groups.

[0087] In one embodiment, R 1 -R 2 Independently selected from -H, -D, methyl, ethyl, straight-chain or branched-chain C 3 H 7 、straight-chain or branched-chain C 4 H 9 、straight-chain or branched-chain C 5 H 11 、straight-chain or branched-chain C 6 H 13 、straight-chain or branched-chain C 7 H 15 、straight-chain or branched-chain C 8 H 17 、straight-chain or branched-chain C 9 H 19 、straight-chain or branched-chain C 10 H 21 、straight-chain or branched-chain C 11 H 23 、straight-chain or branched-chain C 12 H 25 、straight-chain or branched-chain C 13 H 27 、straight-chain or branched-chain C 14 H 29 、straight-chain or branched-chain C 15 H 31 ; one or more H atoms in the above groups are unsubstituted or substituted by deuterium.

[0088] In one embodiment, R 3 -R 4 Independently selected from -H, -D, a straight-chain alkyl group having 1 to 15 C atoms, a branched-chain alkyl group having 3 to 15 C atoms, or a group formed by combining the above groups.

[0089] In one embodiment, R 3 -R 4 Independently selected from -H, -D, methyl, ethyl, straight-chain or branched-chain C 3 H 7 、straight-chain or branched-chain C 4 H 9 、straight-chain or branched-chain C 5 H 11 、straight-chain or branched-chain C 6 H 13 、straight-chain or branched-chain C 7 H 15 、straight-chain or branched-chain C 8 H 17, linear or branched C 9 H 19 , linear or branched C 10 H 21 , linear or branched C 11 H 23 , linear or branched C 12 H 25 , linear or branched C 13 H 27 , linear or branched C 14 H 29 , linear or branched C 15 H 31 ; one or more H atoms in the above groups are unsubstituted or substituted by deuterium.

[0090] In one embodiment, R 5 -R 8 independently selected from -H, -D, linear alkyl having 1 to 15 C atoms, branched alkyl having 3 to 15 C atoms, aromatic group having 6 to 10 ring atoms, or a group formed by combining the above groups.

[0091] In one embodiment, R 5 -R 6 is selected from -H.

[0092] In one embodiment, R 7 -R 8 is selected from -H, -D, linear alkyl having 1 to 10 C atoms, branched alkyl having 3 to 10 C atoms, aromatic group having 6 to 10 ring atoms, or a group formed by combining the above groups.

[0093] In one embodiment, R 7 -R 8 is selected from linear alkyl having 1 to 10 C atoms, branched alkyl having 3 to 10 C atoms, phenyl substituted or unsubstituted by R # , and the R # is selected from linear alkyl having 1 to 10 C atoms, branched alkyl having 3 to 10 C atoms.

[0094] In one embodiment, R 9 -R 10 independently selected from -H, -D, linear alkyl having 1 to 10 C atoms, branched alkyl having 3 to 10 C atoms.

[0095] In one embodiment, R 9 -R 10 is independently selected from -H.

[0096] In one embodiment, R 11 , R 12 , R13 Independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, or a group formed by combining the above groups. Further, R 13 is selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms. R 11- R 12 is selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, or a group formed by combining the above groups.

[0097] In one embodiment, R 11 , R 12 , R 13 are independently selected from methyl, ethyl, straight-chain or branched-chain C 3 H 7 , straight-chain or branched-chain C 4 H 9 , straight-chain or branched-chain C 5 H 11 , straight-chain or branched-chain C 6 H 13 , straight-chain or branched-chain C 7 H 15 , straight-chain or branched-chain C 8 H 17 , straight-chain or branched-chain C 9 H 19 , straight-chain or branched-chain C 10 H 21 ; one or more H atoms in the above groups are unsubstituted or substituted by deuterium. In one embodiment, Ar 1 and Ar 2 are selected from the same group.

[0098] In one embodiment, an organic compound according to the present invention is a symmetric structure compound.

[0099] According to an organic compound of the present invention, specific examples thereof are as follows, but are not limited thereto:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111] In one embodiment, the organic compound according to the present invention can be used as an active layer material in an organic electronic device; preferably, the organic compound according to the present invention can be used as an active layer acceptor material in an organic solar device.

[0112] The present invention also provides a mixture comprising at least one of the above-mentioned organic compounds and at least one other organic functional material, and the at least one other organic functional material can be selected from an anode buffer layer material, a cathode buffer layer material, an active layer donor material, or an active layer acceptor material. The weight ratio thereof to the other organic functional material is from 1:99 to 99:1. In one embodiment, the photoactive layer comprises a donor material and an acceptor material, and the weight ratio thereof is donor material / acceptor material = 1 / 1.2.

[0113] |In one embodiment, the other organic functional material is selected from an active layer donor material or an active layer acceptor material.

[0114] In one embodiment, the mixture according to the present invention comprises at least one of the above-mentioned organic compounds and at least one other organic functional material, and the at least one other organic functional material is selected from PBDB-T, PM6, PM7, PTQ10 or a combination thereof.

[0115] This application further relates to an electron acceptor material, and the electron acceptor material is selected from the organic compounds or mixtures as described above; when the electron acceptor material is a mixture, the organic mixture is selected from at least one of the above-mentioned organic compounds and at least one other active layer acceptor material; in one embodiment, the other active layer acceptor material is selected from fullerenes and their derivatives, such as PC61BM, PC71BM and their derivatives.

[0116] This application also relates to a composition comprising at least one of the above-mentioned organic compounds or mixtures and at least one organic solvent. The organic solvent is selected from aliphatic hydrocarbons, chlorinated hydrocarbons, aromatic hydrocarbons, ketones, ethers or mixtures thereof.

[0117] Specifically, the above organic solvents can be selected from dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, 2,4-dimethylanisole, 1-methylnaphthalene, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, n-butyl acetate, N,N-dimethylformamide, dimethylacetamide, dimethyl sulfoxide, 1,5-dimethyltetrahydrofuran, acetophenone, acetophenone, tetralin, 2-methylthiophene, 3-methylthiophene, decalin, indane, methyl benzoate, ethyl benzoate, mesitylene, or a mixture of any two or more of the above organic solvents.

[0118] In a preferred embodiment, the organic solvent is selected from chlorobenzene, toluene, o-xylene, or chloroform, but is not limited thereto.

[0119] It should be noted that the above organic solvent can evaporate from the solvent system to form a thin film including the organic compound or mixture.

[0120] In some embodiments, the composition is a solution. In other embodiments, the composition is a suspension. The solution or suspension may additionally include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives can be selected from, but are not limited to, at least one of surface active compounds, lubricants, wetting agents, dispersants, water repellents, and adhesives.

[0121] This application also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices. In one embodiment, the composition is used to prepare organic electronic devices by a printing or coating preparation method. The printing or coating preparation method can be, but is not limited to, inkjet printing, gravure printing, spraying, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brush coating, pad printing, slot die coating, etc. Preferably, slot coating, spin coating, and inkjet printing.

[0122] This application further relates to the application of an organic compound or mixture or composition as described above in organic electronic devices. The organic electronic devices can be selected from, but are not limited to, organic solar cells (OPV), organic light-emitting diodes (OLED), organic light-emitting electrochemical cells (OLEEC), organic field-effect transistors (OFET), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes, etc., and is particularly preferably OPV.

[0123] The present application also relates to an organic electronic device, which includes at least one functional layer, and the functional layer contains the above-mentioned organic compound or the above-mentioned mixture or is prepared from the above-mentioned composition. Preferably, the functional layer is selected from an anode buffer layer, an active layer or a cathode buffer layer.

[0124] In one embodiment, the organic electronic device at least includes a first electrode, a second electrode and one or more functional layers located between the first electrode and the second electrode. Preferably, the one or more functional layers are selected from active layers; more preferably, the one or more functional layers are selected from an anode buffer layer, an active layer and a cathode buffer layer.

[0125] It should be noted that in order to improve the performance of the organic solar cell device, the functional layer may further include other functional layers, including but not limited to a charge injection layer and / or a charge blocking layer.

[0126] Furthermore, the organic solar cell further includes a substrate. Specifically, the substrate can be disposed under the first electrode.

[0127] In one embodiment, the first electrode is an anode and the second electrode is a cathode; in another embodiment, the first electrode can be a cathode and the second electrode can be an anode.

[0128] In one embodiment, as the substrate, a substrate having excellent transparency, surface smoothness, operability and waterproofness can be used. Specifically, a glass substrate, a thin film glass substrate or a transparent plastic substrate can be used. The plastic substrate can include a film in a single-layer or multi-layer form, such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetheretherketone (PEEK) and polyimide (PI), etc., but not limited thereto, and a substrate commonly used for organic solar cells can also be used.

[0129] At least one of the first electrode and the second electrode is transparent or semi-transparent to allow light to enter. The materials used to prepare the electrodes can be selected from metals, such as vanadium (V), chromium (Cr), zinc (Zn), silver (Ag), aluminum (Al), platinum (Pt), tungsten (W), copper (Cu), molybdenum (Mo), gold (Au), nickel (Ni) and palladium (Pd), or their alloys, etc.; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO), etc.; combinations of metals and oxides, such as ZnO∶Al or SnO2∶Sb, etc.; and conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, etc.; or materials having a multi-layer structure, such as LiF / Al, LiO 2 / Al, LiF / Fe, MoO 3 / Al, Al∶Li, Al∶BaF2 and Al∶BaF 2 ∶Ba, etc., but not limited thereto.

[0130] The active layer contains an electron donor material and an electron acceptor material. In this specification, the active layer material may refer to an electron donor material and an electron acceptor material.

[0131] Specifically, the electron acceptor material is selected from the organic compounds or mixtures described in accordance with the present invention.

[0132] Specifically, the electron donor material may be various polymer materials or small molecule materials. The polymer materials may be selected from polythiophene material systems such as P3AT, P3HT, P3OT, P3DDT, etc.; fluorene-containing polymer material systems such as PF8BT, etc.; novel structure narrow bandgap polymer material systems copolymerized from benzothiadiazoles (BT, BBT), quinoxalines (QU, PQ), pyrazines (TP, PQ) and electron-rich groups (such as thiophene derivatives), such as PCDTBT, PCPDTBT, PFO-DBT, PTB7, PM6, PM7, PBDB-T, J52, PTQ10, D18, etc. The small molecule materials may be selected from one or more of the following: copper(II) phthalocyanine, zinc phthalocyanine, tris[4-(5-dicyanomethylene methyl-2-thienyl)phenyl]amine, 2,4-bis[4-(N,N-dibenzylamino)-2,6-dihydroxyphenyl] squarylium, benz[b]anthracene and pentacene, B8, B10, etc.

[0133] The photoactive layer can be formed by the following method: dissolving a photoactive material, such as an electron donor and / or an electron acceptor, in an organic solvent, and then coating the resulting solution by methods such as spin coating, dip coating, screen printing, gravure printing, spraying, doctor blading, slot die coating, and inkjet printing, but not limited thereto.

[0134] The anode buffer layer material may be selected from PEDOT:PSS (poly(3,4-ethylenedioxythiophene)) of poly(styrenesulfonic acid), molybdenum oxide (MoOx), vanadium oxide (V 2 O 5 ), nickel oxide (NiO), tungsten oxide (WO x , preferably, x is selected from 2 or 3), etc., but not limited thereto.

[0135] The cathode buffer layer material may be an electron-withdrawing metal oxide or polymer. The metal oxide may be a metal complex containing 8-hydroxyquinoline, a complex containing Alq 3 complex, a metal complex containing Liq, LiF, Ca, titanium oxide (TiOx), zinc oxide (ZnO), cesium carbonate (Cs 2 CO 3) etc., the polymer can be PFN-Br, PFN or the like, but not limited thereto.

[0136] In one embodiment, an organic electronic device according to the present invention, the organic electronic device at least includes a first electrode, a second electrode, and one or more functional layers located between the first electrode and the second electrode, the functional layer at least includes a photoactive layer, the photoactive layer includes a donor material and an acceptor material, wherein the acceptor material is selected from the organic compounds or mixtures as described above, and the donor material is selected from PM6; further, the mass ratio of the donor material / acceptor material is: 1:1 - 1:1.2. Further, the organic electronic device is an organic solar cell.

[0137] The present invention also relates to the application of the organic solar cell according to the present invention in various devices, including, but not limited to, automobiles and building integrated photovoltaics (BIPV), electronic price tags, indoor photovoltaics, Internet of Things, smart agriculture, and the like.

[0138] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims define the scope of the present invention. Under the guidance of the inventive concept of the present invention, those skilled in the art should realize that certain changes made to the embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0139] Here, the organic compounds and organic electronic devices according to the present invention are exemplified, but the present invention is not limited to the following embodiments.

[0140] Preparation of organic compounds:

[0141] Example 1: Synthesis of Compound 1

[0142]

[0143] Synthesis of Compound 1-2:

[0144] Accurately weigh compound 1-1 (42.5 g, 100 mmol), raw material A (23.2 g, 120 mmol), bis(dibenzylideneacetone)palladium (1.7 g, 3 mmol), sodium tert-butoxide (19.2 g, 200 mmol) and add them to a 1000 mL three-necked flask in sequence, add about 600 mL of anhydrous toluene, pump and fill with nitrogen three times, slowly drop about 14 mL of toluene solution of tri-tert-butylphosphine (10% by mass ratio) into the reaction system, then slowly heat to 100 ° C and react overnight, cool to room temperature after the raw material is completely reacted, dilute with water and extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate and distill under reduced pressure to remove excess solvent, mix with silica gel column chromatography, eluent is PE:DCM=10:1 (volume ratio), and obtain about 38.5 g of compound 1-2, yield: 71.6%. Ms: 537.45.

[0145] Synthesis of compound 1-3:

[0146] Accurately weigh compound 1-2 (37.6g, 70mmol), bis(boronic acid pinacol ester) (39.1g, 154mmol), bis(triphenylphosphine palladium dichloride) (1.54g2.1mmol), potassium acetate (20.6g, 210mmol) and add them to a 1000mL three-necked flask in sequence, add about 600mL of anhydrous dioxane, pump and fill with nitrogen three times, then heat to 100℃ and react for four hours. After the raw materials react completely, cool to room temperature, dilute with water and extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate and remove excess solvent by vacuum distillation, mix with silica gel and column chromatography, eluent is PE:DCM=5:1 (volume ratio) to obtain about 34.5g of compound 1-3, yield: 78%. Ms: 632.32

[0147] Synthesis of compound 1-5:

[0148] Accurately weigh compound 1-4 (59.4g, 100mmol) and add it to a 2000mL three-necked flask, add about 600mL of anhydrous THF, pump and fill with nitrogen three times, then cool the liquid nitrogen ethanol to -80°C, then slowly drop n-butyl lithium (2.5M40mL) into the three-necked flask, keep the low temperature for 1 hour, then slowly drop anhydrous DMF (15.5mL) into the reaction system, naturally warm to room temperature and react for 4 hours. After the raw material is completely reacted, dilute with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove the excess solvent by vacuum distillation, mix with silica gel column chromatography, and eluent is PE:EA=8:1 (volume ratio) to obtain about 42.6g of compound 1-5, yield: 78.5%. Ms:542.08

[0149] Synthesis of compound 1-6:

[0150] Accurately weigh Compound 1-5 (42.6 g, 78.5 mmol) and add it to a 1000 mL three-necked flask. Add approximately 500 mL of tetrahydrofuran. After evacuating and purging with nitrogen three times, cool the temperature to around 0 °C. Slowly add NBS (14 g dissolved in 150 mL of THF) dropwise to the reaction system. After the addition is complete, let the temperature rise to room temperature naturally and react overnight. After the raw materials have completely reacted, wash with water, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and then distill under reduced pressure to remove the excess solvent to obtain approximately 43 g of the crude product. Yield: 88%. Ms: 622.96

[0151] Synthesis of Compound 1-7:

[0152] Accurately weigh Compound 1-3 (18.9 g, 30 mmol), Compound 1-6 (37.3 g, 60 mmol), palladium tetrakis(triphenylphosphine) (1.2 g, 1 mmol), and potassium carbonate (12.4 g, 90 mmol), and add them to a 1000 mL three-necked flask in sequence. Add 500 mL of toluene and 100 mL of water. After evacuating and purging with nitrogen three times, heat to 80 °C and react overnight. After the raw materials have completely reacted, dilute with water, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and then distill under reduced pressure to remove the excess solvent. Perform silica gel sample-mixed column chromatography, and the eluent is PE:DCM = 4:1 (volume ratio) to obtain approximately 36.3 g of Compound 1-7. Yield: 82.8%. Ms: 1462.05.

[0153] Synthesis of Compound 1:

[0154] Accurately weigh Compound 1-7 (7.3 g, 5 mmol), Compound 1-8 (1.94 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them to a 250 mL three-necked flask in sequence. Add approximately 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill under reduced pressure to remove the excess solvent. Perform silica gel sample-mixed column chromatography, and the eluent is PE:DCM = 3:1 (volume ratio) to obtain approximately 4.2 g of Compound 1. Yield: 46.3%.

[0155] Ms: 1813.54

[0156] Example 2: Synthesis of Compound 3

[0157]

[0158] Synthesis of Compound 3:

[0159] Accurately weigh Compound 1-7 (7.3 g, 5 mmol), Compound 2-1 (2.3 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively into a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat the mixture to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the stationary phase and the eluent being PE:DCM = 3:1 (volume ratio) gives about 4.4 g of Compound 3, with a yield of 46.7%. Ms: 1885.56

[0160] Example 3: Synthesis of Compound 11

[0161]

[0162] Synthesis of Compound 11:

[0163] Accurately weigh Compound 1-7 (7.3 g, 5 mmol), Compound 3-1 (2.48 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively into a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat the mixture to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the stationary phase and the eluent being PE:DCM = 3:1 (volume ratio) gives about 4.2 g of Compound 11, with a yield of 43.7%. Ms: 1913.88

[0164] Example 4: Synthesis of Compound 14

[0165]

[0166] Synthesis of Compound 14:

[0167] Accurately weigh Compound 1-7 (7.3 g, 5 mmol), Compound 4-1 (2.8 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively into a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat the mixture to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the stationary phase and the eluent being PE:DCM = 3:1 (volume ratio) gives about 4.3 g of Compound 14, with a yield of 43.3%. Ms: 1986.04

[0168] Example 5: Synthesis of Compound 17

[0169]

[0170] Synthesis of Compound 17:

[0171] Accurately weigh Compound 1-7 (7.3 g, 5 mmol), Compound 5-1 (1.6 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively to a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the carrier, and the eluent is PE:DCM = 3:1 (volume ratio) to obtain about 3.3 g of Compound 17, yield: 37.8%. Ms: 1747.65.

[0172] Example 6: Synthesis of Compound 18

[0173]

[0174] Synthesis of Compound 18:

[0175] Accurately weigh Compound 1-7 (7.3 g, 5 mmol), Compound 6-1 (1.93 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively to a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the carrier, and the eluent is PE:DCM = 3:1 (volume ratio) to obtain about 3.4 g of Compound 18, yield: 46.9%. Ms: 1811.31.

[0176] Example 7: Synthesis of Compound 22

[0177]

[0178] Synthesis of Compound 22:

[0179] Accurately weigh Compound 1-7 (7.3 g, 5 mmol), Compound 7-1 (2.79 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively to a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the carrier, and the eluent is PE:DCM = 3:1 (volume ratio) to obtain about 4.4 g of Compound 22, yield: 44.4%. Ms: 1983.53

[0180] Example 8: Synthesis of Compound 30

[0181]

[0182] Synthesis of Compound 30:

[0183] Accurately weigh Compound 1-7 (7.3 g, 5 mmol), Compound 8-1 (1.82 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively to a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat the mixture to 60 °C and react overnight. After the raw materials are completely reacted, distill off the excess solvent under reduced pressure. Mix the sample with silica gel and perform column chromatography. The eluent is PE:DCM = 3:1 (volume ratio) to obtain about 4.1 g of Compound 30, with a yield of 45.8%. Ms: 1789.38.

[0184] Example 9: Synthesis of Compound 46

[0185]

[0186] Synthesis of Compound 9-1:

[0187] Accurately weigh Compound 1-3 (18.9 g, 30 mmol), 5-bromothiophene-2-carbaldehyde (11.5 g, 60 mmol), tetrakis(triphenylphosphine)palladium (1.2 g, 1 mmol), and potassium carbonate (12.4 g, 90 mmol), and add them successively to a 1000 mL three-necked flask. Add 500 mL of dioxane and 100 mL of water. After evacuating and purging with nitrogen three times, heat the mixture to 80 °C and react overnight. After the raw materials are completely reacted, dilute with water, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and distill off the excess solvent under reduced pressure. Mix the sample with silica gel and perform column chromatography. The eluent is PE:DCM = 4:1 (volume ratio) to obtain about 15.6 g of Compound 9-1, with a yield of 86.6%. Ms: 599.10.

[0188] Synthesis of Compound 46:

[0189] Accurately weigh Compound 9-1 (3 g, 5 mmol), Compound 2-1 (2.3 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively to a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat the mixture to 60 °C and react overnight. After the raw materials are completely reacted, distill off the excess solvent under reduced pressure. Mix the sample with silica gel and perform column chromatography. The eluent is PE:DCM = 3:1 (volume ratio) to obtain about 2.3 g of Compound 46, with a yield of 44.9%. Ms: 1024.33

[0190] Example 10: Synthesis of Compound 52

[0191]

[0192] Synthesis of Compound 52:

[0193] Accurately weigh 3 g (5 mmol) of Compound 9-1, 2.73 g (10 mmol) of Compound 10-1, and 1.6 g (20 mmol) of pyridine, and sequentially add them into a 250 mL three-necked flask. Add approximately 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the carrier, and the eluent is PE:DCM = 3:1 (volume ratio) to obtain approximately 2.3 g of Compound 52, with a yield of 41.4%. Ms: 1110.69.

[0194] Example 11: Synthesis of Compound 56

[0195]

[0196] Synthesis of Compound 56:

[0197] Accurately weigh 3 g (5 mmol) of Compound 9-1, 1.95 g (10 mmol) of Compound 11-1, and 1.6 g (20 mmol) of pyridine, and sequentially add them into a 250 mL three-necked flask. Add approximately 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the carrier, and the eluent is PE:DCM = 3:1 (volume ratio) to obtain approximately 2.1 g of Compound 56, with a yield of 44.1%. Ms: 955.41

[0198] Example 12: Synthesis of Compound 66

[0199]

[0200] Synthesis of Compound 66:

[0201] Accurately weigh 3 g (5 mmol) of Compound 9-1, 3.14 g (10 mmol) of Compound 12-1, and 1.6 g (20 mmol) of pyridine, and sequentially add them into a 250 mL three-necked flask. Add approximately 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the carrier, and the eluent is PE:DCM = 3:1 (volume ratio) to obtain approximately 2.2 g of Compound 66, with a yield of 45.3%. Ms: 964.68

[0202] Example 13: Synthesis of Compound 75

[0203]

[0204] Synthesis of Compound 75:

[0205] Accurately weigh 3 g (5 mmol) of Compound 9-1, 2.56 g (10 mmol) of Compound 13-1, and 1.6 g (20 mmol) of pyridine, and add them successively into a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat the mixture to 60 °C and react overnight. After the raw materials are completely reacted, distill off the excess solvent under reduced pressure. Mix the sample with silica gel and perform column chromatography. The eluent is PE:DCM = 3:1 (volume ratio) to obtain about 2.7 g of Compound 75, with a yield of 50.2%. Ms: 1076.63.

[0206] Example 14: Synthesis of Compound 79

[0207]

[0208] Synthesis of Compound 14-2:

[0209] Accurately weigh 18.9 g (30 mmol) of Compound 1-3, 14.8 g (60 mmol) of 14-1, 1.2 g (1 mmol) of tetrakis(triphenylphosphine)palladium, and 12.4 g (90 mmol) of potassium carbonate, and add them successively into a 1000 mL three-necked flask. Add 500 mL of dioxane and 100 mL of water. After evacuating and filling with nitrogen three times, heat the mixture to 80 °C and react overnight. After the raw materials are completely reacted, dilute with water, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and distill off the excess solvent under reduced pressure. Mix the sample with silica gel and perform column chromatography. The eluent is PE:DCM = 4:1 (volume ratio) to obtain about 15.6 g of Compound 14-2, with a yield of 73%. Ms: 711.74.

[0210] Synthesis of Compound 79:

[0211] Accurately weigh 3.6 g (5 mmol) of Compound 14-2, 1.94 g (10 mmol) of Compound 1-8, and 1.6 g (20 mmol) of pyridine, and add them successively into a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat the mixture to 60 °C and react overnight. After the raw materials are completely reacted, distill off the excess solvent under reduced pressure. Mix the sample with silica gel and perform column chromatography. The eluent is PE:DCM = 3:1 (volume ratio) to obtain about 2.3 g of Compound 79, with a yield of 43.2%. Ms: 1064.78

[0212] Example 15: Synthesis of Compound 90

[0213]

[0214] Synthesis of Compound 90:

[0215] Accurately weigh compound 14-2 (3.6 g, 5 mmol), compound 11-1 (1.95 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively into a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the carrier, and the eluent is PE:DCM = 3:1 (volume ratio) to obtain about 2.4 g of compound 90, yield: 45.2%. Ms: 1066.53

[0216] Example 16: Synthesis of Compound 102

[0217]

[0218] Synthesis of Compound 102

[0219] Accurately weigh compound 14-2 (3.6 g, 5 mmol), compound 7-1 (3.58 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively into a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the carrier, and the eluent is PE:DCM = 3:1 (volume ratio) to obtain about 2.6 g of compound 102, yield: 41.7%. Ms: 1234.69

[0220] Example 17: Synthesis of Compound 114

[0221]

[0222] Synthesis of Compound 114

[0223] Accurately weigh compound 14-2 (3.6 g, 5 mmol), compound 8-1 (1.82 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively into a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the carrier, and the eluent is PE:DCM = 3:1 (volume ratio) to obtain about 2.4 g of compound 114, yield: 46.2%. Ms: 1040.52

[0224] Example 18: Synthesis of Compound 49

[0225]

[0226] Synthesis of Compound 18-2

[0227] The synthesis procedure of Compound 18-2 refers to the synthesis of Compound 1-2, with the difference that raw material A is replaced by Compound 18-1 to obtain Compound 18-2, yield: 72.5%, MS: 593.74.

[0228] Synthesis of Compound 18-3:

[0229] The synthesis procedure of Compound 18-3 refers to the synthesis of Compound 1-3, with the difference that Compound 1-2 is replaced by Compound 18-2 to obtain Compound 18-3, yield: 81.3%, MS: 687.92.

[0230] Synthesis of Compound 18-5:

[0231] Accurately weigh Compound 18-3 (20.6 g, 30 mmol), 18-4 (16.5 g, 60 mmol), palladium tetrakis(triphenylphosphine) (1.2 g, 1 mmol), and potassium carbonate (12.4 g, 90 mmol), and add them successively into a 1000 mL three-necked flask. Then add 500 mL of dioxane and 100 mL of water. After evacuating and filling with nitrogen three times, heat the mixture to 80 °C and react overnight. After the raw materials have completely reacted, dilute with water, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and then distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the stationary phase and the eluent being PE:DCM = 4:1 (volume ratio) gives approximately 15.6 g of Compound 18-5, yield: 63%. Ms: 824.42.

[0232] Synthesis of Compound 49:

[0233] Accurately weigh Compound 18-5 (4.1 g, 5 mmol), Compound 18-6 (2.63 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively into a 250 mL three-necked flask. Then add approximately 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat the mixture to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the stationary phase and the eluent being PE:DCM = 3:1 (volume ratio) gives approximately 2.3 g of Compound 49, yield: 35%. Ms: 1314.66.

[0234] Example 19: Synthesis of Compound 83

[0235]

[0236] Synthesis of Compound 19-2:

[0237] Accurately weigh Compound 1-3 (18.9 g, 30 mmol), 19-1 (21.6 g, 60 mmol), tetrakis(triphenylphosphine)palladium (1.2 g, 1 mmol), and potassium carbonate (12.4 g, 90 mmol), and add them successively to a 1000 mL three-necked flask. Add 500 mL of dioxane and 100 mL of water. After evacuating and purging with nitrogen three times, heat the mixture to 80 °C and react overnight. After the raw materials are completely reacted, dilute with water, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and then distill off the excess solvent under reduced pressure. Chromatograph on a silica gel column with a eluent of PE:DCM = 4:1 (volume ratio) to obtain approximately 16.6 g of Compound 19-2, yield: 59.1%. Ms: 936.15.

[0238] Synthesis of Compound 83:

[0239] Accurately weigh Compound 19-2 (4.68 g, 5 mmol), Compound 2-1 (2.3 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and add them successively to a 250 mL three-necked flask. Add approximately 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat the mixture to 60 °C and react overnight. After the raw materials are completely reacted, distill off the excess solvent under reduced pressure. Chromatograph on a silica gel column with a eluent of PE:DCM = 3:1 (volume ratio) to obtain approximately 3.1 g of Compound 83, yield: 45%. Ms: 1360.81.

[0240] Example 20: Synthesis of Compound 4:

[0241]

[0242] Synthesis of Compound 20-2:

[0243] Accurately weigh Compound 1-3 (18.9 g, 30 mmol), 20-1 (31.5 g, 60 mmol), tetrakis(triphenylphosphine)palladium (1.2 g, 1 mmol), and potassium carbonate (12.4 g, 90 mmol), and add them successively to a 1000 mL three-necked flask. Add 500 mL of dioxane and 100 mL of water. After evacuating and purging with nitrogen three times, heat the mixture to 80 °C and react overnight. After the raw materials are completely reacted, dilute with water, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and then distill off the excess solvent under reduced pressure. Chromatograph on a silica gel column with a eluent of PE:DCM = 4:1 (volume ratio) to obtain approximately 20.67 g of Compound 20-2, yield: 54.3%. Ms: 1369.40.

[0244] Synthesis of Compound 4:

[0245] Accurately weigh 20-2 (6.34 g, 5 mmol), 18-6 (2.63 g, 10 mmol), and pyridine (1.6 g, 20 mmol) and add them successively into a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Mix the sample with silica gel and perform column chromatography. The eluent is PE:DCM = 3:1 (volume ratio) to obtain about 3.3 g of compound 4, with a yield of 37.5%. Ms: 1759.68

[0246] Example 21: Synthesis of compound 123:

[0247]

[0248] Synthesis of compound 21-2:

[0249] Accurately weigh 1-3 (18.9 g, 30 mmol), 21-1 (30.6 g, 60 mmol), tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1 mmol), and potassium carbonate (12.4 g, 90 mmol) and add them successively into a 1000 mL three-necked flask. Add 500 mL of dioxane and 100 mL of water. After evacuating and filling with nitrogen three times, heat to 80 °C and react overnight. After the raw materials have completely reacted, dilute with water, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and distill off the excess solvent under reduced pressure. Mix the sample with silica gel and perform column chromatography. The eluent is PE:DCM = 4:1 (volume ratio) to obtain about 20.67 g of compound 21-2, with a yield of 55.7%. Ms: 1236.40.

[0250] Synthesis of compound 123:

[0251] Accurately weigh 21-2 (6.2 g, 5 mmol), 2-1 (2.3 g, 10 mmol), and pyridine (1.6 g, 20 mmol) and add them successively into a 250 mL three-necked flask. Add about 120 mL of chloroform. After evacuating and filling with nitrogen three times, heat to 60 °C and react overnight. After the raw materials have completely reacted, distill off the excess solvent under reduced pressure. Mix the sample with silica gel and perform column chromatography. The eluent is PE:DCM = 3:1 (volume ratio) to obtain about 3.17 g of compound 123, with a yield of 38.2%. Ms: 1661.62

[0252] Example 22: Synthesis of compound 127:

[0253]

[0254] Synthesis of compound 22-1:

[0255] Accurately weigh Compound 18-3 (20.6 g, 30 mmol), Compound 21-1 (30.6 g, 60 mmol), palladium tetrakis(triphenylphosphine) (1.2 g, 1 mmol), and potassium carbonate (12.4 g, 90 mmol), and sequentially add them to a 1000 mL three-necked flask. Then add 500 mL of dioxane and 100 mL of water. After evacuating and purging with nitrogen three times, heat the mixture to 80 °C and react overnight. After the raw materials are completely reacted, dilute with water, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and then distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the stationary phase and the eluent being PE:DCM = 4:1 (volume ratio) gives approximately 22.6 g of Compound 22-1, with a yield of 58.4%. Ms: 1293.27.

[0256] Synthesis of Compound 127:

[0257] Accurately weigh Compound 22-1 (6.46 g, 5 mmol), Compound 22-2 (2 g, 10 mmol), and pyridine (1.6 g, 20 mmol), and sequentially add them to a 250 mL three-necked flask. Then add approximately 120 mL of chloroform. After evacuating and purging with nitrogen three times, heat the mixture to 60 °C and react overnight. After the raw materials are completely reacted, distill off the excess solvent under reduced pressure. Column chromatography with silica gel as the stationary phase and the eluent being PE:DCM = 3:1 (volume ratio) gives approximately 3.5 g of Compound 127, with a yield of 42.2%. Ms: 1657.84

[0258] Device Fabrication:

[0259] The preparation process of the OPV device including the above compounds will be described in detail through specific examples below. The structure of the OPV device is as follows: indium tin oxide ITO / PEDOT:PSS / active layer / PFN-Br / Ag

[0260] The preparation steps of Device Example 1 are as follows:

[0261] 1) Cleaning of ITO Substrate:

[0262] Clean the ITO conductive glass with detergent, rinse it thoroughly, and then ultrasonically clean it with deionized water, acetone, and isopropyl alcohol for 15 minutes. Then dry it with nitrogen and treat it in a plasma cleaner for 5 minutes to further clean the surface and improve wettability.

[0263] 2) Preparation of Anode Buffer Layer

[0264] Spin-coat PEDOT:PSS uniformly on ITO in air at a rotation speed of 3000 - 4000 rpm and dry it at 150 °C for 15 min to obtain an anode modification layer with a thickness of 20 nm.

[0265] 3) Preparation of Photoactive Layer

[0266] In a glove box (inert gas atmosphere), the photoactive layer material was spin-coated uniformly on the anode buffer layer at a speed of 1800 - 4000 rpm to obtain an active material layer with a total thickness of 100 nm; wherein the donor material in the photoactive layer material is selected from PM6; the acceptor material is selected from Compound 1; the mass ratio of the donor material to the acceptor material is 1:1.2.

[0267] 4) Preparation of the cathode buffer layer

[0268] After thermal annealing on a hot plate at 100 °C for 10 min, the cathode buffer layer material PFN-Br was spin-coated uniformly on the active layer at a spin-coating speed of 1800 - 4000 rpm to obtain a cathode buffer layer with a thickness of 5 nm.

[0269] 5) Preparation of the cathode layer

[0270] In a high vacuum (1 × 10 -6 mbar), Ag was evaporated onto the cathode buffer layer to form a cathode layer with a thickness of 100 nm.

[0271] 6) Encapsulation

[0272] The device was encapsulated with an ultraviolet curable resin in a nitrogen glove box.

[0273]

[0274] Device Example 2: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is selected from Compound 4.

[0275] Device Example 3: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is selected from Compound 14.

[0276] Device Example 4: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is selected from Compound 18.

[0277] Device Example 5: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is selected from Compound 22.

[0278] Device Example 6: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is selected from Compound 30.

[0279] Device Example 7: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is selected from Compound 46.

[0280] Device Example 8: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is selected from Compound 49.

[0281] Device Example 9: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is Compound 66.

[0282] Device Example 10: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is Compound 75.

[0283] Device Example 11: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is Compound 83.

[0284] Device Example 12: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is Compound 90.

[0285] Device Example 13: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is Compound 123.

[0286] Device Example 14: The preparation method is the same as that of Device Example 1, except that: the acceptor material in the active layer is Compound 127.

[0287] Perform performance tests on the prepared organic solar cell devices. Under the irradiation of standard light of AM1.5G in a solar simulator (SS-F5-3A), test the current-voltage curve of the battery and calculate the photoelectric conversion efficiency:

[0288] Receptor material Photovoltaic conversion efficiency (%) Device Example 1 Compound 1 15.43 Device Example 2 Compound 4 14.86 Device Example 3 Compound 14 15.91 Device Example 4 Compound 18 13.68 Device Example 5 Compound 22 14.57 Device Example 6 Compound 30 13.74 Device Example 7 Compound 46 16.18 Device Example 8 Compound 49 16.32 Device Example 9 Compound 66 15.19 Device Example 10 Compound 75 14.28 Device Example 11 Compound 83 16.07 Device Example 12 Compound 90 14.41 Device Example 13 Compound 123 16.25 Device Example 14 Compound 127 15.60

[0289] It can be seen from the device characterization of the above device examples that the compounds protected by this application are selected from seven-membered nitrogen heterocyclic cores, and the seven-membered nitrogen heterocycles have excellent electron-donating abilities; they are connected to the terminal electron-withdrawing groups EG1 and EG2, making them have good charge mobility and appropriate energy levels. According to the organic compounds described in this application, they can be used as small molecule acceptor materials in organic solar cell devices, thereby improving the photoelectric conversion efficiency of the devices.

[0290] The above examples further illustrate the content of this application, but should not be construed as a limitation of this application. Without departing from the spirit and essence of this application, the modifications and substitutions made to the methods, steps or conditions of this application all fall within the scope of this application. If not specifically specified, the technical means used in the examples are conventional means well-known to those skilled in the art.

Claims

1. An organic compound, characterized in that: it has a structure shown in the general formula (I): wherein, Ar 1 、Ar 2 are independently selected from structural formula (A-1), structural formula (A-2), structural formula (A-3), structural formula (A-4), or a combination thereof: wherein, W is selected from O, S, CR 11 R 12 or NR 13 ; R 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 Each occurrence is independently selected from: -H, a straight-chain alkyl having 1 to 20 C atoms, a straight-chain alkoxy having 1 to 20 C atoms, a straight-chain alkylthio having 1 to 20 C atoms, a branched or cyclic alkyl having 3 to 20 C atoms, a branched or cyclic alkoxy having 3 to 20 C atoms, a branched or cyclic alkylthio having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl having 2 to 20 C atoms, an aryloxycarbonyl having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, -Cl, -Br, -F, -I, an unsubstituted aromatic group having 6 to 10 ring atoms, an unsubstituted heteroaromatic group having 5 to 10 ring atoms; * represents a connection site; Independently selected from any one of the following groups: wherein R 14 each occurrence is independently selected from -H, a straight-chain alkyl group having 1 to 6 C atoms, a branched-chain alkyl group having 3 to 6 C atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I; R 15 Each occurrence is independently selected from a straight-chain alkyl group having 1 to 6 carbon atoms and a branched-chain alkyl group having 3 to 6 carbon atoms.

2. The organic compound according to claim 1, characterized in that: the organic compound is selected from the general formula (II-1), general formula (II-2), general formula (II-3) or general formula (II-4):

3. The organic compound according to claim 1, characterized in that: R 0 selected from a straight-chain alkyl group having 1 to 15 C atoms, or a branched or cyclic alkyl group having 3 to 15 C atoms; one or more H atoms in the above groups are unsubstituted.

4. The organic compound according to claim 1, characterized in that: R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 independently selected from: -H, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear alkylthio group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a branched or cyclic alkoxy group having 3 to 20 C atoms, a branched or cyclic alkylthio group having 3 to 20 C atoms, an aromatic group having 6 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms.

5. An organic compound, characterized in that: the organic compound is selected from the following structures:

6. A mixture, characterized in that: the mixture comprises the organic compound according to any one of claims 1-5 and at least one organic functional material, and the organic functional material is selected from active layer donor materials.

7. A mixture, characterized in that: the mixture comprises the organic compound according to any one of claims 1-5 and at least one organic functional material, and the organic functional material is selected from active layer acceptor materials.

8. An electron acceptor material, characterized in that: the electron acceptor material is selected from the organic compound according to any one of claims 1-5 or the mixture according to claim 7.

9. An organic electronic device comprising at least one functional layer, characterized in that: the functional layer material is selected from the organic compound according to any one of claims 1-5 or the mixture according to claim 6 or the mixture according to claim 7.

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