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

Abstract

The present invention relates to a near-infrared absorber, a near-infrared absorption / blocking film, an optoelectronic device, an organic sensor, and an electronic device. The near-infrared absorber includes a compound represented by Chemical Formula 1. The near-infrared absorption / blocking film, the optoelectronic device, the organic sensor, and the electronic device may include the near-infrared absorber. In Chemical Formula 1, Ar, Ar 1 、Ar 2 、Ar 3 、Ar 4 、X 1 、X 2 、L 1 、L 2 、R 1 、and R 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 - 0151737, filed on November 22, 2019, and Korean Patent Application No. 10 - 2019 - 0152735, filed on November 25, 2019, with the Korean Intellectual Property Office, the entire contents of each of which are 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 for improving the sensitivity of sensors in low - light environments or used as biometric devices have been studied. 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 is a substituted or unsubstituted C6 - C30 aromatic ring, a substituted or unsubstituted C3 - C30 heteroaromatic ring, or a combination thereof,

[0016] X 1 is O, S, Se, Te, S(=O), S(=O2), NR a , CR b R c , SiR d R e , GeR f R g , CR h =CR i , or CR hh =CR ii (wherein R a , R b , R c , R d , R e , R f , R g , R h , and R i are independently hydrogen, deuterium, C1-C30 alkyl, C1-C30 haloalkyl, C6-C30 aryl, C6-C30 aryloxy, C3-C30 heteroaryl, halogen, cyano, or a combination thereof, R hh and R ii are independently (CH) where w is a positive integer w or at least one heteroatom of O, N, S, Se, or Te, and R hh and R ii are connected to each other to form an aromatic ring or a heteroaromatic ring),

[0017] X 2 is O, S, Se, Te, C, CR x -CR y , CR xx -CR yy , S(=O), or S(=O2) (wherein R x and R y are independently hydrogen, deuterium, C1-C30 alkyl, C1-C30 haloalkyl, C6-C30 aryl, C6-C30 aryloxy, C3-C30 heteroaryl, halogen, cyano, or a combination thereof, R xx and R yy are independently (CH) where v is a positive integer v or at least one heteroatom of O, N, S, Se, or Te, and R xx and R yy are connected to each other to form an aromatic ring or a heteroaromatic ring),

[0018] Ar 1 and Ar 2A heteroaromatic group independently having at least one heteroatom including O, S, Se, or Te,

[0019] Ar 3 and Ar 4 are independently a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 heteroaromatic group, or a fused ring group thereof,

[0020] R 1 and R 2 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxy, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C10 aryl group, or a substituted or unsubstituted C3-C10 heteroaryl group, and

[0021] L 1 and L 2 are independently 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 are independently hydrogen, deuterium, halogen, cyano, 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 or are connected to each other to form a separate ring, and n of -(CR f R g ) n - is an integer of 1 or 2).

[0022] In Chemical Formula 1, Ar can 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.

[0023] 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.

[0024] In Chemical Formula 1, Ar can be a part of a group of parts represented by Chemical Formula A-1, each part including at least one aromatic ring and left and right linking groups.

[0025] [Chemical Formula A-1]

[0026]

[0027] In Chemical Formula A-1,

[0028] the hydrogen of each aromatic ring can be replaced by a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, -SiH3, or a C1-C10 alkylsilyl group,

[0029] the adjacent pair of individual * within the at least one aromatic ring is a connecting part with a ring containing N-X 1 -N in Chemical Formula 1 or a ring containing N=X 2 =N in Chemical Formula 1, and

[0030] the * of the left and right linking groups is a connecting part with an individual corresponding one of Ar 1 or Ar 2 in Chemical Formula 1.

[0031] In Chemical Formula 1, Ar can be a part of a group of parts represented by Chemical Formula A-2, each part including at least one aromatic ring and left and right linking groups.

[0032] [Chemical Formula A-2]

[0033]

[0034] In Chemical Formula A-2,

[0035] the hydrogen of each aromatic ring can be replaced by a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, -SiH3, or a C1-C10 alkylsilyl group,

[0036] the adjacent pair of individual * within the at least one aromatic ring is a connecting part with a ring containing N-X 1-N ring and N═X of Chemical Formula 1 2 The connecting part of a single corresponding one of the ═N rings, and

[0037] The * of the left and right linking groups is linked to a single corresponding one of Ar of Chemical Formula 1 1 and Ar 2 The connecting part of a single corresponding one.

[0038] In Chemical Formula 1, when X 2 is CR xx -CR yy The aromatic ring formed by connecting R xx with R yy can be 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; or 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.

[0039] In Chemical Formula 1, when X 2 is CR xx -CR yy The aromatic ring formed by connecting R xx with R yy can be a part of a group of parts represented by Chemical Formula B-1, each part including at least one aromatic ring.

[0040] [Chemical Formula B-1]

[0041]

[0042] In Chemical Formula B-1,

[0043] The hydrogen of each aromatic ring can be replaced by 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, and

[0044] The * within the at least one aromatic ring is the connecting part to the carbon of CR xx -CR yy The connecting part.

[0045] In Chemical Formula 1, when X 2 is CR xx -CR yy The aromatic ring formed by connecting R xx with Ryy The formed aromatic ring may be a part of a group of moieties represented by Chemical Formula B-2, each moiety including at least one aromatic ring.

[0046] [Chemical Formula B-2]

[0047]

[0048] In Chemical Formula B-2,

[0049] the hydrogen of each aromatic ring may be replaced by 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, and

[0050] the * within the at least one aromatic ring is the connecting moiety to the carbon of CR xx -CR yy is the connecting moiety.

[0051] In Chemical Formula 1, when X 2 is CR xx -CR yy the aromatic ring formed by connecting R xx to R yy may be one of the moieties represented by Chemical Formulas B-3-1 and B-3-2.

[0052] [Chemical Formula B-3-1]

[0053]

[0054] [Chemical Formula B-3-2]

[0055]

[0056] In Chemical Formulas B-3-1 and B-3-2,

[0057] Ar 11 and Ar 12 are independently a substituted or unsubstituted C6-C30 arene group or a substituted or unsubstituted C3-C30 heteroarene group,

[0058] In Chemical Formula B-3-1, Z 1 and Z 2 are independently CR a or N (wherein R ais hydrogen, deuterium, a C1-C30 alkyl group, a C1-C30 haloalkyl group, -SiH3, a C1-C30 alkylsilyl group, -NH2, a C1-C30 alkylamine group, a C6-C30 arylamine 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),

[0059] The hydrogen of each aromatic ring may be replaced by 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, and

[0060] the * within the at least one aromatic ring is the connecting moiety to the carbon of CR xx -CR yy of.

[0061] The moiety represented by Chemical Formula B-3-1 may be one of a group of moieties represented by Chemical Formula B-3-11, each moiety including at least one aromatic ring.

[0062] [Chemical Formula B-3-11]

[0063]

[0064] In Chemical Formula B-3-11,

[0065] The hydrogen of each aromatic ring may be replaced by 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, and

[0066] the * within the at least one aromatic ring is the connecting moiety to the carbon of CR xx -CR yy of.

[0067] The moiety represented by Chemical Formula B-3-2 may be one of a group of moieties represented by Chemical Formula B-3-21, each moiety including at least one aromatic ring.

[0068] [Chemical Formula B-3-21]

[0069]

[0070] In Chemical Formula B-3-21,

[0071] The hydrogen of each aromatic ring may be replaced by 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.

[0072] X a and X b are independently O, S, Se, Te, NR a , SiR b R c , or GeR d R e (wherein R a , R b , R c , R d , and R e are independently hydrogen, a halogen, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C6-C30 aryloxy group), and

[0073] the * within the aromatic ring is the connecting moiety to the carbon of CR xx -CR yy .

[0074] In Chemical Formula 1, Ar 1 and Ar 2 may be the same or different and may each be represented by one of Chemical Formula C-1-1, Chemical Formula C-1-2, or Chemical Formula C-1-3, and each of Chemical Formula C-1-1, Chemical Formula C-1-2, or Chemical Formula C-1-3 includes at least one aromatic ring.

[0075] [Chemical Formula C-1-1]

[0076]

[0077] [Chemical Formula C-1-2]

[0078]

[0079] [Chemical Formula C-1-3]

[0080]

[0081] In Chemical Formulas C-1-1 to C-1-3,

[0082] The hydrogen of each aromatic ring may be replaced by 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.

[0083] Y 1 is O, S, Se, Te, S(=O), S(=O)2, NR a1 , SiR b1 R c1 , or GeR d1 R e1 (wherein R a1 , R b1 , R c1 , R d1 , and R e1 are 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),

[0084] Y 2 is O, S, Se, Te, S(=O), S(=O)2, NR a2 , SiR b2 R c2 , GeR d2 R e2 , or

[0085] CR f2 R g2 (wherein R a2 , R b2 , R c2 , R d2 , R e2 , R f2 , and R g2 are 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),

[0086] R b1 and R c1 , R d1 and R e1 , R b2 and R c2 , R d2and R e2 and R f2 and R g2 may exist independently or in combination with each other to form a spiro ring,

[0087] The * outside the at least one aromatic ring is the connection point with Ar of Formula 1, and

[0088] the * inside the at least one aromatic ring is the connection part with the N(R 1 )-containing ring including R of Formula 1 and the N(R 1 )-containing ring including R of Formula 1. 2 2 1 ) of Formula 1.

[0089] In Formula 1, Ar 1 and Ar 2 are the same or different and may each be represented by one of Formulas C-2-1 to C-2-4, and each of Formulas C-2-1 to C-2-4 includes at least one aromatic ring.

[0090] [Formula C-2-1]

[0091]

[0092] [Formula C-2-2]

[0093]

[0094] [Formula C-2-3]

[0095]

[0096] [Formula C-2-4]

[0097]

[0098] In Formulas C-2-1 to C-2-4,

[0099] the hydrogen of each aromatic ring may be replaced by 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,

[0100] Y 1 is O, S, Se, Te, S(=O), S(=O)2, NR a1 , SiR b1 R c1 , or GeR d1 R e1 (where R a1 , Rb1 , R c1 , R d1 , and R e1 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3, C1-C10 alkylsilyl, -NH3, C1-C10 alkylamine group, C6-C10 arylamine group, C6-C14 aryl, C6-C14 aryloxy, C3-C12 heteroaryl, halogen, cyano, or a combination thereof),

[0101] R b1 and R c1 and R d1 and R e1 are independently present or combine with each other to form a spiro ring,

[0102] The * outside the at least one aromatic ring is the connection point to Ar of Formula 1, and

[0103] The * inside the at least one aromatic ring is the connecting part to the ring containing N(R 1 ) of Formula 1 and the ring containing N(R 1 ) of Formula 1 that includes R 2 and the ring containing N(R 2 ) of Formula 1 that includes R

[0104] In Formula 1, Ar 1 and Ar 2 can be the same or different, and can each be represented by one of Formulas C-3-1 to C-3-6, and each of Formulas C-3-1 to C-3-6 includes at least one aromatic ring.

[0105] [Formula C-3-1]

[0106]

[0107] [Formula C-3-2]

[0108]

[0109] [Formula C-3-3]

[0110]

[0111] [Formula C-3-4]

[0112]

[0113] [Formula C-3-5]

[0114]

[0115] [Chemical formula C-3-6]

[0116]

[0117] In chemical formulas C-3-1 to C-3-6,

[0118] the hydrogen of each aromatic ring may be replaced by 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,

[0119] Y 1 is O, S, Se, Te, S(=O), S(=O)2, NR a1 、SiR b1 R c1 、or GeR d1 R e1 (wherein R a1 、R b1 、R c1 、R d1 and R e1 are 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),

[0120] Y 2 is O, S, Se, Te, S(=O), S(=O)2, NR a2 、SiR b2 R c2 、GeR d2 R e2 、or CR f2 R g2 (wherein R a2 、R b2 、R c2 、R d2 、R e2 、R f2 and R g2 are 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),

[0121] R b1and R c1 , R d1 and R e1 , R b2 and R c2 , R d2 and R e2 , and R f2 and R g2 may exist independently or be combined with each other to form a spiro ring,

[0122] The at least one aromatic ring outside the * is the connection point with Ar of Chemical Formula 1, and

[0123] The * in the at least one aromatic ring is the same as that of Formula 1 including R 1 N(R 1 ) and the ring of formula 1 including R 2 N(R 2 )'s connecting part of the ring.

[0124] In Chemical Formula 1, Ar 1 and Ar 2 may be the same or different, and may each be represented by one of Chemical Formula C-4-1 or Chemical Formula C-4-2, each of which includes at least one aromatic ring.

[0125] [Chemical formula C-4-1]

[0126]

[0127] [Chemical formula C-4-2]

[0128]

[0129] In chemical formulas C-4-1 and C-4-2,

[0130] The hydrogen of each aromatic ring may be replaced by halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C1-C30 haloalkyl, -SiH3, C1-C30 alkylsilyl, C6-C30 aryl, C6-C30 aryloxy, or C3-C30 heteroaryl,

[0131] Y 1 For 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 e1independently is 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),

[0132] Y 2 is O, S, Se, Te, S(=O), S(=O)2, NR a2 , SiR b2 R c2 , GeR d2 R e2 , or CR f2 R g2 (wherein R a2 , R b2 , R c2 , R d2 , R e2 , R f2 and R g2 are 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),

[0133] 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 can independently exist or combine with each other to form a spiro ring,

[0134] The * outside the at least one aromatic ring is the connection point to Ar of Formula 1, and

[0135] The * inside the aromatic ring is the connection part to the ring containing N(R 1 ) of Formula 1 and the ring containing N(R 1 ) of Formula 1 including R 2 . 2 ) of the ring including R

[0136] In Formula 1, Ar 1 and Ar 2may be the same or different and may each be represented by one of Chemical Formulas C-5-1 to C-5-8, each of which includes at least one aromatic ring.

[0137]

[0138] In Chemical Formulas C-5-1 to C-5-8,

[0139] the hydrogen of each aromatic ring may be replaced by 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,

[0140] Y 1 is O, S, Se, Te, S(=O), S(=O)2, NR a1 、SiR b1 R c1 、or GeR d1 R e1 (wherein R a1 、R b1 、R c1 、R d1 、and R e1 are 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),

[0141] Y 2 and Y 3 are independently O, S, Se, Te, S(=O), S(=O)2, NR a2 、SiR b2 R c2 、GeR d2 R e2 、or CR f2 R g2 (wherein R a2 、R b2 、R c2 、R d2 、R e2 、R f2 、and R g2independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3, C1-C10 alkylsilyl, -NH3, C1-C10 alkylamine, C6-C10 arylamine, C6-C14 aryl, C6-C14 aryloxy, C3-C12 heteroaryl, halogen, cyano, or a combination thereof,

[0142] 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 may exist independently or be combined with each other to form a spiro ring,

[0143] The at least one aromatic ring outside the * is the connection point with Ar of Chemical Formula 1, and

[0144] The * in the at least one aromatic ring is the same as that of Formula 1 including R 1 N(R 1 ) and the ring of formula 1 including R 2 N(R 2 )'s connecting part of the ring.

[0145] The near infrared absorber may have a peak absorption wavelength in a wavelength region of about 750 nm to about 3000 nm.

[0146] According to some example embodiments, there is provided a near infrared absorbing / blocking film including the near infrared absorber.

[0147] According to some example embodiments, a photoelectric device includes first and second electrodes facing each other, and an active layer between the first and second electrodes, wherein the active layer includes a near infrared absorber including a compound represented by Chemical Formula 1.

[0148] According to some example embodiments, there is provided an organic sensor including the optoelectronic device.

[0149] According to some example embodiments, there is provided an electronic device including the optoelectronic device or the organic sensor.

[0150] According to some example embodiments, an optoelectronic device may include: a first electrode and a second electrode facing each other; an active layer between the first electrode and the second electrode; and a charge assisting layer between the active layer and the first electrode or between the active layer and the second electrode. The charge assisting layer may include a near-infrared absorber, and the near-infrared absorber includes a compound represented by Chemical Formula 1:

[0151] [Chemical Formula 1]

[0152]

[0153] Wherein, in Chemical Formula 1,

[0154] Ar is a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, or a combination thereof, and X 1 is O, S, Se, Te, S(=O), S(=O2), NR a , CR b R c , SiR d R e , GeR f R g , CR h =CR i , or CR hh =CR ii , wherein R a , R b , R c , R d , R e , R f , R g , R h , and R i are 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, and R hh and R ii are independently (CH) w where w is a positive integer, or at least one heteroatom of O, N, S, Se, or Te, and R hh and R ii are connected to each other to form an aromatic ring or a heteroaromatic ring,

[0155] X 2 is O, S, Se, Te, C, CR x -CR y , CR xx -CR yy , S(=O) or S(=O2), wherein R xand R y are 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 xx and R yy are independently (CH) where v is a positive integer v or at least one heteroatom of O, N, S, Se, or Te, and R xx and R yy are connected to each other to form an aromatic ring or a heteroaromatic ring,

[0156] Ar 1 and Ar 2 are independently heteroaromatic groups including at least one heteroatom of O, S, Se, or Te,

[0157] Ar 3 and Ar 4 are independently a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a fused ring group thereof,

[0158] R 1 and R 2 are independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C10 aryl group, or a substituted or unsubstituted C3-C10 heteroaryl group, and

[0159] L 1 and L 2 are independently 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 are independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C10 aryl group, where Rb and R c , R d and R e , R f and R g , or R h and R i exist independently or are linked to each other to form a single ring, and -(CR f R g ) n -n is an integer of 1 or 2.

[0160] The active layer may further include the near infrared absorber.

[0161] According to some example embodiments, an organic sensor may include: a semiconductor substrate; a first optoelectronic device on the semiconductor substrate, the first optoelectronic device configured to selectively absorb light in a first near-infrared wavelength region; and an additional sensor configured to selectively absorb light in a separate wavelength region different from the first near-infrared wavelength region. The first optoelectronic device may include a near-infrared absorber, the near-infrared absorber including a compound represented by Chemical Formula 1:

[0162] [Chemical formula 1]

[0163]

[0164] Wherein, in Chemical Formula 1,

[0165] Ar is a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, or a combination thereof,

[0166] X 1 For O, S, Se, Te, S(=O), S(=O2), NR a , CR b R c 、SiR d R e ,GeR f R g , CR h =CR i , or CR hh =CR ii , where R a , R b , R c , R d , R e , R f , R g , R h , and R iIndependently 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 Independently is (CH) where w is a positive integer w Or at least one heteroatom of O, N, S, Se, or Te, and R hh and R ii Are connected to each other to form an aromatic ring or a heteroaromatic ring,

[0167] X 2 Is O, S, Se, Te, C, CR x -CR y 、CR xx -CR yy 、S(=O) or S(=O2), where R x and R y 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 xx and R yy Independently is (CH) where v is a positive integer v Or at least one heteroatom of O, N, S, Se, or Te, and R xx and R yy Are connected to each other to form an aromatic ring or a heteroaromatic ring,

[0168] Ar 1 and Ar 2 Independently are heteroaromatic groups including at least one heteroatom of O, S, Se, or Te,

[0169] Ar 3 and Ar 4 Independently are substituted or unsubstituted C6-C30 aromatic hydrocarbon groups, substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon groups, or their fused ring groups,

[0170] R 1 and R 2 Independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C10 aryl group, or a substituted or unsubstituted C3-C10 heteroaryl group, and

[0171] L 1 and L 2 Independently 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 ))-, wherein R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、and R i are independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, wherein R b and R c 、R d and R e 、R f and R g 、or R h and R i are independently present or connected to each other to form a separate ring, and n of -(CR f R g ) n - is an integer of 1 or 2.

[0172] The additional sensor may be an infrared light sensor at least partially embedded in the semiconductor substrate, and the separate wavelength region may be a separate near-infrared wavelength region different from the first near-infrared wavelength region, and the first optoelectronic device and the infrared light sensor may overlap in a vertical direction perpendicular to the top surface of the semiconductor substrate.

[0173] The additional sensor may include a plurality of photodiodes at least partially embedded in the semiconductor substrate, the plurality of photodiodes being configured to selectively absorb light in separate visible wavelength regions, and the first optoelectronic device and the plurality of photodiodes may overlap in a vertical direction perpendicular to the top surface of the semiconductor substrate.

[0174] The organic sensor may further include an additional optoelectronic device on the semiconductor substrate, the additional optoelectronic device being between the first optoelectronic device and the semiconductor substrate, the additional optoelectronic device being configured to selectively absorb light in an additional wavelength region different from the first near-infrared wavelength region and the separate visible wavelength regions.

[0175] The additional sensor may include at least one additional optoelectronic device vertically stacked between the first optoelectronic device and the semiconductor substrate, and each individual optoelectronic device of the at least one additional optoelectronic device includes an individual photoelectric conversion layer and is configured to selectively absorb light in an individual corresponding wavelength region different from the first near-infrared wavelength region.

[0176] The first optoelectronic device may include: a first electrode and a second electrode facing each other; and an active layer between the first electrode and the second electrode, wherein the active layer includes the near-infrared absorber.

[0177] The first optoelectronic device may include: a first electrode and a second electrode facing each other; an active layer between the first electrode and the second electrode; and a charge assisting layer between the active layer and the first electrode, or between the active layer and the second electrode. The charge assisting layer may include the near-infrared absorber.

[0178] The near-infrared absorber may exhibit good absorption properties in the near-infrared region and may thus be effectively used in optoelectronic devices and / or organic sensors. Description of the Drawings

[0179] Figure 1 A cross-sectional view showing an optoelectronic device according to some example embodiments,

[0180] Figure 2 A cross-sectional view showing an optoelectronic device according to some example embodiments,

[0181] Figure 3 A cross-sectional view showing an organic sensor according to some example embodiments,

[0182] Figure 4 A cross-sectional view showing an organic sensor according to some example embodiments,

[0183] Figure 5 A cross-sectional view showing an organic sensor according to some example embodiments,

[0184] Figure 6 A schematic diagram showing an example of a pixel array of an organic sensor according to some example embodiments,

[0185] Figure 7 A cross-sectional view showing an organic sensor according to some example embodiments,

[0186] Figure 8 A cross-sectional view showing an organic sensor according to some example embodiments,

[0187] Figure 9Cross-sectional view showing an organic sensor according to some example embodiments

[0188] Figure 10 Cross-sectional view showing an organic sensor according to some example embodiments

[0189] Figure 11 Cross-sectional view showing an organic sensor according to some example embodiments

[0190] Figure 12 Block diagram of a digital camera including an organic sensor according to some example embodiments

[0191] Figure 13 Schematic diagram showing an electronic device according to some embodiments, and

[0192] Figure 14 Graph showing the photoelectric conversion efficiency of the optoelectronic devices of Example 1 and Comparative Example 4 Detailed embodiments

[0193] Hereinafter, 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 should not be construed as limited to the example embodiments set forth herein.

[0194] In the drawings, for clarity, the thicknesses of layers, films, panels, regions, etc. are enlarged.

[0195] 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.

[0196] It will be understood that an element (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.

[0197] It will be understood that elements and / or their properties described herein as "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 the 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.

[0198] When the terms "about" or "substantially" are used in connection with a numerical value in this specification, it is intended that the relevant numerical value includes a tolerance of ±10% around the stated numerical value. When a range is specified, the range includes all values therebetween, e.g., increments of 0.1%.

[0199] In the drawings, for clarity of the embodiments, parts not relevant to the description are omitted, and throughout the specification, the same or similar constituent elements are denoted by the same reference numerals.

[0200] As used herein, "at least one of A, B, or C", "one of A, B, C, or combinations thereof", and "one of A, B, C and combinations thereof" refer to each of the constituent elements, and combinations thereof (e.g., A; B; C; A and B; A and C; B and C; or A, B, and C).

[0201] Hereinafter, "combination" includes mixing of two or more kinds, inter-substitution, and laminate structures of two or more kinds.

[0202] As used herein, when no specific definition is otherwise provided, "substituted" means that a hydrogen of a compound or functional group is replaced by a substituent selected from the following: a halogen atom (F, Br, Cl, or I), a hydroxyl group, 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 the same or different and are a hydrogen atom, a C1-C20 alkyl group, or a C6-C30 aryl 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 (-SiR 1 R 2 R 3 where R 1 -R 3is 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 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, and combinations thereof.

[0203] As used herein, when no specific definition is otherwise provided, "hetero" means including 1-4 heteroatoms selected from N, O, S, Se, Te, Si, and P.

[0204] As used herein, when no definition is otherwise provided, "aromatic ring" refers to a functional group as follows: wherein all atoms in the cyclic functional group have p-orbitals, and wherein these p-orbitals are conjugated, and "heteroaromatic ring" refers to an aromatic ring including heteroatoms. "Aromatic ring" refers to a C6-C30 aromatic hydrocarbon group, such as a C6-C20 aromatic hydrocarbon group or a C6-C30 aryl group, such as a C6-C20 aryl group. "Heteroaromatic ring" refers to a C3-C30 heteroaromatic hydrocarbon group, such as a C3-C20 heteroaromatic hydrocarbon group or a C6-C30 heteroaryl group, such as a C6-C20 heteroaryl group.

[0205] As used herein, "aromatic hydrocarbon group" refers to a hydrocarbon ring group having an aromatic ring, and includes monocyclic and polycyclic hydrocarbon ring groups, and the additional rings of the polycyclic hydrocarbon ring groups can be aromatic rings or non-aromatic rings. The aromatic hydrocarbon group can be a C6-C30 aromatic hydrocarbon group, a C6-C20 aromatic hydrocarbon group, or a C6-C10 aromatic hydrocarbon group. The heteroaromatic hydrocarbon group means an aromatic hydrocarbon group including 1 to 3 heteroatoms selected from N, O, S, P, and Si in the ring. The heteroaromatic hydrocarbon group can be a C3-C30 heteroaromatic hydrocarbon group, a C3-C20 heteroaromatic hydrocarbon group, or a C3-C10 heteroaromatic hydrocarbon group.

[0206] As used herein, when no definition is otherwise provided, "aryl" refers to a group including at least one hydrocarbon aromatic moiety, and can include: a group wherein all elements of the hydrocarbon aromatic moiety have p-orbitals forming conjugation, such as phenyl, naphthyl, etc.; a group wherein two or more hydrocarbon aromatic moieties can be connected by a σ bond, such as biphenyl, terphenyl, quaterphenyl, etc.; and a group wherein two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl. An aryl can include monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional groups.

[0207] 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 of the rings of the heteroaryl may have a heteroatom or each ring may have a heteroatom.

[0208] 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 a combination thereof. The aromatic ring is the same as described above, and the non-aromatic ring may be a C3-C30 cycloalkyl group, a C3-C30 cycloalkenyl group, or a C3-C30 cycloalkynyl group.

[0209] As used herein, when no other definition is provided, "halogen" may be one of F, Cl, Br, or I, and haloalkyl may be an alkyl group in which at least one hydrogen is replaced by a halogen and may be, for example, a perfluoroalkyl group such as -CF3.

[0210] Hereinafter, a near-infrared absorber according to some exemplary embodiments is described. The near-infrared absorber may be interchangeably referred to as a "near-infrared absorbing compound" herein.

[0211] The near-infrared absorber includes a compound represented by Chemical Formula 1.

[0212] [Chemical Formula 1]

[0213]

[0214] In Chemical Formula 1,

[0215] Ar is a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, or a combination thereof,

[0216] X 1 is O, S, Se, Te, S(=O), S(=O)2, NR a , CR b R c , SiR d R e , GeR f R g , CR h =CR i , or CR hh =CR ii (where R a , R b , R c , R d , R e , R f , R g , R h, and R i independently is hydrogen, deuterium, C1-C30 alkyl, C1-C30 haloalkyl, C6-C30 aryl, C6-C30 aryloxy, C3-C30 heteroaryl, halogen, cyano, or a combination thereof, R hh and R ii independently is (CH) where w is a positive integer w or at least one heteroatom of O, N, S, Se, or Te, and R hh and R ii are connected to each other to form an aromatic ring or a heteroaromatic ring),

[0217] X 2 is O, S, Se, Te, C, CR x -CR y , CR xx -CR yy , S(=O) or S(=O2) (where R x and R y independently is hydrogen, deuterium, C1-C30 alkyl, C1-C30 haloalkyl, C6-C30 aryl, C6-C30 aryloxy, C3-C30 heteroaryl, halogen, cyano, or a combination thereof, R xx and R yy independently is (CH) where v is a positive integer v or at least one heteroatom of O, N, S, Se, or Te, and R xx and R yy are connected to each other to form an aromatic ring or a heteroaromatic ring),

[0218] Ar 1 and Ar 2 independently is a heteroaromatic group including at least one heteroatom of O, S, Se, or Te,

[0219] Ar 3 and Ar 4 independently is a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, or a fused ring group thereof,

[0220] R 1 and R 2 independently is hydrogen, deuterium, halogen, cyano, nitro, hydroxy, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C10 aryl, or substituted or unsubstituted C3-C10 heteroaryl,

[0221] L 1 and L 2 independently is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NRa -, -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 are independently hydrogen, deuterium, a halogen, a cyano group, 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 are independently present or are linked to each other to form a separate ring, and for -(CR f R g ) n -, n is an integer of 1 or 2).

[0222] It is desirable that materials that absorb light in the long wavelength such as near-infrared light have a small HOMO-LUMO band gap energy, which is also referred to herein as a small band gap energy, a low band gap energy, etc. To have a small band gap energy, the conjugation length can be made longer, but when the conjugation length becomes longer, it is difficult to apply the deposition process. The near-infrared absorber represented by Chemical Formula 1 has the following donor-acceptor-donor structure: a core having an electron-withdrawing conjugated structure (the Ar-containing ring in Chemical Formula 1) is connected to an aromatic fused ring having an electron-donating property (Ar 1 -(including the ring containing N(R 1 ) and L 1 )-Ar 3 ) and (Ar 2 -(including the ring containing N(R 2 ) and L 2 )-Ar 4), and thus the near-infrared absorber has strong charge transfer characteristics and can effectively absorb light in the near-infrared wavelength region due to its low bandgap energy. In addition, the near-infrared absorber has improved thermal stability and is suitable for deposition processes. Therefore, the layer and / or structure including the near-infrared absorber can have improved sensitivity to light in the near-infrared wavelength region and / or light absorption rate (absorbance) in the near-infrared wavelength. A device (e.g., a sensor) configured to selectively absorb and / or convert (into an electrical signal, e.g., photoelectric conversion) near-infrared light can have improved performance and / or efficiency based on including the near-infrared absorber (e.g., in an active layer configured to selectively absorb and / or convert (into an electrical signal, e.g., photoelectric conversion) the near-infrared light).

[0223] Hereinafter, "a ring including N(R 1 ) and L 1 " may be referred to as "a ring containing N(R 1 )", and "a ring including N(R 2 ) and L 2 " may be referred to as "a ring containing N(R 2 )".

[0224] "A ring containing N(R 1 )" and "a ring including N(R 2 ) and L 2 " may be, depending on L 1 and L 2 , independently a pentagonal ring (e.g., a substituted or unsubstituted pyrrole ring), a hexagonal ring (e.g., a substituted or unsubstituted pyridine ring, a substituted or unsubstituted azine ring, a substituted or unsubstituted thiazine ring, a substituted or unsubstituted selenazine ring, or a substituted or unsubstituted pyrazine ring), or a heptagonal ring (e.g., a substituted or unsubstituted azepine ring).

[0225] 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.

[0226] 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.

[0227] In Chemical Formula 1, Ar may be a part of a group of moieties represented by Chemical Formula A-1, each moiety including at least one aromatic ring and left and right linking groups.

[0228] [Chemical Formula A-1]

[0229]

[0230] In Chemical Formula A-1,

[0231] the hydrogen of each aromatic ring may be replaced by a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, -SiH3, or a C1-C10 alkylsilyl group,

[0232] an adjacent pair of the individual * within the at least one aromatic ring is a connecting portion with a single corresponding one of the N-X-containing ring of Chemical Formula 1 1 -N or the N=X-containing ring of Chemical Formula 1 2 =N, and

[0233] the * of the left and right linking groups is a connecting portion connected with a single corresponding one of Ar of Chemical Formula 1 1 or Ar 2 of a single corresponding one.

[0234] In Chemical Formula 1, Ar may be a part of a group of parts represented by Chemical Formula A-2, and each part includes at least one aromatic ring and left and right linking groups.

[0235] [Chemical Formula A-2]

[0236]

[0237] In Chemical Formula A-2,

[0238] the hydrogen of each aromatic ring may be replaced by a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, -SiH3, or a C1-C10 alkylsilyl group,

[0239] an adjacent pair of the individual * within the at least one aromatic ring is a connecting portion with a single corresponding one of the N-X-containing ring of Chemical Formula 1 1 -N or the N=X-containing ring of Chemical Formula 1 2 =N, and

[0240] the * of the left and right linking groups is a connecting portion connected with a single corresponding one of Ar of Chemical Formula 1 1 or Ar 2 of a single corresponding one.

[0241] In Chemical Formula 1, when X 2 is CR xx -CR yy then R xx and R yyThey can be connected to each other to form an aromatic ring. In this way, when the aromatic ring is further fused, the absorption wavelength of the compound shifts to a longer wavelength, and the stability of the compound can be improved.

[0242] The aromatic ring can be 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; or 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.

[0243] The aromatic ring can be a part of a group of moieties represented by Chemical Formula B-1, and each moiety includes at least one aromatic ring.

[0244] [Chemical Formula B-1]

[0245]

[0246] In Chemical Formula B-1,

[0247] the hydrogen of each aromatic ring can be replaced by 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-C30 heteroaryl group (e.g., a C3-C20 heteroaryl group or a C3-C10 heteroaryl group), and

[0248] the * within the at least one aromatic ring is the connecting moiety to the carbon of CR xx -CR yy of.

[0249] The at least one aromatic ring can be a part of a group of moieties represented by Chemical Formula B-2, and each moiety includes at least one aromatic ring.

[0250] [Chemical Formula B-2]

[0251]

[0252] In Chemical Formula B-2,

[0253] The hydrogen of each aromatic ring may be replaced by a halogen, a cyano group, a C1-C30 alkyl group (for example, a C1-C20 alkyl group or a C1-C10 alkyl group), a C1-C30 alkoxy group (for example, a C1-C20 alkoxy group or a C1-C10 alkoxy group), a C1-C30 haloalkyl group (for example, a C1-C20 haloalkyl group or a C1-C10 haloalkyl group), -SiH3, a C1-C30 alkylsilyl group (for example, a C1-C20 alkylsilyl group or a C1-C10 alkylsilyl group), a C6-C30 aryl group (for example, a C6-C20 aryl group or a C6-C10 aryl group), a C6-C30 aryloxy group (for example, a C6-C20 aryloxy group or a C6-C10 aryloxy group), or a C3-C30 heteroaryl group (for example, a C3-C20 heteroaryl group or a C3-C10 heteroaryl group), and

[0254] the * within said at least one aromatic ring is a connecting moiety to the carbon of CR xx -CR yy moiety.

[0255] The aromatic ring may be a moiety represented by Chemical Formula B-3-1 or Chemical Formula B-3-2, each moiety including at least one aromatic ring.

[0256] [Chemical Formula B-3-1]

[0257]

[0258] [Chemical Formula B-3-2]

[0259]

[0260] In Chemical Formulas B-3-1 and B-3-2,

[0261] Ar 11 and Ar 12 are independently a substituted or unsubstituted C6-C30 aromatic hydrocarbon group or a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group.

[0262] In Chemical Formula B-3-1, Z 1 and Z 2 are independently CR a or N (wherein R ais hydrogen, deuterium, 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), -NH2, a C1-C30 alkylamine group (e.g., a C1-C20 alkylamine group or a C1-C10 alkylamine group), a C6-C30 arylamine group (e.g., a C6-C20 arylamine group or a C6-C10 arylamine 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), a C3-C30 heteroaryl group, a halogen, a cyano group, or a combination thereof, and

[0263] * within the at least one aromatic ring is the connecting moiety to the carbon of CR xx -CR yy of the carbon.

[0264] The moiety represented by Formula B-3-1 can be one moiety of a group of moieties represented by Formula B-3-11, each moiety including at least one aromatic ring.

[0265] [Formula B-3-11]

[0266]

[0267] In Formula B-3-11,

[0268] the hydrogen of each aromatic ring can be replaced by 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-C30 heteroaryl group (e.g., a C3-C20 heteroaryl group or a C3-C10 heteroaryl group), and

[0269] * within the at least one aromatic ring is the connecting moiety to the carbon of CR xx -CR yy of the carbon.

[0270] The moiety represented by Chemical Formula B-3-2 may be one of a group of moieties represented by Chemical Formula B-3-21, each moiety including at least one aromatic ring.

[0271] [Chemical Formula B-3-21]

[0272]

[0273] In Chemical Formula B-3-21,

[0274] the hydrogen of each aromatic ring may be replaced by 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-C30 heteroaryl group (e.g., a C3-C20 heteroaryl group or a C3-C10 heteroaryl group),

[0275] X a and X b are independently O, S, Se, Te, NR a , SiR b R c , or GeR d R e (wherein R a , R b , R c , R d , and R e are independently hydrogen, a halogen, a cyano group, a substituted or unsubstituted C1-C30 alkyl group (e.g., a C1-C20 alkyl group or a C1-C10 alkyl group), a substituted or unsubstituted C1-C30 alkoxy group (e.g., a C1-C20 alkoxy group or a C1-C10 alkoxy group), a substituted or unsubstituted C6-C30 aryl group (e.g., a C6-C20 aryl group or a C6-C10 aryl group), or a substituted or unsubstituted C6-C30 aryloxy group (e.g., a C6-C20 aryloxy group or a C6-C10 aryloxy group)), and

[0276] the * within the at least one aromatic ring is the connecting portion to the carbon of CR xx -CR yy .

[0277] For example, in Chemical Formulas B-3-11 and B-3-21, the halogen may be any one of F, Cl, Br, and I, and the haloalkyl may be an alkyl in which at least one hydrogen is replaced by a halogen, such as a perfluoroalkyl like -CF3.

[0278] In Chemical Formula 1, Ar 1 and Ar 2 are heteroatom-containing ring groups, and the heteroatoms included in the ring can enhance charge transfer properties and reduce the band gap energy. Additionally, the number of aromatic rings in Ar 1 and Ar 2 can be changed to easily adjust the absorption wavelength. Since the structure in which multiple aromatic rings are fused (Ar 1 -(including the ring containing N(R 1 ) and L 1 )-Ar 3 ) and (Ar 2 -(including the ring containing N(R 2 ) and L 2 )-Ar 4 ) provides a donor structure and thus increases the length of the conjugated structure, light with a long wavelength in the near-infrared region can be absorbed.

[0279] In Chemical Formula 1, Ar 1 and Ar 2 may be the same or different, and each may be represented by one of Chemical Formula C-1-1, Chemical Formula C-1-2, or Chemical Formula C-1-3, and Chemical Formula C-1-1, Chemical Formula C-1-2, or Chemical Formula C-1-3 each includes at least one aromatic ring.

[0280] [Chemical Formula C-1-1]

[0281]

[0282] [Chemical Formula C-1-2]

[0283]

[0284] [Chemical Formula C-1-3]

[0285]

[0286] In Chemical Formulas C-1-1 to C-1-3,

[0287] The hydrogen of each aromatic ring can be replaced by 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-C30 heteroaryl group (e.g., a C3-C20 heteroaryl group or a C3-C10 heteroaryl group).

[0288] Y 1 is O, S, Se, Te, S(=O), S(=O)2, NR a1 , SiR b1 R c1 , or GeR d1 R e1 (wherein R a1 , R b1 , R c1 , R d1 , and R e1 are 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),

[0289] Y 2 is O, S, Se, Te, S(=O), S(=O)2, NR a2 , SiR b2 R c2 , GeR d2 R e2 , or CR f2 R g2 (wherein R a2 , R b2 , R c2 , R d2 , R e2 , R f2 , and R g2independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3, C1-C10 alkylsilyl, -NH3, C1-C10 alkylamine, C6-C10 arylamine, C6-C14 aryl, C6-C14 aryloxy, C3-C12 heteroaryl, halogen, cyano, or a combination thereof,

[0290] 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 may exist independently or in combination with each other to form a spiro ring (eg, C4-C8 cycloalkyl, C5 cycloalkyl, or C6 cycloalkyl),

[0291] The at least one aromatic ring outside the * is the connection point with Ar of Chemical Formula 1, and

[0292] The * in the at least one aromatic ring is the same as that of Formula 1 including R 1 N(R 1 ) and the ring of formula 1 including R 2 N(R 2 )'s connecting part of the ring.

[0293] In Chemical Formula 1, Ar 1 and Ar 2 may be the same or different, and may each be represented by one of Chemical Formulas C-2-1 to C-2-4, each of which includes at least one aromatic ring.

[0294] [Chemical formula C-2-1]

[0295]

[0296] [Chemical formula C-2-2]

[0297]

[0298] [Chemical formula C-2-3]

[0299]

[0300] [Chemical formula C-2-4]

[0301]

[0302] In chemical formulas C-2-1 to C-2-4,

[0303] The hydrogen of each aromatic ring may be replaced by 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-C30 heteroaryl group (e.g., a C3-C20 heteroaryl group or a C3-C10 heteroaryl group).

[0304] Y 1 is O, S, Se, Te, S(=O), S(=O)2, NR a1 , SiR b1 R c1 , or GeR d1 R e1 (wherein R a1 , R b1 , R c1 , R d1 , and R e1 are 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),

[0305] R b1 and R c1 and R d1 and R e1 may independently exist or combine with each other to form a spiro ring (e.g., a C4-C8 cycloalkyl group, a C5 cycloalkyl group, or a C6 cycloalkyl group),

[0306] The * outside the at least one aromatic ring is the connection point to Ar of Formula 1, and

[0307] The * inside the at least one aromatic ring is the connection part to the N(R 1 )-containing ring including R 1 and the N(R 2 )-containing ring including R 2 ) of Formula 1.

[0308] In Formula 1, Ar 1 and Ar2 They may be the same or different, and each may be represented by one of Chemical Formulas C-3-1 to C-3-6, each of which includes at least one aromatic ring.

[0309] [Chemical Formula C-3-1]

[0310]

[0311] [Chemical Formula C-3-2]

[0312]

[0313] [Chemical Formula C-3-3]

[0314]

[0315] [Chemical Formula C-3-4]

[0316]

[0317] [Chemical Formula C-3-5]

[0318]

[0319] [Chemical Formula C-3-6]

[0320]

[0321] In Chemical Formulas C-3-1 to C-3-6,

[0322] the hydrogen of each aromatic ring may be replaced by a halogen, a cyano group, a C1-C30 alkyl group (for example, a C1-C20 alkyl group or a C1-C10 alkyl group), a C1-C30 alkoxy group (for example, a C1-C20 alkoxy group or a C1-C10 alkoxy group), a C1-C30 haloalkyl group (for example, a C1-C20 haloalkyl group or a C1-C10 haloalkyl group), -SiH3, a C1-C30 alkylsilyl group (for example, a C1-C20 alkylsilyl group or a C1-C10 alkylsilyl group), a C6-C30 aryl group (for example, a C6-C20 aryl group or a C6-C10 aryl group), a C6-C30 aryloxy group (for example, a C6-C20 aryloxy group or a C6-C10 aryloxy group), or a C3-C30 heteroaryl group (for example, a C3-C20 heteroaryl group or a C3-C10 heteroaryl group),

[0323] Y 1 is O, S, Se, Te, S(=O), S(=O)2, NR a1 , SiR b1 R c1 , or GeR d1 R e1 (where Ra1 , R b1 , R c1 , R d1 , and R e1 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3, C1-C10 alkylsilyl, -NH3, C1-C10 alkylamine group, C6-C10 arylamine group, C6-C14 aryl, C6-C14 aryloxy, C3-C12 heteroaryl, halogen, cyano, or a combination thereof),

[0324] Y 2 is O, S, Se, Te, S(=O), S(=O)2, NR a2 , SiR b2 R c2 , GeR d2 R e2 , or CR f2 R g2 (wherein R a2 , R b2 , R c2 , R d2 , R e2 , R f2 , and R g2 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3, C1-C10 alkylsilyl, -NH3, C1-C10 alkylamine group, C6-C10 arylamine group, C6-C14 aryl, C6-C14 aryloxy, C3-C12 heteroaryl, halogen, cyano, or a combination thereof),

[0325] 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 may independently exist or combine with each other to form a spiro ring (e.g., C4-C8 cycloalkyl, C5 cycloalkyl, or C6 cycloalkyl),

[0326] The * outside the at least one aromatic ring is the connection point to Ar of Formula 1, and

[0327] The * inside the at least one aromatic ring is to the ring containing N(R 1 ) of Formula 1 including R 1 and to the ring containing N(R 2 ) of Formula 1 including R 2The connecting part of the ring of ().

[0328] In Chemical Formula 1, Ar 1 and Ar 2 may be the same or different, and each may be represented by one of Chemical Formulas C-4-1 and C-4-2, and each of Chemical Formulas C-4-1 and C-4-2 includes at least one aromatic ring.

[0329] [Chemical Formula C-4-1]

[0330]

[0331] [Chemical Formula C-4-2]

[0332]

[0333] In Chemical Formulas C-4-1 and C-4-2,

[0334] the hydrogen of each aromatic ring may be replaced by 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.

[0335] Y 1 is O, S, Se, Te, S(=O), S(=O)2, NR a1 , SiR b1 R c1 , or GeR d1 R e1 (wherein R a1 , R b1 , R c1 , R d1 , and R e1 are 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).

[0336] Y 2 is O, S, Se, Te, S(=O), S(=O)2, NR a2 , SiR b2 R c2 , GeR d2 R e2 , or CR f2 R g2 (wherein R a2 , R b2 , Rc2 , R d2 , R e2 , R f2 , and R g2 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3, C1-C10 alkylsilyl, -NH3, C1-C10 alkylamine group, C6-C10 arylamine group, C6-C14 aryl, C6-C14 aryloxy, C3-C12 heteroaryl, halogen, cyano, or a combination thereof),

[0337] 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 may independently exist or combine with each other to form a spiro ring,

[0338] The * outside the at least one aromatic ring is the connection point to Ar of Formula 1, and

[0339] The * inside the at least one aromatic ring is the connection part to the ring containing N(R 1 ) of Formula 1 and the ring containing N(R 1 ) of Formula 1 that includes R 2 . 2 )

[0340] In Formula 1, Ar 1 and Ar 2 may be the same or different, and may each be represented by one of Formulas C-5-1 to C-5-8, and each of Formulas C-5-1 to C-5-8 includes at least one aromatic ring.

[0341]

[0342] In Formulas C-5-1 to C-5-8,

[0343] The hydrogen of each aromatic ring may be replaced by 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-C30 heteroaryl group (e.g., a C3-C20 heteroaryl group or a C3-C10 heteroaryl group).

[0344] Y 1 is O, S, Se, Te, S(=O), S(=O)2, NR a1 , SiR b1 R c1 , or GeR d1 R e1 (wherein R a1 , R b1 , R c1 , R d1 , and R e1 are 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),

[0345] Y 2 and Y 3 are independently O, S, Se, Te, S(=O), S(=O)2, NR a2 , SiR b2 R c2 , GeR d2 R e2 , or CR f2 R g2 (wherein R a2 , R b2 , R c2 , R d2 , R e2 , R f2 , and R g2independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3, C1-C10 alkylsilyl, -NH3, C1-C10 alkylamine, C6-C10 arylamine, C6-C14 aryl, C6-C14 aryloxy, C3-C12 heteroaryl, halogen, cyano, or a combination thereof,

[0346] 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 may exist independently or in combination with each other to form a spiro ring (eg, C4-C8 cycloalkyl, C5 cycloalkyl, or C6 cycloalkyl),

[0347] The at least one aromatic ring outside the * is the connection point with Ar of Chemical Formula 1, and

[0348] The * in the at least one aromatic ring is the same as that of Formula 1 including R 1 N(R 1 ) and the ring of formula 1 including R 2 N(R 2 )'s connecting part of the ring.

[0349] The near infrared absorber can absorb light in the near infrared wavelength region. The near infrared absorber can have, for example, a peak absorption wavelength (λ) of about 750 nm or more, about 770 nm or more, about 780 nm or more, about 790 nm or more, about 800 nm or more, about 810 nm or more, about 820 nm or more, or about 830 nm or more. 最大 The near infrared absorber may have a peak absorption wavelength (λ) of, for example, about 750 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. 最大 ).

[0350] The near-infrared absorber can exhibit good charge transfer characteristics, and thus, it has photoelectric conversion characteristics of absorbing (e.g., selectively absorbing) light and / or converting it (e.g., photoelectrically converting it) into an electrical signal well, and thus can be effectively used as a photoelectric conversion material for optoelectronic devices. Therefore, (e.g., in the active layer and / or charge assisting layer of an optoelectronic device (e.g., in the active layer 30 shown in Figure 1 and 2 and / or in the charge assisting layers 40 and 45 shown in Figure 2 )) an optoelectronic device including the near-infrared absorber can have improved operating performance and / or efficiency based on including the near-infrared absorber, e.g., have improved operating performance and / or efficiency in realizing the photoelectric conversion of incident near-infrared light.

[0351] The near-infrared absorber has good heat resistance, and thus can prevent or reduce thermal decomposition during deposition, and thus can 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 400 °C, e.g., less than or equal to about 390 °C, less than or equal to about 380 °C, or less than or equal to about 370 °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 400 °C.

[0352] Some example embodiments provide a near-infrared absorption / blocking (absorbing and / or blocking) film including the near-infrared absorber.

[0353] The near-infrared absorption / blocking film can be applied to various fields that require light absorption characteristics in the near-infrared wavelength region.

[0354] The near-infrared absorber has both light absorption characteristics and photoelectric characteristics in the near-infrared wavelength region, and thus it can be effectively used as a photoelectric conversion material.

[0355] Figure 1 is a cross-sectional view of an optoelectronic device according to some example embodiments.

[0356] Referring to 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 disposed between the first electrode 10 and the second electrode 20.

[0357] A substrate (not shown) may be provided on one side of the first electrode 10 or the second electrode 20. The substrate may be made of, for example, (e.g., may at least partially include) 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 substrate may be omitted.

[0358] 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 may be a cathode, and the second electrode 20 may be an anode.

[0359] At least one of the first electrode 10 and 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 / or fluorine-doped tin oxide (FTO), or a single-layer or multi-layer thin metal layer. When one of the first electrode 10 and 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.

[0360] The active layer 30 is a layer including a p-type semiconductor and an n-type semiconductor configured to provide a pn junction, and it is a layer capable of generating excitons by receiving light from the outside (e.g., outside the active layer 30) and then separating holes and electrons from the generated excitons.

[0361] The p-type semiconductor and the n-type semiconductor may independently be light-absorbing materials configured to absorb (e.g., selectively absorb) light in at least a part of a wavelength region, and the above-mentioned near-infrared absorber may be a p-type semiconductor or an n-type semiconductor. For example, the above-mentioned near-infrared absorber may be used for the p-type semiconductor, and may include fullerenes or fullerene derivatives as the n-type semiconductor. Therefore, it will be understood that the active layer 30 may at least partially include the above-mentioned near-infrared absorber (e.g., may include the near-infrared absorber and fullerenes or fullerene derivatives). Additionally, it will be understood that the active layer 30 may have a peak absorption wavelength (λ) of, for example, greater than or equal to about 750 nm, greater than or equal to about 770 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. 最大), or a peak absorption wavelength (λ) of from about 750 nm to about 3000 nm, from about 750 nm to about 2500 nm, from about 780 nm to about 2200 nm, from about 790 nm to about 2100 nm, from about 800 nm to about 2000 nm, from about 810 nm to about 2000 nm, from about 820 nm to about 2000 nm, or from about 830 nm to about 2000 nm 最大 ). The active layer 30 and thus the optoelectronic device 100 can have improved near-infrared light absorption characteristics (e.g., can have improved sensitivity to light in the near-infrared wavelength region, improved light absorption rate in the near-infrared wavelength region, etc.) based on the active layer including the above near-infrared absorber, and thus improved photoelectric conversion performance and / or efficiency and / or improved thermal stability. In some example embodiments, the active layer 30 can be a near-infrared absorption / blocking film including the near-infrared absorber.

[0362] The active layer 30 can include an intrinsic layer in which the above near-infrared absorber (e.g., p-type semiconductor) and fullerene or fullerene derivative (e.g., n-type semiconductor) are co-deposited. Here, the p-type semiconductor and the n-type semiconductor can be included in a volume ratio of from about 1:9 to about 9:1, such as from about 2:8 to about 8:2, from about 3:7 to about 7:3, from about 4:6 to about 6:4, or about 5:5.

[0363] In addition to the intrinsic layer, the active layer 30 can further include a p-type layer and / or an n-type layer. The p-type layer can include the above near-infrared absorber (e.g., p-type semiconductor), and the n-type layer can include the above n-type semiconductor. For example, they can be included in various combinations such as p-type layer / I layer, I layer / n-type layer, p-type layer / I layer / n-type layer, etc.

[0364] The optoelectronic device 100 can further include a secondary layer between the first electrode 10 and the active layer 30 and / or between the second electrode 20 and the active layer 30. The secondary layer can be a charge assisting layer or an optical assisting layer.

[0365] The optoelectronic device (e.g., optoelectronic device) is shown in Figure 2 ).

[0366] Figure 2 is a cross-sectional view showing an optoelectronic device according to some example embodiments.

[0367] Refer 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 exemplary embodiments, only one of the first auxiliary layer 40 or the second auxiliary layer 45 is included in the optoelectronic device 200.

[0368] The first auxiliary layer 40 and the second auxiliary layer 45 may each be a charge assisting layer, which may make the holes and electrons separated in the active layer 30 easier to transport to improve the efficiency of the optoelectronic device 200.

[0369] The charge assisting layer 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.

[0370] The charge assisting layer 40 and / or 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.

[0371] The charge assisting layers 40 and 45 may include, for example, the above-mentioned near-infrared absorber. In some exemplary embodiments, the charge assisting layer 40 and / or 45 may include the above-mentioned near-infrared absorber, and the active layer 30 may also include the above-mentioned near-infrared absorber. In some exemplary embodiments, the charge assisting layer 40 and / or 45 may include the above-mentioned near-infrared absorber, and the active layer 30 may not include the above-mentioned near-infrared absorber. The charge assisting layer 40 and / or 45 and thus the optoelectronic device 200 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 photoelectric conversion performance and / or efficiency, and / or improved thermal stability based on the charge assisting layer 40 and / or 45 including the above-mentioned near-infrared absorber.

[0372] The optical auxiliary layer may be disposed in the light incident direction of the optoelectronic device. For example, when the second electrode 20 is a light receiving electrode (e.g., an electrode close to the surrounding environment from which the optoelectronic device 200 receives light), the optical auxiliary layer may be disposed on the active layer 30. For example, the optical auxiliary layer may be disposed between the second electrode 20 and the active layer 30.

[0373] The optoelectronic devices 100 and 200 may further include an antireflection layer 47 on one surface of the first electrode 10 or the second electrode 20. The antireflection layer 47 is disposed on the light incident side and reduces the light reflectance of the incident light, and thereby, the light absorption rate is further improved. For example, when light enters from the first electrode 10, the antireflection layer 47 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.

[0374] The antireflection layer 47 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 metal sulfide, or an organic material having a refractive index within the range. The antireflection layer 47 may include, for example, a metal oxide or a chalcogenide oxide such as an aluminum-containing oxide, a molybdenum-containing oxide, a tungsten-containing oxide, a vanadium-containing oxide, a rhenium-containing oxide, a niobium-containing oxide, a tantalum-containing oxide, a titanium-containing oxide, a nickel-containing oxide, a copper-containing oxide, a cobalt-containing oxide, a manganese-containing oxide, a chromium-containing oxide, a 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.

[0375] In the optoelectronic devices 100 and 200, when light enters the optoelectronic devices 100 and / or 200 and thereby enters its 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 of the first electrode 10 and the second electrode 20, such that a current flows (e.g., is caused, generated, etc.).

[0376] The optoelectronic devices 100 and 200 may be applied to solar cells, image sensors, photodetectors, photosensors, and organic light emitting diodes (OLEDs) (e.g., included therein), but the exemplary embodiments are not limited thereto.

[0377] The 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.

[0378] In some example embodiments, the optoelectronic device 100 may include the near-infrared absorber in any of its elements (in addition to or as an alternative to the active layer 30, including one or more of the first electrode 10 or the second electrode 20). In some example embodiments, the optoelectronic device 200 may include the near-infrared absorber in any of its elements (in addition to or as an alternative to one or more of the active layer 30 and / or the charge-assist layer 40 / 45, including one or more of the first electrode 10 or the second electrode 20).

[0379] Figure 3 FIG. is a cross-sectional view showing an organic sensor according to some example embodiments.

[0380] An organic sensor 300 according to some example embodiments includes a semiconductor substrate 110, an insulating layer 80, and an optoelectronic device 100.

[0381] The semiconductor substrate 110 may be a silicon substrate and may integrate 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 described later, and the information of the charge memory 55 may be transmitted by the transfer transistor.

[0382] 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 alloys thereof, but are not limited thereto. In addition, it is not limited to the above structure, and the metal lines and pads may be disposed under the semiconductor substrate 110.

[0383] 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 / or SiOF. The insulating layer 80 has a channel 85 that exposes the charge memory 55. The channel 85 may be filled with a filler.

[0384] The above-described 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 a 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.

[0385] Both the first electrode 10 and the second electrode 20 may be transparent electrodes, and the active layer 30 may be as described above with reference to Figure 1 and2 The same as described. The active layer 30 can selectively absorb light in the near-infrared wavelength region. 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. As referred to above Figure 1 in the annotation, the active layer 30 can include the above-mentioned near-infrared absorber, and thus can 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.

[0386] A focusing lens (not shown) can be further formed on the optoelectronic device 100. The focusing lens can control the direction of incident light and focus the light in one area. The focusing lens can have a shape such as a cylinder or a hemisphere, but is not limited thereto.

[0387] Although Figure 3 is described Figure 1 for the organic sensor to which the optoelectronic device 100 is applied, but according to Figure 2 the optoelectronic device 200 can be similarly applied (e.g., instead of the optoelectronic device 100 being included in the organic sensor 300).

[0388] The organic sensor according to some example embodiments can be an organic infrared light sensor, such as an iris sensor or a depth sensor.

[0389] The iris sensor identifies a person by: using the unique iris characteristics of each person, and particularly by taking an image of the user's eye at an appropriate distance, processing the image, and comparing it with his / her stored image.

[0390] The depth sensor identifies the shape and position of an object from its three-dimensional information by: taking an image of the object at an appropriate distance from the user and processing the image. The depth sensor can be used as, for example, a face recognition sensor.

[0391] Figure 4 FIG. shows a cross-sectional view of an organic sensor according to some example embodiments.

[0392] The organic sensor according to some example embodiments can include a plurality of sensors having different functions. For example, at least one of the plurality of sensors having different functions can be a biometric sensor, and the biometric sensor can 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 can be an iris sensor, and another sensor of the plurality of sensors having different functions can be a depth sensor.

[0393] 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 having a first wavelength (λ1) in the infrared wavelength region. 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 (e.g., an infrared wavelength region that is the same as or different from the infrared wavelength region including the first wavelength (λ1)) having a second wavelength (λ2) in the infrared wavelength region.

[0394] The first wavelength (λ1) and the second wavelength (λ2) may be different, for example, in a wavelength region from 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.

[0395] For example, one of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region from 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 greater than about 900 nm and less than or equal to about 1000 nm.

[0396] For example, one of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region from 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 from about 910 nm to about 970 nm.

[0397] For example, one of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region from 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 from about 930 nm to about 950 nm.

[0398] For example, one of the first wavelength (λ1) or the second wavelength (λ2) may belong to a wavelength region from 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 from about 935 nm to about 945 nm.

[0399] 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.

[0400] 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, overlapping in a vertical direction perpendicular to the top surface 110S of the semiconductor substrate 110.

[0401] 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 a first wavelength (λ1) (e.g., light in the infrared wavelength region) and infrared light including a second wavelength (λ2), and may block and / or absorb other light. Herein, other light may include light in the ultraviolet (UV) and visible regions.

[0402] The first infrared light sensor 100A includes a first electrode 10, an active layer 30, and a second electrode 20. As Figure 4 shown, the first infrared light sensor 100A may be the same as an optoelectronic device 100 according to some example embodiments of the example embodiments described including reference Figure 1 description, but it will be understood that in some example embodiments, the first infrared light sensor 100A may be the same as an optoelectronic device 200 according to some example embodiments of the example embodiments described including reference Figure 2 description.

[0403] 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 a 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, a charge memory 55, and a transfer transistor (not shown).

[0404] 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 a transmission 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, a separate filter for wavelength selectivity of the light entering the second infrared light sensor 120 is not separately required. However, when all infrared light in a specific (or alternatively predetermined) region including the first wavelength (λ1) is not 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.

[0405] Accordingly, in the organic sensor 400, the first infrared light sensor 100A may be understood as an optoelectronic device (e.g., optoelectronic devices 100 and / or 200) configured to sense (e.g., selectively absorb and / or convert (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 120 may be understood as another sensor configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in a separate wavelength region (e.g., the 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.

[0406] The organic sensor according to some example embodiments may include two infrared light sensors that separately perform separate functions, and thus may 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 performed by the pixel for each sensor is doubled, and as a result, the sensitivity may be greatly improved.

[0407] As referred to above Figure 1Annotated, the active layer 30, or any part of the optoelectronic device 100 and / or 200 may include the above-mentioned near-infrared absorber, and thus may 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 thus may 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.

[0408] Figure 5 A cross-sectional view showing an example of an organic sensor according to some example embodiments.

[0409] According to some example embodiments, the organic sensor may be an organic CMOS image sensor.

[0410] Reference Figure 5 , according to some example embodiments, the organic sensor 500 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 charge memories 55, a lower insulating layer 60, color filter layers 70a, 70b, and 70c, an upper insulating layer 80, and an optoelectronic device 100.

[0411] The semiconductor substrate 110 may be integrated with photosensing devices 50a, 50b, and 50c, transfer transistors (not shown), and charge memories 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) that may be configured to sense (e.g., selectively absorb and / or convert (convert to an electrical signal, e.g., photoelectric conversion)) light in different visible wavelength regions.

[0412] The photosensing devices 50a, 50b, and 50c, transfer transistors, and / or charge memories 55 may be integrated in each pixel. For example, the photosensing device 50a may be included in a red pixel, the photosensing device 50b may be included in a green pixel, and the photosensing device 50c may be included in a blue pixel.

[0413] The photosensing devices 50a, 50b, and 50c sense (e.g., selectively absorb and / or convert (e.g., convert into an electrical signal, such as photoelectric conversion)) incident light, and the information sensed by the photosensing devices can be transmitted by the transfer transistors. The charge memory 55 is electrically connected to the optoelectronic device 100, and the information of the charge memory 55 can be transmitted by the transfer transistors.

[0414] Metal lines (not shown) and pads (not shown) are formed on the semiconductor substrate 110. To reduce signal delay, the metal lines and pads can 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 can be disposed under the photosensing devices 50a and 50b.

[0415] The lower insulating layer 60 is formed on the metal lines and pads. The lower insulating layer 60 may include the same or different material compositions as the insulating layer 80.

[0416] The color filters 70a, 70b, and 70c are formed on the lower insulating layer 60. The color filters 70a, 70b, and 70c include a blue filter 70a formed in a blue pixel, a red filter 70b formed in a red pixel, and a green filter 70c formed in a green pixel.

[0417] An insulating layer (also referred to as an upper insulating layer) 80 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.

[0418] The above-described 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 as an example in the figure, 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.

[0419] 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) may include the above-described near-infrared absorber.

[0420] Incident light from one 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.

[0421] As referred to above Figure 1 annotated, the active 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.

[0422] 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, e.g., 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, e.g., photoelectric conversion) light in a separate visible wavelength region (e.g., red, blue, and / or green light).

[0423] Figure 6 A schematic diagram showing an example of a pixel array of an organic sensor according to some example embodiments.

[0424] Reference Figure 6 , an organic sensor 600 according to some example embodiments includes a plurality of pixels PX, and the plurality of pixels PX can have a matrix array that is repeatedly arranged along rows and columns. The plurality of pixels PX can form ( "at least partially include") a unit pixel group A of a 2x2 array of pixels as shown in, for example Figure 6 . However, the arrangement of the pixels is not limited thereto, but is variously modified, and in addition to the 2x2 array, the unit pixel group A can be variously modified into different pixel arrays, including 3x3 arrays, 4x4 arrays, etc.

[0425] At least a portion of the pixel may include a plurality of sensors with different functions within one pixel, and the plurality of sensors may be stacked therein. In some example embodiments, each pixel PX may include two or more organic sensors configured to sense (e.g., absorb) light in different wavelength regions (the "wavelength spectrum of light") relative to each other, and the organic sensors configured to sense light in different wavelength regions may be stacked in a direction perpendicular (e.g., perpendicular within manufacturing tolerances and / or material tolerances) to the top surface 110S of the substrate of the organic sensor 600, as shown in at least Figure 7 (e.g., the y direction). Here, light in different wavelength regions may be selected from: the visible wavelength region; the infrared wavelength region including the near-infrared wavelength region; and the ultraviolet (UV) wavelength region.

[0426] It will be understood that any organic sensor according to any example embodiment herein may have the pixel array structure of the organic sensor 600 as shown in Figure 6 .

[0427] Figure 7 FIG. is a cross-sectional view showing an organic sensor according to some example embodiments.

[0428] Referring to Figure 7 , an organic sensor 700 according to some example embodiments includes a semiconductor substrate 110 integrated with a visible light sensor 50 including photosensing devices 50a and 50b, a transfer transistor (not shown), and / or a charge memory 55; a lower insulating layer 60; a color filter layer 70; an insulating layer 80 (also referred to as an upper insulating layer when present in the same organic sensor as the lower insulating layer 60); and an optoelectronic device 100.

[0429] The semiconductor substrate 110 may be a silicon substrate and is integrated with photosensing devices 50a and 50b, a transfer transistor (not shown), and a charge memory 55. The photosensing devices 50a and 50b may be photodiodes (e.g., silicon-based photodiodes).

[0430] The photosensing devices 50a and 50b may sense light, and 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, and the information of the charge memory 55 may be transmitted by the transfer transistor.

[0431] 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 with 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 this structure, and the metal lines and pads may be disposed below the photosensing devices 50a and 50b.

[0432] The lower insulating layer 60 is formed on the metal line and the pad. The lower insulating layer 60 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 lower insulating layer 60 has a channel exposing the charge memory 55. The channel may be filled with a filler.

[0433] The color filter layer 70 is formed on the lower insulating layer 60. The color filter layer 70 includes a blue color filter 70a formed in a blue pixel and a red color filter 70b formed in a red pixel. In Figure 7 the example embodiment shown, a green color filter is not included, but a green color filter may be further included.

[0434] The insulating layer 80 is formed on the color filter layer 70. The insulating layer 80 eliminates the steps caused by the color filter layer 70 and planarizes the surface. The insulating layer 80 and the lower insulating layer 60 may include contact holes (not shown) exposing the pad and vias (e.g., channels 85) exposing the charge memory 55 of the green pixel.

[0435] The optoelectronic device 100 is formed on the insulating layer 80. The optoelectronic device 100 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. The optoelectronic device 100 may be the same as Figure 1 the optoelectronic device 100. In some example embodiments, Figure 7 the optoelectronic device 100 may be replaced by Figure 2 the optoelectronic device 200.

[0436] Both the first electrode 10 and the second electrode 20 may be light-transmissive electrodes, and the active layer 30 may selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in the near-infrared wavelength region. In some example embodiments including Figure 7 the example embodiment shown, the active layer 30 may additionally selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in the visible wavelength region (e.g., green light).

[0437] 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 one area. The focusing lens may have a shape such as a cylinder or a hemisphere, but is not limited thereto.

[0438] In Figure 7In [the figure], a structure is described in which a photoelectric device 100 that selectively absorbs light in the near-infrared wavelength region is stacked on a semiconductor substrate 110, but the present disclosure is not limited thereto. Among the light incident on the organic sensor 700 at the top surface of the photoelectric device 100, at least the light in the near-infrared wavelength region can be mainly absorbed in the active layer 30 and be photoelectrically converted, and the light in the visible (e.g., blue, green, and / or red) wavelength region can pass through the first electrode 10 and be sensed by the light sensing devices 50a and 50b.

[0439] Figure 8 FIG. is a cross-sectional view showing an organic sensor according to some example embodiments.

[0440] Reference Figure 8 , according to some example embodiments, an organic sensor 800 includes a visible light sensor 50 and the photoelectric device 100 as described above.

[0441] Reference Figure 8 , in an organic sensor 800 according to some example embodiments, the visible light sensor 50 can be a combination of a photodiode integrated in the semiconductor substrate 110 and a photoelectric device disposed on the semiconductor substrate 110, and the photoelectric device 100 can be a separate (individual) photoelectric device.

[0442] Therefore, in the case where an organic sensor includes a photoelectric device (e.g., 100) that includes the near-infrared absorber and is configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in a first near-infrared wavelength region and another sensor (e.g., 50a and / or 50b) that is configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in a separate wavelength region of the incident light, the organic sensor can further include another photoelectric device (e.g., 50c) on the semiconductor substrate, the another photoelectric device being between the photoelectric device 100 and the semiconductor substrate 110, the another photoelectric device being configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in another wavelength region of the incident light, the another wavelength region of the incident light being different from the first near-infrared wavelength region and different from the separate wavelength regions absorbed by the another sensors 50a and / or 50b.

[0443] In the semiconductor substrate 110, a blue light sensing device 50a, a red light sensing device 50b, a charge memory 55, and a transfer transistor (not shown) are integrated. The blue light sensing device 50a and the red light sensing device 50b are photodiodes (e.g., silicon-based photodiodes) and are spaced apart from each other in the horizontal direction of the semiconductor substrate 110. The blue light sensing device 50a is integrated in a blue pixel, and the red light sensing device 50b is integrated in a red pixel.

[0444] On a semiconductor substrate 110, a lower insulating layer 60 and a color filter layer 70 are formed. The color filter layer 70 includes a blue color filter 70a overlapping with the blue light sensing device 50a and a red color filter 70b overlapping with the red light sensing device 50b.

[0445] 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 a through hole (e.g., a channel 85) exposing the charge memory 55. The through hole (e.g., the channel 85) may be filled with a filler. At least one of the lower insulating layer 60 or the intermediate insulating layer 65 may be omitted.

[0446] On the intermediate insulating layer 65, another optoelectronic device 850 is formed. In Figure 8 the example embodiment shown, the another optoelectronic device 850 is also a green sensor 50c, but it will be understood that in some example embodiments, the another optoelectronic device 850 may be configured to sense (e.g., selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion)) light in a wavelength region as follows: which is different from the green wavelength region and may be a non-visible wavelength region (e.g., a second near-infrared wavelength region) different from the first near-infrared wavelength region sensed by the optoelectronic device 100. The another optoelectronic device 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 an anode and the other is a cathode.

[0447] Both the first electrode 101 and the second electrode 102 may be light-transmissive electrodes, and the light-transmissive electrodes may be made of a transparent conductor such as indium tin oxide (ITO) or indium zinc oxide (IZO) in some example embodiments, or may be a thin metal layer with a thickness of several nanometers to several tens of nanometers or a thin metal layer doped with a metal oxide with a thickness of several nanometers to several tens of nanometers.

[0448] The active layer 103 may have a composition similar to that of the active layer 30 of the optoelectronic device 100 and / or 200, and may include the near-infrared absorber. The active layer 103 may be a photoelectric conversion layer configured to selectively absorb and / or convert (into an electrical signal, such as photoelectric conversion) light in at least a part of the wavelength region (e.g., the wavelength spectrum of light). The active layer 103 may, for example, convert at least a part of 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 any combination thereof, etc., into an electrical signal.

[0449] For example, the active layer 103 may be configured to selectively absorb and / or convert (into an electrical signal, such as photoelectric conversion) at least one of green light, blue light, red light, infrared light, or ultraviolet light. In this context, the selective absorption of at least one of green light, blue light, red light, infrared light, or ultraviolet light means that the light absorption spectrum has a peak absorption wavelength (λ 最大 ) within one of approximately 500 nm to approximately 600 nm, greater than or equal to approximately 380 nm and less than approximately 500 nm, greater than approximately 600 nm and less than or equal to approximately 700 nm, and greater than approximately 700 nm and less than or equal to approximately 3000 nm, and the light absorption spectrum within the corresponding wavelength region is significantly higher than the light absorption spectrum within other wavelength regions.

[0450] The active layer 103 may include at least one p-type semiconductor and at least one n-type semiconductor that form a pn junction, and may generate excitons by 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 independently be light absorption materials, and for example, at least one of the p-type semiconductor or the n-type semiconductor may be an organic light absorption material. For example, at least one of the p-type semiconductor or the n-type semiconductor may be a wavelength-selective light absorption material that selectively absorbs light in a specific (or alternatively predetermined) wavelength region, and for example, at least one of the p-type semiconductor or the n-type semiconductor may be a wavelength-selective organic light absorption material. The p-type semiconductor and the n-type semiconductor may have peak absorption wavelengths (λ 最大 ) within the same wavelength region or different wavelength regions among the green wavelength region, blue wavelength region, red wavelength region, and infrared wavelength region. For example, the p-type semiconductor may be an organic material having a core structure including an electron-donating part, a π-conjugated linking group, and an electron-accepting part. The p-type semiconductor may be represented, for example, by Chemical Formula 2, but is not limited thereto.

[0451] [Chemical Formula 2]

[0452] EDG-HA–EAG

[0453] In Chemical Formula 2, HA may be a C2-C30 heterocyclic group having 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, the p-type semiconductor represented by Chemical Formula 2 may be represented by Chemical Formula 2A, for example.

[0454] [Chemical Formula 2A]

[0455]

[0456] In Chemical Formula 2A, X may be S, Se, Te, SO, SO2, or SiR a R b , Ar may be a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heterocyclic group, or a fused ring of two or more of the foregoing, Ar 1a and Ar 2a may independently be a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group, Ar 1a and Ar 2a may independently exist alone or may be connected to each other to form a fused ring, and R 1a -R 3a 、R a 、and R b 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.

[0457] For example, in Chemical Formula 2A, Ar 1a and Ar 2a may independently be one of the following: a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyridazinyl 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 naphthyridinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted benzotriazinyl group, a substituted or unsubstituted pyridopyrazinyl group, a substituted or unsubstituted pyridopyrimidinyl group, and a substituted or unsubstituted pyridopyridazinyl group. For example, Ar 1a and Ar 2a in Chemical Formula 2A may be connected to each other to form a ring, or for example, Ar 1a and Ar 2aIt can be connected to each other through a single bond, -(CR g R h ) n2 -(where n2 is 1 or 2), -O-, -S-, -Se-, -N=, -NR i -, -SiR j R k -, or -GeR l R m - to form a ring. Herein, R g -R m can independently be hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C1-C6 alkoxy, halogen, or cyano.

[0458] For example, the p-type semiconductor represented by Chemical Formula 2 can be represented by Chemical Formula 2B, for example.

[0459] [Chemical Formula 2B]

[0460]

[0461] In Chemical Formula 2B, X 1 can be Se, Te, O, S, SO, or SO2, Ar 3 can be substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heterocyclic group, or a fused ring of two or more of the foregoing, R 1 -R 3 can independently be one of the following: hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, halogen, cyano, cyano-containing group, or a combination thereof, G can be one of the following: 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 ))-, or SnR o R p , where R f 、R g 、R h 、R i 、R j 、R k 、Rl , R m , R n , R o , and R p can independently be one of the following: hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, and substituted or unsubstituted C6-C12 aryl, R f and R g , R i and R j , R k and R l , R m and R n , as well as R o and R p can independently exist alone or can be connected to each other to provide a ring, and k can be 1 or 2, R 6a -R 6d and R 7a -R 7d can independently be one of the following: hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, halogen, cyano, cyano-containing group, or a combination thereof, R 6a -R 6d can independently exist alone or two adjacent ones thereof can be connected to each other to form a fused ring, and R 7a -R 7d can independently exist alone or two adjacent ones thereof can be connected to each other to form a fused ring.

[0462] For example, Ar of Chemical Formula 2B 3 can be a benzene ring, a naphthalene ring, an anthracene ring, a thiophene ring, a selenophene ring, a tellurophene ring, a pyridine ring, a pyrimidine ring, or a fused ring of two or more of the foregoing. The n-type semiconductor can be, for example, fullerene or a fullerene derivative, but is not limited thereto.

[0463] The active layer 103 may be an intrinsic layer (I layer), where the p-type semiconductor and the n-type semiconductor are blended as a bulk heterojunction. Here, the p-type semiconductor and the n-type semiconductor may be blended at a volume ratio of about 1:9 to about 9:1, such as 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. The active layer 103 may include a bilayer, which includes a p-type layer containing the above p-type semiconductor and an n-type layer including the above n-type semiconductor. Here, the thickness ratio of the p-type layer to the n-type layer may be about 1:9 to about 9:1, such as 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. In addition to the intrinsic layer, the active layer 103 may further include a p-type layer and / or an n-type layer. The p-type layer may include the above p-type semiconductor, and the n-type layer may include the above n-type semiconductor. For example, they may be included in various combinations such as p-type layer / I layer, I layer / n-type layer, p-type layer / I layer / n-type layer, etc.

[0464] In Figure 8 the example embodiment shown, the active layer 103 is configured to selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) green light, but the example embodiment is not limited thereto, and in some example embodiments, the active layer 103 may selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) blue light, red light, or light in any visible wavelength region, or light in any non-visible wavelength region (e.g., near-infrared light in a second wavelength region selectively transmitted by the optoelectronic device 100).

[0465] Figure 9 FIG. is a cross-sectional view showing an organic sensor according to some example embodiments.

[0466] Refer to Figure 9 , an organic sensor 900 according to some example embodiments includes a visible light sensor 50 and an optoelectronic device 100 similar to the organic sensor in some example embodiments. The visible light sensor 50 includes a blue light sensing device 50a and a red light sensing device 50b integrated in a semiconductor substrate 110, and another optoelectronic device 850, where the another optoelectronic device 850 includes a green sensor 50c disposed on the semiconductor substrate 110, and the blue light sensing device 50a and the red light sensing device 50b may be photodiodes (e.g., silicon-based photodiodes), and the another optoelectronic device 850 may be the green sensor 50c, which may be the same as or different from the green sensor 50c shown in Figure 8 . The another optoelectronic device 850 includes a first electrode 101, an active layer 103, and a second electrode (upper electrode) 102, and the optoelectronic device 100 includes a first electrode 10, an active layer 30, and a second electrode 20.

[0467] However, in the organic sensor 900 according to some example embodiments, the blue light sensing device 50a and the red light sensing device 50b integrated in the semiconductor substrate 110 are stacked in the vertical direction (e.g., perpendicular to the top surface 110S of the semiconductor substrate 110). The blue light sensing device 50a and the red light sensing device 50b can be configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in respective wavelength regions depending on the stacking depth and thus sense it. In other words, compared to the blue light sensing device 50a configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) blue light in the short wavelength region, the red light sensing device 50b configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) red light in the long wavelength region is disposed deeper from the surface of the semiconductor substrate 110. In this way, the color filter layer 70 can be omitted by the separate absorption wavelengths depending on the stacking depth.

[0468] Figure 10 FIG. is a cross-sectional view showing an organic sensor according to some example embodiments.

[0469] Reference Figure 10 , the organic sensor 950 according to some example embodiments includes a visible light sensor 50 and a photoelectric device 100 similar to the organic sensor of some example embodiments. The visible light sensor 50 includes a blue light sensing device 50a, a green sensor 50c, and a red light sensing device 50b integrated in the semiconductor substrate 110, where the blue light sensing device 50a, the green sensor 50c, and the red light sensing device 50b can be photodiodes.

[0470] In an organic sensor 950 according to some example embodiments, a blue light sensing device 50a, a green sensor 50c, and a red light sensing device 50b integrated in a semiconductor substrate 110 are stacked in a vertical direction. The blue light sensing device 50a, the green sensor 50c, and the red light sensing device 50b can be configured to selectively absorb and / or convert (into an electrical signal, such as photoelectric conversion) light in respective wavelength regions depending on a stacking depth from a top surface 110S and thus sense it. In other words, compared to the blue light sensing device 50a configured to selectively absorb and / or convert (into an electrical signal, such as photoelectric conversion) blue light in a short wavelength region, the red light sensing device 50b configured to selectively absorb and / or convert (into an electrical signal, such as photoelectric conversion) red light in a long wavelength region is disposed deeper from the top surface 110S of the semiconductor substrate 110, and the green sensor 50c configured to selectively absorb and / or convert (into an electrical signal, such as photoelectric conversion) green light in a medium wavelength region is disposed deeper from the top surface 110S of the semiconductor substrate 110 than the blue light sensing device 50a and closer to the top surface 110S of the semiconductor substrate 110 than the red light sensing device 50b. In this way, by separate absorption wavelengths depending on the stacking depth, a color filter layer 70 can be omitted.

[0471] Figure 11 FIG. is a cross-sectional view showing an organic sensor according to some example embodiments.

[0472] Reference Figure 11 , an organic sensor 970 according to some example embodiments includes a first optoelectronic device (e.g., an infrared / near-infrared optoelectronic device 1200d) configured to selectively absorb and / or convert (into an electrical signal, such as photoelectric conversion) light in an infrared / near-infrared wavelength spectrum (e.g., a first near-infrared wavelength region) of incident light, and at least one additional optoelectronic device (e.g., 1200a - 1200c) vertically stacked between the first optoelectronic device and a semiconductor substrate (e.g., 110), each individual optoelectronic device of the at least one additional optoelectronic device including a separate photoelectric conversion layer and being configured to selectively absorb and / or convert (into an electrical signal, such as photoelectric conversion) light in separate (e.g., respective) wavelength regions of incident light, the separate wavelength regions of the incident light being different from the first near-infrared wavelength region and being separate visible and / or non-visible wavelength regions. For example, as Figure 11As shown, the organic sensor 970 may include additional optoelectronic devices, the additional optoelectronic devices including a red optoelectronic device configured to selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in the red wavelength spectrum of incident light, a green optoelectronic device configured to selectively absorb and / or convert (convert into an electrical signal) light in the green wavelength spectrum of incident light, and a blue optoelectronic device configured to selectively absorb and / or convert (convert into an electrical signal) light in the blue wavelength spectrum of incident light, and stack them in the vertical direction (e.g., the Z direction).

[0473] Therefore, it will be understood that, as Figure 11 shown, the organic sensor 970 may include a plurality of optoelectronic devices 1200a - 1200d, the plurality of optoelectronic devices 1200a - 1200d being vertically stacked on the semiconductor substrate 110 such that the plurality of optoelectronic devices 1200a - 1200d overlap each other in a direction extending perpendicular to the top surface 110S of the semiconductor substrate 110. Although the organic sensor 970 further includes a plurality of additional optoelectronic devices 1200a - 1200c in addition to the first optoelectronic device (e.g., the fourth optoelectronic device 1200d) configured to selectively absorb and / or convert light in the first near-infrared wavelength region, it will be understood that in some example embodiments, the organic sensor 970 may be limited to a single additional optoelectronic device (e.g., any one of 1200a to 1200c) between the optoelectronic device 1200d and the semiconductor substrate 110.

[0474] The organic sensor 970 according to some example embodiments includes a semiconductor substrate 110, a lower insulating layer 80a, an intermediate insulating layer 80b, an additional intermediate insulating layer 80c, an upper insulating layer 80d, a first optoelectronic device 1200a, a second optoelectronic device 1200b, a third optoelectronic device 1200c, and a fourth optoelectronic device 1200d. In some example embodiments, the fourth optoelectronic device 1200d may be referred to as the first optoelectronic device configured to selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in the first near-infrared wavelength region, and the first to third optoelectronic devices 1200a to 1200c may be collectively referred to as at least one additional optoelectronic device configured to selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in one or more separate wavelength regions different from the first near-infrared wavelength region. As shown, the first to fourth optoelectronic devices 1200a to 1200d are vertically stacked on the semiconductor substrate 110 such that the first to fourth optoelectronic devices 1200a to 1200d overlap each other in a direction extending perpendicular to the top surface 110S of the semiconductor substrate 110.

[0475] The semiconductor substrate 110 may be a silicon substrate and is integrated with a transfer transistor (not shown) and a charge memory.

[0476] The first to third optoelectronic devices 1200a - 1200c may have the same structure as the additional optoelectronic device 850 shown in Figure 8 and 9 , except as follows: Each individual optoelectronic device 1200a - 1200c may be configured to photoelectrically convert visible and / or non - visible (e.g., near - infrared) light in separate wavelength regions, and the photoelectric conversion layers 1230a - 1230c may have the same structure and / or composition as various exemplary embodiments (e.g., different exemplary embodiments) of the active layer 103 and / or the active layer 30 described herein, so as to be configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in different visible and / or non - visible wavelength regions, and may include the near - infrared absorber. The fourth optoelectronic device 1200d may have the same structure as the optoelectronic device 100 of Figure 1 and / or Figure 2 the optoelectronic device 200 of, and the photoelectric conversion layer 1230d may have the same structure and / or composition as the active layer 30 described herein, and may include the near - infrared absorber.

[0477] The first optoelectronic device 1200a is formed on the lower insulating layer 80a. The first optoelectronic device 1200a includes the photoelectric conversion layer 1230a. The first optoelectronic device 1200a may be any of the optoelectronic devices described herein according to any exemplary embodiment. The photoelectric conversion layer 1230a may selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in one of the infrared, red, blue, and green wavelength spectra of the incident light. For example, the first optoelectronic device 1200a may be a blue optoelectronic device.

[0478] The intermediate insulating layer 80b is formed on the first optoelectronic device 1200a.

[0479] The second optoelectronic device 1200b is formed on the intermediate insulating layer 80b. The second optoelectronic device 1200b includes the photoelectric conversion layer 1230b. The second optoelectronic device 1200b may be any of the optoelectronic devices described herein according to any exemplary embodiment. The photoelectric conversion layer 1230b may selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in one of the infrared, red, blue, or green wavelength spectra of the incident light. For example, the second optoelectronic device 1200b may be a green optoelectronic device.

[0480] Another intermediate insulating layer 80c is formed on the second optoelectronic device 1200b.

[0481] The third optoelectronic device 1200c is formed on the intermediate insulating layer 80c. The third optoelectronic device 1200c includes a photoelectric conversion layer 1230c. The third optoelectronic device 1200c can be any one of the optoelectronic devices described herein according to any exemplary embodiment. The photoelectric conversion layer 1230c can selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in one of the infrared, red, blue, or green wavelength spectra of incident light. For example, the third optoelectronic device 1200c can be a red optoelectronic device.

[0482] The upper insulating layer 80d is formed on the third optoelectronic device 1200c.

[0483] The lower insulating layer 80a, the intermediate insulating layers 80b and 80c, and the upper insulating layer 80d have a plurality of through holes exposing the charge memories 55a, 55b, 55c, and 55d.

[0484] The fourth optoelectronic device 1200d is formed on the upper insulating layer 80d. The fourth optoelectronic device 1200d includes a photoelectric conversion layer 1230d. The fourth optoelectronic device 1200d can be any one of the optoelectronic devices described herein according to any exemplary embodiment. The photoelectric conversion layer 1230d can selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in one of the infrared, red, blue, or green wavelength spectra of light. For example, the fourth optoelectronic device 1200d can be an infrared / near-infrared optoelectronic device that can include the near-infrared absorber.

[0485] In the figure, the first optoelectronic device 1200a, the second optoelectronic device 1200b, the third optoelectronic device 1200c, and the fourth optoelectronic device 1200d are sequentially stacked, but the present disclosure is not limited thereto, and they can be stacked in various orders.

[0486] As described above, the first optoelectronic device 1200a, the second optoelectronic device 1200b, the third optoelectronic device 1200c, and the fourth optoelectronic device 1200d have a stacked structure, and thus the size of the organic sensor can be reduced to realize a miniaturized organic sensor.

[0487] The organic sensor can be applied to various electronic devices, for example, 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.

[0488] Figure 12 It is a block diagram of a digital camera including an image sensor according to some exemplary embodiments.

[0489] Reference 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 one of the image sensors according to some example embodiments of the example embodiments shown in Figures 3 to 11 One of the image sensors according to some example embodiments of the example embodiments shown.

[0490] The lens 1010 focuses the incident light on the image sensor 1020. The image sensor 1020 generates RGB data for the received light passing through the lens 1010.

[0491] In an example embodiment, the image sensor 1020 may interface with the engine 1040.

[0492] The motor 1030 may 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 may control the image sensor 1020 and the motor 1030.

[0493] The engine 1040 may be connected to the host / application 1050.

[0494] Figure 13 A schematic diagram showing an electronic device 1100 according to some embodiments. Refer to Figure 13 , the electronic device 1100 may include a processor 1120, a memory 1130, and an image sensor 1140 that are electrically coupled (connected) together via a bus 1110. The image sensor 1140 may be an image sensor and / or an organic sensor according to any example embodiment of an image sensor and / or an organic sensor. The memory 1130 may be a non-transitory computer-readable medium and may store an instruction program. The memory 1130 may be a non-volatile memory such as flash memory, phase change random access memory (PRAM), magnetoresistive RAM (MRAM), resistive RAM (ReRAM), or ferroelectric RAM (FRAM), or a volatile memory such as static RAM (SRAM), dynamic RAM (DRAM), or synchronous DRAM (SDRAM). The processor 1120 may execute the stored instruction program to implement one or more functions. For example, the processor 1120 may be configured to process the electrical signals generated by the image sensor 1140. The processor 1120 may include processing circuitry such as hardware including logic circuitry; a hardware / software combination such as a processor that executes software; or a combination thereof. For example, the processing circuitry may more particularly 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. The processor 1120 may be configured to generate an output (e.g., an image to be displayed on a display interface) based on such processing.

[0495] In the following, some example embodiments are shown in more detail with reference to the exemplary embodiments. However, the example embodiments are not limited to these embodiments.

[0496] Synthesis Example

[0497] Synthesis Example 1: Synthesis of the compound represented by Chemical Formula 1-1

[0498] [Chemical Formula 1-1]

[0499]

[0500] [Reaction Scheme 1-1]

[0501]

[0502] i) First step: Synthesis of Compound 1-1C

[0503] In a round-bottom flask under nitrogen pressure, 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), and tetrakis(triphenylphosphine)palladium(0) (0.11 g, 0.093 mmol) was added thereto. Subsequently, the obtained mixture was heated at 110 °C, then refluxed and stirred for 24 hours. When the reaction was completed, the reaction solution was concentrated by removing toluene, then separated by silica gel chromatography (eluent: dichloromethane:n-hexane = 1:4, by volume ratio) and precipitated in 50 ml of toluene to obtain 0.95 g (yield: 70%) of Compound 1-1C.

[0504] ii) Second step: Synthesis of Compound 1-1D

[0505] In a round-bottom flask under nitrogen pressure, Compound 1-1C (0.56 g, 0.76 mmol) was dissolved in acetic acid (10 ml), and iron powder (0.33 g, 5.91 mmol) was added thereto. The obtained mixture was heated and stirred at 80 °C for 12 hours. The reaction product was cooled to room temperature, and distilled water was added thereto. Extraction was performed using dichloromethane, and the obtained organic layer was dried using MgSO4. After filtering MgSO4, the liquid obtained therefrom was concentrated to obtain 0.28 g (yield: 55%) of Compound 1-1D.

[0506] iii) Third step: Synthesis of the compound represented by Chemical Formula 1-1

[0507] In a round-bottom flask under nitrogen pressure, compound 1-1D (0.28 g, 0.42 mmol) was dissolved in pyridine (5 ml), and N-sulfinylaniline (0.19 ml, 1.69 mmol) and chlorotrimethylsilane (0.38 ml, 2.97 mmol) were added thereto, followed by stirring at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, then precipitated in 50 ml of methanol and filtered, and 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.

[0508] MALDI-TOF molecular weight analysis: 688.376 m / z

[0509] Synthesis Example 2: Synthesis of the compound represented by Chemical Formula 1-2

[0510] [Chemical Formula 1-2]

[0511]

[0512] [Reaction Scheme 1-2]

[0513]

[0514] In a round-bottom flask under nitrogen pressure, the compound 1-1D (0.05 g, 0.076 mmol) of Synthesis Example 1 was dissolved in ethanol / chloroform, and selenium dioxide (0.011 g, 0.091 mmol) was added thereto, followed by stirring at 80 °C for 12 hours. When the reaction was completed, the reaction mixture was 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.

[0515] MALDI-TOF molecular weight analysis: 735.953 m / z

[0516] Synthesis Example 3: Synthesis of the compound represented by Chemical Formula 1-3

[0517] [Chemical Formula 1-3]

[0518]

[0519] [Reaction Scheme 1-3]

[0520]

[0521] In a round-bottom flask under nitrogen pressure, the compound 1-1D (0.02 g, 0.03 mmol) of Synthesis Example 1 was dissolved in acetic acid / chloroform, and phenanthrene-9,10-dione (0.007 g, 0.033 mmol) was added thereto, followed by stirring at 55 °C for 12 hours. Subsequently, distilled water was added to the reaction mixture, and the resulting solid was filtered and washed thoroughly with hexane and ethyl acetate to obtain 0.016 g (yield: 64%) of the compound represented by Chemical Formula 1-3.

[0522] MALDI-TOF molecular weight analysis: 832.487 m / z

[0523] Synthesis Example 4: Synthesis of the compound represented by Chemical Formula 1-4

[0524] [Chemical Formula 1-4]

[0525]

[0526] [Reaction Scheme 1-4]

[0527]

[0528] i) First step: Synthesis of compound 1-4C

[0529] In a round-bottom flask under nitrogen pressure, the compound 1-4A (4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole, 0.8 g, 1.86 mmol) and the compound 1-4B (4-methyl-2-(tributylstannyl)-4H-thieno[3,2-b]indole, 1.2 g, 3.71 mmol) were dissolved in toluene (20 ml), and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.1 mmol) was added thereto. Subsequently, the mixture was heated and stirred at 110 °C for 24 hours. When the reaction was completed, after removing toluene, the reaction solution was concentrated, separated by silica gel chromatography (eluent: dichloromethane:n-hexane = 1:4, by volume), and precipitated in 50 ml of methanol to obtain 0.9 g (yield: 72%) of compound 1-4C.

[0530] ii) Second step: Synthesis of compound 1-4D

[0531] In a round-bottom flask under nitrogen pressure, compound 1-4C (0.34 g, 0.57 mmol) was dissolved in ethanol (9 ml) and ethyl acetate (18 ml), and palladium on carbon (0.3 g, 0.28 mmol) and ammonium formate (3.59 g, 56.98 mmol) were added thereto. Subsequently, the mixture was heated and stirred at 60 °C for 12 hours. The reaction product was cooled to room temperature, separated by silica gel chromatography (eluent: dichloromethane:n-hexane = 2:1, by volume), and precipitated in 100 ml of hexane to obtain 0.16 g (yield: 52%) of compound 1-4D.

[0532] iii) Step 3: Synthesis of the compound represented by Chemical Formula 1-4

[0533] In a round-bottom flask under nitrogen pressure, compound 1-4D (0.1 g, 0.42 mmol) was dissolved in pyridine (3 ml), and N-sulfinylaniline (0.08 ml, 0.74 mmol) and chlorotrimethylsilane (0.16 ml, 1.3 mmol) were added thereto, and then stirred at 80 °C for 12 hours. The reaction product was cooled to room temperature, precipitated and filtered in 30 ml of methanol, and the solid obtained therefrom was washed thoroughly with dichloromethane and ethyl acetate to obtain 0.06 g (yield: 59%) of the compound represented by Chemical Formula 1-4.

[0534] Synthesis Example 5: Synthesis of the compound represented by Chemical Formula 1-5

[0535] [Chemical Formula 1-5]

[0536]

[0537] [Reaction Scheme 1-5]

[0538]

[0539] In a round-bottom flask under nitrogen pressure, compound 1-4D (0.03 g, 0.055 mmol) was dissolved in ethanol / chloroform, and selenium dioxide (0.0074 g, 0.067 mmol) was added thereto, and then stirred at 80 °C for 12 hours. When the reaction was completed, the reaction product was concentrated, and the solid obtained therefrom was washed thoroughly with dichloromethane and ethyl acetate to obtain 0.02 g (yield: 59%) of the compound represented by Chemical Formula 1-5.

[0540] Synthesis Example 6: Synthesis of the compound represented by Chemical Formula 1-6

[0541] [Chemical Formula 1-6]

[0542]

[0543] [Reaction Scheme 1-6]

[0544]

[0545] In a round-bottom flask under nitrogen pressure, the compound 1-4D (0.03 g, 0.055 mmol) of Synthesis Example 4 was dissolved in acetic acid / chloroform, and phenanthrene-9,10-dione (0.012 g, 0.061 mmol) was added thereto, and then the mixture was stirred at 55 °C for 12 hours. The solid formed therein by adding distilled water to the reaction mixture was filtered and washed thoroughly with hexane and ethyl acetate to obtain 0.02 g (yield: 59%) of the compound represented by Chemical Formula 1-6.

[0546] Synthesis Example 7: Synthesis of the compound represented by Chemical Formula 1-7

[0547] [Chemical Formula 1-7]

[0548]

[0549] [Reaction Scheme 1-7]

[0550]

[0551] i) First step: Synthesis of compound 1-7C

[0552] In a round-bottom flask under nitrogen pressure, the compound 1-7A (4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole, 0.71 g, 1.86 mmol) and the compound 1-7B (8-phenyl-2-(tributylstannyl)-8H-thieno[2,3-b]indole, 2 g, 3.71 mmol) were dissolved in toluene (18 ml), and tetrakis(triphenylphosphine)palladium(0) (0.11 g, 0.093 mmol) was added thereto. Subsequently, the mixture was heated at 110 °C, then refluxed and stirred for 24 hours. When the reaction was completed, after removing toluene, the reaction solution was concentrated, separated by silica gel chromatography (eluent: dichloromethane:n-hexane = 1:4, by volume), and precipitated in 50 ml of methanol to obtain 0.1 g (yield: 74%) of compound 1-7C.

[0553] ii) Second step: Synthesis of compound 1-7D

[0554] In a round-bottom flask under nitrogen pressure, compound 1-7C (0.6 g, 0.83 mmol) was dissolved in acetic acid (20 ml), and iron powder (1.39 g, 24.97 mmol) was added thereto. Subsequently, the mixture was heated and stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, and distilled water was added thereto. Extraction was carried out using dichloromethane, and the organic layer obtained therefrom was dried using MgSO4. After filtering off MgSO4, the liquid obtained therefrom was concentrated to obtain 0.31 g (yield: 56%) of compound 1-7D.

[0555] iii) Step 3: Synthesis of the compound represented by Chemical Formula 1-7

[0556] In a round-bottom flask under nitrogen pressure, compound 1-7D (0.1 g, 0.15 mmol) was dissolved in pyridine (2 ml), and N-sulfinylaniline (0.07 ml, 0.6 mmol) and chlorotrimethylsilane (0.13 ml, 1.06 mmol) were added thereto, and then the mixture was stirred at 80 °C for 12 hours. The reaction mixture was cooled to room temperature, precipitated in 30 ml of methanol and subjected to paper filtration, and the solid obtained therefrom was washed thoroughly with dichloromethane and ethyl acetate to obtain 0.08 g (yield: 77%) of the compound represented by Chemical Formula 1-7.

[0557] Synthesis Example 8: Synthesis of the compound represented by Chemical Formula 1-8

[0558] [Chemical Formula 1-8]

[0559]

[0560] [Reaction Scheme 1-8]

[0561]

[0562] In a round-bottom flask under nitrogen pressure, compound 1-7D of Synthesis Example 7 (0.1 g, 0.15 mmol) was dissolved in ethanol / chloroform, and selenium dioxide (0.02 g, 0.18 mmol) was added thereto, and then the mixture was stirred at 80 °C for 12 hours. When the reaction was completed, the reaction mixture was concentrated, and the solid obtained therefrom was washed thoroughly with dichloromethane and ethyl acetate to obtain 0.07 g (yield: 63%) of the compound represented by Chemical Formula 1-8.

[0563] Synthesis Example 9: Synthesis of the compound represented by Chemical Formula 1-9

[0564] [Chemical Formula 1-9]

[0565]

[0566] [Reaction Scheme 1-9]

[0567]

[0568] In a round-bottom flask under nitrogen pressure, the compound 1-7D (0.1 g, 0.15 mmol) of Synthesis Example 7 was dissolved in acetic acid / chloroform, and phenanthrene-9,10-dione (0.038 g, 0.18 mmol) was added thereto, followed by stirring at 55 °C for 12 hours. The solid formed therein by adding distilled water to the reaction mixture was filtered, and then washed thoroughly with hexane and ethyl acetate to obtain 0.09 g (yield: 72%) of the product.

[0569] MALDI-TOF molecular weight analysis: 832.487 m / z

[0570] Synthesis Comparative Example 1: Synthesis of the compound represented by Chemical Formula 2-1

[0571] [Chemical Formula 2-1]

[0572]

[0573] 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 hours. When the reaction was completed, the toluene was evaporated and concentrated, and precipitation was carried out using dichloromethane to obtain 0.1 g (yield: 52%) of the product.

[0574] MALDI-TOF molecular weight analysis: 692 m / z

[0575] Synthesis Comparative Example 2: Synthesis of the compound represented by Chemical Formula 2-2

[0576] [Chemical Formula 2-2]

[0577]

[0578] [Reaction Scheme 2-2]

[0579]

[0580] 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 tetrakis(triphenylphosphine)palladium(0) (0.376 g, 0.326 mmol) was added thereto. Subsequently, the mixture was heated at 110 °C and refluxed and stirred for 24 hours. The reaction product was cooled to room temperature (24 °C) and concentrated, and ethyl acetate was added thereto. Subsequently, the solid formed therein was filtered and then washed with n-hexane / ethyl acetate / methanol. The solid was dried under vacuum to obtain a green solid of the compound represented by Chemical Formula 2-2 (1.5 g).

[0581] 1 H NMR (500 MHz, CDCl3): δ 8.92 (d, 2H), δ 8.75 (s, 2H), δ 7.35 (t, 8H), δ 7.30 (d, 8H), δ 7.14 (t, 4H), δ 6.75 (d, 2H).

[0582] UPLC-MS: [M+H] + 687.06

[0583] Synthesis Comparative Example 3: Synthesis of the compound represented by Chemical Formula 2-3

[0584] The compound represented by Chemical Formula 2-3 was synthesized by the method described in the article (D. Ma, Z. Y. Wang et al., J. Phys. Chem. C, 2009, 113, 1589-1595).

[0585] [Chemical Formula 2-3]

[0586]

[0587] Synthesis Comparative Example 4: Synthesis of the compound represented by Chemical Formula 2-4

[0588] [Chemical Formula 2-4]

[0589]

[0590] [Reaction Scheme 2-4]

[0591]

[0592] In a round-bottom flask under nitrogen pressure, compound 2-4A (4,9-dibromo-[1,2,5]thiadiazolo[3,4-g]quinoxaline, 530 mg, 1.53 mmol), compound 2-4B (diphenylamine, 646 mg, 3.82 mmol), and sodium tert-butoxide (317 mg, 4.59 mmol) were dissolved in toluene (10 ml), and bis(tri-tert-butylphosphine)palladium(0) (78 mg, 0.153 mmol) was added thereto. Subsequently, the mixture was heated at 110 °C, then refluxed and stirred for 24 hours. The reaction mixture was cooled to room temperature (24 °C) and concentrated, and then ethyl acetate, distilled water, and an aqueous ammonium chloride solution were added thereto in sequence. Extraction was performed using ethyl acetate, and the organic layer obtained therefrom was dried using MgSO4. After filtering off MgSO4, the solution was concentrated, purified by silica gel column chromatography (eluent: ethyl acetate:hexane = 1:4, by volume ratio), and dried under vacuum to obtain 120 mg (yield: 15%) of a green solid of the compound represented by Chemical Formula 2-4.

[0593] 1 H NMR (300 MHz, CD2Cl2): δ 8.57 (s, 2H), δ 7.19 (d, 8H), δ 7.06 (d, 8H), δ 6.98 (t, 4H).

[0594] UPLC-MS: [M+H] + 523.14

[0595] Synthesis Comparative Example 5: Synthesis of the compound represented by Chemical Formula 2-5

[0596] The compound represented by Chemical Formula 2-5 was synthesized using the method described in Scheme 1 (ACS Nano, Highly Stable Organic Small Molecular Nanoparticles as an Advanced and Biocompatible Phototheranostic Agent of Tumor in Living Mice, 2017, 7177-7188).

[0597] [Chemical Formula 2-5]

[0598]

[0599] Evaluation I: Light Absorption Characteristics

[0600] The compounds of Synthesis Example 1 and Synthesis Comparative Examples 3 and 4 were respectively dissolved in dichloromethane at a concentration of 1×10 -5 M to evaluate their light absorption characteristics in the solution state.

[0601] In addition, the compound of Synthesis Example 1 was deposited on a glass substrate to form a 30-nm-thick film, and thus its light absorption characteristics in the film state were evaluated. On the other hand, the compounds of Comparative Examples 1 and 2 could not be deposited and thus could not be evaluated. The maximum absorption wavelength (λ 最大 ) was measured using a UV-Vis-NIR spectrometer (Shimadzu UV-3600Plus) to evaluate the light absorption characteristics. The results are shown in Table 1.

[0602] On the other hand, for the compounds according to Synthesis Examples 2-9 and Comparative Example 5, when the sample was set as a toluene solution, DFT and TD-DFT (wB97X-D function with the 6-311G(d,p) basis set) were calculated using the Gaussian09 (G09) program. The results are shown in Table 2.

[0603] (Table 1)

[0604] <![CDATA[λ 最大 (nm) (solution)]]> <![CDATA[λ 最大 (nm)(thin film)]]> Synthesis Example 1 908 963 Synthesis Comparative Example 3 594 623 Synthesis Comparative Example 4 692 690

[0605] (Table 2)

[0606]

[0607]

[0608] Referring to Tables 1 and 2, compared with the compounds according to Comparative Examples 1-5, the compounds according to Synthesis Examples 1-9 exhibited sufficient wavelength absorption in the near-infrared wavelength region.

[0609] The compounds of Synthesis Examples 1-7 were used to calculate the oscillator strength at the DFT B3LYP / 6-311G(d,p) level using the Gaussian 09 program, and the results are shown in Table 3.

[0610] (Table 3)

[0611] Oscillator Strength (Arbitrary Unit) Synthesis Example 1 0.81 Synthesis Example 2 0.67 Synthesis Example 3 0.72 Synthesis Example 4 0.80 Synthesis Example 5 0.66 Synthesis Example 6 0.72 Synthesis Example 7 0.69

[0612] Referring to Table 3, the compounds according to Synthesis Examples 1-7 exhibited high oscillator strength and thus high absorption coefficients.

[0613] Evaluation II: Deposition Characteristics

[0614] Evaluate the deposition characteristics of the compounds of Synthesis Examples 1-9 and Synthesis Comparative Examples 1-5. The deposition characteristics were evaluated by thermogravimetric analysis (TGA) as follows: The compounds were sublimated under a high vacuum of less than or equal to 10 Pa, and the thermal stability was evaluated from the weight loss according to the temperature increase. The results of Synthesis Examples 1-3 and Synthesis Comparative Examples 1 and 2 are shown in Table 4.

[0615] (Table 4)

[0616] <![CDATA[T s (℃)(-10 wt%)]]> Synthesis Example 1 365 Synthesis Example 2 375 Synthesis Example 3 370 Synthesis Comparative Example 1 Non-depositable Synthesis Comparative Example 2 Non-depositable

[0617] *Ts (°C) (-10 wt%): The temperature at which the weight of the sample decreases by 10 wt%

[0618] Referring to Table 4, the compounds of Synthesis Examples 1-3 are depositible. On the other hand, the compounds of Synthesis Comparative Examples 1 and 2 are non-depositible and thus cannot be evaluated.

[0619] Examples and Comparative Examples: Fabrication of Optoelectronic Devices

[0620] 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 1-9 and Synthesis Comparative Examples 3-5 was co-deposited with C60 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 active layer to form a secondary layer with a thickness of 30 nm. Then, ITO was sputtered on the secondary layer to form a cathode with a thickness of 7 nm. Aluminum oxide (Al2O3) was deposited on the cathode to form an antireflection layer with a thickness of 50 nm, and it was encapsulated with a glass plate to fabricate the optoelectronic devices according to Examples 1-9 and Comparative Examples 3-5.

[0621] Evaluation III: Photovoltaic Conversion Efficiency

[0622] Evaluate the photoelectric conversion efficiency of the optoelectronic devices according to Examples 1-9 and Comparative Examples 3-5. The photoelectric conversion efficiency was measured using an IPCE measurement system (TNE Technology Co., Ltd., Korea). First, the system was calibrated by using a Si photodiode (Hamamatsu Photonics K.K., Japan), and then it was mounted on the optoelectronic device to measure the photoelectric conversion efficiency in the wavelength range of about 400 nm to about 1600 nm. The results of Example 1 and Comparative Example 4 are shown in Figure 14 in. Figure 14 is a graph showing the photoelectric conversion efficiency of the optoelectronic devices of Example 1 and Comparative Example 4.

[0623] Referring to Figure 14, compared with the optoelectronic device of Comparative Example 4, the optoelectronic device of Example 1 exhibits excellent photoelectric conversion efficiency in the long wavelength region of about 1000 nm.

[0624] 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.

Claims

1. Near-infrared absorber, comprising: A compound represented by Chemical Formula 1: [Chemical Formula 1] Wherein, in Chemical Formula 1, Ar is a benzene ring, X 1 is S, Se, or Te, X 2 is O, S, Se, Te, CR x -CR y or CR xx -CR yy wherein R x and R y are independently hydrogen, deuterium, C1-C30 alkyl, C1-C30 haloalkyl, C6-C30 aryl, C6-C30 aryloxy, C3-C30 heteroaryl, halogen, or cyano, R xx and R yy are independently (CH) where v is a positive integer v or at least one heteroatom of O, N, S, Se, or Te, and R xx and R yy are connected to each other to form a C6-C30 aromatic ring or a C3-C30 heteroaromatic ring Ar 1 and Ar 2 are the same or different and are represented by Chemical Formula C-1-1 including at least one aromatic ring: [Chemical Formula C-1-1] Wherein, in Chemical Formula C-1-1, Y 1 is O, S, Se, or Te, The * outside the at least one aromatic ring is the connection point with Ar of Chemical Formula 1, and * within said at least one aromatic ring is the linking moiety of the ring containing N(R 1 ) of Formula 1 and the ring containing N(R 1 ) of Formula 1, including R 2 2 )​ Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6-C30 aryl group, R 1 and R 2 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxy, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C10 aryl, or substituted or unsubstituted C3-C10 heteroaryl, and L 1 and L 2 are independently single bonds, Where "substituted" means that the hydrogen of the functional group is replaced by a substituent selected from the following: halogen atom, hydroxyl group, nitro group, cyano group, amino group, mercapto group, C1-C20 alkyl group, C1-C20 alkoxy group, and combinations thereof.

2. The near-infrared absorber according to claim 1, wherein in Chemical Formula 1, when X 2 is CR xx -CR yy and the aromatic ring formed by connecting R xx to R yy is a benzene ring, a naphthalene ring, an acenaphthene ring, an anthracene ring, a phenanthrene ring, a tetracene ring, or a pyrene ring.

3. The near-infrared absorber according to claim 1, wherein in Chemical Formula 1, when X 2 is CR xx -CR yy and the aromatic ring formed by connecting R xx to R yy is a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a phenanthroline ring, a pyrimidine ring, or a benzodithiophene ring.

4. The near-infrared absorber according to claim 1, wherein in Chemical Formula 1, when X 2 is CR xx -CR yy a group of moieties represented by Chemical Formula B-1, each moiety including at least one aromatic ring: xx and R yy is formed by connecting R [Chemical Formula B-1] Among them, In Chemical Formula B-1, * within said at least one aromatic ring is a linking moiety to the carbon of CR xx -CR yy ​ 5. The near-infrared absorber according to claim 1, wherein in Chemical Formula 1, when X 2 is CR xx -CR yy at this time, the aromatic ring formed by connecting R xx and R yy is a part of a group of parts represented by Chemical Formula B-2, and each part includes at least one aromatic ring: [Chemical Formula B-2] Among them, In Chemical Formula B-2, * within said at least one aromatic ring is a linking moiety to the carbon of CR xx -CR yy ​ 6. The near-infrared absorber according to claim 1, wherein in Chemical Formula 1, when X 2 is CR xx -CR yy a group of moieties represented by Chemical Formula B-3-11, each moiety including at least one aromatic ring, or a moiety of a group of moieties represented by Chemical Formula B-3-21, each moiety including at least one aromatic ring, is formed by connecting R xx to R yy : [Chemical Formula B-3-11] Among them, In Chemical Formula B-3-11, * within the at least one aromatic ring is a linking moiety to the carbon of CR xx -CR yy ​ [Chemical Formula B-3-21] Wherein, in Chemical Formula B-3-21, X a and X b independently is O, S, Se, Te, NR a , SiR b R c , or GeR d R e , wherein R a , R b , R c , R d , and R e independently is hydrogen, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C6-C30 aryloxy, and The * within the aromatic ring is the connecting moiety to the carbon of CR xx -CR yy .

7. The near-infrared absorber according to claim 1, wherein the near-infrared absorber has a peak absorption wavelength in the wavelength region of 750 nm to 3000 nm.

8. Near-infrared absorption / blocking film, comprising the near-infrared absorber according to any one of claims 1-7.

9. Optoelectronic device, comprising: A first electrode and a second electrode facing each other; And An active layer between the first electrode and the second electrode, Wherein the active layer comprises the near-infrared absorber according to any one of claims 1-7.

10. The optoelectronic device according to claim 9, wherein the active layer further comprises fullerene or a fullerene derivative.

11. The optoelectronic device according to claim 9, wherein the active layer has a peak absorption wavelength in the wavelength region of 750 nm to 3000 nm.

12. Organic sensor, comprising the optoelectronic device according to any one of claims 9-11.

13. Electronic device, comprising the organic sensor according to claim 12 or the optoelectronic device according to any one of claims 9-11.

14. Optoelectronic device, comprising: A first electrode and a second electrode facing each other; An active layer between the first electrode and the second electrode; And A charge-assist layer, which is Between the active layer and the first electrode, or Between the active layer and the second electrode, Wherein the charge-assist layer comprises the near-infrared absorber according to any one of claims 1-7.

15. The optoelectronic device according to claim 14, wherein the active layer further comprises the near-infrared absorber.

16. Organic sensor, comprising: A semiconductor substrate; A first optoelectronic device on the semiconductor substrate, the first optoelectronic device being configured to selectively absorb light in a first near-infrared wavelength region; And Another sensor, which is configured to selectively absorb light in a separate wavelength region different from the first near-infrared wavelength region, Wherein the first optoelectronic device comprises the near-infrared absorber according to any one of claims 1-7.

17. The organic sensor according to claim 16, wherein The another sensor is an infrared light sensor at least partially embedded in the semiconductor substrate, and the separate wavelength region is a separate near-infrared wavelength region different from the first near-infrared wavelength region, and The first optoelectronic device and the infrared light sensor overlap in a vertical direction perpendicular to the top surface of the semiconductor substrate.

18. The organic sensor according to claim 16, wherein the additional sensor includes a plurality of photodiodes at least partially embedded in the semiconductor substrate, the plurality of photodiodes configured to selectively absorb light in separate visible wavelength regions, and the first optoelectronic device and the plurality of photodiodes overlap in a vertical direction perpendicular to the top surface of the semiconductor substrate.

19. The organic sensor according to claim 18, further comprising: an additional optoelectronic device on the semiconductor substrate, the additional optoelectronic device being between the first optoelectronic device and the semiconductor substrate, the additional optoelectronic device configured to selectively absorb light in an additional wavelength region different from the first near-infrared wavelength region and the separate visible wavelength regions.

20. The organic sensor according to claim 16, wherein the additional sensor includes at least one additional optoelectronic device vertically stacked between the first optoelectronic device and the semiconductor substrate, each individual optoelectronic device of the at least one additional optoelectronic device including a separate photoelectric conversion layer and configured to selectively absorb light in a separate corresponding wavelength region different from the first near-infrared wavelength region.

21. The organic sensor according to claim 16, wherein the first optoelectronic device includes a first electrode and a second electrode facing each other; and an active layer between the first electrode and the second electrode, wherein the active layer includes the near-infrared absorber.

22. The organic sensor according to claim 16, wherein the first optoelectronic device includes a first electrode and a second electrode facing each other; an active layer between the first electrode and the second electrode; and a charge assisting layer that is between the active layer and the first electrode, or between the active layer and the second electrode, wherein the charge assisting layer includes the near-infrared absorber.

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