An arylamine-containing organic compound and use thereof

Abstract

The application relates to the field of organic photoelectric materials, in particular to an arylamine-containing organic compound and application thereof. The arylamine-containing organic compound provided by the application adopts a thienothienothienothiophene group with an arylamine substituting a central group, a connecting unit is selected from thieno, and an end group is selected from an electron-withdrawing group. The arylamine-containing organic compound can be applied to an organic solar cell device as a photoactive layer acceptor material, and excellent photoelectric conversion efficiency is exhibited.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of organic optoelectronic materials, in particular to an organic compound containing arylamine and application thereof. BACKGROUND

[0002] Solar cells are devices that convert safe, green, renewable solar energy into electrical energy through photovoltaic effect. Organic solar cells are a new energy technology that uses organic semiconductor materials as the core part to generate voltage and form current through photovoltaic effect to realize photoelectric conversion.

[0003] The active layer of an organic solar cell is generally composed of an electron donor and an electron acceptor material. In terms of acceptor materials, currently high-efficiency electron acceptor materials are basically non-fullerene fused-ring acceptor materials, such as Y6 and its derivatives, which have a good planar skeleton, a highly delocalized electronic structure, and a strong aggregation-tendency end group, which is conducive to π-π stacking and charge transfer between molecules. However, these high-efficiency fused-ring electron acceptors have a large fused-ring ladder nucleus, and the synthesis steps are long and complex, resulting in high production costs, which is not conducive to large-scale commercial application of organic photovoltaics.

[0004] Compared with non-fullerene fused-ring acceptor materials, non-fused-ring acceptor materials have attracted attention in recent years due to their relatively simple molecular structure, relatively fewer synthesis steps, and relatively easy synthesis. However, the device efficiency based on non-fused-ring acceptor materials is currently low, and further improvement of the molecular structure is needed.

[0005] Therefore, there is still an urgent need to explore new structural design of simple and effective molecules to meet the requirements of low cost and high efficiency. SUMMARY

[0006] The purpose of the present application is to provide a new type of non-fused-ring acceptor material, which has simple synthesis steps and low cost. When applied to organic solar cell devices, it can improve the photoelectric conversion efficiency of the device.

[0007] To achieve the purpose of the present application, the technical solution is as follows:

[0008] An organic compound containing arylamine has a structure as shown in formula (I):

[0009]

[0010] Wherein:

[0011] Ar1, Ar2, Ar3, Ar4 are independently selected from substituted or unsubstituted aromatic groups having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms;

[0012] M is independently selected from O or C(CN)2 for each occurrence.

[0013] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Each occurrence is independently selected from -H (hydrogen), -D (deuterium), halogen, cyano, straight-chain alkyl with 1-20 carbon atoms, straight-chain alkoxy with 1-20 carbon atoms, straight-chain alkathio with 1-20 carbon atoms, straight-chain alkoxycarboxyl with 1-20 carbon atoms, branched or cyclic alkyl with 3-20 carbon atoms, branched or cyclic alkoxy with 3-20 carbon atoms, branched or cyclic alkathio with 3-20 carbon atoms, branched or cyclic alkoxycarboxyl with 3-20 carbon atoms, substituted or unsubstituted aromatic groups with 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic groups with 5-20 ring atoms, or groups in combination of the above groups;

[0014] R7 and R8 may or may not form a cycle; R8 and R9 may or may not form a cycle; R9 and R 10 They may form rings or not.

[0015] The term "substituted or unsubstituted" indicates that the defined group is unsubstituted or is substituted by one or more substituents R. * Instead, the R * Each occurrence is independently selected from -D (deuterium), halogen, cyano, straight-chain alkyl with 1-20 carbon atoms, straight-chain alkoxy with 1-20 carbon atoms, straight-chain alkathio with 1-20 carbon atoms, straight-chain alkoxycarboxyl with 1-20 carbon atoms, branched or cyclic alkyl with 3-20 carbon atoms, branched or cyclic alkoxy with 3-20 carbon atoms, branched or cyclic alkathio with 3-20 carbon atoms, branched or cyclic alkoxycarboxyl with 3-20 carbon atoms, aromatic group with 6-20 carbon atoms, or heteroaromatic group with 5-20 ring atoms, or a group in combination of the above groups;

[0016] The phrase "mutually cyclic or non-cyclic" means non-cyclic or preferably formed by substituted or unsubstituted 5-membered aromatic rings or 6-membered aromatic rings.

[0017] The present invention also provides a mixture comprising, as described above, an aromatic amine-containing organic compound, and at least one other organic functional material; wherein the at least one other organic functional material is selected from photoactive layer donor materials or photoactive layer acceptor materials.

[0018] The present invention also provides a composition comprising, as described above, an aromatic amine-containing organic compound or mixture, and at least one organic solvent.

[0019] The application further provides an organic electronic device comprising at least one functional layer, wherein the functional layer comprises the arylamine-containing organic compound or the mixture as described above.

[0020] Compared with the prior art, the application has the following advantages:

[0021] The core of the application adopts arylamine-substituted thienothiophene-bithienothiophene groups, the thienothiophene unit has a stable quinoid structure, a relatively narrow band gap, a strong interaction between molecules and a good stacking, the introduction of arylamine groups can effectively limit the rotation of the single bond between thienothiophene-bithienothiophene (S-N non-covalent bond interaction force), thereby improving the coplanarity of the molecules; on the other hand, arylamine has a three-dimensional molecular configuration and a strong electron-donating ability, which can effectively inhibit the excessive aggregation of the molecules and widen the spectral absorption range. The introduction of the thienyl connecting unit can adjust the effective conjugation length and stacking mode of the molecules, thereby realizing efficient charge separation and charge transport, and further improving the performance of the device.

[0022] Meanwhile, the organic compound according to the application has a simple structure, is easy to modify, is simple to synthesize, has low cost, and has good industrial application prospects. BRIEF DESCRIPTION OF DRAWINGS

[0023] Figure 1 FIG. 1 is a structural schematic diagram of an organic solar cell in an embodiment of the application. DETAILED DESCRIPTION

[0024] The application provides an arylamine-containing organic compound, a mixture, a composition and the application thereof in an organic electronic device. In order to make the purpose, technical scheme and effects of the application more clear and explicit, the application is further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the application and do not limit the application. Based on the described embodiments of the application, all other embodiments obtained by those of ordinary skill in the art without creative labor fall within the scope of the application.

[0025] The selection range of the terms "and / or", "or / and", "and / or" used in the present application includes any one of two or more relevant listed items, and also includes any and all combinations of the relevant listed items, which includes any two relevant listed items, any more relevant listed items, or all relevant listed items. It should be noted that when at least two conjunctions selected from "and / or", "or / and", "and / or" are combined to connect at least three items, it should be understood that in the present application, the 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 of A, B and A+B. For another example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C and D (i.e. the technical solution connected by "logical or"), and also includes any and all combinations of A, B, C and D, i.e. includes the combination of any two or any three of A, B, C and D, and also includes the four-item combination of A, B, C and D (i.e. the technical solution connected by "logical and").

[0026] In the present specification, when the position of a substituent on a group is not fixed, it means that any one of the connectable sites in the group can be used as the connection site. For example, may represent

[0027] In the present application, when a group contains multiple substituents with the same symbol, each substituent can be the same as or different from each other, for example The six R on the benzene ring can be the same as or different from each other.

[0028] The halogen described in the present application refers to fluorine, chlorine, bromine, iodine.

[0029] In the present application, organic photovoltaic device, organic solar cell, OPV have the same meaning and can be interchangeable.

[0030] In the present application, the active layer and the photoactive layer have the same meaning and can be interchangeable.

[0031] In the present application, "substituted" means that one or more hydrogen atoms in the substituent is replaced by a substituent.

[0032] In the present application, the "number of ring atoms" means the number of atoms among atoms constituting a ring itself of a structural compound (e.g., monocyclic compound, fused ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound) obtained by bonding atoms into a ring. When the ring is substituted with a substituent, atoms included in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. In an aromatic group, the number of ring atoms is the same as the number of carbon atoms; in a heteroaromatic group, the number of ring atoms is the number of carbon atoms plus the number of heteroatoms; for example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, the number of ring atoms of quinoline is 10, the number of ring atoms of a thienyl group is 5, and the number of ring atoms of a thienothiophene is 8.

[0033] In the present application, the "aromatic group" refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aromatic group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aromatic group can be a monocyclic aromatic group, a fused ring aromatic group, two or more monocyclic aromatic groups connected by a carbon-carbon bond in conjugation, a monocyclic aromatic group and a fused ring aromatic group connected by a carbon-carbon bond in conjugation, two or more fused ring aromatic groups connected by a carbon-carbon bond in conjugation. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond in conjugation can also be considered as the aromatic group of the present application. Preferably, the aromatic group is selected from aromatic groups having 6 to 30 C atoms; further, aromatic groups having 6 to 20 C atoms; further, aromatic groups having 6 to 10 C atoms; the aromatic group includes but is not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthene, triphenylene, pyrene, perylene, naphthacene, fluorene, and derivatives thereof.

[0034] In the present application, "heteroaromatic group" refers to a monovalent aromatic ring or its derivative comprising 1, 2, 3, 4, 5, 6 or more heteroatoms in the ring, which can be at least one of B, O, N, P, Si, Se and S. The heteroaromatic group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaromatic group can be a single aromatic ring system or a plurality of aromatic ring systems connected in conjugation through carbon-carbon bonds, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Preferably, the heteroaromatic group is selected from those having 6 to 30 ring atoms; further, from those having 6 to 20 ring atoms; further, from those having 6 to 10 ring atoms. The heteroaromatic group includes, but is not limited to, thienyl, furanyl, pyrrolyl, dioxazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, perylenyl, phenanthridinyl, perimidinyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0035] In the present application, "alkyl" can mean a straight chain, branched chain and / or cyclic alkyl group. The number of carbon atoms of the straight chain alkyl group can be 1 to 20, 1 to 16, 1 to 10, or 1 to 6; the number of carbon atoms of the branched chain alkyl group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6; the number of carbon atoms of the cyclic alkyl group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6. Non-limiting examples of the straight chain alkyl group include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, -C 10 H 21 , -C 11 H 23 , -C 12 H 25 , -C 13 H 27 , -C 14 H 29 , -C 15 H 31 , -C 16 H 33Non-limiting examples of branched alkyl groups include: isopropyl, branched alkyl group containing 4 C atoms, branched alkyl group containing 5 C atoms, branched alkyl group containing 6 C atoms, branched alkyl group containing 7 C atoms, branched alkyl group containing 8 C atoms, branched alkyl group containing 9 C atoms, branched alkyl group containing 10 C atoms, branched alkyl group containing 11 C atoms, branched alkyl group containing 12 C atoms, branched alkyl group containing 13 C atoms, branched alkyl group containing 14 C atoms, branched alkyl group containing 15 C atoms, branched alkyl group containing 16 C atoms; non-limiting examples of cyclic alkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclic alkyl group containing 7 C atoms, cyclic alkyl group containing 8 C atoms, cyclic alkyl group containing 9 C atoms, cyclic alkyl group containing 10 C atoms, cyclic alkyl group containing 11 C atoms, cyclic alkyl group containing 12 C atoms, cyclic alkyl group containing 13 C atoms, cyclic alkyl group containing 14 C atoms, cyclic alkyl group containing 15 C atoms, cyclic alkyl group containing 16 C atoms.

[0036] The term "alkoxy" refers to a group of structure "-O-alkyl", wherein alkyl is defined as above. As straight chain alkoxy indicates that the alkyl group in "-O-alkyl" is selected to be straight chain alkyl, which is defined as above; branched chain alkoxy indicates that the alkyl group in "-O-alkyl" is selected to be branched chain alkyl, which is defined as above.

[0037] The term "alkylthio" refers to a group of structure "-S-alkyl", wherein alkyl is defined as above. As straight chain alkylthio indicates that the alkyl group in "-S-alkyl" is selected to be straight chain alkyl, which is defined as above; branched chain alkylthio indicates that the alkyl group in "-S-alkyl" is selected to be branched chain alkyl, which is defined as above.

[0038] The term "alkoxycarbonyl" refers to a group of structure wherein alkyl is defined as above.

[0039] The term "cyclic or acyclic" as used herein refers to two groups being acyclic, or being cyclic by being connected to each other by a chemical bond. For example: two groups being connected to each other by a chemical bond to form a five- or six-membered aromatic or heteroaromatic ring.

[0040] In the present application, the phrase "independently selected from" means that when one or more groups are simultaneously and multiple times present in a compound, they are all independently selected, which can be the same or different.

[0041] As used herein, "combinations thereof", "any combination thereof", "any combination manner thereof", "combination" and the like include all suitable combination manners of any two, any three or any four or more groups listed.

[0042] In the present application, "further", "even further", "in particular" and the like are used for descriptive purposes only and should not be interpreted as limiting the scope of the present application.

[0043] In the present application, "optionally", "optional" and "optional" mean optional, i.e. selected from either of the two parallel schemes "with" or "without". If there are multiple "options" in a technical solution, each "option" is independent if there is no special description, and there is no contradictory or mutual restrictive relationship.

[0044] In the process of describing the structural elements of the present application, the words "including" or "containing" and the like used in the present application mean that the devices or materials appearing before the words cover the devices or materials listed after the words and their equivalents, and do not exclude other devices or materials.

[0045] In the present application, the technical features described in an open manner include both the closed technical scheme consisting of the listed features and the open technical scheme containing the listed features.

[0046] The present application provides an aromatic amine-containing organic compound having a structure as shown in formula (I):

[0047]

[0048] Wherein:

[0049] Ar1, Ar2, Ar3, Ar4 are independently selected from substituted or unsubstituted aromatic groups having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms;

[0050] M is independently selected from O or C(CN)2 for each occurrence;

[0051] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 for each occurrence, independently selected from -H (hydrogen), -D (deuterium), halogen, cyano, straight-chain alkyl having 1-20 carbon atoms, straight-chain alkoxy having 1-20 carbon atoms, straight-chain alkylthio having 1-20 carbon atoms, straight-chain alkoxy carboxyl having 1-20 carbon atoms, branched or cyclic alkyl having 3-20 carbon atoms, branched or cyclic alkoxy having 3-20 carbon atoms, branched or cyclic alkylthio having 3-20 carbon atoms, branched or cyclic alkoxy carboxyl having 3-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms, or a combination of the above groups;

[0052] R7 and R8 may or may not form a cycle; R8 and R9 may or may not form a cycle; R9 and R 10 They may form rings or not.

[0053] In this invention, "substituted or unsubstituted" means that the defined group is unsubstituted or is substituted by one or more substituents R. * Instead, the R * Each occurrence is independently selected from -D (deuterium), halogen, cyano, straight-chain alkyl with 1-20 carbon atoms, straight-chain alkoxy with 1-20 carbon atoms, straight-chain alkylthio with 1-20 carbon atoms, straight-chain alkoxycarboxyl with 1-20 carbon atoms, branched or cyclic alkyl with 3-20 carbon atoms, branched or cyclic alkoxy with 3-20 carbon atoms, branched or cyclic alkoxy with 3-20 carbon atoms, branched or cyclic alkoxycarboxyl with 3-20 carbon atoms, aromatic group with 6-20 carbon atoms, or heteroaromatic group with 5-20 ring atoms, or a group in combination of the above groups.

[0054] Furthermore, R * Each occurrence is independently selected from -D (deuterium), halogen, cyano, straight-chain alkyl with 1-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, straight-chain alkylthio with 1-10 carbon atoms, straight-chain alkoxycarboxyl with 1-10 carbon atoms, branched or cyclic alkyl with 3-10 carbon atoms, branched or cyclic alkoxy with 3-10 carbon atoms, branched or cyclic alkoxy with 3-10 carbon atoms, branched or cyclic alkoxycarboxyl with 3-10 carbon atoms, aromatic group with 6-10 carbon atoms, or heteroaromatic group with 5-10 ring atoms, or a group in combination of the above groups.

[0055] In one embodiment, Ar1, Ar2, Ar3, and Ar4 are independently selected from aromatic groups having 6-10 carbon atoms that are substituted or unsubstituted with R*, or heteroaromatic groups having 5-10 ring atoms that are substituted or unsubstituted with R*; R * Each occurrence is independently selected from -D (deuterium), halogen, cyano, straight-chain alkyl with 1-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, straight-chain alkylthio with 1-10 carbon atoms, straight-chain alkoxycarboxyl with 1-10 carbon atoms, branched or cyclic alkyl with 3-10 carbon atoms, branched or cyclic alkoxy with 3-10 carbon atoms, branched or cyclic alkoxy with 3-10 carbon atoms, branched or cyclic alkoxycarboxyl with 3-10 carbon atoms, aromatic group with 6-10 carbon atoms, or heteroaromatic group with 5-10 ring atoms, or a group in combination of the above groups.

[0056] Preferably, Ar1, Ar2, Ar3, and Ar4 are independently selected from the following structures:

[0057]

[0058] in,

[0059] R 11 Each occurrence is independently selected from -H (hydrogen), -D (deuterium), halogen, cyano, straight-chain alkyl with 1-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, straight-chain alkathio with 1-10 carbon atoms, straight-chain alkoxycarboxyl with 1-10 carbon atoms, branched or cyclic alkyl with 3-10 carbon atoms, branched or cyclic alkoxy with 3-10 carbon atoms, branched or cyclic alkathio with 3-10 carbon atoms, branched or cyclic alkoxycarboxyl with 3-10 carbon atoms, aromatic group with 6-10 carbon atoms, or heteroaromatic group with 5-10 ring atoms, or a group in combination of the above groups;

[0060] * indicates a connection point.

[0061] Preferably, the R 11 Each occurrence is independently selected from -H (hydrogen), -D (deuterium), -F, -Cl, -Br, -I, cyano, straight-chain alkyl with 1-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, straight-chain alkoxy-thio with 1-10 carbon atoms, straight-chain alkoxy-carboxyl with 1-10 carbon atoms, branched or cyclic alkyl with 3-10 carbon atoms, branched or cyclic alkoxy with 3-10 carbon atoms, branched or cyclic alkoxy with 3-10 carbon atoms, branched or cyclic alkoxy-carboxyl with 3-10 carbon atoms, phenyl, or a combination of the above groups.

[0062] More preferably, the R 11 Each occurrence is independently selected from -H (hydrogen), -D (deuterium), -F, -Cl, -Br, -I, cyano, straight-chain alkyl with 1-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, straight-chain alkoxy-thio with 1-10 carbon atoms, straight-chain alkoxy-carboxyl with 1-10 carbon atoms, branched or cyclic alkyl with 3-10 carbon atoms, branched or cyclic alkoxy with 3-10 carbon atoms, branched or cyclic alkoxy with 3-10 carbon atoms, branched or cyclic alkoxy-carboxyl with 3-10 carbon atoms, phenyl, or a combination of the above groups.

[0063] In one specific embodiment, the R 11Each occurrence is independently selected from -H (hydrogen), -D (deuterium), -F, -Cl, -Br, -I, cyano, methyl, ethyl, propyl, isopropyl, straight-chain or branched alkyl groups having 4 carbon atoms, straight-chain or branched alkyl groups having 5 carbon atoms, straight-chain or branched alkyl groups having 6 carbon atoms, straight-chain or branched alkyl groups having 7 carbon atoms, straight-chain or branched alkyl groups having 8 carbon atoms, methoxy, methylthio, ethoxy, ethylthio, straight-chain or branched alkoxy groups having 3 carbon atoms, straight-chain or branched alkoxy groups having 4 carbon atoms, straight-chain or branched alkoxy groups having 5 carbon atoms, and so on. Straight-chain or branched alkoxy groups having 6 carbon atoms, straight-chain or branched alkoxy groups having 7 carbon atoms, straight-chain or branched alkoxy groups having 8 carbon atoms, straight-chain or branched alkylthio groups having 3 carbon atoms, straight-chain or branched alkylthio groups having 4 carbon atoms, straight-chain or branched alkylthio groups having 5 carbon atoms, straight-chain or branched alkylthio groups having 6 carbon atoms, straight-chain or branched alkylthio groups having 7 carbon atoms, straight-chain or branched alkylthio groups having 8 carbon atoms, phenyl, phenyl substituted with one or more straight-chain or branched alkyl groups having 1 to 8 carbon atoms, and phenyl substituted with one or more halogen groups.

[0064] Specifically, Ar1, Ar2, Ar3, and Ar4 are independently selected from, but not limited to, the following structures:

[0065]

[0066] Where: * indicates a connection site.

[0067] In one specific embodiment, the and / or Independently selected from, but not limited to, the following structures:

[0068]

[0069] Where: * indicates a connection site.

[0070] Furthermore, the aromatic amine-containing organic compounds provided by this invention are selected from structures shown in formula (II):

[0071]

[0072] Where: R 11 The meaning is the same as described above.

[0073] In one embodiment, R1, R2, R3, R4, R5, and R6 are each selected independently from -H (hydrogen), -D (deuterium), halogen, cyano, straight-chain alkyl with 1-15 carbon atoms, straight-chain alkoxy with 1-15 carbon atoms, straight-chain alkathio with 1-15 carbon atoms, straight-chain alkoxycarboxyl with 1-15 carbon atoms, branched or cyclic alkyl with 3-15 carbon atoms, branched or cyclic alkoxy with 3-15 carbon atoms, branched or cyclic alkathio with 3-15 carbon atoms, branched or cyclic alkoxycarboxyl with 3-15 carbon atoms, substituted or unsubstituted aromatic groups with 6-10 carbon atoms, or substituted or unsubstituted heteroaromatic groups with 5-10 ring atoms, or groups in combination of the above groups.

[0074] Preferably, each occurrence of R1 and R2 is independently selected from -H (hydrogen), -D (deuterium), straight-chain alkyl groups having 1-10 carbon atoms, or branched-chain alkyl groups having 3-10 carbon atoms.

[0075] More preferably, each occurrence of R1 and R2 is independently selected from straight-chain alkyl groups having 1-10 carbon atoms or branched alkyl groups having 3-10 carbon atoms.

[0076] In one specific embodiment, each occurrence of R1 and R2 is independently selected from -H (hydrogen), -D (deuterium), -C4H9, and -C6H. 13 -C8H 17 , More preferably, R1 and R2 are selected from the same group.

[0077] Preferably, each of R3, R4, R5, and R6 is independently selected from -H (hydrogen), -D (deuterium), -F, -Cl, -Br, -I, -CF3, cyano, straight-chain alkyl with 1-15 carbon atoms, straight-chain alkoxy with 1-15 carbon atoms, straight-chain alkylthio with 1-15 carbon atoms, branched-chain alkyl with 3-15 carbon atoms, branched-chain alkoxy with 3-15 carbon atoms, and branched-chain alkylthio with 3-10 carbon atoms.

[0078] Furthermore, each occurrence of R4 and R5 is independently selected from straight-chain alkoxy groups having 1-15 carbon atoms or branched-chain alkoxy groups having 3-15 carbon atoms, or -F, -Cl, -Br, -I, -CF3, or cyano groups.

[0079] Furthermore, R4 and R5 are selected from the same group.

[0080] R7, R8, R9, R 10Each occurrence is independently selected from -H (hydrogen), -D (deuterium), -F, -Cl, -Br, -I, -CF3, cyano, straight-chain alkyl groups having 1-10 carbon atoms, or branched or cyclic alkyl groups having 3-10 carbon atoms; R7 and R8 may be cyclic or acyclic with each other; R8 and R9 may be cyclic or acyclic with each other; R9, R 10 They may form rings or not.

[0081] Preferably, "cyclic or non-cyclic" means non-cyclic or forming a substituted or unsubstituted 5-membered aromatic ring or a 6-membered aromatic ring; more preferably, forming a substituted or unsubstituted 6-membered aromatic ring.

[0082] Furthermore, the aforementioned Selected from the following structure:

[0083]

[0084] Among them, R7, R8, R9, R 10 R 12 Each occurrence is independently selected from -H (hydrogen), -D (deuterium), -F, -Cl, -Br, -I, -CF3, cyano, branched alkyl groups having 1-10 carbon atoms, or branched or cyclic alkyl groups having 3-10 carbon atoms; R7, R8, R9, R 10 R 12 Any two adjacent groups in the group do not form a ring.

[0085] In a preferred embodiment, the One M is selected from O atoms, and the other M is selected from C(CN)2.

[0086] In one specific embodiment, the Choose from any of the following structures:

[0087]

[0088] Furthermore, in equation (I) or equation (II), Selected from the same structure.

[0089] The aromatic amine-containing organic compounds according to the present invention are selected from any of the following structures, but are not limited thereto:

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] The present invention further relates to a photoactive layer acceptor material, wherein the photoactive layer acceptor material is selected from the aromatic amine-containing organic compounds described above.

[0096] The present invention further relates to a mixture comprising an aromatic amine-containing organic compound as described above and at least one other organic functional material; the other organic functional material is selected from photoactive layer donor materials or photoactive layer acceptor materials.

[0097] In one embodiment, the other organic functional material is selected from photoactive layer donor materials;

[0098] Preferably, the donor material may be selected from one or more of PBDB-T, PM6, PM7, D18, D18-Cl, PTO2, PB2, PB2F, PTVT-BT, B1, PBQx-TCl, PTQ10, PTQ11, B3T-P, and PQM-Cl;

[0099]

[0100] Where: n represents the repeating unit of the polymer, selected from an integer greater than 1.

[0101] Further, the mass ratio of the organic compound to at least one other organic functional material in the mixture is selected from 1 / 1 to 1 / 1.5; preferably, the mass ratio is selected from 1:1.2.

[0102] The present invention further relates to a composition comprising an aromatic amine-containing organic compound or mixture as described above, and at least one organic solvent. The organic solvent is selected from aliphatic hydrocarbons, chlorinated hydrocarbons, aromatic hydrocarbons, ketones, ethers, and mixtures thereof.

[0103] In one embodiment, the organic solvent is selected from dichloromethane, trichloromethane, 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, tetrahydronaphthalene, 2-methylthiophene, 3-methylthiophene, decahydronaphthalene, indene, methyl benzoate, ethyl benzoate, mesitylene, or mixtures thereof.

[0104] In a preferred embodiment, the organic solvent is selected from chlorobenzene, toluene, o-xylene, or chloroform, but is not limited thereto.

[0105] In one embodiment, the concentration of the mixture in the organic solvent according to the composition of the present invention is selected from 10-30 mg / mL; further, the concentration of the mixture in the organic solvent is selected from 10-20 mg / mL.

[0106] It is understood that the organic solvent can evaporate from the solvent system to form a thin film comprising the aromatic amine-containing organic compound.

[0107] In one embodiment, the composition is a solution. In other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from, but are not limited to, at least one of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives. In one embodiment, the composition further comprises an additive selected from, but not limited to, 1,8-diiodooctane (DIO), diphenyl ether (DPE), anthracene, 1,4-diiodobenzene (DIB), 1,3-dibromo-5-chlorobenzene (DBCl), 3,5-dichlorobromobenzene (DCBB), 1-chloronaphthalene (1-CN), 1,3,5-tribromobenzene (TBB), etc.

[0108] 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 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, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brush coating, pad printing, slot extrusion coating, etc. Slot coating, spin coating, and inkjet printing are preferred.

[0109] This invention further relates to an organic electronic device, which includes at least one functional layer comprising an aromatic amine-containing organic compound or mixture as described above, or prepared from the above composition. Preferably, the organic electronic device is selected from organic solar cells (OPV), organic light-emitting diodes (OLED), organic field-effect transistors (OFET), organic lasers, organic photodetectors (OPD), etc. In a specific embodiment, the organic electronic device is selected from organic solar cells (OPV).

[0110] Preferably, the organic electronic device comprises a first electrode, a second electrode, and one or more functional layers located between the first electrode and the second electrode, wherein the functional layers comprise an aromatic amine-containing organic compound or a mixture thereof as described above. Preferably, the functional layer comprises at least one photoactive layer, wherein the photoactive layer material comprises an aromatic amine-containing organic compound or a mixture thereof as described above.

[0111] In one embodiment, the functional layer further includes an anode buffer layer located between the anode and the photoactive layer and a cathode buffer layer located between the cathode and the photoactive layer.

[0112] It should be noted that, in order to improve the performance of organic solar cell devices, the functional layer may include other functional layers in addition to the photoactive layer, such as a charge blocking layer.

[0113] Furthermore, the organic solar cell also includes a substrate. Specifically, the substrate may be disposed on one side of the first electrode and on a different side from the functional layer.

[0114] In one embodiment, the first electrode is an anode and the second electrode is a cathode; in another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0115] In one embodiment, a substrate with excellent transparency, surface smoothness, ease of handling, and water resistance can be used as the substrate. Specifically, a glass substrate, a thin-film glass substrate, or a transparent plastic substrate can be used. The plastic substrate may include, but is not limited to, single-layer or multi-layer films such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetheretherketone (PEEK), and polyimide (PI), and substrates commonly used in organic solar cells may also be used.

[0116] At least one of the first and second electrodes is transparent or translucent to facilitate light incidence. The materials used to fabricate 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), palladium (Pd), or alloys of the aforementioned metals; conductive nanomaterials such as metal nanowires, nanoparticle pastes, graphene, carbon nanotubes; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers such as PEDOT:PSS, polypyrrole, and polyaniline; or materials with multilayer structures such as LiF / Al, LiO2 / Al, LiF / Fe, MoO3 / Al, Al:Li, Al:BaF2, and Al:BaF2:Ba, but are not limited to these.

[0117] The photoactive layer comprises electron donor materials and electron acceptor materials. In this specification, the term "active layer material" may refer to both the photoactive layer donor material and the photoactive layer acceptor material.

[0118] Specifically, the photoactive layer acceptor material is selected from the aromatic amine-containing organic compounds or mixtures mentioned above.

[0119] Preferably, the photoactive layer donor material can be a variety of polymer materials or small molecule materials. The polymer materials can be selected from polythiophene material systems, such as P3AT, P3HT, P3OT, P3DDT, etc.; fluorene-containing polymer material systems, such as PF8BT, etc.; novel structural narrow bandgap polymer material systems, such as copolymers of 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, J52, etc. The small molecule materials can be selected from one or more of the following: copper phthalocyanine (II), zinc phthalocyanine, tris[4-(5-dicyanomethylenemethyl-2-thienyl)phenyl]amine, 2,4-bis[4-(N,N-dibenzylamino)-2,6-dihydroxyphenyl]squamucolin, benzo[b]anthracene and pentabenzene, B8, B10, etc.

[0120] Specifically, the polymer material is preferably selected from one or more of PBDB-T, PM6, PM7, D18, D18-Cl, PTO2, PB2, PB2F, PTVT-BT, B1, PBQx-TCl, PTQ10, PTQ11, B3T-P, and PQM-Cl.

[0121] The photoactive layer can be formed by 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 blade coating, slot coating, and inkjet printing, but not limited thereto.

[0122] The anode buffer layer material can be selected from PEDOT:PSS, molybdenum oxide (MoOx), vanadium oxide (V2O5), nickel oxide (NiO), tungsten oxide (WO4), etc. x Preferably, x is selected from 2 or 3, etc., but not limited to this.

[0123] The cathode buffer layer material can be an electron-withdrawing metal oxide or polymer. The metal oxide can be a metal complex containing 8-hydroxyquinoline, a complex containing Alq3, a metal complex containing Liq, LiF, Ca, titanium oxide (TiOx), zinc oxide (ZnO), cesium carbonate (Cs2CO3), etc., and the polymer can be PFN-Br or PFN or PDINO or PDINN or PNDIT-F3N-Br or PNDIT-F3N, etc., but is not limited to these.

[0124] This invention also relates to the application of organic solar cells according to the invention in various devices, including, but not limited to, building-integrated photovoltaics (BIPV), electronic shelf labels, indoor photovoltaics, the Internet of Things, smart agriculture, etc.

[0125] The present invention will now be described in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of the present invention. Under the guidance of the inventive concept, those skilled in the art should realize that any changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0126] Examples of aromatic amine-containing organic compounds and organic electronic devices according to the present invention are provided herein, but the present invention is not limited to the following embodiments.

[0127] Compound preparation:

[0128] Example 1: Synthesis of compound (2)

[0129]

[0130] Synthesis of compounds 1-2:

[0131] Accurately weigh compound 1-1 (6 g, 10 mmol), 4,4'-dimethyldiphenylamine (4.4 g, 22 mmol), Pd(dba)2 (0.17 g, 0.3 mmol), cuprous iodide (0.19 g, 1 mmol), sodium tert-butoxide (4.8 g, 50 mmol), and 1,10-phenanthroline (0.36 g, 2 mmol) and add them sequentially to a 250 mL three-necked flask. Add approximately 80 mL of anhydrous xylene, purge with nitrogen three times, and then heat to 150 °C for 4 hours. After the reactants have completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 7.67 g of compound 1-2, yield: 91.6%. MS: 837.42

[0132] Synthesis of compounds 1-3:

[0133] Accurately weigh compounds 1-2 (7.5 g, 9 mmol) into a 250 mL three-necked flask, add approximately 80 mL of anhydrous DMF, purge with nitrogen three times, and cool to approximately 0 °C. Slowly add a DMF solution of NBS (3.5 g, 19.8 mmol) dropwise to the reaction system, then allow it to warm naturally to room temperature. React for 6 hours until the reactants are completely reacted, then quench with water, extract with ethyl acetate, combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as the eluent to obtain approximately 7.7 g of compounds 1-3, yield: 86%. MS: 995.81

[0134] Synthesis of compounds 1-5:

[0135] Accurately weigh compounds 1-3 (7.7 g, 7.7 mmol), compounds 1-4 (8.5 g, 17 mmol), and Pd(PPh3)2Cl2 (0.14 g, 0.2 mmol) and add them sequentially to a 250 mL three-necked flask. Add approximately 100 mL of anhydrous toluene, purge with nitrogen three times, and then heat to 90 °C for two hours. After the reactants have completely reacted, cool to room temperature, wash with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 8.2 g of compounds 1-5, yield: 84.7%. MALDI-TOF-MS: 1258.24

[0136] Synthesis of compounds 1-6:

[0137] Accurately weigh 8.2 g (6.5 mmol) of compounds 1-5 into a 250 mL three-necked flask, add approximately 90 mL of anhydrous DMF, purge with nitrogen three times, add 3 mL of phosphorus oxychloride, and then heat to 90 °C and react for 6 hours. After the starting material has completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 15:1 (v / v) as eluent to obtain approximately 7.2 g of compounds 1-6, yield: 84.3%. MALDI-TOF-MS: 1313.64

[0138] Synthesis of compound (2):

[0139] Accurately weigh compounds 1-6 (1.3 g, 1 mmol) and compounds 1-7 (0.51 g, 2.2 mmol), add them to a 100 mL three-necked flask, add 50 mL of chloroform, replace with nitrogen three times, then add 5 mL of pyridine, heat to reflux for 12 h, cool the reaction to room temperature, quench with water, and extract with DCM. The crude product is purified by silica gel column chromatography with DCM:PE = 1:1 (volume ratio) as the eluent to obtain approximately 0.89 g of compound (2), with a yield of 51.2%. MALDI-TOF-MS: 1738.33.

[0140] Example 2: Synthesis of compound (20)

[0141]

[0142] Synthesis of compounds 2-3:

[0143] Accurately weigh compound 2-1 (6.6 g, 10 mmol), compound 2-2 (6.2 g, 22 mmol), Pd(dba)2 (0.17 g, 0.3 mmol), cuprous iodide (0.19 g, 1 mmol), sodium tert-butoxide (4.8 g, 50 mmol), and 1,10-phenanthroline (0.36 g, 2 mmol) into a 250 mL three-necked flask. Add approximately 80 mL of anhydrous xylene, purge with nitrogen three times, and then heat to 150 °C for 4 hours. After the reactants have completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 9.1 g of compound 2-3, yield: 86.1%. MS: 1061.89

[0144] Synthesis of compounds 2-4:

[0145] Accurately weigh 9.1 g (8.6 mmol) of compound 2-3 into a 250 mL three-necked flask, add approximately 90 mL of anhydrous DMF, purge the mixture three times with nitrogen, and then cool to approximately 0 °C. Slowly add 3.4 g (18.9 mmol) of NBS in DMF solution to the reaction system, then allow it to naturally warm to room temperature. React for 6 hours. After the reactants have completely reacted, quench with water, extract with ethyl acetate, combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as the eluent to obtain approximately 8.9 g of compound 2-4, yield: 84.9%. MALDI-TOF-MS: 1220.05

[0146] Synthesis of compounds 2-5:

[0147] Accurately weigh compounds 2-4 (8.9 g, 7.3 mmol), compounds 1-4 (8 g, 16 mmol), and Pd(PPh3)2Cl2 (0.14 g, 0.2 mmol) into a 250 mL three-necked flask. Add approximately 100 mL of anhydrous toluene, purge with nitrogen three times, and then heat to 90 °C for two hours. After the reactants have completely reacted, cool to room temperature, wash with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 9.1 g of compounds 2-5, yield: 84.1%. MALDI-TOF-MS: 1482.86

[0148] Synthesis of compounds 2-6:

[0149] Compound 2-5 (8.2 g, 6.1 mmol) was accurately weighed and added to a 250 mL three-necked flask. Approximately 90 mL of anhydrous DMF was added, and the mixture was purged with nitrogen three times. Then, 3 mL of phosphorus oxychloride was added, and the mixture was heated to 90 °C and reacted for 6 hours. After the reactants had completely reacted, the mixture was cooled to room temperature, quenched with water, and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 15:1 (v / v) as the eluent, yielding approximately 7.5 g of compound 2-6, with a yield of 79.9%. MALDI-TOF-MS: 1538.86

[0150] Synthesis of compound (20):

[0151] Accurately weigh compound 2-6 (1.5 g, 1 mmol) and compound 2-7 (0.69 g, 2.2 mmol), add them to a 100 mL three-necked flask, add 50 mL of chloroform, replace with nitrogen three times, then add 5 mL of pyridine, heat to reflux for 12 h, cool the reaction to room temperature, quench with water, extract with DCM, purify the crude product with silica gel column chromatography, using DCM:PE = 1:1 (volume ratio) as the eluent, to obtain approximately 1.34 g of compound (20), with a yield of 63%. MALDI-TOF-MS: 2128.79.

[0152] Example 3: Synthesis of compound (35)

[0153]

[0154] Synthesis of compound 3-3:

[0155] Accurately weigh compound 3-1 (4.4 g, 10 mmol), compound 3-2 (7.4 g, 22 mmol), Pd(dba)2 (0.17 g, 0.3 mmol), cuprous iodide (0.19 g, 1 mmol), sodium tert-butoxide (4.8 g, 50 mmol), and 1,10-phenanthroline (0.36 g, 2 mmol) into a 250 mL three-necked flask. Add approximately 80 mL of anhydrous xylene, purge with nitrogen three times, and then heat to 150 °C for 4 hours. After the reactants have completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 8.6 g of compound 3-3, yield: 90.6%. MS: 949.84

[0156] Synthesis of compounds 3-4:

[0157] Accurately weigh 8.6 g (9 mmol) of compound 3-3 into a 250 mL three-necked flask, add approximately 90 mL of anhydrous DMF, purge the mixture three times with nitrogen, and then cool to approximately 0 °C. Slowly add 3.5 g (19.8 mmol) of NBS in DMF solution to the reaction system, then allow it to naturally warm to room temperature for 6 hours. After the reactants have completely reacted, quench with water, extract with ethyl acetate, combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as the eluent to obtain approximately 8.9 g of compound 3-4, yield: 89.3%. MS: 1108.08

[0158] Synthesis of compounds 3-6:

[0159] Accurately weigh compounds 3-4 (8.9 g, 8 mmol), 3-5 (9.2 g, 16 mmol), and Pd(PPh3)2Cl2 (0.14 g, 0.2 mmol) and add them sequentially to a 250 mL three-necked flask. Add approximately 100 mL of anhydrous toluene, purge with nitrogen three times, and then heat to 90 °C for two hours. After the reactants have completely reacted, cool to room temperature, wash with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 10.8 g of compound 3-6, yield: 89.1%. MALDI-TOF-MS: 1514.42

[0160] Synthesis of compounds 3-7:

[0161] Accurately weigh 10.8 g (7.2 mmol) of compound 3-6 into a 250 mL three-necked flask, add approximately 100 mL of anhydrous DMF, purge with nitrogen three times, then add 4 mL of phosphorus oxychloride and heat to 90 °C for 6 hours. After the starting material has completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry with anhydrous sodium sulfate, remove excess solvent by vacuum distillation, and perform silica gel column chromatography with PE:EA = 15:1 (v / v). This yields approximately 9.8 g of compound 3-7, yield: 86.7%. MALDI-TOF-MS: 1570.85

[0162] Synthesis of compound (35):

[0163] Accurately weigh compound 3-7 (1.6 g, 1 mmol) and compound 1-7 (0.51 g, 2.2 mmol), add them to a 100 mL three-necked flask, add 50 mL of chloroform, replace with nitrogen three times, then add 5 mL of pyridine, heat to reflux for 12 h, cool the reaction to room temperature, quench with water and extract with DCM, purify the crude product with silica gel column chromatography, using DCM:PE = 1:1 (volume ratio) as the eluent, to obtain approximately 1.35 g of compound (35), with a yield of 67.6%. MALDI-TOF-MS: 1995.07.

[0164] Example 4: Synthesis of Compound 37

[0165]

[0166] Synthesis of compound 4-2:

[0167] Accurately weigh compounds 3-4 (5.5 g, 5 mmol), 4-1 (2.6 g, 16 mmol), and Pd(PPh3)2Cl2 (0.14 g, 0.2 mmol) and add them sequentially to a 100 mL three-necked flask. Add approximately 50 mL of anhydrous toluene, purge with nitrogen three times, and then heat to 90 °C for two hours. After the reactants have completely reacted, cool to room temperature, wash with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 5.1 g of compound 4-2, yield: 88.7%. MS: 1149.89

[0168] Synthesis of compound 4-3:

[0169] Compound 4-2 (5.1 g, 4.4 mmol) was accurately weighed and added to a 100 mL three-necked flask. Approximately 50 mL of anhydrous DMF was added, and the mixture was purged with nitrogen three times. Then, 2 mL of phosphorus oxychloride was added, and the mixture was heated to 90 °C and reacted for 6 hours. After the reactants had completely reacted, the mixture was cooled to room temperature, quenched with water, and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 15:1 (v / v) as the eluent, yielding approximately 4.5 g of compound 4-3, with a yield of 82.9%. MALDI-TOF-MS: 1205.87

[0170] Synthesis of compound (37):

[0171] Accurately weigh compound 4-3 (1.2 g, 1 mmol) and compound 1-7 (0.51 g, 2.2 mmol), add them to a 100 mL three-necked flask, add 50 mL of chloroform, replace with nitrogen three times, then add 5 mL of pyridine, heat to reflux for 12 h, cool the reaction to room temperature, quench with water and extract with DCM, purify the crude product with silica gel column chromatography, using DCM:PE = 1:1 (volume ratio) as the eluent, to obtain compound (37) about 0.95 g, with a yield of 58.3%. MALDI-TOF-MS: 1630.19.

[0172] Example 5: Synthesis of compound (44)

[0173]

[0174] Synthesis of compound 5-2:

[0175] Accurately weigh compounds 3-1 (4.4 g, 10 mmol), 5-1 (5.0 g, 22 mmol), Pd(dba)2 (0.17 g, 0.3 mmol), cuprous iodide (0.19 g, 1 mmol), sodium tert-butoxide (4.8 g, 50 mmol), and 1,10-phenanthroline (0.36 g, 2 mmol) and add them sequentially to a 250 mL three-necked flask. Add approximately 80 mL of anhydrous xylene, purge with nitrogen three times, and then heat to 150 °C for 4 hours. After the reactants have completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 6.7 g of compound 5-2, yield: 92.5%. MS: 725.88

[0176] Synthesis of compound 5-3:

[0177] Accurately weigh 6.5 g (9 mmol) of compound 5-2 into a 250 mL three-necked flask, add approximately 90 mL of anhydrous DMF, purge with nitrogen three times, and cool to approximately 0 °C. Slowly add 3.5 g (19.8 mmol) of NBS in DMF solution to the reaction system, then allow to naturally warm to room temperature for 6 hours. After the reactants have completely reacted, quench with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 6.4 g of compound 5-3, yield: 81.1%. MS: 882.63

[0178] Synthesis of compound 5-4:

[0179] Accurately weigh compound 5-3 (6.3 g, 7.2 mmol), compound 4-1 (4.8 g, 14.4 mmol), and Pd(PPh3)2Cl2 (0.14 g, 0.2 mmol) into a 250 mL three-necked flask. Add approximately 100 mL of anhydrous toluene, purge with nitrogen three times, and then heat to 90 °C for two hours. After the reactants have reacted completely, cool to room temperature, wash with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 6.6 g of compound 5-4, yield: 87.3%. MS: 1057.39

[0180] Synthesis of compound 5-5:

[0181] Compound 5-4 (5.3 g, 5 mmol) was accurately weighed and added to a 250 mL three-necked flask. Approximately 100 mL of anhydrous DMF was added, and the mixture was purged with nitrogen three times. Then, 2 mL of phosphorus oxychloride was added, and the mixture was heated to 90 °C and reacted for 6 hours. After the starting material had completely reacted, the mixture was cooled to room temperature, quenched with water, and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 15:1 (v / v) as the eluent, yielding approximately 4.3 g of compound 5-5, yield: 76.7%. MS: 1113.59

[0182] Synthesis of compound (44):

[0183] Accurately weigh compound 5-5 (1.1 g, 1 mmol) and compound 5-6 (0.58 g, 2.2 mmol), add them to a 100 mL three-necked flask, add 50 mL of chloroform, purge with nitrogen three times, then add 5 mL of pyridine, reflux for 12 h, cool the reaction to room temperature, quench with water, and extract with DCM. The crude product is purified by silica gel column chromatography with DCM:PE = 1:1 (volume ratio) as the eluent, yielding approximately 1.02 g of compound (44), with a yield of 63.6%. MALDI-TOF-MS: 1603.14

[0184] Example 6: Synthesis of compound (46)

[0185]

[0186] Synthesis of compound 6-2:

[0187] Accurately weigh compounds 1-1 (6 g, 10 mmol), 6-1 (4.8 g, 22 mmol), Pd(dba)2 (0.17 g, 0.3 mmol), cuprous iodide (0.19 g, 1 mmol), sodium tert-butoxide (4.8 g, 50 mmol), and 1,10-phenanthroline (0.36 g, 2 mmol) and add them sequentially to a 250 mL three-necked flask. Add approximately 80 mL of anhydrous xylene, purge with nitrogen three times, and then heat to 150 °C for 4 hours. After the reactants have completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 7.5 g of compound 6-2, yield: 85.4%. MS: 878.50

[0188] Synthesis of compound 6-3:

[0189] Compound 6-2 (7.5 g, 8.5 mmol) was accurately weighed and added to a 250 mL three-necked flask. Approximately 90 mL of anhydrous DMF was added, and the mixture was purged with nitrogen three times. The temperature was then lowered to approximately 0 °C. A DMF solution of NBS (3.3 g, 18.7 mmol) was slowly added dropwise to the reaction system. The mixture was then allowed to warm naturally to room temperature for 6 hours. After the reactants had completely reacted, the reaction was quenched with water, extracted with ethyl acetate, and the organic phases were combined. After drying with anhydrous sodium sulfate, excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 30:1 (v / v) as the eluent, yielding approximately 7.6 g of compound 6-3, with a yield of 86.3%. MS: 1036.62

[0190] Synthesis of compound 6-4:

[0191] Accurately weigh compound 6-3 (7.6 g, 7.3 mmol), compound 1-4 (7.3 g, 14.6 mmol), and Pd(PPh3)2Cl2 (0.14 g, 0.2 mmol) into a 250 mL three-necked flask. Add approximately 100 mL of anhydrous toluene, purge with nitrogen three times, and then heat to 90 °C for two hours. After the reactants have reacted completely, cool to room temperature, wash with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 8.3 g of compound 6-4, yield: 87.5%. MALDI-TOF-MS: 1298.89

[0192] Synthesis of compound 6-5:

[0193] Compound 6-4 (8.3 g, 6.4 mmol) was accurately weighed and added to a 250 mL three-necked flask. Approximately 100 mL of anhydrous DMF was added, and the mixture was purged with nitrogen three times. Then, 4 mL of phosphorus oxychloride was added, and the mixture was heated to 90 °C and reacted for 6 hours. After the reactants had completely reacted, the mixture was cooled to room temperature, quenched with water, and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 15:1 (v / v) as the eluent, yielding approximately 7.6 g of compound 6-5, with a yield of 87.7%. MALDI-TOF-MS: 1354.88

[0194] Synthesis of compound (46):

[0195] Accurately weigh compounds 6-5 (1.35 g, 1 mmol) and 1-7 (0.51 g, 2.2 mmol), add them to a 100 mL three-necked flask, add 50 mL of chloroform, purge with nitrogen three times, then add 5 mL of pyridine, reflux for 12 h, cool to room temperature, quench with water, and extract with DCM. Purify the crude product by silica gel column chromatography using DCM:PE = 1:1 (volume ratio) as eluent to obtain approximately 1.2 g of compound (46), with a yield of 67.4%. MALDI-TOF-MS: 1779.31

[0196] Example 7: Synthesis of compound (56)

[0197]

[0198] Synthesis of compound 7-2:

[0199] Accurately weigh compound 1-1 (6 g, 10 mmol), compound 7-1 (4.5 g, 22 mmol), Pd(dba)2 (0.17 g, 0.3 mmol), cuprous iodide (0.19 g, 1 mmol), sodium tert-butoxide (4.8 g, 50 mmol), and 1,10-phenanthroline (0.36 g, 2 mmol) into a 250 mL three-necked flask. Add approximately 80 mL of anhydrous xylene, purge with nitrogen three times, and then heat to 150 °C for 4 hours. After the reactants have completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 7.2 g of compound 7-2, yield: 84.4%. MS: 853.33

[0200] Synthesis of compound 7-3:

[0201] Compound 7-2 (7.2 g, 8.4 mmol) was accurately weighed and added to a 250 mL three-necked flask. Approximately 90 mL of anhydrous DMF was added, and the mixture was purged with nitrogen three times. The temperature was then lowered to approximately 0 °C. A DMF solution of NBS (3.3 g, 18.5 mmol) was slowly added dropwise to the reaction system. The mixture was then allowed to warm naturally to room temperature for 6 hours. After the reactants had completely reacted, the reaction was quenched with water, extracted with ethyl acetate, and the organic phases were combined. After drying with anhydrous sodium sulfate, excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 30:1 (v / v) as the eluent, yielding approximately 7.5 g of compound 7-3, in 88.3% yield. MS: 10¹¹.29 g.

[0202] Synthesis of compound 7-5:

[0203] Accurately weigh compound 7-3 (7.5 g, 7.4 mmol), compound 7-4 (4.9 g, 14.8 mmol), and Pd(PPh3)2Cl2 (0.14 g, 0.2 mmol) into a 250 mL three-necked flask. Add approximately 100 mL of anhydrous toluene, purge with nitrogen three times, and then heat to 90 °C for two hours. After the reactants have reacted completely, cool to room temperature, wash with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 7.3 g of compound 7-5, yield: 83.2%. MS: 1185.76

[0204] Synthesis of compound 7-6:

[0205] Compound 7-5 (7.3 g, 6.2 mmol) was accurately weighed and added to a 250 mL three-necked flask. Approximately 100 mL of anhydrous DMF was added, and the mixture was purged with nitrogen three times. Then, 4 mL of phosphorus oxychloride was added, and the mixture was heated to 90 °C and reacted for 6 hours. After the reactants had completely reacted, the mixture was cooled to room temperature, quenched with water, and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 15:1 (v / v) as the eluent, yielding approximately 5.8 g of compound 7-6, with a yield of 75.3%. MALDI-TOF-MS: 1241.64

[0206] Synthesis of compound (46):

[0207] Accurately weigh compound 7-6 (1.24 g, 1 mmol) and compound 7-7 (0.54 g, 2.2 mmol), add them to a 100 mL three-necked flask, add 50 mL of chloroform, purge with nitrogen three times, then add 5 mL of pyridine, reflux for 12 h, cool to room temperature, quench with water, and extract with DCM. Purify the crude product by silica gel column chromatography, using DCM:PE = 1:1 (volume ratio) as the eluent, to obtain approximately 1.05 g of compound (56), with a yield of 62%. MALDI-TOF-MS: 1694.29

[0208] Example 8: Synthesis of compound (62)

[0209]

[0210] Synthesis of compound 8-2:

[0211] Accurately weigh compounds 1-1 (6 g, 10 mmol), 8-1 (5 g, 22 mmol), Pd(dba)2 (0.17 g, 0.3 mmol), cuprous iodide (0.19 g, 1 mmol), sodium tert-butoxide (4.8 g, 50 mmol), and 1,10-phenanthroline (0.36 g, 2 mmol) and add them sequentially to a 250 mL three-necked flask. Add approximately 80 mL of anhydrous xylene, purge with nitrogen three times, and then heat to 150 °C for 4 hours. After the reactants have completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 8.2 g of compound 8-2, yield: 91%. MS: 901.70

[0212] Synthesis of compound 8-3:

[0213] Compound 8-2 (8.2 g, 9.1 mmol) was accurately weighed and added to a 250 mL three-necked flask. Approximately 90 mL of anhydrous DMF was added, and the mixture was purged with nitrogen three times. The temperature was lowered to approximately 0 °C, and a DMF solution of NBS (3.6 g, 20 mmol) was slowly added dropwise. The mixture was then allowed to warm naturally to room temperature for 6 hours. After the reactants had completely reacted, the reaction was quenched with water, extracted with ethyl acetate, and the organic phases were combined. After drying with anhydrous sodium sulfate, excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 30:1 (v / v) as the eluent, yielding approximately 8.3 g of compound 8-3, with a yield of 86.1%. MS: 1060.63

[0214] Synthesis of compound 8-4:

[0215] Accurately weigh compound 8-3 (8.3 g, 7.8 mmol), compound 1-4 (7.8 g, 15.6 mmol), and Pd(PPh3)2Cl2 (0.14 g, 0.2 mmol) into a 250 mL three-necked flask. Add approximately 100 mL of anhydrous toluene, purge with nitrogen three times, and then heat to 90 °C for two hours. After the reactants have reacted completely, cool to room temperature, wash with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 8.4 g of compound 8-4, yield: 81.5%. MALDI-TOF-MS: 1322.49

[0216] Synthesis of compound 8-5:

[0217] Compound 8-4 (8.4 g, 6.4 mmol) was accurately weighed and added to a 250 mL three-necked flask. Approximately 100 mL of anhydrous DMF was added, and the mixture was purged with nitrogen three times. Then, 4 mL of phosphorus oxychloride was added, and the mixture was heated to 90 °C and reacted for 6 hours. After the reactants had completely reacted, the mixture was cooled to room temperature, quenched with water, and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 15:1 (v / v) as the eluent, yielding approximately 7.2 g of compound 8-5, with a yield of 81.7%. MALDI-TOF-MS: 1378.12

[0218] Synthesis of compound (62):

[0219] Accurately weigh compound 8-5 (1.4 g, 1 mmol) and compound 5-6 (0.58 g, 2.2 mmol), add them to a 100 mL three-necked flask, add 50 mL of chloroform, purge with nitrogen three times, then add 5 mL of pyridine, reflux for 12 h, cool to room temperature, quench with water, and extract with DCM. Purify the crude product by silica gel column chromatography using DCM:PE = 1:1 (volume ratio) as eluent to obtain approximately 1.26 g of compound (62), with a yield of 67.4%. MALDI-TOF-MS: 1868.30

[0220] Example 9: Synthesis of compound (66)

[0221]

[0222] Synthesis of compound 9-1:

[0223] Accurately weigh compound 3-1 (4.4 g, 10 mmol), 4,4'-dimethyldiphenylamine (4.4 g, 22 mmol), Pd(dba)2 (0.17 g, 0.3 mmol), cuprous iodide (0.19 g, 1 mmol), sodium tert-butoxide (4.8 g, 50 mmol), and 1,10-phenanthroline (0.36 g, 2 mmol) and add them sequentially to a 250 mL three-necked flask. Add approximately 80 mL of anhydrous xylene, purge with nitrogen three times, and then heat to 150 °C for 4 hours. After the reactants have completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 5.8 g of compound 9-1, yield: 87.1%. MS: 669.11

[0224] Synthesis of compound 9-2:

[0225] Accurately weigh 5.7 g (8.5 mmol) of compound 9-1 into a 250 mL three-necked flask, add approximately 90 mL of anhydrous DMF, purge with nitrogen three times, and cool to approximately 0 °C. Slowly add 3.3 g (18.7 mmol) of NBS in DMF solution to the reaction system, then allow to naturally warm to room temperature for 6 hours. After the reactants have completely reacted, quench with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 6.0 g of compound 9-2, yield: 84.8%. MS: 826.93

[0226] Synthesis of compound 9-3:

[0227] Accurately weigh compound 9-2 (6.0 g, 7.2 mmol), compound 1-4 (7.2 g, 14.4 mmol), and Pd(PPh3)2Cl2 (0.14 g, 0.2 mmol) into a 250 mL three-necked flask. Add approximately 100 mL of anhydrous toluene, purge with nitrogen three times, and then heat to 90 °C for two hours. After the reactants have reacted completely, cool to room temperature, wash with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 30:1 (v / v) as eluent to obtain approximately 5.7 g of compound 9-3, yield: 73.2%. MS: 1089.68

[0228] Synthesis of compound 9-4:

[0229] Accurately weigh 5.4 g (5 mmol) of compound 9-3 into a 250 mL three-necked flask, add approximately 100 mL of anhydrous DMF, purge with nitrogen three times, then add 2 mL of phosphorus oxychloride and heat to 90 °C for 6 hours. After the starting material has completely reacted, cool to room temperature, quench with water, and extract with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, remove excess solvent by vacuum distillation, and perform silica gel column chromatography with PE:EA = 15:1 (v / v) as eluent to obtain approximately 3.8 g of compound 9-4, yield: 66.3%. MS: 1145.13

[0230] Synthesis of compound (66):

[0231] Accurately weigh compound 9-4 (1.1 g, 1 mmol) and compound 1-7 (0.51 g, 2.2 mmol) and add them to a 100 mL three-necked flask. Add 50 mL of chloroform, purge with nitrogen three times, then add 5 mL of pyridine. Reflux the mixture for 12 h. Cool the reaction to room temperature, quench with water, and extract with DCM. Purify the crude product using silica gel column chromatography with DCM:PE = 1:1 (volume ratio) as the eluent to obtain approximately 0.94 g of compound (66), with a yield of 60.1%. MALDI-TOF-MS: 1570.31

[0232] OPV device fabrication and characterization

[0233] The following specific examples illustrate in detail the fabrication process of OPV devices using the aforementioned aromatic amine-containing organic compounds. Figure 1 As shown, the OPV device structure is as follows: Indium Tin Oxide (ITO) / PEDOT:PSS / Active Layer / PDINN / Ag

[0234] The fabrication steps of device example 1 are as follows:

[0235] 1) ITO substrate cleaning:

[0236] Clean the ITO conductive glass with detergent, rinse it thoroughly, and then ultrasonically clean it for 15 minutes with deionized water, acetone, and isopropanol. After that, dry it with nitrogen and treat it in a plasma cleaner for 5 minutes to further clean the surface and improve wettability.

[0237] 2) Preparation of the anode buffer layer

[0238] PEDOT:PSS (Clevios) in the air TM PVP Al 4083 was uniformly spin-coated onto ITO at a spin speed of 3000-4000 rpm and dried at 150℃ for 15 min to obtain an anodic buffer layer with a thickness of 20 nm.

[0239] 3) Preparation of photoactive layer

[0240] In a glove box (inert gas atmosphere), the photoactive layer material (the concentration of the mixture of the donor and acceptor materials in chloroform is 15 mg / mL) was uniformly spin-coated onto the anode buffer layer at a rotation speed of 1800-4000 rpm to obtain an active material layer with a total thickness of 100 nm. The donor material in the photoactive layer material was selected from PM6, and the acceptor material was selected from compound (2), with a mass ratio of donor to acceptor material of 1:1.

[0241]

[0242] 4) Preparation of cathode buffer layer

[0243] After annealing on a hot plate at 100°C for 10 min, the cathode buffer layer material PDINN (prepared by dissolving PDINN in methanol to a concentration of 1.2 mg / mL) was uniformly spin-coated onto the active layer at a spin speed of 3000-4000 rpm to obtain a cathode buffer layer with a thickness of 10 nm.

[0244] 5) Cathode layer preparation

[0245] In high vacuum (1×10) -6 Ag was deposited onto the cathode buffer layer in millibars to form a cathode layer with a thickness of 100 nm, at a deposition rate of 4 angstroms / second.

[0246] 6) Packaging

[0247] The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0248] Device Examples 2-9

[0249] The acceptor material compound (2) in the photoactive layer of Device Example 1 was replaced with compounds (20), (35), (37), (44), (46), (56), (62), and (66), respectively. The other steps and methods were the same, and the devices prepared were designated as Device Examples 2 to 8. For details of the acceptor materials in the specific device examples, please refer to Table 1.

[0250] The performance of the fabricated organic solar cell device was tested. Under AM1.5G standard light irradiation using a solar simulator (SS-F5-3A), the cell current-voltage curve was measured, and the photoelectric conversion efficiency was calculated.

[0251] Table 1

[0252] Photoactive layer acceptor material Photoelectric conversion efficiency (%) Device Example 1 Compound (2) 16.85 Device Example 2 Compound (20) 16.31 Device Example 3 Compound (35) 15.94 Device Example 4 Compound (37) 15.58 Device Example 5 Compound (44) 15.37 Device Example 6 Compound (46) 17.03 Device Example 7 Compound (56) 14.72 Device Example 8 Compound (62) 16.49 Device Example 9 Compound (66) 15.92

[0253] As shown in Table 1, the aromatic amine-containing organic compounds described in this invention exhibit excellent photoelectric conversion efficiency when used as photoactive layer acceptor materials in OPV devices. This is because the core framework of this invention uses thiophene-thiophene-thiophene groups substituted with aromatic amines. The thiophene-thiophene units possess a stable quinone structure, a narrow band gap, strong intermolecular interactions, and good packing. The introduction of aromatic amine groups effectively restricts the rotation of single bonds between thiophene-thiophene-thiophene (S-N non-covalent interactions), thereby improving the coplanarity of the molecules. Furthermore, aromatic amines have a three-dimensional molecular configuration and strong electron-donating ability, which can effectively suppress excessive molecular aggregation and broaden the spectral absorption range. In addition, the introduction of the thiophene connecting unit can adjust the effective conjugation length and packing mode of the molecules, thereby achieving efficient charge separation and charge transport, and ultimately improving device performance.

[0254] Compared with device example 9, device example 1 has an efficiency improvement of 6%. The reason is that R1 and R2 of compound (2) have been further modified compared with compound (66). R1 ​​and R2 of compound (2) are selected from alkyl groups. Alkyl groups improve the solubility of the compound and optimize the molecular morphology of the compound, so that it exhibits better device photoelectric conversion efficiency when paired with donor material.

[0255] The preferred embodiments of this application have been described in detail above. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

Claims

1. An organic compound containing aromatic amines, characterized in that: The aromatic amine-containing organic compound has the structure described in formula (I): Equation (I) in: Ar1, Ar2, Ar3, and Ar4 are selected independently. ;R 11 Each occurrence is independently selected from -H, -D, halogen, cyano, straight-chain alkyl with 1-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, straight-chain alkylthio with 1-10 carbon atoms, branched or cyclic alkyl with 3-10 carbon atoms, branched or cyclic alkoxy with 3-10 carbon atoms, or branched or cyclic alkylthio with 3-10 carbon atoms; * indicates a linking site; Each time M appears, it is independently selected from O or C(CN)2; Each time R1 and R2 appear, they are independently selected from -H, -D, straight-chain alkyl groups having 1-10 carbon atoms, or branched alkyl groups having 3-10 carbon atoms. Each time R3 and R6 appear, they are independently selected from -H, -D, straight-chain alkoxy groups with 1-15 carbon atoms, and branched-chain alkoxy groups with 3-15 carbon atoms; Each time R4 and R5 appear, they are independently selected from straight-chain alkoxy groups having 1-15 carbon atoms or branched-chain alkoxy groups having 3-15 carbon atoms. R7, R8, R9, R 10 Each occurrence is independently selected from -H, -D, -F, -Cl, -Br, -I, -CF3, cyano, straight-chain alkyl with 1-10 carbon atoms, or branched or cyclic alkyl with 3-10 carbon atoms; R7 and R8 may or may not form a cycle; R8 and R9 may or may not form a cycle; R9 and R 10 They may form rings or not.

2. The aromatic amine-containing organic compound according to claim 1, characterized in that: Ar1, Ar2, Ar3, and Ar4 are independently selected from the following structures: 。 3. The aromatic amine-containing organic compound according to claim 1, characterized in that: , Independently selected from the following structures: 。 4. An aromatic amine-containing organic compound according to any one of claims 1-3, characterized in that: Each time R1 and R2 appear, they are independently selected from straight-chain alkyl groups having 1-10 carbon atoms or branched alkyl groups having 3-10 carbon atoms.

5. An aromatic amine-containing organic compound according to any one of claims 1-3, characterized in that: In formula (I), Choose from any of the following structures: ； Among them, R7, R8, R9, R 10 R 12 Each occurrence is independently selected from -H, -D, -F, -Cl, -Br, -I, -CF3, cyano, branched alkyl groups having 1-10 carbon atoms, or branched or cyclic alkyl groups having 3-10 carbon atoms.

6. The aromatic amine-containing organic compound according to claim 5, characterized in that: The One M is selected from O atoms, and the other M is selected from C(CN)2.

7. The aromatic amine-containing organic compound according to claim 1, characterized in that: The aromatic amine-containing organic compound is selected from any of the following structures: 。 8. A mixture, characterized in that: The mixture comprises an aromatic amine-containing organic compound as described in any one of claims 1-7, and at least one other organic functional material; the at least one other organic functional material is selected from photoactive layer donor materials or photoactive layer acceptor materials.

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

10. An organic electronic device comprising at least one functional layer, characterized in that: The functional layer comprises an aromatic amine-containing organic compound as described in any one of claims 1-7 or a mixture as described in claim 8.

Images