compound

Abstract

Provided are a non-fullerene acceptor compound that improves photoinduced hole transfer to an electron donor and an organic photoreactive device. 【Solution means】The bulk heterojunction layer contains compounds of the following formulas (I) and (II). A 3 , 2 , 1 , , 3 , 1 , 1 , 1 , 1 , -(B 1 )x 1 -(D 1 )y 1 -(B 1 )x 2 -A 1 (I). A 1 -(B 2 )x 5 -(D 2 )y 2 -(B 3 )x 3 -A 2 -(B 3 )x 4 -(D 3 )y 3 -(B 2 )x 6 -A 1 (II). In the formula, A 1 is an electron-withdrawing group, and at least one A 1 is any group of the following formula. TIFF2026067815000064.tif58159 A 2 is a divalent heteroaromatic electron-withdrawing group, D 1 ~D 3 are electron-donating groups, and B 1 ~B 3 are crosslinking groups.

Description

Technical Field

[0001] Embodiments of the present disclosure relate to electron-accepting compounds, and more particularly, to compounds suitable for use as electron-accepting materials in photoreactive devices.

Background Art

[0002] An organic photodetector may include a photoactive layer of a blend of an electron-donating material and an electron-accepting material between an anode and a cathode. Known electron-accepting materials include fullerenes and non-fullerene acceptors (NFAs).

[0003] Chinese Patent Publication No. 116425768 discloses a compound of formula (I).

Chemical Formula

Chemical Formula

[0004] International Publication No. 2024 / 094804 discloses a compound containing an electron-accepting group of formula (III).

Chemical Formula

[0005] Tengfei Li et al, "Sensitive photodetection below silicon bandgap using quinoid-capped organic semiconductors," Science Advances, vol.9 issue 13, 2023, discloses quinoid-terminated compounds for near-infrared photodetectors.

[0006] Yi Zhang et al, "Sensitive SWIR Organic Photodetectors with Spectral Response Reaching 1.5μm", Advanced Materials, https: / / doi.org / 10.1002 / adma.202406950 discloses an organic photodetector containing NFA "Y-QC4F" having a difluorosubstituted quinoid terminal group (QC-2F). [Prior art documents] [Patent Documents]

[0007] [Patent Document 1] Chinese Patent Publication No. 116425768 [Patent Document 2] International Publication No. 2024 / 094804 [Non-patent literature]

[0008] [Non-Patent Document 1] Tengfei Li et al, “Sensitive photodetection below silicon bandgap using quinoid-capped organic semiconductors”, Science Advances, vol.9 issue 13,2023 [Non-Patent Document 2] Yi Zhang et al, “Sensitive SWIR Organic Photodetectors with Spectral Response Reaching 1.5μm”, Advanced Materials, https: / / doi.org / 10.1002 / adma.202406950 [Overview of the project] [Means for solving the problem]

[0009] The inventors have found that by providing non-fullerene acceptors (NFAs) having specific electron-accepting terminal groups with nitrogen-containing electron-withdrawing heteroaromatic groups, the HOMO of such NFAs can be made deeper compared to compounds without such heteroaromatic groups. This improves the compatibility between NFAs and electron donors having deep HOMOs, thereby improving photo-induced hole transfer from NFAs to electron donors.

[0010] The inventors have also found that such N-containing electron-withdrawing heteroaromatic groups can increase the absorption wavelength of such NFAs compared to compounds in which such heteroaromatic groups are absent.

[0011] Accordingly, in a first aspect, the present disclosure provides compounds of formula (I) or (II).

[0012] A 1 -( B 1 )x 1 -(D 1 )y 1 -( B 1 )x 2 -A1 (I) A 1 -( B 2 )x 5 -(D 2 )y 2 -( B 3 )x 3 -A 2 -( B 3 )x 4 -(D 3 )y 3 -( B 2 )x 6 -A 1 (II) During the ceremony, A 2 It is a divalent heteroaromatic electron-accepting group, D 1 , D 2 and D 3 In each instance, it is an electron-donating group, B 1 B 2 , and B 3 In each occurrence, it is an independent bridging group. x 1 -x 6 These are, independently, 0, 1, 2, or 3. y 1 , y 2 and y 3 Each of them is independently at least 1, Each A 1 is an electron-accepting group and has at least one A 1 is the base of equation (III), (IV), or (V). [Table 1] During the ceremony, Each R 1 These are independent substituents, R 2 is H or a substituent, Ar 1The compounds are selected from benzene, 1,2,3-triazole, 1,25-thiadiazole, 1,2,3-thiadiazole, and a 6-membered heteroaromatic group in which the ring atom is selected from C and N, and Ar 1 It is either unsubstituted or substituted with one or more substituents. --- is A 1 It represents the connection point, Z 1 -Z 6 In each occurrence, N and CR are independent. 4 Selected from, where R 4 In each occurrence, is H or a substituent. Ar 1 is benzene, and A 1 If is a base of equation (III), then Z 1 and Z 2 At least one of them is N, Ar 1 is benzene, and A 1 If is a base of equation (IV), then Z 3 and Z 4 At least one of them is N, Ar 1 is benzene, and A 1 If is the basis of equation (V), then Z 5 and Z 6 At least one of them is N.

[0013] Ar 1 Ar may be benzene. 1 If it is benzene, the following may also be true.

[0014] A 1 If is a base of equation (III), then Z 1 and Z 2 Each of these is N, A 1 If is a base of equation (IV), then Z 3 and Z 4 Each of these is N, A 1 If is the basis of equation (V), then Z 5 and Z 6 Each of these is N.

[0015] Ar 1 may be a 1,4-diazine, A 1 When is a group of formula (III), Z 1 and Z 2 are each CR 4 respectively, A 1 When is a group of formula (IV), Z 3 and Z 4 are each CR 4 respectively, A 1 When is a group of formula (V), Z 5 and Z 6 are each CR 4 respectively, At least one A 1 may be a group of formula (III).

[0016] Each A 1 may be a group of formula (III), (IV) or (V).

[0017] Each A 1 may be the same.

[0018] <C Each R 1 may be independently selected from CN, CF3 and COOR 40 where R 40 is, in each occurrence, H or a substituent.

[0019] Ar 1 may be substituted with at least one electron-withdrawing group. The at least one electron-withdrawing group may be selected from Br, Cl, F, CN, C 1-12 fluoroalkyl and COOR 15 where R 15 is a C 1-20 hydrocarbyl group.

[0020] Each R 4 may be independently selected from H or an electron-withdrawing group.

[0021] This disclosure provides compositions comprising an electron-donating material and an electron-accepting material, wherein the electron-accepting material is a compound described herein.

[0022] This disclosure provides an organic electronic device comprising an active layer containing a compound or composition described herein.

[0023] The organic electronic device may be an organic photoresponsive device comprising a bulk heterojunction layer disposed between the anode and the cathode, the bulk heterojunction layer comprising the composition described herein.

[0024] The organic photoresponsive device may also be an organic photodetector.

[0025] This disclosure provides a light sensor comprising a light source and an organic photodetector described herein, wherein the organic photodetector is configured to detect light emitted from the light source.

[0026] The light source may emit light having a peak wavelength greater than 900 nm.

[0027] This disclosure provides formulations comprising compounds or compositions described herein, dissolved or dispersed in one or more solvents.

[0028] This disclosure provides a method for forming an organic electronic device as described herein, wherein the formation of the active layer comprises depositing a formulation as described herein onto a surface and evaporating one or more solvents.

[0029] The disclosed technology and accompanying drawings illustrate several implementations of the disclosed technology. [Brief explanation of the drawing]

[0030] [Figure 1] This document describes organic photoresponsive devices according to several embodiments. [Modes for carrying out the invention]

[0031] The drawings are not drawn to scale and have various viewpoints and perspectives. The drawings are several implementations and examples. Furthermore, some components and / or operations may be separated into different blocks or combined into a single block for the purpose of illustrating some of the embodiments of the disclosed technology. Furthermore, while the technology is suitable for various modifications and alternative forms, specific embodiments are shown as examples in the drawings and will be described in detail below. However, the intention is not to limit the technology to the specific implementations described. Rather, the technology is intended to encompass all modifications, equivalents, and alternative forms that fall within the scope of the technology as defined by the appended claims.

[0032] Unless the context clearly indicates otherwise, throughout the specification and claims, words such as “including,” and “including,” should be interpreted in a comprehensive sense, as opposed to an exclusive or exhaustive sense; that is, “including but not limited to.” Furthermore, the words “as herein,” “above,” “below,” and words of similar meaning, when used in this application, refer to the entire application and not to any particular part thereof. Where the context allows, descriptive words using singular or plural may also include plural or singular, respectively. The word “or,” relating to a list of two or more items, encompasses all of the following interpretations of the word: any of the items in the list, all of the items in the list, and any combination of the items in the list. When used in this application, a “layer over” another layer means that the layers may be in direct contact or one or more intervening layers may be present. When used in this application, a “layer on” another layer means that the layers are in direct contact. References to specific chemical elements include any isotopes of that element unless otherwise specified.

[0033] The teachings of the techniques provided herein may be applied to systems other than those described below. The elements and operations of the various examples described below may be combined to provide further implementations of the Technique. Some alternative implementations of the Technique may include fewer elements than the implementations described below, as well as additional elements.

[0034] These and other modifications can be made to the Art in light of the following detailed description. The description illustrates specific examples of the Art and the intended best mode, but regardless of how detailed the description is, the Art can be implemented in many ways. As stated above, any specific term used when describing a particular feature or aspect of the Art should not be construed as meaning that the term is redefined herein to limit the term to any particular characteristic, feature, or aspect of the Art to which it relates. In general, the terms used in the following claims should not be construed as limiting the Art to the specific examples disclosed herein unless such terms are explicitly defined in the detailed description section. Thus, the actual scope of the Art includes not only the disclosed examples but also all equivalent methods of carrying out or implementing the Art based on the claims.

[0035] To reduce the number of claims, certain aspects of the present technology are presented below in the form of certain claims, although the applicant has envisioned various aspects of the present technology in the form of any number of claims.

[0036] In the following description, many specific details are described in order to provide a complete understanding of the implementations of the disclosed technology for illustrative purposes. However, it will be apparent to those skilled in the art that embodiments of the disclosed technology can be implemented without some of these specific details.

[0037] This disclosure provides compounds of formulas (I) and (II).

[0038] A 1 -( B1 )x 1 -(D 1 )y 1 -( B 1 )x 2 -A 1 (I) A 1 -( B 2 )x 5 -(D 2 )y 2 -( B 3 )x 3 -A 2 -( B 3 )x 4 -(D 3 )y 3 -( B 2 )x 6 -A 1 (II) A 1 It is a monovalent electron-accepting group.

[0039] A 2 It is a divalent heteroaromatic electron-accepting group.

[0040] D 1 , D 2 and D 3 In each instance, it is an electron-donating group.

[0041] B 1 B 2 and B 3 Each instance is independently a bridging group.

[0042] x 1 -x 6 Each of these is independently 0, 1, 2, or 3, preferably 0 or 1.

[0043] In some embodiments, x 1 and x 2 They are the same, preferably both are 0 or both are 1.

[0044] In some embodiments, x 1 and x2 One of x1 is 0, and the other of x1 and x2 is 1.

[0045] x 3 and x 4 They are preferably the same, preferably both are 0 or both are 1, more preferably both are 0.

[0046] x 5 and x 6 They are preferably the same, preferably both are 0 or both are 1.

[0047] y 1 , y 2 and y 3 Each of these is independently at least 1, preferably 1, 2, or 3. 2 and y 3 It is preferable that they are the same.

[0048] Electron-accepting group A 1 and A 2 Each of these is (D) in the case of equation (I). 1 )y 1 Deeper than the LUMO (i.e., further away from the vacuum), in the case of equation (II), (D 2 )y 2 and (D 3 )y 3 These are the lowest unoccupied orbital (LUMO) levels, which are deeper than both of the above, preferably at least 1 eV deeper. The LUMO levels of electron-accepting and electron-donating groups can be determined by modeling the LUMO levels of these groups in which each bond to an adjacent group is replaced by a bond to a hydrogen atom. The modeling can be done using Gaussian09 software, available from Gaussian, with Gaussian09 in conjunction with the B3LYP (functional) and 6-31G(D)* (basis set).

[0049] In some embodiments, the compound of formula (I) or (II) may have an absorption peak above 900 nm, an absorption peak above 1100 nm, or an absorption peak above 1250 nm. Preferably, the absorption peak is below 1500 nm.

[0050] at least one A 1 Preferably each A 1 is the base of equation (III), (IV), or (V). [Table 2] Each R 1 R is an independent substituent. Preferably, each R 1 CN and C are independent. 1-6 Fluoroalkyl, preferably CF3, and COOR 40 Selected from, where R 40 In each occurrence, H or a substituent, preferably H or C 1-20 It is a hydrocarbyl group. CN is preferred.

[0051] Anywhere in this specification, C 1-20 The hydrocarbyl group may be unsubstituted, or C 1-12 Alkyl and linear, branched, or cyclic carbon atoms 1-20 Phenyl may be selected, which may be substituted with one or more substituents selected from alkyl groups.

[0052] R 2 is H or a substituent. Preferably, R 2 These are H, F, Cl, CN, NO2, C 1-20 Alkyl or C 1-20 It is an alkoxy, and here, C 1-20 Alkyl or C 1-20 One or more H atoms in the alkoxy may be replaced with F atoms.

[0053] --- is A to donor group D, or to crosslinking group B if present. 1 This represents the connection point.

[0054] Ar 1 This is selected from benzene, 1,2,3-triazole, 1,2,5-thiadiazole, 1,2,3-thiadiazole, and a 6-membered heteroaromatic group in which the ring atom is selected from C and N.

[0055] Ar 1 You can choose from the following options. [Table 3] In the formula, R 5 In each occurrence, independently, H or a substituent, and R 6 is either H or a substituent.

[0056] R 5 In each occurrence, H and C are independently present, preferably independently. 1-20 Alkyl (where C 2-20 One or more non-adjacent C atoms of the alkyl group are O, S, or NR 6 (which may be replaced by ), and an electron-withdrawing group, more preferably H or an electron-withdrawing group. Preferred electron-withdrawing groups are F, Cl, Br, CN, C 1-12 Fluoroalkyl and COOR 15 And here, R 15 is C 1-20 It is a hydrocarbyl group.

[0057] Any NR described anywhere in this specification 6 or PR 6 Each R 6 H and C are independent of each other. 1-20 Alkyl (where one or more non-adjacent carbon atoms other than the carbon atom bonded to N or P are replaced by O, S, COO or CO, and one or more hydrogen atoms of the alkyl are replaced by F), and phenyl (where it is unsubstituted or has one or more substituents (one or more C)). 1-12It may be substituted with an alkyl group, and one or more non-adjacent C atoms of the alkyl group may be substituted with O, S, COO or CO, and one or more H atoms of the alkyl group may be substituted with F) selected from. Preferably, R 6 H, C 1-20 The alkyl group is either unsubstituted or has one or more C atoms. 1-6 It may be substituted with an alkyl group.

[0058] A 1 If is a base of equation (III), then Z 1 and Z 2 Each of them operates independently, CR 4 And selected from N, in this case, R 4 is H or a substituent, however Ar 1 If Z is benzene, 1 and Z 2 At least one of them is N.

[0059] In some embodiments, Z 1 and Z 2 CR 4 And Ar 1 The group is selected from 1,2,3-triazoles, 1,2,5-thiadiazoles, 1,2,3-thiadiazoles, and 6-membered heteroaromatic groups in which the ring atom is selected from C and N.

[0060] In some embodiments, Z 1 and Z 2 One of them is N, and Z 1 and Z 2 The other is CR 4 is or Z 1 and Z 2 Both are N, and Ar 1 The ring atoms are selected from benzene 1,2,3-triazole, 1,2,5-thiadiazole, 1,2,3-thiadiazole, and a 6-membered heteroaromatic group in which the ring atom is selected from C and N.

[0061] A 1 If is a base of equation (IV), then Z3 and Z 4 Each of them operates independently, CR 4 and selected from N, where R 4 is H or a substituent, however Ar 1 If Z is benzene, 3 and Z 4 At least one of them is N.

[0062] In some embodiments, Z 3 and Z 4 CR 4 And Ar 1 The group is selected from 1,2,3-triazoles, 1,2,5-thiadiazoles, 1,2,3-thiadiazoles, and 6-membered heteroaromatic groups in which the ring atom is selected from C and N.

[0063] In some embodiments, Z 3 and Z 4 One of them is N, and Z 3 and Z 4 The other is CR4, or Z 3 and Z 4 Both are N, and Ar 1 The ring atoms are selected from benzene, 1,2,3-triazole, 1,2,5-thiadiazole, 1,2,3-thiadiazole, and a 6-membered heteroaromatic group in which the ring atom is selected from C and N.

[0064] A 1 If is the basis of equation (V), then Z 5 and Z 6 Each of them operates independently, CR 4 and selected from N, where R 4 is H or a substituent, except when Ar1 is benzene, Z 5 and Z 6 At least one of them is N.

[0065] In some embodiments, Z 5 and Z 6 CR 4 And Ar 1The group is selected from 1,2,3-triazoles, 1,2,5-thiadiazoles, 1,2,3-thiadiazoles, and a 6-membered heteroaromatic group in which the ring atom is selected from C and N.

[0066] In some embodiments, Z 5 and Z 6 One of them is N, and Z 3 and Z 4 The other is CR 4 is or Z5 and Z 6 Both are N, and Ar 1 The group is selected from benzene, 1,2,3-triazole, 1,2,5-thiadiazole, 1,2,3-thiadiazole, and a 6-membered heteroaromatic group in which the ring atom is selected from C and N.

[0067] Each R 4 is independently H or a substituent, and H or H, C 1-20 Alkyl (where C 2-20 One or more non-adjacent non-terminal C atoms of the alkyl group are O, S, NR 6 The substituents may be CO or COO, and a substituent selected from electron-withdrawing groups. Preferred electron-withdrawing groups are F, Cl, Br, CN, and C. 1-12 Fluoroalkyl and COOR 15 And here, R 15 is C 1-20 It is a hydrocarbyl group. Preferably, R 4 H is H.

[0068] Wherever used herein, “non-terminal C atom” of an alkyl group means a C atom other than the C atom of the terminal methyl group of an n-alkyl chain or the C atom of the terminal methyl group of a branched alkyl chain.

[0069] Wherever described herein, if a carbon atom of an alkyl group is replaced by another atom or group, the replaced carbon atom may be a terminal carbon atom or an unterminal carbon atom of the alkyl group.

[0070] Anywhere in this specification, when the terminal C atom of a described group is substituted, the resulting group can be an anionic group containing a counter cation, such as ammonium or a metal counter cation, preferably ammonium or an alkali metal cation.

[0071] Anywhere in this specification, the C atom of an alkyl substituent replaced by another described atom or group is preferably a non-terminal C atom, and the resulting substituent is preferably non-ionic.

[0072] Exemplary groups of formula (III) include, but are not limited to, the following. [Table 4] TIFF2026067815000009.tif60138 Each of these may be unsubstituted or substituted with one or more substituents.

[0073] Exemplary groups of formula (IV) include, but are not limited to, the following. [Table 5] TIFF2026067815000011.tif150153

[0074] Exemplary groups of formula (V) include, but are not limited to, the following. [Table 6] TIFF2026067815000013.tif213142 A of the compound of formula (I) 1 group or A of the compound of formula (II) 1 group may be the same or different, preferably the same.

[0075] Acceptor unit A 2 A of the compound of formula (II) 2It is preferable that the group is a condensed heteroaromatic group containing at least two condensed rings, preferably at least three condensed rings.

[0076] In some embodiments, formula (II) A 2 This is the basis of equation (VIII). [ka] During the ceremony, Ar 2 is an aromatic or heteroaromatic group, Y is O, S, NR 6 or R 7 -C=CR 7 And here, R 7 In each occurrence, independently, H or a substituent and two substituents R 7 These may be linked together to form a monocyclic or polycyclic ring, R 6 is either H or a substituent.

[0077] A 2 If is the basis of equation (VIII), then Ar 2 is either non-substituted or one or more R 9 It may be a monocyclic or polycyclic heteroaromatic group substituted with a group, where R 9 Each of these is an independent substituent in its respective appearance.

[0078] Preferred R 9 The base is selected from the following:

[0079] F, CN Sofa NO2, C 1-20 Alkyl, where one or more non-adjacent C atoms are O, S, NR 17 It may also be replaced with R 17 C 1-12 Hydrocarbyl, COO, or CO, where one or more H atoms of the alkyl group may be replaced by F. Aromatic or heteroaromatic group, preferably phenyl, which is unsubstituted or substituted with one or more substituents, and Select from the following bases: [ka] or [ka] In the formula, Z 40 , Z 41 , Z 42 and Z 43 Each of them operates independently, CR 13 or N, R 13 In each occurrence, H or a substituent, preferably C 1-20 It is a hydrocarbyl group, Y 40 and Y 41 These are O, S, and NX, which are independent of each other. 71 (Here, X 71 is CN or COOR 40 ), or CX 60 X 61 (Here, X 60 and X 61 These are independently CN, CF3, or COOR 40 ) and W 40 and W 41 These are O, S, and NX, which are independent of each other. 71 or CX 60 X 61 (Here, X 60 and X 61 These are independently CN, CF3, or COOR 40 ) and R 40 In each occurrence, H or a substituent, preferably H or C 1-20 It is a hydrocarbyl group. It is an aromatic or heteroaromatic group R. 9 Exemplary substituents include F, CN, NO2, and C 1-12 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 7, may be replaced by COO or CO, and one or more H atoms of the alkyl may be replaced by F).

[0080] Anywhere in this specification, the described R 17 is, for example, C 1-12 alkyl, unsubstituted phenyl, or phenyl substituted with one or more C 1-6 alkyl groups.

[0081] Exemplary monocyclic heteroaromatic group Ar 2 is oxadiazole, thiadiazole, triazole, and 1,4-diazine which is unsubstituted or substituted with one or more substituents. Thiadiazole is particularly preferred.

[0082] Exemplary polycyclic heteroaromatic group Ar 2 is a group of formula (V).

Chemical formula

[0083] X 3 , X 4 , X 5 and X 6 are each independently selected from N and CR 10 , provided that at least one of X 3 , X 4 , X <000034 "]]and X 6 is CR 10 .

[0084] Z is O, S, SO2, NR 6 , PR 6 , C(R 10 )2, Si(R 10)2C=O, C=S and C=C(R 5 ) Selected from 2, where R 10 As stated above, R 6 is H or a substituent, and R 5 In each instance, it is an electron-withdrawing group.

[0085] Preferably, each R 5 CN, COOR 40 , or CX 60 X 61 And here, X 60 and X 61 These are independently CN, CF3, or COOR 40 And R 40 In each occurrence, H or a substituent, preferably H or C 1-20 It is a hydrocarbyl group.

[0086] A of equation (VIII) 2 The base is preferably selected from the bases of formulas (VIIIa) and (VIIIb). [Table 7] In the case of the compound of formula (VIIIb), there are two R 7 The bases may or may not be connected.

[0087] Preferably, two R 7 If the bases are not linked, each R 7 These are independently H, F, CN, NO2, C 1-20 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 7 CO, COO, NR 6 PR 6 or Si(R 10 ) may be replaced with 2, R 10 and R 6As described above, one or more H atoms may be replaced by F, and selected from aryl or heteroaryl groups, preferably phenyl (these may be unsubstituted or substituted with one or more substituents). The substituents of the aryl or heteroaryl group are F, CN, NO2, and C 1-20 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 6 (These may be replaced by CO, COO, or one or more H atoms may be replaced by F) and may be selected from these.

[0088] Preferably, two R 7 When the groups are linked, the group of formula (VIIIb) has either formula (VIIIb-1) or (VIIIb-2). [Table 8] Ar 3 is an unsubstituted or substituted aromatic or heteroaromatic group, preferably benzene. 3 R may be unsubstituted, or one or more of the substituents R described above. 9 It may be replaced with .

[0089] X is O, S, SO2, NR 6 PR 6 , C(R 10 )2, Si(R 10 )2C=O, C=S and C=C(R 7 ) Selected from 2, where R 10 , R 6 and R 7 The above is true.

[0090] Examples of electron-accepting groups in formula (VIII) include, but are not limited to, the following: [Table 9] During the ceremony, Ak 1 is C 1-20It is an alkyl group Divalent electron-accepting groups A other than formula (VIII) 2 This may be selected from equation (IVa)-(IVj). [Table 10] Y A1 is O or S, preferably S.

[0091] R 23 In each appearance, is a substituent, C 1-12 It may also be alkyl, and here, Z 3 One or more non-adjacent carbon atoms other than the bonded carbon atom are O, S, NR 6 It may be replaced with COO or CO, and one or more H atoms of the alkyl may be replaced with F.

[0092] R 25 In each occurrence, H, F, CN, NO2, and C appear independently. 1-12 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 6 (which may be replaced with COO or CO, and which may have one or more H atoms of the alkyl replaced with F), aromatic group (which may be phenyl) (which may be unsubstituted or have F and C) 1-12 It is substituted with one or more substituents selected from alkyl, where one or more non-adjacent C atoms are O, S, NR 6 (which may be replaced with COO or CO), or [ka] or [ka] , (In the formula, Z 40 , Z 41 , Z 42 and Z 43 Each of them operates independently, CR 13Or N, where R 13 In each occurrence, H or a substituent, preferably C 1-20 It is a hydrocarbyl group, Y 40 and Y 41 These are O, S, and NX, which are independent of each other. 71 And here, X 71 CN or COOR 40 , or CX 60 X 61 And here, X 60 and X 61 These are independently CN, CF3, or COOR 40 And, W 40 and W 41 These are O, S, and NX, which are independent of each other. 71 And here, X 71 CN or COOR 40 , or CX 60 X 61 And here, X 60 and X 61 These are independently CN, CF3, or COOR 40 And, R 40 In each occurrence, H or a substituent, preferably H or C 1-20 It is a hydrocarbyl group.

[0093] Z 3 It is either N or P.

[0094] T 1 , T 2 and T 3 Each of these independently represents an aryl ring or heteroaryl ring (which may be benzene) that may be fused to one or more further rings. 1 , T 2 and T 3 If the substituent is present, R 25 The non-H group may be selected from the following. In a preferred embodiment, T 3 It is benzothiadiazole.

[0095] R 12 In each occurrence, a substituent, preferably C 1-20 It is a hydrocarbyl group.

[0096] Ar 5 R is an arylene or heteroarylene group, which may be thiophene, fluorene or phenylene, which may be unsubstituted or substituted with one or more substituents, 25 It may be substituted with one or more non-H groups selected from the following.

[0097] Bridge unit Bridge Unit B 1 B 2 and B 3 Each of these is preferably selected from vinylene, arylene, heteroarylene, arylenevinylene, and heteroarylenevinylene, and the arylene group and heteroarylene group are monocyclic or bicyclic groups, and may be unsubstituted or substituted with one or more substituents.

[0098] B 1 B 2 and B 3 The vinylene unit and arylene unit or heteroarylene unit of formula (VIa)-(VIn) may be selected. [Table 11] In the formula, R 6 is H or a substituent, R 8 In each occurrence, independently, H or a substituent, preferably H or F, CN, NO2, C 1-20 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 6 R in formulas (VIa), (VIb), and (VIc) is a substituent selected from (which may be replaced by COO or CO, and one or more H atoms of the alkyl may be replaced by F), and phenyl (which is unsubstituted or substituted with one or more substituents).8 The groups may be linked together to form a bicyclic ring, such as a thienopyrazine.

[0099] R 8 Preferably H, C 1-20 Alkyl or C 1-19 It is an alkoxy.

[0100] Electron-donating group D 1 , D 2 and D 3 The electron-donating group is preferably a condensed aromatic group or a heteroaromatic group, more preferably a condensed heteroaromatic group containing three or more rings. Particularly preferred electron-donating groups include a condensed thiophene or furan ring, and may also include a condensed ring comprising a thiophene or furan ring and one or more rings selected from benzene, cyclopentadiene, tetrahydropyran, tetrahydrothiopyran, and piperidine rings, each of which is either unsubstituted or substituted with one or more substituents.

[0101] Example electron-donating group D 1 , D 2 and D 3 This includes the base of equation (VIIa)-(VIIt). [Table 12] TIFF2026067815000026.tif188158

[0102] In the formula, Y A In each occurrence, independently, O, S, or NR 55 Y A1 In each occurrence, independently, it is either O or S, and X A is C or Si, Z A In each occurrence, O, CO, S, NR 55 or C(R 54 )2, R 51 , R 52 , R 54 and R 55In each occurrence, independently, H or a substituent, and R 53 In each occurrence, independently, is a substituent, and Ar 4 is a monocyclic or fused heteroaromatic group that may be substituted.

[0103] R 51 and R 52 In each occurrence, H, F, and C appear independently. 1-20 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 7 (which may be replaced by COO or CO, and which may have one or more H atoms replaced by F), and aromatic or heteroaromatic groups Ar 3 (This may be selected from being unsubstituted or substituted with one or more substituents.)

[0104] In some embodiments, Ar 3 This may be an aromatic group, such as phenyl.

[0105] Ar 4 The oxadiazole is preferably selected from oxadiazoles, thiadiazoles, triazoles, and 1,4-diazines, which may be substituted. 4 If is a 1,4-diazine, the 1,4-diazine may be condensed to a further heterocyclic group, or to a group selected from substituted oxadiazoles, thiadiazoles, triazoles, 1,4-diazines, and succinimides.

[0106] Ar 3 If one or more substituents of are present, C 1-12 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 7 (These may be replaced by COO or CO, and one or more H atoms of the alkyl group may be replaced by F)

[0107] Preferably, each R 54 The group is selected from the following:

[0108] H, F, Linear, branched, or ring C 1-20 Alkyl, where one or more non-adjacent C atoms are O, S, NR 7 , may be replaced with CO or COO, R 17 C 1-12 It is hydrocarbyl, C 1-20 One or more H atoms of the alkyl group may be replaced by F, and Equation (Ak)u-(Ar 7 )v base, in the formula Ak is one or more non-adjacent C atoms O, S, NR 7 C may be replaced by CO or COO. 1-20 It is an alkylene chain, where u is 0 or 1, Ar 7 In each occurrence, is an aromatic or heteroaromatic group that is either unsubstituted or substituted with one or more substituents, and v is at least 1, and may be 1, 2, or 3.

[0109] Ar 7 The substituents, if present, are preferably F, Cl, NO2, CN, and C 1-20 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 7 Selected from (which may be replaced by CO or COO, and which may have one or more H atoms replaced by F). Preferably Ar 7 It is phenyl.

[0110] Preferably, each R 51 H is H.

[0111] R 53 In each occurrence, C 1-20 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 7(which may be replaced by COO or CO, and one or more H atoms of the alkyl may be replaced by F), and phenyl (which is unsubstituted or substituted with one or more substituents, and one or more C 1-12 It may be substituted with an alkyl group, and one or more non-adjacent C atoms are O, S, NR 7 (The alkyl group may be substituted with COO or CO, and one or more H atoms of the alkyl group may be substituted with F.)

[0112] Preferably, anywhere in this specification, the R described 55 is H or C 1-30 It is a hydrocarbyl group.

[0113] In a preferred embodiment, D 1 , D 2 and D 3 Each of these is an independent base of equation (VIIa). Examples of exemplary bases of equation (VIIa) include, but are not limited to, the following: [Table 13] In the formula, Hc is independently C in each occurrence. 1-20 Hydrocarbyl group, for example, C 1-20 Alkyl, unsubstituted aryl, or one or more C 1-12 It is an aryl group substituted with an alkyl group. The aryl group is preferably phenyl.

[0114] In some embodiments, y in equation (I) 1 It is 1.

[0115] In some embodiments, y in equation (II) 2 and y 3 Each of these values ​​is 1.

[0116] In some embodiments, y in equation (I) 1 or y in equation (II) 2 and y 3At least one of them is greater than 1. In these embodiments, D 1 , D 2 Or D 3 The chains of the elements may be linked in any orientation. For example, D 1 is the basis of equation (VIIa), and y 1 If it is 2, then -[D 1 ] y1 - may be selected from one of the following: [ka] Examples of compounds representing formula (I) include, but are not limited to, the following: [ka] [ka]

[0117] Electron-donating materials The bulk heterojunction layer described herein comprises an electron-donating material and a compound of formula (I) or (II) as described herein.

[0118] Exemplary donor materials are disclosed, for example, in International Publication No. 2013 / 051676, which is incorporated herein by reference.

[0119] The electron-donating material may be a non-polymer or polymer material.

[0120] In preferred embodiments, the electron-donating material is an organic conjugated polymer, which may be a homopolymer or a copolymer comprising alternating, random, or block copolymers. The conjugated polymer is preferably a donor-acceptor polymer comprising alternating electron-donating repeating units and electron-accepting repeating units.

[0121] Amorphous or semi-crystalline conjugated organic polymers are preferred.

[0122] More preferably, the electron-donating polymer is a conjugated organic polymer having a low band gap, typically 2.5 eV to 1.5 eV, preferably 2.3 eV to 1.8 eV.

[0123] Electron-donating polymers may have a HOMO level of 5.5 eV or less from the vacuum level. Electron-donating polymers may have a HOMO level of at least 4.1 eV from the vacuum level. Examples of electron-donating polymers include polyacene, polyaniline, polyazulene, polybenzofuran, polyfluorene, polyfuran, polyindenofluorene, polyindole, polyphenylene, polypyrazoline, polypyrene, polypyridazine, polypyridine, polytriarylamine, poly(phenylenevinylene), poly(3-substituted thiophene), poly(3,4-disubstituted thiophene), polyselenophene, poly(3-substituted selenophene), poly(3,4-disubstituted selenophene), poly(bisthiophene), poly Examples of polymers include (terthiophene), poly(bisselenophene), poly(terselenophene), polythieno[2,3-b]thiophene, polythieno[3,2-b]thiophene, polybenzothiophene, polybenzo[1,2-b:4,5-b']dithiophene, polyisothianaphthene, poly(monosubstituted pyrrole), poly(3,4-disubstituted pyrrole), poly-1,3,4-oxadiazole, polyisothianaphthene, their derivatives and copolymers, selected from conjugated hydrocarbons or heterocyclic polymers.

[0124] Preferred donor polymers include copolymers of polyfluorene and polythiophene, each of which may be substituted, as well as polymers comprising benzothiadiazole and thiophene repeating units, each of which may be substituted.

[0125] Particularly preferred donor polymers are most preferably electron-accepting repeating units, such as the divalent electron-accepting unit A described herein, provided as a polymer repeating unit. 1 It also includes a donor unit (VIIa) provided as a repeating unit of polymer.

[0126] Another particularly preferred donor polymer comprises repeating units of formula (X). [ka] In the formula, R 18 and R 19 These are H, F, and C, respectively, independently. 1-12 Alkyl (where one or more non-adjacent non-terminal C atoms may be replaced with O, S, COO, or CO, and one or more H atoms of the alkyl may be replaced with F) or aromatic or heteroaromatic group Ar 6 (This is either non-substituted or F and C 1-12 It is substituted with one or more substituents selected from alkyl groups, where one or more non-adjacent non-terminal C atoms may be substituted with O, S, COO, or CO.

[0127] The donor polymer is preferably a donor-acceptor (DA) copolymer comprising donor repeating units, for example, repeating units of formula (VIIa) or (X), and acceptor repeating units.

[0128] Organic electronic devices Compounds of formula (I) or (II) may be provided as active layers for organic electronic devices. In preferred embodiments, the bulk heterojunction layer of an organic photoresponsive device, more preferably an organic photodetector, comprises the compositions described herein.

[0129] The bulk heterojunction layer comprises or consists of the electron-donating material and the electron-accepting compound of formula (I) or (II) described herein.

[0130] In some embodiments, the bulk heterojunction layer comprises two or more acceptor materials and / or two or more electron-accepting materials.

[0131] In some embodiments, the weight ratio of electron-donating material to electron-accepting material is about 1:0.5 to about 1:2, preferably about 1:1.1 to about 1:2.

[0132] Preferably, the electron-donating material has a type II interface with the electron-accepting material, i.e., the electron-donating material has HOMO and LUMO levels that are shallower than the corresponding HOMO and LUMO levels of the electron-accepting material. Preferably, the compound of formula (I) or (II) has a HOMO level that is at least 0.05 eV deeper than the HOMO of the electron-donating material, and may be at least 0.10 eV deeper.

[0133] The gap between the HOMO level of the electron-donating material and the LUMO level of the electron-accepting compound of formula (I) or (II) may be less than 1.4 eV.

[0134] Unless otherwise stated, the HOMO and LUMO levels of materials described herein are measured by square wave voltammetry (SWV).

[0135] Figure 1 shows an organic photoresponsive device according to several embodiments of the present disclosure. The organic photoresponsive device includes a cathode 103, an anode 107, and a bulk heterojunction layer 105 disposed between the anode and the cathode. The organic photoresponsive device may be supported on a substrate 101, which may be a glass or plastic substrate.

[0136] The anode and cathode may each be an independent single conductive layer, or they may consist of multiple layers.

[0137] At least one of the anode and cathode is transparent so that light incident on the device can reach the bulk heterojunction layer. In some embodiments, both the anode and cathode are transparent. The transmittance of the transparent electrode can be selected depending on the emission wavelength of the light source used with the organic photodetector.

[0138] Figure 1 shows an arrangement where the cathode is positioned between the substrate and the anode. In other embodiments, the anode may be positioned between the cathode and the substrate.

[0139] The organic photoresponsive device may include layers other than the anode, cathode, and bulk heterojunction layer shown in Figure 1. In some embodiments, a hole transport layer is located between the anode and the bulk heterojunction layer. In some embodiments, an electron transport layer is located between the cathode and the bulk heterojunction layer. In some embodiments, a work function alteration layer is located between the bulk heterojunction layer and the anode, and / or between the bulk heterojunction layer and the cathode.

[0140] The area of ​​the OPD is approximately 3 cm². 2 Less than approximately 2 cm 2 Less than approximately 1 cm 2 Less than approximately 0.75 cm 2 Less than approximately 0.5 cm 2 Less than, or approximately 0.25 cm 2 It may be less than 1 mm. Each OPD may be part of an OPD array, and each OPD is a pixel of an array having the area described herein, 1 mm 2 The area may be less than 0.5 microns. 2 -900 microns 2 The area within that range may also be acceptable.

[0141] The substrate may be, but is not limited to, glass or plastic. The substrate may also be an inorganic semiconductor. In some embodiments, the substrate may be silicon. For example, the substrate may be a silicon wafer. The substrate is transparent if, during use, incident light passes through the substrate and the electrodes supported by the substrate.

[0142] The bulk heterojunction layer contains a compound of formula (I) or (II) as described herein and an electron-donating compound. The bulk heterojunction layer may consist of these materials, or it may contain one or more further materials, such as one or more further electron-donating materials and / or one or more further electron-accepting compounds.

[0143] Fullerene In some embodiments, the compound of formula (I) or (II) is the sole electron-accepting material for the bulk heterojunction layer described herein.

[0144] In some embodiments, the bulk heterojunction layer comprises a compound of formula (I) or (II) and one or more further electron-accepting materials. A preferred further electron-accepting material is a fullerene. Surprisingly, the inventors have found that combining a compound of formula (I) or (II) with a fullerene can increase the external quantum efficiency of the OPD with little or no increase in dark current.

[0145] The weight ratio of the compound of formula (I) or (II) to the fullerene acceptor may be in the range of about 1:0.1 to 1:1, preferably in the range of about 1:0.1 to 1:0.5. The fullerene is, but is not limited to, C 60 , C 70 , C 76 , C 78 and C 84 Fullerene, or, but not limited to, phenyl-C 61 -Methyl butyrate (C 60 PCBM-type fullerene derivatives including PCBM, TCBM-type fullerene derivatives (e.g., tolyl-C) 61 -Methyl butyrate (C 60 TCBM)), and ThCBM-type fullerene derivatives (e.g., thienyl-C) 61 -Methyl butyrate (C 60 They can be selected from their derivatives, including ThCBM.

[0146] The fullerene derivative may have formula (VI). [ka] In the formula, A, together with the CC group of the fullerene, forms a monocyclic or fused ring group which may be unsubstituted or substituted with one or more substituents.

[0147] Exemplary fullerene derivatives include formulas (VIa), (VIb), and (VIc). [Table 14] In the formula, R 20 -R 32 Each of these is independently either H or a substituent.

[0148] Substituent R 20 -R 32 In each occurrence, independently, aryl or heteroaryl (which may be phenyl) may be unsubstituted or substituted with one or more substituents, and C 1-20 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 7 (These may be selected from the group consisting of CO or COO, and one or more H atoms may be replaced by F.)

[0149] If present, the aryl or heteroaryl substituent is C 1-12 Alkyl (where one or more non-adjacent C atoms are O, S, NR) 7 (These may be replaced by CO or COO, and one or more H atoms may be replaced by F) and selected from the above.

[0150] compound The bulk heterojunction layer can be formed by any method, including but not limited to thermal deposition and solution deposition.

[0151] Preferably, the bulk heterojunction layer is formed by depositing a formulation containing an electron-donating material, an electron-accepting material, and any other components of the bulk heterojunction layer, dissolved or dispersed in a solvent or a mixture of two or more solvents. The formulation may be deposited by any coating or printing method, including but not limited to spin coating, dipping coating, roll coating, spray coating, doctor blade coating, wire bar coating, slit coating, inkjet printing, screen printing, gravure printing, and flexographic printing.

[0152] One or more solvents in the formulation are fluorine, chlorine, and C 1-10 Alkyl and C 1-10 Benzene or naphthalene substituted with one or more substituents selected from alkoxy (where two or more substituents may be unsubstituted, or one or more C 1-6 It may contain or consist of (toluene, xylene, trimethylbenzene, tetramethylbenzene, anisole, indan and its alkyl-substituted derivatives, and tetralin and its alkyl-substituted derivatives) (which may be linked to form a ring which may be substituted with an alkyl group).

[0153] The formulation may comprise a mixture of two or more solvents, preferably a mixture comprising at least one benzene substituted with one or more substituents and one or more further solvents. The one or more further solvents may be selected from esters which may be alkyl esters or aryl esters of alkyl carboxylic acids or aryl carboxylic acids, C 1-10 Alkyl benzoates, benzyl benzoates, or dimethoxybenzene may be selected. In preferred embodiments, a mixture of trimethylbenzene and benzyl benzoate is used as the solvent. In other preferred embodiments, a mixture of trimethylbenzene and dimethoxybenzene is used as the solvent.

[0154] The formulation may include, in addition to the electron-accepting material, electron-donating material, and one or more solvents, further components. Examples of such components include adhesives, defoamers, degassing agents, thickeners, diluents, additives, flow improvers, colorants, dyes or pigments, sensitizers, stabilizers, nanoparticles, surfactants, lubricants, wetting agents, dispersants, and inhibitors.

[0155] Purpose The circuit may include an OPD connected to a voltage source for applying a reverse bias to the device, and / or a device configured to measure the photocurrent. The voltage applied to the photodetector may be variable. In some embodiments, the photodetector may be continuously biased during use.

[0156] In some embodiments, the photodetector system comprises a plurality of photodetectors as described herein, such as the image sensor of a camera.

[0157] In some embodiments, the sensor may include an OPD and a light source as described herein, the OPD being configured to receive light emitted from the light source. In some embodiments, the light source may have a peak wavelength of at least 900 nm or at least 1000 nm, and may have a peak wavelength in the range of 900–1500 nm.

[0158] In some embodiments, the light from the light source may or may not be modified before reaching the OPD. For example, the light may be reflected, filtered, downconverted, or upconverted before reaching the OPD.

[0159] The organic photoresponsive devices described herein may also be organic photovoltaic devices or organic photodetectors. The organic photodetectors described herein may be used in a wide range of applications, including, but not limited to, the detection of the presence and / or brightness of ambient light, and in sensors including organic photodetectors and light sources. The photodetector may be configured such that light emitted from a light source is incident on the photodetector and changes in the wavelength and / or brightness of the light are detected, resulting from absorption, reflection, and / or emission from an object, such as a target material in a sample placed in the optical path between the light source and the organic photodetector. The sample may be a non-biological sample, such as a water sample, or a biological sample taken from a human or animal subject. The sensor may be, but not limited to, a gas sensor, a biosensor, an image sensor such as an X-ray imaging device or a camera image sensor, a motion sensor (e.g., for use in security applications), a proximity sensor, or a fingerprint sensor. A 1D or 2D photosensor array may comprise a plurality of photodetectors described herein in an image sensor. The photodetector may be configured to detect light emitted from a target analyte that emits light when irradiated by a light source, or from a target analyte coupled to a light-emitting tag that emits light when irradiated by a light source. The photodetector may be configured to detect the wavelength of light emitted by the target analyte or the light-emitting tag coupled to it.

[0160] [Examples] Acceptor Unit 1 Acceptor unit 1 can be prepared according to the following diagram. [ka]

[0161] [Compound Example 1] Compound Example 1 can be prepared according to the following diagram. [ka]

[0162] [Compound Example 2] Compound Example 2 can be prepared according to the following diagram. [ka]

[0163] Modeled data The HOMO and LUMO energy levels of the compounds of equations (I) and (II), as well as comparative compounds, were modeled using Gaussian09 software, available from Gaussian, along with the B3LYP functional and 6-31G(D) basis set.

[0164] To simplify the model, the alkyl group of the model compound was limited to methyl.

[0165] The results are shown in Table 1-7, where S1f corresponds to the oscillator intensity of the transition from S1 (predicting the absorption intensity).

[0166] As shown in these results, the increase in λmax wavelength corresponds to the acceptor group A described herein. 1 This can be achieved by using [this method].

[0167] Tables 1A and 1B are, each A 1 is the basis of equation (III), and -(D 1 ) y1 - provides modeling data for the compound of formula (I), which is the basis of the following formula. [ka]

[0168] Table 1A shows that no crosslinking groups are present.

[0169] In Table 1B, x 1 and x 2 Each of them is 1, B 1 is alkoxy-substituted thiophene crosslinked B 1 That is the case. [Table 15] TIFF2026067815000039.tif227154TIFF2026067815000040.tif179154 [Table 16] TIFF2026067815000042.tif238161 Tables 2A and 2B Tables 2A and 2B are, each A 1 is the basis of equation (III), and -(D 1 ) y1 - provides modeling data for the compound of formula (I), which is the basis of the following formula. [ka]

[0170] Table 2A shows that no crosslinking groups are present.

[0171] In Table 2B, x 1 and x 2 Each of them is 1, B 1 is alkoxy-substituted thiophene crosslinked B 1 That is the case. [Table 17] [Table 18]

[0172] Tables 3A and 3B are each A 1 is the basis of equation (III), and -(D 1 ) y1 - provides modeling data for the compound of formula (I), which is the basis of the following formula. [ka]

[0173] Table 3A shows that no crosslinking groups are present.

[0174] In Table 3B, x 1 and x 2 Each of them is 1, B 1 is alkoxy-substituted thiophene crosslinked B 1 That is the case. [Table 19] [Table 20]

[0175] Tables 4A and 4B are each A 1 is the basis of equation (III), and -(D 1 ) y1 - provides modeling data for the compound of formula (I), which is the basis of the following formula. [ka]

[0176] Table 4A shows that no crosslinking groups are present.

[0177] In Table 4B, x 1 and x 2 Each of them is 1, B 1 is alkoxy-substituted thiophene crosslinked B 1 That is the case. [Table 21] [Table 22]

[0178] Tables 5A and 5B are, each A 1 is the basis of equation (III), and -(D 1 ) y1 - provides modeling data for compounds, which are the basis of the following equation. [ka]

[0179] Table 5A does not contain any crosslinking groups.

[0180] In Table 5B, x 1 and x 2 Each of them is 1, B 1 is alkoxy-substituted thiophene crosslinked B 1 That is the case. [Table 23] [Table 24]

[0181] Table 6 shows each A 1 The base of formula (III) is and there is no bridging group, -(D 1 ) y1 - provides modeling data for compounds, which are the basis of the following equation. [ka] [Table 25]

[0182] Table 7 shows each A 1 This provides modeling data for the compound of formula (I) in which formula (IV) is the base. [Table 26] TIFF2026067815000058.tif59153

[0183] Table 8 shows each A 1 This provides modeling data for the compound of formula (II) in which formula (III) is the base. [Table 27] TIFF2026067815000060.tif213166TIFF2026067815000061.tif183165TIFF2026067815000062.tif231167

Claims

1. A compound of formula (I) or (II), A １ -(B １ )x １ -(D １ )y １ -(B １ )x ２ -A １ (I) A １ -(B ２ )x ５ -(D ２ )y ２ -(B ３ )x ３ -A ２ -(B ３ )x ４ -(D ３ )y ３ -(B ２ )x ６ -A １ (II) During the ceremony, A ２ It is a divalent heteroaromatic electron-accepting group, D １ , D ２ and D ３ In each instance, it is an electron-donating group, B １ , B ２ , and B ３ In each occurrence, it is an independent bridging group. x １ -x ６ These are, independently, 0, 1, 2, or 3. y １ , y ２ and y ３ Each of them is independently at least 1, Each A １ is an electron-accepting group and has at least one A １ is the base of formula (III), (IV), or (V), Table 1 During the ceremony, Each R １ These are independent substituents, R ２ is H or a substituent, Ar １ The compounds are selected from benzene, 1,2,3-triazole, 1,25-thiadiazole, 1,2,3-thiadiazole, and a 6-membered heteroaromatic group in which the ring atom is selected from C and N, and Ar １ It is either unsubstituted or substituted with one or more substituents. --- is A １ It represents the connection point, Z １ -Z ６ In each occurrence, N and CR are independent. ４ Selected from, here, R ４ In each occurrence, is H or a substituent. Ar １ is benzene, A １ If is the aforementioned base of formula (III), then Z １ and Z ２ At least one of them is N, Ar １ is benzene, A １ If is the base of formula (IV), then Z ３ and Z ４ At least one of them is N, Ar １ is benzene, A １ If is the base of formula (V), then Z ５ and Z ６ A compound in which at least one of the elements is N.

2. Ar １ The compound according to claim 1, wherein is benzene.

3. A １ If is a base of equation (III), then Z １ and Z ２ Each of these is N, A １ If is the basis of equation (IV), then Z ３ and Z ４ Each of these is N, A １ If is the basis of equation (V), then Z ５ and Z ６ The compound according to claim 2, wherein each of the elements is N.

4. Ar １ It is 1,4-diazine, A １ If is a base of equation (III), then Z １ and Z ２ These are CR ４ And, A １ If is the basis of equation (IV), then Z ３ and Z ４ These are CR ４ And, A １ If is the basis of equation (V), then Z ５ and Z ６ These are CR ４ The compound according to claim 1.

5. at least one A １ The compound according to any one of claims 1 to 4, wherein is the group of formula (III).

6. Each A １ The compound according to any one of claims 1 to 5, wherein is a group of formula (III), (IV), or (V).

7. Each A １ The compound according to claim 6, wherein the same

8. Each R １ However, independently, CN, CF ３ and COOR ４０ Selected from, here, R ４０ The compound according to any one of claims 1 to 7, wherein in each occurrence, is H or a substituent.

9. Ar １ The compound according to any one of claims 1 to 8, wherein is substituted with at least one electron-withdrawing group.

10. At least one electron-withdrawing group is selected from Br, Cl, F, CN, C １－１２ fluoroalkyl and COOR １５ where R １５ is a C １－２０ hydrocarbyl group, the compound according to claim 9.

11. Each R ４ The compound according to any one of claims 1 to 10, wherein the compound is independently selected from H or an electron-withdrawing group.

12. A composition comprising an electron-donating material and an electron-accepting material, wherein the electron-accepting material is a compound according to any one of claims 1 to 11.

13. An organic electronic device comprising an active layer containing the compound or composition described in any one of claims 1 to 12.

14. The organic electronic device according to claim 13, wherein the organic electronic device is an organic photoresponsive device comprising a bulk heterojunction layer disposed between an anode and a cathode, and the bulk heterojunction layer comprises the composition according to claim 12.

15. The organic electronic device according to claim 14, wherein the organic photoresponsive device is an organic photodetector.

16. A light sensor comprising a light source and an organic photodetector according to claim 15, wherein the organic photodetector is configured to detect light emitted from the light source.

17. The light sensor according to claim 16, wherein the light source emits light having a peak wavelength greater than 900 nm.

18. A formulation comprising a compound or composition according to any one of claims 1 to 12, dissolved or dispersed in one or more solvents.

19. A method for forming an organic electronic device according to any one of claims 13 to 15, wherein the formation of the active layer comprises depositing the formulation according to claim 18 onto a surface and evaporating the one or more solvents.

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