Near-infrared absorbing materials, near-infrared absorbing / blocking films, and photoelectric elements, as well as organic sensors and electronic devices.

Abstract

To provide near-infrared absorbers having excellent near-infrared absorbing characteristics.SOLUTION: Near-infrared absorbers include compounds represented by the following chemical formula 1.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to near-infrared (NIR) absorbing materials, near-infrared absorbing / blocking films, photoelectric elements, organic sensors, and electronic devices, and more particularly to near-infrared absorbing materials, near-infrared absorbing / blocking films, photoelectric elements, organic sensors, and electronic devices that exhibit excellent near-infrared absorption characteristics. [Background technology]

[0002] Digital cameras and camcorders use image sensors to capture images and store them as electrical signals. These image sensors include a sensor that decomposes incident light by wavelength and converts each component into an electrical signal.

[0003] In recent years, the development of near-infrared absorbing materials with excellent absorption characteristics in the near-infrared region, as well as photoelectric elements or organic sensors containing them, has become a challenge in order to improve the sensitivity of sensors in low-light environments and to use sensors as biorecognition devices. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2009-205029 [Overview of the project] [Problems that the invention aims to solve]

[0005] The present invention has been made in view of the problems with the above-mentioned conventional near-infrared absorbing materials, and the object of the present invention is to provide a near-infrared absorbing material with excellent near-infrared absorption characteristics.

[0006] Another object of the present invention is to provide a film containing the near-infrared absorbing material of the present invention, and a photoelectric element containing the near-infrared absorbing material of the present invention. Another object of the present invention is to provide an organic sensor including the near-infrared absorber of the present invention or the optoelectronic device of the present invention, and an electronic device including the optoelectronic device of the present invention or the organic sensor of the present invention.

Means for Solving the Problems

[0007] The near-infrared absorber according to the present invention made to achieve the above object is a near-infrared absorber, characterized by including a compound represented by Chemical Formula 1 shown below.

Chem.

[0008] In the above chemical formula 1, Ar is preferably a benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetracene ring, or a substituted or unsubstituted pyrene ring. In the above chemical formula 1, Ar is preferably a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted quinazoline ring, or a substituted or unsubstituted phenanthroline ring.

[0009] In the aforementioned chemical formula 1, Ar is preferably one of the moieties represented by the chemical formula group A-1 shown below. [ka] (Among the chemical formulas in group A-1 above, Each hydrogen atom in the aromatic ring can be replaced with a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, a silyl group, or a C1-C10 alkylsilyl group, and an adjacent pair of * atoms within the aromatic ring are -NX of chemical formula 1. 1 -N-containing ring, and -N=X in chemical formula 1 2 =This is the part that bonds with the N-containing ring, The asterisks (*) in the left and right linking groups are Ar in chemical formula 1. 1 and Ar 2 This is the part that connects to it.

[0010] In the aforementioned chemical formula 1, Ar is preferably one of the moieties represented by the chemical formula group A-2 shown below. [ka] (In the above chemical formula group A-2, the hydrogen atoms of each aromatic ring can be substituted with a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, a silyl group, or a C1-C10 alkylsilyl group.) The adjacent pair of * inside the aromatic ring is -NX in chemical formula 1. 1 -N-containing ring and -N=X in chemical formula 1 2 =This is the part that bonds with the N-containing ring, The asterisks (*) in the left and right linking groups are Ar in chemical formula 1. 1 and Ar 2is a part to be connected.)

[0011] In the above Chemical Formula 1, X 2 is CR xx -CR yy When it is, R xx and R yy The aromatic ring formed by being connected to each other is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted acenaphthene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetracene ring or a substituted or unsubstituted pyrene ring. In the above Chemical Formula 1, X 2 is CR xx -CR yy When it is, R xx and R yy The aromatic ring formed by being connected to each other is preferably a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted quinazoline ring, a substituted or unsubstituted phenanthroline ring, a substituted or unsubstituted pyrimidine ring or a substituted or unsubstituted benzodithiophene ring.)

[0012] In the above Chemical Formula 1, X 2 is CR xx -CR yy When it is, R xx and R yy The aromatic ring formed by being connected to each other is preferably one of the moieties represented by the following Chemical Formula Group B-1.)

Chemical formula

[0013] In the above chemical formula 1, X 2 CR xx -CR yy If R xx and R yy The aromatic ring formed by the linkage of these elements is preferably one of the moieties represented by chemical formula group B-2 shown below. [ka] (Among the chemical formulas in group B-2 above, Each aromatic ring's hydrogen can be substituted with a halogen, a cyano group, a C1-C30 alkyl group, a C1-C30 alkoxy group, a C1-C30 haloalkyl group, -SiH3, a C1-C30 alkylsilyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, or a C3-C30 heteroaryl group. The asterisk inside the aromatic ring is CR. xx -CR yy This is the part that bonds with carbon.

[0014] In the above chemical formula 1, X 2 CR xx -CR yy If R xx and R yy The aromatic ring formed by the linkage of these elements is preferably one of the moieties represented by chemical formula B-3-1 or chemical formula B-3-2 shown below. [ka] [ka] (In the above chemical formulas B-3-1 and B-3-2, Ar 11 and Ar 12 These are, independently, substituted or unsubstituted carbon atoms with 6 to 30 carbon atoms. andsubstituted or unsubstituted heteroelements with 3 to 30 carbon atoms N They were selected, Z in chemical formula B-3-1 1 and Z 2 Each of them operates independently, CR a or N (where R a (These are hydrogen, deuterium, C1-C30 alkyl groups, C1-C30 haloalkyl groups, -SiH3, C1-C30 alkylsilyl groups, -NH2, C1-C30 alkylamine groups, C6-C30 arylamine groups, C6-C30 aryl groups, C6-C30 aryloxy groups, C3-C30 heteroaryl groups, halogens, cyano groups, or combinations thereof), Each aromatic ring's hydrogen can be substituted with a halogen, a cyano group, a C1-C30 alkyl group, a C1-C30 alkoxy group, a C1-C30 haloalkyl group, -SiH3, a C1-C30 alkylsilyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, or a C3-C30 heteroaryl group. The asterisk inside the aromatic ring is CR. xx -CR yy This is the part that bonds with carbon.

[0015] The moiety represented by the chemical formula B-3-1 is preferably represented by the chemical formula group B-3-11 shown below, and the moiety represented by the chemical formula B-3-2 is preferably represented by the chemical formula group B-3-21 shown below. [ka] (Among the chemical formulas in group B-3-11 above, Each aromatic ring's hydrogen can be substituted with a halogen, a cyano group, a C1-C30 alkyl group, a C1-C30 alkoxy group, a C1-C30 haloalkyl group, -SiH3, a C1-C30 alkylsilyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, or a C3-C30 heteroaryl group. The asterisk inside the aromatic ring is CR. xx -CR yy This is the part that bonds with carbon. [Chemical formula] (In the above chemical formula group B-3-21, the hydrogen of each aromatic ring can be substituted with a halogen, a cyano group, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, -SiH3, an alkylsilyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms, X a and X b are each independently O, S, Se, Te, NR a , SiR b R c and GeR d R e selected from (where R a R b R c R d and R e are each independently selected from hydrogen, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms). The * within the aromatic ring is the part that binds to the carbon of CR xx -CR yy .)

[0016] In the above chemical formula 1, Ar 1 and Ar 2 are preferably the same or different and are selected from the following chemical formula C-1-1 to chemical formula C-1-3. [Chemical formula] [Chemical formula] [Chemical formula] (Among the above chemical formulas C-1-1 to C-1-3, Each aromatic ring's hydrogen can be substituted with a halogen, a cyano group, a C1-C30 alkyl group, a C1-C30 alkoxy group, a C1-C30 haloalkyl group, -SiH3, a C1-C30 alkylsilyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, or a C3-C30 heteroaryl group. Y 1 O, S, Se, Te, S(=O), S(=O)², NR a1 , SiR b1 R c1 , or GeR d1 R e1 (Here, R a1 , R b1 , R c1 , R d1 , and R e1 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. Y 2 O, S, Se, Te, S(=O), S(=O)², NR a2 , SiR b2 R c2 , GeR d2 R e2 , or CR f2 R g2 (Here, R a2 , R b2 , R c2 , R d2 , R e2 , R f2 , and R g2is, independently of each other, hydrogen, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH3, an alkylsilyl group having 1 to 10 carbon atoms, -NH3, an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), R b1 and R c1 、R d1 and R e1 、R b2 and R c2 、R d2 and R e2 、and R f2 and R g2 exist independently of each other or are bonded to each other to form a spiro ring, * present outside at least one aromatic ring is the connection point with Ar in Chemical Formula 1, and * present inside at least one aromatic ring is R in Chemical Formula 1 1 including the N(R 1 )-containing ring, and the connection point with the N(R 2 )-containing ring of Chemical Formula 1 including R 2 ).)

[0017] In the above Chemical Formula 1, Ar 1 and Ar 2 are the same or different, and are preferably selected from Chemical Formula C-2-1 to Chemical Formula C-2-4 shown below.

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

[0018] In the above chemical formula 1, Ar 1 and Ar 2 These are either the same or different, and are preferably selected from the chemical formulas C-3-1 to C-3-6 shown below. [ka] [ka] [ka] [ka] [ka] [ka] (Among the above chemical formulas C-3-1 to C-3-6, Each aromatic ring's hydrogen can be substituted with a halogen, a cyano group, a C1-C30 alkyl group, a C1-C30 alkoxy group, a C1-C30 haloalkyl group, -SiH3, a C1-C30 alkylsilyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, or a C3-C30 heteroaryl group. Y 1 O, S, Se, Te, S(=O), S(=O)², NR a1 , SiR b1 R c1 , or GeR d1 R e1 (Here, R a1 , R b1 , R c1 , R d1 , and R e1 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. Y 2 O, S, Se, Te, S(=O), S(=O)², NR a2 , SiR b2 R c2, GeR d2 R e2 、 or CR f2 R g2 and (where R a2 R b2 R c2 R d2 R e2 R f2 and R g2 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH3, an alkylsilyl group having 1 to 10 carbon atoms, -NH3, an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof)), R b1 and R c1 R d1 and R e1 R b2 and R c2 R d2 and R e2 and R f2 and R g2 each independently exist or are bonded to each other to form a spiro ring, The * existing outside at least one aromatic ring is the connection point with Ar in Chemical Formula 1, and the * existing inside at least one aromatic ring is the connection point with the N(R 1 )-containing ring containing R 1 and the N(R 2 )-containing ring of Chemical Formula 1 containing R 2 ).)

[0019] In the above Chemical Formula 1, Ar 1 and Ar 2 are preferably the same or different and are selected from Chemical Formula C-4-1 and Chemical Formula C-4-2 shown below.

Chemical Formula

Chemical Formula

[0020] In the above chemical formula 1, Ar 1 and Ar 2 These are either the same or different, and are preferably selected from the chemical formulas C-5-1 to C-5-8 shown below. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] (Among the above chemical formulas C-5-1 to C-5-8, Each aromatic ring's hydrogen can be substituted with a halogen, a cyano group, a C1-C30 alkyl group, a C1-C30 alkoxy group, a C1-C30 haloalkyl group, -SiH3, a C1-C30 alkylsilyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, or a C3-C30 heteroaryl group. Y 1 O, S, Se, Te, S(=O), S(=O)², NR a1 , SiR b1 R c1 , or GeR d1 R e1 (Here, R a1 , R b1 , R c1 , R d1 , and R e1 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. Y 2 and Y 3 These are O, S, Se, Te, S(=O), S(=O)², and NR, respectively, independently. a2 , SiR b2 R c2 , GeR d2 R e2 , or CR f2 R g2 (Here, R a2 , R b2 , R c2 , R d2 , Re2 , R f2 , and R g2 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. R b1 and R c1 , R d1 and R e1 , R b2 and R c2 , R d2 and R e2 , and R f2 and R g2 These elements either exist independently or combine with each other to form a spiro ring. * located outside at least one aromatic ring is a linking site with Ar in chemical formula 1, and * located inside at least one aromatic ring is R in chemical formula 1. 1 N(R) 1 )-containing ring, and R 2 N(R) of chemical formula 1, which includes 2 )-This is the connection point with the containing ring.

[0021] The peak absorption wavelength of the near-infrared absorbing material is preferably in the wavelength range of 750 nm to 3000 nm.

[0022] To achieve the above objective, the near-infrared absorbing / blocking film according to the present invention is characterized by containing the near-infrared absorbing material of the present invention.

[0023] To achieve the above objective, the present invention provides a photoelectric element comprising a first electrode and a second electrode facing each other, and an active layer disposed between the first electrode and the second electrode, wherein the active layer contains a near-infrared absorbing material comprising a compound represented by chemical formula 1 of the present invention. Another embodiment provides a photoelectric element comprising a first electrode and a second electrode facing each other, an active layer disposed between the first electrode and the second electrode, and at least one charge auxiliary layer between the active layer and the first electrode or between the active layer and the second electrode, wherein the charge auxiliary layer includes a near-infrared absorbing material containing a compound represented by the chemical formula 1. The active layer may further include the near-infrared absorbing material.

[0024] To achieve the above objective, the organic sensor according to the present invention is characterized by including the photoelectric element of the present invention. Another embodiment provides an organic sensor comprising a semiconductor substrate, a first photoelectric element present on the semiconductor substrate that selectively absorbs light of a first near-infrared wavelength, and an additional sensor that selectively absorbs light of a separate wavelength region different from the first near-infrared wavelength. The first photoelectric element comprises a near-infrared absorbing material containing a compound represented by the chemical formula 1. The additional sensor may be an infrared sensor at least partially embedded within the semiconductor substrate, and the additional wavelength region may be a different near-infrared wavelength region from the first near-infrared wavelength region. The first photoelectric element and the infrared sensor may overlap in a direction perpendicular to the upper surface of the semiconductor substrate. The additional sensor may include a plurality of photodiodes at least partially embedded within a semiconductor substrate, the plurality of photodiodes configured to selectively absorb light in separate visible light wavelength regions, and the first photoelectric element and the plurality of photodiodes may overlap in a direction perpendicular to the upper surface of the semiconductor substrate. The organic sensor may further include an additional photoelectric element on a semiconductor substrate, the additional photoelectric element being located between the first photoelectric element and the semiconductor substrate, and the additional photoelectric element being configured to selectively absorb light in an additional wavelength region different from the first near-infrared wavelength region and the other visible light wavelength region. The above additional sensor may include at least one additional photoelectric element stacked vertically between the first photoelectric element and the semiconductor substrate, each of which an additional photoelectric element may include a separate photoelectric conversion layer and be configured to selectively absorb light in its respective wavelength region different from the first near-infrared wavelength region. The first photoelectric element includes a first electrode and a second electrode facing each other, and an active layer between the first electrode and the second electrode, the active layer may include a near-infrared absorbing material. The first photoelectric element may include a first electrode and a second electrode facing each other, an active layer between the first electrode and the second electrode, and at least one charge-supporting layer between the active layer and the first electrode, or between the active layer and the second electrode. The charge-supporting layer may include a near-infrared absorbing material.

[0025] An electronic device according to the present invention made to achieve the above objective is characterized by including a photoelectric element or an organic sensor according to the present invention. [Effects of the Invention]

[0026] The near-infrared absorbing material, near-infrared absorbing / blocking film, photoelectric element, organic sensor, and electronic device according to the present invention can provide a near-infrared absorbing material that exhibits good absorption characteristics in the near-infrared region, and such a near-infrared absorbing material can be effectively used in photoelectric elements and / or organic sensors. [Brief explanation of the drawing]

[0027] [Figure 1] This is a cross-sectional view showing the schematic configuration of a photoelectric element according to one embodiment of the present invention. [Figure 2] This is a cross-sectional view showing a schematic configuration of a photoelectric element according to another embodiment of the present invention. [Figure 3] This is a cross-sectional view showing the schematic configuration of an organic sensor according to one embodiment of the present invention. [Figure 4] This is a cross-sectional view showing a schematic configuration of an organic sensor according to another embodiment of the present invention. [Figure 5]This is a cross-sectional view showing a schematic configuration of an organic sensor according to another embodiment of the present invention. [Figure 6] This is a schematic diagram showing an example of a pixel array of an organic sensor according to one embodiment of the present invention. [Figure 7] This is a cross-sectional view showing the schematic configuration of an organic sensor according to one embodiment of the present invention. [Figure 8] This is a cross-sectional view showing a schematic configuration of an organic sensor according to another embodiment of the present invention. [Figure 9] This is a cross-sectional view showing a schematic configuration of an organic sensor according to another embodiment of the present invention. [Figure 10] This is a cross-sectional view showing a schematic configuration of an organic sensor according to another embodiment of the present invention. [Figure 11] This is a cross-sectional view showing a schematic configuration of an organic sensor according to another embodiment of the present invention. [Figure 12] This is a block diagram illustrating the schematic configuration of a digital camera including an organic sensor according to one embodiment of the present invention. [Figure 13] This is a block diagram illustrating an outline of an electronic device according to one embodiment of the present invention. [Figure 14] This graph shows the results of measuring the photoelectric conversion efficiency of photoelectric elements in Example 1 and Comparative Example 4. [Modes for carrying out the invention]

[0028] Next, specific examples of embodiments for implementing the near-infrared absorbing material, near-infrared absorbing / blocking film, photoelectric element, organic sensor, and electronic device according to the present invention will be described with reference to the drawings.

[0029] However, the structures that are actually applied can be realized in a variety of different forms and are not limited to the embodiments described herein. The thickness was enlarged in the drawing to clearly represent various layers and regions. When a part of a layer, membrane, region, or plate is said to be "on top" of another part, this includes not only when it is "directly above" the other part, but also when there is another part in between. Conversely, when one part is said to be "directly above" another part, it means that there is no other part in between. When one component is said to be "on top" of another, this can mean that it is in contact with the upper or lower part of the other component. In this specification, a component and / or its physical properties may be referred to as “identical” or “equivalent” to another component, and in this specification, a component and / or its physical properties may be referred to as “identical” to another component, meaning that they are “the same,” “equivalent,” “substantially identical,” or “substantially equivalent.” The phrase "substantially identical" or "substantially equivalent" to other components and / or their physical properties can be understood as including components and properties that are identical or equivalent to other components and / or their physical properties within the limits of manufacturing tolerances and / or material tolerances. Other components and their properties are identical or substantially identical to other components and their properties, which may mean that components and / or their properties are structurally identical or substantially identical, functionally identical or substantially identical, and / or compositionally identical or substantially identical. To clearly illustrate this embodiment in the drawings, unnecessary parts have been omitted, and the same reference numerals have been used throughout the specification for identical or similar components. In this specification, “at least one of A, B, or C,” “one of A, B, C, or any combination thereof,” and “one of A, B, C, and any combination thereof” mean all of the respective components and their combinations (e.g., A; B; C; A and B; A and C; B and C; or A, B, and C). In the following, “combination” includes two or more mixtures, intersubstitutions, and two or more layered structures.

[0030] Unless otherwise defined below, “substituted” means that the hydrogen atom in the compound or functional group is a halogen atom, a hydroxyl group (F, Br, Cl, or I), a nitro group, a cyano group, an amino group, an azide group, an amidino group, an amine group (-NR'R'', where R' and R'' are either identical or different, and are a hydrogen atom, a C1-C20 alkyl group, or a C6-C30 aryl group), a hydrazino group, a hydrazono group, a carbonyl group, a carbamoyl group, a thiol group, an ester group, a carboxyl group or its salts, a sulfonic acid group or its salts, a phosphoric acid group or its salts, or a silyl group (-SiR 1 R 2 R 3 , here, R 1 ~R 3 This means that the molecule is substituted with a substituent selected from hydrogen, a C1-C10 alkyl group, or a C6-C10 aryl group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C30 aryl group, a C7-C30 arylalkyl group, a C1-C30 alkoxy group, a C1-C20 heteroalkyl group, a C3-C20 heteroaryl group, a C3-C20 heteroarylalkyl group, a C3-C30 cycloalkyl group, a C3-C15 cycloalkenyl group, a C6-C15 cycloalkynyl group, a C3-C30 heterocycloalkyl group, and combinations thereof.

[0031] Unless otherwise defined below, “hetero” means containing one to four heteroatoms selected from N, O, S, Se, Te, Si, and P. Unless otherwise defined below, "aromatic ring" refers to a functional group in which all elements of the ring-shaped functional group have p-orbitals, and these p-orbitals form conjugation, while "heteroaromatic ring" refers to an aromatic ring containing heteroatoms. The "aromatic ring" is for example, Those with 6 to 30 carbon atoms or Those with 6 to 20 carbon atoms 'n' In other words, “heteroaromatic ring” means, for example, Heteroallenes with 3 to 30 carbon atoms or Heteroallenes with 3 to 20 carbon atoms hn It is possible.

[0032] Unless otherwise defined in this specification, “A reel The group is a hydrocarbon ring group having an aromatic ring, and includes single-ring and multi-ring hydrocarbon ring groups, where the additional rings of the multi-ring hydrocarbon ring group may be aromatic or non-aromatic rings. a reel The basis is, for example, A reel A group with 6 to 20 carbon atoms reel A group or a group with 6 to 10 carbon atoms reel It could be the basis. A ring containing 1 to 3 heteroatoms selected from N, O, S, P, and Si. reel It means "foundation." Hetero reel The basis is, for example, Heterochromia with 3 to 30 carbon atoms reel Group, heterogeneous group with 3 to 20 carbon atoms reel A group, or a heterogeneous group having 3 to 10 carbon atoms. reel It could be the basis.

[0033] Unless otherwise defined herein, “aryl group” is a general concept encompassing a group having one or more hydrocarbon aromatic molecules, including forms in which all elements of the hydrocarbon aromatic molecule have p-orbitals and these p-orbitals form conjugation, such as phenyl groups and naphthyl groups; forms in which two or more hydrocarbon aromatic molecules are linked by sigma bonds, such as biphenyl groups, terphenyl groups, and quarterphenyl groups; and non-aromatic fusion rings in which two or more hydrocarbon aromatic molecules are directly or indirectly fused, such as fluorenyl groups. The aryl group may include monocyclic, polycyclic, or fusion polycyclic (i.e., a ring sharing adjacent pairs of carbon atoms) functional groups.

[0034] Unless otherwise defined herein, “heteroaryl group” means that the ring contains at least one heteroatom selected from the group consisting of N, O, S, Se, Te, P, and Si, instead of carbon (C). When the heteroaryl group is a fusion ring, at least one of the rings forming the heteroaryl group may have a heteroatom, and each of the rings may have a heteroatom. In this specification, unless otherwise defined, “ring” means an aromatic ring, a non-aromatic ring, a heteroaromatic ring, a heteronon-aromatic ring, a fusion ring of these, and / or combination thereof. The aromatic ring is as described above, and the non-aromatic ring can be a cycloalkyl group having 3 to 30 carbon atoms, a cycloalkenyl group having 3 to 30 carbon atoms, or a cycloalkynyl group having 3 to 30 carbon atoms. Unless otherwise defined herein, “halogen” can be any one of F, Cl, Br, and I, and a haloalkyl group is one in which at least one hydrogen of an alkyl group is substituted with a halogen, and can be a perfluoroalkyl group such as -CF3.

[0035] The following describes a near-infrared absorbing material according to one embodiment of the present invention. The above-mentioned near-infrared absorbing material may be interchangeably referred to as a "near-infrared absorbing compound" in this application. A near-infrared absorbing material according to one embodiment of the present invention contains a compound represented by the chemical formula 1 shown below. [ka] In the above chemical formula 1, Ar is a substituted or unsubstituted aromatic ring with 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring with 3 to 30 carbon atoms, or a combination thereof. X 1 are O, S, Se, Te, S(=O), S(= O) 2. NR a CR b R c , SiR d R e , GeR f R gCR h =CR i , or CR hh =CR ii (Here, R a , R b , R c , R d , R e , R f , R g , R h , and R i Each of these is independently hydrogen, deuterium, a C1-C30 alkyl group, a C1-C30 haloalkyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C3-C30 heteroaryl group, a halogen, a cyano group, or a combination thereof. R hh and R ii Each is independently (CH)w (where w is a positive integer) or at least one heteroatom selected from O, N, S, Se, and T, and R hh and R ii (They are linked to each other to form an aromatic ring or heteroaromatic ring), X 2 is O, S, Se, Te, C, CR x -CR y CR xx -CR yy , S(=O), or S(= O) 2 (where R x and R y Each of these is independently hydrogen, deuterium, a C1-C30 alkyl group, a C1-C30 haloalkyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C3-C30 heteroaryl group, a halogen, a cyano group, or a combination thereof. xx and R yy Each is independently (CH)v (where v is a positive integer) or at least one heteroatom selected from O, N, S, Se, and T, and R xx and R yy (These are linked to each other to form an aromatic ring or a heteroaromatic ring), Ar 1 and Ar 2Each of these is a heteroal containing at least one heteroatom selected from O, S, Se, and Te. - n (heteroarene )in can be, Ar 3 and Ar 4 Each of these is an array of substituted or unsubstituted carbon atoms with 6 to 30 carbon atoms, independently of the others. hmm, Substituted or unsubstituted heteroelements with 3 to 30 carbon atoms Hmm, or these fused rings, R 1 and R 2 Each of these is independently hydrogen, deuterium, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C1-C10 alkoxy group, substituted or unsubstituted C6-C10 aryl group, or substituted or unsubstituted C3-C10 heteroaryl group. L 1 and L 2 These are, independently, single bonds: -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -,-(CR f R g ) n -, and -(C(R h )=C(R i ))-Selected from (where R a , R b , R c , R d , R e , R f , R g , R h and R i Each is independently selected from hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1-C10 alkyl group, and substituted or unsubstituted C6-C10 aryl group, R b and R c , R d and R e , R f and R g , or Rh and R i Each element can exist independently or be connected to each other to form a ring, -(CR f R g ) n (where n is an integer of 1 or 2).

[0036] Materials that absorb long-wavelength light, such as near-infrared light, are preferable to have a small HOMO-LUMO bandgap energy. To achieve a small bandgap energy, the conjugate length needs to be increased, but a longer conjugate length presents a problem in that it becomes difficult to apply the deposition process. The near-infrared absorbing material represented by chemical formula 1 consists of a conjugated core (Ar-containing ring in chemical formula 1) with electron-accepting properties and an aromatic fusion ring (Ar-containing ring) with electron-donating properties. 1 -(N(R 1 ) and L 1 (ring containing)-Ar 3 ) and (Ar 2 -(N(R 2 ) and L 2 (ring containing)-Ar 4 Due to its "donor-acceptor-donor" structure in which ) are bonded, it has strong charge transfer characteristics and a low bandgap energy, allowing it to effectively absorb light in the near-infrared wavelength region. Furthermore, it has excellent thermal stability and is suitable for vapor deposition processes. Therefore, layers and / or structures containing near-infrared absorbing materials can have improved sensitivity and / or absorbance to near-infrared wavelength light. A device (e.g., a sensor) configured to selectively absorb and / or convert (convert to an electrical signal, e.g., photoelectric conversion) near-infrared light can have improved performance and efficiency by, for example, including a near-infrared absorbing material in an active layer configured to selectively absorb and / or convert (convert to an electrical signal, e.g., photoelectric conversion) the near-infrared light.

[0037] Below, “N(R 1 ) and L 1The ring containing "N(R)" is "N(R) 1 )-Also called "N(R)" 2 ) and L 2 The ring containing "N(R)" is "N(R) 2 )-Also called "containing ring". “N(R 1 )-containing ring" and "N(R 2 )-Containing ring" is L 1 and L 2 Depending on the compound, it may be a five-membered ring (e.g., substituted or unsubstituted pyrrole), a six-membered ring (e.g., substituted or unsubstituted pyridine, oxazine, substituted or unsubstituted thiazine, substituted or unsubstituted selenoazine, or substituted or unsubstituted pyrazine) or a seven-membered ring (e.g., substituted or unsubstituted azepine).

[0038] In chemical formula 1, Ar may be a benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetracene ring, or a substituted or unsubstituted pyrene ring. Furthermore, in chemical formula 1, Ar may be a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted quinazoline ring, or a substituted or unsubstituted phenanthroline ring.

[0039] In chemical formula 1, Ar may be one of the moieties represented by chemical formula group A-1 shown below. [ka] Among the chemical formula group A-1 above, Each hydrogen atom in the aromatic ring can be replaced with a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, a silyl group, or a C1-C10 alkylsilyl group. The adjacent pair of * inside the aromatic ring is -NX in chemical formula 1. 1-N-containing ring and -N=X in chemical formula 1 2 =This is the part that bonds with the N-containing ring, The asterisks (*) in the left and right linking groups are Ar in chemical formula 1. 1 and Ar 2 This is the part that connects to it.

[0040] In chemical formula 1, Ar may be one of the moieties represented by chemical formula group A-2 shown below. [ka] Among the chemical formula group A-2 above, Each aromatic ring's hydrogen can be substituted with a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, a silyl group, or a C1-C10 alkylsilyl group. The adjacent pair of asterisks within the aromatic ring are -NX in chemical formula 1. 1 -N-containing ring and -N=X in chemical formula 1 2 =This is the part that bonds with the N-containing ring, The * in the left and right linking groups is Ar in chemical formula 1. 1 and Ar 2 This is the part that connects to it.

[0041] In chemical formula 1, X 2 CR xx -CR yy If R xx and R yy These can be linked together to form an aromatic ring. In this way, when aromatic rings are additionally fused, the absorption wavelength of the compound is shifted to longer wavelengths, which can increase the stability of the compound. Aromatic rings include substituted or unsubstituted benzene rings, substituted or unsubstituted naphthalene rings, substituted or unsubstituted acenaphthene rings, substituted or unsubstituted anthracene rings, substituted or unsubstituted phenanthrene rings, substituted or unsubstituted tetracene rings, or substituted or unsubstituted pyrene rings. The rings may also be substituted or unsubstituted quinoline rings, substituted or unsubstituted isoquinoline rings, substituted or unsubstituted quinoxaline rings, substituted or unsubstituted quinazoline rings, substituted or unsubstituted phenanthroline rings, substituted or unsubstituted pyrimidine rings, or substituted or unsubstituted benzodithiophene rings.

[0042] An aromatic ring can be one of the moieties represented by the chemical formula group B-1 shown below. [ka] Among the chemical formula group B-1 above, The hydrogen atoms of each aromatic ring can be halogens, cyano groups, C1-C30 alkyl groups (e.g., C1-C20 alkyl groups or C1-C10 alkyl groups), C1-C30 alkoxy groups (e.g., C1-C20 alkoxy groups or C1-C10 alkoxy groups), C1-C30 haloalkyl groups (e.g., C1-C20 haloalkyl groups or C1-C10 haloalkyl groups), -SiH3, C1-C30 alkylsilyl groups (e.g., It can be substituted with an alkylsilyl group having 1 to 20 carbon atoms or an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (for example, an aryl group having 6 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms), an aryloxy group having 6 to 30 carbon atoms (for example, an aryloxy group having 6 to 20 carbon atoms or an aryloxy group having 6 to 10 carbon atoms), or a heteroaryl group having 3 to 30 carbon atoms (for example, a heteroaryl group having 3 to 20 carbon atoms or a heteroaryl group having 3 to 10 carbon atoms). The asterisk inside the aromatic ring is CR. xx -CR yy This is the part that bonds with carbon.

[0043] An aromatic ring can be one of the moieties represented by chemical formula group B-2 shown below. [ka] Among the chemical formula group B-2 above, Each aromatic ring's hydrogen can be substituted with a halogen, a cyano group, a C1-C30 alkyl group (e.g., a C1-C20 alkyl group or a C1-C10 alkyl group), a C1-C30 alkoxy group (e.g., a C1-C20 alkoxy group or a C1-C10 alkoxy group), a C1-C30 haloalkyl group (e.g., a C1-C20 haloalkyl group or a C1-C10 haloalkyl group), -SiH3, a C1-C30 alkylsilyl group (e.g., a C1-C20 alkylsilyl group or a C1-C10 alkylsilyl group), a C6-C30 aryl group (e.g., a C6-C20 aryl group or a C6-C10 aryl group), a C6-C30 aryloxy group (e.g., a C6-C20 aryloxy group or a C6-C10 aryloxy group), or a C3-C20 heteroaryl group. The asterisk inside the aromatic ring is CR. xx -CR yy This is the part that bonds with carbon.

[0044] The aromatic ring may be one of the moieties represented by chemical formula B-3-1 or chemical formula B-3-2 shown below. [ka] [ka] In the above chemical formulas B-3-1 and B-3-2, Ar 11 and Ar 12 These are, independently, substituted or unsubstituted carbon atoms with 6 to 30 carbon atoms. and substituted or unsubstituted heteroelements with 3 to 30 carbon atoms N They were selected, In chemical formula B-3-1, Z 1 and Z 2 Each of them operates independently, CR a or N (where R aThis includes hydrogen, deuterium, C1-C30 alkyl groups (e.g., C1-C20 alkyl groups or C1-C10 alkyl groups), C1-C30 alkoxy groups (e.g., C1-C20 alkoxy groups or C1-C10 alkoxy groups), C1-C30 haloalkyl groups (e.g., C1-C20 haloalkyl groups or C1-C10 haloalkyl groups), -SiH3, C1-C30 alkylsilyl groups (e.g., C1-C20 alkylsilyl groups or C1-C10 alkylsilyl groups), -NH2, and C1-C30 alkylamine groups. (For example, alkylamine groups with 1 to 20 carbon atoms or alkylamine groups with 1 to 10 carbon atoms), arylamine groups with 6 to 30 carbon atoms (for example, arylamine groups with 6 to 20 carbon atoms or arylamine groups with 6 to 10 carbon atoms), aryl groups with 6 to 30 carbon atoms (for example, aryl groups with 6 to 20 carbon atoms or aryl groups with 6 to 10 carbon atoms), aryloxy groups with 6 to 30 carbon atoms (for example, aryloxy groups with 6 to 20 carbon atoms or aryloxy groups with 6 to 10 carbon atoms), heteroaryl groups with 3 to 30 carbon atoms, halogens, cyano groups, or combinations thereof), The asterisk inside the aromatic ring is CR. xx -CR yy This is the part that bonds with carbon.

[0045] Moieti, represented by chemical formula B-3-1, can be represented by the chemical formula group B-3-11 shown below. [ka] Among the chemical formula group B-3-11 above, The hydrogen atoms of each aromatic ring can be halogens, cyano groups, C1-C30 alkyl groups (e.g., C1-C20 alkyl groups or C1-C10 alkyl groups), C1-C30 alkoxy groups (e.g., C1-C20 alkoxy groups or C1-C10 alkoxy groups), C1-C30 haloalkyl groups (e.g., C1-C20 haloalkyl groups or C1-C10 haloalkyl groups), -SiH3, C1-C30 alkylsilyl groups (e.g., It can be substituted with an alkylsilyl group having 1 to 20 carbon atoms or an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (for example, an aryl group having 6 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms), an aryloxy group having 6 to 30 carbon atoms (for example, an aryloxy group having 6 to 20 carbon atoms or an aryloxy group having 6 to 10 carbon atoms), or a heteroaryl group having 3 to 30 carbon atoms (for example, a heteroaryl group having 3 to 20 carbon atoms or a heteroaryl group having 3 to 10 carbon atoms). The asterisk inside the aromatic ring is CR. xx -CR yy This is the part that bonds with carbon.

[0046] Moieti, represented by chemical formula B-3-2, can be represented by the chemical formula group B-3-21 shown below. [ka] Among the chemical formula group B-3-21 above, The hydrogen atoms of each aromatic ring can be halogens, cyano groups, C1-C30 alkyl groups (e.g., C1-C20 alkyl groups or C1-C10 alkyl groups), C1-C30 alkoxy groups (e.g., C1-C20 alkoxy groups or C1-C10 alkoxy groups), C1-C30 haloalkyl groups (e.g., C1-C20 haloalkyl groups or C1-C10 haloalkyl groups), -SiH3, C1-C30 alkylsilyl groups (e.g., It can be substituted with an alkylsilyl group having 1 to 20 carbon atoms or an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (for example, an aryl group having 6 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms), an aryloxy group having 6 to 30 carbon atoms (for example, an aryloxy group having 6 to 20 carbon atoms or an aryloxy group having 6 to 10 carbon atoms), or a heteroaryl group having 3 to 30 carbon atoms (for example, a heteroaryl group having 3 to 20 carbon atoms or a heteroaryl group having 3 to 10 carbon atoms). X a and X b These are O, S, Se, Te, and NR, each independent of the others. a , SiR b R c , and GeR d R e Selected from (where R a , R b , R c , R d , and R e Each of these is independently selected from hydrogen, halogen, cyano group, substituted or unsubstituted C1-C30 alkyl group (e.g., C1-C20 alkyl group or C1-C10 alkyl group), substituted or unsubstituted C1-C30 alkoxy group (e.g., C1-C20 alkoxy group or C1-C10 alkoxy group), substituted or unsubstituted C6-C30 aryl group (e.g., C6-C20 aryl group or C6-C10 aryl group), and substituted or unsubstituted C6-C30 aryloxy group (e.g., C6-C20 aryloxy group or C6-C10 aryloxy group). The asterisk inside the aromatic ring is CR. xx -CR yy This is the part that bonds with carbon.

[0047] For example, in chemical formulas B-3-11 and B-3-21, the halogen may be one of F, Cl, Br, and I, and the haloalkyl group may be one in which at least one hydrogen of the alkyl group is substituted with a halogen, for example, a perfluoroalkyl group such as -CF3. In chemical formula 1, Ar 1 and Ar 2 This is a ring group containing a heteroatom, where the heteroatom contained in the ring enhances the charge transfer characteristics and can reduce the band gap energy. Also, Ar 1 and Ar 2 The absorption wavelength can be easily adjusted by changing the number of aromatic rings. A structure in which multiple aromatic rings are fused (Ar 1 -(N(R 1 ) and L 1 (ring containing)-Ar 3 ) and (Ar 2 -(N(R 2 ) and L 2 (ring containing)-Ar 4 ) provides a donor structure, thereby increasing the length of the conjugated structure and enabling long-wavelength absorption in the near-infrared region.

[0048] In chemical formula 1, Ar 1 and Ar 2 These are either identical or different, and can be selected from the following chemical formulas C-1-1 to C-1-3. [ka] [ka] [ka] In the above chemical formulas C-1-1 to C-1-3, The hydrogen atoms of each aromatic ring can be halogens, cyano groups, C1-C30 alkyl groups (e.g., C1-C20 alkyl groups or C1-C10 alkyl groups), C1-C30 alkoxy groups (e.g., C1-C20 alkoxy groups or C1-C10 alkoxy groups), C1-C30 haloalkyl groups (e.g., C1-C20 haloalkyl groups or C1-C10 haloalkyl groups), -SiH3, C1-C30 alkylsilyl groups (e.g., It can be substituted with an alkylsilyl group having 1 to 20 carbon atoms or an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (for example, an aryl group having 6 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms), an aryloxy group having 6 to 30 carbon atoms (for example, an aryloxy group having 6 to 20 carbon atoms or an aryloxy group having 6 to 10 carbon atoms), or a heteroaryl group having 3 to 30 carbon atoms (for example, a heteroaryl group having 3 to 20 carbon atoms or a heteroaryl group having 3 to 10 carbon atoms). Y 1 O, S, Se, Te, S(=O), S(=O)², NR a1 , SiR b1 R c1 , or GeR d1 R e1 (Here, R a1 , R b1 , R c1 , R d1 , and R e1 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. Y 2 O, S, Se, Te, S(=O), S(=O)², NR a2 , SiR b2 R c2 , GeR d2 R e2 or CR f2 R g2 (Here, R a2, R b2 , R c2 , R d2 , R e2 , R f2 , and R g2 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. R b1 and R c1 , R d1 and R e1 , R b2 and R c2 , R d2 and R e2 , and R f2 and R g2 These elements may exist independently or bond to each other to form a spiro ring (e.g., a cycloalkyl group with 4-8 carbon atoms, a cycloalkyl group with 5 carbon atoms, or a cycloalkyl group with 6 carbon atoms). * located outside at least one aromatic ring is a linking site with Ar in chemical formula 1, and * located inside at least one aromatic ring is R in chemical formula 1. 1 N(R) 1 )-Containing ring and R 2 N(R) of chemical formula 1, which includes 2 )- This is the connection point with the containing ring.

[0049] In chemical formula 1, Ar 1 and Ar 2 These are either identical or different, and can be selected from the chemical formulas C-2-1 to C-2-4 shown below. [ka] [ka] [ka] [ka] In the above chemical formulas C-2-1 to C-2-4, The hydrogen atoms of each aromatic ring can be halogens, cyano groups, C1-C30 alkyl groups (e.g., C1-C20 alkyl groups or C1-C10 alkyl groups), C1-C30 alkoxy groups (e.g., C1-C20 alkoxy groups or C1-C10 alkoxy groups), C1-C30 haloalkyl groups (e.g., C1-C20 haloalkyl groups or C1-C10 haloalkyl groups), -SiH3, C1-C30 alkylsilyl groups (e.g., It can be substituted with an alkylsilyl group having 1 to 20 carbon atoms or an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (for example, an aryl group having 6 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms), an aryloxy group having 6 to 30 carbon atoms (for example, an aryloxy group having 6 to 20 carbon atoms or an aryloxy group having 6 to 10 carbon atoms), or a heteroaryl group having 3 to 30 carbon atoms (for example, a heteroaryl group having 3 to 20 carbon atoms or a heteroaryl group having 3 to 10 carbon atoms). Y 1 O, S, Se, Te, S(=O), S(=O)², NR a1 , SiR b1 R c1 , or GeR d1 R e1 (Here, R a1 , R b1 , R c1 , R d1 , and R e1 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. R b1 and R c1 , and R d1 and R e1These elements may exist independently or bond to each other to form a spiro ring (e.g., a cycloalkyl group with 4-8 carbon atoms, a cycloalkyl group with 5 carbon atoms, or a cycloalkyl group with 6 carbon atoms). * located outside at least one aromatic ring is a linking site with Ar in chemical formula 1, and * located inside at least one aromatic ring is R in chemical formula 1. 1 N(R) 1 )-Containing ring and R 2 N(R) of chemical formula 1, which includes 2 )- This is the connection point with the containing ring.

[0050] In chemical formula 1, Ar 1 and Ar 2 They are either identical or different, and can be selected from the chemical formulas C-3-1 to C-3-6 shown below. [ka] [ka] [ka] [ka] [ka] [ka] Among the above chemical formulas C-3-1 to C-3-6, The hydrogen atoms of each aromatic ring can be halogens, cyano groups, C1-C30 alkyl groups (e.g., C1-C20 alkyl groups or C1-C10 alkyl groups), C1-C30 alkoxy groups (e.g., C1-C20 alkoxy groups or C1-C10 alkoxy groups), C1-C30 haloalkyl groups (e.g., C1-C20 haloalkyl groups or C1-C10 haloalkyl groups), -SiH3, C1-C30 alkylsilyl groups (e.g., It can be substituted with an alkylsilyl group having 1 to 20 carbon atoms or an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (for example, an aryl group having 6 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms), an aryloxy group having 6 to 30 carbon atoms (for example, an aryloxy group having 6 to 20 carbon atoms or an aryloxy group having 6 to 10 carbon atoms), or a heteroaryl group having 3 to 30 carbon atoms (for example, a heteroaryl group having 3 to 20 carbon atoms or a heteroaryl group having 3 to 10 carbon atoms). Y 1 O, S, Se, Te, S(=O), S(=O)², NR a1 , SiR b1 R c1 , or GeR d1 R e1 (Here, R a1 , R b1 , R c1 , R d1 , and R e1 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. Y 2 O, S, Se, Te, S(=O), S(=O)², NR a2 , SiR b2 R c2 , GeR d2 R e2 , or CR f2 R g2 (Here, R a2, R b2 , R c2 , R d2 , R e2 , R f2 , and R g2 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. R b1 and R c1 , R d1 and R e1 , R b2 and R c2 , R d2 and R e2 , and R f2 and R g2 These elements either exist independently or are bonded to each other to form a spiro ring (for example, a cycloalkyl group with 4-8 carbon atoms, a cycloalkyl group with 5 carbon atoms, or a cycloalkyl group with 6 carbon atoms). * located outside at least one aromatic ring is a linking site with Ar in chemical formula 1, and * located inside at least one aromatic ring is R in chemical formula 1. 1 N(R) 1 )-Containing ring and R 2 N(R) of chemical formula 1, which includes 2 )- This is the connection point with the containing ring.

[0051] In chemical formula 1, Ar 1 and Ar 2 They are either identical or different, and can be selected from the chemical formulas C-4-1 and C-4-2 shown below. [ka] [ka] In the above chemical formulas C-4-1 and C-4-2, Each aromatic ring's hydrogen can be substituted with a halogen, a cyano group, a C1-C30 alkyl group, a C1-C30 alkoxy group, a C1-C30 haloalkyl group, -SiH3, a C1-C30 alkylsilyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, or a C3-C30 heteroaryl group. Y 1 O, S, Se, Te, S(=O), S(=O)², NR a1 , SiR b1 R c1 , or GeR d1 R e1 (Here, R a1 , R b1 , R c1 , R d1 , and R e1 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. Y 2 O, S, Se, Te, S(=O), S(=O)², NR a2 , SiR b2 R c2 , GeR d2 R e2 , or CR f2 R g2 (Here, R a2 , R b2 , R c2 , R d2 , R e2 , R f2 , and R g2Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. R b1 and R c1 , R d1 and R e1 , R b2 and R c2 , R d2 and R e2 , and R f2 and R g2 These elements either exist independently or are bonded to each other to form a spiro ring. * located outside at least one aromatic ring is a linking site with Ar in chemical formula 1, and * located inside at least one aromatic ring is R in chemical formula 1. 1 N(R) 1 )-Containing ring and R 2 N(R) of chemical formula 1, which includes 2 )- This is the connection point with the containing ring.

[0052] In chemical formula 1, Ar 1 and Ar 2 These are either identical or different, and can be selected from the chemical formulas C-5-1 to C-5-8 shown below. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] Among the above chemical formulas C-5-1 to C-5-8, The hydrogen atoms of each aromatic ring can be halogens, cyano groups, C1-C30 alkyl groups (e.g., C1-C20 alkyl groups or C1-C10 alkyl groups), C1-C30 alkoxy groups (e.g., C1-C20 alkoxy groups or C1-C10 alkoxy groups), C1-C30 haloalkyl groups (e.g., C1-C20 haloalkyl groups or C1-C10 haloalkyl groups), -SiH3, C1-C30 alkylsilyl groups (e.g., It can be substituted with an alkylsilyl group having 1 to 20 carbon atoms or an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (for example, an aryl group having 6 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms), an aryloxy group having 6 to 30 carbon atoms (for example, an aryloxy group having 6 to 20 carbon atoms or an aryloxy group having 6 to 10 carbon atoms), or a heteroaryl group having 3 to 30 carbon atoms (for example, a heteroaryl group having 3 to 20 carbon atoms or a heteroaryl group having 3 to 10 carbon atoms). Y 1 O, S, Se, Te, S(=O), S(=O)², NR a1 , SiR b1 R c1 , or GeR d1 R e1 (Here, R a1 , R b1 , R c1 , R d1 , and R e1 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. Y2 and Y 3 These are O, S, Se, Te, S(=O), S(=O)², and NR, respectively, independently. a2 , SiR b2 R c2 , GeR d2 R e2 , or CR f2 R g2 (Here, R a2 , R b2 , R c2 , R d2 , R e2 , R f2 , and R g2 Each of these is independently hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, -SiH3, a C1-C10 alkylsilyl group, -NH3, a C1-C10 alkylamine group, a C6-C10 arylamine group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof. R b1 and R c1 , R d1 and R e1 , R b2 and R c2 , R d2 and R e2 , and R f2 and R g2 These elements may exist independently or bond to each other to form a spiro ring (e.g., a cycloalkyl group with 4-8 carbon atoms, a cycloalkyl group with 5 carbon atoms, or a cycloalkyl group with 6 carbon atoms). * located outside at least one aromatic ring is a linking site with Ar in chemical formula 1, and * located inside at least one aromatic ring is R in chemical formula 1. 1 N(R) 1 )-Containing ring and R 2 N(R) of chemical formula 1, which includes 2 )- This is the connection point with the containing ring.

[0053] Near-infrared absorbers can absorb light in the near-infrared wavelength range, and their peak absorption wavelength (λ) is the peak absorption wavelength of the near-infrared absorber. max ) may be, for example, approximately 750 nm or more, for example, approximately 770 nm or more, for example, approximately 780 nm or more, for example, approximately 790 nm or more, for example, approximately 800 nm or more, for example, approximately 810 nm or more, for example, approximately 820 nm or more, or approximately 830 nm or more. The peak absorption wavelength of the near-infrared absorbing material may, for example, belong to the wavelength region of approximately 750 nm to 3000 nm, and within that range, it may belong to the wavelength region of approximately 750 nm to 2500 nm, approximately 780 nm to 2200 nm, approximately 790 nm to 2100 nm, approximately 800 nm to 2000 nm, approximately 810 nm to 2000 nm, approximately 820 nm to 2000 nm, or approximately 830 nm to 2000 nm.

[0054] Near-infrared absorbing materials can exhibit good charge transfer characteristics, which in turn allows them to absorb light (e.g., selectively) and convert it into electrical signals (e.g., photoelectric conversion). Therefore, they can be effectively used as photoelectric conversion materials in photoelectric devices. Therefore, for example, a photoelectric element that includes a near-infrared absorbing material in its active layer and / or charge auxiliary layer (for example, the active layer 30 and / or charge auxiliary layers 40, 45 shown in Figures 1 and 2) can have improved performance and / or efficiency, for example, by including a near-infrared absorbing material, it can have improved performance and / or efficiency in relation to realizing the photoelectric conversion of incident near-infrared light. Near-infrared absorbing materials have good heat resistance and can prevent or reduce thermal decomposition during deposition, allowing for repeated deposition. Near-infrared absorbing materials can be deposited by thermal deposition or vacuum deposition, for example, by sublimation. For example, sublimation deposition can be confirmed by thermogravimetric analysis (TGA). When performing thermogravimetric analysis at a pressure of approximately 10 Pa or less, the temperature at which a 10% weight reduction relative to the initial weight occurs may be approximately 400°C or lower, for example, approximately 390°C or lower, approximately 380°C or lower, or approximately 370°C or lower. For example, when thermogravimetric analysis is performed on a near-infrared absorbing material at a pressure of approximately 10 Pa or less, the temperature at which a 10% weight loss occurs relative to the initial weight may be approximately 230°C to 400°C.

[0055] Another embodiment of the present invention provides a near-infrared absorbing / blocking film containing a near-infrared absorbing material. The near-infrared absorbing / blocking film of the present invention can be applied to a variety of fields where absorption characteristics in the near-infrared wavelength range are required. Since near-infrared absorbing materials simultaneously possess both absorption and photoelectric properties in the near-infrared wavelength range, they can be effectively used as photoelectric conversion materials.

[0056] Figure 1 is a cross-sectional view showing a schematic configuration of a photoelectric element according to one embodiment of the present invention. Referring to Figure 1, a photoelectric element 100 according to one embodiment of the present invention includes a first electrode 10 and a second electrode 20 facing each other, and an active layer 30 disposed between the first electrode 10 and the second electrode 20.

[0057] The substrate (not shown) is positioned on the side of the first electrode 10 and on the side of the second electrode 20. The substrate can be manufactured from, for example, an inorganic material such as glass, an organic material such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, polyethersulfone, or a combination thereof, or a silicon wafer. The circuit board may be omitted. One of the first electrode 10 and the second electrode 20 is the anode, and the other is the cathode. For example, the first electrode 10 is the anode, and the second electrode 20 is the cathode.

[0058] At least one of the first electrode 10 and the second electrode 20 may be a light-transmitting electrode, which can be manufactured from a conductive oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO), aluminum tin oxide (AlTO), and fluorine-doped tin oxide (FTO), or from a thin single or multiple layer metal film. If one of the first electrode 10 and the second electrode 20 is an opaque electrode, it can be manufactured from an opaque conductor such as aluminum (Al), silver (Ag), or gold (Au). For example, both the first electrode 10 and the second electrode 20 can be transparent electrodes. For example, the second electrode 20 may be a light-receiving electrode located on the light-receiving side.

[0059] The active layer 30 is a layer in which a p-type semiconductor and an n-type semiconductor form a pn junction. It receives light from the outside (for example, outside the active layer 30) to generate an exciton, and then separates the generated exciton into holes and electrons. p-type semiconductors and n-type semiconductors are light-absorbing materials that absorb (e.g., selectively absorb) light in at least a certain wavelength range, and near-infrared absorbing materials are used as either p-type or n-type semiconductors. For example, near-infrared absorbing materials are used as p-type semiconductors and include fullerene or fullerene derivatives as n-type semiconductors. Therefore, the active layer 30 may at least partially include the aforementioned near-infrared absorbing material (for example, a near-infrared absorbing material and a fullerene or fullerene derivative). Furthermore, the peak absorption wavelength (λ) of the active layer 30 is also present. max) may be, for example, about 750 nm or more, for example, about 770 nm or more, for example, about 780 nm or more, for example, about 790 nm or more, for example, about 800 nm or more, for example, about 810 nm or more, for example, about 820 nm or more, or about 830 nm or more. The peak absorption wavelength of the near-infrared absorbing material is, for example, in the wavelength range of approximately 750 nm to 3000 nm, and within that range, it may belong to the wavelength range of approximately 750 nm to 2500 nm, approximately 780 nm to 2200 nm, approximately 790 nm to 2100 nm, approximately 800 nm to 2000 nm, approximately 810 nm to 2000 nm, approximately 820 nm to 2000 nm, or approximately 830 nm to 2000 nm. The active layer 30 and the photoelectric element 100 containing it can have improved near-infrared absorption characteristics (e.g., improved sensitivity to light in the near-infrared wavelength region, improved absorptiveness to light in the near-infrared region, etc.), thereby enabling improved photoelectric conversion performance and / or efficiency and / or improved thermal stability based on the active layer containing the aforementioned near-infrared absorbing material. In one embodiment, the active layer 30 may be a near-infrared absorbing / blocking film containing a near-infrared absorbing material.

[0060] The active layer 30 may include an intrinsic layer in which the aforementioned near-infrared absorbing material (e.g., p-type semiconductor) and fullerene or a fullerene derivative (e.g., n-type semiconductor) are co-deposited. In this case, the p-type semiconductor and the n-type semiconductor may be included in a volume ratio of about 1:9 to 9:1, or within that range, for example, in a volume ratio of about 2:8 to 8:2, or within that range, for example, in a volume ratio of about 3:7 to 7:3, or within that range, for example, in a volume ratio of about 4:6 to 6:4, or within that range, for example, in a volume ratio of about 5:5.

[0061] The active layer 30 may further include a p-type layer and / or an n-type layer in addition to the intrinsic layer. The p-type layer may contain the aforementioned near-infrared absorbing material (e.g., a p-type semiconductor), and the n-type layer may contain the aforementioned n-type semiconductor. For example, it can be included in various combinations such as p-type layer / I-type layer, I-type layer / n-type layer, p-type layer / I-type layer / n-type layer, etc. The photoelectric element 100 may further include auxiliary layers (not shown) disposed between the first electrode 10 and the active layer 30 and / or between the second electrode 20 and the active layer 30. The auxiliary layer may be a charge auxiliary layer or an optical auxiliary layer. Such a photoelectric element is shown in Figure 2.

[0062] Figure 2 is a cross-sectional view showing a schematic configuration of a photoelectric element according to another embodiment of the present invention. Referring to Figure 2, the photoelectric element 200 includes a first electrode 10 and a second electrode 20 facing each other, an active layer 30 disposed between the first electrode 10 and the second electrode 20, a first auxiliary layer 40 disposed between the first electrode 10 and the active layer 30, and a second auxiliary layer 45 disposed between the second electrode 20 and the active layer 30. In one embodiment, only one of the first auxiliary layer 40 and the second auxiliary layer 45 may be included in the photoelectric element 200.

[0063] The first auxiliary layer 40 and the second auxiliary layer 45 are charge auxiliary layers that facilitate the movement of holes and electrons separated in the active layer 30, thereby increasing efficiency. The charge auxiliary layers 40 and / or 45 may include at least one selected from a hole injecting layer (HIL) for facilitating hole injection, a hole transporting layer (HTL) for facilitating hole transport, an electron blocking layer (EBL) for preventing electron movement, an electron injecting layer (EIL) for facilitating electron injection, an electron transporting layer (ETL) for facilitating electron transport, and a hole blocking layer (HBL) for preventing hole movement.

[0064] The charge auxiliary layers 40 and / or 45 may include, for example, organic materials, inorganic materials, or organic-inorganic materials. Organic substances can be organic compounds that have holes or electronic properties, while inorganic substances can be metal oxides such as molybdenum oxide, tungsten oxide, or nickel oxide. The charge auxiliary layer may include, for example, the aforementioned near-infrared absorbing material. In one embodiment, the charge auxiliary layer 40 and / or 45 may include the aforementioned near-infrared absorbing material, and the active layer 30 may also include the aforementioned near-infrared absorbing material. In one embodiment, the charge auxiliary layer 40 and / or 45 may include the aforementioned near-infrared absorbing material, and the active layer 30 may not include the aforementioned near-infrared absorbing material. The charge auxiliary layer 40 and / or 45 and the photoelectric element 200 including it can exhibit improved near-infrared light absorption characteristics (e.g., improved sensitivity to light in the near-infrared wavelength region, improved absorptiveness to light in the near-infrared region, etc.) and thereby improved photoelectric conversion performance and / or efficiency and / or improved thermal stability based on the charge auxiliary layer 40 and / or 45 including the aforementioned near-infrared absorbing material. The optical auxiliary layer is positioned in the direction of light incidence of the photoelectric element, and is positioned above the active layer 30 when, for example, the second electrode 20 is a photoreceiving electrode (for example, an electrode close to the position where light enters the photoelectric element 200). For example, the optical auxiliary layer is placed between the second electrode 20 and the active layer 30.

[0065] The photoelectric elements (100, 200) may further include an anti-reflective layer 47 on one surface of the first electrode 10 or the second electrode 20. The anti-reflective layer 47 can be positioned on the side where light is incident to further improve light absorption by reducing the reflectivity of the incident light. For example, when light is incident on the first electrode 10 side, the anti-reflective layer is placed on one surface of the first electrode 10, and when light is incident on the second electrode 20 side, the anti-reflective layer is placed on one surface of the second electrode 20. The anti-reflective layer 47 may, for example, contain a substance having a refractive index of about 1.6 to 2.5, and may contain, for example, at least one of metal oxides, metal sulfides, and organic substances having a refractive index within the said range.

[0066] The anti-reflective layer 47 may include, but is not limited to, metal oxides such as aluminum-containing oxides, molybdenum-containing oxides, tungsten-containing oxides, vanadium-containing oxides, rhenium-containing oxides, niobium-containing oxides, tantalum-containing oxides, titanium-containing oxides, nickel-containing oxides, copper-containing oxides, cobalt-containing oxides, manganese-containing oxides, chromium-containing oxides, tellurium-containing oxides, or combinations thereof, metal sulfides such as zinc sulfide, or organic substances such as amine derivatives.

[0067] In the photoelectric elements (100, 200), if light is incident from the first electrode 10 or the second electrode 20 side and the active layer 30 absorbs light in a specific (or predetermined) wavelength range, an exciton is generated inside. The exciton is separated into a hole and an electron in the active layer 30. The separated hole moves to the anode side, which is one of the first electrode 10 and the second electrode 20, and the separated electron moves to the cathode side, which is the other of the first electrode 10 and the second electrode 20, causing an electric current to flow.

[0068] Photoelectric elements (100, 200) can be applied to, but are not limited to, solar cells, image sensors, photodetectors, light sensors, and organic light-emitting diodes. Photoelectric elements (100, 200) can be applied to, for example, organic sensors. The organic sensor may be an organic CMOS sensor, for example, an organic CMOS infrared light sensor or an organic CMOS image sensor. In one embodiment, the photoelectric element 100 may include a near-infrared absorbing material in any component, including one or more of the first electrode 10 or the second electrode 20, in addition to or as an alternative to the active layer 30. In one embodiment, the photoelectric element 200 may include a near-infrared absorbing material in any component including one or more first electrodes 10 or second electrodes 20, in addition to or as an alternative to the active layer 30 and / or one or more charge auxiliary layers 40 / 45.

[0069] Figure 3 is a cross-sectional view showing an organic sensor according to one embodiment of the present invention. An organic sensor 300 according to one embodiment of the present invention includes a semiconductor substrate 110, an insulating layer 80, and a photoelectric element 100. The semiconductor substrate 110 may be a silicon substrate and has a transmission transistor (not shown) and a charge storage 55 integrated on it.

[0070] The charge storage 55 is integrated for each pixel. The charge storage 55 is electrically connected to the photoelectric element 100, and information from the charge storage 55 is transmitted by the transmission transistor. Metal wiring (not shown) and pads (not shown) are also formed on the semiconductor substrate 110. Metal wiring and pads can be manufactured from, but are not limited to, metals with low resistivity to reduce signal delay, such as aluminum (Al), copper (Cu), silver (Ag), and alloys thereof. However, the structure is not limited to the above, and metal wiring and pads may be arranged on the lower part of the semiconductor substrate 110.

[0071] An insulating layer 80 is formed on top of the metal wiring and pads. The insulating layer 80 can be formed from an inorganic insulating material such as silicon oxide and / or silicon nitride, or from a low dielectric constant (low K) material such as SiC, SiCOH, SiCO, and / or SiOF. The insulating layer 80 has a trench 85 that exposes the charge storage 55. The trench is filled with filler material. The aforementioned photoelectric element 100 is formed on the insulating layer 80. The photoelectric element 100 includes a first electrode 10, an active layer 30, and a second electrode 20, as described above. The figure illustrates a structure in which the first electrode 10, the active layer 30, and the second electrode 20 are sequentially stacked, but the structure is not limited to this, and the second electrode 20, the active layer 30, and the first electrode 10 may be arranged in that order.

[0072] The first electrode 10 and the second electrode 20 may both be transparent electrodes, and the active layer 30 is as described with reference to Figures 1 and 2. The active layer 30 selectively absorbs light in the near-infrared wavelength range. Light incident from the second electrode 20 side is mainly absorbed in the active layer 30 in the near-infrared wavelength range and converted into photoelectric energy. As described above with reference to Figure 1, the active layer 30 can include the aforementioned near-infrared absorbing material, thereby improving sensitivity to near-infrared light and enhancing the performance and / or efficiency (e.g., photoelectric conversion performance and / or efficiency) of the organic sensor 300 in absorbing and / or converting (converting light into electrical signals) incident near-infrared light. A focusing lens (not shown) may be further formed on the photoelectric element 100. A focusing lens controls the direction of incident light to concentrate it at a single point. The focusing lens may, for example, be cylindrical or hemispherical in shape, but is not limited to these. Figure 3 shows an organic sensor to which the photoelectric element 100 from Figure 1 is applied, but the photoelectric element 200 from Figure 2 can also be applied in a similar manner (for example, by replacing the photoelectric element 100 with the organic sensor 300).

[0073] The organic sensor according to this embodiment may be an organic infrared light sensor, for example, an iris sensor or a depth sensor. An iris sensor is a sensor that identifies an individual using the unique iris characteristics of each person. It can perform iris recognition by capturing a picture of the user's eye at an appropriate distance from the user, processing the captured image, and comparing it with a pre-stored image. A depth sensor is a sensor that determines the shape and position of a three-dimensional object from its information. It captures an image of the object within an appropriate distance from the user, and then processes the captured image to confirm the object's shape and position. Such a depth sensor can be used, for example, as a face recognition sensor.

[0074] Figure 4 is a cross-sectional view showing a schematic configuration of an organic sensor according to another embodiment of the present invention. The organic sensor according to this embodiment may include multiple sensors with different functions. For example, at least one of the multiple sensors with different functions may be a biorecognition sensor, which may be, but is not limited to, an iris sensor, distance sensor, fingerprint sensor, or vascular distribution sensor. For example, one of several sensors with different functions may be an iris sensor, while another may be a distance sensor.

[0075] As an example, the multiple sensors include, for example, a first infrared light sensor that senses light in the infrared region having a first wavelength λ1 within the infrared wavelength region (e.g., selectively absorbs and / or converts it (converts it to an electrical signal, e.g., photoelectric conversion)) and a second infrared light sensor that senses infrared light having a second wavelength λ2 (the same as or different from the infrared wavelength region including the first wavelength λ1) within the infrared wavelength region (e.g., selectively absorbs and / or converts it (converts it to an electrical signal, e.g., photoelectric conversion)). The first wavelength λ1 and the second wavelength λ2 may differ from each other, for example, within the wavelength range of approximately 750 nm to 3000 nm. For example, the difference between the first wavelength λ1 and the second wavelength λ2 may be approximately 30 nm or more, approximately 50 nm or more within the aforementioned range, approximately 70 nm or more, approximately 80 nm or more, and approximately 90 nm or more.

[0076] For example, one of the first wavelength λ1 and the second wavelength λ2 may belong to the wavelength region of approximately 780 nm to 900 nm, and the other of the first wavelength λ1 and the second wavelength λ2 may belong to the wavelength region of approximately 900 nm to 1000 nm. For example, one of the first wavelength λ1 and the second wavelength λ2 may belong to the wavelength region of approximately 780 nm to 840 nm, and the other of the first wavelength λ1 and the second wavelength λ2 may belong to the wavelength region of approximately 910 nm to 970 nm. For example, one of the first wavelength λ1 and the second wavelength λ2 may belong to the wavelength region of approximately 800 nm to 830 nm, and the other of the first wavelength λ1 and the second wavelength λ2 may belong to the wavelength region of approximately 930 nm to 950 nm.

[0077] For example, one of the first wavelength λ1 and the second wavelength λ2 may belong to the wavelength region of approximately 805 nm to 815 nm, and the other of the first wavelength λ1 and the second wavelength λ2 may belong to the wavelength region of approximately 935 nm to 945 nm. For example, one of the first wavelength λ1 and the second wavelength λ2 could be approximately 810 nm, and the other of the first wavelength λ1 and the second wavelength λ2 could be approximately 940 nm.

[0078] The organic sensor 400 according to this embodiment includes a semiconductor substrate 110 on which a dual bandpass filter 95, a first infrared light sensor 100A, an insulating layer 80, and a second infrared light sensor 120 are integrated. The second infrared light sensor 120 is at least partially embedded within the semiconductor substrate 110. The first infrared light sensor 100A and the second infrared light sensor 120 are stacked, for example, in a direction perpendicular to the upper surface 110S of the semiconductor substrate 110. As shown in Figure 4, the dual bandpass filter 95 is positioned on the front side of the organic sensor 400 and selectively transmits infrared light including a first wavelength λ1 (e.g., light in the infrared wavelength range) and infrared light including a second wavelength λ2, while blocking and / or absorbing other light. Here, "other light" includes light in the ultraviolet and visible light regions.

[0079] The first infrared light sensor 100A includes a first electrode 10, an active layer 30, and a second electrode 20. As shown in Figure 4, the first infrared light sensor 100A is the same as the photoelectric element 100 in the embodiment described above with reference to Figure 1. In one embodiment, the first infrared light sensor 100A may be the photoelectric element 200 shown in Figure 2. As shown in Figure 4, the second infrared light sensor 120 may be integrated within the semiconductor substrate 110 and may be a light sensing element. The semiconductor substrate 110 may be, for example, a silicon substrate, and integrates a second infrared light sensor 120, a charge storage unit 55, and a transmission transistor (not shown). The second infrared light sensor 120 may be a photodiode (for example, a silicon-based photodiode), which senses (for example, absorbs) incoming light, and the sensed information can be transmitted by a transmission transistor.

[0080] Here, the light flowing into the second infrared light sensor 120 is light that has passed through the dual bandpass filter 95 and the first infrared light sensor 100A (for example, selectively transmitted), and may be infrared light in a specific (or predetermined) region including the second wavelength λ2. Infrared light in a predetermined region including the first wavelength λ1 may be completely absorbed by the active layer 30 of the first infrared light sensor and may not reach the second infrared light sensor 120. In this case, a separate filter is not required for wavelength selectivity of the light flowing into the second infrared light sensor 120. However, a filter may be additionally provided between the first infrared light sensor 100A and the second infrared light sensor 120 in case infrared light in a specific (or predetermined) region including the first wavelength λ1 is not completely absorbed by the active layer 30. Therefore, in the organic sensor 400, the first infrared sensor 100A may include photoelectric elements (e.g., photoelectric elements 100 and / or 200) configured to sense (e.g., selectively absorb and / or convert into an electrical signal (e.g., photoelectric conversion)) light in a first near-infrared wavelength region of incident light (e.g., a first near-infrared wavelength region including a first wavelength λ1), and the second infrared sensor 120 may be an additional sensor configured to selectively absorb and / or convert (e.g., photoelectric conversion) light in a different wavelength region of incident light (e.g., a second near-infrared wavelength region that differs from the first near-infrared wavelength region, including a second wavelength λ2 and excluding the first wavelength λ1).

[0081] The organic sensor according to this embodiment can not only function as a composite sensor by including two infrared light sensors that perform separate functions, but also significantly improve sensitivity by stacking two sensors that perform separate functions in each pixel, while maintaining the same size, thereby doubling the number of pixels that can perform the function of each sensor. As described above with reference to Figure 1, any portion of the active layer 30 or the photoelectric elements 100 and / or 200 can include the aforementioned near-infrared absorbing material, thereby improving the sensitivity and / or absorbance to near-infrared light and enhancing performance, and improving the performance and efficiency (e.g., photoelectric conversion performance and / or efficiency) of the organic sensor 400 that absorbs and / or photoelectrically converts incident near-infrared light as an electrical signal. In one embodiment, the second infrared sensor 120 may include the aforementioned near-infrared absorbing material, thereby improving its sensitivity and / or absorbance to near-infrared light and enhancing its performance, and improving the performance and efficiency (e.g., photoelectric conversion performance and / or efficiency) of the organic sensor 400 that absorbs and / or photoelectrically converts incident near-infrared light as an electrical signal.

[0082] Figure 5 is a cross-sectional view showing a schematic configuration of an organic sensor according to another embodiment. The organic sensor according to this embodiment may be an organic CMOS image sensor. Referring to Figure 5, an organic sensor 500 according to one embodiment of the present invention includes a semiconductor substrate 110 on which a light sensing element (e.g., photodiode, e.g., silicon-based photodiode) (50a, 50b, 50c), a transmission transistor (not shown), and a charge storage 55 are integrated, a lower insulating layer 60, color filters (70a, 70b, 70c), an upper insulating layer 80, and a photoelectric element 100.

[0083] The semiconductor substrate 110 integrates photosensing elements (50a, 50b, 50c), a transmission transistor (not shown), and a charge storage unit 55. The photosensing elements (50a, 50b, 50c) are at least partially embedded in the semiconductor substrate 110 and are superimposed on the photoelectric element 100 in a direction perpendicular to the upper surface 110S of the semiconductor substrate 110. The light sensing elements (50a, 50b, 50c) may be photodiodes (e.g., silicon photodiodes) configured to sense (e.g., selectively absorb and / or convert (photoconversion)) light of different visible wavelengths.

[0084] The light-sensing elements (50a, 50b, 50c), transmission transistors, and / or charge storage units 55 are integrated for each pixel, and as an example, the light-sensing element 50a is included in the red pixel, the light-sensing element 50b is included in the green pixel, and the light-sensing element 50c is included in the blue pixel. The light sensing elements (50a, 50b, 50c) sense light (for example, selectively absorb and / or convert it (convert it into an electrical signal, for example, photoelectric conversion)), the sensed information is transmitted by a transmission transistor, the charge storage 55 is electrically connected to the photoelectric element 100, and the information from the charge storage 55 is transmitted by a transmission transistor.

[0085] Metal wiring (not shown) and pads (not shown) are also formed on the semiconductor substrate 110. Metal wiring and pads can be manufactured from metals with low resistivity to reduce signal delay, such as aluminum (Al), copper (Cu), silver (Ag), and alloys thereof, but are not limited to these. However, the structure is not limited to the above, and the metal wiring and pads are arranged below the light sensing elements (50a, 50b). A lower insulating layer 60 is formed on top of the metal wiring and pads. The lower insulating layer 60 may contain the same or a different material composition as the insulating layer 80.

[0086] Color filters (70a, 70b, 70c) are formed on top of the lower insulating layer 60. The color filters (70a, 70b, 70c) include a blue filter 70a formed on blue pixels, a red filter 70b formed on red pixels, and a green filter 70c formed on green pixels. An insulating layer 80 (also called the upper insulating layer) is formed on top of the color filters (70a, 70b, 70c). The insulating layer 80 is flattened by removing any steps caused by the color filters (70a, 70b, 70c).

[0087] The aforementioned photoelectric element 100 is formed on the insulating layer 80. As described above, the photoelectric element 100 includes a first electrode 10, an active layer 30, and a second electrode 20. The figure illustrates a structure in which the first electrode 10, the active layer 30, and the second electrode 20 are sequentially stacked, but the structure is not limited to this, and the second electrode 20, the active layer 30, and the first electrode 10 may be arranged in that order. The first electrode 10 and the second electrode 20 may both be transparent electrodes, and the active layer 30 is as described above. The active layer 30 selectively absorbs and / or converts (converts to electrical signals, e.g., photoelectric conversion) light in the near-infrared wavelength range. As previously mentioned in relation to the photoelectric elements (100, 200), any part of the photoelectric element 100 (for example, the first electrode 10, the second electrode 20, and / or the active layer 30) may include the aforementioned near-infrared absorbing material.

[0088] Light incident from the second electrode 20 side is mainly absorbed in the near-infrared wavelength region by the active layer 30 and converted into photoelectric energy. Light in the remaining wavelength range passes through the first electrode 10 and the color filters (70a, 70b, 70c). Light in the red wavelength range that passes through color filter 70a is sensed by the photosensing element 50a, light in the green wavelength range that passes through color filter 70b is sensed by the photosensing element 50b, and light in the blue wavelength range that passes through color filter 70c is sensed by the photosensing element 50c. As described above with reference to Figure 1, the active layer 30, by including the aforementioned near-infrared absorbing material, has improved sensitivity to near-infrared light, thereby improving the performance and / or efficiency (e.g., photoelectric conversion performance and / or efficiency) of the organic sensor 500 that absorbs and / or converts (converts light into electrical signals) incident near-infrared light. Therefore, if an organic sensor includes a photoelectric element configured to selectively absorb and / or convert (e.g., photoelectric conversion) light in a first near-infrared wavelength region, the organic sensor may include an additional sensor configured to selectively absorb and / or convert (convert to an electrical signal, e.g., photoelectric conversion) light in a separate visible wavelength region (e.g., red, blue, and / or green light) by including a plurality of photodiodes (e.g., photosensing elements 50a, 50b, 50c) at least partially embedded in a semiconductor substrate. Figure 6 is a schematic diagram showing an example of a pixel array of an organic sensor according to one embodiment. Referring to Figure 6, an organic sensor 600 according to one embodiment may include a plurality of pixels PX, the plurality of pixels PX having a matrix array arranged iteratively along rows and columns. Multiple pixels PX can form (at least partially include) a unit pixel group A of, for example, a 2x2 pixel array, as shown in Figure 6. However, the pixel arrangement is not limited to this and can be modified in various ways; a unit pixel group A can be transformed into various pixel arrays other than a 2x2 array, such as a 3x3 array or a 4x4 array. At least some of the pixels can contain multiple sensors with different functions within a single pixel, and these multiple sensors can be stacked inside it. In some exemplary embodiments, each pixel PX may include two or more organic sensors configured to sense (e.g., absorb) light in different wavelength regions ("wavelength spectrum of light") relative to each other. Organic sensors configured to sense light in different wavelength regions can be stacked in a direction perpendicular to the upper surface 110S of the substrate of the organic sensor 600 (e.g., perpendicular within the manufacturing tolerance and / or material tolerance range), as shown in Figure 7 (e.g., y direction). Here, light from different wavelength regions can be selected from the visible light wavelength region, the infrared wavelength region including the near-infrared wavelength region, and the ultraviolet (UV) wavelength region, respectively. Any organic sensor according to any exemplary embodiment of this specification may have a pixel array structure of organic sensor 600 as shown in Figure 6. Figure 7 is a cross-sectional view showing an organic sensor according to one embodiment. As shown in Figure 7, an organic sensor 700 according to one embodiment includes a semiconductor substrate 110 on which a visible light sensor 50, which includes light sensing elements (50a, 50b), a transmission transistor (not shown), and a charge storage 55, is integrated, a lower insulating layer 60, a color filter layer 70, an insulating layer 80 (also called an upper insulating layer when present together with the lower insulating layer 60 in the same organic sensor), and a photoelectric element 100. The semiconductor substrate 110 may be a silicon substrate and integrates a photosensing element (50a, 50b), a transmission transistor (not shown), and a charge storage unit 55. The light sensing elements (50a, 50b) may be photodiodes (for example, silicon-based photodiodes). The light sensing elements (50a, 50b) sense light, and the information sensed by the light sensing elements is transmitted by the transmission transistor. The charge storage 55 is electrically connected to the photoelectric element 100, and the information from the charge storage 55 is transferred by the transmission transistor. Metal wiring (not shown) and pads (not shown) are also formed on the semiconductor substrate 110. Metal wiring and pads may be formed from metals with low resistivity to reduce signal delay, such as aluminum (Al), copper (Cu), silver (Ag), and alloys thereof, but are not limited to these. However, the structure is not limited to the above, and the metal wiring and pads may be placed below the light sensing elements (50a, 50b). A lower insulating layer 60 is formed on top of the metal wiring and pads. The lower insulating layer 60 can be formed from an inorganic insulating material such as silicon oxide and / or silicon nitride, or from a low dielectric constant (low K) material such as SiC, SiCOH, SiCO and / or SiOF. The lower insulating layer 60 has a trench 85 that exposes the charge storage 55. The trench can be filled with filler material. A color filter layer 70 is formed on top of the lower insulating layer 60. The color filter layer 70 includes a blue filter 70a formed on blue pixels and a red filter 70b formed on red pixels. Although a green filter is not shown in Figure 7, an additional green filter may be provided. An insulating layer 80 is formed on top of the color filter layer 70. The insulating layer 80 is flattened by removing the step caused by the color filter layer 70. The insulating layer 80 and the lower insulating layer 60 may include contact holes (not shown) that expose the pads, and the charge storage 55 of the green pixels through the holes (e.g., trenches 85). The aforementioned photoelectric element 100 is formed on the insulating layer 80. As described above, the photoelectric element 100 includes a first electrode 10, an active layer 30, and a second electrode 20. The photoelectric element 100 may be the same as the photoelectric element 100 in Figure 1, and in the exemplary embodiment, the photoelectric element 100 in Figure 1 can be replaced with the photoelectric element 200 in Figure 2. The first electrode 10 and the second electrode 20 may both be transparent electrodes, and the active layer 30 can selectively absorb and / or convert (convert to an electrical signal, for example, photoelectric conversion) light in the near-infrared wavelength region. In some embodiments, as shown in Figure 7, the active layer 30 can additionally selectively absorb and / or convert (to electrical signals, for example, photoelectric conversion) light in the visible light wavelength range (e.g., green light). A focusing lens (not shown) may be further formed on the photoelectric element 100. A focusing lens can control the direction of incident light and concentrate it to a single point. The focusing lens may, for example, be cylindrical or hemispherical in shape, but is not limited to these. Figure 7 shows a structure in which photoelectric elements 100 that selectively absorb light in the near-infrared wavelength region are stacked on a semiconductor substrate 110, but the present invention is not limited to this. Of the light incident on the organic sensor 700 on the upper surface of the photoelectric element 100, at least light in the near-infrared wavelength range is mainly absorbed by the active layer 30 and can be converted into photoelectricity, while visible light (e.g., blue, green, and / or red) wavelength range passes through the first electrode 10 and can be sensed by the photosensing elements (50a, 50b). Figure 8 is a cross-sectional view showing an organic sensor according to another embodiment. Referring to Figure 8, the organic sensor 800 according to this embodiment includes the visible light sensor 50 and the photoelectric element 100 as described above. Referring to Figure 8, in the organic sensor 800 according to this embodiment, the visible light sensor 50 may be a combination of a photodiode integrated on the semiconductor substrate 110 and a photoelectric element placed on the semiconductor substrate 110, and the photoelectric element 100 may be a separate photoelectric element. Therefore, if the organic sensor includes a photoelectric element (e.g., 100) configured to selectively absorb and / or convert (e.g., photoelectric conversion) light in a first near-infrared wavelength region, and additional sensors (e.g., 50a and / or 50b) configured to selectively absorb and / or convert (e.g., photoelectric conversion) light in a different wavelength region of incident light, the organic sensor may further include an additional photoelectric element (e.g., 50c) on a semiconductor substrate, the additional photoelectric element may be placed between the photoelectric element 100 and the semiconductor substrate 110, and the additional photoelectric element may be configured to selectively absorb and / or convert (e.g., photoelectric conversion) light in an additional wavelength region of incident light that is different from the first near-infrared wavelength region and different from the different wavelength region absorbed by the additional sensors (50a and / or 50b). The semiconductor substrate 110 integrates a blue light sensing element 50a, a red light sensing element 50b, a charge storage unit 55, and a transmission transistor (not shown). The blue light sensing element 50a and the red light sensing element 50b are photodiodes (for example, silicon-based photodiodes) spaced apart from each other in the horizontal direction on the semiconductor substrate 110. The blue light sensing element 50a is integrated into the blue pixel, and the red light sensing element 50b is integrated into the red pixel. A lower insulating layer 60 and a color filter layer 70 are formed on the semiconductor substrate 110. The color filter layer 70 includes a blue filter 70a superimposed on the blue light sensing element 50a and a red filter 70b superimposed on the red light sensing element 50b. An intermediate insulating layer 65 is formed on the color filter layer 70. The lower insulating layer 60 and the intermediate insulating layer 65 may have through-holes (e.g., trenches 85) that expose the charge storage 55. Through holes (e.g., trench 85) can be filled with filler. At least one of the lower insulating layer 60 or the intermediate insulating layer 65 can be omitted. An additional photoelectric element 850 is formed on the intermediate insulating layer 65. As shown in Figure 8, the additional photoelectric element 850 is also a green sensor 50c, but in some exemplary embodiments, the additional photoelectric element 850 can be configured to sense (e.g., selectively absorb and / or convert (to an electrical signal) (photoelectric conversion)) light in a wavelength region different from the green wavelength region, and the light in the above wavelength region may be another non-visible light wavelength region (e.g., a second near-infrared wavelength region) different from the first near-infrared wavelength region sensed by the photoelectric element 100. The additional photoelectric element 850 includes a first electrode (lower electrode) 101 and a second electrode (upper electrode) 102 facing each other, and an active layer 103 between the first electrode 101 and the second electrode 102. One of the first electrode 101 or the second electrode 102 is the anode, and the other is the cathode. The first electrode 101 and the second electrode 102 may both be transparent electrodes. The transparent electrodes can be formed from conductive oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO), aluminum tin oxide (AlTO), and fluorine-doped tin oxide (FTO), or from thin single or multiple layers of metal thin films. The active layer 103 may have a composition similar to that of the active layer 30 of the photoelectric element (100 and / or 200), and may include a near-infrared absorbing material. The active layer 103 may be a photoelectric conversion layer configured to selectively absorb and / or convert (e.g., absorbed light) (to an electrical signal) in at least a portion of the wavelength range (e.g., the wavelength spectrum of light). The active layer 103 can convert, for example, light in the green wavelength region (hereinafter referred to as "green light"), light in the blue wavelength region (hereinafter referred to as "blue light"), light in the red wavelength region (hereinafter referred to as "red light"), light in the infrared wavelength region (hereinafter referred to as "infrared light"), light in the ultraviolet wavelength region (hereinafter referred to as "ultraviolet light"), or combinations thereof, into electrical signals. For example, the active layer 103 can be configured to selectively absorb and / or convert (to an electrical signal) (e.g., photoelectric conversion) at least one of green light, blue light, red light, infrared light, or ultraviolet light. Here, selective absorption of at least one of green light, blue light, red light, infrared light, or ultraviolet light means that the light absorption spectrum is approximately 500 nm to approximately 600 nm, above approximately 380 nm and below approximately 500 nm, above approximately 600 nm and below approximately 700 nm, and above approximately 700 nm and below approximately 3000 nm, with the maximum absorption wavelength (λ) max This means that the optical absorption spectrum in that wavelength region is significantly higher than the spectra in other wavelength regions. The active layer 103 may include one or more p-type semiconductors and one or more n-type semiconductors that form a pn junction, generate excitons upon receiving light from the outside, and then separate the generated excitons into holes and electrons. The p-type semiconductor and the n-type semiconductor may each be independently light-absorbing materials; for example, at least one of the p-type semiconductor or the n-type semiconductor may be an organic light-absorbing material. For example, at least one of the p-type semiconductor or n-type semiconductor may be a wavelength-selective light-absorbing material that selectively absorbs light in a specific (or predetermined) wavelength range, or for example, at least one of the p-type semiconductor or n-type semiconductor may be a wavelength-selective organic light-absorbing material. p-type semiconductors and n-type semiconductors exhibit peak absorption wavelengths (λ) in the same wavelength region or other wavelength regions among the green wavelength region, blue wavelength region, red wavelength region, and infrared wavelength region. max ) can have. For example, a p-type semiconductor may be an organic material having a core structure containing electron-donating molecules, pi-conjugated linking groups, and electron-accepting molecules. A p-type semiconductor can be represented by, for example, chemical formula 2, but is not limited thereto. (chemical 2) EDG-HA-EAG ···Chemical formula 2 In the above chemical formula 2, HA may be a heterocyclic group having 2 to 30 carbon atoms and containing at least one of S, Se, Te, or Si; EDG may be an electron-donating group; and EAG may be an electron-accepting group. For example, a p-type semiconductor represented by chemical formula 2 can be represented by chemical formula 2A shown below. [ka] In chemical formula 2A, X is S, Se, Te, SO, SO2, or SiR a R b Even if that is the case, Ar may be a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, or a fusion ring thereof. Ar 1a and Ar 2aEach of these may independently be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. Ar 1a and Ar 2a They can exist independently or be linked together to form a fused ring. R 1a ~R 3a , R a , and R b Each of these may independently be hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C6 alkoxy group, a halogen, or a cyano group. For example, in chemical formula 2A, Ar 1a and Ar 2a Each of these may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenantrenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyridadinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted naphylidinyl group, a substituted or unsubstituted cinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted benzotriazinyl group, a substituted or unsubstituted pyridopyrazineyl group, a substituted or unsubstituted pyridopyrimidinyl group, and a substituted or unsubstituted pyridopyridazinyl group. For example, Ar in chemical formula 2A 1a and Ar2 a They are connected to each other to form a ring, or for example, Ar 1a and Ar 2a This is a single bond, -(CR g R h ) n2 -(n2 is 1 or 2), -O-, -S-, -Se-, -N=, -NR i -, -SiR j R k-, or GeR l R m - These are connected by one of the links to form a ring. Here, R g ~R m Each of these may independently be hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C6 alkoxy group, a halogen, or a cyano group. For example, a p-type semiconductor represented by chemical formula 2 can be represented by chemical formula 2B shown below. [ka] In chemical formula 2B, X 1 This may be Se, Te, O, S, SO, or SO2. Ar 3 This may be a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, or a fusion ring thereof. R 1 ~R 3 Each of these may independently be hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or a combination thereof. G is a single bond, -O-, -S-, -Se-, -N=, -(CR f R g ) k -, -NR h -, -SiR i R j -, -GeR k R l -,-(C(R m )=C(R n ))-, and SnR o R p It may be one of the following, where R f , R g , Rh , R i , R j , R k , R l , R m , R n , R o , and R p These are independently hydrogen, halogens, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C1-C10 alkoxy groups and substituted or unsubstituted C6-C12 aryl groups, R f and R g , R i and R j , R k and R l , R m and R n , and R o and R p They can exist independently or be connected to each other to form a ring. k may be 1 or 2, R 6a ~R 6d and R 7a ~R 7d These may independently be hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or a combination thereof. R 6a ~R 6d These can exist independently or, when two adjacent elements are linked together, form a fused ring. R 7a ~R 7d Each element can exist independently or two adjacent elements can be linked together to form a fused ring. For example, Ar, which has chemical formula 2B. 3 This may be a benzene ring, a naphthylene ring, an anthracene ring, a thiophene ring, a selenophene ring, a tellophene ring, a pyridine ring, a pyrimidine ring, or a fusion ring of two or more of these. The n-type semiconductor may be, for example, a fullerene or a fullerene derivative, but is not limited to this. The active layer 103 may be an intrinsic layer (I layer) in which a p-type semiconductor and an n-type semiconductor are mixed at a bulk heterojunction. Here, p-type semiconductors and n-type semiconductors can be mixed in a volume ratio of approximately 1:9 to 9:1, for example, approximately 2:8 to 8:2, approximately 3:7 to 7:3, approximately 4:6 to 6:4, or approximately 5:5. The active layer 103 may include a bilayer comprising a p-type layer containing the aforementioned p-type semiconductor and an n-type layer containing the aforementioned n-type semiconductor. Here, the thickness ratio of the p-type layer to the n-type layer may be approximately 1:9 to 9:1, for example, approximately 2:8 to 8:2, approximately 3:7 to 7:3, approximately 4:6 to 6:4, or approximately 5:5. The active layer 103 may further include a p-type layer and / or an n-type layer in addition to the intrinsic layer. The p-type layer may contain the aforementioned p-type semiconductor, and the n-type layer may contain the aforementioned n-type semiconductor. For example, these can be included in various combinations such as p-type layer / I-layer, I-layer / n-type layer, and p-type layer / I-layer / n-type layer. As shown in Figure 8, the active layer 103 is configured to selectively absorb and / or convert (to electrical signals, e.g., photoelectric conversion) green light, but is not limited thereto. In some embodiments, the active layer 103 can be configured to absorb and / or convert (to electrical signals, e.g., photoelectric conversion) blue light, red light, or any visible or non-visible light wavelength region (e.g., the second wavelength region of near-infrared light selectively transmitted by the photoelectric element 100). Figure 9 is a cross-sectional view showing an organic sensor according to another embodiment. Referring to Figure 9, the organic sensor 900 according to this embodiment includes a visible light sensor 50 and a photoelectric element 100 similar to that of the above embodiment. The visible light sensor 50 includes an additional photoelectric element 850 which includes a blue light sensing element 50a and a red light sensing element 50b integrated on a semiconductor substrate 110, and a green sensor 50c disposed on the semiconductor substrate 110. The blue light sensing element 50a and the red light sensing element 50b may be photodiodes (for example, silicon-based photodiodes), and the additional photoelectric element 850 may be the same as or a different green sensor 50c shown in Figure 8. The additional photoelectric element 850 includes a first electrode 101, an active layer 103, and a second electrode (upper electrode) 102, while the photoelectric element 100 includes a first electrode 10, an active layer 30, and a second electrode 20. However, in the organic sensor 900 according to this embodiment, the blue light sensing element 50a and the red light sensing element 50b integrated on the semiconductor substrate 110 are stacked in the vertical direction (for example, perpendicular to the upper surface 110S of the semiconductor substrate 110). The blue light sensing element 50a and the red light sensing element 50b can be configured to selectively absorb and / or convert (e.g., photoelectric conversion) light in each wavelength region depending on the stacking depth for sensing. In other words, the red light sensing element 50b, which is configured to selectively absorb and / or convert (to an electrical signal, e.g., photoelectric conversion) red light in the long-wavelength region, is positioned deeper from the surface of the semiconductor substrate 110 than the blue light sensing element 50a, which is configured to selectively absorb and / or convert (to an electrical signal, e.g., photoelectric conversion) blue light in the short-wavelength region. In this way, the absorption wavelength can be separated by the stacking depth, making it possible to omit the color filter layer 70. Figure 10 is a cross-sectional view showing an organic sensor according to one embodiment. Referring to Figure 10, the organic sensor 950 according to this embodiment includes a visible light sensor 50 and a photoelectric element 100 similar to that of the above embodiment. The visible light sensor 50 includes a blue light sensing element 50a, a green sensor 50c, and a red light sensing element 50b integrated on a semiconductor substrate 110, and the blue light sensing element 50a, green sensor 50c, and red light sensing element 50b may be photodiodes. In this embodiment, the organic sensor 950 has a blue light sensing element 50a, a green sensor 50c, and a red light sensing element 50b, all of which are stacked vertically on a semiconductor substrate 110. The blue light sensing element 50a, the green sensor 50c, and the red light sensing element 50b can be configured to selectively absorb and / or convert (e.g., photoelectric conversion) light in each wavelength region from the upper surface 110S depending on the stacking depth. Specifically, the red light sensing element 50b, configured to selectively absorb and / or convert (to an electrical signal, e.g., photoelectric conversion) red light in the long-wavelength region, is positioned deeper from the upper surface 110S of the semiconductor substrate 110 than the blue light sensing element 50a, which is configured to selectively absorb and / or convert (to an electrical signal, e.g., photoelectric conversion) blue light in the short-wavelength region. The green sensor 50c, configured to selectively absorb and / or convert (to an electrical signal, e.g., photoelectric conversion) green light in the intermediate-wavelength region, is positioned deeper from the upper surface 110S of the semiconductor substrate 110 than the blue light sensing element 50a, and closer to the upper surface 110S of the semiconductor substrate 110 than the red light sensing element 50b. In this way, the absorption wavelength can be separated by the stacking depth, making it possible to omit the color filter layer 70. Figure 11 is a cross-sectional view showing an organic sensor according to another embodiment. Referring to Figure 11, the organic sensor 970 according to this embodiment includes a first photoelectric element (e.g., infrared / near-infrared photoelectric element 1200d) configured to selectively absorb and / or convert (e.g., photoelectric conversion) light in the near-infrared wavelength spectrum of incident light (e.g., a first near-infrared wavelength region), and one or more additional photoelectric elements (e.g., 1200a-1200c) stacked vertically between the first photoelectric element and the semiconductor substrate 110, each of which additional photoelectric elements includes a separate photoelectric conversion layer and is configured to selectively absorb and / or convert (e.g., photoelectric conversion) a different (e.g., each) wavelength region of incident light, and the different (e.g., each) wavelength region may be a different visible and / or invisible light wavelength region from the first near-infrared wavelength region. For example, as shown in Figure 11, the organic sensor 970 includes additional photoelectric elements, including a red photoelectric element configured to selectively absorb and / or convert (to an electrical signal) (e.g., photoelectric conversion) light in the red wavelength spectrum of incident light, a green photoelectric element configured to selectively absorb and / or convert (to an electrical signal) (e.g., photoelectric conversion) light in the green wavelength spectrum of incident light, and a blue photoelectric element configured to selectively absorb and / or convert (to an electrical signal) (e.g., photoelectric conversion) light in the blue wavelength spectrum of incident light, which are stacked vertically (e.g., in the z direction). Therefore, as shown in Figure 11, the organic sensor 970 includes a plurality of photoelectric elements (1200a to 1200d) stacked vertically on the semiconductor substrate 110, and the plurality of photoelectric elements (1200a to 1200d) can be superimposed in a direction that extends perpendicularly to the upper surface 110S of the semiconductor substrate 110. The organic sensor 970 includes a first photoelectric element (e.g., a fourth photoelectric element 1200d) configured to selectively absorb and / or convert light in a first near-infrared wavelength region, plus a plurality of additional photoelectric elements (1200a to 1200c). However, in some exemplary embodiments, the organic sensor 970 may be limited to including a single additional photoelectric element (e.g., any one of 1200a to 1200c) between the photoelectric element 1200d and the semiconductor substrate 110. The organic sensor 970 according to this embodiment includes a semiconductor substrate 110, a lower insulating layer 80a, an intermediate insulating layer 80b, another intermediate insulating layer 80c, an upper insulating layer 80d, a first photoelectric element 1200a, a second photoelectric element 1200b, a third photoelectric element 1200c, and a fourth photoelectric element 1200d. In some exemplary embodiments, the fourth photoelectric element 1200d may be a first photoelectric element configured to selectively absorb and / or convert (e.g., photoelectric conversion) light in a first near-infrared wavelength region, and the first to third photoelectric elements (1200a to 1200c) may be at least one additional photoelectric element configured to selectively absorb and / or convert (e.g., photoelectric conversion) light in one or more separate wavelength regions different from the first near-infrared wavelength region. As shown in the figure, the first to fourth photoelectric elements (1200a to 1200d) are stacked on the semiconductor substrate 110 so as to overlap each other in a direction that extends perpendicularly to the upper surface 110S of the semiconductor substrate 110. The semiconductor substrate 110 may be a silicon substrate, and a transmission transistor (not shown) and a charge storage are integrated on it. The first to third photoelectric elements (1200a to 1200c) can have the same structure as the additional photoelectric element 850 shown in Figures 8 and 9. However, each separate photoelectric element (1200a to 1200c) can be configured to photoelectrically convert a different wavelength region of visible light and / or non-visible light (e.g., near-infrared light), and the photoelectric conversion layers (1230a to 1230c) can selectively absorb and / or convert (e.g., photoelectrically convert) light in other visible and / or non-visible light wavelength regions by having the same structure and / or composition as the various exemplary embodiments (e.g., different exemplary embodiments) of the aforementioned active layer 103 and / or active layer 30, and may include a near-infrared absorbing material. The first photoelectric element 1200a is formed on the lower insulating layer 80a. The first photoelectric element 1200a includes a photoelectric conversion layer 1230a. The first photoelectric element 1200a may be any one of the photoelectric elements according to any embodiment described herein. The photoelectric conversion layer 1230a can selectively absorb and / or convert (to an electrical signal) one of the infrared, red, blue, and green wavelength spectra of the incident light (e.g., photoelectric conversion). For example, the first photoelectric element 1200a may be a blue photoelectric element. The intermediate insulating layer 80b is formed on the first photoelectric element 1200a. The second photoelectric element 1200b is formed on the intermediate insulating layer 80b. The second photoelectric element 1200b includes a photoelectric conversion layer 1230b. The second photoelectric element 1200b may be a photoelectric element according to any one of the embodiments described herein. The photoelectric conversion layer 1230b can selectively absorb and / or convert (to an electrical signal) one of the infrared, red, blue, or green wavelength spectra of the incident light (e.g., photoelectric conversion). For example, the second photoelectric element 1200b may be a green photoelectric element. Another intermediate insulating layer 80c is formed on top of the second photoelectric element 1200b. The third photoelectric element 1200c is formed on the intermediate insulating layer 80c. The third photoelectric element 1200c includes a photoelectric conversion layer 1230c. The third photoelectric element 1200c may be a photoelectric element according to any one embodiment of the photoelectric elements described herein. The photoelectric conversion layer 1230c can selectively absorb and / or convert (to an electrical signal) one of the infrared, red, blue, or green wavelength spectra of the incident light (e.g., photoelectric conversion). For example, the third photoelectric element 1200c may be a red photoelectric element. An upper insulating layer 80d is formed on the third photoelectric element 1200c. The lower insulating layer 80a, the intermediate insulating layers (80b, 80c), and the upper insulating layer 80d have multiple through-holes that expose the charge storage sections (55a, 55b, 55c, 55d). The fourth photoelectric element 1200d is formed on the upper insulating layer 80d. The fourth photoelectric element 1200d includes a photoelectric conversion layer 1230d. The fourth photoelectric element 1200d may be a photoelectric element according to any one of the embodiments described herein. The photoelectric conversion layer 1230d can selectively absorb and / or convert (to an electrical signal) one of the infrared, red, blue, or green wavelengths of light (e.g., photoelectric conversion). For example, the fourth photoelectric element 1200d may be an infrared / near-infrared photoelectric element that includes a near-infrared absorbing material. In the drawing, the first photoelectric element 1200a, the second photoelectric element 1200b, the third photoelectric element 1200c, and the fourth photoelectric element 1200d are stacked in sequence, but the present invention is not limited to this and can be stacked in various orders. As described above, since the first photoelectric element 1200a, the second photoelectric element 1200b, the third photoelectric element 1200c, and the fourth photoelectric element 1200d have a stacked structure, the size of the organic sensor can be reduced and miniaturization can be achieved. The aforementioned organic sensors can be applied to a variety of electronic devices, such as cameras, camcorders, mobile phones incorporating them, display devices, security devices, or medical devices, but are not limited to these.

[0089] Figure 12 is a block diagram showing a schematic configuration of a digital camera including an image sensor according to one embodiment of the present invention. Referring to Figure 12, the digital camera 1000 includes a lens 1010, an image sensor 1020, a motor 1030, and an engine 1040. The image sensor 1020 may be any one of the image sensors according to the embodiments shown in Figures 3 to 11 above. The lens 1010 focuses the incident light onto the image sensor 1020. The image sensor 1020 generates RGB data from the light received through the lens 1010. In one embodiment, the image sensor 1020 interfaces with the engine 1040. Motor 1030 adjusts the focus of lens 1010 or adjusts the shutter in response to a control signal received from engine 1040. Engine 1040 controls the image sensor 1020 and motor 1030. Engine 1040 is connected to the host / application 1050.

[0090] Figure 13 is a block diagram illustrating an electronic device according to one embodiment of the present invention. Referring to Figure 13, the electronic device 1100 includes a processor 1120, a memory 1130, and an image sensor 1140, all of which are electrically connected by a bus 1110. The image sensor 1140 may be an image sensor and / or an organic sensor according to the embodiments described above. Memory 1130 may be a non-transitory computer-readable medium that stores instruction programs.

[0091] The memory 1130 may be a non-volatile memory such as flash memory, PRAM (Phase-Change Random Access Memory), MRAM (Magneto-Resistive RAM), ReRAM (Resistive RAM), or FRAM (Ferro-electric RAM), or a volatile memory such as static RAM (SRAM), dynamic RAM (DRAM), or synchronous DRAM (SDRAM).

[0092] The processor 1120 executes a stored instruction program to perform one or more functions. For example, the processor 1120 is configured to process electrical signals generated by the image sensor 1140. The processor 1120 may be processing circuitry, such as hardware including logic circuits; a hardware / software combination, such as a processor that executes software; or a combination of these. For example, processing circuits can more specifically include central processing units (CPUs), arithmetic logic units (ALUs), digital signal processors, microcomputers, FPGAs (Field Programmable Gate Arrays), SoCs (System-on-Chip), programmable logic units, microprocessors, and ASICs (application-specific integrated circuits). The processor 1120 is configured to generate output (for example, an image displayed on a display interface) based on such processing. The embodiments described above will be explained in more detail below through the examples. However, the following embodiments are for illustrative purposes only and do not limit the scope of rights.

[0093] <<Examples>> <Example of synthesis> [Synthesis Example 1: Synthesis of the compound represented by chemical formula 1-1] [ka] [ka]

[0094] i) First step: Synthesis of compound 1-1C Compound 1-1A (4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole, 0.71 g, 1.86 mmol) and compound 1-1B (4-phenyl-2-(tributylstannyl)-4H-thieno[3,2-b]indole, 2 g, 3.71 mmol) were dissolved in toluene (18 ml) in a round-bottom flask under nitrogen pressure, and then tetrakis(triphenylphosphine)-palladium(0), 0.11 g, 0.093 mmol was added. The mixture was then heated to 110°C and stirred under reflux for 24 hours. After the reaction was complete, the toluene was removed and the reaction mixture was concentrated. The mixture was then separated by silica chromatography (volume ratio of eluent:dichloromethane:n-hexane = 1:4), and precipitated in 50 ml of methanol to obtain 0.95 g (yield: 70%) of compound 1-1C.

[0095] ii) Second stage: Synthesis of compound 1-1D Compound 1-1C (0.56 g, 0.76 mmol) was dissolved in acetic acid (10 ml) in a round-bottom flask under nitrogen pressure, and then iron powder (0.33 g, 5.91 mmol) was added. The mixture was then heated to 80°C and stirred for 12 hours. After the reaction mixture was cooled to room temperature, distilled water was added. After extraction with dichloromethane, the organic layer was dried using MgSO4. The filtered liquid containing MgSO4 was concentrated to obtain 0.28 g (yield: 55%) of compound 1-1D.

[0096] iii) Third stage: Synthesis of the compound represented by chemical formula 1-1 Compound 1-1D (0.28 g, 0.42 mmol) was dissolved in pyridine (5 ml) in a round-bottom flask under nitrogen pressure. Then, N-thionylaniline (0.19 ml, 1.69 mmol) and chlorotrimethylsilane (0.38 ml, 2.97 mmol) were added, and the mixture was stirred at 80°C for 12 hours. After cooling the reaction mixture to room temperature, it was precipitated in 50 ml of methanol and filtered. The resulting solid was thoroughly washed with dichloromethane and ethyl acetate to obtain 0.15 g (yield: 51%) of the compound represented by chemical formula 1-1. MALDI-TOF molecular weight analysis: 688.376m / z

[0097] [Synthesis Example 2: Synthesis of Compounds Represented by Chemical Formulas 1-2] [ka] [ka]

[0098] Compound 1-1D (0.05 g, 0.076 mmol) from Synthesis Example 1 was dissolved in ethanol / chloroform in a round-bottom flask under nitrogen pressure. Then, selenium dioxide (0.011 g, 0.091 mmol) was added, and the mixture was stirred at 80°C for 12 hours. After the reaction was complete, the reactants were concentrated, and the resulting solid was thoroughly washed with dichloromethane and ethyl acetate to obtain 0.09 g (yield: 40%) of the compound represented by chemical formula 1-2. MALDI-TOF molecular weight analysis: 735.953m / z

[0099] [Synthesis Example 3: Synthesis of Compounds Represented by Chemical Formulas 1-3] [ka] [ka]

[0100] Compound 1-1D (0.02 g, 0.03 mmol) from Synthesis Example 1 was dissolved in acetic acid / chloroform in a round-bottom flask under nitrogen pressure. Then, phenanthrene-9,10-dione (0.007 g, 0.033 mmol) was added, and the mixture was stirred at 55°C for 12 hours. After adding distilled water to the reaction product, the resulting solid was filtered and then thoroughly washed with hexane and ethyl acetate to obtain 0.016 g (yield: 64%) of the compound represented by chemical formula 1-3. MALDI-TOF molecular weight analysis: 832.487m / z

[0101] [Synthesis Example 4: Synthesis of Compounds Represented by Chemical Formulas 1-4] [ka] [ka]

[0102] i) First step: Synthesis of compound 1-4C Compounds 1-4A (4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole, 0.8 g, 1.86 mmol) and 1-4B (4-methyl-2-(tributylstannyl)-4H-thieno[3,2-b]indole, 12 g, 3.71 mmol) were dissolved in toluene (20 ml) in a round-bottom flask under nitrogen pressure, and then tetrakis(triphenylphosphine)-palladium(0) (0.12 g, 0.1 mmol) was added. The mixture was then heated to 110°C and stirred under reflux for 24 hours. After the reaction was complete, the toluene was removed and the reaction mixture was concentrated. The mixture was then separated by silica chromatography (volume ratio of eluent:dichloromethane:n-hexane = 1:4), and precipitated in 50 ml of methanol to obtain 0.9 g (yield: 72%) of compound 1-4C.

[0103] ii) Second stage: Synthesis of compounds 1-4D Compound 1-4C (0.34 g, 0.57 mmol) was dissolved in ethanol (9 ml) and ethyl acetate (18 ml) in a round-bottom flask under nitrogen pressure, and then Palladium on Carbon (0.3 g, 0.28 mmol) and ammonium formate (3.59 g, 56.98 mmol) were added. The mixture was then heated to 60°C and stirred for 12 hours. After cooling the reactants to room temperature, they were separated by silica chromatography (eluent:dichloromethane:n-hexane = 2:1 volume ratio), and then precipitated in 100 ml of hexane to obtain 0.16 g (yield: 52%) of compound 1-4D.

[0104] iii) Third stage: Synthesis of compounds represented by chemical formulas 1-4 Compound 1-4D (0.1 g, 0.42 mmol) was dissolved in pyridine (3 ml) in a round-bottom flask under nitrogen pressure. Then, N-thionylaniline (0.08 ml, 0.74 mmol) and chlorotrimethylsilane (0.16 ml, 1.3 mmol) were added, and the mixture was stirred at 80°C for 12 hours. After cooling the reaction mixture to room temperature, it was precipitated in 30 ml of methanol and filtered. The resulting solid was thoroughly washed with dichloromethane and ethyl acetate to obtain 0.06 g (yield: 59%) of the compound represented by chemical formula 1-4.

[0105] [Synthesis Example 5: Synthesis of Compounds Represented by Chemical Formulas 1-5] [ka] [ka]

[0106] Compound 1-4D (0.03 g, 0.055 mmol) was dissolved in ethanol / chloroform in a round-bottom flask under nitrogen pressure, and then selenium dioxide (0.0074 g, 0.067 mmol) was added and the mixture was stirred at 80°C for 12 hours. After the reaction was complete, the reactants were concentrated, and the resulting solid was thoroughly washed with dichloromethane and ethyl acetate to obtain 0.02 g (yield: 59%) of the compound represented by chemical formula 1-5.

[0107] [Synthesis Example 6: Synthesis of Compounds Represented by Chemical Formulas 1-6] [ka] [ka]

[0108] Compound 1-4D (0.03 g, 0.055 mmol) from Synthesis Example 4 was dissolved in acetic acid / chloroform in a round-bottom flask under nitrogen pressure. Then, phenanthrene-9,10-dione (0.012 g, 0.061 mmol) was added, and the mixture was stirred at 55°C for 12 hours. After adding distilled water to the reaction product, the resulting solid was filtered and then thoroughly washed with hexane and ethyl acetate to obtain 0.02 g (yield: 59%) of the compound represented by chemical formula 1-6.

[0109] [Synthesis Example 7: Synthesis of Compounds Represented by Chemical Formulas 1-7] [ka] [ka]

[0110] i) First step: Synthesis of compounds 1-7C Compound 1-7A (4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole, 0.71 g, 1.86 mmol) and compound 1-7B (8-phenyl-2-(tributylstannyl)-8H-thieno[2,3-b]indole, 2 g, 3.71 mmol) were dissolved in toluene (18 ml) in a round-bottom flask under nitrogen pressure, and then tetrakis(triphenylphosphine)-palladium(0) (0.11 g, 0.093 mmol) was added. The mixture was then heated to 110°C and stirred under reflux for 24 hours. After the reaction was complete, the toluene was removed and the reaction mixture was concentrated. The mixture was then separated by silica chromatography (volume ratio of eluent:dichloromethane:n-hexane = 1:4), and precipitated in 50 ml of methanol to obtain 0.1 g (yield: 74%) of compound 1-7C.

[0111] ii) Second stage: Synthesis of compounds 1-7D Compound 1-7C (0.6 g, 0.83 mmol) was dissolved in acetic acid (20 ml) in a round-bottom flask under nitrogen pressure, and then iron powder (1.39 g, 24.97 mmol) was added. The mixture was then heated to 80°C and stirred for 12 hours. After the reaction mixture was cooled to room temperature, distilled water was added. After extraction with dichloromethane, the organic layer was dried using MgSO4. The filtered liquid containing MgSO4 was concentrated to obtain 0.31 g (yield: 56%) of compound 1-7D.

[0112] iii) Third stage: Synthesis of compounds represented by chemical formulas 1-7 Compound 1-7D (0.1 g, 0.15 mmol) was dissolved in pyridine (2 ml) in a round-bottom flask under nitrogen pressure. Then, N-thionylaniline (0.07 ml, 0.6 mmol) and chlorotrimethylsilane (0.13 ml, 1.06 mmol) were added, and the mixture was stirred at 80°C for 12 hours. After cooling the reaction mixture to room temperature, it was precipitated in 30 ml of methanol and filtered through paper. The resulting solid was thoroughly washed with dichloromethane and ethyl acetate to obtain 0.08 g (yield: 77%) of the compound represented by chemical formula 1-7.

[0113] [Synthesis Example 8: Synthesis of Compounds Represented by Chemical Formulas 1-8] [ka] [ka]

[0114] Compound 1-7D (0.1 g, 0.15 mmol) from Synthesis Example 7 was dissolved in ethanol / chloroform in a round-bottom flask under nitrogen pressure. Then, selenium dioxide (0.02 g, 0.18 mmol) was added and the mixture was stirred at 80°C for 12 hours. After the reaction was complete, the reactants were concentrated, and the resulting solid was thoroughly washed with dichloromethane and ethyl acetate to obtain 0.07 g (yield: 63%) of the compound represented by chemical formula 1-8.

[0115] Synthesis Example 9: Synthesis of Compounds Represented by Chemical Formulas 1-9] [ka] [ka]

[0116] Compound 1-7D (0.1 g, 0.15 mmol) from Synthesis Example 7 was dissolved in acetic acid / chloroform in a round-bottom flask under nitrogen pressure. Then, phenanthrene-9,10-dione (0.038 g, 0.18 mmol) was added, and the mixture was stirred at 55°C for 12 hours. After adding distilled water to the reaction mixture, the resulting solid was filtered and then thoroughly washed with hexane and ethyl acetate to obtain 0.09 g of the product (yield: 72%). MALDI-TOF molecular weight analysis: 832.487m / z

[0117] [Comparative Synthesis Example 1: Synthesis of the compound represented by chemical formula 2-1] [ka]

[0118] N,N-diphenyl-5-(tributylstannyl)thiophen-2-amine (0.18 g, 0.34 mmol), 4,8-dibromobenzo[1,2-c;4,5-c]bis([1,2,5]thiadiazole) (0.1 g, 0.28 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.008 g, 0.014 mmol) were dissolved in 5 ml of dry toluene and stirred at 110°C for 18 hours. After the reaction was complete, the toluene was concentrated and evaporated, then precipitated with dichloromethane to obtain 0.1 g of the product (yield: 52%). MALDI-TOF molecular weight analysis: 692m / z

[0119] [Comparative Synthesis Example 2: Synthesis of the compound represented by chemical formula 2-2] [ka] [ka]

[0120] In a round-bottom flask, under nitrogen pressure, 4,9-dibromo-[1,2,5]thiadiazolo[3,4-g]quinoxaline (compound (2-1A)) (1.13 g, 3.26 mmol) and N,N-diphenyl-5-(tributylstannyl)thiophen-2-amine (compound (2-1B)) (4.4 g, 8.14 mmol) were dissolved in toluene (15 ml), and then tetrakis(triphenylphosphine)-palladium(0) (0.376 g, 0.326 mmol) was added. The mixture was then heated to 110°C and stirred under reflux for 24 hours. After cooling the reaction mixture to room temperature (24°C), the mixture was concentrated, and then ethyl acetate was added. The resulting solid was then filtered and washed with n-hexane / ethyl acetate / methanol. The obtained solid was vacuum-dried to obtain a green solid compound represented by chemical formula 2-2 (1.5 g). 1 H NMR (500MHz, CDCl3): d8.92 (d, 2H), d8.75 (s, 2H), d7.35 (t, 8H), d7.30 (d, 8H), d7.14 (t, 4H), d6.75 (d, 2H). UPLC-MS:[M+H] + 687.06

[0121] [Comparative Synthesis Example 3: Synthesis of Compounds Represented by Chemical Formula 2-3] The compounds represented by chemical formulas 2-3 shown below were synthesized using the method described in the paper (D.Ma, ZYWang et al. J.Phys.Chem.C, 2009, 113, 1589-1595). [ka]

[0122] [Comparative Synthesis Example 4: Synthesis of Compounds Represented by Chemical Formulas 2-4] [ka] [ka]

[0123] Compounds 2-4A (4,9-dibromo-[1,2,5]thiadiazolo[3,4-g]quinoxaline, 530 mg, 1.53 mmol), 2-4B (diiphenylamine, 646 mg, 3.82 mmol), and sodium tert-butoxide (317 mg, 4.59 mmol) were dissolved in toluene (10 ml) under nitrogen pressure in a round-bottom flask, after which bis(tri-tert-butylphosphine)palladium(0) (78 mg, 0.153 mmol) was added. The mixture was then heated to 110°C and stirred under reflux for 24 hours. After cooling the reaction mixture to room temperature (24°C), the mixture was concentrated, and then ethyl acetate, distilled water, and ammonium chloride aqueous solution were added sequentially. The organic layer was extracted using ethyl acetate and then dried with MgSO4. After filtering the MgSO4, the solution was concentrated, and silica chromatography was performed on the concentrate (volume ratio of eluent:ethyl acetate:hexane = 1:4). The purified product was vacuum-dried to obtain 120 mg (yield: 15%) of the compound represented by chemical formula 2-4 as a green solid. 1 H NMR (300MHz, CD2Cl2): d8.57 (s, 2H), d7.19 (d, 8H), d7.06 (d, 8H), d6.98 (t, 4H). UPLC-MS:[M+H] + 523.14

[0124] [Comparative Synthesis Example 5: Synthesis of Compounds Represented by Chemical Formulas 2-5] The compounds represented by chemical formulas 2-5 shown below were synthesized using the method described in Scheme 1 of the paper (ACS Nano, Highly Stable Organic Small Molecular Nanoparticles as an Advanced and Biocompatible Phototheranostic Agent of Tumor in Living Mice, 2017, 7177-7188). [ka]

[0125] <<Evaluation I: Absorption Characteristics>> The compounds produced by Synthesis Example 1, Comparative Synthesis Example 3, and Comparative Synthesis Example 4 were mixed with dichloromethane in a solution of 1 × 10⁻¹⁶ units. -5 The compound was dissolved at concentration M to prepare a solution, and its absorbance properties in solution were evaluated. Furthermore, a 30 nm thin film was formed by depositing the compound according to Synthesis Example 1 onto a glass substrate using a vapor deposition method, and the absorbance characteristics of the thin film were evaluated. On the other hand, the compounds produced by comparative synthesis example 1 and comparative synthesis example 2 could not be evaluated because vapor deposition was not possible. Absorption characteristics were measured using a Shimadzu UV-3600 Plus UV-Vis-NIR spectrometer, with the maximum absorption wavelength (λ) being measured. max The following parameters were measured. The results are shown in Table 1.

[0126] On the other hand, DFT and TD-DFT calculations (wB97X-D function with 6-311G(d,p) basis set) were performed on the compounds produced by Synthesis Examples 2-9 and Comparative Synthesis Example 5 using the Gaussian09 (G09) program, assuming a toluene solution. The results are shown in Table 2.

[0127] [Table 1] [Table 2] Referring to Tables 1 and 2, it can be seen that the compounds produced by Synthesis Examples 1-9 exhibit better wavelength absorption in the near-infrared wavelength region compared to the compounds produced by Comparative Synthesis Examples 1-5.

[0128] For the compounds synthesized in Examples 1-7, the "Oscillator Strength" was calculated using the Gaussian09 program with DFT B3LYP / 6-311G(d,p) level and is listed in Table 3. [Table 3] Referring to Table 3, the high Oscillator Strength values ​​of the compounds synthesized in Examples 1-7 suggest that they have high absorption coefficients.

[0129] <<Evaluation II: Vapor Deposition Characteristics>> The vapor deposition properties of the compounds synthesized in Synthesis Examples 1-9 and Comparative Synthesis Examples 1-5 were evaluated. Vapor deposition characteristics were evaluated using thermogravimetric analysis (TGA). The compound was sublimated under a high vacuum of 10 Pa or less, and thermal stability was assessed by measuring the weight decrease due to temperature increase.

[0130] The results of Synthesis Examples 1-3, Comparative Synthesis Example 1, and Comparative Synthesis Example 2 are shown in Table 4. [Table 4] Referring to Table 4, it can be confirmed that the compounds synthesized in Examples 1-3 are suitable for vapor deposition. On the other hand, the compounds produced by comparative synthesis example 1 and comparative synthesis example 2 could not be evaluated because vapor deposition was not possible.

[0131] <<Examples and Comparative Examples: Fabrication of Photoelectric Devices>> ITO was deposited onto a glass substrate by sputtering to form a 150nm thick anode. Next, compounds from synthesis examples 1-9 and comparative synthesis examples 3-5 were co-deposited onto the anode in a 1:1 volume ratio with C60 to form an active layer (photoelectric conversion layer) with a thickness of 150 nm. Next, C60 was deposited on the active layer to form an auxiliary layer with a thickness of 30 nm. Next, ITO was sputtered onto the auxiliary layer to form a 7nm thick cathode. Next, aluminum oxide (Al2O3) was deposited onto the cathode to form a 50 nm thick anti-reflective layer, and the photoelectric elements according to Examples 1-9 and Comparative Examples 3-5 were fabricated by sealing with a glass plate.

[0132] <<Evaluation III: Photoelectric Conversion Efficiency>> The photoelectric conversion efficiency of the photoelectric elements in Examples 1-9 and Comparative Examples 3-5 was evaluated. The photoelectric conversion efficiency was measured using an IPCE measurement system (TNE tech, South Korea). First, the device was calibrated using a Si photodiode (Hamamatsu, Japan), then the photoelectric element was mounted on the device, and measurements were taken in the wavelength range of approximately 400 nm to 1600 nm.

[0133] The results for Example 1 and Comparative Example 4 are shown in Figure 14. Figure 14 is a graph showing the results of measuring the photoelectric conversion efficiency (Normalized EQE) of photoelectric elements in Example 1 and Comparative Example 4. Referring to Figure 14, the photoelectric element according to Example 1 is superior to the photoelectric element according to Comparative Example 4. Approximately 1000nmIt can be confirmed that it exhibits excellent photoelectric conversion efficiency in the long wavelength region.

[0134] Furthermore, the present invention is not limited to the embodiments described above. It can be modified and implemented in various ways without departing from the technical scope of the present invention. [Explanation of Symbols]

[0135] 10, 101 1st electrode 20, 102 2nd electrode 30, 103 active layer 40 1st auxiliary layer 45 Second auxiliary layer 50a, 50b, 50c Light sensing elements 55 Charge Storage 60 Lower insulating layer 70a, 70b, 70c (red, green, blue) color filters 80 (Upper) Insulating Layer 85 Trench 95 Dual Bandpass Filter 100, 200 photoelectric elements 100A First Infrared Light Sensor 110 Semiconductor substrates 120 Second infrared light sensor 300, 400, 500, 600, 700, 800, 900 Organic Sensors 1000 Digital Cameras 1010 Lens 1020 Image Sensor 1030 Motor 1040 engine 1050 Host / Application 1100 Electronic equipment 1110 Bus 1120 processors 1130 memory 1140 Image Sensor

Claims

1. It is a near-infrared absorbing material, A near-infrared absorbing material characterized by containing a compound represented by the chemical formula 1 shown below. 【Chemistry 1】 (In the above chemical formula 1, Ar is a benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetracene ring, or a substituted or unsubstituted pyrene ring. X １ is S, Se, Te, S(=O), or S(=O) ２ And, X ２ is O, S, Se, Te, CR ｘ -CR ｙ CR ｘｘ -CR ｙｙ or S(=O) (where R ｘ and R ｙ are each independently hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, a halogen, a cyano group, or a combination thereof, and R ｘｘ and R ｙｙ are linked to each other to form an aromatic ring or a heteroaromatic ring). Ar １ and Ar ２ These are, independently, heteroarenes containing sulfur. Ar １ and Ar ２ They are either identical or different, and are selected from the following chemical formulas C-1-1 to C-1-3. Ar ３ and Ar ４ Each of these is independently a substituted or unsubstituted arene with 6 to 30 carbon atoms, a substituted or unsubstituted heteroarene with 3 to 30 carbon atoms, or a condensed ring thereof. R １ and R ２ Each of these is independently hydrogen, deuterium, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C1-C10 alkoxy group, substituted or unsubstituted C6-C10 aryl group, or substituted or unsubstituted C3-C10 heteroaryl group. L １ and L ２ It is a single bond, 【Chemistry C-1-1】 【Chemistry C-1-2】 【Chemistry C-1-3】 In the aforementioned chemical formulas C-1-1 to C-1-3, The hydrogen atoms in each aromatic ring are halogens, cyano groups, C1-C30 alkyl groups, C1-C30 alkoxy groups, C1-C30 haloalkyl groups, and -SiH. ３ It can be substituted with an alkylsilyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. Y １ is S, S(=O), or S(=O)², Y ２ are O, S, Se, Te, S(=O), S(=O) ２ , NR ａ２ , SiR ｂ２ R ｃ２ , GeR ｄ２ R ｅ２ , or CR ｆ２ R ｇ２ (where R ａ２ , R ｂ２ , R ｃ２ , R ｄ２ , R ｅ２ , R ｆ２ , and R ｇ２ These are, independently, hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, and -SiH ３ , alkylsilyl group having 1 to 10 carbon atoms, -NH ３ (These include alkylamine groups having 1 to 10 carbon atoms, arylamine groups having 6 to 10 carbon atoms, aryl groups having 6 to 14 carbon atoms, aryloxy groups having 6 to 14 carbon atoms, heteroaryl groups having 3 to 12 carbon atoms, halogens, cyano groups, or combinations thereof.) R b2 and R ｃ２ , R ｄ２ and R ｅ２ , and R ｆ２ and R ｇ２ These elements either exist independently or combine with each other to form a spiro ring. * located outside at least one aromatic ring is a linking site with Ar in chemical formula 1, and * located inside at least one aromatic ring is R in chemical formula 1. １ N(R) １ ) - Containing ring, and R ２ N(R) of chemical formula 1, which includes ２ ) - This is the connection point with the containing ring.

2. The near-infrared absorbing material according to claim 1, characterized in that Ar in the chemical formula 1 is one of the moieties represented by the chemical formula group A-1 shown below. 【Chemistry A-1】 (Among the chemical formula group A-1 above, Each aromatic ring's hydrogen can be replaced with a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, a silyl group, or a C1-C10 alkylsilyl group. The asterisk inside the aromatic ring represents the -N-X in chemical formula 1. １ -N- containing ring, and -N=X ２ = This is the part that bonds with the N-containing ring, The asterisks (*) in the left and right linking groups are Ar in chemical formula 1. １ and Ar ２ This is the part that connects to it.

3. In the above chemical formula 1, X ２ CR ｘｘ -CR ｙｙ If R ｘｘ and R ｙｙ The near-infrared absorbing material according to claim 1, characterized in that the aromatic ring formed by the linkage of these elements is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted acenaphthene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetracene ring, or a substituted or unsubstituted pyrene ring.

4. In the above chemical formula 1, X ２ CR ｘｘ -CR ｙｙ If R ｘｘ and R ｙｙ The near-infrared absorber according to claim 1, characterized in that the aromatic ring formed by the linkage of these elements is a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted quinazoline ring, a substituted or unsubstituted phenanthroline ring, a substituted or unsubstituted pyrimidine ring, or a substituted or unsubstituted benzodithiophene ring.

5. In the above chemical formula 1, X ２ CR ｘｘ -CR ｙｙ If R ｘｘ and R ｙｙ The near-infrared absorbing material according to claim 1, characterized in that the aromatic ring formed by the linkage of these elements is one of the moieties represented by the chemical formula group B-1 shown below. 【Chemical B-1】 (Among the above chemical formula group B-1, The hydrogen atoms in each aromatic ring are halogens, cyano groups, C1-C30 alkyl groups, C1-C30 alkoxy groups, C1-C30 haloalkyl groups, and -SiH. ３ It can be substituted with an alkylsilyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. The asterisk inside the aromatic ring represents CR. ｘｘ -CR ｙｙ (This is the part that bonds with carbon.)

6. In the above chemical formula 1, X ２ CR ｘｘ -CR ｙｙ If R ｘｘ and R ｙｙ The near-infrared absorbing material according to claim 1, characterized in that the aromatic ring formed by the linkage of these elements is one of the moieties represented by chemical formula group B-2 shown below. 【B-2】 (Among the chemical formula group B-2 above, The hydrogen atoms in each aromatic ring are halogens, cyano groups, C1-C30 alkyl groups, C1-C30 alkoxy groups, C1-C30 haloalkyl groups, and -SiH. ３ It can be substituted with an alkylsilyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. The asterisk inside the aromatic ring represents CR. ｘｘ -CR ｙｙ (This is the part that bonds with carbon.)

7. In the above chemical formula 1, X ２ CR ｘｘ -CR ｙｙ If R ｘｘ and R ｙｙ The near-infrared absorbing material according to claim 1, characterized in that the aromatic ring formed by the linkage of these elements is one of the moieties represented by chemical formula B-3-1 or chemical formula B-3-2 shown below. 【Chemistry B-3-1】 【Chemistry B-3-2】 (In the above chemical formulas B-3-1 and B-3-2, Ar １１ and Ar １２ Each is independently selected from substituted or unsubstituted arenes with 6 to 30 carbon atoms and substituted or unsubstituted heteroarenes with 3 to 30 carbon atoms. Z in Chemical Formula B-3-1 １ and Z ２ are each independently CR ａ or N (where R ａ is hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 30 carbon atoms, -NH ２ , an alkylamine group having 1 to 30 carbon atoms, an arylamine group having 6 to The hydrogen atoms in each aromatic ring are halogens, cyano groups, C1-C30 alkyl groups, C1-C30 alkoxy groups, C1-C30 haloalkyl groups, and -SiH. ３ It can be substituted with an alkylsilyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. The asterisk inside the aromatic ring represents CR. ｘｘ -CR ｙｙ (This is the part that bonds with carbon.)

8. The near-infrared absorbing material according to claim 7, characterized in that the moiety represented by the chemical formula B-3-1 is represented by the chemical formula group B-3-11 shown below, and the moiety represented by the chemical formula B-3-2 is represented by the chemical formula group B-3-21 shown below. 【Chemical B-3-11】 (Among the above chemical formula group B-3-11, The hydrogen of each aromatic ring can be substituted with a halogen, a cyano group, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms, The asterisk inside the aromatic ring represents CR. ｘｘ -CR ｙｙ (This is the part that bonds with carbon.) 【Chemical B-3-21】 (Among the above chemical formula group B-3-21, The hydrogen atoms in each aromatic ring are halogens, cyano groups, C1-C30 alkyl groups, C1-C30 alkoxy groups, C1-C30 haloalkyl groups, and -SiH. ３ It can be substituted with an alkylsilyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. X ａ and X ｂ These are O, S, Se, Te, and NR, respectively, independently. ａ , SiR ｂ R ｃ , and GeR ｄ R ｅ Selected from (where R ａ , R ｂ , R ｃ , R ｄ , and R ｅ Each of these is independently selected from hydrogen, halogen, cyano group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C6-C30 aryloxy group. The asterisk inside the aromatic ring represents CR. ｘｘ -CR ｙｙ (This is the part that bonds with carbon.)

9. It is a near-infrared absorbing material, It contains the compound represented by the chemical formula 1 shown below, In the above chemical formula 1, Ar １ and Ar ２ A near-infrared absorbing material characterized by being identical or different, and selected from the following chemical formulas C-5-1 to C-5-8. 【Chemistry 1】 (In the above chemical formula 1, Ar is a benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetracene ring, or a substituted or unsubstituted pyrene ring. X １ is S, Se, Te, S(=O), or S(=O) ２ And, X ２ are O, S, Se, Te, CR ｘ -CR ｙ CR ｘｘ -CR ｙｙ , or S (=O) (where R ｘ and R ｙ Each of these is independently hydrogen, deuterium, a C1-C30 alkyl group, a C1-C30 haloalkyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C3-C30 heteroaryl group, a halogen, a cyano group, or a combination thereof. ｘｘ and R ｙｙ (These are linked to each other to form an aromatic ring or heteroaromatic ring.) Ar ３ and Ar ４ Each of these is independently a substituted or unsubstituted arene with 6 to 30 carbon atoms, a substituted or unsubstituted heteroarene with 3 to 30 carbon atoms, or a condensed ring thereof. R １ and R ２ Each of these is independently hydrogen, deuterium, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C1-C10 alkoxy group, substituted or unsubstituted C6-C10 aryl group, or substituted or unsubstituted C3-C10 heteroaryl group. L １ and L ２ It is a single bond, 【Chemistry C-5-1】 【Chemistry C-5-2】 【Chemistry C-5-3】 【Chemistry C-5-4】 【Chemistry C-5-5】 【Chemistry C-5-6】 【Chemistry C-5-7】 【Chemical C-5-8】 (Among the chemical formulas C-5-1 to C-5-8 mentioned above, The hydrogen atoms in each aromatic ring are halogens, cyano groups, C1-C30 alkyl groups, C1-C30 alkoxy groups, C1-C30 haloalkyl groups, and -SiH. ３ It can be substituted with an alkylsilyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. Y １ are O, S, Se, Te, S(=O), S(=O) ２ , NR ａ１ , SiR ｂ１ R ｃ１ , or GeR ｄ１ R ｅ１ (where R ａ１ , R ｂ１ , R ｃ１ , R ｄ１ , and R ｅ１ These are, independently, hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, and -SiH ３ , alkylsilyl group having 1 to 10 carbon atoms, -NH ３ (These include alkylamine groups having 1 to 10 carbon atoms, arylamine groups having 6 to 10 carbon atoms, aryl groups having 6 to 14 carbon atoms, aryloxy groups having 6 to 14 carbon atoms, heteroaryl groups having 3 to 12 carbon atoms, halogens, cyano groups, or combinations thereof.) Y ２ and Y ３ These are O, S, Se, Te, S (=O), S (=O) respectively, independently. ２ , NR ａ２ , SiR ｂ２ R ｃ２ , GeR ｄ２ R ｅ２ , or CR ｆ２ R ｇ２ (where R ａ２ , R ｂ２ , R ｃ２ , R ｄ２ , R ｅ２ , R ｆ２ , and R ｇ２ These are, independently, hydrogen, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, and -SiH ３ , alkylsilyl group having 1 to 10 carbon atoms, -NH ３ (These include alkylamine groups having 1 to 10 carbon atoms, arylamine groups having 6 to 10 carbon atoms, aryl groups having 6 to 14 carbon atoms, aryloxy groups having 6 to 14 carbon atoms, heteroaryl groups having 3 to 12 carbon atoms, halogens, cyano groups, or combinations thereof.) R ｂ１ and R ｃ１ , R ｄ１ and R ｅ１ , R ｂ２ and R ｃ２ , R ｄ２ and R ｅ２ , and R ｆ２ and R ｇ２ These elements either exist independently or combine with each other to form a spiro ring. * located outside at least one aromatic ring is a linking site with Ar in chemical formula 1, and * located inside at least one aromatic ring is R in chemical formula 1. １ N(R) １ ) - Containing ring, and R ２ N(R) of chemical formula 1, which includes ２ ) - This is the connection point with the containing ring.

10. It is a near-infrared absorbing material, A near-infrared absorbing material characterized by containing compounds represented by the following chemical formulas 1-1 to 1-9. 【Chemistry 1-1】 【Chemistry 1-2】 [Chemistry 1-3] [Chemistry 1-4] [Chemistry 1-5] [Chemistry 1-6] [Chemistry 1-7] [Chemistry 1-8] [Chemistry 1-9]

11. The near-infrared absorbing material according to claim 1, characterized in that the peak absorption wavelength of the near-infrared absorbing material belongs to the wavelength range of 750 nm to 3000 nm.

12. A near-infrared absorbing / blocking film characterized by containing a near-infrared absorbing material according to any one of claims 1 to 10.

13. A photoelectric element, The first electrode and the second electrode are facing each other, It comprises an active layer disposed between the first electrode and the second electrode, The photoelectric element is characterized in that the active layer includes a near-infrared absorbing material according to any one of claims 1 to 10.

14. The photoelectric element according to claim 13, characterized in that the active layer further comprises a fullerene or a fullerene derivative.

15. The photoelectric element according to claim 13, characterized in that the peak absorption wavelength of the active layer belongs to the wavelength range of 750 nm to 3000 nm.

16. The first electrode and the second electrode are facing each other, An active layer disposed between the first electrode and the second electrode, The device has at least one charge auxiliary layer between the active layer and the first electrode or between the active layer and the second electrode, The photoelectric element is characterized in that the charge auxiliary layer includes an infrared absorbing material according to any one of claims 1 to 10.

17. The photoelectric element according to claim 16, characterized in that the active layer further comprises the near-infrared absorbing material.

18. It is an organic sensor, An organic sensor characterized by including a photoelectric element according to any one of claims 13 to 17.

19. Semiconductor substrate and A first photoelectric element present on the semiconductor substrate selectively absorbs light in the first near-infrared wavelength region, The system includes an additional sensor that selectively absorbs light in a separate wavelength region different from the first near-infrared wavelength region, The first photoelectric element is characterized by containing a near-infrared absorbing material according to any one of claims 1 to 10.

20. The additional sensor is an infrared sensor at least partially embedded in a semiconductor substrate, and the separate wavelength region is a separate near-infrared wavelength region different from the first near-infrared wavelength region. The organic sensor according to claim 19, characterized in that the first photoelectric element and the infrared sensor are superimposed in a direction perpendicular to the upper surface of the semiconductor substrate.

21. The additional sensor includes a plurality of photodiodes at least partially embedded within a semiconductor substrate, wherein the plurality of photodiodes are configured to selectively absorb light in separate visible light wavelength regions. The organic sensor according to claim 19, characterized in that the first photoelectric element and the plurality of photodiodes overlap in a direction perpendicular to the upper surface of the semiconductor substrate.

22. The organic sensor further includes additional photoelectric elements on a semiconductor substrate, The organic sensor according to claim 21, wherein the additional photoelectric element is located between the first photoelectric element and the semiconductor substrate, and the additional photoelectric element is configured to selectively absorb light in an additional wavelength region different from the first near-infrared wavelength region and the separate visible light wavelength region.

23. The above additional sensor includes at least one additional photoelectric element stacked vertically between the first photoelectric element and the semiconductor substrate. The organic sensor according to claim 19, characterized in that each of the additional photoelectric elements comprises a separate photoelectric conversion layer and is configured to selectively absorb light in each respective wavelength region different from the first near-infrared wavelength region.

24. The organic sensor according to claim 19, wherein the first photoelectric element includes a first electrode and a second electrode facing each other, and an active layer between the first electrode and the second electrode, the active layer comprising a near-infrared absorbing material.

25. The organic sensor according to claim 19, wherein the first photoelectric element includes a first electrode and a second electrode facing each other, an active layer between the first electrode and the second electrode, and at least one charge auxiliary layer between the active layer and the first electrode, or between the active layer and the second electrode, wherein the charge auxiliary layer includes the near-infrared absorbing material.

26. An electronic device characterized by including an organic sensor according to any one of claims 18 to 25.

27. An electronic device characterized by including a photoelectric element according to any one of claims 13 to 17.

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