Compound for organic photoelectric device, and organic photoelectric device, image sensor and electronic device comprising same

Abstract

Disclosed according to the present invention are: a compound for an organic photoelectric device, as represented by chemical formula 1; and an organic photoelectric device, an image sensor, and an electronic device comprising the compound. The compound, represented by chemical formula 1, is a material having high sensitivity and high heat resistance and, when applied to an organic photoelectric device, can significantly improve the efficiency and stability of the device.

Description

Compounds for organic photovoltaic devices and organic photovoltaic devices, image sensors, and electronic devices containing the same

[0001] The present invention relates to a compound for an organic photovoltaic device and an organic photovoltaic device, image sensor, and electronic device comprising the same.

[0002] Photovoltaic devices are components capable of converting light into electrical signals using the photoelectric effect, and they can be applied to image sensors. Therefore, the development of photovoltaic devices has been continuously ongoing to develop image sensors.

[0003] As technology development progresses, the resolution of image sensors increases, and consequently, the size of pixels is also becoming smaller. However, as the pixel size decreases, the absorption area shrinks, which can lead to a decrease in sensitivity, and research on optoelectronic devices is actively underway to overcome this.

[0004] Recently, there has been a shift from silicon materials or polymer materials produced using inkjet technology, which are primarily used for optoelectronic devices, to organic materials produced using vacuum deposition. Organic materials possess high absorption coefficients and can be designed to selectively absorb light in specific wavelength ranges depending on their molecular structure. In other words, since organic materials can selectively detect light in desired color ranges by absorbing it, they can simultaneously replace existing optoelectronic devices and color filters. Therefore, organic materials must be capable of providing high sensitivity. Furthermore, there is a need for organic optoelectronic devices that exhibit high efficiency even in high-temperature processes such as vacuum deposition. To address this, it is necessary to develop organic materials with excellent heat resistance.

[0005] Therefore, research is currently needed to develop high-sensitivity and high-heat-resistant materials to realize superior organic optoelectronic devices.

[0006] To address the problems of the aforementioned background technology, the present invention has identified a compound having a novel structure and has also discovered that applying this compound to an organic photovoltaic device can significantly improve the efficiency and stability of the device. Accordingly, the present invention aims to provide a novel compound for organic photovoltaic devices and an organic photovoltaic device, image sensor, and electronic device comprising the same.

[0007] In one aspect, the present invention provides a compound represented by the following chemical formula.

[0008]

[0009] In another aspect, the present invention provides an organic photovoltaic device, an image sensor, and an electronic device thereof, comprising a compound represented by the above chemical formula.

[0010] By using the compound according to the present invention, a material with high sensitivity and high heat resistance can be provided, thereby significantly improving the efficiency and stability of organic photovoltaic devices.

[0011] FIGS. 1 and FIGS. 2 are drawings showing a stacked structure of an organic photovoltaic device according to an embodiment of the present invention.

[0012] Figure 3 shows the IR spectrum of comparative compound A.

[0013] Figure 4 shows the IR spectrum of compound P52 of the present invention.

[0014] [Explanation of the symbol]

[0015] 110: First electrode 120: Second electrode

[0016] 130: Active layer 210: Hole transport band

[0017] 220: Electronic Transport Band

[0018] As used in this specification, the terms "aryl group," "arylene group," and "aromatic ring" refer to hydrocarbon aromatic rings, each having 6 to 60 carbon atoms unless otherwise noted, but are not limited thereto. In the present invention, an aryl group or an arylene group includes a single ring, a polycyclic ring, and a condensed ring, etc.

[0019] As used in this specification, the term "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group, and the term "fluorenylene group" refers to a substituted or unsubstituted fluorenylene group. The fluorenyl group or fluorenylene group used in the present invention includes a spiro compound formed by R and R' being bonded to each other in the following structure, and also includes a compound in which adjacent R" are bonded to each other to form a ring. "Substituted fluorenyl group" and "substituted fluorenylene group" mean that at least one of R, R', and R" in the following structure is a substituent other than hydrogen, and in the chemical formula below, R" may be 1 to 8. In this specification, regardless of the valence, the fluorenyl group, fluorenylene group, etc. may be described as a fluoren group or fluoren.

[0020]

[0021] The term "spyro compound" as used in this specification refers to a compound having a "spyro linkage," where a spyro linkage is a connection formed by two rings sharing only one atom. In this case, the atom shared between the two rings is called a "spyro atom," and depending on the number of spyro atoms contained in a compound, they are respectively called "monospyro-," "diespyro-," and "trispyro-" compounds.

[0022] The term "heterocyclic group" as used in this specification includes not only aromatic heterocyclic groups such as "heteroaryl groups" or "heteroarylene groups" but also non-aromatic heterocyclic groups, and unless otherwise noted, means a ring having 2 to 60 carbon atoms containing one or more heteroatoms, but is not limited thereto. The term "heteroatom" as used in this specification refers to an element other than carbon, such as N, O, S, P, Si, Se, Te, etc., unless otherwise noted, and may include heteroatom groups such as SO2, P=O, etc., as in the following compounds, instead of carbon forming the ring.

[0023]

[0024] In addition, heterocyclic rings include monocyclic, polycyclic, or condensed rings containing heteroatoms, and in the case of condensed rings, if at least one of the condensed rings is a ring containing a heteroatom, it is defined as a heterocyclic ring. For example, heterocyclic rings such as furan, dihydrofuran, thiophene, pyrrole, pyridine, etc., and aromatic rings such as benzene, naphthalene, phenanthrene, etc., or aliphatic rings such as cyclopentane, cyclohexane, etc., are condensed to form a condensed ring, and in the case of a spiro compound, at least one ring contains a heteroatom, it is also a heterocyclic ring.

[0025] As used in this specification, the term "aliphatic ring" refers to a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes single rings, polycyclic rings, condensed rings, spiro compounds, etc. Unless otherwise stated, it refers to a ring having 3 to 60 carbon atoms, but is not limited thereto. In particular, in this specification, an aliphatic ring (group) is defined as a hydrocarbon ring that does not contain any aromatic rings. Therefore, not only saturated hydrocarbon rings such as cycloalkyl groups, but also cases where there is one or more double bonds within the ring are considered to correspond to an aliphatic ring if they are not aromatic hydrocarbons.

[0026] Unless otherwise specified, the terms “fusion ring(group)” or “condensation ring(group)” as used in this specification refer to a ring in which an aliphatic ring and an aromatic hydrocarbon (aromatic ring or aryl ring) are condensed together, and unless otherwise specified, refer to a ring in which an aliphatic ring having 3 to 60 carbon atoms and an aromatic hydrocarbon having 6 to 60 carbon atoms are condensed together.

[0027] In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be written as the 'name of the group reflecting the valence,' or it may be written as the 'name of the parent compound.' For example, in the case of 'phenanthrene,' a type of aryl group, the group name may be written by distinguishing the valence, such as 'phenanthrile' for the monovalent group and 'phenanthrillene' for the divalent group, but it may also be written as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be written as 'pyrimidine' regardless of the valence, or it may be written as the 'name of the group' corresponding to the valence, such as pyrimidinyl group for monovalent and pyrimidinyllene for divalent.

[0028] In addition, when describing compound names or substituent names in this specification, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofuro[2,3-d]pyrimidine as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzoquinoxaline.

[0029] In addition, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied identically to the definitions of substituents by the definitions of the indices of the following chemical formulas.

[0030]

[0031] Here, if a is an integer of 0, the substituent R 1≡ indicates absence; that is, when a is 0, it means that hydrogen is bonded to all carbons forming the benzene ring, in which case the chemical formula or compound can be written without indicating the hydrogen bonded to the carbons. Additionally, when a is an integer of 1, one substituent R 1 It bonds to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it can bond, for example, as follows; when a is an integer of 4 to 6, it bonds to the carbons of the benzene ring in a similar manner; and when a is an integer greater than or equal to 2, R 1 They may be the same or different from each other.

[0032]

[0033] In addition, unless otherwise stated in this specification, the term "ring" means an aryl ring, a heteroaryl ring, a fluorene ring, an aliphatic ring, a fused ring, etc., and terms such as "number-ring," "number-condensed ring," or "number-fused ring" mean a form in which rings corresponding to the number are fused together, and "number-ring" may mean a ring shape. For example, naphthalene corresponds to a 2-ring, a 2-condensed ring, or a 2-fused ring, anthracene corresponds to a 3-ring, a 3-condensed ring, or a 3-fused ring, thiophene or furan corresponds to a 5-membered heteroring, and benzene or pyridine corresponds to a 6-membered aromatic ring.

[0034] Additionally, unless otherwise described in this specification, the rings formed by combining adjacent groups are C6~C 60 Aromatic group of; fluorene group; C2~C containing at least one heteroatom among O, N, S, Si, P, Se, and Te 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C3~C 60 The aliphatic ring and C6~C 60The aromatic ring can be selected from a group of fused rings. Here, the aromatic ring can be an aryl ring, and the heteroring can include a heteroaryl ring.

[0035] Unless otherwise stated in this specification, the term "neighboring groups" includes, for example with the following chemical formula, R1 and R2, R2 and R3, R3 and R4, and R5 and R6, as well as R7 and R8 sharing one carbon, and may also include substituents bonded to non-immediately adjacent ring elements (such as carbon or nitrogen), such as R1 and R7, R1 and R8, or R4 and R5. That is, if there are substituents on immediately adjacent ring elements such as carbon or nitrogen, they may be neighboring groups; however, if no substituents are bonded to ring elements at immediately adjacent positions, they may be neighboring groups with substituents bonded to the next ring element, and substituents bonded to the same ring element may also be considered neighboring groups. In the following chemical formula, when substituents bonded to the same carbon, such as R7 and R8, bond to each other to form a ring, a compound containing a spiro moiety may be formed.

[0036]

[0037] Additionally, in this specification, the expression "neighboring units may combine to form a ring" is used with the same meaning as "neighboring units selectively combine to form a ring," and refers to the case where at least one pair of neighboring units combine to form a ring.

[0038] In addition, in this specification, the phrase "neighboring groups can combine with each other to form a ring" means that neighboring groups can consequently form a ring, and R 1 and R 2It is not assumed that the substituent contains an unsaturated bond, such as an alkenyl group or an alkyneyl group.

[0039] In addition, unless otherwise described in this specification, substituents such as aryl groups, arylene groups, fluorenyl groups, fluorenyl groups, heterocyclic groups, aliphatic cyclic groups, fused cyclic groups, alkyl groups, alkenyl groups, alkyneyl groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, etc., and rings formed by the bonding of adjacent groups are each deuterium; halogen; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group of; C6-C substituted with deuterium 30 aryl group of; C3-C 30 Aliphatic ring; C6-C 30 The aromatic ring and C3-C 30 A fused ring of an aliphatic ring; and a C2-C comprising at least one heteroatom among O, N, S, Si, P, Se, and Te. 30 It can be substituted with one or more substituents selected from a group of heterocyclic rings, adjacent substituents can bond to each other to form a ring, and the hydrogen of the substituents can be replaced with deuterium.

[0040] Unless otherwise explained in this specification, the mark "*" or " " indicates the connecting part.

[0041] Hereinafter, a compound according to one aspect of the present invention will be described.

[0042] A compound according to one aspect of the present invention is represented by the following chemical formula 1.

[0043] <Chemical Formula 1>

[0044]

[0045] <Chemical Formula A-1> <Chemical Formula A-2>

[0046]

[0047] In the above chemical formula 1, each symbol is defined as follows.

[0048] A is the chemical formula A-1.

[0049] X and Y are independently O, S, Se, or Te, preferably S.

[0050] Ar is C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si, Se, and Te 60 The heterocyclic group of; and N(R a )(R b It is selected from a group consisting of ).

[0051] L 1 and L 2 are independent single bonds; C6~C 60 arylene group; fluorenyllene group; C2~C comprising at least one heteroatom among O, N, S, Si, Se, and Te 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C3~C 60 The aliphatic ring and C6~C 60 It is selected from the group consisting of fused rings of aromatic rings. Preferably, L 1 and L 2 are independent single bonds; C6~C 60 arylene group of; and C2~C comprising at least one heteroatom among O, N, S, Si, Se and Te 60 It can be selected from a group consisting of heterocycles.

[0052] The B ring has the chemical formula A-2, and x is an integer from 0 to 3.

[0053] W 1 is CR' or N, provided that if x is 0, W 1 is N.

[0054] V 1 and V 2 are independently O, S, Se, Te, NR' or C(R')(R"), and when x is 2 or 3, multiple V 2 They are the same or different from each other.

[0055] When x is 0, chemical formula A-1 is V 1 and W 1 The 5-membered ring containing this and R 1 This substituted benzene ring may be in a directly condensed form, and when x is 1, the B ring may be a 5-membered heterocyclic ring represented by chemical formula A-2 or a single ring such as cyclopentadiene, when x is 2, the B ring may be a 2-membered heterocyclic ring formed by the condensation of two rings represented by chemical formula A-2 or dihydropentylene or a derivative thereof, and when x is 3, it may be in a form in which three of these 5-membered single rings are condensed.

[0056] For example, chemical formula A-2 may be a five-membered ring such as furan, thiophene, sellophen, telluropene, pyrrole or its derivatives, cyclopenta-1,3-diene and its derivatives, and ring B may be one of these rings, or a form in which two or three of these rings are condensed together. A form in which two of these rings are condensed together may be furofuran, thienothiophene, selenosellophene, telluropenetelluropene, thienofuran, selenophenofuran, furopyrrol, cyclopentafuran, sellophenothiophene, thienopyrrole, cyclopentathiophene, etc.

[0057] Chemical formula A-1 is x, V 1 , W 1 , R 1 The shape may vary depending on whether a ring is formed, etc.

[0058] For example, if x is 0, W 1 Only this N is possible. That is, when x is 0, V 1 and W 1 This contained 5-membered ring necessarily includes the heteroatom N, and becomes a 5-membered ring containing other heteroatoms O, S, Se, Te, or NR', or CR'R". Specifically, when x is 0, V 1 and W 1 The five-membered ring containing it can be oxazole, thiazole, selenaazole, tellurazole, imidazole and their derivatives, etc.

[0059] If x is 1 or 2, W 1 and V 1 Depending on the type of atoms, the structure of the five-membered ring containing them can vary, and W 1 If this CR'R" then V 1 Depending on the atoms, it can be furan, thiophene, celopene, telluropene, cyclopentadiene, and their derivatives, etc., and W 1 If this is N, then V 1 Depending on the atoms, it can be oxazole, thiazole, selenaazole, tellurazole, imidazole, and their derivatives.

[0060] In addition, since the above A is represented by the chemical formula A-1, V 1 , W 1 , B ring, R 1 The structure may vary depending on whether a ring is formed, etc. For example, if x is 0, W 1 This N, V 1 This O, V 2 Ga O, R 1 In the case of this hydrogen, it becomes a heterocyclic tricyclic ring or tricondensed ring formed by the sequential condensation of three rings of oxazole, furan, and benzene.

[0061] R 1 , R', R" independently of each other hydrogen; deuterium; halogen; cyano group; C6~C 60aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and Se 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 30 alkyl group of; C2~C 30 The Alken Diary of; C2~C 30 Alkin's Diary; C1~C 30 alkoxy groups; C6~C 30 The aryloxy group of; and L'-N(R a )(R b Selected from a group consisting of ), and neighboring R 1 They can combine with each other to form a ring, and R' and R" can combine with each other to form a ring.

[0062] a is an integer from 0 to 4, and if a is an integer greater than or equal to 2, multiple R 1 They are the same or different from each other.

[0063] Neighboring R 1 When they combine with each other to form a ring, the ring is C6~C 60 Aromatic ring; fluorene group; C3~C 60 an aliphatic ring of; C2~C comprising at least one heteroatom among O, N, S, Si, Se, and Te 60 heterocyclic; and C3~C 60 The aliphatic ring and C6~C 60 It can be selected from a group consisting of fused rings of aromatic rings.

[0064] Neighboring R 1 When they combine with each other to form an aromatic ring, the said aromatic ring is, for example, C6~C 20 , C6~C 18 , C6~C 16 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C10 , C6, C 10 , C 12 , C 14 , C 15 , C 16 , C 18 It can be an aromatic ring, specifically, benzene, naphthalene, phenanthrene, etc.

[0065] The above R a and R b C6-C are independently of each other 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom among O, N, S, Si, Se, and Te 30 heterocyclic; and C3-C 30 It is selected from a group consisting of aliphatic rings. Preferably, R a and R b C6-C are independently of each other 30 aryl group of; or C2-C comprising at least one heteroatom among O, N, S, Si, Se, and Te 30 It is a heterocyclic ring.

[0066] The above L' is a single bond; C6~C 60 arylene group; fluorenyllene group; C2~C comprising at least one heteroatom among O, N, S, Si, Se, and Te 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C3~C 60 The aliphatic ring and C6~C 60 It is selected from the group consisting of fused rings of aromatic rings. Preferably, L' is a single bond.

[0067] Ar, R a and R b At least one of them is an aryl group, or L 1 , L 2 Where at least one of them is an arylene group, said arylene group or arylene group is, for example, C6~C 30 , C6~C 29 , C6~C 28 , C6~C27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 , C 30 It may be an aryl group or an arylene group, and specifically, it may be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, benzophenanthrene, triphenylene, etc.

[0068] Ar, R a , R b , L 1 , L 2 Where at least one of them is a heterocyclic ring, the heterocyclic ring comprises, for example, a C2 to C2 atom comprising at least one heteroatom among O, N, S, Si, Se, and Te. 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26, C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 , C 30It may be a heterocyclic group such as pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silol, indene, indole, phenyl-indole, benzodole, phenyl-benzodole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenantroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dynaphthofuran, thiophene, benzothiophen, dibenzothiophen, naphthobenzothiophen, dynaphthothiophen, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, Naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzopuropyridine, benzothienopyridine, benzopuropyridine, benzothienopyrimidine, benzopuropyrimidine, benzothienopyrazine, benzopuropyrazine, benzimidazole, benzothiazole, benzoxazole, naphthoxazole, phenanthroxazole, benzocilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, cyanthrene, 9,9-dimethyl-9H-thioxanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, It may be spyro[fluorene-9,9'-xanthen], selonophene, benzocellonophene, dibenzocellonophene, or a combination thereof.

[0069] In particular, the above heterocyclic ring may be a heterocyclic ring comprising a five-membered ring such as thiophene, furan, selonophene, oxazole, thiazole, etc. For example, it may be a single ring of these five-membered rings, a heterocyclic ring in which two or more of these five-membered rings are condensed, a heterocyclic ring in which an aromatic ring is condensed to a single ring or condensed ring of these five-membered rings, or a heterocyclic ring in which an aliphatic ring is fused to a single ring or condensed ring of these five-membered rings. Specifically, thieno[3,2-b]thiophene, benzothiothiophene, selenocelopene, benzoselenoselonopene, furofuran, benzofurofuran, benzothiophene, benzoselophene, benzofuran, dibenzothiophene, dibenzoselophene, dibenzofuran, benzonaphthofuran, benzonaphthiophene, benzoxazole, benzothiazole, naphthoxazole, naphthiaazole, etc., or are heterocyclic rings condensed thereon into cyclopentadiene and its derivatives, indene or its derivatives, etc., or may be carbazole, phenylcarbazole, benzosilane, etc.

[0070] When Ar is a fluorene group, the fluorene group may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalene-2-yl)9-phenyl-9H-fluorene, etc.

[0071] The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, adjacent R 1 The rings formed by the bonding of R' and R" together, and the rings formed by the bonding of R' and R" together, are respectively deuterium; halogen; cyano group; and C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; C1-C 20alkoxy group of; C6-C 30 aryloxy group of; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom among O, N, S, Si, Se, and Te 60 heterocyclic; C3-C 30 Aliphatic ring; C3-C 30 The aliphatic ring and C6-C 30 A fused ring of an aromatic ring; and one or more substituents selected from the group consisting of combinations thereof, adjacent substituents may bond to each other to form a ring, and the hydrogen of the substituents may be replaced with deuterium.

[0072] The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, adjacent R 1 When at least one of the rings formed by the bonding of R' and R" is substituted with an aryl group, the aryl group is, for example, C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 , C 30 It could be an aril of the back.

[0073] The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, adjacent R 1 If at least one of the rings formed by the combination of R' and R" is substituted with a heterocyclic ring, the heterocyclic ring is, for example, C2~C 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26 , C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10, C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 , C 30 It can be a heterocyclic ring.

[0074] The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, adjacent R 1 When at least one of the rings formed by bonding together and the rings formed by bonding R' and R" together is substituted with an alkyl group, the alkyl group is, for example, C1 to C 20 , C1~C 10 It can be an alkyl group such as C1~C4, C1, C2, C3, C4, etc., and, for example, a methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, etc.

[0075] The above chemical formula A-1 can be represented by any one of the following chemical formulas A-1-1 to A-1-4.

[0076] <Chemical Formula A-1-1> <Chemical Formula A-1-2>

[0077]

[0078] <Chemical Formula A-1-3> <Chemical Formula A-1-4>

[0079]

[0080] In the above chemical formulas A-1-1 to A-1-4, V 1 , V 2 , W 1 , R 1 , a is the same as defined in chemical formula A-1, and V 3 and V 4 is V 2 It is the same as the definition of.

[0081] Specifically, the compound represented by the above chemical formula 1 may be one of the following compounds, but is not limited thereto.

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100] .

[0101] The compound represented by Formula 1 of the present invention is included in the active layer of an organic photovoltaic device. That is, the compound of Formula 1 of the present invention can be used as a compound for an organic photovoltaic device.

[0102] Hereinafter, an organic photovoltaic device comprising the compound of Formula 1 of the present invention will be described with reference to FIGS. 1 and 2.

[0103] FIGS. 1 and FIGS. 2 are drawings showing a stacked structure of an organic photovoltaic device according to an embodiment of the present invention.

[0104] It should be noted that when assigning reference numerals to the components of each drawing, the same components are assigned the same reference numeral whenever possible, even if they are shown in different drawings. Furthermore, in describing the present invention, if it is determined that a detailed description of related known components or functions could obscure the essence of the invention, such detailed description is omitted.

[0105] In describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc., may be used. These terms are intended merely to distinguish the components from other components, and the essence, order, or sequence of the components is not limited by these terms. Where it is stated that a component is "connected," "combined," or "joined" to another component, it should be understood that the component may be directly connected or joined to the other component, but that another component may also be "connected," "combined," or "joined" between each component.

[0106] Furthermore, when it is stated that a component, such as a layer, membrane, region, or plate, is "on" or "on" another component, this should be understood to include not only the case where it is "directly on" another component, but also the case where there is another component in between. Conversely, when it is stated that a component is "directly on" another part, it should be understood to mean that there is no other part in between.

[0107] Referring to FIG. 1, an organic photovoltaic device according to one embodiment of the present invention includes a first electrode (110), a second electrode (120), and an active layer (130) between the first electrode (110) and the second electrode (120). Referring to FIG. 2, the organic photovoltaic device may further include a hole transport band (210) between the first electrode (110) and the active layer (130) and an electron transport band (220) between the second electrode (120) and the active layer (130).

[0108] One of the first electrode (110) and the second electrode (120) is a negative electrode, and the other is a positive electrode. The positive electrode may be a permeable electrode. Typically, the material forming the permeable electrode may be selected from transparent conductive oxides (TCOs), such as indium tin oxide (ITO), zinc oxide (ZnO), tin oxide (SnO2), or indium zinc oxide (IZO) and combinations thereof, but is not limited thereto. The positive electrode may be formed as a multilayer comprising two or more layers.

[0109] The cathode is preferably composed of one or more metallic materials, and the metallic material may be selected from magnesium (Mg), silver (Ag), aluminum (Al), lithium (Li), calcium (Ca), indium (In), and combinations thereof, and preferably composed of a mixture of Mg and Ag, but is not limited thereto. The cathode may also be formed as a multilayer comprising two or more layers.

[0110] When light is introduced from the outside, the compound in the active layer (130) becomes excited by the photoelectric effect, and as a result, an exciton is generated. The holes and electrons of the exciton generated in this way are separated and move to the first electrode and the second electrode (120), respectively, thereby generating an electrical signal. For example, if the first electrode (110) is the positive electrode, holes move to the first electrode (110) and electrons move to the second electrode (120), thereby generating an electrical signal.

[0111] The active layer (130) may be formed as a single layer or a multilayer and may include two or more different compounds. The active layer (130) may include a p-type semiconductor compound and an n-type semiconductor compound, and thus a pn junction may be formed.

[0112] The compound represented by Formula 1 of the present invention is included in the active layer (130) and, preferably, can be applied as a p-type semiconductor compound of the active layer (130). In order for a pn junction to be formed in the active layer (130), the active layer (130) may further include an n-type semiconductor compound.

[0113] The n-type semiconductor compound may be a fullerene, a fullerene derivative, a compound represented by at least one of the following chemical formulas 30 to 33, or a mixture of these compounds, but this is merely an example of an n-type semiconductor compound and is not limited thereto.

[0114] The above fullerene is C 60 ~C 540 It can be composed of hydrocarbon rings. An example of the above fullerene is C 60 , C 70 , C 76 , C 78 , C 80 , C 82 , C 84 , C 90 , C 96 , C 240 , C 540There are mixtures of these, fullerene nanotubes, etc.

[0115] The above fullerene derivative refers to a compound having a substituent on the above fullerene. The above fullerene derivative is C1~C 30 alkyl group of, C6~C 30 aryl group of, C3~C 30 It may be a fullerene substituted with a substituent such as a heterocyclic group.

[0116] The above aryl group may be phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl, fluorenyl, triphenylenyl, naphthacenyl, etc., and the above heteroring may be pyrrole, furan, thiophene, imidazole, oxazole, thiazole, pyridine, pyrazine, pyrimidine, pyridazine, indolzine, indole, benzofuran, benzothiophene, isobenzofuran, benzimidazole, imidazopyridine, quinolizine, quinoline, phthalzine, naphthirizine, quinoxaline, quinazolin, isoquinoline, carbazole, phenatridine, acridine, phenanthroline, thiatene, cromen, xanthen, phenoxazine, phenoxatin, phenothiazine, or phenazine ring, etc., but is not limited thereto.

[0117] <Chemical Formula 30>

[0118]

[0119] In the above chemical formula 30, each symbol can be defined as follows.

[0120] R 31 to R 33 They are independently hydrogen; deuterium; halogen; cyano group; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C20 Alkin's Diary; C1~C 20 alkoxy groups; and C6~C 60 It is selected from a group consisting of aryloxy groups, and neighboring groups can bond with each other to form a ring.

[0121] a1, b1, and c1 are each integers from 1 to 3, and if they are integers greater than or equal to 2, R 31 Each, R 32 Each, R 33 Each is either the same or different from the others.

[0122] Z is a monovalent substituent and can be a halogen or a halogen-containing group, for example, F, Cl, an F-containing group or a Cl-containing group.

[0123] <Chemical Formula 31> <Chemical Formula 32>

[0124]

[0125] In the above chemical formulas 31 and 32, each symbol is defined as follows.

[0126] T 1 To T 3 can be a heterocyclic ring containing a thiophene group, and T 1 To T 3 Silver can combine with each other to form a ring.

[0127] X 10 To X 15 They are independently hydrogen; deuterium; halogen; cyano group; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 20alkoxy groups; and C6~C 60 It is selected from the group consisting of aryloxy groups.

[0128] EWG1 and EWG2 represent electron withdrawing groups. For example, X in Chemical Formula 31 above. 10 To X 15 At least one of them may be an electron absorber, and preferably may be a CN or CN-containing group.

[0129] <Chemical Formula 33>

[0130]

[0131] In the above chemical formula 33, each symbol is defined as follows.

[0132] Z 11 and Z 12 are independently N(R1), O, or S, and Y 11 to Y 14 is C(R2)(R3), O or S.

[0133] R 41 , R 42 , R1 to R3 are independently hydrogen; deuterium; halogen; cyano group; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 20 alkoxy groups; and C6~C 60 It is selected from a group consisting of aryloxy groups, and adjacent groups can bond with each other to form a ring, and R2 and R3 can also bond with each other to form a ring.

[0134] R2 and R3 may preferably be halogens or CN.

[0135] a2 and b2 are integers from 0 to 4, respectively, and x1 is an integer from 1 to 3.

[0136] In the above chemical formulas 30 to 33, the aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, and the ring formed by the bonding of adjacent groups are each deuterium; halogen; siloxane group; cyano group; nitro group; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P 24 heterocyclic; C3-C 30 aliphatic ring of; and C3-C 30 The aliphatic ring and C6-C 30 It can be substituted with one or more substituents selected from the group consisting of fused rings of the aromatic ring.

[0137] Specifically, the compound represented by the above chemical formula 33 may be one of the following compounds, but is not limited thereto.

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146] The compound represented by Chemical Formula 1 above is generally a compound that absorbs light in the visible light region, and has a maximum absorption wavelength (λ) of 600 nm or more in a thin film state max It is desirable to have ).

[0147] In particular, in the thin film state, it has a maximum absorption wavelength of 600 nm or more and 1300 nm or less. That is, the active layer (130) containing the compound also has a maximum absorption wavelength of 600 nm or more, preferably 600 nm to 1300 nm, and more preferably 800 nm to 1300 nm, as described above.

[0148] Accordingly, the active layer (130) can selectively absorb and / or detect light in the red or near-infrared wavelength region and may replace the color filter of the red or near-infrared pixel.

[0149] It is generally desirable for the compound represented by Chemical Formula 1 to have a small full width at half maximum (FWHM) of the absorption curve. A smaller FWHM implies that the selectivity of the wavelength of light absorbed by the compound is very high. In other words, a compound having a narrow FWHM can be considered a material with high selectivity and high sensitivity. Preferably, the FWHM of the active layer (130) containing the compound represented by Chemical Formula 1 is 50 nm to 300 nm.

[0150] When the compound represented by Chemical Formula 1 above is applied as a p-type semiconductor compound, it is desirable that the LUMO energy level be higher than that of the n-type semiconductor used in combination. The energy levels described below are expressed as absolute values. For example, when used in combination with an n-type material such as fullerene described below, since the LUMO energy level of fullerene is approximately 4.2 eV, it is desirable that the LUMO energy level of the compound represented by Chemical Formula 1 be 4.0 to 2.7 eV, which is higher than the LUMO energy level of fullerene.

[0151] In addition, since it is desirable for the energy bandgap to be 1.0 to 2.0 eV to absorb energy in the red or near-infrared wavelength region, it is desirable for the HOMO energy level of the compound represented by Chemical Formula 1 to be 4.7 to 6.5 eV.

[0152] When a compound represented by Chemical Formula 1 satisfying the above conditions is used in the active layer (130), it can have high External Quantum Efficiency (EQE) as a material that effectively absorbs light in the red or near-infrared wavelength region.

[0153] In addition, as described above, by including a compound represented by Chemical Formula 1 in the active layer (130), aggregation between compounds can be prevented even in a thin film state, thereby maintaining absorption characteristics according to wavelength, and thus, an organic photovoltaic device that selectively absorbs light of red or near-infrared wavelengths can be provided. In particular, in the case of light of wavelengths other than red or near-infrared, unnecessary absorption can be reduced, thereby providing a highly sensitive organic photovoltaic device.

[0154] The p-type semiconductor compound and the n-type semiconductor compound represented by the above chemical formula 1 may have a volume ratio of about 9:1 to about 1:9, preferably 1:3 to 1:5.

[0155] The ratio of p-type semiconductor compounds to n-type semiconductor compounds significantly affects the performance of organic optoelectronic devices. When the ratio of p-type to n-type semiconductor compounds is 1:1, approximately 6.0 x 10 4 cm -1 It can have an absorption coefficient greater than or equal to 6.0 x 10⁻⁶ 4 cm -1 Up to 1.0x10 5 cm -1 It is desirable to have an absorption coefficient of .

[0156] The active layer (130) containing a p-type semiconductor compound or an n-type semiconductor compound may be mixed with two or more compounds, but is not limited thereto.

[0157] Photoelectrically converted charge may not be fully utilized and may remain. If the residual charge is high, continuous light irradiation may be interrupted, causing the system to perceive that light is still being emitted due to the residual charge. Therefore, a high residual charge makes the device unsuitable as an image sensor. In other words, it is desirable to have a low residual charge, as a low residual charge is necessary to provide a high-sensitivity organic photovoltaic device.

[0158] To measure residual charge, light in a specific wavelength range is irradiated at a constant intensity for a certain period of time, and then the irradiation is stopped; the current flowing after the irradiation is stopped is then measured by integrating it over time.

[0159] An organic photovoltaic device can be fabricated by forming an active layer (130) through a high-temperature process such as vacuum deposition. Vacuum deposition has many process advantages, such as forming a uniform thin film and having a low possibility of impurity incorporation. However, the decomposition temperature (T) of the compound d ) is the deposition temperature (T sIf it is lower than ), the compound may be deposited along with decomposition products resulting from high temperature decomposition, which can impair the overall performance of the device. Therefore, it is desirable for the decomposition temperature of the compound to be higher than the deposition temperature.

[0160] That is, the deposition temperature (T s ) is the decomposition temperature (T d If the value is higher than ), decomposition occurs before sublimation (deposition), making it impossible to fabricate a normal device, and problems such as degradation of device performance occur, including the deposition of decomposed impurities.

[0161] Therefore, in order to manufacture a stable image sensor, the decomposition temperature (T d ) is the deposition temperature (T s It must be higher than ) and T d -T s It is desirable that it be ≥ 10℃.

[0162] In addition, when fabricating an image sensor, it is necessary to form a microlens array (MLA) after device fabrication to focus light, and forming the microlens array requires a high temperature (approximately 160°C to 190°C or higher). Therefore, the organic photovoltaic device must not degrade during the MLA heat treatment process.

[0163] In other words, degradation occurring in the MLA process does not refer to chemical decomposition but rather to changes in morphology, which generally occur as the vibrational motion of the material is initiated by heat treatment.

[0164] Therefore, if the molecular structure is designed to be robust, vibrational motion caused by heat is reduced, and deterioration due to heat treatment can be prevented. In the case of the compound represented by Chemical Formula 1 of the present invention, molecular vibration can be prevented by having a conjugated structure in the core, and as a result, process stability can be increased.

[0165] In addition, it is preferable that a compound represented by Chemical Formula 1 that can be stably deposited be used as the active layer (130) material, for example, a compound having a molecular weight of about 400 to 1000 g / mol, preferably 400 g / mol to 900 g / mol, more preferably 400 g / mol to 850 g / mol can be used in the deposition process.

[0166] When a compound represented by Chemical Formula 1 satisfying the above conditions is used in an organic photovoltaic device, a highly heat-resistant organic photovoltaic device suitable for high-temperature processes such as vacuum deposition can be manufactured.

[0167] The active layer (130) may have a thickness of 1 to 500 nm, preferably 5 to 400 nm. When formed with such a thickness, efficiency can be maximized by effectively absorbing light and effectively separating and transmitting holes and electrons. The thickness of the active layer (130) is determined according to the absorption coefficient of the active layer (130) material, and it is desirable to have a thickness capable of absorbing at least 70%, preferably 80%, and more preferably 90% of light.

[0168] Referring to FIG. 2, the organic photovoltaic device may further include a hole transport band (210) between the first electrode (110) and the active layer (130), and an electron transport band (220) between the second electrode (120) and the active layer (130).

[0169] By forming a hole transport band (210) and an electron transport band (220), the movement of holes and electrons separated in the active layer (130) can be made easier and faster, thereby increasing the efficiency of the organic photovoltaic device.

[0170] The above hole transport band (210) may include a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a hole transport assist layer, etc., and may include at least one hole transport layer.

[0171] The hole transport band (210) may include organic, inorganic, or organic-inorganic materials, and the organic material may be an organic compound having hole characteristics, but is not limited thereto.

[0172] The hole transport band (210) may include, for example, polymer compounds such as Poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) and polyarylamine, or organic compounds such as N,N,N',N'-tetrakis(4-methoxyphenyl)-benzidine (TPD), 4,4'-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (NPB), m-MTDATA, 4,4',4''-tris(N-carbazolyl)-triphenylamine (TCTA), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, but is not limited thereto.

[0173] For example, the hole transport band (210) may include an amine compound, specifically a compound represented by the following chemical formula 40 or chemical formula 41.

[0174] <Chemical Formula 40> <Chemical Formula 41>

[0175]

[0176] In the above chemical formulas 40 and 41, each symbol is defined as follows.

[0177] Ar 1 or Ar 7 C6~C are independent of each other 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60The aliphatic ring and C6~C 60 The fused ring of the aromatic ring; and C1~C 20 It is selected from the group consisting of alkyl groups.

[0178] L 1 to L 8 Single bonds independently of each other; C6~C 60 arylene group; fluorenyllene group; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 A fused ring of an aromatic ring; and C2~C comprising at least one heteroatom among O, N, S, Si, and P. 60 It is selected from a group consisting of heterocycles.

[0179] The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cycle, fused cycle, and alkyl group are, respectively, deuterium; halogen; siloxane group; cyano group; nitro group; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P 60 heterocyclic; C3-C 30 aliphatic ring of; and C3-C 30 The aliphatic ring and C6-C 30It can be substituted with one or more substituents selected from the group consisting of fused rings of the aromatic ring.

[0180] The above chemical formula 40 can be represented by one of the following chemical formulas 40-1 to 40-3.

[0181] <Chemical Formula 40-1> <Chemical Formula 40-2> <Chemical Formula 40-3>

[0182]

[0183] In the above chemical formulas 40-1 to 40-3, Ar 2 , Ar 3 , L 1 ~L 3 It is the same as defined in the above chemical formula 40.

[0184] X 21 and X 22 are independently single bonds, O, S, N(R 11 ), C(R 12 )(R 13 ) or Si(R 14 )(R 15 ) and cases where all are single bonds are excluded.

[0185] Ar a , R 11 to R 15 , R 51 to R 55 They are independently hydrogen; deuterium; halogen; cyano group; nitro group; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 20 alkoxy groups; and C6~C 60It is selected from a group consisting of aryloxy groups, and neighboring groups can bond with each other to form a ring.

[0186] Ar b is C3~C 60 The aliphatic ring of, preferably C3~C 60 It is a cycloalkyl group.

[0187] The above chemical formula 40-1 can be represented by the following chemical formula 40-1-1 or chemical formula 41-1-2.

[0188] <Chemical Formula 40-1-1> <Chemical Formula 40-1-2>

[0189]

[0190] In the above chemical formulas 40-1-1 and 40-1-2, Ar 2 , Ar 3 , L 1 ~L 3 , X 21 , R 51 , R 52 is equal to that defined in the above chemical formula 40-1, and R 56 and R 57 is R 12 and R 13 It is the same as the definition of.

[0191] In the above chemical formula 40-3, Ar b It may be selected from the following chemical formula structures, but is not limited thereto.

[0192]

[0193] In the above chemical formula structure, Z 11 Hydrogen; Deuterium; Halogen; Siloxane group; Cyano group; Nitro group; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; C1-C 20 alkylthio group of; C1-C 20alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P 60 heterocyclic; C3-C 30 aliphatic ring of; and C3-C 30 The aliphatic ring and C6-C 30 It is selected from a group consisting of fused rings of aromatic rings, and adjacent groups can combine with each other to form aliphatic rings. z1 and z2 are integers from 0 to 11, and z3 is an integer from 0 to 15.

[0194] The above chemical formula 41 can be represented by the following chemical formula 41-1 or chemical formula 41-2.

[0195] <Chemical Formula 41-1> <Chemical Formula 41-2>

[0196]

[0197] In the above chemical formulas 41-1 and 41-2, Ar 4 or Ar 7 , L 4 to L 7 It is the same as defined in the above chemical formula 41.

[0198] R 71 to R 73 Hydrogen; deuterium; halogen; siloxane group; cyano group; nitro group; C1-C independently 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; C1-C 20 alkylthio group of; C1-C 20alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P 60 heterocyclic; C3-C 30 aliphatic ring of; and C3-C 30 The aliphatic ring and C6-C 30 It is selected from a group consisting of fused rings of aromatic rings, and adjacent groups can combine with each other to form aliphatic rings. n4, b', and c' are integers from 1 to 3, respectively.

[0199] The above chemical formula 41-1 can be represented by the following chemical formula 41-1-1 or chemical formula 41-1-2.

[0200] <Chemical Formula 42-1-1> <Chemical Formula 42-1-2>

[0201]

[0202] In the above chemical formulas 41-1-1 and 41-1-2, Ar 4 or Ar 7 , L 4 to L 7 It is the same as defined in the above chemical formula 41-1.

[0203] X 31 is O, S, N(R 21 ) or C(R 22 )(R 22 )am.

[0204] R 74 to R 77 , R 21 to R 23 Hydrogen; deuterium; halogen; siloxane group; cyano group; nitro group; C1-C independently 20 alkyl group or C6-C 20Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P 60 heterocyclic; C3-C 30 aliphatic ring of; and C3-C 30 The aliphatic ring and C6-C 30 It is selected from a group consisting of fused rings of aromatic rings, and adjacent groups can combine with each other to form rings. d' and e' are integers from 1 to 3, f' is an integer from 1 to 4, and g' is an integer from 1 to 2.

[0205] Specifically, the compound represented by the above chemical formula 40 may be one of the following compounds P1-1 to P1-49, P1-89 and P1-90, and the compound represented by the above chemical formula 41 may be one of the following compounds P1-50 to P1-88, but is not limited thereto.

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229] The electron transport band (220) may include an electron injection layer (EIL), an electron transport layer (ETL), a hole blocking layer (HBL), an electron transport assist layer, etc., and may include at least one electron transport layer.

[0230] The electron transport band (220) may include organic, inorganic, and organic-inorganic materials, and the organic material may be an organic compound having electronic properties, and the inorganic material may be molybdenum oxide, tungsten oxide, nickel oxide, lithium halide, etc., but is not limited thereto.

[0231] The electron transport band (220) may include organic compounds and organometallic compounds such as 1,4,5,8-Naphthalene-tetracarboxylic dianhydride (NTCDA), bath ℃uproine (BCP), LiF, Alq3, Gaq3, Inq3, Znq2, Zn(BTZ)2, BeBq2, etc., but is not limited thereto.

[0232] For example, the electron transport band (220) may include an azine compound, specifically a compound represented by the following chemical formula 50 or chemical formula 51.

[0233] <Chemical Formula 50> <Chemical Formula 51>

[0234]

[0235] In the above chemical formulas 50 and 51, each symbol is defined as follows.

[0236] X a To X c are independently N or C(R 51 ) and at least one is N. Therefore, X a To X c The containing ring may be pyridine, pyrimidine, or triazine.

[0237] X d is O, S or N(R 52 )am.

[0238] Ar 10 or Ar 13 C6~C are independent of each other 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 The fused ring of the aromatic ring; and C1~C 30 It is selected from the group consisting of alkyl groups.

[0239] L 10 to L 13 is a single bond; C6~C 60 arylene group; fluorenyllene group; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 A fused ring of an aromatic ring; and C2~C comprising at least one heteroatom among O, N, S, Si, and P. 60 It is selected from a group consisting of heterocycles.

[0240] R 100 , R 51 and R 52 are independently hydrogen; deuterium; halogen; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 30 alkyl group of; C2~C 30 The Alken Diary of; C2~C 30 Alkin's Diary; C1~C 30 alkoxy groups; and C6~C 30 It is selected from the group consisting of aryloxy groups, and neighboring groups can bond with each other to form a ring. q is an integer from 1 to 4.

[0241] The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cycle, fused cycle, alkyl group, alkenyl group, alkyneyl group, alkoxy group, and aryloxy group are each deuterium; halogen; siloxane group; cyano group; nitro group; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; C1-C 20alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P 60 heterocyclic; C3-C 30 aliphatic ring of; and C3-C 30 The aliphatic ring and C6-C 30 It can be substituted with one or more substituents selected from the group consisting of fused rings of the aromatic ring.

[0242] The above chemical formula 50 can be represented by one of the following chemical formulas 50-1 to 50-3.

[0243] <Chemical Formula 50-1> <Chemical Formula 50-2>

[0244]

[0245] <Chemical Formula 50-3>

[0246]

[0247] In the above chemical formulas 50-1 to 50-3, X a To X c , Ar 11 , Ar 12 , L 10 to L 12 is the same as defined in the above chemical formula 50.

[0248] X 31 and X 32 are independently single bonds, O, S, N(R 53 ), C( 54 )(R 55 ) or Si(R 56 )(R 57 ) and cases where all are single bonds are excluded.

[0249] Ar 14 , R 80 to R 84 , R 53 to R 57 They are independently hydrogen; deuterium; halogen; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 30 alkyl group of; C2~C 30 The Alken Diary of; C2~C 30 Alkin's Diary; C1~C 30 alkoxyl groups of; and C6~C 30 It is selected from a group consisting of aryloxy groups, and neighboring groups can bond with each other to form a ring.

[0250] a5, c5, d5 and e5 are integers from 1 to 4, respectively, and b5 is an integer from 0 to 3.

[0251] Ar 15 C6~C 60 It is an aryl group, and a6 is an integer greater than or equal to 1.

[0252] The above chemical formula 50-1 can be represented by the following chemical formula 50-1-1 or chemical formula 50-1-2.

[0253] <Chemical Formula 50-1-1> <Chemical Formula 50-1-2>

[0254]

[0255] In the above chemical formulas 50-1-1 and 50-1-2, X a To X c , Ar 11 , Ar 12 , L 10 to L 12 is, X 31 , R 80 , R81 , a5, and b5 are as defined in the above chemical formula 50-1, and R 101 and R 102 is R 54 and R 55 It is the same as.

[0256] Specifically, the compound represented by the above chemical formula 50 may be one of the following compounds P2-1 to P2-48, and the compound represented by the above chemical formula 51 may be one of the following compounds P2-49 to P2-76, but is not limited thereto.

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276] An organic photovoltaic device according to one embodiment of the present invention can be manufactured using various deposition methods. The organic photovoltaic device can be manufactured using deposition methods such as PVD or CVD, for example, by forming a first electrode (110) by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, forming an organic layer including an active layer (130) thereon, and then depositing a material that can be used as a second electrode (120) thereon.

[0277] Additionally, the active layer (130) can be manufactured in fewer layers by using various polymer materials and by a solution process or solvent process other than a deposition method, such as a spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading process, screen printing process, or thermionic method.

[0278] An organic photovoltaic device according to one embodiment of the present invention can be applied to organic solar cells, image sensors, photodetectors, light sensors, and organic light-emitting devices, etc. In particular, the organic photovoltaic device of the present invention can be applied to image sensors, etc.

[0279] The image sensor including the above organic photovoltaic element may be an image sensor capable of detecting light of 650 nm or greater, and preferably capable of detecting light of wavelengths from 650 to 1300 nm. Accordingly, it may selectively detect light in the red or near-infrared wavelength region and may replace the color filter of the red or near-infrared pixel.

[0280] Another embodiment of the present invention may include an electronic device comprising the image sensor of the present invention described above. In this case, the electronic device may be a current or future wired or wireless communication terminal, and may include all electronic devices such as mobile communication terminals such as mobile phones, navigation systems, game consoles, various TVs, various computers, digital cameras, electronic endoscopes, etc.

[0281] The present invention will be described in detail below with reference to examples. The following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by these examples.

[0282] [Synthetic Example]

[0283] The compound (final product) represented by Chemical Formula 1 according to the present invention can be prepared by the following Reaction Formula 1, but is not limited thereto.

[0284] <Reaction Equation 1>

[0285]

[0286] 1. Specific compounds of Sub A

[0287] Compounds belonging to Sub A may be the following compounds, but are not limited thereto, and the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the following compounds are as shown in Table 1.

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302] 화합물FD-MS화합물FD-MSSub A-1m / z=349.79 (C6Br2N4S2=352.02)Sub A-2m / z=541.85 (C 20 H7BrN4S5=543.51)Sub A-3m / z=459.86 (C 16 H5BrN4S4=461.39)Sub A-4m / z=469.93 (C 19 H 11 BrN4S3=471.41)Sub A-5m / z=485.87 (C 18 H7BrN4S4=487.43)Sub A-6m / z=518.93 (C 22 H 10 BrN5S3=520.44)Sub A-7m / z=512.97 (C 24 H 12 BrN5S2=514.42)Sub A-8m / z=463.98 (C 21 H 13 BrN4S2=465.39)Sub A-9m / z=503.92 (C 22 H9BrN4S3=505.43)Sub A-10m / z=605.76 (C 20 H7BrN4S2Se2=605.27)Sub A-11m / z=485.87 (C 18 H7BrN4S4=487.43)Sub A-12m / z=464.94 (C 19 H8BrN5OS2=466.33)Sub A-13m / z=464.94 (C 19 H8BrN5OS2=466.33)Sub A-14m / z=571.95 (C 25 H13 BrN6S3=573.50)Sub A-15m / z=454.90 (C 17 H6BrN5S3=456.35)Sub A-16m / z=438.92 (C 17 H6BrN5OS2=440.29)Sub A-17m / z=545.96 (C 25 H 15 BrN4S3=547.51)Sub A-18m / z=525.90 (C 21 H 11 BrN4S4=527.49)Sub A-19m / z=574.90 (C 24 H 10 BrN5S4= 576.52)Sub A-20m / z=479.97 (C 21 H 13 BrN4OS2= 481.39)Sub A-21m / z=632.89 (C 26 H 12 BrN5S5=634.62)Sub A-22m / z=616.95 (C 27 H 16 BrN5S4=618.60)Sub A-23m / z=568.94 (C 26 H 12 BrN5S3=570.50)Sub A-24m / z=611.96 (C 28 H 17 BrN4S3Si=613.64)Sub A-25m / z=501.85 (C 18 H7BrN4S2Se=502.28)Sub A-26m / z=585.90 (C 26 H 11 BrN4S4=587.55)Sub A-27m / z=608.86 (C 24 H 12 BrN5Se2=608.24)Sub A-28m / z=388.90 (C 13 H4BrN5OS2=390.23)Sub A-29m / z=403.89 (C 14 H5BrN4S3=405.31)Sub A-30m / z=559.89 (C 24 H9BrN4S4=561.51)Sub A-31m / z=515.83 (C 18H5BrN4S5=517.47)Sub A-32m / z=509.87 (C 20 H7BrN4S4=511.45)Sub A-33m / z=509.87 (C 20 H7BrN4S4=511.45)Sub A-34m / z=479.92 (C 20 H9BrN4S3=481.40)Sub A-35m / z=529.93 (C 24 H 11 BrN4S3=531.46)Sub A-36m / z=561.90 (C 24 H 11 BrN4S4=563.52)Sub A-37m / z=479.92 (C 20 H9BrN4S3=481.40)Sub A-38m / z=529.93 (C 24 H 11 BrN4S3=531.46)Sub A-39m / z=530.93 (C 23 H 10 BrN5S3=532.45)Sub A-40m / z=542.84 (C 19 H6BrN5S5=544.50)

[0303] 2. Specific Compounds of Sub B The compounds belonging to Sub B may be the following compounds, but are not limited thereto, and the FD-MS values ​​of the following compounds are as shown in Table 2.

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314] 화합물FD-MS화합물FD-MSSub B-1m / z=245.12 (C 13 H 16 BNO3=245.09)Sub B-2m / z=327.11 (C 17 H 18 BNO3S=327.20)Sub B-3m / z=311.13 (C 17 H 18 BNO4=311.14)Sub B-4m / z=295.14 (C 17 H 18 BNO3=295.14)Sub B-5m / z=343.09 (C 17 H 18 BNO2S2=343.27)Sub B-6m / z=393.10 (C 21 H 20 BNO2S2=393.33)Sub B-7m / z=345.15 (C 21 H 20 BNO3=345.21)Sub B-8m / z=321.15 (C 19 H 20 BNO3=321.18)Sub B-9m / z=377.13 (C 21 H 20 BNO3S=377.27)Sub B-10m / z=428.17 (C 25 H 25 BN2O2S=428.36)Sub B-11m / z=428.17 (C 25 H 25 BN2O2S=428.36)Sub B-12m / z=233.07 (C 11 H 12 BNO2S=233.09)Sub B-13m / z=311.12 (C 17 H 18 BNO2S=311.21)Sub B-14m / z=393.10 (C 21 H 20 BNO2S2=393.33)Sub B-15m / z=371.17 (C 23 H 22NOS3=371.24)Sub B-16m / z=393.10 (C 21 H 20 BNO2S2=393.33)Sub B-17m / z=362.14 (C 20 H 19 BN2O4=362.19)Sub B-18m / z=311.12 (C 17 H 18 BNO2S=311.21)Sub B-19m / z=361.13 (C 21 H 20 BNO2S=361.27)Sub B-20m / z=345.15 (C 21 H 20 NOS3=345.21)Sub B-21m / z=371.17 (C 23 H 22 NOS3=371.24)Sub B-22m / z=383.08 (C 19 H 18 BNO3S2=383.29)Sub B-23m / z=295.14 (C 17 H 18 NO3=295.14)Sub B-24m / z=371.17 (C 23 H 22 NOS3=371.24)Sub B-25m / z=295.14 (C 17 H 18 NOS3=295.14)Sub B-26m / z=377.13 (C 21 H 20 BNO3S=377.27)Sub B-27m / z=371.17 (C 23 H 22 NOS3=371.24)Sub B-28m / z=387.15 (C 23 H 22 BNO2S=387.30)Sub B-29m / z=399.06 (C 19 H 18 BNO2S3=399.35)

[0315] 3. 최종 화합물의 합성예

[0316] P5 합성예시

[0317]

[0318]

[0319] (1) Sub A-3-a synthesis

[0320] Sub A-3-a-1 (70.0 g, 260.1 mmol), Bis(pinacolato)diboron (85.9 g, 338.1 mmol), KOAc (51.1 g, 520.1 mmol), Pd(dppf)Cl2 (5.71 g, 7.80 mmol), and Toluene (850 mL) were added to a round-bottom flask and stirred at 100 °C. Once the reaction was complete, water was added and the mixture was extracted with MC (methylene chloride). Subsequently, the organic layer was dried with MgSO4 and concentrated. The concentrate was separated using a silica gel column and recrystallized to obtain 72.86 g of product (yield: 92.3%).

[0321] (2) Sub A-3 Synthesis

[0322] Sub A-3-a (71.9 g, 227.3 mmol), Sub A-1 (80.0 g, 227.3 mmol), K2CO3 (62.8 g, 454.5 mmol), Pd(PPh3)4 (7.88 g, 6.818 mmol), Toluene (570 mL), H2O (190 mL), and EtOH (19 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, water was added and extracted with MC. Subsequently, the organic layer was dried with MgSO4 and concentrated, and the concentrate was separated using a silica gel column and recrystallized to obtain 60.18 g of product (yield: 57.4%).

[0323] (3) Sub B-5-a synthesis

[0324] Sub B-5-a-1 (70.0 g, 327.0 mmol), Bis(pinacolato)diboron (107.9 g, 425.1 mmol), KOAc (64.18 g, 654.0 mmol), Pd(dppf)Cl2 (7.18 g, 9.81 mmol), and Toluene (1000 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, water was added and extracted with MC. Subsequently, the organic layer was dried with MgSO4 and concentrated, and the concentrate was separated using a silica gel column and recrystallized to obtain 69.89 g of product (yield: 81.8%).

[0325] (4) Sub B-5-b synthesis

[0326] Sub B-5-a (66.1 g, 253.2 mmol), Sub B-5-a-2 (50.0 g, 253.2 mmol), K2CO3 (70.0 g, 506.4 mmol), Pd(PPh3)4 (8.78 g, 7.60 mmol), Toluene (630 mL), H2O (150 mL), and EtOH (15 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 52.37 g of product (yield: 82.1%).

[0327] (5) Sub B-5 Synthesis

[0328] Sub B-5-b (50.0 g, 198.6 mmol), Bis(pinacolato)diboron (65.6 g, 258.2 mmol), KOAc (39.0 g, 397.2 mmol), Pd(dba2)Cl3 (5.46 g, 5.96 mmol), Xphos (11.36 g, 11.92 mmol), and Toluene (660 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, water was added and extracted with MC. Subsequently, the organic layer was dried with MgSO4 and concentrated, and the concentrate was separated using a silica gel column and recrystallized to obtain 60.76 g of product (yield: 89.1%).

[0329] (6) P5 synthesis

[0330] Sub A-5 (50.0 g, 108.4 mmol), Sub B-5 (37.2 g, 108.4 mmol), NaOH (30.0 g, 216.7 mmol), Pd(PPh3)4 (3.76 g, 3.25 mmol), Toluene (270 mL), and H2O (90 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 52.34 g of product (yield: 80.8%).

[0331] P22 Synthesis Example

[0332]

[0333] Sub A-1 (50.0 g, 142.0 mmol), Sub B-5 (48.75 g, 142.0 mmol), NaOH (39.3 g, 284.1 mmol), Pd(PPh3)4 (4.92 g, 4.26 mmol), Toluene (350 mL), and H2O (90 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 77.05 g of product (yield: 88.7%).

[0334] P26 Synthesis Example

[0335]

[0336]

[0337] (1) Sub A-18-a synthesis

[0338] Sub A-18-a-1 (50.0 g, 192.19 mmol), Sub A-18-a-2 (42.49 g, 192.19 mmol), K2CO3 (79.69 g, 576.57 mmol), Pd(PPh3)4 (6.66 g, 5.77 mmol), Toluene (480 mL), H2O (192 mL), and EtOH (48 mL) were added to a round-bottom flask and reacted. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 41.65 g of product (yield: 79%).

[0339] (2) Sub A-18-b synthesis

[0340] Sub A-18-a (40 g, 145.80 mmol) and THF (729 mL) were placed in a round-bottom flask and stirred. At 5 °C, 3 M methylmagnesium chloride solution (194.40 mL) was slowly added dropwise to the reaction mixture and stirred for 1 hour. Once the reaction was complete, the product was slowly poured into ice water, extracted with MC, and the organic layer was dried with MgSO4 and concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 36.81 g of product (yield: 92%).

[0341] (3) Sub A-18-c synthesis

[0342] Sub A-18-b (35 g, 127.55 mmol) dissolved in toluene (425 mL) was slowly added dropwise to a suspension of polyphosphoric acid (144.84 g, 1020.41 mmol) and methanesulfonic acid (66.26 mL, 1020.41 mmol), and the mixture was stirred for 24 hours. Once the reaction was complete, the product was poured into ice water and neutralized with a 10% aqueous NaOH solution. Subsequently, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. The concentrate was then separated using a silica gel column and recrystallized to obtain 20.93 g of product (yield: 64%).

[0343] (4) Sub A-18-d synthesis

[0344] Sub A-18-c (20 g, 78.00 mmol) was added to DMF, and N-Bromosuccinimide (13.88 g, 78.01 mmol) was added dropwise at -10 ℃. After stirring at room temperature for 6 hours, water was added and the mixture was extracted with MC once the reaction was complete. The organic layer was dried with MgSO4 and concentrated, and the resulting concentrate was recrystallized with toluene to obtain 20.45 g of product (yield: 78.2%).

[0345] (5) Sub A-18-e synthesis

[0346] Sub A-18-d (20.0 g, 59.65 mmol), Bis(pinacolato)diboron (19.7 g, 77.54 mmol), KOAc (11.71 g, 119.3 mmol), Pd(dppf)Cl2 (1.31 g, 1.79 mmol), and Toluene (200 mL) were added to a round-bottom flask and stirred at 100 °C. Once the reaction was complete, water was added and the mixture was extracted with MC (methylene chloride). Subsequently, the organic layer was dried with MgSO4 and concentrated. The concentrate was separated using a silica gel column and recrystallized to obtain 19.21 g of product (yield: 84.2%).

[0347] (6) Sub A-18 Synthesis

[0348] Sub A-18-e (18.5 g, 48.3 mmol), Sub A-1 (17 g, 48.3 mmol), K2CO3 (13.3 g, 96.6 mmol), Pd(PPh3)4 (1.67 g, 1.449 mmol), Toluene (120 mL), H2O (30 mL), and EtOH (3 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 10.92 g of product (yield: 42.9%).

[0349] (7) P26 synthesis

[0350] Sub A-18 (10.0 g, 18.95 mmol), Sub B-5 (6.50 g, 18.95 mmol), NaOH (5.24 g, 37.89 mmol), Pd(PPh3)4 (0.66 g, 0.57 mmol), Toluene (50 mL), and H2O (13 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 8.54 g of product (yield: 73.7%).

[0351] P34 Synthesis Example

[0352]

[0353]

[0354] (1) Sub B-8-a synthesis

[0355] Sub B-8-a-1 (70.0 g, 303.0 mmol), Bis(pinacolato)diboron (100.0 g, 393.9 mmol), KOAc (59.5 g, 606.0 mmol), Pd(dppf)Cl2 (6.65 g, 9.09 mmol), and Toluene (1000 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, water was added and extracted with MC (methylene chloride). Subsequently, the organic layer was dried with MgSO4 and concentrated, and the concentrate was separated using a silica gel column and recrystallized to obtain 67.22 g of product (yield: 90.5%).

[0356] (2) Sub B-8-b synthesis

[0357] Sub B-8-a (60.0 g, 244.8 mmol), Sub B-8-a-2 (48.4 g, 244.8 mmol), K2CO3 (67.7 g, 489.6 mmol), Pd(PPh3)4 (8.49 g, 7.34 mmol), Toluene (600 mL), H2O (150 mL), and EtOH (15 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 48.36 g of product (yield: 83.8%).

[0358] (3) Sub B-8 synthesis

[0359] Sub B-8-b (45.0 g, 190.9 mmol), Bis(pinacolato)diboron (63.0 g, 248.2 mmol), KOAc (37.5 g, 381.9 mmol), Pd(dba2)Cl3 (5.25 g, 5.73 mmol), Xphos (10.93 g, 11.46 mmol), and Toluene (630 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, water was added and extracted with MC (methylene chloride). Subsequently, the organic layer was dried with MgSO4 and concentrated, and the concentrate was separated using a silica gel column and recrystallized to obtain 51.54 g of product (yield: 82.50).

[0360] (4) Sub A-25-a synthesis

[0361] Sub A-25-a-1 (60.0 g, 225.9 mmol), Bis(pinacolato)diboron (74.6 g, 297.7 mmol), KOAc (44.3 g, 451.8 mmol), Pd(dba2)Cl3 (6.21 g, 6.78 mmol), Xphos (12.92 g, 13.55 mmol), and Toluene (750 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, water was added and extracted with MC (methylene chloride). Subsequently, the organic layer was dried with MgSO4 and concentrated, and the concentrate was separated using a silica gel column and recrystallized to obtain 62.46 g of product (yield: 80.8%).

[0362] (5) Sub A-25 Synthesis

[0363] Sub A-25-a (50.0 g, 142.0 mmol), Sub A-1 (48.6 g, 142.0 mmol), K2CO3 (39.3 g, 284.1 mmol), Pd(PPh3)4 (4.92 g, 4.26 mmol), Toluene (350 mL), H2O (80 mL), and EtOH (8 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 52.54 g of product (yield: 73.64%).

[0364] (6) P34 synthesis

[0365] Sub A-25 (50.0 g, 99.55 mmol), Sub B-8 (32.57 g, 99.55 mmol), NaOH (27.5 g, 199.1 mmol), Pd(PPh3)4 (3.45 g, 2.99 mmol), Toluene (250 mL), and H2O (60 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 51.38 g of product (yield: 82.9%).

[0366] P51 Synthesis Example

[0367]

[0368]

[0369] (1) Sub B-29-a synthesis

[0370] Sub B-29-a-1 (70.0 g, 327.0 mmol), Bis(pinacolato)diboron (107.9 g, 425.1 mmol), KOAc (64.18 g, 654.0 mmol), Pd(dppf)Cl2 (7.18 g, 9.81 mmol), and Toluene (1000 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, water was added and extracted with MC (methylene chloride). Subsequently, the organic layer was dried with MgSO4 and concentrated, and the concentrate was separated using a silica gel column and recrystallized to obtain 69.89 g of product (yield: 81.8%).

[0371] (2) Sub B-29-b synthesis

[0372] Sub B-29-a (60.0 g, 236.6 mmol), Sub B-29-a-2 (61.8 g, 236.6 mmol), K2CO3 (65.4 g, 473.3 mmol), Pd(PPh3)4 (8.20 g, 7.10 mmol), Toluene (600 mL), H2O (150 mL), and EtOH (15 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 58.93 g of product (yield: 80.9%).

[0373] (3) Sub B-29 synthesis

[0374] Sub B-29-b (50.0 g, 162.4 mmol), Bis(pinacolato)diboron (53.6 g, 211.2 mmol), KOAc (31.9 g, 324.9 mmol), Pd(dba2) (4.46 g, 4.88 mmol), Xphos (9.29 g, 9.75 mmol), and Toluene (550 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, water was added and extracted with MC (methylene chloride). Subsequently, the organic layer was dried with MgSO4 and concentrated, and the concentrate was separated using a silica gel column and recrystallized to obtain 46.35 g of product (yield: 71.46%).

[0375] (4) P51 synthesis

[0376] Sub A-1 (40.0 g, 113.6 mmol), Sub B-29 (45.4 g, 113.6 mmol), NaOH (31.4 g, 227.3 mmol), Pd(PPh3)4 (3.94 g, 3.41 mmol), Toluene (280 mL), and H2O (70 mL) were added to a round-bottom flask and stirred at 100 °C. After the reaction was complete, the mixture was extracted with MC, the organic layer was dried with MgSO4, and the mixture was concentrated. Subsequently, the concentrate was separated using a silica gel column and recrystallized to obtain 67.83 g of product (yield: 81.0%).

[0377] The FD-MS values ​​of compounds P1 to P54 of the present invention prepared according to the synthesis example above are as shown in Table 3 below.

[0378] Compound FD-MS Compound FD-MSP1 m / z=580.96 (C 27 H 11 N5OS5=581.72)P2m / z=580.96 (C 27 H 11 N5OS5=581.72)P3m / z=575.05 ( C 30 H 17 N5O2S3=575.68)P4m / z=575.00 (C 29 H 13N5OS4=575.70)P5m / z=596.93 (C 27 H 11 N5S6=597.78)P6m / z=607.01 (C 30 H 17 N5S5=607.80)P7m / z=640.03 (C 33 H 16 N6OS4=640.77)P8m / z=700.06 (C 39 H 20 N6S4=700.87)P9m / z=601.05 (C 32 H 19 N5S4=601.78)P10m / z=658.07 (C 37 H 18 N6OS3=658.77)P11m / z=691.01 (C 37 H 17 N5S5=691.88)P12m / z=742.84 (C 31 H 13 N5S4Se2=741.66)P13m / z=601.02 (C 31 H 15 N5OS4=601.74)P14m / z=652.03 (C 34 H 16 N6OS4=652.78)P15m / z=636.05 (C 34 H 16 N6O2S3=636.72)P16m / z=723.98 (C 36 H 16 N6S6=724.93)P17m / z=794.12 (C 44 H 26 N8S4=794.99)P18m / z=627.04 (C 32 H 17 N7S4=627.78)P19m / z=459.97 (C 20 H8N6S4=460.57)P20m / z=560.00 (C 28 H 12 N6S4=560.69)P21m / z=528.05 (C 28 H 12 N6O2S2=528.56)P22m / z=623.94 (C 28 H 12N6S6=624.81)P23m / z=723.98 (C 36 H 16 N6S6=724.93)P24m / z=680.11 (C 40 H 20 N6O2S2=680.76)P25m / z=683.04 (C 36 H 21 N5S5=683.90)P26m / z=662.98 (C 32 H 17 N5S6=663.88)P27m / z=657.02 (C 34 H 19 N5S5=657.86)P28m / z=696.00 (C 35 H 16 N6OS5=696.85)P29m / z=601.07 (C 32 H 19 N5O2S3=601.72)P30m / z=672.00 (C 33 H 16 N6OS5=672.83)P31m / z=738.05 (C 38 H 22 N6OS5=738.93)P32m / z=706.02 (C 37 H 18 N6S5=706.89)P33m / z=651.07 (C 35 H 21 N5OS3Si=651.85)P34m / z=622.94 (C 29 H 13 N5OS3Se=622.61)P35m / z=722.98 (C 37 H 17 N5S6=723.94)P36m / z=729.96 (C 35 H 18 N6OSSe2=728.57)P37m / z=545.04 (C 27 H 11 N7O3S2=545.55)P38m / z=590.98 (C 29 H 13 N5S5=591.76)P39m / z=559.01 (C 29 H 13 N5S4=559.70)P40m / z=675.03 (C 37 H17 N5OS4=675.82)P41m / z=620.93 (C 29 H 11 N5S6=621.80)P42m / z=649.02 (C 35 H 15 N5OS4=649.78)P43m / z=675.03 (C 37 H 17 N5OS4=675.82)P44m / z=662.94 (C 31 H 13 N5OS6=663.84)P45m / z=569.04 (C 31 H 15 N5OS3=569.67)P46m / z=695.09 (C 41 H 21 N5OS3=695.83)P47m / z=651.03 (C 35 H 17 N5OS4=651.80)P48m / z=651.03 (C 35 H 17 N5OS4=651.80)P49m / z=695.09 (C 41 H 21 N5OS3=695.83)P50m / z=712.06 (C 40 H 20 N6S4=712.88)P51m / z=735.89 (C 32 H 12 N6S8=736.97)P52m / z=794.98 (C 40 H 21 N5S7=796.06)P53m / z=785.00 (C 39 H 23 N5S7=786.07)P54m / z=794.98 (C 40 H 21 N5S7=796.06)

[0379] Although synthetic examples of the present invention represented by Chemical Formula 1 have been described above, they are all based on Suzuki cross-coupling reactions, Miyaura boration reactions, PPh3-mediated reductive cyclization reactions (J. Org. Chem. 2005, 70, 5014), Buchwald-Hartwig cross-coupling reactions, etc., and those skilled in the art will easily understand that the above reactions proceed even if other substituents defined in Chemical Formula 1 are attached in addition to the substituents specified in the specific synthetic examples. Meanwhile, the quantum efficiency of an organic photovoltaic device is oscillator strength, It is affected by ).

[0380] The oscillator intensity is a dimensionless numerical value representing the degree of interaction with light, and is a numerical value representing the absorption and luminescence intensity of the corresponding material. In the present invention, the oscillator intensity is from the ground state to the first singlet excited state (1 according to the Franck-Condon principle) st It was calculated based on the Transition Dipole Moment (TDM) value up to S1 (singlet excited state). The formula is as follows.

[0381]

[0382] (f: Oscillator strength, : S1state wave number, m e : Electron mass, c: Speed ​​of light, h: Planck's constant, e: Charge of electron, : Transition dipole moment strength)

[0383] In this invention, the Jaguar module, a quantum mechanics computation module of Schrodinger’s Materials Science (Maestro Materials Science 5.5.138, Release 2024-2), was used, and molecular structure optimization was performed using the module’s Density Functional Theory (DFT). As the DFT method, Becke, 3-parameter, Lee-Yang-Parr (B3LYP), known to be similar to experimental values ​​in organic compounds, was used, and 6-31G(d), one of the Pople basis sets, was used as the basis set. Based on the optimized molecular structure, the oscillator intensity of the first excited state was calculated using TD-B3LYP, which utilizes Time-dependent density-functional theory (TD-DFT), to obtain the first singlet excited state according to the Franck-Condon principle.

[0384] From the above equation, it can be seen that oscillator strength is proportional to the TDM strength value. Therefore, the greater the oscillator strength, the larger the TDM strength value, which represents the probability and intensity of electron transitions; this means that the absorption coefficient value corresponding to the y-axis of the UV / VIS spectrum is large at that wavelength. This implies that a large amount of light is absorbed, and the more light is absorbed, the higher the quantum efficiency of the compound can be.

[0385] Fabrication of Organic Photovoltaic Devices and Measurement of External Quantum Efficiency

[0386] [Example 1] Organic Photovoltaic Device

[0387] After forming 150 nm of ITO on a glass substrate, a 150 nm thick active layer was formed by co-depositing the compound of the present invention P21 and C60 (fullerene) on the ITO in a volume ratio of 1.1:1, and an organic photovoltaic device was fabricated by vacuum depositing 5 nm of ITO on the active layer.

[0388] [Examples 2] to [Examples 10]

[0389] An organic photovoltaic device was fabricated in the same manner as in Example 1, except that the compound of the present invention listed in Table 4 below was used instead of the compound P21 of the present invention as the active layer material.

[0390] [Comparative Example 1] to [Comparative Example 5]

[0391] An organic photovoltaic device was fabricated in the same manner as in Example 1, except that comparative compounds A to E were used instead of the compound P21 of the present invention as the active layer material.

[0392] Comparative Compound A

[0393]

[0394] <Comparison Compound B> <Comparison Compound C>

[0395]

[0396] <Comparison Compound D> <Comparison Compound E>

[0397]

[0398] The external quantum efficiency (hereinafter EQE) of the organic photovoltaic devices prepared according to the above examples and comparative examples was measured using IPCE measurement (Mc Science). The measurement results are as shown in Table 4 below.

[0399] Compound EQE (Room Temperature, %) Comparative Example 1 Comparative Compound A - Comparative Example 2 Comparative Compound B 22.6 Comparative Example 3 Comparative Compound C 15.9 Comparative Example 4 Comparative Compound D 11.9 Comparative Example 5 Comparative Compound E 20.1 Example 1 P21 26.7 Example 2 P22 26.9 Example 3 P24 25.9 Example 4 P26 26.5 Example 5 P27 25.6 Example 6 P30 33.1 Example 7 P51 34.8 Example 8 P52 36.3 Example 9 P53 31.5 Example 10 P54 32.6

[0400] As can be seen from the results in Table 4 above, the EQE of an organic photovoltaic device using the material for the organic photovoltaic device of the present invention as the active layer material shows a significantly high value. When comparing Comparative Compound A with the compound of the present invention, structural stability can be predicted through the IR spectrum.

[0401] The IR Spectrum values ​​used in this invention are values ​​resulting from frequency calculations using Gaussian's Gaussian program (Gaussian 09, Revision C.01). The BDE values ​​are Schrödinger (Schr We used the Jaguar module, a quantum mechanics computation module included in Materials Science (Maestro Materials Science 5.5.138, Release 2024-2) by dinger.

[0402] Figure 3 shows the IR spectrum of comparative compound A. Referring to Figure 3, at 3000 cm⁻¹ -1 Strong nearby CH vibrations appear, representing unwanted vibrational modes that can cause energy loss within the bond. This increases the likelihood that the compound's bonds will be easily damaged.

[0403] On the other hand, Fig. 4 shows the IR spectrum of compound P52 of the present invention; looking at Fig. 4, at 3000 cm⁻¹ -1It can be observed that nearby CH vibrations appear weakly. Therefore, it can be seen that the compound of the present invention has fewer unnecessary vibrations, which means that energy loss is minimal and bonds are maintained more strongly.

[0404] Therefore, Comparative Compound A is deemed unsuitable for the deposition process because its structural stability is reduced due to unnecessary vibration modes, and its molecular structure becomes even more unstable when thermal energy is injected.

[0405] Table 5 below shows the calculated BDE (Bond Dissociation Energy) for the bonding between the benzobisthiadiazole core and the substituents bonded thereto of Comparative Compounds A to E.

[0406] Compound B DE (eV) Comparative Compound A 5.525 Comparative Compound B 5.507 Comparative Compound C 5.179 Comparative Compound D 5.618 Comparative Compound E 5.545 P5 6.149 P2 6 6.556 P5 25.912 P5 35.923

[0407] From Table 5 above, it can be confirmed that the CC bonds of the compound of the present invention have a higher BDE compared to Comparative Compounds A to E. This implies that the compound of the present invention has high stability in high temperature or high-energy environments. Therefore, it can be seen that the compound of the present invention possesses significantly superior structural durability compared to Comparative Compounds A to E. Table 6 below shows the Excitation Energy and oscillator intensity (f) of Compound P52 and Comparative Compounds B to E from molecular simulation (Schr This is data measured using dinger Maestro Materials Science 5.5.138, Release 2024-2).

[0408] Material Name P52 Comparative Compound B Comparative Compound C Comparative Compound D Comparative Compound EE Excitation Energy (nm) 1138 117 196 3870 1110 Vibrator Strength (f) 0.837 0.719 0.508 0.38 10.639 Molecular Weight 796 793680 426742

[0409] Looking at Table 6 above, it can be confirmed that the oscillator strength of Compound P52 of the present invention is greater than that of Comparative Compound B, which has the highest oscillator strength. In particular, when comparing Comparative Compound B and Comparative Compound P52 of the present invention, there is a difference in the substituents applied to the benzobisthiadiazole core of the compound of the present invention. The compound of the present invention differs in that the benzobisthiadiazole core is substituted with Chemical Formula A-1 (e.g., benzoxazole or benzothiazole, etc.), whereas Comparative Compound A does not contain such substituents. It can be confirmed that the physical properties of the compounds differ due to this difference in substituents. Therefore, when the compound of the present invention is used as a P-type semiconductor compound for an organic photovoltaic device, the high oscillator strength appears to have had a significant effect on increasing the overall quantum efficiency of the device.

[0410] The foregoing description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. The scope of protection of the present invention shall be interpreted by the claims below, and all technology within an equivalent scope shall be interpreted as being included within the scope of rights of the present invention.

Claims

1. Compounds represented by Chemical Formula 1: <Chemical Formula 1> <Chemical Formula A-1> <Chemical Formula A-2> In the above chemical formula 1, A is the chemical formula A-1, and X and Y are independently O, S, Se, or Te, and Ar is C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si, Se, and Te 60 The heterocyclic group of; and N(R a )(R b Selected from a group consisting of ), L 1 and L 2 are independent single bonds; C6~C 60 arylene group; fluorenyllene group; C2~C comprising at least one heteroatom among O, N, S, Si, Se, and Te 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C3~C 60 The aliphatic ring and C6~C 60 Selected from a group consisting of fused rings of aromatic rings, The B ring has the chemical formula A-2, where x is an integer from 0 to 3, and V 1 and V 2 are independently O, S, Se, Te, N(R') or C(R')(R"), and when x is 2 or 3, multiple V 2 They are the same or different from each other, W 1 is CR' or N, provided that if x is 0, W 1 is N, and R 1 , R', R" independently of each other hydrogen; deuterium; halogen; cyano group; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and Se 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 30 alkyl group of; C2~C 30 The Alken Diary of; C2~C 30 Alkin's Diary; C1~C 30 alkoxy groups; C6~C 30 The aryloxy group of; and L'-N(R a )(R b Selected from a group consisting of ), and neighboring R 1 They can combine with each other to form a ring, and R' and R" can combine with each other to form a ring, a is an integer from 0 to 4, and The above R a and R b C6-C are independently of each other 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom among O, N, S, Si, Se, and Te 30 heterocyclic; and C3-C 30 Selected from a group consisting of aliphatic rings, The above L' is a single bond; C6~C 60 arylene group; fluorenyllene group; C2~C comprising at least one heteroatom among O, N, S, Si, Se, and Te 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C3~C 60 The aliphatic ring and C6~C 60 Selected from a group consisting of fused rings of aromatic rings, The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, adjacent R 1 The rings formed by the bonding of R' and R" together, and the rings formed by the bonding of R' and R" together, are respectively deuterium; halogen; cyano group; and C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom among O, N, S, Si, Se, and Te 60 heterocyclic; C3-C 30 Aliphatic ring; C3-C 30 The aliphatic ring and C6-C 30 A fused ring of an aromatic ring; and one or more substituents selected from the group consisting of combinations thereof, adjacent substituents may bond to each other to form a ring, and the hydrogen of the substituents may be replaced with deuterium.

2. In Paragraph 1, The above chemical formula A-1 is a compound represented by one of the following chemical formulas A-1-1 to A-1-4: <Chemical Formula A-1-1> <Chemical Formula A-1-2> <Chemical Formula A-1-3> <Chemical Formula A-1-4> In the above chemical formulas A-1-1 to A-1-4, V 1 , V 2 , W 1 , R 1 , a is the same as defined in Paragraph 1, and V 3 and V 4 is V 2 It is the same as the definition of.

3. In Paragraph 1, The compound represented by the above chemical formula 1 is one of the following compounds: .

4. In Paragraph 1, The above compound is a compound having a maximum absorption wavelength of 650 nm or more and 1300 nm or less in the thin film state.

5. An organic photovoltaic device comprising a first electrode, a second electrode, and an active layer between the first electrode and the second electrode, wherein An organic photovoltaic device characterized in that the active layer comprises the compound of claim 1.

6. In Paragraph 5, An organic photovoltaic device characterized in that the active layer comprises a p-type semiconductor compound and an n-type semiconductor compound, and the p-type semiconductor compound is the compound of claim 1.

7. An image sensor comprising the organic photovoltaic element of claim 5.

8. An electronic device comprising the image sensor of claim 7.

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