Near-infrared absorber, near-infrared absorption / blocking film, optoelectronic device, organic sensor, and electronic device

Abstract

Near-infrared absorbers, near-infrared absorption / blocking films, optoelectronic devices, organic sensors, and electronic devices are disclosed. The near-infrared absorber includes a compound represented by Chemical Formula 1, and the near-infrared absorption / blocking film, optoelectronic device, organic sensor, and electronic device may include the near-infrared absorber. In Chemical Formula 1, X 1 , X 2 , Y 1 , Y 2 , Ar, Ar 1 , and Ar 2 are the same as defined in the detailed description. [Chemical Formula 1]

Description

[0001] Cross - reference to related applications

[0002] This application claims the priority and benefit of Korean Patent Application No. 10 - 2019 - 0113716, filed with the Korean Intellectual Property Office on September 16, 2019, the entire content of which is incorporated herein by reference. Technical field

[0003] Near - infrared (NIR) absorbers, near - infrared absorption / blocking films, optoelectronic devices, organic sensors, and electronic devices are disclosed. Background art

[0004] Imaging devices are used in digital cameras and camcorders, etc. to capture images and store them as electrical signals, and the imaging device includes a sensor that separates incident light according to wavelength and converts each component into an electrical signal.

[0005] Recently, optoelectronic devices in the near - infrared region have been studied to improve the sensitivity of sensors in low - light environments or to be used as biometric devices. Summary of the invention

[0006] Some example embodiments provide a near - infrared absorber having improved near - infrared light absorption characteristics.

[0007] Some example embodiments provide a film including the near - infrared absorber.

[0008] Some example embodiments provide an optoelectronic device including the near - infrared absorber.

[0009] Some example embodiments provide an organic sensor including the near - infrared absorber or the optoelectronic device.

[0010] Some example embodiments provide an electronic device including the optoelectronic device or the organic sensor.

[0011] According to some example embodiments, there is provided a near - infrared absorber including a compound represented by Chemical Formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] Ar may be a substituted or unsubstituted C6 - C30 aromatic ring, a substituted or unsubstituted C3 - C30 heteroaromatic ring, or a combination thereof,

[0016] X 1 may be O, S, Se, Te, S(=O), S(=O2), NRa , C(=O), CR b R c or SiR d R e , where R a , R b , R c , R d and R e are independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, halogen or cyano,

[0017] X 2 can be O, S, Se, Te, C, S(=O) or S(=O2),

[0018] Y 1 and Y 2 can independently be O, S, Se, Te, S(=O), S(=O)2, NR a , SiR b R c or CR d R e , where R a , R b , R c , R d and R e are independently hydrogen, deuterium, C1-C6 alkyl, C1-C6 haloalkyl, halogen or cyano, and

[0019] Ar 1 and Ar 2 are independently a functional group represented by Chemical Formula A.

[0020] [Chemical Formula A]

[0021]

[0022] In Chemical Formula A,

[0023] Ar 3 and Ar 4 can independently be a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group,

[0024] G can be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h)=C(R i ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R i can independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C10 alkyl, or a substituted or unsubstituted C6-C10 aryl, where R b and R c , R d and R e , R f and R g , or R h and R i can independently exist or be connected to each other to form a ring, and -(CR f R g ) n - has n as an integer of 1 or 2, and

[0025] * can be a connection point.

[0026] In Chemical Formula 1, Ar can be an unsubstituted 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.

[0027] In Chemical Formula 1, Ar can 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.

[0028] Chemical Formula A can be represented by one of Chemical Formulas A-1 to A-5.

[0029] [Chemical Formula A-1]

[0030]

[0031] In Chemical Formula A-1,

[0032] G can be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h )=C(Ri ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R i can independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 - C10 alkyl group, or a substituted or unsubstituted C6 - C10 aryl group, where R b and R c , R d and R e , R f and R g , or R h and R i can independently exist or be connected to each other to form a ring, and -(CR f R g ) n - has an n that is an integer of 1 or 2, and

[0033] R 4a to R 4d and R 5a to R 5d can have the following structure: such that R 4a to R 4d and R 5a to R 5d can 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 halogen, a cyano group (-CN), a cyano - containing group, or a combination thereof, or 4a to R 4d of two adjacent groups can be connected to each other to provide a 5 - membered aromatic ring or a 6 - membered aromatic ring, and / or 5a to R 5d of two adjacent groups can be connected to each other to provide a 5 - membered aromatic ring or a 6 - membered aromatic ring.

[0034] [Chemical formula A - 2]

[0035]

[0036] In Chemical formula A - 2,

[0037] G can be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CRf R g ) n - or -(C(R h ))=C(R i ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R i may independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 - C10 alkyl, or a substituted or unsubstituted C6 - C10 aryl, where R b and R c , R d and R e , R f and R g , or R h and R i may independently exist or be connected to each other to form a ring, and the n of -(CR f R g ) n - is an integer of 1 or 2, and

[0038] R 4a to R 4d and R 5b to R 5d may have the following structure: such that R 4a to R 4d and R 5b to R 5d may independently be hydrogen, deuterium, a substituted or unsubstituted C1 - C30 alkyl, a substituted or unsubstituted C6 - C30 aryl, a substituted or unsubstituted C3 - C30 heteroaryl, a halogen, cyano (-CN), a cyano - containing group or a combination thereof, or two adjacent groups of R 4a to R 4d may be connected to each other to provide a 5 - membered aromatic ring or a 6 - membered aromatic ring, and / or two adjacent groups of R 5b to R 5d may be connected to each other to provide a 5 - membered aromatic ring or a 6 - membered aromatic ring.

[0039] [Chemical formula A - 3]

[0040]

[0041] In Chemical formula A - 3,

[0042] G may be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiRb R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h )=C(R i ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R i can independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C10 aryl group, where R b and R c , R d and R e , R f and R g , or R h and R i can independently exist or be connected to each other to form a ring, and -(CR f R g ) n - has an n that is an integer of 1 or 2, and

[0043] R 4b to R 4d and R 5b to R 5d can have the following structure: such that R 4b to R 4d and R 5b to R 5d can 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 halogen, a cyano group (-CN), a cyano group-containing group, or a combination thereof, or 4b to R 4d two adjacent groups can be connected to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, and / or 5b to R 5d two adjacent groups can be connected to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

[0044] [Chemical Formula A-4]

[0045]

[0046] In Chemical Formula A-4,

[0047] G can be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h )=C(R i ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R i can independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, where R b and R c , R d and R e , R f and R g , or R h and R i can independently exist or be connected to each other to form a ring, and n of -(CR f R g ) n - is an integer of 1 or 2, and

[0048] R 4a to R 4d and R 5b and R 5d can have the following structure: such that R 4a to R 4d and R 5b and R 5d are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group (-CN), a cyano-containing group or a combination thereof, or two adjacent groups of R 4a to R 4d can be connected to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

[0049] [Chemical formula A-5]

[0050]

[0051] In chemical formula A-5,

[0052] G can be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h ))=C(R i ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R i can independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C10 aryl group, where R b and R c , R d and R e , R f and R g , or R h and R i can independently exist or be connected to each other to form a ring, and -(CR f R g ) n - has an n of 1 or 2, and

[0053] R 4a to R 4d and R 5b and R 5c can have the following structures: such that R 4a to R 4d and R 5b to R 5c can 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 halogen, a cyano group (-CN), a cyano-containing group or a combination thereof, or 4a to R 4d of two adjacent groups can be connected to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, and / or 5b and R 5c of two adjacent groups can be connected to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

[0054] The near-infrared absorber may have a peak absorption wavelength in a wavelength region of from about 700 nm to about 3000 nm.

[0055] According to some example embodiments, a near-infrared absorption / blocking film including the near-infrared absorber is provided.

[0056] According to some example embodiments, an optoelectronic device includes a first electrode and a second electrode facing each other, and an active layer (active layer) disposed between the first electrode and the second electrode, wherein the active layer includes the near-infrared absorber including the compound represented by Chemical Formula 1.

[0057] According to some example embodiments, an organic sensor including the optoelectronic device is provided.

[0058] According to some example embodiments, an electronic device including the optoelectronic device or the organic sensor is provided.

[0059] The near-infrared absorber may exhibit light absorption characteristics in the near-infrared region and thus may be effectively used in optoelectronic devices and / or organic sensors. BRIEF DESCRIPTION OF THE DRAWINGS

[0060] Figure 1 A cross-sectional view showing an optoelectronic device according to some embodiments,

[0061] Figure 2 A cross-sectional view showing an optoelectronic device according to some embodiments,

[0062] Figure 3 A cross-sectional view showing an organic sensor according to some embodiments,

[0063] Figure 4 A cross-sectional view showing an organic sensor according to some embodiments,

[0064] Figure 5 A cross-sectional view showing an organic sensor according to some embodiments,

[0065] Figure 6 A block diagram of a digital camera including an organic sensor according to some embodiments, and

[0066] Figure 7 A graph showing the external quantum efficiency of an optoelectronic device according to Example 5. DETAILED DESCRIPTION

[0067] Hereinafter, some example embodiments will be described in detail below and can be easily implemented by those of ordinary skill in the relevant art. However, the present disclosure may be embodied in many different forms and is not to be construed as limited to the example embodiments set forth herein.

[0068] In the drawings, for clarity, the thicknesses of layers, films, panels, regions, etc. are enlarged.

[0069] It will be understood that when an element such as a layer, film, region, or substrate is referred to as being "on" another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being "directly on" another element, no intervening elements are present. It will be further understood that when an element is referred to as being "on" another element, it can be above or below the other element.

[0070] It will be understood that an element and / or its properties may be described herein as being "the same" or "equivalent" to other elements, and it will be further understood that elements and / or their properties described herein as being "the same" or "equivalent" to other elements may be "the same" or "equivalent" or "substantially the same" or "substantially equivalent" to other elements and / or their properties. Elements and / or their properties that are "substantially the same" or "substantially equivalent" to other elements and / or their properties will be understood to include elements and / or their properties that are the same or equivalent to other elements and / or their properties within manufacturing tolerances and / or material tolerances. Elements and / or their properties that are the same or substantially the same as other elements and / or their properties may be the same or substantially the same structurally, the same or substantially the same functionally, and / or the same or substantially the same compositionally.

[0071] It will be understood that elements and / or their properties described herein as being "substantially" the same encompass elements and / or their properties having a relative difference in magnitude of equal to or less than 10%. Further, whether or not elements and / or their properties are modified as "substantially", it will be understood that these elements and / or their properties should be interpreted to include manufacturing or operating tolerances (e.g., ±10%) around the stated elements and / or their properties.

[0072] When the terms "about" or "substantially" are used in connection with a numerical value in this specification, it is intended that the associated numerical value include a tolerance of ±10% around the stated numerical value. When a range is recited, the range includes all values therebetween, e.g., increments of 0.1%.

[0073] In the drawings, for clarity of the embodiments, parts not relevant to the description are omitted, and throughout the specification, the same or similar components are denoted by the same reference numerals.

[0074] As used herein, "at least one of A, B, or C", "one of A, B, C, or a combination thereof", and "one of A, B, C and their combinations" refer to each of the constituent elements and their combinations (e.g., A; B; C; A and B; A and C; B and C; or A, B, and C).

[0075] As used herein, unless otherwise specifically defined, "substituted" means that the hydrogen of a compound or functional group is replaced with: a halogen atom, a hydroxyl group, an alkoxy group, a nitro group, a cyano group, an amino group, an azide group, an amidino group, a hydrazino group, a hydrazo group, a carbonyl group, a carbamoyl group, a mercapto group, an ester group, a carboxyl group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a silyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C30 aryl group, a C7-C30 aralkyl group, a C1-C30 alkoxy group, a C1-C20 heteroalkyl group, a C3-C20 heteroaryl group, a C3-C20 heteroaralkyl group, a C3-C30 cycloalkyl group, a C3-C15 cycloalkenyl group, a C6-C15 cycloalkynyl group, a C3-C30 heterocycloalkyl group, or a combination thereof.

[0076] As used herein, unless otherwise specifically defined, "hetero" means including 1-4 heteroatoms selected from N, O, S, Se, Te, Si, and P.

[0077] As used herein, unless otherwise defined, "aromatic ring" refers to a functional group as follows: all atoms in the cyclic functional group have p-orbitals, and these p-orbitals are conjugated, and "heteroaromatic ring" refers to an aromatic ring including heteroatoms. "Aromatic ring" refers to a C6-C30 arene group, such as a C6-C20 arene group or a C6-C30 aryl group, such as a C6-C20 aryl group. Additionally, "heteroaromatic ring" may be a C3-C30 heteroarene group, for example, a C3-C20 heteroarene group, or a C3-C30 heteroaryl group, for example, a C3-C20 heteroaryl group.

[0078] As used herein, "arene group" refers to a hydrocarbon group having an aromatic ring, and includes monocyclic and polycyclic hydrocarbon groups, and the additional rings of the polycyclic hydrocarbon groups may be aromatic rings or non-aromatic rings. "Heteroarene group" refers to an arene group including 1 to 3 heteroatoms selected from N, O, S, P, and Si.

[0079] As used herein, unless otherwise defined, "aryl" refers to a group including at least one hydrocarbon aromatic moiety, and may include: a group in which all elements of the hydrocarbon aromatic moiety have p-orbitals forming conjugation, such as phenyl, naphthyl, etc.; a group in which two or more hydrocarbon aromatic moieties may be connected by a σ bond, such as biphenyl, terphenyl, quaterphenyl, etc.; and a group in which two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl. Aryl may include monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional groups.

[0080] As used herein, when no other definition is provided, "heteroaryl" refers to an aryl group that includes at least one heteroatom selected from N, O, S, Se, Te, P, and Si in the ring in place of carbon (C). When the heteroaryl is a fused ring, at least one ring of the heteroaryl may have a heteroatom or each ring may have a heteroatom.

[0081] As used herein, when no other definition is provided, "ring" refers to an aromatic ring, a non-aromatic ring, a heteroaromatic ring, a hetero non-aromatic ring, its fused rings, and / or their combination.

[0082] As used herein, when no other definition is provided, "cyano-containing group" refers to a monovalent group in which at least one hydrogen is replaced by a cyano group, such as a C1-C30 alkyl group, a C2-C30 alkenyl group, or a C2-C30 alkynyl group. The cyano-containing group also refers to a divalent group such as =CR x '-(CR x R y ) p -CR y '(CN)2, where R x 、R y 、R x ' and R y ' are each independently hydrogen or a C1-C10 alkyl group, and p is an integer from 0 to 10 (or 1 to 10). Specific examples of the cyano-containing group may be dicyanomethyl, dicyanovinyl, cyanoethynyl, etc. As used herein, the cyano-containing group does not include a functional group that only includes a cyano group (-CN).

[0083] Hereinafter, near-infrared absorbers according to some embodiments are described. The near-infrared absorber may be interchangeably referred to as a "near-infrared absorbing compound" herein.

[0084] The near-infrared absorber includes a compound represented by Chemical Formula 1.

[0085] [Chemical Formula 1]

[0086]

[0087] In Chemical Formula 1,

[0088] Ar may be a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, or a combination thereof,

[0089] X 1 may be O, S, Se, Te, S(=O), S(=O2), NR a 、C(=O), CR b R c or SiR d R e (where Ra , R b , R c , R d and R e may independently be hydrogen, deuterium, C1-C6 alkyl, C1-C6 haloalkyl, halogen or cyano),

[0090] X 2 may be O, S, Se, Te, C, S(=O) or S(=O2),

[0091] Y 1 and Y 2 may independently be O, S, Se, Te, S(=O), S(=O)2, NR a , SiR b R c or CR d R e (wherein R a , R b , R c , R d and R e may independently be hydrogen, deuterium, C1-C6 alkyl, C1-C6 haloalkyl, halogen or cyano), and

[0092] Ar 1 and Ar 2 may independently be a functional group represented by Chemical Formula A.

[0093] [Chemical Formula A]

[0094]

[0095] In Chemical Formula A,

[0096] Ar 3 and Ar 4 may independently be a substituted or unsubstituted C6-C30 aryl group, such as a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, such as a substituted or unsubstituted C3-C20 heteroaryl group,

[0097] G may be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a (-), -SiR b R c (-), -GeR d R e (-), -(CR f R g ) n (- or -(C(R h ))=C(R i ))-(wherein R a, R b , R c , R d , R e , R f , R g , R h and R i may independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C10 aryl group, where R b and R c , R d and R e , R f and R g , or R h and R i may independently be present or connected to each other to form a ring, and -(CR f R g ) n - has n as an integer of 1 or 2), and

[0098] * may be a connection point.

[0099] The near-infrared absorber has a donor-acceptor-donor structure, in which a substituted or unsubstituted cyclic amine group (chemical formula A) having an electron-donating property is connected to a ring containing Y 1 and a ring containing Y 2 to a nucleus having a conjugated structure with an electron-accepting property, and thus may have improved light absorption characteristics to effectively absorb light in the near-infrared wavelength region, and may exhibit good electrical properties.

[0100] The near-infrared absorber may have a peak absorption wavelength (λ 最大 ) of, for example, greater than or equal to about 700 nm, such as greater than or equal to about 750 nm, greater than or equal to about 780 nm, greater than or equal to about 790 nm, greater than or equal to about 800 nm, greater than or equal to about 810 nm, greater than or equal to about 820 nm, or greater than or equal to about 830 nm. The near-infrared absorber may have a peak absorption wavelength (λ 最大 ) of, for example, about 700 nm to about 3000 nm, about 750 nm to about 2500 nm, about 780 nm to about 2200 nm, about 790 nm to about 2100 nm, about 800 nm to about 2000 nm, about 810 nm to about 2000 nm, about 820 nm to about 2000 nm, or about 830 nm to about 2000 nm.

[0101] In Chemical Formula 1, X 1 and X 2 may be the same as or different from each other.

[0102] In Chemical Formula 1, X1 and X 2 may independently be O or S.

[0103] In Chemical Formula 1, Y 1 and Y 2 may be the same as or different from each other.

[0104] In Chemical Formula 1, Y 1 and Y 2 may independently be O, S or C(CN)2.

[0105] In Chemical Formula 1, Ar may be an unsubstituted 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.

[0106] 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.

[0107] The ring containing Y 1 and the ring containing Y 2 may be connected at symmetric positions relative to Ar or at asymmetric positions relative to Ar.

[0108] In Chemical Formula 1, Ar may be a part of a group of parts represented by Chemical Formula B-1, each part including at least one aromatic ring and left and right linking groups.

[0109] [Chemical Formula B-1]

[0110]

[0111] In Chemical Formula B-1, the hydrogen of each aromatic ring may be replaced by a halogen, a cyano group, a C1-C10 alkyl group or a C1-C10 haloalkyl group, adjacent pairs of the single * in at least one aromatic ring are each a part fused with the pentagonal ring containing N-X 1 -N- of Chemical Formula 1 and the pentagonal ring containing N=X 2 =N of Chemical Formula 1, and the * of the left and right linking groups is the connecting part of the ring containing Y 1 and the ring containing Y 2 of Chemical Formula 1.

[0112] In Chemical Formula 1, Ar may be a part of a group of parts represented by Chemical Formula B-2, each part including at least one aromatic ring and left and right linking groups.

[0113] [Chemical Formula B-2]

[0114]

[0115] In Chemical Formula B-2, the hydrogen of each aromatic ring may be replaced by a halogen, a cyano group, a C1 to C10 alkyl group or a C1 to C10 haloalkyl group, and adjacent pairs of the individual * in at least one aromatic ring are with the N-X-containing of Chemical Formula 1 1 -N- pentagonal ring and the N=X-containing of Chemical Formula 1 2 =N pentagonal ring of a single corresponding fused portion, and the * of the left and right linking groups is the Y-containing of Chemical Formula 1 1 ring and the connecting portion of the Y-containing ring 2 ring.

[0116] In Chemical Formula 1, the Y-containing ring and the Y-containing ring may be represented by Chemical Formula C. 1 ring and the Y-containing ring 2 ring may be represented by Chemical Formula C.

[0117] [Chemical Formula C]

[0118]

[0119] In Chemical Formula C,

[0120] R a to R e may independently be hydrogen, deuterium, a C1 to C6 alkyl group, a halogen, a cyano group or a combination thereof.

[0121] Chemical Formula A may be represented by one of Chemical Formulas A-1 to A-5.

[0122] [Chemical Formula A-1]

[0123]

[0124] In Chemical Formula A-1,

[0125] G may be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h ))=C(R i ))- (wherein R a , R b , R c , R d , R e , R f , R g , R h and R imay independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, where R b and R c 、R d and R e 、R f and R g 、or R h and R i may independently exist or be linked to each other to form a ring, and -(CR f R g ) n - has an n that is an integer of 1 or 2), and

[0126] R 4a to R 4d and R 5a to R 5d may have the following structure: such that a) R 4a to R 4d and R 5a to R 5d may independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group (-CN), a cyano-containing group, or a combination thereof, or b) optionally, two adjacent groups of R 4a to R 4d may be linked to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, and optionally, two adjacent groups of R 5a to R 5d may be linked to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

[0127] [Chemical Formula A-2]

[0128]

[0129] In Chemical Formula A-2,

[0130] G may be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h )=C(R i ))-(where R a 、R b 、R c 、R d 、Re , R f , R g , R h and R i may each independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 - C10 alkyl, or a substituted or unsubstituted C6 - C10 aryl, where R b and R c , R d and R e , R f and R g , or R h and R i may each independently be present or linked to each other to form a ring, and -(CR f R g )) n - has n as an integer of 1 or 2), and

[0131] R 4a to R 4d and R 5b to R 5d may have the following structure: such that a) R 4a to R 4d and R 5b to R 5d may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 - C30 alkyl, a substituted or unsubstituted C6 - C30 aryl, a substituted or unsubstituted C3 - C30 heteroaryl, a halogen, cyano (-CN), a cyano - containing group or a combination thereof, or b) optionally, two adjacent groups of R 4a to R 4d may be linked to each other to provide a 5 - membered aromatic ring or a 6 - membered aromatic ring, and optionally, two adjacent groups of R 5b to R 5d may be linked to each other to provide a 5 - membered aromatic ring or a 6 - membered aromatic ring.

[0132] [Chemical formula A - 3]

[0133]

[0134] In Chemical formula A - 3,

[0135] G may be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g )) n - or -(C(R h ))=C(Ri )) - (where R a , R b , R c , R d , R e , R f , R g , R h and R i may independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 - C10 alkyl group, or a substituted or unsubstituted C6 - C10 aryl group, where R b and R c , R d and R e , R f and R g , or R h and R i may independently exist or be connected to each other to form a ring, and -(CR f R g ) n - has n as an integer of 1 or 2), and

[0136] R 4b to R 4d and R 5b to R 5d may have the following structures: such that a) R 4b to R 4d and R 5b to R 5d 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 halogen, a cyano group (-CN), a cyano - containing group or a combination thereof, or b) optionally, two adjacent groups of R 4b to R 4d may be connected to each other to provide a 5 - membered aromatic ring or a 6 - membered aromatic ring, and optionally, two adjacent groups of R 5b to R 5d may be connected to each other to provide a 5 - membered aromatic ring or a 6 - membered aromatic ring.

[0137] [Chemical formula A - 4]

[0138]

[0139] In chemical formula A - 4,

[0140] G may be a single bond, -O -, -S -, -Se -, -Te -, -N =, -NR a -, -SiR b R c -, -GeR d R e-, -(CR f R g ) n - or -(C(R h )=C(R i ))-(where R a , R b , R c , R d , R e , R f , R g , R h and R i may independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 - C10 alkyl, or a substituted or unsubstituted C6 - C10 aryl, where R b and R c , R d and R e , R f and R g , or R h and R i may independently exist or be connected to each other to form a ring, and -(CR f R g ) n - has an integer n of 1 or 2), and

[0141] R 4a to R 4d and R 5b and R 5d may have the following structure: such that a) R 4a to R 4d and R 5b and R 5d may independently be hydrogen, deuterium, a substituted or unsubstituted C1 - C30 alkyl, a substituted or unsubstituted C6 - C30 aryl, a substituted or unsubstituted C3 - C30 heteroaryl, a halogen, a cyano group (-CN), a cyano - containing group or a combination thereof, or b) optionally, two adjacent groups of R 4a to R 4d may be connected to each other to provide a 5 - membered aromatic ring or a 6 - membered aromatic ring.

[0142] [Chemical Formula A - 5]

[0143]

[0144] In Chemical Formula A - 5,

[0145] G may be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d Re -, -(CR f R g ) n - or -(C(R h ))=C(R i ))-(wherein R a , R b , R c , R d , R e , R f , R g , R h , and R i may independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C10 aryl group, wherein R b and R c , R d and R e , R f and R g , or R h and R i may independently exist or be connected to each other to form a ring, and -(CR f R g ) n - has an integer n of 1 or 2), and

[0146] R 4a to R 4d and R 5b and R 5c may have the following structure: such that a) R 4a to R 4d and R 5b to R 5c 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 halogen, a cyano group (-CN), a cyano-containing group or a combination thereof, or b) optionally, two adjacent groups of R 4a to R 4d may be connected to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, and optionally, two adjacent groups of R 5b and R 5c may be connected to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

[0147] The near-infrared absorber may exhibit good charge transfer characteristics, and thus, it has good photoelectric conversion characteristics of absorbing light and converting it into an electrical signal, and thus can be effectively used as a photoelectric conversion material for optoelectronic devices.

[0148] The near-infrared absorber has good heat resistance, and thus can prevent or reduce thermal decomposition during deposition, and can thus be deposited repeatedly. The near-infrared absorber can be thermally deposited or vacuum deposited, and can be deposited, for example, by sublimation. For example, deposition by sublimation can be confirmed by thermogravimetric analysis (TGA), and in thermogravimetric analysis at a pressure less than or equal to about 10 Pa, the temperature at 10% weight loss relative to the initial weight can be less than or equal to about 450 °C, and the temperature at 50% weight loss relative to the initial weight can be less than or equal to about 500 °C. For example, in thermogravimetric analysis of the near-infrared absorber at a pressure less than or equal to about 10 Pa, the temperature at 10% weight loss relative to the initial weight can be, for example, about 230 °C to about 450 °C, and the temperature at 50% weight loss relative to the initial weight can be about 300 °C to about 500 °C.

[0149] Some example embodiments provide a near-infrared absorption / blocking film (near-infrared absorption and blocking film) including the near-infrared absorber.

[0150] The near-infrared absorption / blocking film can be applied to various fields that require light absorption characteristics in the near-infrared wavelength region.

[0151] The near-infrared absorber has both light absorption characteristics and optoelectronic characteristics in the near-infrared wavelength region, and it can be effectively used as an optoelectronic conversion material.

[0152] Figure 1 is a cross-sectional view of an optoelectronic device according to some example embodiments.

[0153] Reference Figure 1 , an optoelectronic device 100 according to some example embodiments includes a first electrode 10 and a second electrode 20 facing each other and an active layer 30 between the first electrode 10 and the second electrode 20.

[0154] A substrate (not shown) may be provided on one side of the first electrode 10 or the second electrode 20. The substrate can be made of, for example, (e.g., can at least partially include the following): inorganic materials such as glass; organic materials such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, polyethersulfone, or a combination thereof; or a silicon wafer. The substrate can be omitted.

[0155] One of the first electrode 10 and the second electrode 20 is an anode, and the other is a cathode. For example, the first electrode 10 can be a cathode, and the second electrode 20 can be an anode.

[0156] At least one of the first electrode 10 or the second electrode 20 may be a light-transmissive electrode, and the light-transmissive electrode may be made of, for example, a conductive oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO2), aluminum tin oxide (AlTO), and fluorine-doped tin oxide (FTO), or a thin metal layer of a single layer or multiple layers. When one of the first electrode 10 or the second electrode 20 is a non-light-transmissive electrode, it may be made of, for example, an opaque conductor such as aluminum (Al), silver (Ag), or gold (Au). For example, both the first electrode 10 and the second electrode 20 may be light-transmissive electrodes. For example, the second electrode 20 may be a light-receiving electrode provided on the light-receiving side.

[0157] The active layer is a layer including a p-type semiconductor and an n-type semiconductor to provide a pn junction, which is a layer that generates excitons by receiving light from the outside and then separates holes and electrons from the generated excitons.

[0158] The p-type semiconductor and the n-type semiconductor may independently be light absorbers configured to absorb (e.g., selectively absorb) light in at least a part of a wavelength region, and the aforementioned near-infrared absorber may be a p-type semiconductor or an n-type semiconductor. For example, the aforementioned near-infrared absorber may be used for the p-type semiconductor, and may include fullerenes or fullerene derivatives as the n-type semiconductor. Thus, it will be understood that the active layer 30 may at least partially include the aforementioned near-infrared absorber (e.g., may include a near-infrared absorber and fullerenes or fullerene derivatives). The active layer 30 and thus the optoelectronic device 100 may have improved near-infrared light absorption characteristics (e.g., may have improved sensitivity to light in the near-infrared wavelength region, improved light absorption rate in the near-infrared wavelength region, etc.) and thus improved optoelectronic conversion performance and / or efficiency based on the active layer including the aforementioned near-infrared absorber. In some example embodiments, the active layer 30 may be a near-infrared absorption / blocking film including the aforementioned near-infrared absorber.

[0159] The active layer 30 may include an intrinsic layer (I layer) in which the aforementioned near-infrared absorber (p-type semiconductor) and fullerenes or fullerene derivatives (n-type semiconductor) are co-deposited. Here, the p-type semiconductor and the n-type semiconductor may be included in a volume ratio of about 1:9 to about 9:1, for example, about 2:8 to about 8:2, about 3:7 to about 7:3, about 4:6 to about 6:4, or about 5:5.

[0160] In addition to the intrinsic layer, the active layer 30 may further include a p-type layer and / or an n-type layer. The p-type layer may include the aforementioned near-infrared absorber, and the n-type layer may include the aforementioned n-type semiconductor. For example, they may be included in various combinations such as a p-type layer / I layer, an I layer / n-type layer, a p-type layer / I layer / n-type layer, etc.

[0161] The optoelectronic device 100 may further include an auxiliary layer between the first electrode 10 and the active layer 30 and / or between the second electrode 20 and the active layer 30. The optoelectronic device (e.g., optoelectronic device) is shown in Figure 2 in.

[0162] Figure 2 is a cross-sectional view showing an optoelectronic device according to some example embodiments.

[0163] Referring to Figure 2 , the optoelectronic device 200 includes a first electrode 10 and a second electrode 20 facing each other, an active layer 30 between the first electrode 10 and the second electrode 20, a first auxiliary layer 40 between the first electrode 10 and the active layer 30, and a second auxiliary layer 45 between the second electrode 20 and the active layer 30. In some example embodiments, only one of the first auxiliary layer 40 or the second auxiliary layer 45 is included in the optoelectronic device 200. The first auxiliary layer 40 and the second auxiliary layer 45 may each be a charge assisting layer that makes it easier for holes and electrons separated in the active layer 30 to be transported to improve the efficiency of the optoelectronic device 200.

[0164] The charge assisting layer 40 and / or 45 may include at least one selected from the following: a hole injection layer (HIL) for promoting hole injection, a hole transport layer (HTL) for promoting hole transport, an electron blocking layer (EBL) for preventing electron transport, an electron injection layer (EIL) for promoting electron injection, an electron transport layer (ETL) for promoting electron transport, and a hole blocking layer (HBL) for preventing hole transport.

[0165] The charge assisting layers 40 and 45 may include, for example, an organic material, an inorganic material, or an organic / inorganic material. The organic material may be an organic material having hole or electron properties, and the inorganic material may be, for example, a metal oxide such as molybdenum oxide, tungsten oxide, or nickel oxide.

[0166] The charge assisting layer 40 and / or 45 may include, for example, the above-mentioned near-infrared absorber.

[0167] The optoelectronic devices 100 and 200 may further include an antireflection layer (not shown) on one surface of the first electrode 10 or the second electrode 20. The antireflection layer is disposed on the light incident side and reduces the light reflectance of the incident light, and thus, the light absorption rate is further improved. For example, when light enters from the first electrode 10, the antireflection layer may be disposed on the first electrode 10, and when light enters from the second electrode 20, the antireflection layer may be disposed under the second electrode 20.

[0168] The antireflection layer may include, for example, a material having a refractive index of about 1.6 to about 2.5, and may include, for example, at least one of a metal oxide, a metalloid oxide, a metal sulfide, or an organic material having a refractive index within the above range. The antireflection layer may include, for example, a metal oxide or a metalloid oxide such as aluminum-containing oxide, molybdenum-containing oxide, tungsten-containing oxide, vanadium-containing oxide, rhenium-containing oxide, niobium-containing oxide, tantalum-containing oxide, titanium-containing oxide, nickel-containing oxide, copper-containing oxide, cobalt-containing oxide, manganese-containing oxide, chromium-containing oxide, tellurium-containing oxide, or a combination thereof; a metal sulfide such as zinc sulfide; or an organic material such as an amine derivative, but is not limited thereto.

[0169] In optoelectronic devices 100 and 200, when light enters the optoelectronic devices 100 and / or 200 and thus enters their active layer 30 from (e.g., via) the first electrode 10 or the second electrode 20, and the active layer 30 thus absorbs light in a specific (or, alternatively, predetermined) wavelength region, excitons may be generated therein. The excitons are separated into holes and electrons in the active layer 30, and the separated holes are transported to the anode, which is one of the first electrode 10 and the second electrode 20, and the separated electrons are transported to the cathode, which is the other electrode of the first electrode 10 and the second electrode 20, such that a current (e.g., induced, generated, etc.) flows.

[0170] Optoelectronic devices 100 and 200 may be applied to solar cells, image sensors, photodetectors, photosensors, and organic light-emitting diodes (OLEDs), but are not limited thereto.

[0171] Optoelectronic devices 100 and 200 may be applied to organic sensors (e.g., included therein). The organic sensor may be an organic CMOS sensor, such as an organic CMOS infrared light sensor or an organic CMOS image sensor.

[0172] In some example embodiments, optoelectronic device 100 may include the near-infrared absorber in any of its elements (including, in addition to or instead of the active layer 30, one or more of the first electrode 10 or the second electrode 20). In some example embodiments, optoelectronic device 200 may include the near-infrared absorber in any of its elements (including, in addition to or instead of one or more of the active layer 30 and / or the charge assisting layer 40 / 45, one or more of the first electrode 10 or the second electrode 20).

[0173] Figure 3 is a cross-sectional view showing an organic sensor according to some example embodiments.

[0174] According to some example embodiments, the organic sensor 300 includes a semiconductor substrate 110, an insulating layer 80, and an optoelectronic device 100.

[0175] The semiconductor substrate 110 may be a silicon substrate and integrated with a transfer transistor (not shown) and a charge memory 55. The charge memory 55 may be integrated in each pixel. The charge memory 55 is electrically connected to the optoelectronic device 100, and the information of the charge memory 55 may be transmitted by the transfer transistor.

[0176] Metal lines (not shown) and pads (not shown) are formed on the semiconductor substrate 110. To reduce signal delay, the metal lines and pads may be made of a metal having a low resistivity such as aluminum (Al), copper (Cu), silver (Ag), and their alloys, but are not limited thereto. In addition, it is not limited to the structure, and the metal lines and pads may be disposed under the semiconductor substrate 110.

[0177] The insulating layer 80 is formed on the metal lines and pads. The insulating layer 80 may be made of an inorganic insulating material such as silicon oxide and / or silicon nitride, or a low dielectric constant (low-k) material such as SiC, SiCOH, SiCO, and SiOF. The insulating layer 80 has a channel 85 exposing the charge memory 55. The channel 85 may be filled with a filler.

[0178] The aforementioned optoelectronic device 100 is formed on the insulating layer 80. As described above, the optoelectronic device 100 includes a first electrode 10, an active layer 30, and a second electrode 20. Although the structure in which the first electrode 10, the active layer 30, and the second electrode 20 are sequentially stacked is shown in the figure as an example, the present disclosure is not limited to this structure, and the second electrode 20, the active layer 30, and the first electrode 10 may be arranged in this order. Additionally, according to Figure 1 the optoelectronic device is shown in the figure, but according to Figure 2 the optoelectronic device may also be applied in the same manner.

[0179] Both the first electrode 10 and the second electrode 20 may be transparent electrodes, and the active layer 30 may be the same as that described above with reference to Figure 1 and 2 The active layer 30 may selectively absorb light in the near-infrared wavelength region. Incident light from the side of the second electrode 20 may be photoelectrically converted by mainly absorbing light in the near-infrared wavelength region in the active layer 30. As annotated above with reference to Figure 1 the active layer 30 may include the aforementioned near-infrared absorber and thus may have improved sensitivity to near-infrared light, so that the operating performance and / or efficiency (e.g., photoelectric conversion performance and / or efficiency) of the organic sensor 300 in absorbing incident near-infrared light and / or converting the incident near-infrared light into an electrical signal can be improved.

[0180] A focusing lens (not shown) may be further formed on the optoelectronic device 100. The focusing lens may control the direction of incident light and focus the light in an area. The focusing lens may have a shape such as a cylinder or a hemisphere, but is not limited thereto.

[0181] According to some example embodiments, the organic sensor may be an organic infrared light sensor, such as an iris sensor or a depth sensor.

[0182] The iris sensor identifies a person by using the unique iris feature of each person, and particularly by capturing an image of the user's eye at an appropriate distance, processing the image, and comparing it with his / her stored image.

[0183] The depth sensor identifies the shape and position of an object from its three-dimensional information by capturing an image of the object at an appropriate distance from the user and processing the image. The depth sensor may be used, for example, as a face recognition sensor.

[0184] Figure 4 is a cross-sectional view showing an organic sensor according to some example embodiments.

[0185] According to some example embodiments, the organic sensor may include a plurality of sensors having different functions. For example, at least one of the plurality of sensors having different functions may be a biometric sensor, and the biometric sensor may be, for example, an iris sensor, a depth sensor, a fingerprint sensor, a blood vessel distribution sensor, etc., but is not limited thereto. For example, one sensor of the plurality of sensors having different functions may be an iris sensor, and another sensor of the plurality of sensors having different functions may be a depth sensor.

[0186] For example, the plurality of sensors may include, for example, a first infrared light sensor and a second infrared light sensor. The first infrared light sensor is configured to sense (e.g., selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion)) light in an infrared region (e.g., an infrared wavelength region) having a first wavelength (λ1) in the infrared wavelength region, and the second infrared light sensor is configured to sense (e.g., selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion)) light in an infrared region having a second wavelength (λ2) in the infrared wavelength region (e.g., an infrared wavelength region that is the same as or different from the infrared wavelength region including the first wavelength (λ1)).

[0187] The first wavelength (λ1) and the second wavelength (λ2) may be different, for example, in a wavelength region of about 750 nm to about 3000 nm, and for example, the difference between the first wavelength (λ1) and the second wavelength (λ2) may be greater than or equal to about 30 nm, greater than or equal to about 50 nm, greater than or equal to about 70 nm, greater than or equal to about 80 nm, or greater than or equal to about 90 nm.

[0188] For example, one of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region of about 780 nm to about 900 nm, and the other of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region of about 830 nm to about 1000 nm.

[0189] For example, one of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region of about 780 nm to about 840 nm, and the other of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region of about 910 nm to about 970 nm.

[0190] For example, one of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region of about 800 nm to about 830 nm, and the other of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region of about 930 nm to about 950 nm.

[0191] For example, one of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region of about 805 nm to about 815 nm, and the other of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region of about 935 nm to about 945 nm.

[0192] For example, one of the first wavelength (λ1) or the second wavelength (λ2) may be about 810 nm, and the other of the first wavelength (λ1) or the second wavelength (λ2) may be about 940 nm.

[0193] According to some example embodiments, the organic sensor 400 includes a dual - bandpass filter 95, a first infrared light sensor 100A, an insulating layer 80, and a semiconductor substrate 110 integrated with a second infrared light sensor 120 such that the second infrared light sensor 120 is at least partially embedded within the semiconductor substrate 110. As Figure 4 shown, the first infrared light sensor 100A and the second infrared light sensor 120 may be stacked, for example, may overlap in a vertical direction perpendicular to the top surface 110S of the semiconductor substrate 110.

[0194] As Figure 4 shown, the dual - bandpass filter 95 may be disposed on the front side of the organic sensor 400 and may selectively transmit infrared light including the first wavelength (λ1) (e.g., light in the infrared wavelength region) and infrared light including the second wavelength (λ2), and may block and / or absorb other light. Herein, other light may include light in the ultraviolet (UV) and visible regions.

[0195] As Figure 4 shown, the first infrared light sensor 100A may be associated with according to including reference Figure 1Some example embodiments of the optoelectronic device 100 are the same as those of the example embodiments described, but it will be understood that in some example embodiments, the first infrared light sensor 100A may be the same as the optoelectronic device 200 according to some example embodiments including reference Figure 2 described in the example embodiments.

[0196] As Figure 4 shown, the second infrared light sensor 120 may be integrated in the semiconductor substrate 110 and may be a light sensing device. The semiconductor substrate 110 (e.g., contained within the volume space defined by the outer surface of the semiconductor substrate 110) may be, for example, a silicon substrate, and may be integrated with the second infrared light sensor 120, the charge memory 55, and a transfer transistor (not shown).

[0197] The second infrared light sensor 120 may be a photodiode (e.g., a silicon-based photodiode), and may sense (e.g., absorb) the incident light, and the sensed information is transmitted by the transfer transistor. Here, the light entering the second infrared light sensor 120 is the light that passes through the dual-bandpass filter 95 and the first infrared light sensor 100A (e.g., selectively transmitted by the dual-bandpass filter 95 and the first infrared light sensor 100A), and may be infrared light in a specific (or, alternatively, predetermined) region including the second wavelength (λ2). All infrared light in a specific (or, alternatively, predetermined) region including the first wavelength (λ1) may be absorbed by the active layer 30 and may not reach the second infrared light sensor 120. In this case, it is not separately necessary to provide a separate filter for wavelength selectivity of the light entering the second infrared light sensor 120. However, when not all infrared light in a specific (or, alternatively, predetermined) region including the first wavelength (λ1) is absorbed by the active layer 30, a filter may be further provided between the first infrared light sensor 100A and the second infrared light sensor 120.

[0198] Therefore, in the organic sensor 400, the first infrared light sensor 100A may be understood to include an optoelectronic device (e.g., optoelectronic device 100 and / or 200) configured to sense (e.g., selectively absorb and / or convert (into an electrical signal, e.g., photoelectric conversion)) light in the first near-infrared wavelength region (e.g., the first near-infrared wavelength region including the first wavelength (λ1)) of the incident light, and the second infrared light sensor 100A may be understood to include another sensor configured to selectively absorb and / or convert (into an electrical signal, e.g., photoelectric conversion) light in a separate (different) wavelength region (e.g., a second near-infrared wavelength region different from the first near-infrared wavelength region, including the second wavelength (λ2) and not including the first wavelength (λ1)) of the incident light.

[0199] An organic sensor according to some example embodiments may include two infrared light sensors that respectively perform separate functions, and may thus operate as a combined sensor. Additionally, two sensors that perform separate functions are stacked in each pixel, and thus, while maintaining the size, the number of functions that each pixel performs for each sensor is doubled, and as a result, the sensitivity can be greatly improved.

[0200] As referred to above Figure 1 annotated, the active layer 30, or any part of the optoelectronic device 100 and / or 200 may include the above-mentioned near-infrared absorber, and may thus have improved sensitivity and / or absorption rate to near-infrared light, such that the operating performance and / or efficiency (e.g., photoelectric conversion performance and / or efficiency) of the organic sensor 400 in absorbing incident near-infrared light and / or photoelectrically converting the incident near-infrared light into an electrical signal can be improved. In some example embodiments, the second infrared light sensor 120 may include the above-mentioned near-infrared absorber, and may thus have improved sensitivity and / or absorption rate to near-infrared light, such that the operating performance and / or efficiency (e.g., photoelectric conversion performance and / or efficiency) of the organic sensor 400 in absorbing incident near-infrared light and / or converting the incident near-infrared light into an electrical signal can be improved.

[0201] Figure 5 is a cross-sectional view showing an example of an organic sensor according to some example embodiments.

[0202] An organic sensor according to some example embodiments may be an organic CMOS image sensor.

[0203] Referring to Figure 5 , an organic sensor 500 according to some example embodiments includes a semiconductor substrate 110 integrated with photosensing devices (e.g., photodiodes, including silicon-based photodiodes) 50a, 50b, and 50c, transfer transistors (not shown), and a charge memory 55, a lower insulating layer 60, color filters 70a, 70b, and 70c, an insulating layer 80, and an optoelectronic device 100.

[0204] The semiconductor substrate 110 may be integrated with photosensing devices 50a, 50b, and 50c, transfer transistors (not shown), and a charge memory 55 such that the photosensing devices 50a, 50b, and 50c are at least partially embedded within the semiconductor substrate 110 and are vertically overlapped by the optoelectronic device 100 in a vertical direction perpendicular to the top surface 110S. The photosensing devices 50a, 50b, and 50c may be photodiodes (e.g., silicon-based photodiodes), which may be configured to sense (e.g., selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion)) light in different visible wavelength regions.

[0205] The photosensing devices 50a, 50b, and 50c, the transfer transistor, and / or the charge memory 55 may be integrated in each pixel. For example, the photosensing device 50a may be included in the red pixel, the photosensing device 50b may be included in the green pixel, and the photosensing device 50c may be included in the blue pixel.

[0206] The photosensing devices 50a, 50b, and 50c sense (e.g., selectively absorb and / or convert (e.g., convert to an electrical signal, such as photoelectric conversion)) incident light. The information sensed by the photosensing devices may be transmitted by the transfer transistor. The charge memory 55 is electrically connected to the optoelectronic device 100 to be described later, and the information of the charge memory 55 may be transmitted by the transfer transistor.

[0207] Metal wires (not shown) and pads (not shown) are formed on the semiconductor substrate 110. To reduce signal delay, the metal wires and pads may be made of a metal having a low resistivity, such as aluminum (Al), copper (Cu), silver (Ag), and their alloys, but are not limited thereto. In addition, it is not limited to the above structure, and the metal wires and pads may be disposed under the photosensing devices 50a and 50b.

[0208] The lower insulating layer 60 is formed on the metal wires and pads. The lower insulating layer 60 may include the same or different material compositions as the insulating layer 80.

[0209] The color filters 70a, 70b, and 70c are formed on the lower insulating layer 60. The color filters 70a, 70b, and 70c include a red filter 70a formed in the red pixel, a green filter 70b formed in the green pixel, and a blue filter 70c formed in the blue pixel.

[0210] The insulating layer 80 (also referred to as the upper insulating layer) is formed on the color filters 70a, 70b, and 70c. The insulating layer 80 eliminates the steps caused by the color filters 70a, 70b, and 70c and flattens the surface.

[0211] The aforementioned optoelectronic device 100 is formed on the insulating layer 80. As described above, the optoelectronic device 100 includes a first electrode 10, an active layer 30, and a second electrode 20. Although the structure in which the first electrode 10, the active layer 30, and the second electrode 20 are sequentially stacked is shown in the figure as an example, the present disclosure is not limited to this structure, and the second electrode 20, the active layer 30, and the first electrode 10 may be arranged in this order. In addition, according to Figure 1 the optoelectronic device is shown in the figure, but according to Figure 2 the optoelectronic device may also be applied in the same manner.

[0212] Both the first electrode 10 and the second electrode 20 can be transparent electrodes, and the active layer 30 is the same as described above. The active layer 30 can selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in the near-infrared wavelength region. As noted above regarding the optoelectronic devices 100 and 200, any part of the optoelectronic device 100 (e.g., the first electrode 10, the second electrode 20, and / or the active layer 30) can include the aforementioned near-infrared absorber.

[0213] Incident light from the side of the second electrode 20 can be photoelectrically converted by mainly absorbing light in the near-infrared wavelength region in the active layer 30. Light in the remaining wavelength regions can pass through the first electrode 10 and the color filters 70a, 70b, and 70c. The light in the red wavelength region passing through the color filter 70a can be sensed by the photosensing device 50a, the light in the green wavelength region passing through the color filter 70b can be sensed by the photosensing device 50b, and the light in the blue wavelength region passing through the color filter 70c can be sensed by the photosensing device 50c.

[0214] As referred to above Figure 1 Noted, the organic layer 30 can include the above-mentioned near-infrared absorber, and thus can have improved sensitivity to near-infrared light, such that the operating performance and / or efficiency (e.g., photoelectric conversion performance and / or efficiency) of the organic sensor 500 when absorbing incident near-infrared light and / or converting the incident near-infrared light into an electrical signal can be improved.

[0215] Therefore, when an organic sensor includes an optoelectronic device (the optoelectronic device includes the near-infrared absorber and is configured to selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in a first near-infrared wavelength region), the organic sensor can include additional sensors, the additional sensors including a plurality of photodiodes (e.g., photosensing devices 50a, 50b, 50c) that are at least partially embedded in a semiconductor substrate and are configured to selectively absorb and / or convert (e.g., convert into an electrical signal, such as photoelectric conversion) light in a separate visible wavelength region (e.g., red, blue, and / or green light).

[0216] The organic sensor can be applied to various electronic devices (e.g., included therein), and the electronic devices can include, for example, a camera, a camcorder, a mobile phone having them therein, a display device, a security device, or a medical device, but are not limited thereto.

[0217] Figure 6 is a block diagram of a digital camera including an image sensor according to some example embodiments.

[0218] Reference Figure 6, the digital camera 1000 includes a lens 1010, an image sensor 1020, a motor 1030, and an engine 1040. The image sensor 1020 can be one of the image sensors according to some example embodiments of the example embodiments shown in Figures 3 to 5 . The lens 1010 focuses incident light on the image sensor 1020. The image sensor 1020 generates RGB data for the received light passing through the lens 1010. In some embodiments, the image sensor 1020 can interface with the engine 1040.

[0219] The motor 1030 can adjust the focus of the lens 1010 or execute a shutter in response to a control signal received from the engine 1040. The engine 1040 can control the image sensor 1020 and the motor 1030.

[0220] The engine 1040 can be connected to a host / application 1050. In an example embodiment, the motor 1030, the engine 1040, and the host / application 1050 can include processing circuitry, such as hardware including logic circuits; a hardware / software combination such as a processor that executes software; or a combination thereof. For example, the processing circuitry can more specifically include, but is not limited to, a central processing unit (CPU), an arithmetic logic unit (ALU), a digital signal processor, a microcomputer, a field programmable gate array (FPGA), a system on a chip (SoC), a programmable logic unit, a microprocessor, an application specific integrated circuit (ASIC), etc. One or more of a processor (not shown), a memory (not shown), the motor 1030, the engine 1040, or the host / application 1050 can be included in, include, and / or implement one or more instances of the following: processing circuitry, such as hardware including logic circuits, a hardware / software combination such as a processor that executes software; or a combination thereof. In some example embodiments, one or more instances of the processing circuitry can include, but are not limited to, a central processing unit (CPU), an application processor (AP), an arithmetic logic unit (ALU), a graphics processing unit (GPU), a digital signal processor, a microcomputer, a field programmable gate array (FPGA), a system on a chip (SoC), a programmable logic unit, a microprocessor, or an application specific integrated circuit (ASIC), etc. In some example embodiments, any memory, storage unit, etc. as described herein can include a non-transitory computer-readable storage device, such as a solid state drive (SSD), which stores an instruction program, and one or more instances of the processing circuitry can be configured to execute the instruction program to implement any of some or all of the functions of a processor (not shown), a memory (not shown), the motor 1030, the engine 1040, or the host / application 1050, etc. according to any example embodiment as described herein.

[0221] In the following, some example embodiments will be shown in more detail with reference to the embodiments. However, the example embodiments are not limited to these embodiments.

[0222] Synthesis Example

[0223] Synthesis Example 1: Synthesis of the compound represented by Chemical Formula 1-1

[0224] [Chemical Formula 1-1]

[0225]

[0226] 10-(5-(Tributylstannyl)thiophen-2-yl)-10H-phenothiazine (0.58 g, 1.02 mmol), 4,8-dibromobenzo[1,2-c;4,5-c]bis([1,2,5]thiadiazole) (0.3 g, 0.85 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.043 mmol) were dissolved in 15 ml of dry toluene, and then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.28 g of the product (yield: 45%).

[0227] MALDI-TOF molecular weight analysis: m / z 752

[0228] Synthesis Example 2: Synthesis of the compound represented by Chemical Formula 1-2

[0229] [Chemical Formula 1-2]

[0230]

[0231] 10-(5-(Tributylstannyl)thiophen-2-yl)-10H-phenoselenazine (0.63 g, 1.02 mmol), 4,8-dibromobenzo[1,2-c;4,5-c]bis([1,2,5]thiadiazole) (0.3 g, 0.85 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.043 mmol) were dissolved in 15 ml of dry toluene, and then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.24 g of the product (yield: 34%).

[0232] MALDI-TOF molecular weight analysis: 847 m / z

[0233] Synthesis Example 3: Synthesis of the compound represented by Chemical Formula 1-3

[0234] [Chemical Formula 1-3]

[0235]

[0236] 10-(5-(Tributylstannyl)thiophen-2-yl)-10H-phentellurazine (0.22 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 then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.08 g of the product (yield: 30%).

[0237] MALDI-TOF molecular weight analysis: 945 m / z

[0238] Synthesis Example 4: Synthesis of the compound represented by Chemical Formula 1-4

[0239] [Chemical Formula 1-4]

[0240]

[0241] 10,10-Dimethyl-5-(5-(5-(tributylstannyl)thiophen-2-yl)-5,10-dihydrodibenzo[b,e][1,4]azasiline (0.2 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 then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.08 g of the product (yield: 47%).

[0242] MALDI-TOF molecular weight analysis: 804 m / z

[0243] Synthesis Example 5: Synthesis of the compound represented by Chemical Formula 1-5

[0244] [Chemical Formula 1-5]

[0245]

[0246] 9,9-Dimethyl-10-(5-(tributylstannyl)thiophen-2-yl)-9,10-dihydroacridine (0.99 g, 0.17 mmol), 4,8-dibromobenzo[1,2-c;4,5-c]bis([1,2,5]thiadiazole) (0.05 g, 0.14 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.004 g, 0.007 mmol) were dissolved in 5 ml of dry toluene and then stirred at 110 °C for 18 h. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to give 0.023 g of the product (yield: 21%).

[0247] MALDI-TOF molecular weight analysis: 772 m / z

[0248] Synthesis Example 6: Synthesis of the compound represented by Chemical Formula 1-6

[0249] [Chemical Formula 1-6]

[0250]

[0251] 10-(5-(Tributylstannyl)thiophen-2-yl)-10H-phen azine (0.57 g, 1.02 mmol), 4,8-dibromobenzo[1,2-c;4,5-c]bis([1,2,5]thiadiazole) (0.3 g, 0.85 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.043 mmol) were dissolved in 15 ml of dry toluene and then stirred at 110 °C for 18 h. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to give 0.29 g of the product (yield: 47%).

[0252] MALDI-TOF molecular weight analysis: 720 m / z

[0253] Synthesis Example 7: Synthesis of the compound represented by Chemical Formula 1-7

[0254] [Chemical Formula 1-7]

[0255]

[0256] 9-(5-(Tributylstannyl)thiophen-2-yl)-9H-carbazole (1 g, 1.86 mmol), 4,8-dibromobenzo[1,2-c;4,5-c]bis([1,2,5]thiadiazole) (0.3 g, 0.85 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.043 mmol) were dissolved in 10 ml of dry toluene, and then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.33 g of the product (yield: 56%).

[0257] MALDI-TOF molecular weight analysis: 688 m / z

[0258] Synthesis Example 8: Synthesis of the compound represented by Chemical Formula 2-1

[0259] [Chemical Formula 2-1]

[0260]

[0261] 10-(5-(Tributylstannyl)selenophen-2-yl)-10H-phenothiazine (0.63 g, 1.02 mmol), 4,8-dibromobenzo[1,2-c;4,5-c]bis([1,2,5]thiadiazole) (0.3 g, 0.85 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.043 mmol) were dissolved in 15 ml of dry toluene, and then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.31 g of the product (yield: 43%).

[0262] MALDI-TOF molecular weight analysis: 847 m / z

[0263] Synthesis Example 9: Synthesis of the compound represented by Chemical Formula 2-2

[0264] [Chemical Formula 2-2]

[0265]

[0266] 10-(5-(Tributylstannyl)selenophen-2-yl)-10H-phenoselenazine (0.23 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 then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.09 g of the product (yield: 34%).

[0267] MALDI-TOF molecular weight analysis: 941 m / z

[0268] Synthesis Example 10: Synthesis of the compound represented by Chemical Formula 2-3

[0269] [Chemical Formula 2-3]

[0270]

[0271] 10-(5-(Tributylstannyl)thiophen-2-yl)-10H-phenteoxazine (0.24 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 then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.05 g of the product (yield: 17%).

[0272] MALDI-TOF molecular weight analysis: 1041 m / z

[0273] Synthesis Example 11: Synthesis of the compound represented by Chemical Formula 2-4

[0274] [Chemical Formula 2-4]

[0275]

[0276] 10,10-Dimethyl-5-(5-(tributylstannyl)thiophen-2-yl)-5,10-dihydrodibenzo[b,e][1,4]azasilinane (0.22 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 then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.1 g of the product (yield: 32%).

[0277] MALDI-TOF molecular weight analysis: 900 m / z

[0278] Synthesis Example 12: Synthesis of the compound represented by Chemical Formula 2-5

[0279] [Chemical Formula 2-5]

[0280]

[0281] 10-(5-(Tributylstannyl)thiophen-2-yl)-10H-phenothiazine 10-(5-(Tributylstannyl)thiophen-2-yl)-10H-phenothiazine (0.61 g, 1.02 mmol), 4,8-dibromobenzo[1,2-c;4,5-c]bis([1,2,5]thiadiazole) (0.3 g, 0.85 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.043 mmol) were dissolved in 15 ml of dry toluene and then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.3 g of the product (yield: 43%).

[0282] MALDI-TOF molecular weight analysis: 815 m / z

[0283] Synthesis Example 13: Synthesis of the compound represented by Chemical Formula 2-6

[0284] [Chemical Formula 2-6]

[0285]

[0286] 9,9-Dimethyl-10-(5-(tributylstannyl)thiophen-2-yl)-9,10-dihydroacridine (0.11 g, 0.17 mmol), 4,8-dibromobenzo[1,2-c;4,5-c]bis([1,2,5]thiadiazole) (0.05 g, 0.14 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.004 g, 0.007 mmol) were dissolved in 5 ml of dry toluene and then stirred at 110 °C for 18 hours. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to obtain 0.02 g of the product (yield: 16%).

[0287] MALDI-TOF molecular weight analysis: 868 m / z

[0288] Synthesis Example 14: Synthesis of the compound represented by Chemical Formula 2-7

[0289] [Chemical Formula 2-7]

[0290]

[0291] 9-(5-(Tributylstannyl)thiophen-2-yl)-9H-carbazole (0.55 g, 1.02 mmol), 4,8-dibromobenzo[1,2-c;4,5-c]bis([1,2,5]thiadiazole) (0.3 g, 0.85 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.043 mmol) were dissolved in 15 ml of dry toluene and then stirred at 110 °C for 18 h. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to give 0.33 g of the product (yield: 50%).

[0292] MALDI-TOF molecular weight analysis: 783 m / z

[0293] Synthesis Comparative Example 1: Synthesis of the compound represented by Chemical Formula 3-1

[0294] [Chemical Formula 3-1]

[0295]

[0296] 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 then stirred at 110 °C for 18 h. At the completion of the reaction, the toluene was concentrated and evaporated, and dichloromethane was used for precipitation to give 0.1 g of the product (yield: 52%).

[0297] MALDI-TOF molecular weight analysis: 692 m / z

[0298] Evaluation I

[0299] The maximum absorption wavelength (λ 最大 ) of the compounds according to Synthesis Examples 1-14 was calculated by the B3LYP / 6-31G(d) level theory described in "M.J. Frisch, et al., Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT 2009" using the "Gaussian 09 program" method. The results of Synthesis Examples 1-5 and Synthesis Examples 8-13 are shown in Table 1.

[0300] (Table 1)

[0301] <![CDATA[λ 最大 (nm)]]> Synthesis Example 1 983 Synthesis Example 2 986 Synthesis Example 3 998 Synthesis Example 4 1004 Synthesis Example 5 993 Synthesis Example 8 1021 Synthesis Example 9 1025 Synthesis Example 10 1047 Synthesis Example 11 1046 Synthesis Example 12 1018 Synthesis Example 13 1037

[0302] Referring to Table 1, the compounds according to Synthesis Examples 1 to 5 and 8 to 13 exhibit excellent wavelength absorption in the near-infrared wavelength region.

[0303] Evaluation II

[0304] The deposition characteristics of the compounds according to Synthesis Examples 1 to 14 and Synthesis Comparative Example 1 were evaluated. The deposition characteristics were evaluated as follows: the compound was sublimated under a high vacuum of less than or equal to 10 Pa, and then the weight loss depending on the temperature increase was measured by thermogravimetric analysis. The results of the compounds of Synthesis Examples 1 and 5 are shown in Table 2. The compound according to Synthesis Comparative Example 1 decomposed during the deposition process and could not be evaluated.

[0305] (Table 2)

[0306] <![CDATA[T s (℃)(-10 wt%)]]> Synthesis Example 1 330 Synthesis Example 5 335

[0307] *T s (℃)(-10 wt%): The temperature at which the weight of the sample decreases by 10 wt%

[0308] Referring to Table 2, the compounds according to Synthesis Examples 1 and 5 exhibit excellent deposition characteristics.

[0309] Examples and Comparative Examples: Fabrication of Optoelectronic Devices

[0310] An anode with a thickness of 150 nm was formed by sputtering ITO on a glass substrate. Subsequently, each of the compounds according to Synthesis Examples 1 to 14 was co-deposited with C60 on the anode at a volume ratio of 1:1 to form an active layer (photoelectric conversion layer) with a thickness of 150 nm. Then, C60 was deposited on the photoelectric conversion layer to form a 30-nm-thick auxiliary layer. Then, ITO was sputtered on the auxiliary layer to form a 7-nm-thick cathode. Aluminum oxide (Al2O3) was deposited on the cathode to form a 50-nm-thick antireflection layer, and it was encapsulated with a glass plate to fabricate the optoelectronic devices according to Examples 1 to 14.

[0311] On the other hand, the compound according to Synthesis Comparative Example 1 decomposed during the deposition process, so that no thin film was formed, and thus the optoelectronic device could not be fabricated.

[0312] Evaluation III

[0313] Evaluate the photoelectric conversion efficiency of the optoelectronic devices according to Examples 1 to 14. The photoelectric conversion efficiency was measured by using an IPCE measurement system (TNE Technology Co., Ltd., Korea). First, the IPCE measurement system was calibrated by using a Si photodiode (Hamamatsu Photonics, K.K., Japan), and it was installed on the optoelectronic device to measure the external quantum efficiency in the wavelength range of about 400 nm to about 1000 nm. The results of the optoelectronic device according to Example 5 are shown in Figure 7 in. Figure 7 is a diagram showing the external quantum efficiency of the optoelectronic device according to Example 5. Refer to Figure 7 , the optoelectronic device according to Example 5 exhibits excellent external quantum efficiency in the near-infrared region (810 nm to about 910 nm).

[0314] Although the present disclosure has been described in connection with example embodiments that are presently considered to be practical, it will be understood that the inventive concept is not limited to the disclosed example embodiments. On the contrary, the inventive concept is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

[0315] <Reference Signs>

[0316] 10: First electrode

[0317] 20: Second electrode

[0318] 30: Active layer

[0319] 50a, 50b, 50c: Light sensing device

[0320] 55: Charge memory

[0321] 70a, 70b, 70c: Color filter

[0322] 80: Insulating layer

[0323] 100, 200: Optoelectronic device

[0324] 300, 400, 500: Organic sensor

Claims

1. Near-infrared absorber, comprising: A compound represented by Chemical Formula 1: [Chemical Formula 1] Wherein, in Chemical Formula 1 Ar is an unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring, X 1 is O, S, Se, or Te, X 2 is O, S, Se, or Te, Y 1 and Y 2 are independently O, S, Se, or Te, and Ar 1 and Ar 2 are independently a functional group represented by the chemical formula A [Chemical Formula A] Wherein Chemical Formula A is represented by one of Chemical Formulas A-1 to A-5: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] [Chemical Formula A-4] [Chemical Formula A-5] Wherein, in Chemical Formula A-1, G is -Se-, -Te-, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h )=C(R i ))-, where R b 、R c 、R d 、R e 、R f 、R g 、R h and R i independently are hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C10 aryl group, where R b and R c 、R d and R e 、R f and R g 、or R h and R i independently exist, and the n of -(CR f R g ) n - is an integer of 1 or 2, and R 4a to R 4d and R 5a to R 5d has the following structure such that R 4a to R 4d and R 5a to R 5d are independently hydrogen, deuterium, C1 to C30 alkyl, halogen, cyano (-CN), or a combination thereof. Wherein, in Chemical Formula A-2, G is -Se-, -Te-, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h )=C(R i ))-, where R b 、R c 、R d 、R e 、R f 、R g 、R h and R i are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C10 aryl group, wherein R b and R c 、R d and R e 、R f and R g 、or R h and R i exist independently, and n in -(CR f R g ) n - is an integer of 1 or 2, and R 4a to R 4d and R 5b to R 5d has the following structure such that R 4a to R 4d and R 5b to R 5d are independently hydrogen, deuterium, a C1-C30 alkyl group, a halogen, a cyano group (-CN), or a combination thereof, Wherein, in Chemical Formula A-3, G is -Se-, -Te-, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h ))=C(R i ))-, where R b , R c , R d , R e , R f , R g , R h and R i are independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C10 aryl, wherein R b and R c , R d and R e , R f and R g , or R h and R i exists independently, and -(CR f R g ) n - n is an integer of 1 or 2, and R 4b to R 4d and R 5b to R 5d has the following structure such that R 4b to R 4d and R 5b to R 5d are independently hydrogen, deuterium, C1 to C30 alkyl, halogen, cyano (-CN), or a combination thereof, Wherein, in Chemical Formula A-4, G is -Se-, -Te-, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h )=C(R i ))-, where R b , R c , R d , R e , R f , R g , R h and R i are independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C10 aryl, wherein R b and R c , R d and R e , R f and R g , or R h and R i exists independently, and -(CR f R g ) n - n is an integer of 1 or 2, and R 4a to R 4d and R 5b and R 5d has the following structure such that R 4a to R 4d and R 5b and R 5d are each independently hydrogen, deuterium, a C1-C30 alkyl group, a halogen, a cyano group (-CN), or a combination thereof, Wherein, in Chemical Formula A-5, G is -Se-, -Te-, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h ))=C(R i ))-, where R b 、R c 、R d 、R e 、R f 、R g 、R h and R i are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C10 aryl group, where R b and R c 、R d and R e 、R f and R g 、or R h and R i exist independently, and n in -(CR f R g ) n - is an integer of 1 or 2, and R 4a to R 4d and R 5b and R 5c has the following structure such that R 4a to R 4d and R 5b to R 5c are independently hydrogen, deuterium, C1 to C30 alkyl, halogen, cyano (-CN), or a combination thereof, and * is a connection point, Wherein "substituted" means that the hydrogen of the functional group is replaced by the following: a halogen atom, a hydroxyl group, a nitro group, a cyano group, an amino group, a mercapto group, a C1 to C20 alkyl group, a C1 to C30 alkoxy group, or a combination thereof, Wherein the near-infrared absorber has a peak absorption wavelength in the wavelength range of about 700 nm to about 3000 nm.

2. The near-infrared absorber according to claim 1, wherein in Chemical Formula 1, Ar is an unsubstituted benzene ring.

3. A near-infrared absorption / blocking film, comprising the near-infrared absorber according to any one of claims 1-2.

4. An optoelectronic device, 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 comprises the near-infrared absorber according to any one of claims 1-2.

5. The optoelectronic device according to claim 4, wherein the active layer further comprises fullerene or a fullerene derivative.

6. The optoelectronic device according to claim 5, wherein the active layer has a peak absorption wavelength in the wavelength range of about 700 nm to about 3000 nm.

7. An organic sensor, comprising the optoelectronic device according to any one of claims 4-6.

8. An electronic device, comprising the organic sensor according to claim 7 or the optoelectronic device according to any one of claims 4-6.

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