Fused ring organic compounds and their use in organic electronic devices

Abstract

The present application relates to a kind of fused ring organic compounds and its application in organic electronic device, belong to the technical field of organic solar cell.The present application provides a kind of fused ring organic compound can be used as photoactive layer acceptor material in organic solar cell device, can effectively improve its photoelectric conversion efficiency.

Description

Technical Field

[0001] This invention relates to the field of organic solar cell technology, and more particularly to a fused-ring organic compound and its application in organic electronic devices. Background Technology

[0002] The progress of human civilization has always been driven by energy, and solar energy has become the most watched green and clean energy source globally in recent years. Currently, commercially available solar cells are mainly made from inorganic raw materials such as crystalline silicon. Their raw material and cell manufacturing processes are complex, resulting in high production costs, high energy consumption, and severe environmental pollution, which significantly limits their application and development. Therefore, developing new solar energy technologies that are low-cost, environmentally friendly, and highly efficient has become one of the important topics in the new energy field. Organic solar cells, based on organic compounds, have the advantages of being lightweight, inexpensive, having controllable material design, and being able to be fabricated on a large scale with flexibility, thus possessing broader commercial application prospects.

[0003] The working principle of organic solar cells is as follows: 1) Under illumination, the photoactive layer material absorbs photons to generate excitons; 2) Excitons diffuse to the donor-acceptor interface; 3) Excitons dissociate into free electrons and holes at the donor-acceptor interface; 4) Free charge carriers (electrons and holes) transport in the donor and acceptor phases respectively; 5) Electrons and holes are transported to their respective electrodes to complete charge collection. The photoactive layer, as a crucial component of organic solar cells, is the key site for photoelectric conversion. Therefore, the development and matching of photoactive layer materials are essential to ensure the smooth and efficient completion of the photoelectric conversion process.

[0004] In recent years, thanks to innovations in active layer materials, particularly the development of ITIC, Y6-type non-fullerene acceptors and their derivatives, significant breakthroughs have been achieved in the photoelectric conversion efficiency (PCE) of organic solar cells. Current improvements based on Y-type fused-ring acceptors mainly focus on improving the fused-ring core and regulating side-chain groups. For example, Professor He Feng's group at Southern University of Science and Technology disclosed the acenaphthene-based fused-ring acceptor material ATIC-HD-4Cl, which, when paired with the donor material PBDB-T, achieved a PCE of 7.29% (DOI: 10.1021 / acs.macromol.2c00300). Chinese patent CN109134513A discloses a benzothiadiazole-based acceptor material, which, when paired with the donor material PBDB-TF, achieves a PCE exceeding 15% in organic solar cell devices. Chinese patent CN117143115A discloses a phenazine-based acceptor material, which, when paired with the donor material PM6, achieves a PCE of 16.85%.

[0005] Although existing technologies have laid a certain foundation for the research of Y-type fused-ring non-fullerene acceptor materials, in order to further improve the performance of organic solar cells and reduce their losses, it is still necessary to develop new non-fullerene acceptor material structures, which will play an important role in promoting the development of organic solar energy technology. Summary of the Invention

[0006] Therefore, the purpose of this invention is to provide a novel fused-ring organic compound. When the fused-ring organic compound designed and synthesized in this invention is used as a non-fullerene acceptor material in organic solar cell devices, it exhibits good photoelectric conversion efficiency.

[0007] The technical solution of the present invention is as follows:

[0008] A fused-ring organic compound having the structure shown in the following general formula:

[0009]

[0010] in:

[0011] Each time Z and W appear, they are independently selected from O, S, or Se;

[0012] X is selected from CR5 or N;

[0013] m is selected from 0, 1, 2, 3 or 4;

[0014] Each time R0 and R5 appear, they are independently selected from -H, -D (deuterium), straight-chain alkyl with 1-10 C atoms, or branched alkyl with 3-10 C atoms, -F, -Cl, -Br, -I, -CN or -CF3;

[0015] Each time M appears, it is independently selected from O or C(CN)2;

[0016] Ar1 and Ar2 are independently selected from unsubstituted or altered R1 and Ar2. v Aromatic groups having 6-10 carbon atoms are substituted, or the groups are unsubstituted or substituted with one or more R atoms. v Substituted heteroaromatic groups having 5-10 ring atoms;

[0017] R v Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight-chain alkyl group having 1-10 carbon atoms, or a branched alkyl group having 3-10 carbon atoms, a straight-chain alkoxy group having 1-10 carbon atoms, or a branched alkoxy group having 3-10 carbon atoms, a straight-chain alkylthio group having 1-10 carbon atoms, or a branched alkylthio group having 3-10 carbon atoms, or a group in combination of the above groups;

[0018] R1, R2, R3, and R4, each appearing independently, are selected from -H, -D, straight-chain alkyl groups having 1-30 carbon atoms, branched alkyl groups having 3-30 carbon atoms, straight-chain alkoxy groups having 1-30 carbon atoms, branched alkoxy groups having 3-30 carbon atoms, straight-chain alkylthio groups having 1-30 carbon atoms, branched alkylthio groups having 3-30 carbon atoms, and groups influenced by one or more R groups. * Substituted straight-chain alkyl groups having 1-30 carbon atoms, and substituted with one or more R atoms * Substituted branched alkyl groups having 3-30 carbon atoms, or with one or more R atoms * The substituted straight-chain alkoxy group having 1-30 C atoms is substituted by one or more R * Substituted branched alkoxy groups having 3-30 C atoms, and substituted with one or more R atoms * Substituted straight-chain alkylthio groups having 1-30 C atoms, and substituted with one or more R... * Substituted branched alkylthio groups having 3-30 C atoms, and substituted with one or more R groups # The substituted aromatic group having 6-10 carbon atoms, or the group being substituted with one or more R atoms. # Substituted heteroaromatic groups having 5-10 ring atoms;

[0019] R * Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, or -CN;

[0020] R # Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-20 carbon atoms, branched-chain alkyl with 3-20 carbon atoms, straight-chain alkoxy with 1-20 carbon atoms, branched-chain alkoxy with 3-20 carbon atoms, straight-chain alkylthio with 1-20 carbon atoms, branched-chain alkylthio with 3-20 carbon atoms, or a combination of the above groups.

[0021] Accordingly, the present invention also provides a photoactive layer acceptor material, wherein the photoactive layer acceptor material is selected from the above-mentioned fused-ring organic compounds.

[0022] Accordingly, the present invention also provides a mixture comprising the fused-ring 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.

[0023] Accordingly, the present invention also provides a composition comprising the fused-ring organic compound or mixture thereof as described above, and at least one organic solvent.

[0024] Accordingly, the present invention also provides an organic electronic device comprising a cathode, an anode, and at least one functional layer located between the cathode and the anode; the at least one functional layer comprising the above-mentioned fused-ring organic compound or the above-mentioned mixture or prepared from the above-mentioned composition.

[0025] Compared with the prior art, the present invention has at least the following beneficial effects:

[0026] This invention designs and synthesizes a novel non-fullerene acceptor material based on general formula (I), wherein a large fused ring core is fused with an N-containing acenaphthene ring. Because the nitrogen atom is in a conjugated system, it will change the molecular cloud arrangement of the core of the large fused ring, giving the core of the large fused ring an additional intramolecular hole transport channel, thereby enhancing intramolecular charge transfer.

[0027] At the same time, when When at least one nitrogen atom is present, the energy level of the compound can be lowered. A suitable energy level structure can improve the effective dissociation of excitons in the photoactive layer, thereby improving the photoelectric performance of the device.

[0028] In particular, when X is also selected from N, the molecular stacking and active layer morphology are further adjusted, so that the organic solar energy devices prepared with suitable donor materials exhibit excellent photoelectric conversion performance. Attached Figure Description

[0029] Figure 1 This is a schematic diagram of the structure of an organic solar cell in an embodiment of the present invention. Detailed Implementation

[0030] To make the objectives, technical solutions, and effects of this invention clearer and more explicit, the invention is further described in detail below. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the invention. All other embodiments obtained by those skilled in the art based on the described embodiments of the invention without creative effort are within the scope of protection of this invention.

[0031] The terms "and / or," "or / and," and "and / or" as used herein include any one of two or more of the related listed items, as well as any and all combinations of the related listed items. These arbitrary and all combinations include any two related listed items, any more related listed items, or a combination of all related listed items. It should be noted that when at least three items are connected using at least two conjunctions selected from "and / or," "or / and," and "and / or," it should be understood that in this invention, the technical solution undoubtedly includes solutions connected by "logical AND," and also undoubtedly includes solutions connected by "logical OR." For example, "A and / or B" includes three parallel solutions: A, B, and A+B. For example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, and D (that is, a technical solution that is connected by "logical OR"), as well as any and all combinations of A, B, C, and D, that is, combinations of any two or three of A, B, C, and D, and also combinations of all four of A, B, C, and D (that is, a technical solution that is connected by "logical AND").

[0032] In this invention, organic photovoltaic devices, organic solar cells, and OPV have the same meaning and can be used interchangeably.

[0033] In this invention, the active layer and the photoactive layer have the same meaning and can be used interchangeably.

[0034] In this invention, "substitution" means that one or more hydrogen atoms in the defined group are substituted by a substituent. For example, a phenyl group substituted with one R means that one hydrogen atom of the phenyl group is substituted by R.

[0035] In this invention, "ring atom number" refers to the number of atoms in the ring-forming atoms of a structural compound (e.g., monocyclic compound, fused-ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by atomic bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. In aromatic groups, the ring atom number is the same as the carbon atom number; in heteroaromatic groups, the ring atom number is the carbon atom number plus the heteroatom number; for example, the ring atom number of a benzene ring is 6, the ring atom number of a naphthalene ring is 10, the ring atom number of a quinoline ring is 10, the ring atom number of a thiophene group is 5, the ring atom number of a pyridine ring is 6, and the ring atom number of a thiophene is 8.

[0036] In this invention, "aromatic group" refers to any optional functional group or substituent derived from an aromatic carbon ring. The aromatic group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aromatic group can be a monocyclic aromatic group, a fused-ring aromatic group, two or more monocyclic aromatic groups conjugated by carbon-carbon bonds, a monocyclic aromatic group and a fused-ring aromatic group conjugated by carbon-carbon bonds, or two or more fused-ring aromatic groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as the aromatic group of this invention. Preferably, the "aromatic group" is selected from aromatic groups having 6-30 carbon atoms; further, it is selected from aromatic groups having 6-20 carbon atoms; further, it is selected from aromatic groups having 6-10 carbon atoms; the aromatic group includes, but is not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl, and their derivatives.

[0037] In this invention, a "heteroaromatic group" refers to a monovalent heteroaromatic ring or its derivative containing one, two, three, four, five, six or more heteroatoms. The heteroatoms can be at least one of B, O, N, P, Si, Se, and S. The heteroaromatic group can be a monocyclic heteroaryl or a polycyclic heteroaryl; in other words, it can be a single heteroaromatic ring system or a system of multiple heteroaromatic rings conjugated by carbon-carbon bonds, and any heteroaromatic ring system can be a single heteroaromatic monocyclic ring or a fused heteroaromatic ring. Preferably, the "heteroaromatic group" is selected from heteroaromatic groups having 5-30 ring atoms; further, it is selected from heteroaromatic groups having 5-20 ring atoms; and further, it is selected from heteroaromatic groups having 5-10 ring atoms. Heteroaromatic groups include, but are not limited to: thiophene, furanyl, pyrrole, diazolyl, triazolyl, imidazole, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, thiophene-thiophene, and their derivatives.

[0038] In this invention, the number of carbon atoms in the straight-chain alkyl group can be 1 to 20, 1 to 16, 1 to 10, or 1 to 6; non-limiting examples of straight-chain alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and -C. 10 H 21 -C 11 H 23 -C 12 H 25 -C 13 H 27 -C 14 H 29 -C 15 H 31 -C16 H 33 ;

[0039] In this invention, the number of carbon atoms in the branched alkyl group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6; non-limiting examples of branched alkyl groups include: isopropyl, branched alkyl groups containing 4 carbon atoms, branched alkyl groups containing 5 carbon atoms, branched alkyl groups containing 6 carbon atoms, branched alkyl groups containing 7 carbon atoms, branched alkyl groups containing 8 carbon atoms, branched alkyl groups containing 9 carbon atoms, branched alkyl groups containing 10 carbon atoms, branched alkyl groups containing 11 carbon atoms, branched alkyl groups containing 12 carbon atoms, branched alkyl groups containing 13 carbon atoms, branched alkyl groups containing 14 carbon atoms, branched alkyl groups containing 15 carbon atoms, and branched alkyl groups containing 16 carbon atoms.

[0040] The term "straight-chain alkoxy" refers to a group with the structure "-O-straight-chain alkyl", as defined above. The term "branched-chain alkoxy" represents "-O-branched alkyl", as defined above.

[0041] The term "straight-chain alkylthio" refers to a group with the structure "-S-straight-chain alkyl", as defined above. The term "branched-chain alkylthio" refers to "-S-branched alkyl", as defined above.

[0042] In this invention, multiple substituent substitution refers to a range including disubstitution, up to the maximum number of available substitutions. When a group mentioned in this invention is substituted by one or more substituents, it means that the substituent can be present at one or more available substitution positions on its linking group. When the substituent is present at multiple available substitution positions, the substituents can be of the same structure or different structures.

[0043] In this invention, the phrase "independently selected" means that when one or more groups appear simultaneously and in multiple places in the compound, they are all independently selected and can be the same or different.

[0044] The terms “combinations thereof,” “any combination thereof,” “any combination thereof,” “combination,” etc., used in this invention include all suitable combinations of any two, three, four, or more groups listed.

[0045] In this invention, terms such as "further," "even more," and "particularly" are used for descriptive purposes and to indicate differences in content, but should not be construed as limiting the scope of protection of this invention.

[0046] In this invention, "optionally," "optionally," and "optional" mean that they are optional, that is, they are selected from either "with" or "without." If multiple "options" appear in a technical solution, unless otherwise specified and there are no contradictions or mutual constraints, each "option" is independent.

[0047] In describing the structural elements of the present invention, the terms "comprising" or "including" or similar terms used in the present invention mean that the device or material preceding the word covers the device or material listed after the word and its equivalents, but does not exclude other devices or materials.

[0048] In this invention, the technical features described in an open-ended manner include both closed-ended technical solutions composed of the listed features and open-ended technical solutions that include the listed features.

[0049] The first aspect of the present invention provides an organic compound having a structure as shown in general formula (I):

[0050]

[0051] in:

[0052] Each time Z and W appear, they are independently selected from O, S, or Se;

[0053] X is selected from CR5 or N;

[0054] m is selected from 0, 1, 2, 3 or 4;

[0055] Each time R0 and R5 appear, they are independently selected from -H, -D (deuterium), straight-chain alkyl with 1-10 C atoms, or branched alkyl with 3-10 C atoms, -F, -Cl, -Br, -I, -CN or -CF3;

[0056] Each time M appears, it is independently selected from O or C(CN)2;

[0057] Ar1 and Ar2 are independently selected from unsubstituted or altered R1 and Ar2. v Aromatic groups having 6-10 carbon atoms are substituted, or the groups are unsubstituted or substituted with one or more R atoms. v Substituted heteroaromatic groups having 5-10 ring atoms;

[0058] R vEach occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight-chain alkyl group having 1-10 carbon atoms, or a branched alkyl group having 3-10 carbon atoms, a straight-chain alkoxy group having 1-10 carbon atoms, or a branched alkoxy group having 3-10 carbon atoms, a straight-chain alkylthio group having 1-10 carbon atoms, or a branched alkylthio group having 3-10 carbon atoms, or a group in combination of the above groups;

[0059] R1, R2, R3, and R4, each appearing independently, are selected from -H, -D, straight-chain alkyl groups having 1-30 carbon atoms, branched alkyl groups having 3-30 carbon atoms, straight-chain alkoxy groups having 1-30 carbon atoms, branched alkoxy groups having 3-30 carbon atoms, straight-chain alkylthio groups having 1-30 carbon atoms, branched alkylthio groups having 3-30 carbon atoms, and groups influenced by one or more R groups. * Substituted straight-chain alkyl groups having 1-30 carbon atoms, and substituted with one or more R atoms * Substituted branched alkyl groups having 3-30 carbon atoms, or with one or more R atoms * The substituted straight-chain alkoxy group having 1-30 C atoms is substituted by one or more R * Substituted branched alkoxy groups having 3-30 C atoms, and substituted with one or more R atoms * Substituted straight-chain alkylthio groups having 1-30 C atoms, and substituted with one or more R... * Substituted branched alkylthio groups having 3-30 C atoms, and substituted with one or more R groups # The substituted aromatic group having 6-10 carbon atoms, or the group being substituted with one or more R atoms. # Substituted heteroaromatic groups having 5-10 ring atoms;

[0060] R * Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, or -CN;

[0061] R # Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-20 carbon atoms, branched-chain alkyl with 3-20 carbon atoms, straight-chain alkoxy with 1-20 carbon atoms, branched-chain alkoxy with 3-20 carbon atoms, straight-chain alkylthio with 1-20 carbon atoms, branched-chain alkylthio with 3-20 carbon atoms, or a combination of the above groups.

[0062] In one embodiment, the R #Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-16 carbon atoms, branched-chain alkyl with 3-16 carbon atoms, straight-chain alkoxy with 1-16 carbon atoms, branched-chain alkoxy with 3-16 carbon atoms, straight-chain alkylthio with 1-16 carbon atoms, branched-chain alkylthio with 3-16 carbon atoms, or a combination of the above groups.

[0063] In one embodiment, the R # Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-12 carbon atoms, branched-chain alkyl with 3-12 carbon atoms, straight-chain alkoxy with 1-12 carbon atoms, branched-chain alkoxy with 3-12 carbon atoms, straight-chain alkylthio with 1-12 carbon atoms, branched-chain alkylthio with 3-12 carbon atoms, or a combination of the above groups.

[0064] In one embodiment, the fused-ring organic compound according to the present invention has a structure as shown in general formula (II-1) or general formula (II-2):

[0065]

[0066] In one embodiment, each occurrence of R5 is independently selected from -H, -D (deuterium), straight-chain alkyl with 1-6 C atoms, or branched alkyl with 3-6 C atoms, -F, -Cl, -Br, -I, -CN, or -CF3.

[0067] In one specific embodiment, each occurrence of R5 is independently selected from -H, -D (deuterium), methyl, -F, -Cl, -Br, -I, -CN, or -CF3.

[0068] In one embodiment, each occurrence of R0 is independently selected from -H, -D (deuterium), a straight-chain alkyl group having 1-6 carbon atoms, or a branched alkyl group having 3-6 carbon atoms, -F, -Cl, -Br, -I, -CN, or -CF3.

[0069] In one embodiment, R1, R2, R3, and R4, each appearing independently, are selected from -H, -D, straight-chain alkyl groups having 1-20 carbon atoms, branched alkyl groups having 3-20 carbon atoms, straight-chain alkoxy groups having 1-20 carbon atoms, branched alkoxy groups having 3-20 carbon atoms, straight-chain alkylthio groups having 1-20 carbon atoms, branched alkylthio groups having 3-20 carbon atoms, and groups influenced by one or more R groups. * Substituted straight-chain alkyl groups having 1-20 carbon atoms, and substituted with one or more R atoms * Substituted branched alkyl groups having 3-20 carbon atoms, or with one or more R atoms *The substituted straight-chain alkoxy group having 1-20 C atoms is substituted by one or more R * Substituted branched alkoxy groups having 3-20 C atoms, and substituted with one or more R atoms * Substituted straight-chain alkylthio groups having 1-20 C atoms, and substituted with one or more R * Substituted branched alkylthio groups having 3-20 C atoms, and substituted with one or more R # The substituted aromatic group having 6-10 carbon atoms, or the group being substituted with one or more R atoms. # Substituted heteroaromatic groups having 5-10 ring atoms.

[0070] In one embodiment, each occurrence of R1 and R2 is independently selected from -H, -D, straight-chain alkyl groups having 1-16 carbon atoms, branched alkyl groups having 3-16 carbon atoms, straight-chain alkoxy groups having 1-16 carbon atoms, branched alkoxy groups having 3-16 carbon atoms, straight-chain alkylthio groups having 1-16 carbon atoms, branched alkylthio groups having 3-16 carbon atoms, and groups influenced by one or more R groups. # Substituted phenyl, or substituted with one or more R # Substituted thiophene group.

[0071] In one embodiment, R1 and R2 are selected from the same group.

[0072] In one specific embodiment, each occurrence of R1 and R2 is independently selected from the following groups:

[0073]

[0074] In one embodiment, each occurrence of R3 and R4 is independently selected from -H, -D, straight-chain alkyl groups having 1-16 carbon atoms, branched alkyl groups having 3-16 carbon atoms, straight-chain alkoxy groups having 1-16 carbon atoms, branched alkoxy groups having 3-16 carbon atoms, straight-chain alkylthio groups having 1-16 carbon atoms, branched alkylthio groups having 3-16 carbon atoms, and groups influenced by one or more R groups. # Substituted phenyl, or substituted with one or more R # Substituted thiophene group.

[0075] Furthermore, each occurrence of R3 and R4 is independently selected from -H, -D, straight-chain alkyl groups having 1-12 carbon atoms, branched-chain alkyl groups having 3-12 carbon atoms, straight-chain alkoxy groups having 1-12 carbon atoms, branched-chain alkoxy groups having 3-12 carbon atoms, straight-chain alkylthio groups having 1-12 carbon atoms, branched-chain alkylthio groups having 3-12 carbon atoms, and groups influenced by one or more R groups. # Substituted phenyl, or substituted with one or more R # Substituted thiophene group.

[0076] In one embodiment, R3 and R4 are selected from the same group.

[0077] In one specific embodiment, each occurrence of R3 and R4 is independently selected from the following groups:

[0078]

[0079] In one embodiment, the fused-ring organic compound according to the present invention has a structure as described in general formula (III):

[0080]

[0081] Among them, R6 and R7 are each independently selected from straight-chain alkyl groups having 1-20 C atoms or branched alkyl groups having 3-20 C atoms.

[0082] It should be noted that when the fused-ring organic compound is selected from formula (III), the addition of the electron-donating alkoxy group will cause a blue shift in the absorption spectrum of the compound, making it more compatible with the indoor spectrum and exhibiting better device performance under indoor light irradiation.

[0083] In one embodiment, according to the fused-ring organic compound described above, the Ar1 and Ar2 are selected from the following groups:

[0084]

[0085] in:

[0086] * indicates a fusion site, which is selected from C atoms;

[0087] m is selected from 0, 1, 2, 3, 4, 5 or 6;

[0088] n is selected from 0, 1, 2, 3 or 4;

[0089] q is selected from 0, 1 or 2.

[0090] In a preferred embodiment, the R v Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-4 carbon atoms, branched alkyl with 3-4 carbon atoms, straight-chain alkoxy with 1-4 carbon atoms, branched alkoxy with 3-4 carbon atoms, straight-chain alkylthio with 1-4 carbon atoms, branched alkylthio with 3-4 carbon atoms, or a combination of the above groups;

[0091] In one embodiment, the Selected from

[0092] In one embodiment, the Selected from

[0093] In one embodiment, the and / or Selected from the following structure:

[0094]

[0095] Where: # represents the connection site.

[0096] In one specific embodiment, the and / or Selected from the following structure:

[0097]

[0098]

[0099] In one embodiment, the fused-ring organic compound according to the present invention, wherein the fused-ring organic compound of general formula (III) has the structure as described in general formulas (IV-1)-(IV-3):

[0100]

[0101] In general formula (IV-1), R8 is selected independently each time it appears, from -H, -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-10 carbon atoms, branched alkyl with 3-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, branched alkoxy with 3-10 carbon atoms, straight-chain alkylthio with 1-10 carbon atoms, or branched alkylthio with 3-10 carbon atoms, or a combination of the above groups.

[0102] In general formula (IV-2), each occurrence of R9 is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-10 carbon atoms, branched alkyl with 3-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, branched alkoxy with 3-10 carbon atoms, straight-chain alkylthio with 1-10 carbon atoms, or branched alkylthio with 3-10 carbon atoms, or a combination of the above groups.

[0103] In general formula (IV-3) R 10Each occurrence is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-10 carbon atoms, branched-chain alkyl with 3-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, branched-chain alkoxy with 3-10 carbon atoms, straight-chain alkylthio with 1-10 carbon atoms, or branched-chain alkylthio with 3-10 carbon atoms, or a combination of the above groups.

[0104] Preferably, R8, R9, R 10 Each occurrence is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-4 carbon atoms, branched alkyl with 3-4 carbon atoms, straight-chain alkoxy with 1-4 carbon atoms, branched alkoxy with 3-4 carbon atoms, straight-chain alkylthio with 1-4 carbon atoms, or branched alkylthio with 3-4 carbon atoms, or a combination of the above groups.

[0105] In one specific embodiment, the fused-ring organic compound according to the present invention is selected from, but not limited to, the following structures:

[0106]

[0107]

[0108]

[0109]

[0110] A second aspect of the present invention provides a photoactive layer acceptor material, said photoactive layer acceptor material being selected from fused-ring organic compounds as described in the first aspect.

[0111] A third aspect of the present invention provides a mixture comprising a fused-ring organic compound as described in the first aspect and at least one other organic functional material; preferably, the other organic functional material is selected as a photoactive layer donor material or a photoactive layer acceptor material.

[0112] In one embodiment, the other organic functional material is selected from photoactive layer donor materials; further, the photoactive layer donor material is selected from polymers or small molecule organic materials.

[0113] Furthermore, the photoactive layer donor material is selected from polymers; further, the polymer is 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 benzothiadiazoles (BT, BBT), quinoxalines (QU, PQ), pyrazines (TP, PQ) and electron-rich groups (such as thiophene derivatives) copolymerized, such as PCDTBT, PCPDTBT, PFO-DBT, PTB7, PM6, PM7, PTQ10, J52, etc.

[0114] In one specific embodiment, the polymer material is preferably selected from one or more of PBDB-T, PM6, PM7, D18, D18-Cl, PTO2, PB2, PB2F, PTVT-BT, PBQx-TCl, PTQ10, PTQ11, and PQM-Cl, but is not limited thereto.

[0115]

[0116] Where n is the number of repeating units and is an integer greater than 1.

[0117] In one embodiment, the other organic functional material is selected from photoactive layer acceptor materials; preferably, the photoactive layer acceptor material is selected from fullerene acceptor materials or non-fullerene acceptor materials. The non-fullerene acceptor material can be selected from commonly used materials in the art, such as Y6, L8-BO, BTP-H2, N3, BTP-eC9, etc., but is not limited thereto.

[0118] A fourth aspect of the present invention provides a composition comprising a fused-ring organic compound as described in the first aspect or a mixture as described in the third aspect, and at least one organic solvent.

[0119] In one embodiment, the organic solvent is selected from dichloromethane, trichloromethane, chlorobenzene, chloroform, 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, tetrahydronaphthalene, 2-methylthiophene, 3-methylthiophene, decahydronaphthalene, indane, methyl benzoate, ethyl benzoate, mesitylene, or a mixture of the above solvents.

[0120] In a preferred embodiment, the organic solvent is selected from chlorobenzene, toluene, o-xylene, or chloroform, but is not limited thereto.

[0121] In one embodiment, the concentration of the mixture in the organic solvent according to the present invention is selected from 5-30 mg / mL; further, the concentration of the mixture in the organic solvent is selected from 8-20 mg / mL.

[0122] It should be noted that the organic solvent can be evaporated from the solvent system to form a thin film comprising the organic compound.

[0123] In one embodiment, the composition may further include additives for adjusting viscosity, film-forming properties, and adhesion. In a preferred embodiment, the additives are selected from, but are 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), and 1,3,5-tribromobenzene (TBB).

[0124] This invention also relates to the use of the composition as a 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.

[0125] A fifth aspect of the present invention also provides an organic electronic device comprising a cathode, an anode, and at least one functional layer located between the cathode and the anode, said at least one functional layer comprising a fused-ring organic compound as described in the first aspect, a mixture as described in the third aspect, or a composition as described in the fourth aspect. Preferably, the organic electronic device is selected from organic solar cells (OPV), organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), organic lasers, organic photodetectors (OPDs), etc.

[0126] In a preferred embodiment, the organic electronic device is selected from organic solar cells.

[0127] Furthermore, the organic solar cell comprises a cathode, an anode, and a photoactive layer located between the cathode and the anode, the photoactive layer comprising a fused-ring organic compound as described in the first aspect, a mixture as described in the third aspect, or a composition as described in the fourth aspect.

[0128] In one embodiment, the materials used to prepare the cathode and anode may 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 above metals; conductive nanomaterials, such as metal nanowires, nanoparticle pastes, graphene, carbon nanotubes, etc.; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; combinations of metals and oxides, such as ZnO:Al or SnO2:Sb, etc.; and conductive polymers, such as PEDOT:PSS, polypyrrole, and polyaniline, etc.; or materials with multilayer structures, such as LiF / Al, LiO2 / Al, LiF / Fe, MoO3 / Al, Al:Li, Al:BaF2, and Al:BaF2:Ba, etc., but are not limited thereto.

[0129] In one embodiment, the photoactive layer material comprises a photoactive layer donor material and a photoactive layer acceptor material; the photoactive layer acceptor material comprises a fused-ring compound as described in the first aspect; further, the photoactive layer acceptor material may further comprise other non-fullerene acceptor materials or fullerene acceptor materials, such as Y6, L8-BO, BTP-H2, N3, BTP-eC9, etc., but is not limited thereto.

[0130] The photoactive layer donor material is described as above. Specifically, the photoactive layer donor material is preferably selected from one or more of PBDB-T, PM6, PM7, D18, D18-Cl, PTO2, PB2, PB2F, PTVT-BT, PBQx-TCl, PTQ10, PTQ11, and PQM-Cl, but is not limited thereto.

[0131] In one embodiment, the mass ratio of the photoactive layer donor material to the photoactive layer acceptor material is 1:1 to 1:1.8; preferably, the mass ratio of the photoactive layer donor material to the photoactive layer acceptor material is 1:1.1 to 1:1.5; preferably, the mass ratio of the photoactive layer donor material to the photoactive layer acceptor material is 1:1.1 to 1:1.2.

[0132] The photoactive layer can be formed by dissolving the photoactive material 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.

[0133] In one embodiment, the organic solar cell according to the present invention further includes a cathode buffer layer located between the cathode and the photoactive layer.

[0134] In a preferred embodiment, the cathode buffer layer material is selected from metal oxides or polymers. The metal oxide may be a metal complex containing 8-hydroxyquinoline, a complex containing Alq3, a metal complex containing Liq, LiF, Ca, or titanium oxide (TiO2). x The polymers can be PFN-Br, PFN, PDINN, PDINO, PNDIT-F3N-Br, or PNDIT-F3N, but are not limited to these.

[0135] In one embodiment, the organic electronic device according to the present invention further includes an anode buffer layer located between the anode and the photoactive layer.

[0136] In a preferred embodiment, the anode buffer layer material is selected from PEDOT:PSS, molybdenum oxide (MoO) x Preferably, x is selected from 2 or 3), vanadium oxide (V₂O₅), nickel oxide (NiO₂). x ), tungsten oxide (WO x Preferably, x is selected from 2 or 3) or self-assembled materials, such as 2PACz, MeO-2PACz, etc., but not limited thereto.

[0137] It should be noted that, in order to improve the performance of organic solar cell devices, the functional layer may further include other functional layers, including but not limited to a charge blocking layer.

[0138] In one embodiment, the organic solar cell further includes a substrate. Specifically, the substrate may be disposed on one side of the anode and on a different side from the photoactive layer.

[0139] In another embodiment, the organic solar cell further includes a substrate. Specifically, the substrate may be disposed on one side of the cathode and on a different side from the photoactive layer.

[0140] Specifically, the substrate can be a substrate with excellent transparency, surface smoothness, ease of handling, and water resistance. For example, 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.

[0141] The organic solar cell device according to the present invention can be applied to wearable devices, smart IoT, smart homes, smart agriculture, building photovoltaics, vehicle photovoltaics and other fields.

[0142] In the description of this invention, it should be understood that the terms "upper," "lower," "between layers," etc., indicate the orientation or positional relationship based on the orientation or positional relationship shown in the drawings, or the orientation or positional relationship commonly used when organic solar cell devices are in use, or the orientation or positional relationship commonly understood by those skilled in the art. They are only used to facilitate the description of this invention and to simplify the description, and are not intended to indicate or imply that the device or element referred to must have a specific orientation, or be constructed and operated in a specific orientation. Therefore, they should not be construed as limiting this invention. Specific Implementation

[0144] 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.

[0145] Examples of fused ring compounds and organic electronic devices according to the present invention are given herein, but the present invention is not limited to the following embodiments.

[0146] Synthesis Example 1: Synthesis of Compound (2)

[0147]

[0148] Synthesis of compounds 2-3:

[0149] Accurately weigh 3.06 g (20 mmol) of compound 4-ethynylquinoline and add it to a 100 mL high-pressure reactor. Purge with nitrogen three times, heat to 250°C, and react for 14 hours. Cool to room temperature, add dichloromethane and water to the reactor for extraction and separation. Extract the aqueous phase three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation to obtain a pale yellow solid. Purify by slurrying with petroleum ether, filter, and dry the filter cake to obtain 1.17 g of compound A, yield 38.4%. MS: 153.54.

[0150] Compound A (1.1 g, 7 mmol) and compound phenylselenoic anhydride (5.41 g, 15 mmol) were accurately weighed and added to a 100 mL three-necked flask. Then, 50 mL of chlorobenzene was added to the flask. The mixture was heated to 105°C and reacted for 4 hours until the reactants were completely reacted. After cooling to room temperature, excess phenylselenoic anhydride was quenched with an aqueous solution of saturated sodium sulfite. The mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and then subjected to vacuum distillation to remove excess solvent. The residue was subjected to column chromatography (eluting medium:PE:DCM = 15:1 (v / v)) to give approximately 1.05 g of compounds 2-3, yield: 82.0%. MS: 183.75.

[0151]

[0152] Synthesis of compound 2-2:

[0153] Accurately weigh LiAlH4 (195 mg, 2.5 mmol) and add it to a 100 mL three-necked flask. Then add 20 mL of anhydrous THF to the reaction flask. Under inert gas protection, add compound 2-1 (598 mg, 0.5 mmol) all at once, replace with nitrogen three times, and reflux for 1 h. After the starting materials have reacted completely, cool to room temperature and quench the reaction solution in 100 mL of water. Then extract with ethyl acetate three times, combine the organic phases, remove the solvent to obtain compound 2-2, which is used directly for the synthesis of compound 2-4 without purification.

[0154] Synthesis of compounds 2-4:

[0155] Compound 2-2 was dissolved in 30 mL of anhydrous toluene. Then, compound 2-3 (108 mg, 0.6 mmol) was added to the reaction flask. Nitrogen gas was purged three times, and the mixture was heated to 90°C and reacted for 1 hour until the reactants were completely reacted. The mixture was cooled to room temperature, and toluene was removed from the reaction solution by vacuum distillation. The solution was then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The residue was subjected to column chromatography (eluting with PE:EA = 20:1 (v / v)) to give 277 mg of compound 2-4. The combined yield of the two steps was 42.1%. MALDI-TOF-MS: 1315.65.

[0156] Synthesis of compounds 2-5:

[0157] Accurately weigh 277 mg (0.21 mmol) of compound 2-4 into a 100 mL three-necked flask, add approximately 30 mL of anhydrous DMF, purge with nitrogen three times, add 2 mL of phosphorus oxychloride, and then heat to 90 °C and react for 2 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, and remove excess solvent by vacuum distillation. The residue is subjected to column chromatography (eluting medium:PE:EA = 15:1 (v / v)) to give 246 mg of compound 2-5, yield: 85.5%. MALDI-TOF-MS: 1371.97.

[0158] Synthesis of compound (2):

[0159] Accurately weigh compound 2-5 (233 mg, 0.17 mmol) and compound 2-6 (99 mg, 0.43 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, replace with nitrogen three times, then add 2 mL of pyridine, heat to reflux for 4 h, and after the starting materials have completely reacted, cool the reaction to room temperature, add water and DCM for extraction and separation, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Purify the crude product by silica gel column chromatography, using DCM:PE = 1:5 (volume ratio) as the eluent, to obtain 206 mg of compound (2), with a yield of 67.5%. MALDI-TOF-MS: 1795.44.

[0160] Synthesis Example 2: Synthesis of Compound (6)

[0161]

[0162] Synthesis of compound 6-1:

[0163] Accurately weigh 4.64 g (20 mmol) of compound 5-ethynyl-8-bromoquinoline and add it to a 100 mL high-pressure reactor. Purge with nitrogen three times, heat to 250°C and react for 14 hours. Cool to room temperature, add dichloromethane and water to the reactor for extraction and separation. Extract the aqueous phase three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation to obtain a pale yellow solid. Purify by slurrying with petroleum ether, filter, and dry the filter cake to obtain 1.63 g of compound 6-1, yield 35.1%. MS: 232.87.

[0164] Synthesis of compound 6-2:

[0165] Accurately weigh 1.62 g (7 mmol) of compound 6-1 and 5.41 g (15 mmol) of compound phenylselenoside anhydride into a 100 mL three-necked flask. Then add 50 mL of chlorobenzene to the flask and heat to 105°C for 4 hours until the reactants are completely reacted. Cool to room temperature, quench excess phenylselenoside anhydride with a saturated sodium sulfite aqueous solution, extract three times with ethyl acetate, combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. The residue is subjected to column chromatography (eluting solvent:PE:DCM = 15:1 (v / v)) to give approximately 1.57 g of compound 6-2, yield: 85.7%. MS: 262.41

[0166] Synthesis of compound 6-3:

[0167] The freshly prepared compound 2-2 (2.34 g, 2 mmol) was dissolved in 30 mL of anhydrous toluene. Then, compound 6-2 (1.31 mg, 5 mmol) was added to the reaction flask. Nitrogen gas was purged three times, and the mixture was heated to 90°C and reacted for 1 hour until the reactants were completely reacted. The mixture was cooled to room temperature, and toluene was removed from the reaction solution by vacuum distillation. The solution was then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The residue was subjected to column chromatography (eluting medium:PE:EA = 15:1 (v / v)) to give 984 mg of compound 6-3, yield: 35.3%. MALDI-TOF-MS: 1394.45.

[0168] Synthesis of compound 6-4:

[0169] Compound 6-3 (976 mg, 0.7 mmol) was accurately weighed and added to a 100 mL three-necked flask. Approximately 30 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 2 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 residue was subjected to column chromatography (eluting medium:PE:EA = 15:1 (v / v)) to give 687 mg of compound 6-4, yield: 80.1%. MALDI-TOF-MS: 1450.78.

[0170] Synthesis of compound (6):

[0171] Accurately weigh compound 6-4 (728 mg, 0.5 mmol) and compound 2-6 (276 mg, 1.2 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, purge with nitrogen three times, then add 2 mL of pyridine, reflux for 4 h, cool to room temperature, quench with water, extract with DCM, purify the crude product by silica gel column chromatography, using DCM:PE = 1:1 (volume ratio) as eluent, to obtain 470 mg of compound (6), with a yield of 50.2%. MALDI-TOF-MS: 1874.71.

[0172] Synthesis Example 3: Synthesis of Compound (16)

[0173]

[0174] Synthesis of compound 16-1:

[0175] Accurately weigh 3.08 g (20 mmol) of compound 4-ethynyl-1,8-naphthidine into a 100 mL high-pressure reactor. Purge with nitrogen three times, heat to 200°C, and react for 14 hours. Cool to room temperature, add dichloromethane and water to the reactor for extraction and separation. Extract the aqueous phase three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation to obtain a pale yellow solid. Purify by slurrying with petroleum ether, filter, and dry the filter cake to obtain 1.24 g of compound 16-1, yield 40.1%. MS: 154.07.

[0176] Synthesis of compound 16-2:

[0177] Accurately weigh compound 16-1 (1.23 g, 8 mmol) and compound phenylselenoic anhydride (6.91 g, 19.2 mmol) into a 100 mL three-necked flask. Then add 50 mL of chlorobenzene to the flask and heat to 105°C for 4 hours until the reactants are completely reacted. Cool to room temperature, quench excess phenylselenoic anhydride with saturated sodium sulfite aqueous solution, extract three times with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. The residue is subjected to column chromatography (eluting solvent: PE:DCM = 10:1 (v / v)) to give compound 16-2 approximately 971.4 mg, yield: 75.4%. MS: 184.62.

[0178] Synthesis of compound 16-5:

[0179] Accurately weigh 195 mg (2.5 mmol) of LiAlH4 and add it to a 100 mL three-necked flask. Then add 20 mL of anhydrous THF to the reaction flask. Under inert gas protection, add compound 16-3 (486 mg, 0.5 mmol) all at once, purging with nitrogen three times. Heat to reflux for 1 h. After the starting materials have completely reacted, cool to room temperature and quench the reaction solution in 100 mL of water. Then extract with ethyl acetate three times, combine the organic phases, remove the solvent to obtain compound 16-4, which is used directly in the next synthesis without purification.

[0180] Compound 16-4 obtained in the previous step was dissolved in 30 mL of anhydrous toluene. Then, compound 16-2 (110 mg, 0.6 mmol) was added to the reaction flask. Nitrogen gas was purged three times, and the mixture was heated to 90°C and reacted for 1 hour until the starting material was completely reacted. The mixture was cooled to room temperature, and toluene was removed from the reaction solution by vacuum distillation. The solution was then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The residue was subjected to column chromatography (eluting medium:PE:EA = 20:1 (v / v)) to obtain 220 mg of compound 16-5. The combined yield of the two steps was 40.3%. MALDI-TOF-MS: 1091.81.

[0181] Synthesis of compound 16-6:

[0182] Accurately weigh 218 mg (0.2 mmol) of compound 16-5 into a 100 mL three-necked flask, add approximately 30 mL of anhydrous DMF, purge with nitrogen three times, then add 2 mL of phosphorus oxychloride and heat to 90 °C for 2 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, and remove excess solvent by vacuum distillation. The residue is subjected to column chromatography (eluting medium:PE:EA = 10:1 (v / v)) to give approximately 162 mg of compound 16-6, yield: 70.5%. MALDI-TOF-MS: 1147.94.

[0183] Synthesis of compound (16):

[0184] Accurately weigh compound 16-6 (160 mg, 0.14 mmol) and compound 16-7 (66 mg, 0.34 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, purge with nitrogen three times, then add 2 mL of pyridine, reflux for 4 h, cool to room temperature, quench with water, and extract with DCM. Purify the crude product by silica gel column chromatography, using DCM:PE = 2:1 (volume ratio) as the eluent, to obtain 121 mg of compound (16), with a yield of 57.5%. MALDI-TOF-MS: 1500.64.

[0185] Synthesis Example 4: Synthesis of Compound (17)

[0186]

[0187] Synthesis of compound 17-1:

[0188] The freshly prepared compound 2-2 (2.34 g, 2 mmol) was dissolved in 30 mL of anhydrous toluene. Then, compound 16-2 (920 mg, 5 mmol) was added to the reaction flask. Nitrogen gas was purged three times, and the mixture was heated to 90°C and reacted for 1 hour until the reactants were completely reacted. The mixture was cooled to room temperature, and toluene was removed from the reaction solution by vacuum distillation. The solution was then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The residue was subjected to column chromatography (eluting medium:PE:EA = 10:1 (v / v)) to give 779 mg of compound 17-1, yield: 28.4%. MALDI-TOF-MS: 1372.81.

[0189] Synthesis of compound (17):

[0190] Accurately weigh compound 17-1 (137 mg, 0.1 mmol) and compound 2-6 (55 mg, 0.24 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, replace with nitrogen three times, then add 1 mL of pyridine, heat to reflux for 4 h, cool the reaction to room temperature, quench with water and extract with DCM, purify the crude product with silica gel column, use DCM:PE = 3:1 (volume ratio) as eluent to obtain 82 mg of compound (17), with a yield of 54.6%. MALDI-TOF-MS: 1796.45.

[0191] Synthesis Example 5: Synthesis of Compound (23)

[0192]

[0193] Synthesis of compound 23-2:

[0194] Accurately weigh LiAlH4 (195.1 mg, 2.5 mmol) and add it to a 100 mL three-necked flask. Then add 20 mL of anhydrous THF to the reaction flask. Under inert gas protection, add compound 23-1 (500 mg, 0.5 mmol) all at once, purging with nitrogen three times. Heat to reflux for 1 h. After the starting materials have completely reacted, cool to room temperature and quench the reaction solution in 100 mL of water. Then extract with ethyl acetate three times, combine the organic phases, remove the solvent to obtain compound 23-2, which is used directly in the next synthesis without purification.

[0195] Synthesis of compound 23-3:

[0196] Compound 23-2 obtained in the previous step was dissolved in 30 mL of anhydrous toluene. Then, compound 16-2 (111 mg, 0.6 mmol) was added to the reaction flask. Nitrogen gas was purged three times, and the mixture was heated to 90°C and reacted for 1 hour until the starting material was completely reacted. After cooling to room temperature, toluene in the reaction solution was removed by vacuum distillation. The mixture was then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The residue was subjected to column chromatography (eluting agent:PE:EA = 20:1 (v / v)) to obtain 217 mg of compound 23-3. The combined yield of the two steps was 38.7%. MALDI-TOF-MS: 1120.03.

[0197] Synthesis of compound 23-4:

[0198] Compound 23-3 (217 mg, 0.19 mmol) was accurately weighed and added to a 100 mL three-necked flask. Approximately 30 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 2 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 residue was subjected to column chromatography (eluting medium:PE:EA = 15:1 (v / v)) to give 184 mg of compound 23-4, yield: 82.4%. MALDI-TOF-MS: 1176.47

[0199] Synthesis of compound (23):

[0200] Accurately weigh compound 23-4 (117 mg, 0.1 mmol) and compound 23-5 (63 mg, 0.24 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, replace with nitrogen three times, then add 2 mL of pyridine, heat to reflux for 4 h, cool the reaction to room temperature, quench with water and extract with DCM, purify the crude product with silica gel column, use DCM:PE = 2:1 (volume ratio) as eluent to obtain 108 mg of compound (23), with a yield of 64.7%. MALDI-TOF-MS: 1665.97.

[0201] Synthesis Example 6: Synthesis of Compound (32)

[0202]

[0203] Accurately weigh compound 16-5 (114.7 mg, 0.1 mmol) and compound 32-1 (56.3 mg, 0.24 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, replace with nitrogen three times, then add 1 mL of pyridine, heat to reflux for 4 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 = 5:1 (volume ratio) as eluent, to obtain a total of 105.1 mg of compound (32), with a yield of 66.5%. MALDI-TOF-MS: 1581.88.

[0204] Synthesis Example 7: Synthesis of Compound (33):

[0205]

[0206] Synthesis of compound 33-2:

[0207] Accurately weigh LiAlH4 (91.2 mg, 2.4 mmol) and add it to a 100 mL three-necked flask. Then add 20 mL of anhydrous THF to the reaction flask. Under inert gas protection, add compound 33-1 (617 mg, 0.6 mmol) all at once, purging with nitrogen three times. Heat to reflux for 1 h. After the starting materials have completely reacted, cool to room temperature and quench the reaction solution in 100 mL of water. Then extract with ethyl acetate three times, combine the organic phases, remove the solvent to obtain compound 33-2, which is used directly in the next synthesis without purification.

[0208] Synthesis of compound 33-3:

[0209] Compound 33-2 obtained in the previous step was dissolved in 30 mL of anhydrous toluene. Then, 16-2 (129 mg, 0.7 mmol) was added to the reaction flask, nitrogen was purged three times, and the mixture was heated to 90°C and reacted for 1 hour until the starting material was completely reacted. After cooling to room temperature, the reaction solution was quenched in 100 mL of water, and then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The residue was subjected to column chromatography (eluting agent:PE:EA = 15:1 (v / v)) to give 255 mg of compound 33-3, yield: 37.1%. MS: 1147.72.

[0210] Synthesis of compound 33-4:

[0211] Accurately weigh 229 mg (0.20 mmol) of compound 33-3 into a 100 mL three-necked flask, add approximately 30 mL of anhydrous DMF, purge with nitrogen three times, add 2 mL of phosphorus oxychloride, and then heat to 90 °C and react for 2 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, and remove excess solvent by vacuum distillation. The residue is subjected to column chromatography (eluting medium:PE:EA = 10:1 (v / v)) to give 169 mg of compound 33-4, yield: 70.4%. MALDI-TOF-MS: 1204.44.

[0212] Synthesis of compound (33):

[0213] Accurately weigh compound 33-4 (168 mg, 0.14 mmol) and compound 2-6 (80.5 mg, 0.35 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, replace with nitrogen three times, then add 1 mL of pyridine, heat to reflux for 4 h, cool the reaction to room temperature, quench with water and extract with DCM, purify the crude product with silica gel column, use DCM:PE = 1:1 (volume ratio) as eluent to obtain 163 mg of compound (33), with a yield of 71.3%. MALDI-TOF-MS: 1628.49.

[0214] Synthesis Example 8: Synthesis of Compound (34)

[0215]

[0216] Synthesis of compound 34-2:

[0217] Accurately weigh LiAlH4 (91.2 mg, 2.4 mmol) and add it to a 100 mL three-necked flask. Then add 20 mL of anhydrous THF to the reaction flask. Under inert gas protection, add compound 34-1 (698 mg, 0.6 mmol) all at once, purging with nitrogen three times. Heat to reflux for 1 h. After the starting materials have completely reacted, cool to room temperature and quench the reaction solution in 100 mL of water. Then extract three times with ethyl acetate, combine the organic phases, remove the solvent to obtain compound 34-2, which is used directly in the next synthesis without purification.

[0218] Synthesis of compound 34-3:

[0219] Compound 34-2 obtained in the previous step was dissolved in 30 mL of anhydrous toluene. Then, 16-2 (129 mg, 0.7 mmol) was added to the reaction flask, nitrogen was purged three times, and the mixture was heated to 90°C and reacted for 1 hour until the starting material was completely reacted. After cooling to room temperature, the reaction solution was quenched in 100 mL of water, and then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The residue was subjected to column chromatography (eluting agent:PE:EA = 10:1 (v / v)) to give 273 mg of compound 34-3, yield: 35.5%. MS: 1284.78.

[0220] Synthesis of compound 34-4:

[0221] Compound 34-3 (270 mg, 0.21 mmol) was accurately weighed and added to a 100 mL three-necked flask. Approximately 30 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 2 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 residue was subjected to column chromatography (eluting medium:PE:EA = 15:1 (v / v)) to give approximately 206 mg of compound 34-4, yield: 73.4%. MALDI-TOF-MS: 1340.21.

[0222] Synthesis of compound (34):

[0223] Accurately weigh compound 34-4 (201 mg, 0.15 mmol) and compound 2-6 (83 mg, 0.36 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, replace with nitrogen three times, then add 1 mL of pyridine, heat to reflux for 4 h, cool the reaction to room temperature, quench with water and extract with DCM, purify the crude product with silica gel column, use DCM:PE = 4:1 (volume ratio) as eluent to obtain 145 mg of compound (34), with a yield of 54.9%. MALDI-TOF-MS: 1764.47.

[0224] Synthesis Example 9: Synthesis of Compound (37)

[0225]

[0226] Synthesis of compound 37-2:

[0227] Accurately weigh LiAlH4 (91.2 mg, 2.4 mmol) and add it to a 100 mL three-necked flask. Then add 20 mL of anhydrous THF to the reaction flask. Under inert gas protection, add compound 37-1 (639.2 mg, 0.6 mmol) all at once, purging with nitrogen three times. Heat to reflux for 1 h. After the starting material has completely reacted, cool to room temperature and quench the reaction solution in 100 mL of water. Then extract three times with ethyl acetate, combine the organic phases, remove the solvent to obtain compound 37-2, which is used directly in the next synthesis without purification.

[0228] Synthesis of compound 37-3:

[0229] Compound 37-2 obtained in the previous step was dissolved in 30 mL of anhydrous toluene. Then, 16-2 (129 mg, 0.7 mmol) was added to the reaction flask, nitrogen was purged three times, and the mixture was heated to 90°C and reacted for 1 hour until the starting material was completely reacted. The mixture was cooled to room temperature, and the reaction solution was quenched in 100 mL of water. The mixture was then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The residue was subjected to column chromatography (eluting agent: PE:EA = 20:1) to give 285 mg of compound 37-3, yield: 40.1%. MS: 1186.01.

[0230] Synthesis of compound 37-4:

[0231] Compound 37-3 (285 mg, 0.24 mmol) was accurately weighed and added to a 100 mL three-necked flask. Approximately 30 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 2 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 residue was subjected to column chromatography (eluting medium:PE:EA = 10:1 (v / v)) to give approximately 228 mg of compound 37-4, yield: 76.5%. MALDI-TOF-MS: 1242.23.

[0232] Synthesis of compound (37):

[0233] Accurately weigh compound 37-4 (223 mg, 0.18 mmol) and compound 23-5 (113 mg, 0.43 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, replace with nitrogen three times, then add 1 mL of pyridine, heat to reflux for 4 h, cool the reaction to room temperature, quench with water and extract with DCM, purify the crude product with silica gel column, use DCM:PE = 4:1 (volume ratio) as eluent to obtain 174 mg of compound (37), with a yield of 55.9%. MALDI-TOF-MS: 1731.43.

[0234] Synthesis Example 10: Synthesis of Compound (50)

[0235]

[0236] Synthesis of compound 50-2:

[0237] Accurately weigh LiAlH4 (91.2 mg, 2.4 mmol) and add it to a 100 mL three-necked flask. Then add 20 mL of anhydrous THF to the reaction flask. Under inert gas protection, add compound 50-1 (686 mg, 0.6 mmol) all at once, purging with nitrogen three times. Heat to reflux for 1 h. After the starting materials have completely reacted, cool to room temperature and quench the reaction solution in 100 mL of water. Then extract with ethyl acetate three times, combine the organic phases, remove the solvent to obtain compound 50-2, which is used directly in the next synthesis without purification.

[0238] Synthesis of compound 50-3:

[0239] Compound 50-2 obtained in the previous step was dissolved in 30 mL of anhydrous toluene. Then, 16-2 (129 mg, 0.7 mmol) was added to the reaction flask, nitrogen was purged three times, and the mixture was heated to 90°C and reacted for 1 hour until the starting material was completely reacted. After cooling to room temperature, the reaction solution was quenched in 100 mL of water, and then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The residue was subjected to column chromatography (eluting agent:PE:EA = 10:1 (v / v)) to give 284 mg of compound 50-3, yield: 37.5%. MS: 1264.15.

[0240] Synthesis of compound 50-4:

[0241] Compound 50-3 (284 mg, 0.22 mmol) was accurately weighed and added to a 100 mL three-necked flask. Approximately 30 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 2 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 residue was subjected to column chromatography (eluting medium:PE:EA = 15:1 (v / v)) to give approximately 201 mg of compound 50-4, yield: 69.3%. MALDI-TOF-MS: 1320.53.

[0242] Synthesis of compound (50):

[0243] Accurately weigh compound 50-4 (198 mg, 0.15 mmol) and compound 2-6 (83 mg, 0.36 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, replace with nitrogen three times, then add 1 mL of pyridine, heat to reflux for 4 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 = 4:1 (volume ratio) as eluent, to obtain a total of 152 mg of compound (50), with a yield of 58.2%. MALDI-TOF-MS: 1744.65.

[0244] Synthesis Example 11: Synthesis of compound (51):

[0245]

[0246] Accurately weigh compound 50-4 (132 mg, 0.1 mmol) and compound 51-1 (50 mg, 0.24 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, replace with nitrogen three times, then add 1 mL of pyridine, heat to reflux for 4 h, cool the reaction to room temperature, quench with water and extract with DCM, purify the crude product with silica gel column, use DCM:PE = 1:3 (volume ratio) as eluent to obtain 108 mg of compound (51), with a yield of 63.4%. MALDI-TOF-MS: 1700.46.

[0247] Synthesis Example 12: Synthesis of Compound (56)

[0248]

[0249] Synthesis of compound 56-2:

[0250] Accurately weigh LiAlH4 (91.2 mg, 2.4 mmol) and add it to a 100 mL three-necked flask. Then add 20 mL of anhydrous THF to the reaction flask. Under inert gas protection, add compound 56-1 (670 mg, 0.6 mmol) all at once, purging with nitrogen three times. Heat to reflux for 1 h. After the starting materials have completely reacted, cool to room temperature and quench the reaction solution in 100 mL of water. Then extract with ethyl acetate three times, combine the organic phases, remove the solvent to obtain compound 56-2, which is used directly in the next synthesis without purification.

[0251] Synthesis of compound 56-3:

[0252] Compound 56-2 obtained in the previous step was dissolved in 30 mL of anhydrous toluene. Then, 16-2 (129 mg, 0.7 mmol) was added to the reaction flask, nitrogen was purged three times, and the mixture was heated to 90°C and reacted for 1 hour until the starting material was completely reacted. After cooling to room temperature, the reaction solution was quenched in 100 mL of water, and then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and excess solvent was removed by vacuum distillation. The residue was subjected to column chromatography (eluting with PE:EA = 15:1) to give 300 mg of compound 56-3, with a yield of 40.5%. MS: 1235.94.

[0253] Synthesis of compound 56-4:

[0254] Compound 56-3 (296 mg, 0.24 mmol) was accurately weighed and added to a 100 mL three-necked flask. Approximately 30 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 2 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 residue was subjected to column chromatography (eluting with PE:EA = 20:1) to give approximately 203 mg of compound 56-4, yield: 65.4%. MALDI-TOF-MS: 1292.02.

[0255] Synthesis of compound (56):

[0256] Accurately weigh compound 56-4 (194 mg, 0.15 mmol) and compound 56-5 (88 mg, 0.36 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, purge with nitrogen three times, then add 1 mL of pyridine, reflux for 4 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 a total of 126 mg of compound (56), with a yield of 48.2%. MALDI-TOF-MS: 1744.58.

[0257] Synthesis Example 13: Synthesis of Compound (63)

[0258]

[0259] Accurately weigh compound 50-4 (185 mg, 0.14 mmol) and compound 32-1 (82 mg, 0.35 mmol) into a 50 mL three-necked flask, add 20 mL of chloroform, replace with nitrogen three times, then add 1 mL of pyridine, heat to reflux for 4 h, cool the reaction to room temperature, quench with water, extract with DCM, purify the crude product with silica gel column chromatography, use DCM:PE = 3:1 (volume ratio) as eluent to obtain 159 mg of compound (63), with a yield of 64.7%. MALDI-TOF-MS: 1753.61.

[0260] Fabrication and characterization of organic solar cell (OPV) devices

[0261] This embodiment illustrates the preparation and characterization of the OPV device in the organic electronic device provided by the present invention, but the present invention is not limited to the following embodiment.

[0262] like Figure 1 As shown, the OPV device structure is as follows: Indium Tin Oxide (ITO) / PEDOT:PSS / Active Layer / PDINO / Ag.

[0263] Device Example 1:

[0264] 1) ITO substrate cleaning:

[0265] 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.

[0266] 2) Preparation of the anode buffer layer

[0267] 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.

[0268] 3) Preparation of photoactive layer

[0269] In a glove box (inert gas atmosphere), the photoactive layer material (the concentration of the mixture of donor and acceptor materials in chloroform is 10 mg / mL) is 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 is selected from D18, and the acceptor material is selected from fused-ring organic compounds (2), with a mass ratio of donor to acceptor material of 1:1.5.

[0270]

[0271] 4) Preparation of cathode buffer layer

[0272] After annealing on a hot plate at 100°C for 10 min, the cathode buffer layer material PDINO (prepared by dissolving PDINO in methanol to a concentration of 1 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.

[0273] 5) Cathode layer preparation

[0274] Ag was deposited onto the cathode buffer layer in a high vacuum (1×10⁻⁶ mbar) to form a cathode layer with a thickness of 100 nm, at a deposition rate of 4 Å / s.

[0275] 6) Packaging

[0276] The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0277] Device Examples 2-7:

[0278] The preparation methods of Device Examples 2-7 are the same as those of Device Example 1, except that the fused-ring organic compound (2) in the photoactive layer of Device Example 1 is replaced with fused-ring organic compound (6), fused-ring organic compound (17), fused-ring organic compound (23), fused-ring organic compound (33), fused-ring organic compound (34), and fused-ring organic compound (37), respectively. The other steps are the same, and the prepared devices are referred to as Device Examples 2-7. For details of the acceptor materials of the specific device examples, please refer to Table 1.

[0279] Comparative examples of devices:

[0280] The fused-ring organic compound (2) of the acceptor material in the photoactive layer of the device embodiment was replaced with an organic compound (Ref), and the other steps and methods were the same. The device prepared was referred to as the device comparative embodiment.

[0281]

[0282] The synthetic route for the organic compound (Ref) is described in Aggregation of Small Molecule and Polymer Acceptors with 2D Fused Backbones in Organic Solar Cells, DOI: 10.1021 / acs.macromol.2c00300.

[0283] The prepared organic solar cell device was tested under sunlight. The cell current-voltage curve was tested and the photoelectric conversion efficiency was calculated under the standard light of AM 1.5G on a solar simulator (SS-F5-3A).

[0284] Table 1

[0285]

[0286]

[0287] As can be seen from the data in Table 1, when the fused-ring organic compound described in this invention is used as the acceptor material in organic solar cell devices, the photoelectric conversion efficiency is significantly improved compared to the device comparison example; especially when X is also selected from N, the device performance is even better, with a photoelectric conversion efficiency exceeding 16%.

[0288] Device Examples 8-13:

[0289] The preparation methods of Device Examples 8-13 are the same as those of Device Example 1, except that the fused-ring organic compound (2) in the photoactive layer of Device Example 1 is replaced with fused-ring organic compound (16), fused-ring organic compound (32), fused-ring organic compound (50), fused-ring organic compound (51), fused-ring organic compound (56), and fused-ring organic compound (63), respectively. The other steps are the same, and the prepared devices are referred to as Device Examples 8-13. For details of the acceptor materials of the specific device examples, please refer to Table 2.

[0290] The prepared organic solar cell device was tested under indoor light. The cell current-voltage curve was tested under a 2700K LED light source (1000 lux) simulator, and the photoelectric conversion efficiency was calculated.

[0291] Table 2

[0292] Photoactive layer acceptor materials Photoelectric conversion efficiency (%) Device Example 8 Fused-ring organic compounds (16) 20.81 Device Example 9 Fused-ring organic compounds (32) 22.94 Device Example 10 Fused-ring organic compounds (50) 25.68 Device Example 11 Fused-ring organic compounds (51) 23.20 Device Example 12 Fused-ring organic compounds (56) 23.73 Device Example 13 Fused-ring organic compounds (63) 24.47 Comparative Examples of Devices Organic compounds (Ref) 13.88

[0293] As shown in Table 2, the fused-ring organic compound described in this invention exhibits excellent photoelectric conversion efficiency under indoor light irradiation. It can be used as an indoor photovoltaic material in indoor scenarios such as smart IoT and smart homes.

[0294] 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. A fused-ring organic compound, characterized in that: It has a structure as shown in general formula (I): in: Each time Z and W appear, they are independently selected from O, S, or Se; X is selected from CR5 or N; Each time R0 and R5 appear, they are independently selected from -H, -D, straight-chain alkyl with 1-10 C atoms, or branched alkyl with 3-10 C atoms, -F, -Cl, -Br, -I, -CN or -CF3; m is selected from 0, 1, 2, 3 or 4; Each time M appears, it is independently selected from O or C(CN)2; Ar1 and Ar2 are independently selected from unsubstituted or altered R1 and Ar2. v Aromatic groups having 6-10 carbon atoms are substituted, or the groups are unsubstituted or substituted with one or more R atoms. v A substituted heteroaromatic group having 5-10 ring atoms; the heteroaromatic group comprising one or two heteroatoms selected from at least one of O, Se and S; R v Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight-chain alkyl group having 1-10 carbon atoms, or a branched-chain alkyl group having 3-10 carbon atoms, a straight-chain alkoxy group having 1-10 carbon atoms, or a branched-chain alkoxy group having 3-10 carbon atoms, a straight-chain alkylthio group having 1-10 carbon atoms, or a branched-chain alkylthio group having 3-10 carbon atoms; R1, R2, R3, and R4, each appearing independently, are selected from -H, -D, straight-chain alkyl groups having 1-30 carbon atoms, branched alkyl groups having 3-30 carbon atoms, straight-chain alkoxy groups having 1-30 carbon atoms, branched alkoxy groups having 3-30 carbon atoms, straight-chain alkylthio groups having 1-30 carbon atoms, branched alkylthio groups having 3-30 carbon atoms, and groups influenced by one or more R groups. * Substituted straight-chain alkyl groups having 1-30 carbon atoms, and substituted with one or more R atoms * Substituted branched alkyl groups having 3-30 carbon atoms, or with one or more R atoms * The substituted straight-chain alkoxy group having 1-30 C atoms is substituted by one or more R * Substituted branched alkoxy groups having 3-30 C atoms, and substituted with one or more R atoms * Substituted straight-chain alkylthio groups having 1-30 C atoms, and substituted with one or more R... * Substituted branched alkylthio groups having 3-30 carbon atoms; R * Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, or -CN.

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

3. The fused-ring organic compound according to claim 1 or 2, characterized in that: Each occurrence of R1, R2, R3, and R4 is independently selected from -H, -D, straight-chain alkyl with 1-16 carbon atoms, branched alkyl with 3-16 carbon atoms, straight-chain alkoxy with 1-16 carbon atoms, branched alkoxy with 3-16 carbon atoms, straight-chain alkylthio with 1-16 carbon atoms, or branched alkylthio with 3-16 carbon atoms.

4. The fused-ring organic compound according to claim 1, characterized in that: The fused-ring organic compound is selected from the structure shown in general formula (III): Each time R6 and R7 appear, they are independently selected from straight-chain alkyl groups having 1-20 C atoms or branched alkyl groups having 3-20 C atoms.

5. The fused-ring organic compound according to claim 2 or 4, characterized in that: The Ar1 and Ar2 are selected from the following groups: in: R v Each time it appears, it is independently selected from -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-4 carbon atoms, branched alkyl with 3-4 carbon atoms, straight-chain alkoxy with 1-4 carbon atoms, branched alkoxy with 3-4 carbon atoms, straight-chain alkylthio with 1-4 carbon atoms, and branched alkylthio with 3-4 carbon atoms; * indicates a fusion site, which is selected from C atoms; m is selected from 0, 1, 2, 3, 4, 5 or 6; n is selected from 0, 1, 2, 3 or 4; q is selected from 0, 1 or 2.

6. The fused-ring organic compound according to claim 4, characterized in that: The fused-ring organic compounds are selected from structures represented by general formulas (IV-1)-(IV-3): Among them, R8, R9, R 10 Each occurrence is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, straight-chain alkyl with 1-10 carbon atoms, branched-chain alkyl with 3-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, branched-chain alkoxy with 3-10 carbon atoms, straight-chain alkylthio with 1-10 carbon atoms, or branched-chain alkylthio with 3-10 carbon atoms.

7. The fused-ring organic compound according to claim 1, characterized in that: The fused-ring organic compound is selected from the following structural formulas:

8. A mixture, characterized in that: The mixture comprises a fused-ring organic compound as described in any one of claims 1-7, and at least one other organic functional material.

9. A composition, characterized in that: The composition comprises a fused-ring 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, the organic electronic device comprising a cathode, an anode, and at least one functional layer located between the cathode and the anode, characterized in that: The at least one functional layer comprises a fused-ring organic compound as described in any one of claims 1-7, a mixture as described in claim 8, or is prepared from a composition as described in claim 9.

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