Compound for organic optoelectronic device

Abstract

Disclosed is a compound for an organic photoelectric device, which is represented by chemical formula 1. When the compound represented by the chemical formula 1 is used as a high-sensitivity and high-heat-resistance material and is applied to an organic photoelectric device, the efficiency and the stability of the device can be greatly improved.

Description

Technical Field

[0001] The present invention relates to a compound for organic photoelectric devices. Background Art

[0002] Photoelectric devices, which convert light into electrical signals using the photoelectric effect, are suitable for image sensors. Therefore, the development of photoelectric devices continues to advance in parallel with the development of image sensors.

[0003] As technology advances, the resolution of image sensors continues to increase, and pixel size is also decreasing. However, as pixel size decreases, the absorption area decreases, potentially leading to a decrease in sensitivity. To overcome this, research on optoelectronic devices is actively underway.

[0004] Recently, optoelectronic devices have been gradually replaced by organic materials using vacuum deposition, rather than mainly silicon or polymer materials such as those used in inkjet printing. In the case of organic materials, they can be designed to have a large absorption coefficient and, depending on their molecular structure, can selectively absorb light in a specific wavelength range. In other words, organic materials can absorb light in a desired color range and selectively detect it, thereby replacing existing optoelectronic devices and color filters at the same time. Therefore, in the case of organic materials, highly sensitive materials are required. Moreover, there is a need for organic optoelectronic devices that can also demonstrate high efficiency in high-temperature processes such as vacuum deposition. To this end, it is necessary to develop organic materials with excellent heat resistance.

[0005] Therefore, in order to realize excellent organic optoelectronic devices, research is currently needed to develop materials with high sensitivity and high heat resistance. Summary of the Invention

[0006] Technical issues

[0007] To address the aforementioned problems in the background art, the present invention discloses a compound having a novel structure and reveals that, when applied to organic optoelectronic devices, this compound can significantly improve the efficiency and stability of the devices. Accordingly, the present invention aims to provide a novel compound.

[0008] Technical Solution

[0009] In one aspect, the present invention provides a compound represented by the following Chemical Formula 1.

[0010]

[0011] In another aspect, the present invention provides an organic optoelectronic device, an image sensor and an electronic device thereof comprising the compound represented by the above chemical formula.

[0012] Effects of the Invention

[0013] 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 optoelectronic devices. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] Figure 1 and Figure 2 Schematic diagram of the stacked structure of an organic optoelectronic device according to an embodiment of the present invention.

[0015] Description of Reference Signs

[0016] 110: first electrode 120: second electrode

[0017] 130: Active layer 210: Hole transport band

[0018] 220: Electron transport domain DETAILED DESCRIPTION

[0019] The terms "aryl" and "arylene" used in the present invention have carbon numbers of 6 to 60, unless otherwise specified, but are not limited thereto. In the present invention, aryl or arylene includes monocyclic, polycyclic, and condensed ring structures.

[0020] The term "fluorenyl" used in the present invention means a substituted or unsubstituted fluorenyl group, and "fluorenylene" means a substituted or unsubstituted fluorenylene group. The fluorenyl or fluorenylene group used in the present invention include spiro compounds formed by mutual bonding between R and R' in the following structure, and also include cyclic compounds formed by mutual bonding between adjacent R". "Substituted fluorenyl" and "substituted fluorenylene" mean that in the following structure, at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R" in the following structure can have a valence of 1 to 8. Regardless of the valence number, fluorenyl and fluorenylene can be named as fluorenylfluorene ring or fluorene in this specification.

[0021]

[0022] The term "spiro compound" as used herein has a "spirounion," which means that two spiro rings are connected by sharing only one atom. In this case, the atom shared by the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, these are referred to as "monospiro," "bispiro," or "trispiro" compounds, respectively.

[0023] The term "heterocyclic group" as used in the present invention includes not only aromatic rings such as "heteroaryl" or "heteroarylene" but also non-aromatic rings. Unless otherwise specified, it means a ring having 2 to 60 carbon atoms that contains one or more heteroatoms, but the present invention is not limited thereto. The term "heteroatom" as used in the present invention, unless otherwise specified, refers to an element other than carbon, such as N, O, S, P, or Si, and may also include compounds containing heteroatomic groups such as SO2 and P=O in place of carbon atoms forming the ring, as in the following compounds.

[0024]

[0025] In addition, heterocyclic groups can include monocyclic, polycyclic, or fused rings containing heteroatoms. A fused ring is considered a heterocycle if at least one of the rings contains a heteroatom. For example, a fused ring formed by condensing a heterocycle such as furan, dihydrofuran, thiophene, pyrrole, or pyridine with an aromatic ring such as benzene, naphthalene, or phenanthrene, or with an alicyclic ring such as cyclopentane or cyclohexane, is also considered a heterocycle. Furthermore, a spirocyclic compound is also considered a heterocycle if at least one of the rings contains a heteroatom.

[0026] The term "aliphatic cyclic group" as used herein refers to cyclic hydrocarbons that do not contain aromatic hydrocarbons, including monocyclic, polycyclic, fused, and spirocyclic compounds. Unless otherwise specified, it refers to rings with 3 to 60 carbon atoms, but is not limited to these rings. Specifically, in this specification, an aliphatic ring (group) is defined as a hydrocarbon ring that does not contain any aromatic rings. Therefore, even saturated hydrocarbon rings, such as cycloalkyl groups, or even those containing one or more double bonds, are considered aliphatic rings as long as they are not aromatic hydrocarbons.

[0027] The term "fused ring (group)" or "condensed ring (group)" as used in this specification, unless otherwise specified, refers to a ring structure formed by the fusion of an aliphatic ring and an aromatic hydrocarbon (aromatic ring group or aryl ring). Unless otherwise specified, it means a ring formed by the fusion of an aliphatic ring having 3 to 60 carbon atoms and an aromatic hydrocarbon having 6 to 60 carbon atoms.

[0028] In this specification, the "group name" corresponding to an aryl group, arylene group, heterocyclic group, etc., shown as examples of each symbol and its substituent, may be described as the "group name reflecting the valence number," but may also be described as the "name of the parent compound." For example, in the case of "phenanthrene," a type of aryl group, the monovalent "group" is "phenanthryl," and the divalent "group" is "phenanthrylene." While the group name may be described by distinguishing the valence number, it may also be described as "phenanthryl," the name of the parent compound, regardless of the valence number. Similarly, in the case of pyrimidine, regardless of the valence number, it may be described as "pyrimidine," or as the "group name" of the corresponding valence number. For example, in the case of a monovalent group, it may be described as "pyrimidinyl," and in the case of a divalent group, it may be described as "pyrimidinylene."

[0029] In addition, when describing the names of compounds or substituents in the present invention, numerals or letters indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofuro[2,3-d]pyrimidine may be described as benzofuropyrimidine, and 9,9-dimethyl-9H-fluorene may be described as dimethylfluorene. Thus, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzoquinoxaline.

[0030] Furthermore, unless otherwise specified, the chemical formulae used in this specification are applicable in the same manner as the definitions of substituents defined by the indices in the following chemical formulae.

[0031]

[0032] When a is an integer of 0, the substituent R 1 In the absence of a, that is, when a is 0, it means that all carbon atoms forming the benzene ring are bonded with hydrogen atoms. In this case, the representation of hydrogen atoms bonded to carbon atoms can be omitted and the chemical formula or compound can be described. 1 Combined with one of the carbon atoms forming the benzene ring, when a is an integer of 2 or 3, respectively, in the following manner, when a is an integer of 4 to 6, in a similar manner, when a is an integer greater than or equal to 2, R 1 They may be the same as or different from each other.

[0033]

[0034] In this specification, unless otherwise specified, "ring" means an aromatic ring, a heteroaromatic ring, a fluorene ring, an aliphatic ring, or the like. "Number" may mean a condensed ring, and "number" may mean a single ring. For example, naphthalene corresponds to a condensed ring with two rings, anthracene to a condensed ring with three rings, thiophene, furan, and the like to a condensed ring with five rings, and benzene and pyridine to a condensed ring with six rings.

[0035] Furthermore, unless otherwise specified in this specification, the ring formed by the bonding of adjacent groups is selected from the group consisting of C6 to C 60 Aromatic ring group; Fluorenyl; C2~C containing at least one hetero atom of O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; and C3~C 60 Aliphatic ring groups and C6~C 60 In this case, the aromatic ring group may be an aromatic ring, and the heterocyclic group may include a heteroaromatic ring.

[0036] Unless otherwise specified, the term "between adjacent groups" in this specification refers not only to groups between R1 and R2, R2 and R3, R3 and R4, and R5 and R6, but also to groups between R7 and R8, which share a common carbon. It also includes substituents bound to non-directly adjacent ring-constituent elements (such as carbon or nitrogen), such as between R1 and R7, R1 and R8, or R4 and R5. Specifically, when directly adjacent ring-constituent elements, such as carbon or nitrogen, have substituents, they are considered adjacent groups. However, if the directly adjacent ring-constituent element has no substituents, the substituent bound to the next ring-constituent element is considered an adjacent group. Furthermore, substituents bound to the same ring-constituent carbon are also considered adjacent groups. In the following chemical formula, when substituents bound to the same carbon, such as R7 and R8, are bonded to form a ring, a compound containing a spirocyclic moiety may be formed.

[0037] ,

[0038] In this specification, the expression 'adjacent groups combine to form a ring' is used synonymously with 'adjacent groups combine to selectively form a ring' and means that at least one pair of adjacent groups combine to form a ring.

[0039] Furthermore, unless otherwise specified in the present specification, substituents such as aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, alkylthio, arylthio, and the like, and rings formed by bonding adjacent groups, can be selected from deuterium, halogen, cyano, nitro, siloxane, C6-C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 30 Heterocyclic group, C3~C 30 Aliphatic ring group, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C1~C 20 Alkoxy, C6~C 20 Aryloxy, C1~C 20 Alkylthio, C6~C 20 The arylthio group, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, and C1~C 20 Alkyl or C6~C 20 The aryl-substituted or unsubstituted phosphine oxide group may be further substituted with one or more substituents selected from the group consisting of the aryl-substituted or unsubstituted phosphine oxide group.

[0040] Hereinafter, the compound according to one aspect of the present invention will be described.

[0041] The compound of one aspect of the present invention is represented by the following Chemical Formula 1.

[0042] <Chemical Formula 1>

[0043] In the chemical formula 1, each symbol can be defined as follows.

[0044] X 1 and X 2 are independently single bonds, C(R a )(R b ) or Si (R c )(R d ), where X 1 and X 2 At least one of them is C (R a )(R b ) or Si (R c )(R d ).

[0045] a and b are each 0 or 1, wherein a+b is 1 or 2. In the case where a and b are 0, it means X 1、X 2 does not exist, so no ring is formed. Therefore, X 1 With X 2 Except for the case where neither of them exists or both are single bonds.

[0046] R a 、R b 、R c and R d Independently selected from hydrogen; deuterium; halogen; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing the aromatic rings of 30 Alkyl; C2~C 30 Alkenyl; C2~C 30 Alkynyl; C1~C 30 Alkoxy; and C6~C 30 The group is composed of aryloxy groups, and R a and R b Between groups, R c and R d The groups may combine with each other to form a ring.

[0047] Among them, R a 、R b 、R c and R d At least one of them contains deuterium. For example, R a to R d At least one of them is deuterium, or the above substituents may be substituted with deuterium. 1 C (R a )(R b ) or Si (R c )(R d ), R a and R b At least one or R c and R d At least one of them may be an alkyl group, and the hydrogen in the alkyl group may be replaced by deuterium. a and R b One or all of them can be -CD3 (methyl substituted by heavy hydrogen), R c and R d One or all of them may be -CD3 (methyl substituted with deuterium).

[0048] When R a With Rb When the groups are combined to form a ring, a ring in which C is a spiro atom can be formed, and the ring can be selected from C6 to C 30 Aromatic ring group; fluorenyl group; C2 to C containing at least one hetero atom selected from the group consisting of O, N, S, Si, P and Se 30 Heterocyclic group; C3~C 30 Aliphatic ring group; and C3~C 30 Aliphatic ring and C6~C 60 A group consisting of a fused ring group formed by condensing aromatic rings.

[0049] For example, when R a and R b When the groups combine to form an aliphatic ring, the aliphatic ring can be C3 to C 30 、C3~C 29 、C3~C 28 、C3~C 27 、C3~C 26 、C3~C 25 、C3~C 24 、C3~C 23 、C3~C 22 、C3~C 21 、C3~C 20 、C3~C 19 、C3~C 18 、C3~C 17 、C3~C 16 、C3~C 15 、C3~C 14 、C3~C 13 、C3~C 12 、C3~C 11 、C3~C 10 , C3~C8, C3~C6, C5~C6, C6, C 10 、C 11 、C 12 、C 13 、C 14 、C 15 、C 16 、C 17 、C 18 and the like, specifically, cyclopentyl, cyclohexyl, indenyl, tetrahydronaphthyl, norbornyl, adamantyl, and the like.

[0050] When R c With R d When the groups combine to form a ring, they can form a Si-containing C3~C 60 Heterocyclic group.

[0051] X3 It is O, S, Se or Te.

[0052] Ar is C6~C 60 or a C2-C 60 wherein Ar comprises one or more functional groups selected from the group consisting of C═O, C═S, C═Se, C═Te, CN and CF 3 .

[0053] The hydrocarbon ring group refers to a cyclic substituent composed of carbon and hydrogen, with all atoms forming the ring being carbon. It may be a monocyclic, polycyclic, or fused ring, and may be a saturated or unsaturated ring. In other words, it may be a cycloalkyl group and may contain one or more double or triple bonds within the ring.

[0054] Ar contains one or more functional groups selected from the group consisting of C=O, C=S, C=Se, C=Te, CN, and CF3. The term "C=O, C=S, C=Se, or C=Te" refers to a form in which, for example, O, S, Se, or Te are double-bonded to a carbon atom forming a ring. The term "CN" or "CF3" refers to a form in which these substituents directly or indirectly substitute on a carbon atom forming a ring. Indirect substitution with CN or CF3 corresponds, for example, to an alkenyl group substituted in the Ar ring, where the alkenyl group replaces CN. That is, an alkenyl group substituted with CN or CF3 may be, for example, a form in which =CH2 is directly substituted in the Ar ring, with one or two hydrogen atoms replaced by CN, or a form in which =C(CN)(H) or =C(CN)2 is substituted.

[0055] When Ar is a hydrocarbon ring group, the hydrocarbon ring group may be, for example, a monocyclic ring such as cyclopentane, cyclopentene, or cyclohexane, or a condensed ring formed by condensing these monocyclic rings with benzene, naphthalene, or phenanthrene. In this case, the monocyclic ring or condensed ring may contain a ring selected from C=O, C=S, C=Se, C=Te, CN, and C More than one functional group in the group.

[0056] When Ar is a heterocyclic group, the heterocyclic group can be, for example, C2 to 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~C13 、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 The heterocyclic group can be a monocyclic ring containing heteroatoms, or a condensed ring formed by condensing a heterocyclic ring with a heterocyclic ring, or a condensed ring formed by condensing a heterocyclic ring with a hydrocarbon ring such as an aliphatic ring or an aromatic ring. For example, the heterocyclic group can be a monocyclic ring such as furan, tetrahydrofuran, thiophene, pyrazolidine, pyridine, pyrimidine, pyrazine, tetrahydropyridine, hexahydropyrimidine, dioxane, disulfide, thiazolidine, or a condensed ring formed by condensing these monocyclic rings with hydrocarbon rings such as cyclopentane, cyclohexane, benzene, naphthalene, phenanthrene, triphenylene, or a condensed ring formed by condensing these monocyclic rings with a hydrocarbon ring such as thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, thiothiophene, quinoline, quinazoline, etc. In this case, the monocyclic or condensed ring can contain one or more rings selected from C=O, C=S, C=Se, C=Te, CN and C functional groups.

[0057] R 1 to R 4 Independently selected from hydrogen; deuterium; halogen; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing the aromatic rings of 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; and C6~C 60 The aryloxy group is composed of adjacent R 1Between groups, adjacent R 2 The groups may combine with each other to form a ring.

[0058] x is an integer from 0 to 4, y is an integer from 0 to 5, and when these are integers of 2 or more, a plurality of R 1 Each, multiple R 2 Each, multiple R 3 Individual and multiple R 4 Each may be the same or different.

[0059] Adjacent R 1 Between groups, adjacent R 2 When the groups are combined to form a ring, the ring can be selected from C6 to C 60 Aromatic ring group; fluorenylene; C3~C 60 Containing at least one hetero atom selected from the group consisting of O, N, S, Si, P and Se C2 ~ C 60 Heterocyclic group; and C3~C 60 A group consisting of aliphatic ring groups.

[0060] For example, adjacent R 1 Between groups, adjacent R 2 When the ring formed by the groups bonded to each other is an aromatic ring, the aromatic ring may be, for example, C6 to C 20 、C6~C 18 、C6~C 16 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 10 , C6, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 The aromatic rings include benzene, naphthalene, anthracene, phenanthrene, pyrene and the like.

[0061] Adjacent R 1 Between groups, adjacent R 2 When the ring formed by the mutual combination of the groups is a heterocyclic ring, the heterocyclic ring may be, for example, C2 to 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~C15 、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, C3~C8, C4~C8, 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 More specifically, the heterocyclic ring may be thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, or the like.

[0062] Adjacent R 1 Between groups, adjacent R 2 When the ring formed by the combination of the groups is a condensed ring, the condensed ring can be, for example, C3 to C 60 The aliphatic ring and C6~C 60 A fused ring formed by condensing an aromatic ring of C3~C 30 The aliphatic ring and C6~C 60 A fused ring formed by condensing an aromatic ring of C3~C 18 The aliphatic ring and C6~C 18 A fused ring formed by condensing an aromatic ring of 10 The aliphatic ring and C6~C 14 Specifically, it can be a condensed ring formed by condensing an aromatic ring of cyclopentane or cyclohexane with benzene or naphthalene.

[0063] When R 1 to R 4 When there is at least one aryl group in the 30 、C6~C 29 、C6~C 28 、C6~C 27 、C6~C 26 、C6~C 25 、C6~C 24 、C6~C23 、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 Specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, and the like.

[0064] When R 1 to R 4 When at least one aliphatic ring is present in the 30 、C3~C 29 、C3~C 28 、C3~C 27 、C3~C 26 、C3~C 25 、C3~C 24 、C3~C 23 、C3~C 22 、C3~C 21 、C3~C 20 、C3~C 19 、C3~C 18 、C3~C 17 、C3~C 16 、C3~C 15 、C3~C 14 、C3~C 13 、C3~C 12 、C3~C 11 、C3~C 10 、C3~C8、C3~C6、C6、C 10 、C 11 、C 12 、C 13 、C14 、C 15 、C 16 、C 17 、C 18 and the like, specifically, cyclopentyl, indenyl, tetrahydronaphthyl, cyclohexyl, norbornyl, adamantyl, and the like.

[0065] The aryl, fluorenyl, heterocyclic, aliphatic, condensed, carbocyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent R 1 Between groups, adjacent R 2 Between groups, R a and R b Between groups, R c and R d The ring formed by the mutual combination of groups can be selected from deuterium, halogen, siloxane, cyano, nitro, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 24 Heterocyclic group, C3~C 20 Aliphatic ring groups, and C3~C 30 Aliphatic ring and C6~C 30 The aromatic rings are fused to form a fused ring group, and the ....

[0066] When the aryl, fluorenyl, heterocyclic, aliphatic, condensed, carbocyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent R 1 Between groups, adjacent R 2 Between groups, R a and R b Between groups, R c and R d When at least one of the rings formed by the groups is further substituted by an alkyl group, the alkyl group may be, for example, C1 to C 20 、C1~C10 , C1~C4, C1, C2, C3, C4 and other alkyl groups, such as methyl, ethyl, tert-butyl and the like.

[0067] The Chemical Formula 1 may be expressed as any one of the following Chemical Formulas 2 to 16.

[0068] <Chemical Formula 2> <Chemical Formula 3> <Chemical Formula 4>

[0069] <Chemical Formula 5> <Chemical Formula 6> <Chemical Formula 7>

[0070] <Chemical Formula 8> <Chemical Formula 9> <Chemical Formula 10>

[0071] <Chemical Formula 11> <Chemical Formula 12>

[0072] <Chemical Formula 13> <Chemical Formula 14>

[0073] <Chemical Formula 15> <Chemical Formula 16>

[0074] In the chemical formulas 2 to 16, X 1 To X 3 、R 1 to R 4 、R a to R d , Ar are the same as defined in Chemical Formula 1, m is an integer of 0 to 3, n and m' are integers of 0 to 4, and n' is an integer of 0 to 5.

[0075] Since Ar contains one or more functional groups selected from the group consisting of C=O, C=S, C=Se, C=Te, CN and CF3, it can be a form in which O, S, Se, Te, etc. are directly bonded to at least one carbon forming the ring, or CN or CF3 is directly or indirectly substituted in the ring.

[0076] For example, Ar may be selected from the group consisting of Chemical Formula 17 to Chemical Formula 19 below.

[0077] <Chemical Formula 17> <Chemical Formula 18> <Chemical Formula 19>

[0078] In the Chemical Formulas 17 to 19, Indicates the bonding site, Z 1 to Z 7 independently selected from O, S, Se, Te and C (R e )(R f ) is a group composed of .

[0079] R e and R f independently selected from hydrogen; deuterium; halogen; cyano; and substituted or unsubstituted C1-C 20 of alkyl.

[0080] Y 1 To Y 4 Independently selected from O, S, Se, Te, C (R g )(R h ) and N (R i ) is a group composed of .

[0081] R g 、R h and R i independently selected from hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C 20 Alkyl; and substituted or unsubstituted C2~C 20 A group consisting of alkenyl groups.

[0082] Y 5 and Y 6 are independently N or C (R j ).

[0083] R j independently selected from hydrogen, deuterium, halogen, siloxane, cyano, nitro, C1-C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 24 Heterocyclic group, C3~C 30 Aliphatic ring groups, and C3~C30 Aliphatic ring and C6~C 30 The aromatic rings are fused to form a fused ring group, and the adjacent R j The groups may combine with each other to form a ring.

[0084] Adjacent R j When the groups are combined to form a ring, the ring can be selected from C6 to C 30 Aromatic ring group; fluorenyl group; C2 to C containing at least one hetero atom selected from the group consisting of O, N, S, Si, P and Se 30 Heterocyclic group; C3~C 30 Aliphatic ring group; and C3~C 30 Aliphatic ring and C6~C 30 A group consisting of a fused ring group formed by condensing aromatic rings.

[0085] For example, adjacent R j When the groups are bonded to each other to form an aromatic ring, the aromatic ring may be, for example, C6 to C 20 、C6~C 18 、C6~C 16 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 10 , C6, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 The aromatic rings include, for example, aromatic rings of benzene, naphthalene, anthracene, phenanthrene, pyrene, and the like.

[0086] Adjacent R j When the ring formed by the mutual combination of the groups is a heterocyclic ring, the heterocyclic ring may be, for example, C2 to 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, C3~C8, C4~C8, 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 More specifically, the heterocyclic ring may be thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, or the like.

[0087] Adjacent R j When the ring formed by the combination of the groups is a condensed ring, the condensed ring can be, for example, C3 to C 30 The aliphatic ring and C6~C 30 A fused ring formed by condensing an aromatic ring of C3~C 18 The aliphatic ring and C6~C 18 A fused ring formed by condensing an aromatic ring of 10 The aliphatic ring and C6~C 14 Specifically, it can be a condensed ring formed by condensing an aromatic ring of cyclopentane or cyclohexane with benzene or naphthalene.

[0088] Adjacent R j The ring formed by the mutual combination of groups can be selected from deuterium, halogen, cyano, C1~C 20 Alkyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 24 Heterocyclic group, C3~C 30 Aliphatic ring groups, and C3~C 30 Aliphatic ring and C6~C 30 The aromatic rings are fused to form a fused ring group, and the ....

[0089] Specifically, the Chemical Formula 17 may be selected from the group consisting of the following chemical formulas, but is not limited thereto.

[0090]

[0091] In addition, the Chemical Formula 19 may be selected from the group consisting of the following chemical formulas, but is not limited thereto.

[0092]

[0093] Specifically, the compound represented by Chemical Formula 1 may be one of the following compounds, but is not limited thereto.

[0094]

[0095] The compound represented by Chemical Formula 1 of the present invention is contained in the active layer of an organic photoelectric device. That is, the compound represented by Chemical Formula 1 of the present invention can be used as a compound for an organic photoelectric device.

[0096] Below, refer to Figure 1 and Figure 2 An organic photoelectric device including the compound of Chemical Formula 1 of the present invention is described.

[0097] Figure 1 and Figure 2 FIG. 1 is a diagram illustrating a stacked structure of an organic photoelectric device according to an embodiment of the present invention.

[0098] In assigning reference numerals to the structural elements of the drawings, it is important to note that identical structural elements, even if shown in different drawings, should be assigned the same reference numerals whenever possible. Furthermore, in describing the present invention, detailed descriptions of related known structures or functions may be omitted if it is determined that such detailed descriptions would obscure the gist of the present invention.

[0099] When describing the structural elements of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are used solely to distinguish one structural element from another and do not limit the nature, order, or sequence of the related structural elements. When a structural element is "connected," "coupled," or "coupled" to another structural element, the structural element may be directly connected or coupled to the other structural element, but it can also be understood that there are other structural elements "connected," "coupled," or "coupled" between the structural elements.

[0100] Furthermore, when a structural element such as a layer, film, region, or plate is located "on" or "above" another structural element, this should be understood not only as being "directly above" the other structural element, but also as meaning that there are other structural elements in between. Conversely, when a structural element is located "directly above" another part, it should be understood that there are no other parts in between.

[0101] Reference Figure 1 The organic photoelectric 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. Figure 2 The organic photoelectric device may further include a hole transport zone 210 between the first electrode 110 and the active layer 130 and an electron transport zone 220 between the second electrode 120 and the active layer 130 .

[0102] Any one of the first electrode 110 and the second electrode 120 is a cathode, and the other is an anode. The anode can be a transmissive electrode. Typically, as a material for forming the transmissive electrode, transparent conductive oxides (TCOs) such as indium tin oxide (ITO), zinc oxide (ZnO), tin oxide (SnO) and the like can be used. ) or indium zinc oxide (IZO) and a combination thereof, but is not limited thereto. In addition, the anode may be formed of a multilayer structure including two or more layers.

[0103] The cathode is preferably composed of one or more metal substances, which can be selected from magnesium (Mg), silver (Ag), aluminum (Al), lithium (Li), calcium (Ca), indium (In), and combinations thereof. Preferably, the cathode is composed of a mixture of Mg and Ag, but is not limited thereto. The cathode may also be formed of a multilayer structure comprising two or more layers.

[0104] When light enters from the outside, the compounds in the active layer 130 are excited by the photoelectric effect, resulting in the formation of excitons. The holes and electrons in these excitons separate and migrate to the first and second electrodes 120, respectively, generating an electrical signal. For example, when the first electrode 110 serves as the anode, the holes migrate to the first electrode 110, while the electrons migrate to the second electrode 120, generating an electrical signal.

[0105] The active layer 130 may be formed as a single layer or multiple layers, 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, thereby forming a pn junction.

[0106] The compound represented by Chemical Formula 1 of the present invention is contained in the active layer 130, and is preferably a p-type semiconductor compound suitable for the active layer 130. In order to form a pn junction in the active layer 130, the active layer 130 may further include an n-type semiconductor compound.

[0107] The n-type semiconductor compound may be 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 these are merely examples of n-type semiconductor compounds and are not limited thereto.

[0108] The above fullerene can be made of C 60 ~C 540 Examples of fullerenes include C 60 、C 70 、C 76 、C 78 、C 80 、C 82 、C 84 、C90 、C 96 、C 240 、C 540 , and mixtures thereof, and fullerene nanotubes.

[0109] The so-called fullerene derivatives refer to compounds formed by introducing substituents into fullerene molecules. 30 Alkyl, C6~C 30 Aryl or C3~C 30 Fullerene substituted with a substituent such as a heterocyclic group.

[0110] The aryl group can be phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl, fluorenyl, triphenyl, naphthoanthryl, etc., and the heterocycle can be pyrrole, furan, thiophene, imidazole, oxazole, thiazole, pyridine, pyrazine, pyrimidine, pyridazine, indole, benzofuran, benzothiophene, isobenzofuran, benzimidazole, imidazopyridine, quinoline, quinoline, o-benzodiazine, naphthyridine, quinoxaline, quinazoline, isoquinoline, carbazole, phenanthridine, acridine, phenanthroline, thianthrene, chromene, xanthene, phenoxazine, phenoxidine, phenothiazine or phenazine, etc., but are not limited thereto.

[0111] <Chemical Formula 30>

[0112] In the chemical formula 30, each symbol can be defined as follows.

[0113] R 31 to R 33 independently selected from hydrogen; deuterium; halogen; cyano; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing the aromatic rings of 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; and C6~C 60 The adjacent groups can be combined with each other to form a ring.

[0114] a1, b1 and c1 are integers of 1 to 3, and when they are integers of 2 or more, R 31 Respectively, R 32 Respectively, R 33The same or different respectively.

[0115] Z is a monovalent substituent, which may be a halogen or a halogen-containing group, such as F, Cl, a F-containing group, or a Cl-containing group.

[0116] <Chemical Formula 31> <Chemical Formula 32>

[0117] In Chemical Formula 31 and Chemical Formula 32, each symbol can be defined as follows.

[0118] T 1 To T 3 may be a heterocyclic ring containing a thienyl group, and T 1 To T 3 They can combine with each other to form a ring.

[0119] X 10 To X 15 independently selected from hydrogen; deuterium; halogen; cyano; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing the aromatic rings of 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; and C6~C 60 A group composed of aryloxy groups.

[0120] EWG1 and EWG2 represent electron withdrawing groups. For example, in the above chemical formula 31, X 10 To X 15 At least one of them may be an electron-withdrawing group, preferably CN or a group containing CN.

[0121] <Chemical Formula 33>

[0122] In the chemical formula 33, each symbol can be defined as follows.

[0123] Z 11 and Z 12 are each independently N(R1), O or S, Y 11 To Y 14is C(R2)(R3), O or S.

[0124] R 41 、R 42 , R1 to R3 are independently selected from hydrogen; deuterium; halogen; cyano; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C6~C 60 The aromatic ring and C3~C 60 A fused ring group formed by condensing an aliphatic ring of 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; and C6~C 60 The adjacent groups can be combined with each other to form a ring, and the R2 and R3 groups can also be combined with each other to form a ring.

[0125] R2 and R3 are preferably halogen or cyano.

[0126] a2 and b2 are each an integer from 0 to 4, and x1 is an integer from 1 to 3.

[0127] In the chemical formulas 30 to 33, the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic cyclic group, condensed cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and the ring formed by the combination of adjacent groups can be selected from deuterium, halogen, siloxane, cyano, nitro, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 24 Heterocyclic group, C3~C 30 Aliphatic ring groups, and C3~C 30 Aliphatic ring and C6~C30 The aromatic rings are fused to form a fused ring group, and the ....

[0128] Specifically, the compound represented by Chemical Formula 33 may be one of the following compounds, but is not limited thereto.

[0129]

[0130] The compound represented by the chemical formula 1 is a compound that generally absorbs light in the visible light region and has a maximum absorption wavelength (λ) of 500 nm or more in a thin film state. max ) is preferred.

[0131] In particular, in a thin film state, the maximum absorption wavelength is preferably 500 nm to 600 nm. More preferably, the maximum absorption wavelength is 500 nm to 550 nm. That is, as described above, the active layer 130 containing the compound preferably has a maximum absorption wavelength of 500 nm or greater, more preferably 500 nm to 600 nm, or 500 nm to 550 nm.

[0132] Therefore, the active layer 130 can selectively absorb and / or sense light in the green wavelength region and can also replace the color filter of the green pixel.

[0133] For compounds represented by Chemical Formula 1, a smaller full width at half maximum (FWHM) of the absorption curve is generally preferred. A smaller FWHM indicates that the compound has a very high selectivity for the wavelength of light absorbed. In other words, compounds with a narrow FWHM can be considered materials with high selectivity and sensitivity. Preferably, the active layer 130 comprising the compound represented by Chemical Formula 1 has a FWHM of 50 nm to 100 nm.

[0134] When the compound represented by Chemical Formula 1 is used as a p-type semiconductor compound, it is preferred that the LUMO energy level be higher than that of the n-type semiconductor with which it is mixed. The energy levels described below are expressed in absolute values. For example, when mixed with an n-type material such as fullerene, which has a LUMO energy level of approximately 4.2 eV, the LUMO energy level of the compound represented by Chemical Formula 1 is preferably 3.7 to 2.7 eV higher than the LUMO energy level of the fullerene.

[0135] Furthermore, in order to absorb energy in the green wavelength region, it is preferable that the energy band gap is 2.0 to 2.5 eV. Therefore, it is preferable that the HOMO energy level of the compound represented by the chemical formula 1 is 4.7 to 6.2 eV.

[0136] When the compound represented by Chemical Formula 1 that satisfies the above conditions is used in the active layer 130 , the compound can have high external quantum efficiency (EQE) as a material that effectively absorbs light in a green wavelength region.

[0137] Furthermore, as previously described, by including the compound represented by Chemical Formula 1 in the active layer 130, aggregation of the compound can be prevented even in a thin film state, thereby maintaining wavelength-dependent light absorption characteristics. This allows for the provision of an organic optoelectronic device that selectively absorbs green wavelengths of light. In particular, unnecessary absorption of light of wavelengths other than green can be reduced, thereby providing a highly sensitive organic optoelectronic device.

[0138] The p-type semiconductor compound and the n-type semiconductor compound as the compound represented by Chemical Formula 1 may have a volume ratio of about 9:1 to about 1:9, and preferably, a volume ratio of 1:3 to 1:5.

[0139] The ratio of p-type semiconductor compounds to n-type semiconductor compounds has a great influence on the performance of organic optoelectronic devices. When the ratio of p-type semiconductor compounds to n-type semiconductor compounds is 1:1, it can have a value of about 6.0x10 4 cm -1 The absorption coefficient is preferably 6.0x10 4 cm -1 to 1.0x10 5 cm -1 Absorption coefficient.

[0140] The active layer 130 including the p-type semiconductor compound or the n-type semiconductor compound may be a mixture of two or more compounds, but is not limited thereto.

[0141] The charge converted from photoelectric conversion may not be fully utilized, leaving some charge behind. If the residual charge is high, then if light irradiation is stopped after continued exposure, the remaining charge will cause the device to be perceived as light even after the irradiation has ceased. Therefore, high residual charge makes it unsuitable for use as an image sensor. In other words, organic photoelectric devices with low residual charge are preferred, as only low residual charge can provide high sensitivity.

[0142] To measure the residual charge, it is necessary to irradiate light of a specific wavelength region at a certain intensity for a certain period of time, then stop irradiating the light. After stopping the light irradiation, the current flowing is integrated over time to perform the measurement.

[0143] The active layer 130 is formed by a high temperature process such as vacuum deposition, thereby preparing an organic optoelectronic device. The vacuum deposition method is conducive to forming a uniform thin film, has a low possibility of impurities, and has many advantages in terms of process. However, when the decomposition temperature (T d ) is lower than the deposition temperature (T s ), the compound may decompose at high temperatures and the decomposition products may be deposited together, which may hinder the overall performance of the device. Therefore, it is preferable that the decomposition temperature of the compound is higher than the deposition temperature.

[0144] That is, when the deposition temperature (T s ) is higher than the decomposition temperature (T d ), decomposition occurs before sublimation (deposition), so normal devices cannot be prepared, and problems such as deposition of decomposed impurities will occur, which will reduce the performance of the device.

[0145] Therefore, in order to prepare a stable image sensor, the decomposition temperature (T d ) must be higher than the deposition temperature (T s ), preferably T d -T s ≥10℃.

[0146] Furthermore, when manufacturing image sensors, a microlens array (MLA) must be formed after device fabrication to focus light. This formation requires high temperatures (approximately 160°C to 190°C or higher). Therefore, organic optoelectronic devices must not be thermally degraded during the MLA heat treatment.

[0147] That is, the thermal degradation that occurs in the MLA process does not refer to chemical decomposition, but rather refers to thermal degradation caused by morphological changes, which usually occur when the material begins to vibrate and move due to heat treatment.

[0148] Therefore, if the molecular structure is robustly designed, vibrational motion caused by heat can be reduced, and thermal degradation caused by heat treatment can be prevented. In the case of the compound represented by Chemical Formula 1 of the present invention, by making the core have a conjugated structure, molecular vibration can be prevented, thereby increasing process stability.

[0149] Moreover, as the material of the active layer 130, among the compounds represented by Chemical Formula 1, it is preferred to use a compound that can be stably deposited, for example, a compound having a molecular weight of approximately 300 to 1000 g / mol, preferably a compound having a molecular weight of 300 to 800 g / mol, and more preferably a compound having a molecular weight of 350 to 700 g / mol can be used in the deposition process.

[0150] When the compound represented by Chemical Formula 1 that satisfies the above conditions is used in an organic photoelectric device, a highly heat-resistant organic photoelectric device suitable for a high-temperature process such as vacuum deposition can be prepared.

[0151] The active layer 130 can have a thickness of 1 to 500 nm, preferably 5 to 300 nm. This thickness effectively absorbs light and effectively separates and transports holes and electrons, thereby maximizing efficiency. The thickness of the active layer 130 depends on the absorption coefficient of the material used for the active layer 130. It is preferred that the thickness absorbs at least 70%, preferably at least 80%, and more preferably at least 90% of light.

[0152] Reference Figure 2 The organic photoelectric device may further include a hole transport zone 210 disposed between the first electrode 110 and the active layer 130 , and an electron transport zone 220 disposed between the second electrode 120 and the active layer 130 .

[0153] By forming the hole transport band region 210 and the electron transport band region 220 , the holes and electrons separated in the active layer 130 can move more easily and quickly, thereby improving the efficiency of the optical device.

[0154] The hole transport zone 210 may include a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a hole transport auxiliary layer, etc., and may include at least one hole transport layer.

[0155] The hole transport region 210 may include organic matter, inorganic matter, or an organic-inorganic composite. The organic matter may be an organic compound having electronic properties, but is not limited thereto.

[0156] The hole transport band domain 210 may include, for example, a polymer compound, such as poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS), a polyarylamine, or an organic compound, such as N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (TPD), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]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, etc., but is not limited thereto.

[0157] For example, the hole transport layer 210 may include an amine compound, and specifically, may include a compound represented by the following Chemical Formula 40 or Chemical Formula 41.

[0158] <Chemical Formula 40> <Chemical Formula 41>

[0159] In the above Chemical Formula 40 and Chemical Formula 41, each symbol can be defined as follows.

[0160] Ar 1 to Ar 7 Independently selected from C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing an aromatic ring of 20 A group consisting of alkyl groups.

[0161] L 1 To L 8 Independently selected from single bonds; C6~C 60 Arylene; Fluorenylene; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 and C2 to C3 containing at least one hetero atom selected from O, N, S, Si and P. 60 A group consisting of a heterocyclic group.

[0162] The aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic, condensed cyclic, and alkyl groups can be selected from deuterium, halogen, siloxane, cyano, nitro, C1-C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 60 Heterocyclic group, C3~C 30 Aliphatic ring groups, and C3~C 30 Aliphatic ring and C6~C 30 The aromatic rings are fused to form a fused ring group, and the ....

[0163] The above Chemical Formula 40 can be expressed as any one of the following Chemical Formulas 40-1 to 40-3.

[0164] <Chemical Formula 40-1> <Chemical Formula 40-2> <Chemical Formula 40-3>

[0165] In the above Chemical Formulas 40-1 to 40-3, Ar 2 、Ar 3 、L 1 ~L 3 Same as defined in Chemical Formula 40.

[0166] X 21 and X 22 Independently of each other, they represent single bonds, O, S, N (R 11 )、C(R 12 )(R 13 ) or Si (R 14 )(R 15 ), excluding the case where both are single bonds.

[0167] Ar a 、R 11 to R 15 、R51 to R 55 independently selected from hydrogen; deuterium; halogen; cyano; nitro; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing the aromatic rings of 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; and C6~C 60 The adjacent groups can be combined with each other to form a ring.

[0168] Ar b Indicates C3~C 60 The aliphatic ring group is preferably C3~C 60 of a cycloalkyl group.

[0169] a3, c3 and d3 are integers of 0 to 4, b3 and e3 are integers of 0 to 3; when they are integers of 2 or more, multiple R 51 To multiple R 55 The same or different respectively.

[0170] The above Chemical Formula 40-1 can be expressed as the following Chemical Formula 40-1-1 or Chemical Formula 41-1-2.

[0171] <Chemical Formula 40-1-1> <Chemical Formula 40-1-2>

[0172] In the above Chemical Formula 40-1-1 and Chemical Formula 40-1-2, Ar 2 、Ar 3 、L 1 ~L 3 、X 21 、R 51 、R 52 , a3 and b3 have the same meanings as those defined in Chemical Formula 40-1, R 56 and R 57 With R 12 and R 13 The definition is the same.

[0173] In the above chemical formula 40-3, Ar b The following chemical structures can be selected, but are not limited thereto.

[0174]

[0175] In the above chemical formula, Z 11 Selected from hydrogen, deuterium, halogen, siloxane, cyano, nitro, C1-C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 60 Heterocyclic group, C3~C 30 Aliphatic ring groups, and C3~C 30 Aliphatic ring and C6~C 30 The present invention relates to a group of fused rings formed by condensing aromatic rings, and adjacent groups can be combined with each other to form an aliphatic ring. Z1 and z2 are each an integer of 0 to 11, and z3 is an integer of 0 to 15.

[0176] The above Chemical Formula 41 can be expressed as the following Chemical Formula 40-1 or Chemical Formula 41-2.

[0177] <Chemical Formula 41-1> <Chemical Formula 41-2>

[0178] In the chemical formula 41-1 and the chemical formula 41-2, Ar 4 to Ar 7 、L 4 To L 7 Same as defined in Chemical Formula 41.

[0179] R 71 to R 73 independently selected from hydrogen, deuterium, halogen, siloxane, cyano, nitro, C1-C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, C1~C20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 60 Heterocyclic group, C3~C 30 Aliphatic ring groups, and C3~C 30 Aliphatic ring and C6~C 30 The present invention relates to a group of fused rings formed by condensing aromatic rings, and adjacent groups can be combined with each other to form an aliphatic ring. n4, b', c' are each an integer of 1 to 3.

[0180] The above Chemical Formula 41-1 can be expressed as the following Chemical Formula 40-1-1 or Chemical Formula 41-1-2.

[0181] <Chemical Formula 42-1-1> <Chemical Formula 42-1-2>

[0182] In the chemical formula 41-1-1 and the chemical formula 41-1-2, Ar 4 to Ar 7 、L 4 To L 7 Same as defined in Chemical Formula 41.

[0183] X 31 O, S, N (R 21 ) or C (R 22 )(R 22 ).

[0184] R 74 to R 77 、R 21 to R 23 independently selected from hydrogen, deuterium, halogen, siloxane, cyano, nitro, C1-C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30Arylthio, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 60 Heterocyclic group, C3~C 30 Aliphatic ring groups, and C3~C 30 Aliphatic ring and C6~C 30 The present invention relates to a group of fused rings formed by condensing aromatic rings, and adjacent groups may be combined to form an aliphatic ring. d' and e' are each an integer of 1 to 3, f' is an integer of 1 to 4, and g' is an integer of 1 to 2.

[0185] Specifically, the compound represented by 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 Chemical Formula 41 may be one of the following compounds P1-50 to P1-88, but is not limited thereto.

[0186]

[0187] The electron transport band region 220 may include an electron injection layer (EIL), an electron transport layer (ETL), a hole blocking layer (HBL), an electron transport auxiliary layer, etc., and may include at least one electron transport layer.

[0188] The electron transport band region 220 may include organic matter, inorganic matter, and organic-inorganic composites. The organic matter may be an organic compound with electronic properties, and the inorganic matter may be molybdenum oxide, tungsten oxide, nickel oxide, lithium halide, etc., but is not limited thereto.

[0189] The electron transport band domain 220 may include organic compounds and organometallic compounds, such as 1,4,5,8-naphthalenetetracarboxylic dianhydride (NTCDA), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), LiF, Alq3, Gaq3, Inq3, Znq2, Zn(BTZ)2, BeBq2, etc., but is not limited thereto.

[0190] The electron transport band 220 may include organic compounds and organometallic compounds, such as 1,4,5,8-naphthalenetetracarboxylic dianhydride (NTCDA), bathocuproine (BCP), LiF, Alq3, Gaq3, Inq3, Znq2, Zn(BTZ)2, BeBq2, etc., but is not limited thereto.

[0191] For example, the electron transport layer 220 may include a nitrous compound, and specifically, may include a compound represented by the following Chemical Formula 50 or Chemical Formula 51.

[0192] <Chemical Formula 50> <Chemical Formula 51>

[0193] In the above Chemical Formula 50 and Chemical Formula 51, each symbol can be defined as follows.

[0194] X a To X c represents N or C independently of each other (R 51 ), and at least one of them is N. Therefore, containing X a To X c The ring may be pyridine, pyrimidine or triazine.

[0195] X d Indicates O, S or N (R 52 ).

[0196] Ar 10 to Ar 13 Independently selected from C6~C60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing an aromatic ring of 30 A group consisting of alkyl groups.

[0197] L 10 To L 13 are independently selected from single bonds; C6~C 60 Arylene; Fluorenylene; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 and C2 to C3 containing at least one hetero atom selected from O, N, S, Si and P. 60 A group consisting of a heterocyclic group.

[0198] R 100 、R 51 and R 52 Independently selected from hydrogen; deuterium; halogen; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing the aromatic rings of 30 Alkyl; C2~C 30 Alkenyl; C2~C 30 Alkynyl; C1~C 30 Alkoxy; and C6~C 30 The adjacent groups may be combined with each other to form a ring. q is an integer of 1 to 4.

[0199] The aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic, condensed cyclic, alkyl, alkenyl, alkynyl, alkoxy, and aryloxy groups can be selected from deuterium, halogen, siloxane, cyano, nitro, C1-C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, C1~C 20 Alkylthio, C1~C20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 60 Heterocyclic group, C3~C 30 Aliphatic ring groups, and C3~C 30 Aliphatic ring and C6~C 30 The aromatic rings are fused to form a fused ring group, and the ....

[0200] The above Chemical Formula 50 can be expressed as any one of the following Chemical Formulas 50-1 to 50-3.

[0201] <Chemical Formula 50-1> <Chemical Formula 50-2>

[0202] <Chemical Formula 50-3>

[0203] In the Chemical Formulas 50-1 to 50-3, X a To X c 、Ar 11 、Ar 12 、L 10 To L 12 Same as defined in Chemical Formula 50.

[0204] X 31 and X 32 Independently of each other, they represent single bonds, O, S, N (R 53 )、C( 54 )(R 55 ) or Si (R 56 )(R 57 ), but excludes the case where all bonds are single.

[0205] Ar 14 、R 80 to R 84 、R 53 to R 57 Independently selected from hydrogen; deuterium; halogen; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing the aromatic rings of 30 Alkyl; C2~C 30 Alkenyl; C2~C 30 Alkynyl; C1~C 30 Alkoxy; and C6~C 30 The adjacent groups can be combined with each other to form a ring.

[0206] a5, c5, d5 and e5 are integers of 1 to 4 respectively, and b5 is an integer of 0 to 3.

[0207] Ar 15 It is C6~C 60 wherein a6 is an integer greater than or equal to 1.

[0208] The above Chemical Formula 50-1 can be expressed as the following Chemical Formula 50-1-1 or Chemical Formula 50-1-2.

[0209] <Chemical Formula 50-1-1> <Chemical Formula 50-1-2>

[0210] In the above Chemical Formula 50-1-1 and Chemical Formula 50-1-2, X a To X c 、Ar 11 、Ar 12 、L 10 To L 12 、X 31 、R 80 、R 81 The definitions of a5, b5 are the same as those in Chemical Formula 50-1, and R 101 and R 102 Respectively with R 54 and R 55 same.

[0211] Specifically, the compound represented by Chemical Formula 50 may be one of the following compounds P2-1 to P2-48, and the compound represented by Chemical Formula 51 may be one of the following compounds P2-49 to P2-76, but are not limited thereto.

[0212]

[0213] The organic optoelectronic device according to an embodiment of the present invention may be manufactured using various deposition methods.

[0214] Organic photovoltaic devices can be manufactured using deposition methods such as physical vapor deposition (PVD) or chemical vapor deposition (CVD). For example, a metal, conductive metal oxide, or alloy thereof can be deposited on a substrate to form the first electrode 110, followed by the formation of organic layers including the active layer 130, and finally, the material for the second electrode 120 can be deposited.

[0215] Furthermore, the active layer 130 is formed into a smaller number of layers using various polymer materials through solvent processing or solvent purification methods other than vapor deposition, such as spin coating, nozzle printing, inkjet printing, slit coating, dip coating, roll-to-roll processing, doctor blade coating, screen printing, or thermal transfer. Because the organic layer of the present invention can be formed using a variety of methods, the scope of protection of the present invention is not limited by the formation method.

[0216] The organic optoelectronic device according to an embodiment of the present invention may be applicable to organic solar cells, image sensors, photodetectors, photosensors, organic light-emitting devices, etc. In particular, the organic optoelectronic device of the present invention may be applicable to image sensors, etc.

[0217] Image sensors including these organic optoelectronic devices can detect light with wavelengths above 500 nm, preferably between 500 and 600 nm, and more preferably between 500 and 550 nm. Thus, they can selectively sense light in the green wavelength region and replace color filters for green pixels.

[0218] Another embodiment of the present invention may include an electronic device including the image sensor of the present invention. In this case, the electronic device may be a current or future wired or wireless communication terminal, and may include all types of electronic devices, including mobile phones and other mobile communication terminals, navigation devices, game consoles, various televisions, various computers, digital cameras, and electronic endoscopes.

[0219] The present invention is described in detail below by way of examples. The examples are only used to illustrate the present invention and should not limit the scope of the present invention.

[0220] [Synthesis example]

[0221] The compound (final product) represented by Chemical Formula 1 in the present invention can be prepared by the method shown in the following Reaction Formula 1, but is not limited to this method.

[0222] <Reaction Formula 1>

[0223] SubA synthesis example

[0224] SubA in Reaction Formula 1 can be synthesized through the reaction pathway of Reaction Formula 2 below, but is not limited thereto.

[0225] <Reaction Formula 2>

[0226] 1. Synthesis Example of SubA-3

[0227] (1) Synthesis of SubA-3-a

[0228] To 2-chloroaniline (50 g, 391.9 mmol) were added 2-bromothienoselenide (82.2 g, 391.9 mmol), P (dba (10.77 g, 11.8 mmol), P (t-Bu (4.7 g, 23.5 mmol), NaOt-Bu (75.33 g, 783.9 mmol) and toluene (1300 mL) were added and reacted. After the reaction was completed, the mixture was extracted with water and then precipitated with MgS The organic phase was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (83.5 g, yield: 83%).

[0229] (2) Synthesis of SubA-3-b

[0230] To SubA-3-a (80 g, 311.8 mmol) was added Pd(OAc (2.1 g, 9.4 mmol), P (t-Bu BH (5.4 g, 18.7 mmol), C (129.2 g, 935.3 mmol) and DMA (1000 mL) were reacted. After the reaction was completed, the product was extracted with water and MgS The organic layer was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (56.3 g, yield: 82%).

[0231] (3) Synthesis of SubA-3-c

[0232] Methyl 2-bromobenzoate (48.8 g, 227.1 mmol), copper iodide (21.6 g, 113.6 mmol), cesium carbonate (74.0 g, 227.1 mmol), ethylenediamine (6.8 g, 113.6 mmol) and toluene (450 mL) were added to SubA-3-b (50 g, 227.1 mmol) to carry out the reaction. After the reaction was completed, the mixture was extracted with water and eluted with MgS The organic layer was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (52.3 g, yield: 65%).

[0233] (4) Synthesis of SubA-3-d

[0234] Diethyl ether (700 mL) was added to SubA-3-c (50 g, 141.1 mmol) and stirred. A 1 M methyl-d3-magnesium iodide solution (564.5 mL) was slowly added dropwise to the mixture at 5°C and stirred for 1 hour. After the reaction was complete, the reaction mixture was poured into ice water and extracted with methyl chloride (MC). The organic layer was washed with MgS The concentrate was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (32.3 g, yield: 92%).

[0235] (5) Synthesis of SubA-3-e

[0236] SubA-3-d (37 g, 102.7 mmol) dissolved in toluene (510 mL) was slowly added dropwise to a mixture of polyphosphoric acid (116.5 g, 821.4 mmol) and methanesulfonic acid (78.9 g, 821.4 mmol). The mixture was stirred for 24 hours. After completion of the reaction, the reaction mixture was poured into ice water and neutralized with 10% aqueous NaOH. After extraction with methyl chloride (MC), the organic layer was washed with MgS The concentrate was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (19.0 g, yield: 54%).

[0237] (6) Synthesis of SubA-3

[0238] Phosphorus oxychloride (polyphosphoric acid) (17.4 g, 113.9 mmol) was added dropwise to DMF (32.0 g, 438.2 mmol) at -15°C, followed by stirring at room temperature for 2 hours. SubA-3-e (30 g, 87.6 mmol) was dissolved in MC (870 mL) and slowly added dropwise to the stirred mixture, followed by stirring at room temperature for 24 hours. After the reaction was completed, the solvent was removed at low temperature, and a 10% aqueous NaOH solution was added dropwise until the pH reached 14, followed by stirring at room temperature for 2 hours. After extraction with methyl chloride (MC), the organic layer was washed with MgS The concentrate was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (26.9 g, yield: 83%).

[0239] 2. Synthesis Example of SubA-5

[0240] (1) Synthesis of SubA-5-a

[0241] To 2,6-dibromoaniline (50 g, 199.3 mmol) were added 2-iodofuran (38.65 g, 199.3 mmol), P (dba (5.47 g, 6.0 mmol), P (t-Bu (2.4 g, 12.0 mmol), NaOt-Bu (38.3 g, 398.5 mmol) and toluene (600 mL) were reacted. After the reaction was completed, the mixture was extracted with water and MgS The organic layer was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (48.0 g, yield: 76%).

[0242] (2) Synthesis of SubA-5-b

[0243] To SubA-5-a (48 g, 151.4 mmol) was added Pd(OAc (1.0 g, 4.5 mmol), P (t-Bu BH (2.6 g, 9.1 mmol), C (62.7 g, 454.3 mmol) and DMA (5000 mL) were reacted. After the reaction was completed, the product was extracted with water and MgS The organic layer was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (28.6 g, yield: 80%).

[0244] (3) Synthesis of SubA-5-c

[0245] 1-Bromo-2-iodobenzene (32.3 g, 114.4 mmol), copper iodide (10.89 g, 57.2 mmol), cesium carbonate (37.2 g, 114.4 mmol), ethylenediamine (3.4 g, 57.2 mmol) and toluene (230 mL) were added to SubA-5-b (27 g, 114.4 mmol) to carry out the reaction. After the reaction was completed, the mixture was extracted with water and eluted with MgS The organic layer was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (33.5 g, yield: 75%).

[0246] (4) Synthesis of SubA-5-d

[0247] Diethyl ether (800 mL) was added to SubA-5-c (33.0 g, 84.4 mmol) and stirred. A 2.5 M n-butyllithium solution (67.5 mL) was slowly added dropwise to the reaction mixture at -78°C and stirred for 1 hour. Silicon tetrachloride (14.3 g, 84.4 mmol) was then slowly added dropwise and stirred at room temperature for an additional hour. After completion of the reaction, the solvent of the reaction mixture was concentrated and recrystallized to obtain the product (12.5 g, 45% yield).

[0248] (4) Synthesis of SubA-5-e

[0249] Diethyl ether (120 mL) was added to SubA-5-d (12.0 g, 36.3 mmol) and stirred. A 3M solution of methyl-d3-magnesium iodide (72.6 mL) was slowly added dropwise to the reaction mixture at 5°C and stirred for 24 hours. Upon completion of the reaction, the reaction mixture was poured into ice water and extracted with diethyl ether. The organic layer was dried over MgSO4 and concentrated. The concentrate was separated by silica gel column chromatography and recrystallized to obtain the product (9.7 g, 90% yield).

[0250] (6) Synthesis of SubA-5

[0251] exist Phosphorus oxychloride (6.0 g, 39.6 mmol) was slowly added dropwise to DMF (11.1 g, 152.3 mmol) at 15°C and stirred at room temperature for 2 hours. SubA-5-e (9.0 g, 30.5 mmol) was dissolved in MC (300 mL) and slowly added dropwise to the above mixture and stirred for 24 hours. After the reaction was completed, the solvent was removed at low temperature, the pH was adjusted to 14 with 10% NaOH aqueous solution, and stirred at room temperature for 2 hours. After extraction with methyl chloride, the organic layer was washed with MgS The concentrate was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (8.3 g, yield: 84%).

[0252] 3. Synthesis Example of SubA-7

[0253] (1) Synthesis of SubA-7-a

[0254] To carbazole (50 g, 299.0 mmol) was added methyl 2-bromothiophene-3-carboxylate (66.1 g, 299.0 mmol), copper iodide (28.4 g, 149.5 mmol), cesium carbonate (97.43 g, 299.0 mmol), ethylenediamine (8.9 g, 149.5 mmol) and toluene (600 mL) for reaction. After the reaction was completed, the mixture was extracted with water and eluted with MgS The organic layer was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (37.7 g, yield: 41%).

[0255] (4) Synthesis of SubA-7-b

[0256] Diethyl ether (600 mL) was added to SubA-7-a (37 g, 120.4 mmol) and stirred. 1 M methyl-d3-magnesium iodide solution (481.5 mL) was slowly added dropwise to the reaction mixture at 5°C and stirred for 1 hour. After the reaction was complete, the reaction mixture was poured into ice water and extracted with methyl chloride (MC), followed by MgS The organic layer was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (35.8 g, yield: 95%).

[0257] (5) Synthesis of SubA-7-c

[0258] SubA-7-b (35.0 g, 111.7 mmol) dissolved in toluene (550 mL) was slowly added dropwise to a mixture of polyphosphoric acid (126.7 g, 893.3 mmol) and methanesulfonic acid (85.8 g, 893.3 mmol) and stirred for 24 hours. After the reaction was complete, the reaction mixture was poured into ice water and neutralized with 10% aqueous sodium hydroxide solution. After extraction with methyl chloride (MC), the mixture was washed with MgS The organic layer was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (17.5 g, yield: 53%).

[0259] (6) Synthesis of SubA-7

[0260] Polyphosphoryl chloride (11.4 g, 74.8 mmol) was slowly added dropwise to DMF (21.0 g, 287.7 mmol) at -15°C and stirred at room temperature for 2 hours. SubA-7-c (17 g, 57.5 mmol) was dissolved in methyl chloride (570 mL) and slowly added dropwise to the above mixture, stirring at room temperature for 24 hours. After the reaction was completed, the solvent was removed at low temperature, and 10% NaOH aqueous solution was added dropwise to a pH of 14, and stirred at room temperature for 2 hours. After extraction with MC, the organic layer was washed with MgS The concentrate was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (15.8 g, yield: 85%).

[0261] 4. Synthesis Example of SubA-16

[0262] (1) Synthesis of SubA-16-a

[0263] 9,9-dimethyl-9,10-dihydroacridine (50 g, 238.9 mmol) was mixed with methyl 2-bromothiophene-3-carboxylate (52.8 g, 238.9 mmol), copper iodide (22.7 g, 119.5 mmol), cesium carbonate (77.8 g, 238.9 mmol), ethylenediamine (7.1 g, 119.5 mmol) and toluene (480 mL) for reaction. After the reaction was completed, the mixture was extracted with water and the organic layer was washed with MgS The product was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (32.6 g, yield: 39%).

[0264] (4) Synthesis of SubA-16-b

[0265] SubA-16-a (32.0 g, 91.6 mmol) was added to diethyl ether (460 mL) and stirred. 1 M methyl-d3-magnesium iodide solution (366.2 mL) was slowly added dropwise at 5°C. After the addition was complete, the mixture was stirred for another hour. After the reaction was complete, the reaction mixture was poured into ice water and extracted with methyl chloride. The organic layer was washed with MgS The product was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (30.3 g, yield: 93%).

[0266] (5) Synthesis of SubA-16-c

[0267] SubA-16-b (30.0 g, 84.4 mmol) dissolved in toluene (420 mL) was slowly added dropwise to a mixture of polyphosphoric acid (95.8 g, 675.0 mmol) and methanesulfonic acid (64.8 g, 675.0 mmol). The mixture was stirred for 24 hours. After completion of the reaction, the reaction mixture was poured into ice water and neutralized with 10% aqueous NaOH. The organic layer was extracted with methyl chloride and washed with MgS The concentrate was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (15.1 g, yield: 53%).

[0268] (6) Synthesis of SubA-16

[0269] exist At 15°C, polyphosphoric acid (8.8 g, 57.8 mmol) was slowly added dropwise to N,N-dimethylformamide (DMF, 16.2 g, 222.2 mmol) and stirred at room temperature for 2 hours. SubA-16-c (15.0 g, 44.4 mmol) was dissolved in methyl chloride (MC, 440 mL) and slowly added dropwise to the above mixture, stirring at room temperature for 24 hours. After the reaction was completed, the solvent was removed at low temperature, and 10% aqueous NaOH was added dropwise to a pH of 14, and stirred at room temperature for 2 hours. After extraction with methyl chloride, the organic layer was washed with MgS The concentrate was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (13.8 g, yield: 85%).

[0270] 5. Synthesis Example of SubA-49

[0271] (1) Synthesis of SubA-49-a

[0272] Methyl 2-bromofuran-3-carboxylate (41.1 g, 200.5 mmol), copper iodide (19.0 g, 100.3 mmol), cesium carbonate (65.3 g, 200.5 mmol), ethylenediamine (6.0 g, 100.3 mmol) and toluene (400 mL) were added to 10H-spiro[acridine-9,1'-cyclohexane] (50 g, 200.5 mmol) to carry out the reaction. After the reaction was completed, the mixture was extracted with water and eluted with MgS The organic layer was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (32.2 g, yield: 43%).

[0273] (4) Synthesis of SubA-49-b

[0274] Diethyl ether (420 mL) was added to SubA-49-a (32.0 g, 85.7 mmol) and stirred. 1 M methyl-d3-magnesium iodide solution (342.7 mL) was slowly added dropwise to the reaction mixture at 5°C and stirred for 1 hour. After the reaction was complete, the reaction mixture was poured into ice water and extracted with methyl chloride (MC), followed by MgS The organic layer was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (29.6 g, yield: 91%).

[0275] (5) Synthesis of SubA-49-c

[0276] SubA-49-b (29.0 g, 76.4 mmol) dissolved in toluene (380 mL) was slowly added dropwise to a mixture of polyphosphoric acid (86.77 g, 611.3 mmol) and methanesulfonic acid (58.7 g, 611.3 mmol). The mixture was stirred for 24 hours. After completion of the reaction, the reaction mixture was poured into ice water and neutralized with 10% aqueous NaOH. The organic layer was extracted with methyl chloride (MC) and washed with MgS The concentrate was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (14.1 g, yield: 51%).

[0277] (6) Synthesis of SubA-49

[0278] Polyphosphoric acid (7.7 g, 50.3 mmol) was slowly added dropwise to N,N-dimethylformamide (DMF, 14.1 g, 193.6 mmol) at -15°C and stirred at room temperature for 2 hours. SubA-49-c (14.0 g, 38.7 mmol) was dissolved in methyl chloride (MC, 380 mL) and slowly added dropwise to the above mixture, stirring at room temperature for 24 hours. After the reaction was complete, the solvent was removed at low temperature, and 10% aqueous NaOH was added dropwise to a pH of 14, and stirred at room temperature for 2 hours. After extraction with methyl chloride, the organic layer was washed with MgS The concentrate was dried and concentrated, and the concentrate was separated by silica gel column and recrystallized to obtain the product (12.7 g, yield: 84%).

[0279] Compounds belonging to SubA may include, but are not limited to, the following compounds. Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of these compounds.

[0280]

[0281] [Table 1]

[0282] SubB synthesis example

[0283] SubB in the above reaction formula 1 can be synthesized as follows, but is not limited thereto.

[0284] 1. Synthesis Example of SubB-1

[0285] To a reaction mixture of 1H,3H-thieno[3,4-c]furan-1,3-dione (20 g, 129.8 mmol) and acetic anhydride (132.4 g, 1297.5 mmol) were added triethylamine (26.2 g, 259.5 mmol) and ethyl acetoacetate (18.5 g, 142.7 mmol). The mixture was stirred at 65°C for 24 hours. After completion of the reaction, the reaction mixture was poured into ice water, extracted with methyl chloride, and concentrated. Hydrochloric acid was then added, the mixture was stirred at 70°C for 1 hour, cooled to room temperature, and extracted again with methyl chloride. The organic layer was dried over MgSO4 and concentrated. The concentrate was then separated by silica gel column chromatography and recrystallized to yield the product (11.8 g, 60% yield).

[0286] 2. Synthesis Example of SubB-18

[0287] Using naphtho[2,3-c]furan-1,3-dione (20 g, 100.9 mmol) instead of 1H,3H-thieno[3,4-c]furan-1,3-dione, the synthesis was carried out in the same manner as in the SubB-1 synthesis example to obtain the product (12.7 g, yield: 64%).

[0288] 3. Synthesis Example of SubB-14

[0289] 1H-indene-1,3(2H)-dione (25 g, 171.1 mmol) and malononitrile (33.9 g, 513.2 mmol) were added to ethanol (430 mL) and stirred for 30 minutes. Sodium acetate (18.2 g, 222.4 mmol) was then added and stirred for 1 hour. Upon completion of the reaction, the reaction mixture was slowly poured into water, and HCl was added dropwise until the pH reached 1-2. The precipitate was filtered, washed with water, separated on a silica gel column, and recrystallized to yield the product (11.6 g, 35% yield).

[0290] 4. Synthesis Example of SubB-34

[0291] Malonic acid (15 g, 144.1 mmol) and 1,3-dimethylurea (12.7 g, 144.1 mmol) were dissolved in a reaction mixture of acetic acid (290 mL). Acetic anhydride (29.4 g, 288.3 mmol) was slowly added, and the mixture was stirred at 70°C for 20 hours. After completion of the reaction, the solvent was removed, and the mixture was extracted with water and ethyl acetate. The mixture was concentrated and recrystallized at low temperature to obtain the product (16.2 g, 72% yield).

[0292] Compounds belonging to SubB may include, but are not limited to, the following compounds, and Table 2 shows the FD-MS (field desorption mass spectrometry) values ​​of these compounds.

[0293]

[0294] [Table 2]

[0295] Synthesis example of the final compound

[0296] 1. Synthesis Example of P1

[0297] SubB-2 (4.2 g, 30.9 mmol) and THF (150 mL) were added to SubA-1 (10 g, 30.9 mmol) and reacted at 80°C for 12 hours. After completion of the reaction, the solvent was removed, and the reaction product was recrystallized to obtain the product (11.6 g, 85% yield).

[0298] 2. Synthesis Example of P14

[0299] SubB-34 (4.92 g, 31.5 mmol) and THF (160 mL) were added to SubA-7 (10 g, 31.5 mmol), and the product (12.6 g, yield: 88%) was obtained by the same method as in Example P1.

[0300] 3. Synthesis Example of P27

[0301] SubB-1 (3.6 g, 23.8 mmol) and THF (120 mL) were added to SubA-15 (10 g, 23.8 mmol), and the product (11.0 g, yield: 84%) was obtained by the same method as in Example P1.

[0302] 4. Synthesis Example of P29

[0303] SubB-14 (5.4 g, 28.1 mmol) and THF (140 mL) were added to SubA-14 (10 g, 28.1 mmol). The product (12.4 g, yield: 83%) was obtained by the same method as in Example P1.

[0304] 5. Synthesis Example of P43

[0305] SubB-35 (3.4 g, 20.1 mmol) and THF (100 mL) were added to SubA-43 (8 g, 20.1 mmol) and the product (9.1 g, yield: 82%) was obtained using the same method as in Example P1.

[0306] The FD-MS (field desorption-mass spectrometry) values ​​of the compounds P1 to P69 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[0307] [Table 3]

[0308] In addition, although the synthesis examples of the present invention represented by Chemical Formula 1 are described above, these are based on Suzuki cross-coupling reactions, Miyaura boration reactions, triphenylphosphine-mediated reductive cyclization reactions (PPh3-mediated reductive cyclization reactions (J.Org.Chem. 2005, 70, 5014.), Buchwald-Hartwig cross coupling reactions, etc. Those skilled in the art can easily understand that in addition to the substituents explicitly shown in the specific synthesis examples, the reactions can also proceed even if other substituents defined in Chemical Formula 1 are used for bonding. Bond dissociation energy is used to calculate the bond energy of the acyclic bond within the molecule. To this end, the electric potential energy of the target molecule is calculated, and the electric potential energy of each free radical molecule is calculated based on the acyclic bond. The bond dissociation energy can be expressed as follows.

[0309]

[0310] All calculations were performed assuming an electrically neutral state. In the case of solid-phase molecules extracted by molecular dynamics simulation, unlike gas-phase molecules, they do not have an optimal structure, so all calculations were performed with single-point energy ( Single-point energy, SPE) calculations were performed to calculate bond dissociation energies while maintaining the structure.

[0311]

[0312] Unless otherwise specified, the term "average bond dissociation energy in the amorphous solid phase ( Average Bond-dissociation energy in solid state amorphous)" refers to the quantum-mechanical average bond energy of molecules in molecular dynamics simulated solid-state amorphous.

[0313] The average bond dissociation energy in the amorphous solid phase is a statistical data set (a collection of multiple energy values), and therefore its value can be quantified in different ways depending on the data processing method. Therefore, in this specification, for quantification, the average value of the bond dissociation energy distribution in the amorphous solid phase, which has high statistical reliability due to the large number of samples and clearly shows the differences in properties between substances, is used. This value is calculated using the following process.

[0314] The average bond dissociation energy in an amorphous solid phase is a value derived by performing molecular dynamics simulation on a certain number of monomer molecules arranged in a unit cell with periodic boundary conditions (PBC). Preferably, the number of monomer molecules in a unit cell can range from tens to thousands.

[0315] Molecular dynamics simulations are conducted in four stages. The first stage is based on Brownian mechanics, performed under a fixed volume and at a temperature of 10 Kelvin. The second stage is also based on Brownian mechanics, but at a fixed atmospheric pressure (1.01325 bar) and a temperature of 100 Kelvin. In the third stage, molecular dynamics calculations are performed using force fields, also under fixed pressure (atmospheric pressure) and temperature (room temperature) for 0.1 nanoseconds (ns). Finally, under the same conditions as the third stage (atmospheric pressure, room temperature), molecular dynamics calculations are performed in 2-femtosecond (fs) increments until the desired predetermined time is reached. The predetermined time refers to the time it takes for the amorphous solid structure to reach full equilibrium, preferably ranging from hundreds to thousands of nanoseconds, more preferably from 100 to 150 nanoseconds, and even more preferably from 120 nanoseconds. Structural data at the final time point are then extracted, and a portion of the monomer molecules are sampled from the corresponding structure. For monomer molecules extracted by quantum mechanics simulation, single-point energy calculation is performed, and the bond dissociation energy (BDE) of the acyclic bond in the molecule is calculated. All the obtained bond dissociation energy values ​​are taken to form the bond dissociation energy set G={E1.....E N}, the average value of the bond dissociation energy set Used as an indicator of bond dissociation energy of solid substances.

[0316] In this specification, the average bond dissociation energy value in the amorphous solid phase is The unit is eV, which can be converted to kcal / mol by multiplying the eV value by 23.061.

[0317] Unless otherwise specified, the term "volume density of amorphous solid phase molecular structure ( Bulk density of solid-state amorphous ) " , which refers to the volume density of the amorphous solid phase molecular structure obtained by molecular dynamics simulation ( Bulk density of Molecular Dynamically simulated solid- state amorphous ), find its value through the following process.

[0318] The average bond dissociation energy in the amorphous solid phase is a value derived by arranging a certain number of monomer molecules in a unit cell with periodic boundary conditions (PBC) and performing molecular dynamics simulation on this. Preferably, the number of monomer molecules in the unit cell can range from tens to thousands.

[0319] Molecular dynamics simulations are conducted in four stages. The first stage is based on Brownian mechanics, performed under a fixed volume and at a temperature of 10 Kelvin. The second stage is also based on Brownian mechanics, but is performed at a fixed atmospheric pressure (1.01325 bar) and a temperature of 100 Kelvin. Subsequently, in the third stage, molecular dynamics calculations are performed using force fields, also under fixed pressure (atmospheric pressure) and temperature (room temperature) for 0.1 nanoseconds (ns). Finally, under the same conditions as the third stage (atmospheric pressure, room temperature), the molecular dynamics process is repeated in 2 femtosecond (fs) increments until the desired predetermined time is reached. The predetermined time refers to the time it takes for the amorphous solid structure to reach a fully equilibrium state, and can preferably range from hundreds to thousands of nanoseconds, more preferably from 100 to 150 nanoseconds, and even more preferably from 120 nanoseconds. Then, the average bulk density of the final 20% of the time period is calculated. The final 20% of the time period may preferably be tens of nanoseconds to thousands of nanoseconds, more preferably 80 nanoseconds to 150 nanoseconds, and even more preferably 120 nanoseconds.

[0320] In this specification, the unit of the volume density of amorphous solid phase molecular structure is g / cm 3 .

[0321] The term "Radial Distribution Function (RDF, g(r))" used in this specification means that the radial distribution function (RDF) can be found at a certain distance from a molecule. r The radial distribution function is presented as a function of distance and is defined as follows.

[0322]

[0323] In the chemical formula, ρ is the bulk density, dr is the microthickness of a sphere with radius r, and dn ris the number of molecules contained in a spherical shell with a micro-thickness of dr. To quantify the radial distribution function, in the amorphous solid phase, the distance at which the radial distribution function reaches its maximum value is used as an indicator. In this case, the center-of-mass distance of each molecule is used as the intermolecular distance r. The amorphous solid phase structure used to obtain the radial distribution function can be determined through molecular dynamics simulation. In this case, only the structure of the final 20% of the total simulation time is used to calculate the distribution function. The final 20% of time preferably ranges from tens of nanoseconds to thousands of nanoseconds, more preferably from 80 nanoseconds to 150 nanoseconds, and even more preferably from 120 nanoseconds.

[0324] In this specification, the unit of the radial distribution function value is .

[0325] The average bond dissociation energy, volume density, and radial distribution function values ​​for the amorphous solid phase described in this specification were obtained through molecular simulation (Gaussian 09 Rev. C.01, Schrodinger MaestroMaterials Science Suite 4.8.132). Molecular dynamics simulations were performed using the Desmond package. From the structures obtained through molecular dynamics simulations, individual molecules were extracted and their quantum chemical properties were calculated based on first-principles calculations using the Gaussian and Jaguar packages.

[0326] Regarding charge mobility, in the generalized effective medium model (GEMM), the charge mobility for a homogeneous medium can be obtained from the analytical solution of the master equation based on the effective medium approximation, as shown below.

[0327]

[0328] Where e is the charge, β is a thermodynamic constant given by the Boltzmann constant and the inverse of temperature (1 / KgT), M is the average number of nearest-neighbor molecules, and H abis the charge transfer matrix element, n is the charge transfer dimension (n=3 in a three-dimensional system), h is Planck's constant, λ is the reorganization energy, σ is the disorder parameter, and C is the calibration constant. Therefore, the charge mobility has the following proportional relationship.

[0329]

[0330] Assuming that the molecular distribution in the amorphous solid state is sufficiently uniform (σ<<1), the charge transfer matrix element (H ab ) is constant, so the above proportional formula can be expressed as follows.

[0331]

[0332] At this time, it is known a priori that the charge transfer matrix element has the following proportional relationship with the intermolecular distance.

[0333]

[0334] Here, η is the decay constant and r is the distance between molecules. Therefore, for a uniform medium, charge mobility decays exponentially with respect to the distance between molecules, showing a trend of increasing charge mobility as the distance between molecules decreases.

[0335] Furthermore, since the bulk density is inversely proportional to the volume (ρ∝1 / V), it can be used to derive the average intermolecular distance ( ), the smaller the volume density, the shorter the distance between molecules, which means that substances with low volume density can have high charge mobility.

[0336] Therefore, in the amorphous solid phase structure obtained by molecular dynamics simulation, by calculating the radial distribution function, the range where the distance between molecules is most densely distributed can be identified, and the peak position of the radial distribution function can be used as an indicator of the intermolecular distance for comparing charge mobility.

[0337] Table 4 below shows the bond dissociation energy (BDE) of the compound P-13 of the present invention and the comparative compound 1 below, measured using molecular simulation (Gaussian 09 Rev. C.01, Schrodinger MaestroMaterials Science Suite 4.8.132).

[0338] <Comparative Compound 1>

[0339] The BDE shown in Table 4 below is the result of measurement in the oxidation state (where electrons are released from the molecule), the neutral state (where electrons are bound to the molecule), and the reduction state (where electrons are bound to the molecule). Therefore, it is estimated that the higher the BDE, the higher the structural stability.

[0340] [Table 4]

[0341] Table 4 shows that the overall BDE value of Compound P-13 of the present invention is higher than that of Comparative Compound 1. In organic electrochemical devices, lower film crystallinity leads to a more amorphous state. This amorphous state, through its isotropic and homogeneous properties, reduces grain boundaries and improves charge and hole mobility.

[0342] However, even in the same amorphous state, the quantum mechanical BDE of the amorphous solid-phase molecules varies depending on the molecular structure due to the intermolecular interactions in the solid phase. The higher the BDE value, the more stable the compound itself.

[0343] Therefore, compared with the use of the comparative compound 1, when the compound P-13 of the present invention is used as the p-type semiconductor compound of the organic photoelectric device, the structural stability is significantly improved, and the heat resistance of the device can be maximized.

[0344] The above description is only an exemplary description of the present invention. For those skilled in the art of the present invention, various modifications can be made without departing from the essential features of the present invention. Therefore, the embodiments disclosed in this specification are not intended to limit the present invention, but are for illustrative purposes only, and the spirit and scope of the present invention should not be limited by these embodiments. The scope of protection of the present invention should be interpreted according to the scope of protection claimed in the invention, and all technologies within the scope equivalent to it should be interpreted as included in the scope of rights of the present invention.

Claims

1. A compound represented by the following chemical formula 1, wherein: <Chemical Formula 1> In the chemical formula 1, X 1 and X 2 are independently single bonds, C(R a )(R b ) or Si (R c )(R d ), where X 1 and X 2 At least one of them is C (R a )(R b ) or Si (R c )(R d ), a and b are each 0 or 1, wherein a+b is 1 or 2, R a 、R b 、R c and R d Independently selected from hydrogen; deuterium; halogen; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing the aromatic rings of 30 Alkyl; C2~C 30 Alkenyl; C2~C 30 Alkynyl; C1~C 30 Alkoxy; and C6~C 30 The group is composed of aryloxy groups, and R a and R b Between groups, R c and R d The groups can combine with each other to form a ring, where R a 、R b 、R c and R d at least one of which contains deuterium, X 3 is O, S, Se or Te, Ar is C6~C 60 or a C2-C 60 wherein Ar is selected from C=O, C=S, C=Se, C=Te, CN and C One or more functional groups in the group consisting of R 1 to R 4 Independently selected from hydrogen; deuterium; halogen; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group formed by condensing the aromatic rings of 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; and C6~C 60 The aryloxy group is composed of adjacent R 1 Between groups, adjacent R 2 The groups can combine with each other to form rings. x is an integer from 0 to 4, y is an integer from 0 to 5, The aryl, fluorenyl, heterocyclic, aliphatic, condensed, carbocyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent R 1 Between groups, adjacent R 2 Between groups, R a and R b Between groups, or R c and R d The ring formed by the mutual combination of groups can be selected from deuterium, halogen, siloxane, cyano, nitro, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 60 Heterocyclic group, C3~C 20 Aliphatic ring groups, and C3~C 30 Aliphatic ring and C6~C 30 The aromatic rings are fused to form a fused ring group, and the ....

2. The compound according to claim 1, wherein The above Chemical Formula 1 is represented by one of the following Chemical Formulas 2 to 4, <Chemical Formula 2> <Chemical Formula 3> <Chemical Formula 4> In the chemical formulas 2 to 4, X 1 To X 3 、R 1 to R 4 , Ar is the same as defined in claim 1, m is an integer from 0 to 3, n and m' are each an integer from 0 to 4, and n' is an integer from 0 to 5.

3. The compound according to claim 1, wherein The above Chemical Formula 1 is represented by one of the following Chemical Formulas 5 to 12, <Chemical Formula 5> <Chemical Formula 6> <Chemical Formula 7> <Chemical Formula 8> <Chemical Formula 9> <Chemical Formula 10> <Chemical Formula 11> <Chemical Formula 12> In the chemical formulas 5 to 12, X 3 、R 1 to R 4 、R a to R d , Ar is the same as defined in claim 1, m is an integer from 0 to 3, and n is an integer from 0 to 4.

4. The compound according to claim 1, wherein The above Chemical Formula 1 is represented by the following Chemical Formula 13 or Chemical Formula 14, <Chemical Formula 13> <Chemical Formula 14> In the chemical formula 13 and the chemical formula 14, X 3 、R 1 to R 4 、R a to R d , Ar is the same as defined in claim 1, m' is an integer from 0 to 4, and n' is an integer from 0 to 5.

5. The compound according to claim 1, wherein The above Chemical Formula 1 is represented by the following Chemical Formula 15 or Chemical Formula 16, <Chemical Formula 15> <Chemical Formula 16> In the chemical formula 15 and the chemical formula 16, X 3 、R 1 to R 4 、R a to R d , Ar are the same as defined in claim 1, and m' and n are each an integer from 0 to 4.

6. The compound according to claim 1, wherein R a and R b The groups can combine to form a ring, or R c and R d The groups may combine with each other to form a ring.

7. The compound according to claim 1, wherein Ar is selected from the group consisting of the following Chemical Formulas 17 to 19, <Chemical Formula 17> <Chemical Formula 18> <Chemical Formula 19> In the Chemical Formulas 17 to 19, Indicates the bonding site, Z 1 to Z 7 independently selected from O, S, Se, Te and C (R e )(R f ), R e and R f independently selected from hydrogen; deuterium; halogen; cyano; and substituted or unsubstituted C1-C 20 The alkyl group, Y 1 To Y 4 Independently selected from O, S, Se, Te, C (R g )(R h ) and N (R i ), R g 、R h and R i independently selected from hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C 20 Alkyl; and substituted or unsubstituted C2~C 20 The group consisting of alkenyl groups, Y 5 and Y 6 are independently N or C (R j ), R j independently selected from hydrogen, deuterium, halogen, siloxane, cyano, nitro, C1-C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 60 Heterocyclic group, C3~C 30 Aliphatic ring groups, and C3~C 30 Aliphatic ring and C6~C 30 The aromatic rings are fused to form a fused ring group, and the adjacent R j The groups may combine with each other to form a ring.

8. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is any one of the following compounds, 。 9. The compound according to claim 1, characterized in that The compound has a maximum absorption wavelength in the range of 500 to 600 nm in a thin film state.

10. An organic photoelectric device comprising a first electrode, a second electrode, and an active layer between the first electrode and the second electrode, characterized in that: The active layer comprises the compound of claim 1.

11. The compound according to claim 10, characterized in that The active layer includes a p-type semiconductor compound and an n-type semiconductor compound, and the p-type semiconductor compound is the compound according to claim 1.

12. An image sensor comprising the organic optoelectronic device according to claim 10.

13. An electronic device comprising the image sensor of claim 12.

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