Compound, infrared absorber, infrared absorption / blocking film, optoelectronic device, sensor, electronic device, and image sensor

Abstract

The present invention relates to a compound, an infrared absorber, an infrared absorption / blocking film, an optoelectronic device, a sensor, an electronic device, and an image sensor. A compound represented by Chemical Formula 1. In Chemical Formula 1, R 1 to R 4 , R 11a to R 14c and n 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 - 2020 - 0080484, filed on June 30, 2020 with the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference. Technical field

[0003] Compounds, infrared absorbers, infrared (IR) absorption / blocking films, optoelectronic devices, organic sensors, electronic devices, and image sensors are disclosed. Background art

[0004] Imaging devices are used in digital cameras, portable video cameras, etc. to capture an image and store it as an electrical signal, and the imaging device may include a sensor for separating incident light according to wavelength and converting each component into an electrical signal. Summary of the invention

[0005] Some example embodiments provide compounds having improved infrared absorption properties.

[0006] Some example embodiments provide an infrared absorber and an infrared absorption / blocking film including the compound.

[0007] Some example embodiments provide an optoelectronic device including the compound. Such an optoelectronic device may provide improved sensitivity of the sensor in a low - illumination environment and / or may be used as a biometric device.

[0008] Some example embodiments provide a composition including the compound.

[0009] Some example embodiments provide an organic sensor including the compound 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, a compound represented by Chemical Formula 1 is provided:

[0012] [Chemical Formula 1]

[0013]

[0014] Wherein, in Chemical Formula 1,

[0015] R 1 to R 4 may each independently be hydrogen, deuterium, a C1 - C10 alkyl group, a C1 - C10 alkoxy group, a C1 - C10 haloalkyl group, a C6 - C14 aryl group, or a C3 - C12 heteroaryl group,

[0016] R 11a to R 14c may each independently be hydrogen, deuterium, a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, a C6-C14 aryl group, a C6-C14 aryloxy group, a C3-C12 heteroaryl group, or a functional group represented by Chemical Formula 1A, where R 11a to R 14c at least one of which is a functional group represented by Chemical Formula 1A, where R 11a to R 14c exist independently of each other or R 11a to R 14c two adjacent ones of which are connected to each other to form a fused ring with benzindole, and

[0017] n may be an integer of 1 or 2,

[0018] [Chemical Formula 1A]

[0019] ＊ -L1-(L2) m -Ar

[0020] wherein, in Chemical Formula 1A,

[0021] L1 may be a substituted or unsubstituted C2-C15 heteroaromatic ring (heteroaromatic) group,

[0022] L2 may be a substituted or unsubstituted C2-C15 heteroaromatic ring group, a substituted or unsubstituted C6-C30 aromatic ring (aromatic) group, a substituted or unsubstituted C1-C10 alkylene group, or a substituted or unsubstituted C3-C20 cycloalkylene group,

[0023] Ar may be a substituted or unsubstituted C6-C30 aromatic ring group, a substituted or unsubstituted C2-C30 heteroaromatic ring group, a fused ring of the aromatic ring group and the heteroaromatic ring group, a substituted or unsubstituted C6-C30 arylamino group, or a substituted or unsubstituted C2-C30 heteroarylamino group, and

[0024] m is 0, 1 or 2.

[0025] In Chemical Formula 1A, L1 and L2 may each independently be a heteroaromatic ring group represented by one of Chemical Formulas 1A-11 to 1A-15 or a combination thereof.

[0026] [Chemical Formulas 1A-11 to 1A-15]

[0027]

[0028] wherein, in Chemical Formulas 1A-11 to 1A-15,

[0029] X1 and X 2 and X 3 may each independently be O, S, Se, Te, S(=O), S(=O)2, NR a , SiR b R c or GeR d R e , where R a , R b , R c , R d and R e may each independently be hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, C6-C14 aryl, C3-C12 heteroaryl, halogen, cyano or a combination thereof, and

[0030] the hydrogen of each heteroaromatic ring may optionally be replaced by: deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl, C6-C10 aryl, C6-C10 aryloxy, -SiH3 group or C1-C10 alkylsilyl.

[0031] In Chemical Formula 1A, L1 and L2 may each independently be a heteroaromatic ring group represented by one of Chemical Formulas 1A-16 to 1A-20 or a combination thereof:

[0032] [Chemical Formulas 1A-16 to 1A-20]

[0033]

[0034] wherein, in Chemical Formulas 1A-16 to 1A-20,

[0035] X 1 and X 2 may each independently be O, S, Se, Te, S(=O), S(=O)2, NR a , SiR b R c or GeR d R e , where R a , R b , R c , R d and R e may each independently be hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, -SiH3 group, C1-C10 alkylsilyl, -NH2 group, C1-C10 alkylamino, C6-C10 arylamino, C6-C14 aryl, C3-C12 heteroaryl, halogen, cyano or a combination thereof,

[0036] Z 1 to Z4 may each independently be CR x or N, where R x may be hydrogen, deuterium, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a -SiH3 group, a C1-C10 alkylsilyl group, an -NH2 group, a C1-C10 alkylamino group, a C6-C10 arylamino group, a C6-C14 aryl group, a C3-C12 heteroaryl group, a halogen, a cyano group or a combination thereof, or a single bond, where in Chemical Formulas 1A-16 to 1A-18, Z 1 to Z 4 one of which is CR x where R x may be a single bond, and

[0037] the hydrogen of each aromatic ring and heteroaromatic ring may optionally be replaced by the following: deuterium, a halogen, a cyano group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, a -SiH3 group or a C1-C10 alkylsilyl group.

[0038] L1 and L2 may each independently be a combination of a heteroaromatic ring group represented by one of Chemical Formulas 1A-11 to 1A-15 and a heteroaromatic ring group represented by one of Chemical Formulas 1A-16 to 1A-20.

[0039] In Chemical Formula 1A, Ar may be a heteroaromatic ring group represented by one of Chemical Formulas 1B-11 to 1B-15.

[0040] [Chemical Formulas 1B-11 to 1B-15]

[0041]

[0042] In Chemical Formulas 1B-11 to 1B-15,

[0043] X 1 、X 2 and X 3 may each independently be O, S, Se, Te, S(=O), S(=O)2, NR a 、SiR b R c or GeR d R e where R a 、R b 、R c 、R d and R e may each independently be hydrogen, deuterium, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C6-C14 aryl group, a C3-C12 heteroaryl group, a halogen, a cyano group or a combination thereof, and

[0044] The hydrogen of each heteroaromatic ring may optionally be replaced by the following: deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl, C6-C10 aryl, C6-C10 aryloxy, -SiH3 group or C1-C10 alkylsilyl.

[0045] In Chemical Formula 1A, Ar may be a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroaryl, or a fused ring thereof.

[0046] In Chemical Formula 1A, Ar may be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted acenaphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted tetracenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinazolinyl, or a substituted or unsubstituted phenanthrolinyl.

[0047] In Chemical Formula 1A, Ar may be a C6-C30 aryl substituted with an arylamino group, a C2-C15 heteroaryl substituted with an arylamino group, or a fused ring thereof, and the arylamino group may be represented by Chemical Formula 1C-1.

[0048] [Chemical Formula 1C-1]

[0049]

[0050] In Chemical Formula 1C-1,

[0051] Ar 21 and Ar 22 may each independently be a substituted or unsubstituted C6-C30 aryl or a substituted or unsubstituted C3-C30 heteroaryl.

[0052] Chemical Formula 1C-1 may be represented by Chemical Formula 1C-1a or Chemical Formula 1C-1b:

[0053] [Chemical Formula 1C-1a]

[0054]

[0055] In Chemical Formula 1C-1a,

[0056] Z 1 to Z 10 may each independently be N or CR x wherein R xmay be hydrogen, deuterium, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, a -SiH3 group, a C1-C10 alkylsilyl group, a -NH2 group, a C1-C10 alkylamino group, a C6-C12 aryl group, a C3-C12 heteroaryl group, a halogen, a cyano group or a combination thereof, and

[0057] when Z 1 to Z 10 is CR x , Z 1 to Z 10 each respective R x exists independently or at least two adjacent ones of Z 1 to Z 10 are connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring,

[0058] [Chemical Formula 1C-1b]

[0059]

[0060] In Chemical Formula 1C-1b,

[0061] X a and X b may each independently be -O-, -S-, -Se-, -Te-, -NR a -, -SiR b R c -, or -GeR d R e -, where R a , R b , R c , R d and R e may each independently be hydrogen, a halogen, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C10 aryl group,

[0062] Z 1 to Z 6 may each independently be N or CR x , where R x may be hydrogen, deuterium, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, a -SiH3 group, a C1-C10 alkylsilyl group, a -NH2 group, a C1-C10 alkylamino group, a C6-C12 aryl group, a C3-C12 heteroaryl group, a halogen, a cyano group or a combination thereof, and

[0063] when Z 1 to Z 6 is CR x , R x independently exists at Z 1 to Z6 each in or Z 1 to Z 6 At least two adjacent ones of them are connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring.

[0064] In Chemical Formula 1A, Ar can be a C6-C30 aryl group substituted with an N-containing heterocyclic group, a C2-C15 heteroaryl group substituted with an N-containing heterocyclic group, or a fused ring thereof, and the N-containing heterocyclic group can be represented by Chemical Formula 1C-2.

[0065] [Chemical Formula 1C-2]

[0066]

[0067] Wherein, in Chemical Formula 1C-2,

[0068] Ar 23 and Ar 24 can each independently be a substituted or unsubstituted C6-C30 aromatic hydrocarbon group or a substituted or unsubstituted C3-C30 heteroaromatic hydrocarbon group, and

[0069] G can be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h ))=C(R i ))-, wherein R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h and R i can each independently be hydrogen, a halogen, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C10 aryl group, wherein R b 、R c 、R d 、R e 、R f 、R g 、R h and R i can each independently exist or R b and R c 、R d and R e 、Rf and R g or R h and R i may be connected to each other to provide a ring, and -(CR f R g ) n - of n may be 1 or 2.

[0070] Chemical formula 1C-2 may be represented by chemical formula 1C-2a, chemical formula 1C-2b or chemical formula 1C-2c:

[0071] [Chemical formula 1C-2a]

[0072]

[0073] In chemical formula 1C-2a,

[0074] G may be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h ))=C(R i ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R i may each independently be hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, where R b , R c , R d , R e , R f , R g , R h and R i may each independently exist or R b and R c , R d and R e , R f and R g or R h and R i may be connected to each other to provide a ring, and -(CR f R g )n n of - can be 1 or 2,

[0075] Z 1 to Z 8 can each independently be N or CR x wherein R x can be hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3 group, C1-C10 alkylsilyl, -NH2 group, C1-C10 alkylamino, C6-C12 aryl, C3-C12 heteroaryl, halogen, cyano or a combination thereof, and

[0076] when Z 1 to Z 8 is CR x then the respective R of Z 1 to Z 8 exist independently or at least two adjacent ones of Z x to Z 1 are connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, 8

[0077] [Chemical formula 1C-2b]

[0078]

[0079] [Chemical formula 1C-2c]

[0080]

[0081] In Chemical formulas 1C-2b and 1C-2c,

[0082] G can be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f g R n ) h -, or -(C(R i ))=C(R a ))-, wherein R b , R c , R d , R e , R f , R g , R h , R i ​​may each independently be hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, where R b , R c , R d , R e , R f , R g , R h and R i may each independently be present or R b and R c , R d and R e , R f and R g , or R h and R i may be connected to each other to provide a ring, and - (CR f R g ) n - may be 1 or 2,

[0083] X a and X b may each independently be -O-, -S-, -Se-, -Te-, -NR p -, -SiR q R r - or -GeR s R t -, where R p , R q , R r , R s and R t may each independently be hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,

[0084] Z 1 to Z 4 may each independently be N or CR x , where R x may be hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C1 to C10 alkoxy group, a -SiH3 group, a C1 to C10 alkylsilyl group, a -NH2 group, a C1 to C10 alkylamino group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof, and

[0085] when Z 1 to Z 4 is CR x , the respective R 1 to Z 4 exist independently or Z x to Z 1 to Z4 At least two adjacent ones of them are connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring.

[0086] In Chemical Formula 1A, Ar may be an aromatic ring or heteroaromatic ring group represented by one of Chemical Formulas 1B-16 to 1B-25.

[0087] [Chemical Formulas 1B-16 to 1B-25]

[0088]

[0089] In Chemical Formulas 1B-16 to 1B-25,

[0090] X 1 and X 2 may each independently be O, S, Se, Te, S(=O), S(=O)2, NR a , SiR b R c or GeR d R e , where R a , R b , R c , R d and R e may each independently be hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a -SiH3 group, a C1 to C10 alkylsilyl group, a -NH2 group, a C1 to C10 alkylamino group, a C6 to C10 arylamino group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group or a combination thereof,

[0091] Z 1 to Z 4 may each independently be CR x or N, where R x is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a -SiH3 group, a C1 to C10 alkylsilyl group, a -NH2 group, a C1 to C10 alkylamino group, a C6 to C10 arylamino group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group or a combination thereof, or a single bond, where in Chemical Formula 1B-20, one of Z 1 to Z 4 may be CR x , where R x may be a single bond,

[0092] Ar 11 and Ar 12 may each independently be a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group or a substituted or unsubstituted C3 to C30 heteroaromatic hydrocarbon group, and

[0093] The hydrogen of each aromatic ring and heteroaromatic ring may be replaced by the following: deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl, C6-C10 aryl, C6-C10 aryloxy, -SiH3 group or C1-C10 alkylsilyl.

[0094] The aromatic ring or heteroaromatic ring group represented by Chemical Formulas 1B-16 to 1B-25 may be substituted with an arylamino group, and the arylamino group may be represented by Chemical Formula 1C-1. Chemical Formula 1C-1 may be represented by Chemical Formula 1C-1a or Chemical Formula 1C-1b.

[0095] The aromatic ring or heteroaromatic ring group represented by one of Chemical Formulas 1B-16 to 1B-25 may be substituted with an N-containing heterocyclic group, and the N-containing heterocyclic group may be represented by Chemical Formula 1C-2. Chemical Formula 1C-2 may be represented by Chemical Formula 1C-2a, Chemical Formula 1C-2b or Chemical Formula 1C-2c.

[0096] In Chemical Formula 1, at least one of R 11a 、R 11b 、R 11c 、R 12a 、R 12b 、R 12c or R 13a 、R 13b 、R 13c 、R 14a 、R 14b 、R 14c may be a functional group represented by Chemical Formula 1A, and at least one of R

[0097] In some exemplary embodiments, at least one of R 11a 、R 11b or R 11c may be a functional group represented by Chemical Formula 1A, and at least one of R 13a 、R 13b or R 13c may be a functional group represented by Chemical Formula 1A.

[0098] In some exemplary embodiments, at least one of R 12a 、R 12b or R 12c may be a functional group represented by Chemical Formula 1A, and at least one of R 14a 、R 14b or R 14c may be a functional group represented by Chemical Formula 1A.

[0099] In some exemplary embodiments, R 11a and R 13a may be functional groups represented by Chemical Formula 1A.

[0100] In some example embodiments, R 12a and R 14a may be a functional group represented by Chemical Formula 1A.

[0101] According to some example embodiments, an infrared absorber including the compound is provided.

[0102] According to some example embodiments, a composition including the compound is provided.

[0103] The infrared absorber may exhibit a peak absorption wavelength in a wavelength range of about 750 nm to about 3000 nm.

[0104] According to some example embodiments, an infrared absorption / blocking film including the compound is provided.

[0105] According to some example embodiments, an optoelectronic device includes: a first electrode and a second electrode facing each other, and a photoactive layer between the first electrode and the second electrode, wherein the photoactive layer includes the compound represented by Chemical Formula 1 above.

[0106] According to some example embodiments, a sensor including the optoelectronic device is provided.

[0107] According to some example embodiments, an electronic device including the optoelectronic device or the sensor is provided.

[0108] According to some example embodiments, the photoactive layer further includes a fullerene or a fullerene derivative.

[0109] According to some example embodiments, the photoactive layer has a peak absorption wavelength in a wavelength region of about 750 nm to about 3000 nm. The peak absorption wavelength may be in a wavelength region of about 1000 nm to about 3000 nm. The peak absorption wavelength may be in a wavelength region of about 1060 nm to about 1350 nm.

[0110] According to some example embodiments, the photoactive layer has a band gap between about 0.99 eV and about 1.40 eV. The band gap may be between about 0.99 eV and about 1.18 eV.

[0111] According to some example embodiments, the optoelectronic device may include: a first electrode and a second electrode facing each other, a photoactive layer between the first electrode and the second electrode, and a charge assisting layer between the photoactive layer and the first electrode or between the photoactive layer and the second electrode. At least one of the first electrode, the second electrode, the photoactive layer, or the charge assisting layer may include the compound represented by Chemical Formula 1 above.

[0112] The charge assisting layer may include the compound, and the photoactive layer, the first electrode, and the second electrode may not include the compound.

[0113] The photoactive layer may include the compound, and the charge assisting layer, the first electrode, and the second electrode may not include the compound.

[0114] The optoelectronic device may further include a plurality of charge assisting layers, the plurality of charge assisting layers including the charge assisting layer, the plurality of charge assisting layers including a first charge assisting layer between the photoactive layer and the first electrode, and a second charge assisting layer between the photoactive layer and the second electrode. At least one of the first electrode, the second electrode, the photoactive layer, the first charge assisting layer, or the second charge assisting layer may include the compound.

[0115] The sensor may include the optoelectronic device. The electronic device may include the sensor.

[0116] According to some example embodiments, an image 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 infrared wavelength region, and an additional sensor configured to selectively absorb light in a separate wavelength region different from the first infrared wavelength region. The first optoelectronic device may include the compound represented by Chemical Formula 1 above.

[0117] 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 infrared wavelength region different from the first infrared wavelength region. The first optoelectronic device and the infrared light sensor may overlap in a vertical direction perpendicular to the upper surface of the semiconductor substrate.

[0118] The additional sensor may include a plurality of photodiodes at least partially embedded in the semiconductor substrate, the plurality of photodiodes configured to selectively absorb light in a separate visible wavelength region, and the first optoelectronic device and the plurality of photodiodes may overlap in a vertical direction perpendicular to the upper surface of the semiconductor substrate.

[0119] The additional sensor may include at least one additional optoelectronic device vertically stacked between the first optoelectronic device and the semiconductor substrate. Each separate optoelectronic device of the at least one additional optoelectronic device may include a separate photoelectric conversion layer and may be configured to selectively absorb light in a separate wavelength region different from the first infrared wavelength region.

[0120] The first optoelectronic device may include a first electrode and a second electrode facing each other, and a photoactive layer between the first electrode and the second electrode, wherein the photoactive layer includes the compound.

[0121] The first optoelectronic device may include a first electrode and a second electrode facing each other, a photoactive layer between the first electrode and the second electrode, and a charge assisting layer between the photoactive layer and the first electrode or between the photoactive layer and the second electrode. At least one of the first electrode, the second electrode, the photoactive layer, or the charge assisting layer may include the compound.

[0122] The electronic device may include the image sensor.

[0123] The compound may exhibit good light absorption characteristics in the infrared region, and thus can be effectively used in optoelectronic devices and / or organic sensors. Description of the Drawings

[0124] Figure 1 is a cross-sectional view showing an optoelectronic device according to some example embodiments,

[0125] Figure 2 is a cross-sectional view showing an optoelectronic device according to some example embodiments,

[0126] Figure 3 is a cross-sectional view showing an image sensor according to some example embodiments,

[0127] Figure 4 is a cross-sectional view showing an image sensor according to some example embodiments,

[0128] Figure 5 is a cross-sectional view showing an image sensor according to some example embodiments,

[0129] Figure 6 is a cross-sectional view showing an image sensor according to some example embodiments,

[0130] Figure 7 is a cross-sectional view showing an image sensor according to some example embodiments,

[0131] Figure 8 is a cross-sectional view showing an image sensor according to some example embodiments,

[0132] Figure 9 is a cross-sectional view showing an image sensor according to some example embodiments,

[0133] Figure 10 is a cross-sectional view showing an image sensor according to some example embodiments,

[0134] Figure 11 is a block diagram of a digital camera including an image sensor according to some example embodiments,

[0135] Figure 12 is a block diagram of an electronic device according to some example embodiments, and

[0136] Figure 13 is a graph showing the results of measuring the photoelectric conversion efficiency of optoelectronic devices according to Example 1, Example 6, and Comparative Example 1. Detailed Embodiments

[0137] Hereinafter, example embodiments will be described in detail and can be easily carried out by those skilled in the art having ordinary knowledge in the relevant field. However, the present disclosure may be embodied in many different forms and is not to be construed as limited to the example embodiments set forth herein.

[0138] In the drawings, for clarity, the thicknesses of layers, films, panels, regions, etc. are enlarged.

[0139] 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, there are no intervening elements. It will be further understood that when an element is referred to as being "on" another element, it can be above, below, or adjacent to (e.g., horizontally adjacent to) the other element.

[0140] It will be understood that elements and / or their properties (e.g., structure, surface, orientation, etc.) referred to as "perpendicular", "parallel", "coplanar" with respect to other elements and / or their properties can be "perpendicular", "parallel", "coplanar", etc. with respect to the other elements and / or their properties, respectively, or can be "substantially perpendicular", "substantially parallel", "substantially coplanar".

[0141] Elements and / or their properties (e.g., structure, surface, orientation, etc.) that are "substantially perpendicular" with respect to other elements and / or their properties will be understood to be "perpendicular" with respect to the other elements and / or their properties within manufacturing tolerances and / or material tolerances, and / or having a deviation equal to or less than 10% in magnitude and / or angle from being "perpendicular" with respect to the other elements and / or their properties (e.g., a tolerance of ±10%).

[0142] Elements and / or their properties that are "substantially parallel" to other elements and / or their properties (e.g., structure, surface, orientation, etc.) will be understood to be "parallel" to the other elements and / or their properties within manufacturing tolerances and / or material tolerances, and / or having a deviation equal to or less than 10% in magnitude and / or angle from what is "parallel" to the other elements and / or their properties, etc. (e.g., a tolerance of ±10%).

[0143] Elements and / or their properties that are "substantially coplanar" to other elements and / or their properties (e.g., structure, surface, orientation, etc.) will be understood to be "coplanar" to the other elements and / or their properties within manufacturing tolerances and / or material tolerances, and / or having a deviation equal to or less than 10% in magnitude and / or angle from what is "coplanar" to the other elements and / or their properties, etc. (e.g., a tolerance of ±10%).

[0144] It will be understood that an element and / or its properties may be described herein as "the same" or "equal" to another element, and it will further be understood that an element and / or its properties described herein as "the same", "identical", or "equal" to another element may be "the same", "identical", or "equal" or "substantially the same", "substantially identical", or "substantially equal" to the other element and / or its properties. An element and / or its characteristics that are "substantially the same", "substantially identical", or "substantially equal" to another element and / or its properties will be understood to include elements and / or their properties that are the same, identical, or equal to the other element and / or its properties within manufacturing tolerances and / or material tolerances. Elements and / or their properties that are the same or substantially the same and / or equal or substantially equal to another element and / or its 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.

[0145] It will be understood that elements and / or their properties described herein as "substantially" the same and / or identical include elements and / or their properties having a relative difference in magnitude equal to or less than 10%. In addition, whether or not an element and / or its 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 described elements and / or their properties.

[0146] When the terms "about" or "substantially" are used in conjunction with a numerical value in this specification, it is intended that the relevant numerical value include a tolerance of ±10% around the stated numerical value. When a range is specified, the range includes all values therebetween, such as increments of 0.1%.

[0147] In the drawings, for the sake of clarity of some example 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.

[0148] As used herein, "combination" includes mixtures of two or more, intersubstitutions, and laminated structures of two or more.

[0149] 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: halogen, hydroxyl, nitro, cyano, amino, azido, amidino, hydrazino, hydrazono, carbonyl, carbamoyl, mercapto, ester, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, silyl, C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C30 aryl, C7-C30 arylalkyl, C1-C30 alkoxy, C1-C20 heteroalkyl, C3-C20 heteroaryl, C3-C20 heteroarylalkyl, C3-C30 cycloalkyl, C3-C15 cycloalkenyl, C6-C15 cycloalkynyl, C3-C30 heterocycloalkyl, and combinations thereof.

[0150] As used herein, when no specific definition is otherwise provided, "hetero" means that it includes 1 to 4 heteroatoms selected from N, O, S, Se, Te, Si, and P.

[0151] As used herein, when no definition is otherwise provided, "aromatic ring (aromatic group)" 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 (heteroaromatic group)" 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 C3-C30 heteroaryl group, such as a C3-C20 heteroaryl group.

[0152] As used herein, "aromatic hydrocarbon group" refers to a hydrocarbon group having an aromatic ring, and includes monocyclic and polycyclic hydrocarbon groups, and additional rings of the polycyclic hydrocarbon groups may be aromatic rings or non-aromatic rings (non-aromatic groups). Heteroaromatic hydrocarbon group means an aromatic hydrocarbon group containing 1 to 3 heteroatoms selected from N, O, S, Se, Te, P, and Si in the ring.

[0153] As used herein, when no definition is otherwise provided, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and may include: a group in which all elements of the hydrocarbon aromatic portion have p-orbitals forming a conjugation, such as phenyl, naphthyl, etc.; a group in which two or more hydrocarbon aromatic portions can be linked by a σ bond, such as biphenyl, terphenyl, quaterphenyl, etc.; and a group in which two or more hydrocarbon aromatic portions can be fused directly or indirectly to provide a non-aromatic fused ring, such as fluorenyl. Aryl groups may include monocyclic, polycyclic, or fused polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0154] As used herein, when no definition is otherwise provided, "heteroaryl" refers to an aryl group including at least one heteroatom selected from N, O, S, Se, Te, P and Si in the ring instead of carbon (C). When the heteroaryl group is a fused ring, at least one of the rings of the heteroaryl group may have a heteroatom or each ring may have a heteroatom.

[0155] As used herein, when no definition is provided in addition, "ring" refers to an aromatic ring, a non-aromatic ring, a heteroaromatic ring, a hetero non-aromatic ring (hetero non-aromatic ring), a condensed ring thereof, and / or a combination thereof. The aromatic ring is the same as described above, and the non-aromatic ring may be a C3 to C30 cycloalkyl, a C3 to C30 cycloalkenyl, or a C3 to C30 cycloalkynyl.

[0156] As used herein, when no definition is otherwise provided, "halogen" may be one of F, Cl, Br or I, and a haloalkyl group 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.

[0157] As used herein, when no definition is otherwise provided, in a substituted or unsubstituted alkylene group, "substituted alkylene" may include an alkylene group in which at least one hydrogen is replaced by the substituent or at least one methylene is replaced by -O-, -C(=O)-, -OC(=O)-, or -C(=O)O-.

[0158] As used herein, when no additional definition is provided, "cyano-containing group" refers to a monovalent group such as a C1 to C30 alkyl, C2 to C30 alkenyl or C2 to C30 alkynyl in which at least one hydrogen is replaced by a cyano group. A cyano-containing group also refers to a divalent group such as =CR x' -(CR x R y ) p -CR y′ (CN)2, where R x , R y , R x′ and R y′Independently is hydrogen or a C1 to C10 alkyl group, and p can be an integer from 0 to 10 (or 1 to 10). Specific examples of the cyano-containing group can be dicyanomethyl, dicyanovinyl, cyanoethynyl, etc.

[0159] As used herein, when no other definition is provided, the "infrared wavelength region" includes the near-infrared / infrared wavelength region having a wavelength region of about 750 nm to about 3000 nm.

[0160] Hereinafter, compounds according to some example embodiments are described. In some example embodiments, the composition may include the compound. The compound is represented by Chemical Formula 1.

[0161] [Chemical Formula 1]

[0162]

[0163] In Chemical Formula 1,

[0164] R 1 to R 4 may each independently be hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C1 to C10 haloalkyl group, a C6 to C14 aryl group, or a C3 to C12 heteroaryl group,

[0165] R 11a to R 14c may each independently be hydrogen, deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C1 to C10 haloalkyl group, a C6 to C14 aryl group, a C6 to C14 aryloxy group, a C3 to C12 heteroaryl group, or a functional group represented by Chemical Formula 1A, provided that (for example, where) at least one of R 11a to R 14c is a functional group represented by Chemical Formula 1A, where R 11a to R 14c may exist independently of each other or two adjacent functional groups (for example, two adjacent ones of R 11a to R 14c , two adjacent ones of R 11a to R 14c etc.) may be connected to each other to form a fused ring with benzindole, and

[0166] n can be an integer of 1 or 2,

[0167] [Chemical Formula 1A]

[0168] ＊ -L1-(L2) m -Ar

[0169] wherein, in Chemical Formula 1A,

[0170] L1 may be a substituted or unsubstituted C2-C15 heteroaromatic ring group,

[0171] L2 may be a substituted or unsubstituted C2-C15 heteroaromatic ring group, a substituted or unsubstituted C6-C30 aromatic ring group, a substituted or unsubstituted C1-C10 alkylene group, or a substituted or unsubstituted C3-C20 cycloalkylene group,

[0172] Ar may be a substituted or unsubstituted C6-C30 aromatic ring group, a substituted or unsubstituted C2-C30 heteroaromatic ring group, a fused ring of the aromatic ring group and the heteroaromatic ring group (e.g., a fused ring of a substituted or unsubstituted C6-C30 aromatic ring group or a substituted or unsubstituted C2-C30 heteroaromatic ring group), a substituted or unsubstituted C6-C30 arylamino group, or a substituted or unsubstituted C2-C30 heteroarylamino group, and

[0173] m may be 0, 1, or 2.

[0174] Materials that absorb long-wavelength light such as infrared light need to have a small HOMO-LUMO bandgap energy. A small bandgap energy can be ensured by extending the conjugation length, but when the conjugation length increases, it may be difficult to apply a film-forming process. The compound represented by Chemical Formula 1 includes a donor benzindole (benzo[cd]indole) moiety linked to a core having an electron-withdrawing conjugated structure (squaraine (SQ) or croconaine (CR) in Chemical Formula 1), and the moiety includes a functional group represented by Chemical Formula 1A. The compound has a donor-acceptor-donor (D-A-D) structure and thus has excellent photoelectric conversion efficiency, charge transfer properties, and a small bandgap energy, and can therefore effectively absorb light in the near-infrared / infrared wavelength region (e.g., a long-wavelength region of about 750 nm to about 3000 nm and particularly greater than or equal to about 1000 nm and less than or equal to about 3000 nm). The functional group represented by Chemical Formula 1A can shift the absorption wavelength of the compound represented by Chemical Formula 1 to a longer wavelength and increase the extinction coefficient. The functional group represented by Chemical Formula 1A can easily adjust the bandgap of the compound represented by Chemical Formula 1 through various combinations of L1, L2, and Ar.

[0175] Hereinafter, the bandgap energy (which may also be interchangeably referred to as the energy bandgap) of a compound, film, layer, etc. refers to the absolute value of the difference between the HOMO energy level and the LUMO energy level of the compound, film, layer, etc.

[0176] As shown in Table 2 below, in some example embodiments, the band gap energy of the compound represented by Chemical Formula 1 or a layer, film, etc. including the compound may be between about 0.99 eV and about 1.40 eV. As shown in Table 2 below, in some example embodiments, the band gap energy of the compound represented by Chemical Formula 1 or a layer, film, etc. including the compound may be between about 0.99 eV and about 1.18 eV.

[0177] The functional group represented by Chemical Formula 1A includes a heteroaromatic ring group (L1 and optionally L2) and a (hetero)aromatic ring group (Ar), and thus can shift the absorption wavelength of the compound represented by Chemical Formula 1 to a longer wavelength and increase the extinction coefficient.

[0178] In Chemical Formula 1A, L1 and L2 may be the same or different and may each independently be a heteroaromatic ring group, and Ar may be a substituted or unsubstituted C6 to C30 aromatic ring group, a substituted or unsubstituted C2 to C30 heteroaromatic ring group, a substituted or unsubstituted C6 to C30 arylamine group, or a substituted or unsubstituted C2 to C30 heteroarylamine group.

[0179] In Chemical Formula 1A, L1 and L2 may each independently be a heteroaromatic ring group represented by one of Chemical Formulas 1A-11 to 1A-15 or a combination thereof. Here, "a combination thereof" means that two or more heteroaromatic ring groups selected from Chemical Formulas 1A-11 to 1A-15 are connected by a single bond or a substituted or unsubstituted C1 to C6 alkylene group (e.g., a methylene group).

[0180] [Chemical Formulas 1A-11 to 1A-15]

[0181]

[0182] In Chemical Formulas 1A-11 to 1A-15,

[0183] X 1 , X 2 and X 3 can be independently O, S, Se, Te, S(=O), S(=O)2, NR a 、SiR b R c or GeR d R e , where R a , R b , R c , R d and R e may each independently be hydrogen, deuterium, C1 to C10 alkyl, C1 to C10 haloalkyl, C6 to C14 aryl, C3 to C12 heteroaryl, halogen, cyano or a combination thereof, and

[0184] The hydrogen of each heteroaromatic ring may be replaced by the following: deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl, C6-C10 aryl, C6-C10 aryloxy, -SiH3 group or C1-C10 alkylsilyl.

[0185] In Chemical Formula 1A, L1 and L2 may each independently be a heteroaromatic ring group represented by one of Chemical Formulas 1A-16 to 1A-20 or a combination thereof. Herein, "a combination thereof" means that two or more heteroaromatic ring groups selected from Chemical Formulas 1A-16 to 1A-20 are connected by a single bond or a substituted or unsubstituted C1-C6 alkylene group (e.g., methylene).

[0186] [Chemical Formulas 1A-16 to 1A-20]

[0187]

[0188] In Chemical Formulas 1A-16 to 1A-20,

[0189] X 1 and X 2 may each independently be O, S, Se, Te, S(=O), S(=O)2, NR a 、SiR b R c or GeR d R e ,wherein R a 、R b 、R c 、R d and R e may each independently be hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, -SiH3 group, C1-C10 alkylsilyl, -NH2 group, C1-C10 alkylamino, C6-C10 arylamino, C6-C14 aryl, C3-C12 heteroaryl, halogen, cyano or a combination thereof,

[0190] Z 1 to Z 4 may each independently be CR x or N, wherein R x may be hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, -SiH3 group, C1-C10 alkylsilyl, -NH2 group, C1-C10 alkylamino, C6-C10 arylamino, C6-C14 aryl, C3-C12 heteroaryl, halogen, cyano or a combination thereof, or a single bond, provided that (e.g., wherein) in Chemical Formulas 1A-16 to 1A-18, one of Z 1 to Z 4 may be CR x ,wherein Rx is a single bond, and

[0191] the hydrogen of each aromatic ring and heteroaromatic ring may be substituted with the following: deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl, -SiH3 group, or C1-C10 alkylsilyl.

[0192] L1 and L2 may each independently be a combination of a heteroaromatic ring group represented by one of Chemical Formulas 1A-11 to 1A-15 and a heteroaromatic ring group represented by one of Chemical Formulas 1A-16 to 1A-20. Herein, "the combination" means that the heteroaromatic ring group represented by one of Chemical Formulas 1A-11 to 1A-15 and the heteroaromatic ring group represented by one of Chemical Formulas 1A-16 to 1A-20 are connected by a single bond or a substituted or unsubstituted C1-C6 alkylene group (e.g., methylene).

[0193] In Chemical Formula 1A, Ar is a heteroaromatic ring group represented by one of Chemical Formulas 1B-11 to 1B-15.

[0194] [Chemical Formulas 1B-11 to 1B-15]

[0195]

[0196] In Chemical Formulas 1B-11 to 1B-15,

[0197] X 1 、X 2 and X 3 may each independently be O, S, Se, Te, S(=O), S(=O)2, NR a 、SiR b R c or GeR d R e , where R a 、R b 、R c 、R d and R e may each independently be hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, C6-C14 aryl, C3-C12 heteroaryl, halogen, cyano, or a combination thereof, and

[0198] the hydrogen of each heteroaromatic ring may be replaced with the following: deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl, C6-C10 aryl, C6-C10 aryloxy, -SiH3 group, or C1-C10 alkylsilyl.

[0199] In Chemical Formula 1A, Ar may be a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C15 heteroaryl, or a fused ring thereof.

[0200] In Chemical Formula 1A, Ar may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted acenaphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted phenanthrolinyl group. In some exemplary embodiments, the substituent of Ar may be a halogen or a C1-C30 alkoxy group.

[0201] In Chemical Formula 1A, Ar may be a C6-C30 aryl group substituted with an arylamino group, a C2-C15 heteroaryl group substituted with an arylamino group, or a fused ring thereof, and the arylamino group may be represented by Chemical Formula 1C-1.

[0202] [Chemical Formula 1C-1]

[0203]

[0204] In Chemical Formula 1C-1,

[0205] Ar 21 and Ar 22 may each independently be a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group.

[0206] Chemical Formula 1C-1 may be represented by Chemical Formula 1C-1a.

[0207] [Chemical Formula 1C-1a]

[0208]

[0209] In Chemical Formula 1C-1a,

[0210] Z 1 to Z 10 may each independently be N or CR x wherein R x may be hydrogen, deuterium, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, a -SiH3 group, a C1-C10 alkylsilyl group, a -NH2 group, a C1-C10 alkylamino group, a C6-C12 aryl group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof, and

[0211] when Z 1 to Z 10 is CR x the respective R of Z 1 to Z 10 may exist independently or Z x ​1 from Z 10 to Z, at least two adjacent ones (e.g., Z 1 to Z 10 of some or all adjacent pairs) can be connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring.

[0212] In some exemplary embodiments, Z in Chemical Formula 1C-1a 2 from Z 4 to Z, at least one of and Z 7 from Z 9 to Z can be CR x , where R x can be C1-C10 haloalkyl or C1-C10 alkoxy.

[0213] In some exemplary embodiments, Z in Chemical Formula 1C-1a 3 from Z 8 to Z can be CR x , and R x can be C1-C10 haloalkyl or C1-C10 alkoxy.

[0214] Chemical Formula 1C-1a can be represented by Chemical Formulas 1C-1a-1 to 1C-1a-12.

[0215]

[0216] In Chemical Formulas 1C-1a-1 to 1C-1a-12,

[0217] a and b can each independently be an integer from 1 to 5,

[0218] c and d can each independently be an integer from 1 to 4

[0219] e can be an integer from 1 to 3,

[0220] R 3a to R 3e can independently be hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, halogen, cyano (-CN), a cyano-containing group, or a combination thereof, or optionally, when a, b, c, d, and e are 2 or greater, two adjacent ones of multiple R 3a , two adjacent ones of multiple R 3b , two adjacent ones of multiple R 3c , two adjacent ones of multiple R 3d , two adjacent ones of multiple R 3e can be connected to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

[0221] In some exemplary embodiments, Chemical Formula 1C-1 can be represented by Chemical Formula 1C-1b.

[0222] [Chemical Formula 1C-1b]

[0223]

[0224] In Chemical Formula 1C-1b,

[0225] X a and X b can each independently be -O-, -S-, -Se-, -Te-, -NR a -, -SiR b R c -, or -GeR d R e -, where R a , R b , R c , R d and R e can each independently be hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl.

[0226] Z 1 to Z 6 can each independently be N or CR x , where R x can be hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3 group, C1-C10 alkylsilyl, -NH2 group, C1-C10 alkylamino, C6-C12 aryl, C3-C12 heteroaryl, halogen, cyano, or a combination thereof, and

[0227] when Z 1 to Z 6 is CR x , the respective R 1 to Z 6 can exist independently (e.g., Z x to Z 1 to Z 6 may not be connected to each other) or at least two adjacent ones of Z 1 to Z 6 (e.g., some or all adjacent pairs of Z 1 to Z 6 ) can be connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring.

[0228] In some exemplary embodiments, at least one of Z 1 to Z 3 in Chemical Formula 1C-1b and Z 4 to Z6 At least one of them can be CR x , and R x can be C1-C10 haloalkyl or C1-C10 alkoxy.

[0229] In some exemplary embodiments, Z in Formula 1C-1b 2 to Z 5 can be CR x , where R x can be C1-C10 haloalkyl or C1-C10 alkoxy.

[0230] In Formula 1A, Ar can be a C6-C30 aryl group substituted by an N-containing heterocyclic group, a C2-C15 heteroaryl group substituted by an N-containing heterocyclic group, or a fused ring thereof, and the N-containing heterocyclic group can be represented by Formula 1C-2.

[0231] [Formula 1C-2]

[0232]

[0233] In Formula 1C-2,

[0234] Ar 23 and Ar 24 can each independently be a substituted or unsubstituted C6-C30 arene group or a substituted or unsubstituted C3-C30 heteroarene group,

[0235] G can be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h ))=C(R i ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R i can each independently be hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, where R b , R c , R d , R e , Rf , R g , R h and R i may each independently exist (e.g., may not be connected to each other to provide a ring), or R b and R c , R d and R e , R f and R g , or R h and R i may be connected to each other to provide a ring, and -(CR f R g ) n - of n may be 1 or 2.

[0236] Chemical formula 1C-2 may be represented by chemical formula 1C-2a:

[0237] [Chemical formula 1C-2a],

[0238]

[0239] In chemical formula 1C-2a,

[0240] G may be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h ))=C(R i ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R i may each independently be hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C10 aryl, where R b , R c , R d , R e , R f , R g , R h and R i may each independently exist (e.g., may not be connected to each other to provide a ring), or R b and Rc , R d and R e , R f and R g , or R h and R i may be connected to each other to provide a ring, and -(CR f R g ) n - of n may be 1 or 2,

[0241] Z 1 to Z 8 may each independently be N or CR x , where R x may be hydrogen, deuterium, C1 - C10 alkyl, C1 - C10 haloalkyl, C1 - C10 alkoxy, -SiH3 group, C1 - C10 alkylsilyl, -NH2 group, C1 - C10 alkylamino, C6 - C12 aryl, C3 - C12 heteroaryl, halogen, cyano or a combination thereof, and

[0242] when Z 1 to Z 8 is CR x , the respective R 1 to Z 8 may exist independently (e.g., Z x to Z 1 to Z 8 may not be connected to each other to provide a ring), or at least two adjacent ones of Z 1 to Z 8 may be connected to each other to form a 5 - membered aromatic ring or a 6 - membered aromatic ring.

[0243] In some example embodiments, at least one of Z 2 to Z 4 in Chemical Formula 1C - 2a and at least one of Z 6 to Z 8 may be CR x , where R x may be C1 - C10 haloalkyl or C1 - C10 alkoxy.

[0244] In some example embodiments, in Chemical Formula 1C - 2a, Z 3 and Z 7 may be CR x , where R x may be C1 - C10 haloalkyl or C1 - C10 alkoxy.

[0245] According to some example embodiments, in Chemical Formula 1C - 2a, at least one of Z 1 to Z 4 and / or at least one of Z 5from Z to Z 8 At least one of them can be N. According to some example embodiments, in Chemical Formula 1C-2a, Z 1 from Z to Z 4 At least two of them and / or Z 5 from Z to Z 8 At least two of them can be N.

[0246] Chemical Formula 1C-2a can be represented by any one of Chemical Formulas 1C-2a-1 to 1C-2a-12.

[0247]

[0248] In Chemical Formulas 1C-2a-1 to 1C-2a-12,

[0249] a and b can each independently be an integer from 1 to 4,

[0250] c and d can each independently be an integer from 1 to 3,

[0251] e is an integer of 1 or 2,

[0252] G can be a single bond, -O-, -S-, -Se-, -Te-, -N═, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h ))═C(R i ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R i can each independently be hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, where R b , R c , R d , R e , R f , R g , R h and R i can each independently exist (for example, they may not be connected to each other to form a ring), or R b and R c , R d and Re , R f and R g , or R h and R i may be connected to each other to provide a ring, and -(CR f R g ) n - of n may be 1 or 2, and

[0253] R 3a to R 3e may independently be hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, halogen, cyano (-CN), a cyano-containing group or a combination thereof, or optionally, when a, b, c, d and e are 2 or greater, two adjacent ones of multiple R 3a 's, two adjacent ones of multiple R 3b 's, two adjacent ones of multiple R 3c 's, two adjacent ones of multiple R 3d 's, two adjacent ones of multiple R 3e 's may be connected to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

[0254] Chemical formula 1C-2 may be represented by chemical formula 1C-2b:

[0255] [Chemical formula 1C-2b]

[0256]

[0257] In chemical formula 1C-2b,

[0258] G may be a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n - or -(C(R h ))=C(R i ))-, where R a , R b , R c , R d , R e , R f , R g , R h and R imay be independently hydrogen, halogen, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C10 aryl, wherein R b , R c , R d , R e , R f , R g , R h and R i may exist independently of each other (eg, may not be linked to each other to provide a ring), or R b and R c , R d and R e , R f and R g , or R h and R i can be connected to each other to provide a ring, and -(CR f R g ) n -n can be 1 or 2,

[0259] X a and X b can be independently -O-, -S-, -Se-, -Te-, -NR p -、-SiR q R r -or-GeR s R t -, where R p , R q , R r , R s and R t may be each independently hydrogen, halogen, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C10 aryl,

[0260] Z 1 To Z 4 Can be N or CR independently x , where R x may be hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C1 to C10 alkoxy group, a -SiH3 group, a C1 to C10 alkylsilyl group, a -NH2 group, a C1 to C10 alkylamino group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof, and

[0261] When Z 1 To Z 4 CR x When Z 1 To Z 4 Each R x Can exist independently (for example, Z1 from Z 4 need not be connected to each other to form a ring), or Z 1 from Z 4 at least two adjacent ones of (e.g., Z 1 from Z 4 some or all of the adjacent pairs of) may be connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring.

[0262] In some exemplary embodiments, in Chemical Formula 1C-2b, Z 1 and Z 2 at least one of and Z 3 and Z 4 at least one of may be CR x wherein R x may be C1-C10 haloalkyl or C1-C10 alkoxy.

[0263] In some exemplary embodiments, in Chemical Formula 1C-2b, Z 2 and Z 4 may be CR x wherein R x may be C1-C10 haloalkyl or C1-C10 alkoxy.

[0264] According to some exemplary embodiments, in Chemical Formula 1C-2b, Z 1 and Z 2 at least one of and / or Z 3 and Z 4 at least one of may be N. According to some exemplary embodiments, in Chemical Formula 1C-2b, Z 1 and Z 2 and / or Z 3 and Z 4 may be N.

[0265] Chemical Formula 1C-2 may be represented by Chemical Formula 1C-2c:

[0266] [Chemical Formula 1C-2c]

[0267]

[0268] In Chemical Formulas 1C-2b and 1C-2c,

[0269] G may be a single bond, -O-, -S-, -Se-, -Te-, -N═, -NR a -, -SiR b R c -, -GeR d R e -, -(CR f R g ) n-or -(C(R h ))=C(R i ))-, where R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h and R i can each independently be hydrogen, a halogen, a substituted or unsubstituted C1 - C10 alkyl group, or a substituted or unsubstituted C6 - C10 aryl group, where R b 、R c 、R d 、R e 、R f 、R g 、R h and R i can each independently exist, or R b and R c 、R d and R e 、R f and R g 、or R h and R i can be connected to each other to provide a ring, and n of -(CR f R g ) n - can be 1 or 2,

[0270] X a and X b can each independently be -O-, -S-, -Se-, -Te-, -NR p -, -SiR q R r -, or -GeR s R t -, where R p 、R q 、R r 、R s and R t can each independently be hydrogen, a halogen, a substituted or unsubstituted C1 - C10 alkyl group, or a substituted or unsubstituted C6 - C10 aryl group,

[0271] Z 1 to Z 4 can each independently be N or CR x ,where R xmay be hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3 group, C1-C10 alkylsilyl, -NH2 group, C1-C10 alkylamino, C6-C12 aryl, C3-C12 heteroaryl, halogen, cyano or a combination thereof, and

[0272] when Z 1 to Z 4 is CR x , R x may each independently exist (e.g., may not be connected to each other to provide a ring), or Z 1 to Z 4 at least two adjacent ones of (e.g., some or all adjacent pairs of Z 1 to Z 4 ) may be connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring.

[0273] In some exemplary embodiments, in Chemical Formula 1C-2c, at least one of Z 1 and Z 2 and at least one of Z 3 and Z 4 may be CR x , where R x may be C1-C10 haloalkyl or C1-C10 alkoxy.

[0274] In some exemplary embodiments, in Chemical Formula 1C-2c, Z 2 and Z 4 may be CR x , where R x may be C1-C10 haloalkyl or C1-C10 alkoxy.

[0275] According to some exemplary embodiments, in Chemical Formula 1C-2c, at least one of Z 1 and Z 2 and / or at least one of Z 3 and Z 4 may be N. According to some exemplary embodiments, in Chemical Formula 1C-2c, Z 1 and Z 2 and / or Z 3 and Z 4 may be N.

[0276] In Chemical Formula 1A, Ar may be an aromatic ring or heteroaromatic ring group represented by one of Chemical Formulas 1B-16 to 1B-25.

[0277] [Chemical Formulas 1B-16 to 1B-25]

[0278]

[0279] In Chemical Formulas 1B-16 to 1B-25,

[0280] X 1 and X 2 may each independently be O, S, Se, Te, S(=O), S(=O)2, NR a , SiR b R c or GeR d R e , where R a , R b , R c , R d and R e may each independently be hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a -SiH3 group, a C1 to C10 alkylsilyl group, a -NH2 group, a C1 to C10 alkylamino group, a C6 to C10 arylamino group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,

[0281] Z 1 to Z 4 may each independently be CR x or N, where R x may be hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a -SiH3 group, a C1 to C10 alkylsilyl group, a -NH2 group, a C1 to C10 alkylamino group, a C6 to C10 arylamino group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof, or a single bond, provided that (for example, where) in Chemical Formula 1B-20, one of Z 1 to Z 4 may be CR x , where R x may be a single bond,

[0282] Ar 11 and Ar 12 may each independently be a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group or a substituted or unsubstituted C3 to C30 heteroaromatic hydrocarbon group, and

[0283] the hydrogens of each aromatic ring and heteroaromatic ring may be replaced by the following: deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C1 to C10 haloalkyl group, a C6 to C10 aryl group, a C6 to C10 aryloxy group, a -SiH3 group, or a C1 to C10 alkylsilyl group.

[0284] Chemical Formula 1B-17 may be represented by Chemical Formula 1B-17-1 or 1B-17-2.

[0285]

[0286] In Chemical Formulas 1B-17-1 and 1B-17-2,

[0287] Z 1 to Z 6 may each independently be N or CR x , where R x may be hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3 group, C1-C10 alkylsilyl, -NH2 group, C1-C10 alkylamino, C6-C12 aryl, C3-C12 heteroaryl, halogen, cyano or a combination thereof, and

[0288] when Z 1 to Z 4 is CR x , R x may each independently exist (e.g., the respective Rs of Z 1 to Z 4 need not be connected to each other to provide a ring), or at least two adjacent ones of Z x to Z 1 to Z 4 (e.g., some or all adjacent pairs of Z 1 to Z 4 ) may be connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring.

[0289] Chemical Formula 1B-18 may be represented by Chemical Formula 1B-18-1 or 1B-18-2.

[0290]

[0291] In Chemical Formulas 1B-18-1 and 1B-18-2,

[0292] Z 1 to Z 8 may each independently be N or CR x , where R x may be hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 alkoxy, -SiH3 group, C1-C10 alkylsilyl, -NH2 group, C1-C10 alkylamino, C6-C12 aryl, C3-C12 heteroaryl, halogen, cyano or a combination thereof,

[0293] X a and X b may each independently be -O-, -S-, -Se-, -Te-, -NR p -, -SiR q R r - or -GeR s Rt -, where R p , R q , R r , R s and R t may each independently be hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,

[0294] In Chemical Formula 1B-18-1, when Z 1 to Z 8 is CR x , R x may each independently exist (for example, the respective R 1 to Z 8 need not be connected to each other to provide a ring), or at least two adjacent ones of Z x to Z 1 to Z 4 (for example, some or all of the adjacent pairs of Z 1 to Z 4 ) and / or at least two adjacent ones of Z 5 to Z 8 (for example, some or all of the adjacent pairs of Z 5 to Z 8 ) may be connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and

[0295] In Chemical Formula 1B-18-2, when Z 1 and Z 2 and / or Z 3 and Z 4 is CR x , R x may each independently exist, or Z 1 and Z 2 and / or Z 3 and Z 4 may be connected to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring.

[0296] Chemical Formula 1B-20 can be represented by Chemical Formula 1B-20-1 or 1B-20-2.

[0297]

[0298] In Chemical Formulas 1B-20-1 and 1B-20-2,

[0299] Z 1 to Z 10 may each independently be N or CR x , where R xmay be hydrogen, deuterium, a C1-C10 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, a -SiH3 group, a C1-C10 alkylsilyl group, an -NH2 group, a C1-C10 alkylamino group, a C6-C12 aryl group, a C3-C12 heteroaryl group, a halogen, a cyano group, or a combination thereof, and

[0300] when Z 5 to Z 8 is CR x , R x may each independently exist (e.g., each of R 5 to R 8 for Z x to Z 5 need not be connected to each other to provide a ring), or at least two adjacent ones of Z 8 to Z

[0301] An aryl ring or heteroaryl ring group represented by one of Chemical Formulas 1B-16 to 1B-25 (e.g., Chemical Formulas 1B-17-1, 1B-17-2, 1B-18-1, 1B-18-2, 1B-20-1, and 1B-20-2) may be substituted with an arylamino group or a heteroarylamino group, and the arylamino group and the heteroarylamino group may be represented by Chemical Formula 1C-1 above. Chemical Formula 1C-1 may be represented by at least Chemical Formula 1C-1a or 1C-1b.

[0302] An aryl ring or heteroaryl ring group represented by one of Chemical Formulas 1B-16 to 1B-25 (e.g., Chemical Formulas 1B-17-1, 1B-17-2, 1B-18-1, 1B-18-2, 1B-20-1, and 1B-20-2) may be substituted with an N-containing heterocyclic group, and the N-containing heterocyclic group may be represented by Chemical Formula 1C-2 above. Chemical Formula 1C-2 may be represented by Chemical Formula 1C-2a, 1C-2b, or 1C-2c.

[0303] In Chemical Formula 1, by including a functional group represented by Chemical Formula 1A, charge transfer characteristics can be enhanced and bandgap energy can be reduced.

[0304] When there are two or more functional groups represented by Chemical Formula 1A, they may be connected at symmetric or asymmetric positions relative to the core of the conjugated structure (squaric acid (SQ) or croconic acid (CR) in Chemical Formula 1).

[0305] In Chemical Formula 1, at least one of R 11a , R 11b , R 11c , R 12a , R 12b or R 12c may be a functional group represented by Chemical Formula 1A, and R13a , R 13b , R 13c , R 14a , R 14b or R 14c At least one of may be a functional group represented by Chemical Formula 1A.

[0306] In some exemplary embodiments, at least one of R 11a to R 11c (e.g., at least one of R 11a , R 11b or R 11c ) may be a functional group represented by Chemical Formula 1A, and at least one of R 13a to R 13c (e.g., at least one of R 13a , R 13b or R 13c ) may be a functional group represented by Chemical Formula 1A.

[0307] In some exemplary embodiments, at least one of R 12a to R 12c (e.g., at least one of R 12a , R 12b or R 12c ) may be a functional group represented by Chemical Formula 1A, and at least one of R 14a to R 14c (e.g., at least one of R 14a , R 14b or R 14c ) may be a functional group represented by Chemical Formula 1A.

[0308] In some exemplary embodiments, R 11a and R 13a may be functional groups represented by Chemical Formula 1A.

[0309] In some exemplary embodiments, R 12a and R 14a may be functional groups represented by Chemical Formula 1A.

[0310] In some exemplary embodiments, R 11a to R 14c may exist independently of each other, or two adjacent functional groups may be connected to each other to form a fused ring with benzindole.

[0311] In some exemplary embodiments, R 11a , R 11b , R 11c , R 12a , R 12b , R 12c , R 13a , R13b , R 13c , R 14a , R 14b and R 14c Two adjacent functional groups in and may be connected to each other to provide a C6 - C10 arene group (such as benzene, naphthalene, etc.), or alternatively a C3 - C10 heteroarene group (such as thiophene, pyrrole, pyridine, pyrimidine, etc.), and the arene or heteroarene group may form a fused ring with benzindole.

[0312] The compound may include a compound of Group 1.

[0313] [Group 1]

[0314]

[0315]

[0316] The compound may absorb light in the infrared wavelength region, and the compound may have a peak absorption wavelength (λ) of, for example, greater than or equal to about 750 nm, such as 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 ). For example, the compound 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 ). In some exemplary embodiments, the compound or a layer, film, etc. comprising the compound may have a peak absorption wavelength (λ) of, for example, about 1000 nm to about 3000 nm. 最大 ). In some exemplary embodiments, the compound or a layer, film, etc. comprising the compound may have a peak absorption wavelength (λ) of, for example, about 1060 nm to about 1350 nm. 最大 ).

[0317] The compound may exhibit good charge transfer properties, and thus, it has good optoelectronic conversion properties of absorbing (e.g., selectively absorbing) light and / or converting it (e.g., photoelectrically converting it) into an electrical signal, and thus can be effectively used as an optoelectronic conversion material for optoelectronic devices.

[0318] Some example embodiments provide an infrared absorber or an infrared absorption / blocking film (absorption and / or blocking film) including the compound. Again, in some example embodiments, the infrared absorber (also referred to herein as an infrared absorber composition) may include the compound as described above, and in some example embodiments, the infrared absorption / blocking film may include the compound as described above.

[0319] The compound, the infrared absorber, and the infrared absorption / blocking film can be applied to various fields that require light absorption characteristics in the infrared wavelength region.

[0320] The compound, the composition, and / or the infrared absorber have both light absorption characteristics and optoelectronic characteristics in the near-infrared wavelength region / infrared wavelength region, and thus can be effectively used as an optoelectronic conversion material.

[0321] Figure 1 is a cross-sectional view of an optoelectronic device according to some example embodiments.

[0322] Reference Figure 1 , an optoelectronic device 100 according to some example embodiments includes a first electrode 10 and a second electrode 20 facing each other and a photoactive layer 30 between the first electrode 10 and the second electrode 20. In some example embodiments, the photoactive layer 30 may be an organic layer.

[0323] 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, the following (e.g., may at least partially include the following): inorganic materials such as glass; organic materials such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, polyethersulfone, or a combination thereof; or a silicon wafer. The substrate may be omitted.

[0324] One of the first electrode 10 or 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.

[0325] At least one of the first electrode 10 or the second electrode 20 may be a light-transmissive electrode, and the light-transmissive electrode may be made of, for example, a conductive oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO2), aluminum tin oxide (AlTO), and / or fluorine-doped tin oxide (FTO); or a single-layer or multi-layer thin metal layer. When one of the first electrode 10 or the second electrode 20 is a non-light-transmissive electrode, it may be made of, for example, an opaque conductor such as aluminum (Al), silver (Ag), or gold (Au). For example, both the first electrode 10 and the second electrode 20 may be light-transmissive electrodes. For example, the second electrode 20 may be a light-receiving electrode provided on the light-receiving side.

[0326] The photoactive layer 30 is a layer including a p-type semiconductor and an n-type semiconductor configured to provide a pn junction, and is a layer that can receive light from the outside (e.g., outside the photoactive layer 30) to generate excitons, and then separate holes and electrons by the generated excitons.

[0327] The p-type semiconductor and the n-type semiconductor can 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 infrared absorber can be a p-type conductor or an n-type semiconductor. For example, the aforementioned infrared absorber and / or the compound represented by Chemical Formula 1 can be used for the p-type semiconductor, and fullerene or a fullerene derivative can be included as the n-type semiconductor. Thus, it will be understood that the photoactive layer 30 can at least partially include the above compounds, compositions, and / or infrared absorbers (e.g., can include the compound and fullerene or a fullerene derivative). Additionally, it will be understood that the photoactive layer 30 can have a peak absorption wavelength (λ 最大 ) 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, and / or a peak absorption wavelength (λ 最大 ) of 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. Based on the photoactive layer including the above infrared absorber, the photoactive layer 30 and thus the optoelectronic device 100 can have improved infrared light absorption characteristics (e.g., can have improved sensitivity to light in the infrared wavelength region, improved light absorption in the infrared wavelength region, etc.) and thus improved photoelectric conversion performance and / or efficiency and / or improved thermal stability. In some exemplary embodiments, the photoactive layer 30 can be an infrared absorption / blocking film including the infrared absorber.

[0328] The photoactive layer 30 can include an intrinsic layer (I layer), where the above infrared absorber (e.g., p-type semiconductor) and fullerene or a fullerene derivative (e.g., n-type semiconductor) can be co-deposited. Here, the p-type semiconductor and the n-type semiconductor can be included in a volume ratio of about 1:9 to about 9:1, for example, about 2:8 to about 8:2, about 3:7 to about 7:3, about 4:6 to about 6:4, or about 5:5.

[0329] In addition to the intrinsic layer, the photoactive layer 30 may further include a p-type layer and / or an n-type layer. The p-type layer may include the above-mentioned infrared absorber (e.g., a p-type semiconductor), and the n-type layer may include the above-mentioned n-type semiconductor. For example, they may be included in various combinations such as a p-type layer / I layer, an I layer / n-type layer, a p-type layer / I layer / n-type layer, etc.

[0330] The optoelectronic device 100 may further include an auxiliary layer between the first electrode 10 and the photoactive layer 30 and / or between the second electrode 20 and the photoactive layer 30. The auxiliary layer may be a charge auxiliary layer or an optical auxiliary layer.

[0331] The optoelectronic device is shown in Figure 2 in.

[0332] Figure 2 is a cross-sectional view showing an optoelectronic device according to some embodiments.

[0333] Referring to Figure 2 , an optoelectronic device 100' according to some exemplary embodiments includes a first electrode 10 and a second electrode 20 facing each other and a photoactive layer 30 between the first electrode 10 and the second electrode 20, like some exemplary embodiments including Figure 1 as shown in the exemplary embodiments.

[0334] In some exemplary embodiments including Figure 2 as shown in the exemplary embodiments, and different from some exemplary embodiments including Figure 1 as shown in the exemplary embodiments, the optoelectronic device 100' further includes charge auxiliary layers 40 and 45 between the first electrode 10 and the photoactive layer 30 and between the second electrode 20 and the photoactive layer 30, respectively. The charge auxiliary layers 40 and 45 (also referred to herein as the first and second charge auxiliary layers, respectively) facilitate the movement of holes and electrons separated by the photoactive layer 30 to increase the efficiency of the optoelectronic device 100'. In some exemplary embodiments, only one of the first charge auxiliary layer 40 or the second charge auxiliary layer 45 is included in the optoelectronic device 100'.

[0335] The charge auxiliary layers 40 and 45 may include at least one selected from the following: a hole injection layer (HIL) for promoting hole injection, a hole transport layer (HTL) for promoting hole transport, an electron blocking layer (EBL) for preventing electron transport, an electron injection layer (EIL) for promoting electron injection, an electron transport layer (ETL) for promoting electron transport, and a hole blocking layer (HBL) for preventing hole transport.

[0336] 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.

[0337] The charge assisting layers 40 and 45 may include, for example, the compound represented by Chemical Formula 1 described above and / or the above infrared absorber.

[0338] In some exemplary embodiments in which the optoelectronic device 100' includes at least one charge assisting layer (which may include one or both of the first charge assisting layer 40 or the second charge assisting layer 45), at least one of the first electrode 10, the second electrode 20, the photoactive layer 30, or the charge assisting layer may include the compound represented by Chemical Formula 1 described above.

[0339] In some exemplary embodiments, the charge assisting layer (which may include one or both of the first charge assisting layer 40 or the second charge assisting layer 45) may include the compound, and the photoactive layer 30, the first electrode 10, and the second electrode 20 may not include the compound represented by Chemical Formula 1 described above.

[0340] In some exemplary embodiments, the photoactive layer 30 may include the compound, and the charge assisting layer (which may include one or both of the first charge assisting layer 40 or the second charge assisting layer 45), the first electrode 10, and the second electrode 20 may not include the compound represented by Chemical Formula 1 described above.

[0341] In some exemplary embodiments, the optoelectronic device 100' may include both the first and second charge assisting layers 40 and 45, and at least one of the first electrode 10, the second electrode 20, the photoactive layer 30, the first charge assisting layer 40, or the second charge assisting layer 45 may include the compound represented by Chemical Formula 1 described above.

[0342] Based on at least one of one or more of the photoactive layer 30 or the charge assisting layers 40 and / or 45 including the above compound, composition, and / or infrared absorber, the charge assisting layers 40 and / or 45 and thus the optoelectronic device 100' may have improved infrared light absorption characteristics (e.g., may have improved sensitivity to light in the infrared wavelength region, improved light absorption in the infrared wavelength region, etc.) and thus improved photoelectric conversion performance and / or efficiency.

[0343] The optical assisting 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., the electrode in the optoelectronic device 100' that is close to the surrounding environment from which light is received), the optical assisting layer may be disposed on the photoactive layer 30. For example, the optical assisting layer may be disposed between the second electrode 20 and the photoactive layer 30.

[0344] The optoelectronic devices 100 and 100' 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 at the light incident side, and reduces the reflectivity of the incident light, and thus light absorption 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 47 may be disposed under the second electrode 20.

[0345] 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 at least one of, for example, metal oxides, semimetal oxides, metal sulfides, and organic materials having a refractive index within the above range. The antireflection layer may include, for example, metal oxides, chalcogen oxides, or semimetal oxides such as aluminum-containing oxides, molybdenum-containing oxides, tungsten-containing oxides, vanadium-containing oxides, rhenium-containing oxides, niobium-containing oxides, tantalum-containing oxides, titanium-containing oxides, nickel-containing oxides, copper-containing oxides, cobalt-containing oxides, manganese-containing oxides, chromium-containing oxides, tellurium-containing oxides, or combinations thereof; metal sulfides such as zinc sulfide; or organic materials such as amine derivatives, but is not limited thereto.

[0346] In the optoelectronic devices 100 and 100', when light enters the optoelectronic devices 100 and / or 100' (e.g., via) the first electrode 10 or the second electrode 20 and thus enters their photoactive layer 30, and the photoactive 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 photoactive layer 30, and the separated holes are transferred to the anode which is one of the first electrode 10 and the second electrode 20, and the separated electrons are transferred to the cathode which is the other of the first electrode 10 and the second electrode 20 to cause a current to flow (e.g., induce, generate a current, etc.).

[0347] The optoelectronic devices 100 and 100' may be applied to (e.g., be included in) sensors such as image sensors (e.g., CMOS image sensors), photodetectors, optical sensors (infrared light sensors), solar cells, etc., but the exemplary embodiments are not limited thereto.

[0348] The optoelectronic devices 100 and 100' may be applied to (e.g., be included in) sensors, and the sensors may be organic sensors. The sensors that may be organic sensors may also be organic CMOS sensors, such as organic CMOS infrared sensors or organic CMOS image sensors.

[0349] In some example embodiments, the optoelectronic device 100 may include the compound, composition, and / or infrared absorber in any of its elements, which, in addition to or as an alternative to the photoactive layer 30, includes one or more of the first electrode 10 or the second electrode 20. In some example embodiments, the optoelectronic device 100' may include the compound, composition, and / or infrared absorber in any of its elements, which, in addition to or as an alternative to one or more of the photoactive layer 30 and / or the charge assisting layer 40 / 45, includes one or more of the first electrode 10 or the second electrode 20.

[0350] Hereinafter, an image sensor including the optoelectronic device will be described with reference to the accompanying drawings.

[0351] Figure 3 is a cross-sectional view showing an image sensor according to some example embodiments.

[0352] Reference Figure 3 , an image sensor 200 according to some example embodiments includes a semiconductor substrate 110, an insulating layer 80, and an optoelectronic device 100. Figure 3 shows an image sensor 200 including Figure 1 the optoelectronic device 100, but the image sensor 200 may also include Figure 2 the optoelectronic device 100'.

[0353] The semiconductor substrate 110 may be a silicon substrate and is integrated with transfer transistors (not shown) and charge memories 55. The charge memories 55 may be integrated in each pixel. The charge memories 55 are electrically connected to the optoelectronic device 100, and the information of the charge memories 55 may be transferred by the transfer transistors.

[0354] Metal wires (not shown) and pads (not shown) are formed on the semiconductor substrate 110. To reduce signal delay, the metal wires and pads may be made of a metal having a low resistivity such as aluminum (Al), copper (Cu), silver (Ag), and their alloys, but are not limited thereto. In addition, it is not limited to the structure, and the metal wires and pads may be provided under the semiconductor substrate 110.

[0355] The insulating layer 80 is formed on the metal wires and pads. The insulating layer 80 may be made of an inorganic insulating material such as silicon oxide and / or silicon nitride, or a low dielectric constant (low-k) material such as SiC, SiCOH, SiCO, and SiOF. The insulating layer 80 has a trench 85 exposing the charge memory 55. The trench 85 may be filled with a filler.

[0356] 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, a photoactive layer 30, and a second electrode 20. Even though a structure in which the first electrode 10, the photoactive 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 photoactive layer 30, and the first electrode 10 may be arranged in this order.

[0357] Both the first electrode 10 and the second electrode 20 may be transparent electrodes, and the photoactive layer 30 may be the same as that described above with reference to Figure 1 and 2 description. The photoactive layer 30 may selectively absorb light in the infrared wavelength region. Incident light from the side of the second electrode 20 may be photoelectrically converted by mainly absorbing light in the infrared wavelength region in the photoactive layer 30. As described above with reference to Figure 1 the photoactive layer 30 may include the above-described compounds, compositions, and / or infrared absorbers, and thus may have improved sensitivity to infrared light, so that the operating performance and / or efficiency (e.g., photoelectric conversion performance and / or efficiency) of the image sensor 200 in absorbing incident infrared light and / or converting incident infrared light into an electrical signal can be improved.

[0358] 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.

[0359] Figure 4 is a cross-sectional view of an image sensor according to some example embodiments.

[0360] Reference Figure 4 , an image sensor 300 according to some example embodiments includes a semiconductor substrate 110 integrating photosensing devices (e.g., photodiodes, including silicon-based photodiodes) 50a, 50b, and 50c, a transfer transistor (not shown), and a charge memory 55, a lower insulating layer 60, color filters 70a, 70b, and 70c, an upper insulating layer 80, and an optoelectronic device 100.

[0361] The semiconductor substrate 110 may integrate photosensing devices 50a, 50b, and 50c, a transfer transistor (not shown), and a charge memory 55. The photosensing devices 50a, 50b, and 50c may be photodiodes.

[0362] The photosensing devices 50a, 50b, and 50c, the transfer transistor, and / or the charge memory 55 may be integrated in each pixel. For example, the photosensing device 50a may be included in 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.

[0363] The photosensing devices 50a, 50b, and 50c can sense (e.g., selectively absorb and / or convert (into an electrical signal, such as photoelectric conversion)) incident light, 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.

[0364] Metal wires (not shown) and pads (not shown) are formed on the semiconductor substrate 110. To reduce signal delay, the metal wires and pads can be made of a metal with 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 said structure, and the metal wires and pads can be disposed under the photosensing devices 50a and 50b.

[0365] The lower insulating layer 60 is formed on the metal wires and pads. The lower insulating layer 60 can include the same or different material compositions as the insulating layer 80.

[0366] The color filters 70a, 70b, and 70c are formed on the lower insulating layer 60. The color filters 70a, 70b, and 70c include a red color filter 70a formed in a red pixel, a green color filter 70 formed in a green pixel, and a blue color filter 70c formed in a blue pixel.

[0367] The upper insulating layer 80 is formed on the color filters 70a, 70b, and 70c. The upper insulating layer 80 eliminates the steps caused by the color filters 70a, 70b, and 70c and flattens the surface.

[0368] The above-mentioned optoelectronic device 100 is formed on the upper insulating layer 80. As described above, the optoelectronic device 100 includes a first electrode 10, a photoactive layer 30, and a second electrode 20. Even though a structure in which the first electrode 10, the photoactive 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 photoactive layer 30, and the first electrode 10 can be arranged in this order.

[0369] Both the first electrode 10 and the second electrode 20 can be transparent electrodes, and the photoactive layer 30 can be the same as the above. The photoactive layer 30 can selectively absorb light in the near-infrared / infrared wavelength region. As described above regarding the optoelectronic devices 100 and 100', any part of the optoelectronic device 100 (e.g., the first electrode 10, the second electrode 20, and / or the photoactive layer 30) can include the above-mentioned compounds, compositions, and / or infrared absorbers.

[0370] 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 photoactive 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.

[0371] As described above with reference to Figure 1 the photoactive layer 30 can include the above-mentioned compounds, compositions, and / or infrared absorbers, 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 image sensor 300 in absorbing incident infrared light and / or converting the incident infrared light into an electrical signal can be improved.

[0372] Therefore, when the image sensor 300 includes the optoelectronic device 100, the optoelectronic device 100 includes the above-mentioned compounds, compositions, and / or infrared absorbers and is configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in the first infrared wavelength region, the image sensor can include additional sensors, the additional sensors including a plurality of photodiodes (e.g., photosensing devices 50a, 50b, 50c), the plurality of photodiodes being at least partially embedded in the semiconductor substrate and configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in a separate visible wavelength region.

[0373] Figure 5 is a cross-sectional view of an image sensor according to some example embodiments.

[0374] Referring to Figure 5 , an image sensor 400 according to some example embodiments includes a semiconductor substrate 110 integrated with an infrared light charge memory 55IR, a blue light charge memory 55B, a green light charge memory 55G, a red light charge memory 55R, and a transfer transistor (not shown), a lower insulating layer 65, a blue photosensing device 100B, a green photosensing device 100G, a red photosensing device 100R, and an infrared photosensing device 100IR.

[0375] The semiconductor substrate 110 can be a silicon substrate, and the infrared light charge memory 55IR, the blue light charge memory 55B, the green light charge memory 55G, the red light charge memory 55R, and the transfer transistor (not shown) are integrated therein. The blue light charge memory 55B, the green light charge memory 55G, and the red light charge memory 55R can be integrated for each blue pixel, green pixel, and red pixel.

[0376] The charges generated in the infrared light sensing device 100IR, blue light sensing device 100B, green light sensing device 100G, and red light sensing device 100R are collected in the infrared light charge memory 55IR, blue light charge memory, green light charge memory 55G, and red light charge memory 55R, which are electrically connected to the infrared light sensing device 100IR, blue light sensing device 100B, green light sensing device 100G, and red light sensing device 100R respectively.

[0377] Metal wires (not shown) and pads (not shown) are formed on the semiconductor substrate 110. To reduce signal delay, the metal wires and pads can be made of metals with low resistivity such as aluminum (Al), copper (Cu), silver (Ag), and their alloys, but are not limited thereto.

[0378] The lower insulating layer 65 can be formed on the metal wires and pads. The lower insulating layer 65 can 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.

[0379] The blue light sensing device 100B, green light sensing device 100G, red light sensing device 100R, and red light sensing device 100IR are formed on the lower insulating layer 65. The blue light sensing device 100B can include a first electrode 10B, a second electrode 20B, and a photoactive layer 30B configured to selectively absorb light in the blue wavelength region. The green light sensing device 100G can include a first electrode 10G, a second electrode 20G, and a photoactive layer 30G configured to selectively absorb light in the green wavelength region. The red light sensing device 100R can include a first electrode 10R, a second electrode 20R, and a photoactive layer 30R configured to selectively absorb light in the red wavelength region. And the infrared light sensing device 100IR can include a first electrode 10IR, a second electrode 20IR, and a photoactive layer 30IR configured to selectively absorb light in the infrared light wavelength region.

[0380] The first electrodes 10B, 10G, 10R, and 10IR and the second electrodes 20B, 20G, 20R, and 20IR can be light-transmitting electrodes and can be made of, for example, transparent conductors such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO2), aluminum tin oxide (AlTO), and fluorine-doped tin oxide (FTO), or can be metal thin films with a thickness of several nanometers to several tens of nanometers, or metal thin films doped with metal oxides with a thickness of several nanometers to several tens of nanometers.

[0381] The photoactive layers 30B, 30G, 30R, and 30IR may include a p-type semiconductor material and an n-type semiconductor material. The photoactive layer 30B of the blue photosensing device 100B may include a p-type semiconductor material configured to selectively absorb light in the blue wavelength region and an n-type semiconductor material configured to selectively absorb light in the blue wavelength region. The photoactive layer 30G of the green photosensing device 100G may include a p-type semiconductor material configured to selectively absorb light in the green wavelength region and an n-type semiconductor material configured to selectively absorb light in the green wavelength region. The photoactive layer 30R of the red photosensing device 100R may include a p-type semiconductor material configured to selectively absorb light in the red wavelength region and an n-type semiconductor material configured to selectively absorb light in the red wavelength region. And the photoactive layer 30IR of the infrared photosensing device 100IR may include a p-type semiconductor material (e.g., the above compounds, compositions, and / or infrared absorbers) configured to selectively absorb light in the infrared region and an n-type semiconductor material configured to selectively absorb light in the infrared region. The infrared photosensing device 100IR may selectively absorb light in the infrared region greater than or equal to about 800 nm and less than or equal to about 3000 nm without absorption in the visible light region.

[0382] Figure 6 is a cross-sectional view of an image sensor according to some example embodiments. Figure 7 is a cross-sectional view of an image sensor according to some example embodiments.

[0383] Reference Figure 6 , the image sensor 500 may include a semiconductor substrate 110 integrated with an infrared photo charge memory 55IR, a blue photo charge memory 55B, a green photo charge memory 55G, a red photo charge memory 55R, and a transfer transistor (not shown), a lower insulating layer 65, an upper insulating layer 90, a blue photosensing device 100B, a green photosensing device 100G, a red photosensing device 100R, and an infrared photosensing device 100IR. The infrared photosensing device 100IR is formed on the entire front surface of the blue photosensing device 100B, the green photosensing device 100G, and the red photosensing device 100R. The remaining configuration is the same as that of the image sensor shown in Figure 5 .

[0384] In Figure 6 's configuration, the infrared photosensing device 100IR may be present on the lower insulating layer 65, and the blue photosensing device 100B, the green photosensing device 100G, and the red photosensing device 100R may be disposed thereon. The image sensor 600 having such a configuration is shown in Figure 7 .

[0385] The infrared light sensing device 100IR can be configured to selectively absorb light in the infrared region greater than or equal to about 800 nm and less than or equal to about 3000 nm, and has a large absorption area to improve efficiency.

[0386] Sensors according to some example embodiments may include multiple sensors having different functions. For example, at least one of the multiple sensors having different functions may be a biometric sensor, and the biometric sensor may be, for example, an iris sensor, a depth sensor, a fingerprint sensor, a vascular distribution sensor, etc., but is not limited thereto.

[0387] For example, one of the multiple sensors having different functions may be an iris sensor and another may be a depth sensor. The iris sensor identifies a person by using the unique iris characteristics of each person, and in particular, takes an image of the user's eyes within an appropriate distance, processes the image and compares it with his / her stored image. The depth sensor identifies the shape and position of an object from its three-dimensional information by taking an image of the object within an appropriate distance from the user and processing the image. The depth sensor may be used, for example, as a face recognition sensor.

[0388] In some example embodiments, the multiple sensors may include, for example, a first infrared light sensor configured to sense light in an infrared region having a first wavelength (λ1) in the infrared wavelength region and a second infrared light sensor configured to sense light in an infrared region having a second wavelength (λ2) in the infrared wavelength region.

[0389] The first wavelength (λ1) and the second wavelength (λ2) may be different, for example, in the wavelength region of about 800 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.

[0390] For example, one of the first wavelength (λ1) and the second wavelength (λ2) may belong to the wavelength region of about 780 nm to about 900 nm, and the other of the first wavelength (λ1) and the second wavelength (λ2) may belong to the wavelength region greater than about 900 nm and less than or equal to about 1000 nm.

[0391] For example, one of the first wavelength (λ1) and the second wavelength (λ2) may belong to the wavelength region of about 780 nm to about 840 nm, and the other of the first wavelength (λ1) and the second wavelength (λ2) may belong to the wavelength region of about 910 nm to about 970 nm.

[0392] For example, one of the first wavelength (λ1) and the second wavelength (λ2) may belong to a wavelength region of about 800 nm to about 830 nm, and the other of the first wavelength (λ1) and the second wavelength (λ2) may belong to a wavelength region of about 930 nm to about 950 nm.

[0393] For example, one of the first wavelength (λ1) and the second wavelength (λ2) may belong to a wavelength region of about 805 nm to about 815 nm, and the other of the first wavelength (λ1) and the second wavelength (λ2) may belong to a wavelength region of about 935 nm to about 945 nm.

[0394] For example, one of the first wavelength (λ1) and the second wavelength (λ2) may be about 810 nm, and the other of the first wavelength (λ1) and the second wavelength (λ2) may be about 940 nm.

[0395] Figure 8 is a cross-sectional view showing an image sensor including a plurality of sensors according to some example embodiments.

[0396] An image sensor 700 according to some example embodiments includes a dual-bandpass filter 95, a first infrared light sensor 100A, an insulating layer 80 (also referred to herein as an upper insulating layer), and a semiconductor substrate 110. The semiconductor substrate 110 is integrated with a second infrared light sensor 120 such that the second infrared light sensor 120 is at least partially embedded in the semiconductor substrate 110. The first infrared light sensor 100A and the second infrared light sensor 120 are stacked, for example, and may overlap in a vertical direction perpendicular to the upper surface 110S of the semiconductor substrate 110.

[0397] The dual-bandpass filter 95 may be disposed on the front side of the first infrared light sensor 100A and may selectively transmit infrared light including the first wavelength (λ1) and infrared light including the second wavelength (λ2), and may block and / or absorb other light. Here, the other light may include light in the ultraviolet (UV) and visible regions.

[0398] The first infrared light sensor 100A includes a first electrode 10, a photoactive layer 30, and a second electrode 20. The first infrared light sensor 100A may be the same as a photoelectric device 100 according to some example embodiments of the example embodiments including the reference Figure 1 described, but it will be understood that in some example embodiments, the first infrared light sensor 100A may be the same as a photoelectric device 100' according to some example embodiments of the example embodiments including the reference Figure 2 described.

[0399] The second infrared light sensor 120 may be integrated in the semiconductor substrate 110 (e.g., included within the volume space defined by the outer surface of the semiconductor substrate 110), and may be a light sensing device. The semiconductor substrate 110 may be, for example, a silicon substrate, and may be integrated with the second infrared light sensor 120, the charge memory 55, and a transfer transistor (not shown).

[0400] The second infrared light sensor 120 may be a photodiode, and may sense incident light, and the sensed information is transmitted by the transfer transistor. Here, the light entering the second infrared light sensor 120 is the light passing through 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 photoactive 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, for the case when all infrared light in a specific (or alternatively predetermined) region including the first wavelength (λ1) is not absorbed by the photoactive layer 30, a filter may be further provided between the first infrared light sensor 100A and the second infrared light sensor 120.

[0401] Thus, in the image sensor 700, the first infrared light sensor 100A may be understood as including a photoelectric device (e.g., the photoelectric devices 100 and / or 100') configured to sense (e.g., selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion)) light in the first infrared wavelength region (e.g., the first infrared wavelength region including the first wavelength (λ1)) of the incident light, and the second infrared light sensor 120 may be understood as an additional sensor 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 (e.g., the second infrared wavelength region different from the first near-infrared wavelength region and including the second wavelength (λ2) and not including the first wavelength (λ1)).

[0402] As described above with reference to Figure 1As described above, any part of the photoactive layer 30 or the optoelectronic device 100 and / or 100' may include the above compounds, compositions, and / or infrared absorbers, and thus may have improved sensitivity and / or absorption rate of infrared light, such that the operating performance and / or efficiency (e.g., photoelectric conversion performance and / or efficiency) of the image sensor 700 in absorbing incident infrared light and / or photoelectrically converting the incident infrared light into an electrical signal can be improved. In some exemplary embodiments, the second infrared light sensor 120 may include the above compounds, compositions, and / or infrared absorbers, and thus may have improved sensitivity and / or absorption rate of infrared light, such that the operating performance and / or efficiency (e.g., photoelectric conversion performance and / or efficiency) of the image sensor 700 in absorbing incident infrared light and / or converting the incident infrared light into an electrical signal can be improved.

[0403] A sensor according to some exemplary embodiments may include two infrared light sensors that separately perform functions, and thus may operate as a combined sensor. In some exemplary embodiments, the two sensors that separately perform functions are stacked in each pixel, and thus, while maintaining the size, the number of pixels that perform functions of each sensor is doubled, and as a result, the sensitivity can be greatly improved.

[0404] The foregoing sensor may be applied to, for example, various electronic devices, and the electronic devices may include, for example, a camera, a camcorder, a mobile phone having them therein, a display device, a security device, or a medical device, but is not limited thereto.

[0405] Figure 9 is a cross-sectional view showing an image sensor according to some exemplary embodiments.

[0406] Reference Figure 9 , an image sensor 800 according to some exemplary embodiments includes a visible light sensor 50 and an optoelectronic device 100 that is the same as the optoelectronic device in some exemplary embodiments. As Figure 9 shown, the visible light sensor 50 includes a red light sensing device 50a, a green light sensing device 50b, and a blue light sensing device 50c integrated in (e.g., at least partially embedded in) a semiconductor substrate 110, wherein the red light sensing device 50a, the green light sensing device 50b, and the blue light sensing device 50c may be photodiodes and may be configured to selectively absorb light in separate visible wavelength regions.

[0407] In an image sensor 800 according to some example embodiments, a red light sensing device 50a, a green light sensing device 50b, and a blue light sensing device 50c integrated in a semiconductor substrate 110 are stacked (e.g., overlapped with each other) in a vertical direction (e.g., the y direction, extending perpendicular to the upper surface 110S of the semiconductor substrate 110), and overlap with a photoelectric device 100 in the vertical direction. The red light sensing device 50a, the green light sensing device 50b, and the blue light sensing device 50c may be configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in respective wavelength regions depending on a stacking depth from the upper surface 110S, and thus sense it. In other words, the red light sensing device 50a configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) red light in a long wavelength region is disposed deeper from the upper surface 110S of the semiconductor substrate 110 than the blue light sensing device 50c configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) blue light in a short wavelength region, and the green light sensing device 50b configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) green light in a medium wavelength region is disposed deeper from the upper surface 110S of the semiconductor substrate 110 than the blue light sensing device 50c and closer to the upper surface 110S of the semiconductor substrate 110 than the red light sensing device 50a. In this way, by separating absorption wavelengths depending on the stacking depth, color filters 70a, 70b, and 70c may be omitted.

[0408] Figure 10 is a cross-sectional view showing an image sensor according to some example embodiments.

[0409] Reference Figure 10 , an image sensor 900 according to some example embodiments includes: a first photoelectric device (e.g., an infrared / near-infrared photoelectric device 1200d), which is configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) light in an infrared / near-infrared wavelength spectrum (e.g., a first infrared wavelength region) of incident light; and at least one additional photoelectric device (e.g., 1200a to 1200c), which is vertically stacked (e.g., in a vertical direction extending perpendicular to the upper surface 110S of the semiconductor substrate 110) between the first photoelectric device and a semiconductor substrate (e.g., 110), and each individual photoelectric device of the at least one additional photoelectric device (e.g., 1200a to 1200c) includes a separate photoelectric conversion layer and is configured to selectively absorb and / or convert (convert into an electrical signal, e.g., photoelectric conversion) a separate (e.g., respective) wavelength region of incident light that is different from the first infrared wavelength region and may be a separate visible and / or invisible wavelength region. For example, as Figure 10As shown, the image sensor 900 may include additional optoelectronic devices 1200a to 1200c, which include a red optoelectronic device 1200a 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 1200b configured to selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in the green wavelength spectrum of incident light, and a blue optoelectronic device 1200c configured to selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in the blue wavelength spectrum of incident light, and they are stacked in a vertical direction (e.g., the y direction) extending perpendicular to the upper surface 110S of the semiconductor substrate 110.

[0410] Therefore, it will be understood that, as Figure 10 shown, the image sensor 900 may include a plurality of optoelectronic devices 1200a to 1200d vertically stacked on the semiconductor substrate 110 such that the plurality of optoelectronic devices 1200a to 1200d overlap each other in a direction extending perpendicular to the upper surface 110S of the semiconductor substrate 110. Although the image sensor 900 includes a plurality of additional optoelectronic devices 1200a to 1200c in addition to a 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 image sensor 900 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.

[0411] The image sensor 900 according to some example embodiments includes a semiconductor substrate 110, a lower insulating layer 80a, an intermediate insulating layer 80b, another intermediate insulating layer 80c, an upper insulating layer 80d, a first optoelectronic device 1200a, a second optoelectronic device 1200b, a third optoelectronic device 1200c, and a fourth optoelectronic device 1200d. Each given optoelectronic device of the first to fourth optoelectronic devices 1200a to 1200d may include a first and a second electrode and a photoactive layer (e.g., 1230a to 1230d respectively) between the respective first and second electrodes of the given optoelectronic device. Each given optoelectronic device of the first to fourth optoelectronic devices 1200a to 1200d may have the same structure and / or material composition as any optoelectronic device according to any example embodiment of Figures 1 to 9 any optoelectronic device.

[0412] In some example embodiments, the fourth optoelectronic device 1200d may be referred to as a first optoelectronic device configured to selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in a 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 individual 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 with each other in a direction extending perpendicular to the upper surface 110S of the semiconductor substrate 110.

[0413] The semiconductor substrate 110 may be a silicon substrate and integrated with a transfer transistor (not shown) and a charge memory.

[0414] The first to third optoelectronic devices 1200a to 1200c may have the same structure as any optoelectronic device according to any example embodiment herein, including, without limitation, the photosensing devices 100B, 100G, and 100R shown in any one of Figures 5 - 7 , except that each individual optoelectronic device 1200a to 1200c may be configured to photoelectrically convert a separate wavelength region of visible and / or invisible (e.g., near-infrared) light, and the corresponding photoelectric conversion layers 1230a to 1230c of the first to third optoelectronic devices 1200a to 1200c may have the same structure as any optoelectronic device according to any example embodiment herein, including, without limitation, Figure 1 and 3 the optoelectronic device 100 of -4, Figure 2 the optoelectronic device 100' of Figures 5 - 7 the photosensing devices 100B, 100G, 100R, and / or 100IR shown in any one of Figure 8 and / or the first infrared light sensor 100A shown in

[0415] The fourth optoelectronic device 1200d may have the same structure as any optoelectronic device according to any example embodiment herein, including, without limitation, Figure 1 and 3The optoelectronic device 100 of -4, Figure 2 the optoelectronic device 100' of, Figures 5 - 7 the photosensing devices 100B, 100G, 100R, and / or 100IR shown in any one of, and / or Figure 8 the first infrared light sensor 100A shown in. The photoelectric conversion layer 1230d may have the same structure and / or composition as the photoactive layer according to any example embodiment described herein, including the photoactive layers 30, 30B, 30G, 30R, and / or 30IR described herein, configured to selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in different visible and / or invisible wavelength regions, and may include the compounds, compositions, and / or infrared absorbers.

[0416] The first optoelectronic device 1200a is formed on the lower insulating layer 80a. The first optoelectronic device 1200a includes a photoelectric conversion layer 1230a. The first optoelectronic device 1200a may be any one of the optoelectronic devices described herein according to any example embodiment. The photoelectric conversion layer 1230a may selectively absorb and / or convert (convert into an electrical signal, such as 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.

[0417] The intermediate insulating layer 80b is formed on the first optoelectronic device 1200a.

[0418] The second optoelectronic device 1200b is formed on the intermediate insulating layer 80b. The second optoelectronic device 1200b includes a photoelectric conversion layer 1230b. The second optoelectronic device 1200b may be any one of the optoelectronic devices described herein according to any example embodiment. The photoelectric conversion layer 1230b may selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in one of the infrared, red, blue, and green wavelength spectra of the incident light. For example, the second optoelectronic device 1200b may be a green optoelectronic device.

[0419] Another intermediate insulating layer 80c is formed on the second optoelectronic device 1200b.

[0420] 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 may be any one of the optoelectronic devices described herein according to any example embodiment. The photoelectric conversion layer 1230c may selectively absorb and / or convert (convert into an electrical signal, such as photoelectric conversion) light in one of the infrared, red, blue, and green wavelength spectra of the incident light. For example, the third optoelectronic device 1200c may be a red optoelectronic device.

[0421] The upper insulating layer 80d is formed on the third optoelectronic device 1200c.

[0422] The lower insulating layer 80a, the intermediate insulating layers 80b and 80c, and the upper insulating layer 80d have a plurality of vias or trenches 85a, 85b, 85c, and 85d that respectively expose the charge memories 55a, 55b, 55c, and 55d, and the trenches may be partially or completely filled with a filler material (e.g., a filler).

[0423] 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 may be any one of the optoelectronic devices described herein according to any example embodiment. The photoelectric conversion layer 1230d 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 fourth optoelectronic device 1200c may be an infrared / near-infrared optoelectronic device that may include the infrared absorber.

[0424] In Figure 10 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 may be stacked in various orders.

[0425] 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 image sensor may be reduced to implement a size-reduced image sensor.

[0426] Figure 11 is a block diagram of a digital camera including an image sensor according to some example embodiments.

[0427] Referring Figure 11 , 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 any example embodiment including the example embodiments shown in Figures 3 to 10 herein.

[0428] 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.

[0429] In some example embodiments, the image sensor 1020 may interface with the engine 1040.

[0430] The motor 1030 can adjust the focal length of the lens 1010 or execute the shutter in response to a control signal received from the engine 1040. The engine 1040 can control the image sensor 1020 and the motor 1030.

[0431] The engine 1040 can be connected to the host / application 1050.

[0432] Figure 12 is a block diagram of an electronic device according to some example embodiments. Refer to Figure 12 , the electronic device 1100 may include a processor 1120, a memory 1130, and an image sensor 1140 electrically coupled together via a bus 1110. The image sensor 1140 may be an image sensor according to any example embodiment of the example embodiments shown in Figures 3 - 11 . The memory 1130 (which may be a non-transitory computer-readable medium) may store instruction programs and / or other information. The memory 1130 may be non-volatile memory such as flash memory, phase change random access memory (PRAM), magnetoresistive RAM (MRAM), resistive RAM (ReRAM), or ferroelectric RAM (FRAM), or volatile memory such as static RAM (SRAM), dynamic RAM (DRAM), or synchronous DRAM (SDRAM). The processor 1120 may execute the stored instruction programs to perform 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 be configured to generate an output (e.g., an image to be displayed on a display interface) based on such processing.

[0433] The processor 1120 may include processing circuitry, such as hardware including logic circuits; a hardware / software combination, such as a processor executing software; or a combination thereof. For example, the processing circuitry may more specifically include, but is not limited to, a central processing unit (CPU), an arithmetic logic unit (ALU), a digital signal processor, a microcomputer, a field programmable gate array (FPGA), a system on a chip (SoC), a programmable logic unit, a microprocessor, an application specific integrated circuit (ASIC), etc. 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.

[0434] One or more of the processor 1120, the memory 1130, the motor 1030, the engine 1040, or the host / application 1050 may be included in, include, and / or implement one or more cases of processing circuitry, such as hardware including logic circuitry, a hardware / software combination, such as a processor that executes software; or a combination thereof. In some example embodiments, one or more cases of the processing circuitry may include, but are not limited to, a central processing unit (CPU), an application processor (AP), an arithmetic logic unit (ALU), a graphics processing unit (GPU), a digital signal processor, a microcomputer, a field programmable gate array (FPGA), a system on a chip (SoC), a programmable logic unit, a microprocessor, or an application specific integrated circuit (ASIC), etc. In some example embodiments, any memory, memory cell, etc. as described herein may include a non-transitory computer-readable storage device, such as a solid state drive (SSD), which stores an instruction program, and one or more cases of the processing circuitry may be configured to execute the instruction program to implement some or all of the functionality of the processor 1120, the memory 1130, the motor 1030, the engine 1040, or the host / application 1050, etc. according to any example embodiment as described herein.

[0435] Hereinafter, some example embodiments will be described in more detail with reference to embodiments. However, the current scope of the inventive concept is not limited to these embodiments.

[0436] Synthesis Example

[0437] Synthesis Example 1: Synthesis of the compound represented by Chemical Formula 1-1 (Compound (6))

[0438] [Chemical Formula 1-1]

[0439]

[0440] [Reaction Scheme 1-1a]

[0441]

[0442] [Reaction Scheme 1-1b]

[0443]

[0444] [Reaction Scheme 1-1c]

[0445]

[0446] i) First Step: Synthesis of Compound (1)

[0447] A solution of ethylmagnesium bromide (3 M in diethyl ether) (7.1 mL, 21.3 mmol) was slowly added to a solution of 1-octylbenzo[cd]indol-2(1H)-one (2.0 g, 7.1 mmol) dissolved in 10 mL of dry tetrahydrofuran (dry THF), and then the mixture was stirred at 60 °C for 6 hours. Subsequently, 20 mL of 1 N HCl was slowly added thereto at 0 °C, and after evaporation of THF, the remaining solution was poured into a solution of KI (2.36 g, 14.2 mmol, in 20 mL of H2O). Then, the precipitate obtained therefrom was filtered to obtain Compound (1) (1.8 g, yield: about 60%).

[0448] LC-MS: Molecular weight confirmation at 294.21 m / z.

[0449] ii) Second step: Synthesis of Compound (2)

[0450] Squaric acid (0.26 g, 2.3 mmol), thionyl chloride (1 M in MC, 4.5 mL, 4.5 mmol), and dimethylformamide (DMF, 0.04 g, 0.6 mmol) were added to toluene (8 mL), and then the mixture was stirred at 95 °C for 3 hours. Subsequently, after evaporation of thionyl chloride, Compound (1) (0.32 g, 0.8 mmol) was added thereto at room temperature, and then the mixture was stirred for 1 hour. Then, triethylamine (0.76 g, 7.5 mmol), H2O (0.55 g, 7.5 mmol), and acetone (6 mL) were added thereto, and then the mixture was continuously stirred at room temperature. After 12 hours, 30 mL of H2O was added to dissolve the materials, and the undissolved portion was removed by filtration. Finally, the pH was adjusted to 2 using 10 mL of 2N HCl, and extraction was performed with dichloromethane (MC). The resulting product was separated and purified by silica gel column chromatography (ethyl acetate (EA): n-hexane (n-Hex) = 1:1 v / v) to obtain Compound (2) (0.2 g, yield: about 68%).

[0451] LC-MS: Molecular weight confirmation at 390.28 m / z.

[0452] iii) Third step: Synthesis of Compound (3)

[0453] 6-Bromobenzo[cd]indol-2(1H)-one (3 g, 12.1 mmol) was dissolved in 60 mL of DMF, and then NaH (60% in mineral oil, 0.73 g, 18.0 mmol) was slowly added thereto, followed by stirring at 0 °C. After 1 hour, 1-bromooctane (4.7 g, 24.2 mmol) was added thereto, and then stirred at room temperature for 12 hours. When the reaction was completed, the resulting product was extracted with EA and then separated and purified by silica gel column chromatography (EA:n-Hex = 1:10 v / v) to obtain compound (3) (3.8 g, yield: about 88%).

[0454] LC-MS: Molecular weight confirmation at 360.10 m / z.

[0455] iv) Step 4: Synthesis of compound (4)

[0456] N,N-Di-p-tolyl-5-(tributylstannyl)thiophen-2-amine (3.0 g, 5.3 mmol), compound (3) (1.9 g, 5.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (5 mol%) were dissolved in 125 mL of toluene and then stirred at 110 °C for 18 hours. When the reaction was completed, after concentrating the toluene, the resulting product was separated and purified by silica gel column chromatography (EA:n-Hex = 1:10 v / v) to obtain compound (4) (2.5 g, yield: about 85%).

[0457] LC-MS: Molecular weight confirmation at 559.24 m / z.

[0458] v) Step 5: Synthesis of compound (5)

[0459] A solution of methylmagnesium chloride (3 M in THF, 0.78 mL, 2.3 mmol) was slowly added to a solution in which compound (4) (1.0 g, 1.8 mmol) was dissolved in dry tetrahydrofuran (dry THF, 6 mL), and then stirred at 60 °C for 6 hours. Subsequently, the resulting product was extracted with EA at 0 °C, and 5 mL of H2O and 1.5 mL of perchloric acid were slowly added thereto in sequence. Finally, the product produced therefrom was extracted with EA, then precipitated in hexane and filtered to obtain compound (5) (0.9 g, yield: about 76%).

[0460] LC-MS: Molecular weight confirmation at 557.25 m / z.

[0461] vi) Step 6: Synthesis of the compound represented by Chemical Formula 1-1 (compound (6))

[0462] Compound (2) (0.040 g, 0.1 mmol) and compound (5) (0.067 g, 0.1 mmol) were dissolved in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and then stirred at 80 °C for 1 hour. At the completion of the reaction, after removing the solvent, the resulting product was separated and purified by silica gel column chromatography (EA: n-Hex = 1:2 v / v) to obtain compound (6) (0.03 g, yield: about 31%).

[0463] LC-MS: Molecular weight confirmed at 928.54 m / z.

[0464] Synthesis Example 2: Synthesis of the compound (compound (10)) represented by Chemical Formula 1-2

[0465] [Chemical Formula 1-2]

[0466]

[0467] [Reaction Scheme 1-2]

[0468]

[0469] i) First step: Synthesis of compound (7)

[0470] Benz[cd]indol-2(1H)-one (1 g, 5.9 mmol) was dissolved in 24 mL of DMF, and NaH (60% in mineral oil, 0.36 g, 8.9 mmol) was slowly added thereto at 0 °C, and then stirred. After 1 hour, benzyl bromide (2.0 g, 11.8 mmol) was added thereto at room temperature, and then stirred for 12 hours. At the completion of the reaction, the resulting product was extracted with EA, and then separated and purified by silica gel column chromatography (EA: n-Hex = 1:2 v / v) to obtain compound (7) (1.5 g, yield: about 98%).

[0471] LC-MS: Molecular weight confirmed at 260.13 m / z.

[0472] ii) Second step: Synthesis of compound (8)

[0473] A solution of ethylmagnesium bromide (3 M in diethyl ether, 5.8 mL, 17.4 mmol) was slowly added to a solution in which compound (7) (1.5 g, 5.8 mmol) was dissolved in 10 mL of dry THF, and then stirred at 60 °C for 6 hours. Subsequently, 20 mL of 1 N HCl was slowly added thereto at 0 °C, and after evaporating THF, the remaining solution was poured into a solution of KI (1.92 g, 11.6 mmol, in 20 mL of H2O). Then, the precipitate formed therefrom was filtered to obtain compound (8) (0.9 g, yield: about 40%).

[0474] LC-MS: Molecular weight confirmation at 272.11 m / z.

[0475] iii) Step 3: Synthesis of compound (9)

[0476] Squaric acid (0.26 g, 2.3 mmol), thionyl chloride (1 M in MC, 4.5 mL, 4.5 mmol), and DMF (0.04 g, 0.6 mmol) were added to 8 mL of toluene, and then stirred at 95 °C for 3 hours. Subsequently, after evaporating thionyl chloride, compound (8) (0.3 g, 0.8 mmol) was added thereto at room temperature, and then stirred for 1 hour. Then, triethylamine (0.76 g, 7.5 mmol), H2O (0.55 g, 7.5 mmol), and 6 mL of acetone were added thereto, and then continuously stirred at room temperature. After 12 hours, 30 mL of H2O was added to dissolve the material, and the undissolved portion was removed by filtration. Finally, the pH was adjusted to 2 with 10 mL of 2N HCl, and extraction was performed with MC. The resulting product was separated and purified by silica gel column chromatography (EA:n-Hex = 1:1 v / v) to obtain compound (9) (0.2 g, yield: approximately 72%).

[0477] LC-MS: Molecular weight confirmation at 368.15 m / z.

[0478] iv) Step 4: Synthesis of the compound represented by Chemical Formula 1-2 (compound (10))

[0479] Compound (5) (0.067 g, 0.1 mmol) and compound (9) (0.038 g, 0.1 mmol) were dissolved in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and then stirred at 80 °C for 1 hour. At the completion of the reaction, after removing the solvent, the resulting product was separated and purified by silica gel column chromatography (EA:n-Hex = 1:2 v / v) to obtain compound (10) (0.02 g, yield: approximately 21%).

[0480] LC-MS: Molecular weight confirmation at 906.58 m / z.

[0481] Synthesis Example 3: Synthesis of the compound represented by Chemical Formula 1-3 (compound (19))

[0482] [Chemical Formula 1-3]

[0483]

[0484] [Reaction Scheme 1-3a]

[0485]

[0486] [Reaction Scheme 1-3b]

[0487]

[0488] [Reaction Scheme 1-3c]

[0489]

[0490] i) First step: Synthesis of compound (11)

[0491] Dissolve 6-bromobenzo[cd]indol-2(1H)-one (6.1 g, 24.7 mmol) and Lawesson's reagent (5.0 g, 12.4 mmol) in 250 mL of toluene, and then stir at 110 °C for 12 hours. Subsequently, lower the temperature to room temperature, and after evaporating toluene, precipitate the resulting product in H2O to obtain compound (11) (5.3 g, yield: about 82%).

[0492] LC-MS: Molecular weight confirmation at 263.85 m / z.

[0493] ii) Second step: Synthesis of compound (12)

[0494] Dissolve compound (11) (2 g, 7.6 mmol) and methyl iodide (1.3 g, 9.1 mmol) in 10 mL of 1N NaOH and 50 mL of THF, and then stir at room temperature. After 1 hour, extract with EA and evaporate to obtain compound (12) (3 g, yield: about 98%).

[0495] iii) Third step: Synthesis of compound (13)

[0496] Dissolve compound (12) (3 g, 7.4 mmol), Meldrum's acid (2 g, 13.9 mmol) and sodium acetate (1.14 g, 13.9 mmol) in 60 mL of ethanol, and then stir at 80 °C for 2 hours. Cool the resulting product to room temperature and filter to immediately obtain compound (13) (2.1 g, yield: about 75%).

[0497] iv) Fourth step: Synthesis of compound (14)

[0498] Compound (13) (1.0 g, 2.7 mmol), 1-bromooctane (1.0 g, 5.3 mmol) and potassium carbonate (0.74 g, 5.3 mmol) were dissolved in 20 mL of DMF, and then stirred at 120 °C for 8 hours. The product obtained therefrom was extracted with EA and then separated and purified by silica gel column chromatography (EA: chloroform = 1:40 v / v) to obtain compound (14) (0.53 g, yield: about 41%).

[0499] LC-MS: Molecular weight confirmation at 488.19 m / z.

[0500] v) Step 5: Synthesis of compound (15)

[0501] 4-Methyl-N,N-bis(4-(octyloxy)phenyl)-2-(trimethylstannyl)-4H-selenolo[3,2-b]indol-6-amine (3 g, 3.7 mmol), 2-bromo-3-(hexyloxy)thiophene (1.0 g, 3.7 mmol) and tetrakis(triphenylphosphine)palladium(0) (5 mol%) were dissolved in 100 mL of toluene and then stirred at 110 °C for 18 hours. When the reaction was complete, after evaporating toluene, the resulting product was separated and purified by silica gel column chromatography (EA: n-Hex = 1:20 v / v) to obtain compound (15) (0.9 g, yield: about 29%).

[0502] LC-MS: Molecular weight confirmation at 841.41 m / z.

[0503] vi) Step 6: Synthesis of compound (16)

[0504] Compound (15) (0.9 g, 1.1 mmol) was dissolved in anhydrous THF and then stirred at -78 °C. After slowly adding 2.5 M n-BuLi (in n-Hex, 0.5 mL, 1.3 mmol) thereto and then stirring the mixture for 3 hours, 1 M trimethyltin chloride (in THF, 1.3 mL, 1.3 mmol) was added thereto and then heated to room temperature. The resulting compound (compound (16), 1.0 g, yield: about 93%) was extracted with chloroform and then used in the next reaction without further purification.

[0505] LC-MS: Molecular weight confirmation at 1005.31 m / z.

[0506] vii) Step 7: Synthesis of compound (17)

[0507] Compound (14) (0.26 g, 0.54 mmol), compound (16) (0.54 g, 0.54 mmol) and tetrakis(triphenylphosphine)palladium(0) (5 mol%) were dissolved in 20 mL of toluene, and then stirred at 110 °C for 18 hours. At the completion of the reaction, after evaporation of toluene, the resulting product was separated and purified by silica gel column chromatography (EA: chloroform = 1:40 v / v) to obtain compound (17) (0.28 g, yield: about 42%).

[0508] LC-MS: Molecular weight confirmed at 1248.58 m / z.

[0509] viii) Eighth step: Synthesis of compound (18)

[0510] Compound (17) (0.1 g, 0.08 mmol) was dissolved in acetic acid (5 mL), and HCl (0.2 mL) was slowly added thereto. After the mixture was stirred at 70 °C for 1 hour, NaPF6 (0.13 g, 0.8 mmol) in 1 mL of H2O was added thereto, and the resulting precipitate was filtered to obtain compound (18) (0.09 g, yield: about 89%).

[0511] LC-MS: Molecular weight confirmed at 1118.54 m / z.

[0512] ix) Ninth step: Synthesis of the compound represented by Chemical Formula 1-3 (compound (19))

[0513] Compound (2) (0.020 g, 0.05 mmol) and compound (18) (0.065 g, 0.05 mmol) were dissolved in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and then stirred at 80 °C for 1 hour. At the completion of the reaction, after removal of the solvent, the resulting product was separated and purified by silica gel column chromatography (EA: n-Hex = 1:2 v / v) to obtain compound (19) (0.015 g, yield: about 20%).

[0514] LC-MS: Molecular weight confirmed at 1490.97 m / z.

[0515] Synthesis Example 4: Synthesis of the compound represented by Chemical Formula 1-4 (compound (22))

[0516] [Chemical Formula 1-4]

[0517]

[0518] [Reaction Scheme 1-4a]

[0519]

[0520] [Reaction Scheme 1-4b]

[0521]

[0522] i) First step: Synthesis of compound (20)

[0523] Dissolve 2,4-dihexyl-6-(3-(hexyloxy)-5-(trimethylstannyl)thiophen-2-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole (0.37 g, 0.54 mmol), compound (14) (0.26 g, 0.54 mmol) and tetrakis(triphenylphosphine)palladium(0) (5 mol%) in 20 mL of toluene, and then stir at 110 °C for 18 hours. At the completion of the reaction, after evaporating toluene, the resulting product was separated and purified by silica gel column chromatography (EA: chloroform = 1:40 v / v) to obtain compound (20) (0.35 g, yield: about 70%).

[0524] LC-MS: Molecular weight confirmed at 937.61 m / z.

[0525] i) First step: Synthesis of compound (21)

[0526] Dissolve compound (20) (0.35 g, 0.37 mmol) in 20 mL of acetic acid, and slowly add 1 mL of HCl (35%) thereto. After stirring the resulting mixture at 70 °C for 1 hour, when KI (0.13 g, 0.8 mmol, in 10 mL of H2O) was added thereto, the resulting precipitate was filtered to obtain compound (21) (0.30 g, yield: about 86%).

[0527] LC-MS: Molecular weight confirmed at 807.50 m / z.

[0528] iii) Third step: Synthesis of the compound represented by Chemical Formula 1-4 (compound (22))

[0529] Dissolve compound (2) (0.030 g, 0.08 mmol) and compound (21) (0.072 g, 0.08 mmol) in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and then stir at 80 °C for 1 hour. At the completion of the reaction, after removing the solvent, the resulting product was separated and purified by silica gel column chromatography (EA: n-Hex = 1:2 v / v) to obtain compound (22) (0.03 g, yield: about 33%).

[0530] LC-MS: Molecular weight confirmed at 1178.48 m / z.

[0531] Synthesis Example 5: Synthesis of the compound represented by Chemical Formula 1-5 (Compound (23))

[0532] [Chemical Formula 1-5]

[0533]

[0534] [Reaction Scheme 1-5]

[0535]

[0536] i) First step: Synthesis of the compound represented by Chemical Formula 1-5 (Compound (23))

[0537] Compound (21) (0.080 g, 0.09 mmol) and squaric acid (0.005 g, 0.04 mmol) were dissolved in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and then stirred at 110 °C for 1 hour. At the completion of the reaction, after evaporating the solvent, the resulting product was separated and purified by silica gel column chromatography (EA:n-Hex = 1:2 v / v) to obtain Compound (23) (0.02 g, yield: about 28%).

[0538] LC-MS: Molecular weight confirmed at 1692.90 m / z.

[0539] Synthesis Example 6: Synthesis of the compound represented by Chemical Formula 1-6 (Compound (25))

[0540] [Chemical Formula 1-6]

[0541]

[0542] [Reaction Scheme 1-6]

[0543]

[0544] i) First step: Synthesis of Compound (24)

[0545] 2-Methyl-1-octylbenzo[cd]indol-1-ium iodide (0.4 g, 1.0 mmol) and chrysophanic acid (0.2 g, 1.4 mmol) were dissolved in a mixed solvent of acetone (6 mL) and H2O (6 mL), and then stirred at room temperature for 72 hours. Subsequently, 40 mL of H2O was added thereto, and all the impurities dissolved therein were filtered off and removed. The precipitate remaining there was separated and purified by silica gel column chromatography (acetone:chloroform = 1:1 v / v) to obtain Compound (24) (0.2 g, yield: about 50%).

[0546] LC-MS: Molecular weight confirmed at 404.20 m / z.

[0547] ii) Step 2: Synthesis of the compound represented by Chemical Formula 1-6 (Compound (25))

[0548] Dissolve Compound (5) (0.067 g, 0.1 mmol) and Compound (24) (0.041 g, 0.1 mmol) in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and then stir at 110 °C for 1 hour. At the completion of the reaction, after removing the solvent, the obtained product was separated and purified by silica gel column chromatography (EA:n-Hex = 1:2 v / v) to obtain Compound (25) (0.02 g, yield: about 21%).

[0549] LC-MS: Molecular weight confirmed at 942.68 m / z.

[0550] Synthesis Example 7: Synthesis of the compound represented by Chemical Formula 1-7 (Compound (26))

[0551] [Chemical Formula 1-7]

[0552]

[0553] [Reaction Scheme 1-7]

[0554]

[0555] i) Step 1: Synthesis of the compound represented by Chemical Formula 1-7 (Compound (26))

[0556] Dissolve Compound (21) (0.070 g, 0.07 mmol) and Compound (24) (0.030 g, 0.07 mmol) in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and then stir at 110 °C for 1 hour. At the completion of the reaction, after removing the solvent, the obtained product was separated and purified by silica gel column chromatography (EA:n-Hex = 1:2 v / v) to obtain Compound (26) (0.015 g, yield: about 17%).

[0557] LC-MS: Molecular weight confirmed at 1192.44 m / z.

[0558] Synthesis Example 8: Synthesis of the compound represented by Chemical Formula 1-8 (Compound (27))

[0559] [Chemical Formula 1-8]

[0560]

[0561] [Reaction Scheme 1-8]

[0562]

[0563] i) Step 1: Synthesis of the compound represented by Chemical Formula 1-8 (Compound (27))

[0564] Dissolve Compound (21) (0.080 g, 0.09 mmol) and croconic acid (0.006 g, 0.04 mmol) in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and then stir at 110 °C for 1 hour. At the completion of the reaction, after removing the solvent, the obtained product was separated and purified by silica gel column chromatography (EA:n-Hex = 1:2 v / v) to obtain Compound (26) (0.02 g, yield: about 27%).

[0565] LC-MS: Molecular weight confirmation of 1721.76 m / z.

[0566] Synthesis of Comparative Example 1: Synthesis of the compound represented by Chemical Formula 2-1

[0567] Synthesis was carried out using the method of the reference ACS Appl. Mater. Interfaces 10, 11063 (2018).

[0568] [Chemical Formula 2-1]

[0569]

[0570] [Reaction Scheme 2-1]

[0571]

[0572] Synthesis of Comparative Example 2: Synthesis of the compound represented by Chemical Formula 2-2

[0573] [Chemical Formula 2-2]

[0574]

[0575] [Reaction Scheme 2-2]

[0576]

[0577] Dissolve 2-methyl-1-octylbenzo[cd]indol-1-ium iodide (0.4 g, 1.0 mmol) and croconic acid (0.056 g, 0.4 mmol) in acetone (6 mL) and H2O (6 mL), and then stir at room temperature for 72 hours. Subsequently, add H2O (40 mL), and filter off all the impurities dissolved therein. The precipitate remaining there was separated and purified by silica gel column chromatography (acetone:chloroform = 1:4 v / v) to obtain the compound represented by Chemical Formula 2-2 (0.13 g, yield: about 50%).

[0578] LC-MS: Molecular weight confirmation at 665.26 m / z.

[0579] Evaluation I: Light absorption characteristics

[0580] Compounds according to Synthesis Examples 1 to 8 and Synthesis Comparative Example 1 were respectively dissolved in dichloromethane at a concentration of 1×10 -5 M to prepare solutions, and the light absorption characteristics of the compounds in the solution state were evaluated. The results are shown in Table 1. The light absorption characteristics were evaluated by measuring the maximum absorption wavelength (λ 最大 ) using a UV-Vis-NIR spectrometer (UV-3600Plus, Shimadzu Corp.).

[0581] In some example embodiments, the compounds obtained in Synthesis Examples 1 to 8 and Synthesis Comparative Example 1 were respectively coated on a glass substrate by spin coating to evaluate the light absorption characteristics in the thin film state. The light absorption characteristics were evaluated by measuring the maximum absorption wavelength (λ 最大 ) using a UV-Vis-NIR spectrometer (UV-3600Plus, Shimadzu Corp.). The results are shown in Table 1.

[0582] (Table 1)

[0583] <![CDATA[λ 最大 (nm) (solution)]]> <![CDATA[λ 最大 (nm) (thin film)]]> Synthesis Example 1 972 1060 Synthesis Example 2 972 1060 Synthesis Example 3 974 1060 Synthesis Example 4 986 1065 Synthesis Example 5 1013 1100 Synthesis Example 6 1081 1200 Synthesis Example 7 1112 1210 Synthesis Example 8 1182 1350 Synthesis Comparative Example 1 884 960

[0584] Referring to Table 1, compared with the compound according to Synthesis Comparative Example 1, the compounds according to Synthesis Examples 1 to 8 exhibit superior wavelength absorption characteristics in the infrared wavelength region.

[0585] Evaluation II: Energy levels and band gaps

[0586] The HOMO energy level, LUMO energy level, and band gap energy (e.g., HOMO-LUMO band gap energy) of each thin film were evaluated by the method of the "Gaussian 09 program" based on the B3LYP / 6-31G(d) energy level theory described in "M.J. Frisch, et al., Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT 2009". The results are shown in Table 2.

[0587] (Table 2)

[0588] HOMO (eV) LUMO (eV) Band Gap Energy (eV) Synthesis Example 1 -4.60 -3.20 1.40 Synthesis Example 2 -4.60 -3.20 1.40 Synthesis Example 3 -4.41 -3.26 1.15 Synthesis Example 4 -4.52 -3.24 1.28 Synthesis Example 5 -4.52 -3.29 1.23 Synthesis Example 6 -4.66 -3.48 1.18 Synthesis Example 7 -4.61 -3.54 1.07 Synthesis Example 8 -4.52 -3.53 0.99 Synthesis Comparative Example 1 -4.80 -3.26 1.54

[0589] Referring to Table 2, the compounds of Synthesis Examples 1 to 8 have a smaller band gap energy than the compound of Synthesis Comparative Example 1, and thus can absorb light in the infrared wavelength region more effectively.

[0590] Examples and Comparative Examples: Fabrication of Optoelectronic Devices

[0591] ITO was stacked on a glass substrate by sputtering to form an anode. Subsequently, PEDOT (poly(3,4-ethylenedioxythiophene)) was coated on the anode by spin coating to form a 45-nm-thick hole transport layer. A 150-nm-thick photoactive layer (photoelectric conversion layer) was formed as follows: A solution obtained by dissolving each of the compounds according to Synthesis Examples 1 to 8 and Comparative Synthesis Examples 1 and 2 in PC70BM ([6,6]-phenyl-C71-butyric acid methyl ester) and chloroform at a mass ratio of 2.5:7.5 was spin-coated on the hole transport layer. Then, C60 was deposited on the photoactive layer to form a 30-nm-thick auxiliary layer. Then, ITO was sputtered on the auxiliary layer to form a cathode. Subsequently, the product obtained therefrom was sealed with a glass plate and annealed sequentially at 120 °C and 140 °C for 30 minutes to fabricate the optoelectronic devices according to Examples 1 to 8 and Comparative Examples 1 and 2.

[0592] Evaluation III: Photoelectric Conversion Efficiency

[0593] The photoelectric conversion efficiency (EQE) of the optoelectronic devices according to Examples 1 to 8 and Comparative Examples 1 and 2 was evaluated. The photoelectric conversion efficiency was measured using an IPCE measurement system (TNE Technology Co., Ltd., Korea). First, the system was calibrated using a Si photodiode (Hamamatsu Photonics K.K., Japan), and then installed on the optoelectronic device to measure the photoelectric conversion efficiency in the wavelength range of about 400 nm to about 1600 nm. Here, the photoelectric conversion efficiency of the optoelectronic devices according to Example 1, Example 6, and Comparative Example 1 was measured, and the results are shown in Figure 13 in.

[0594] Figure 13 is a graph showing the results of measuring the photoelectric conversion efficiency of the optoelectronic devices according to Example 1, Example 6, and Comparative Example 1.

[0595] Reference Figure 13 , compared with the optoelectronic device according to Comparative Example 1, the optoelectronic devices according to Examples 1 and 6 exhibited superior photoelectric conversion efficiency in the long-wavelength region greater than about 1000 nm. For example, as shown in Figure 13 in, the optoelectronic devices according to Examples 1 and 6 could exhibit a peak EQE (e.g., an EQE of about 1.0) in the longer wavelength region between about 1050 nm and about 1250 nm, while the optoelectronic device according to Comparative Example 1 could exhibit a peak EQE (e.g., an EQE of about 1.0) in the shorter wavelength region of about 950 nm.

[0596] Although the present disclosure has been described in connection with what are presently considered to be practical example embodiments, it will be understood that the inventive concept is not limited to these example embodiments. On the contrary, it is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

[0597] Reference numeral

[0598] 10: First electrode 20: Second electrode

[0599] 30: Photoactive layer 50a, 50b, 50c: Photosensing device

[0600] 55: Charge storage 70a, 70b, 70c: Color filter

[0601] 80: Insulating layer 100, 100': Optoelectronic device

[0602] 10B, 10G, 10R, 10IR: First electrode

[0603] 20B, 20G, 20R, 20IR: Second electrode

[0604] 30B, 30G, 30R, 30IR: Photoactive layer

[0605] 50B: Blue light charge storage 50G: Green light charge storage

[0606] 50R: Red light charge storage 50IR: Infrared light charge storage

[0607] 110: Semiconductor substrate 65: Lower insulating layer

[0608] 70a, 70b, 70c: Color filter 80: Upper insulating layer

[0609] 100B: Blue light photosensing device 100G: Green light photosensing device

[0610] 100R: Red light photosensing device

[0611] 100IR: Infrared light photosensing device

[0612] 300, 400, 500, 600, 700: Image sensor

Claims

1. A compound represented by Chemical Formula 1: [Chemical Formula 1] Among them, In Chemical Formula 1, R 1 to R 4 each independently is hydrogen, deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, or a C1-C10 haloalkyl group, R 11a to R 14c each independently is hydrogen, deuterium, a halogen, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkyl group, or a functional group represented by Chemical Formula 1A, wherein R 11a to R 14c at least one of which is a functional group represented by Chemical Formula 1A, wherein R 11a to R 14c exist independently of each other, and n is an integer of 1 or 2, [Chemical Formula 1A] *-L1-(L2) m -Ar wherein, in Chemical Formula 1A, L1 and L2 are each independently a heteroaromatic ring group represented by one of Chemical Formulas 1A-11 to 1A-13 or a heteroaromatic ring group represented by one of Chemical Formulas 1A-17 to 1A-18: [Chemical Formulas 1A-11 to 1A-13] wherein, in Chemical Formulas 1A-11 to 1A-13, X 1 and X 2 each independently is O, S, Se, or Te, and the hydrogen of each heteroaromatic ring is optionally replaced by the following: deuterium, halogen, C1-C10 alkyl, C1-C10 alkoxy, or C1-C10 haloalkyl, [Chemical Formulas 1A-17 to 1A-18] wherein, in Chemical Formulas 1A-17 to 1A-18, X 1 and X 2 each independently is O, S, Se, Te, or NR a wherein R a is hydrogen, deuterium, C1-C10 alkyl, or C1-C10 haloalkyl, Z 1 to Z 4 each independently is CR x or N, where R x is hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, or a single bond, where in Chemical Formulas 1A-17 to 1A-18, Z 1 to Z 4 one of them is CR x where R x is a single bond, and the hydrogen of each aromatic ring and heteroaromatic ring is optionally replaced by the following: deuterium, halogen, C1-C10 alkyl, C1-C10 alkoxy, or C1-C10 haloalkyl, Ar is a heteroaromatic ring group represented by one of Chemical Formulas 1B-14 to 1B-15 or a group represented by Chemical Formula 1C-1a: [Chemical Formulas 1B-14 to 1B-15] wherein, in Chemical Formulas 1B-14 to 1B-15, X 1 , X 2 and X 3 Each independently is O, S, Se, Te, or NR a , where R a is hydrogen, deuterium, C1 to C10 alkyl, or C1 to C10 haloalkyl, and the hydrogen of each heteroaromatic ring is optionally replaced by the following: deuterium, halogen, C1-C10 alkyl, C1-C10 alkoxy, or C1-C10 haloalkyl, [Chemical Formula 1C-1a] wherein, in Chemical Formula 1C-1a, Z 1 from Z to Z 10 each independently is N or CR x wherein R x is hydrogen, deuterium, C1-C10 alkyl, C1-C10 haloalkyl, or C1-C10 alkoxy, and When Z 1 to Z 10 is CR x then Z 1 to Z 10 each of the R x exists independently, and m is 0 or 1.

2. The compound according to claim 1, wherein in Chemical Formula 1, R 11a 、R 11b 、R 11c 、R 12a 、R 12b or R 12c at least one of which is a functional group represented by Chemical Formula 1A, and R 13a 、R 13b 、R 13c 、R 14a 、R 14b or R 14c At least one of which is a functional group represented by Chemical Formula 1A.

3. The compound according to claim 1, wherein in Chemical Formula 1, R 11a 、R 11b or R 11c at least one of which is a functional group represented by Chemical Formula 1A, and R 13a 、R 13b or R 13c at least one of which is a functional group represented by Chemical Formula 1A.

4. The compound according to claim 1, wherein in Chemical Formula 1, R 12a 、R 12b or R 12c at least one of which is a functional group represented by Chemical Formula 1A, and R 14a 、R 14b or R 14c at least one of which is a functional group represented by Chemical Formula 1A.

5. The compound according to claim 1, wherein R 11a and R 13a are functional groups represented by Chemical Formula 1A.

6. The compound according to claim 1, wherein R 12a and R 14a are functional groups represented by Chemical Formula 1A.

7. An infrared absorber, comprising the compound according to any one of claims 1-6.

8. An infrared absorption and / or blocking film, comprising the compound according to any one of claims 1-6.

9. An optoelectronic device, comprising: a first electrode and a second electrode facing each other; and a photoactive layer between the first electrode and the second electrode, wherein the photoactive layer comprises the compound according to any one of claims 1-6.

10. The optoelectronic device according to claim 9, wherein the photoactive layer further comprises fullerene.

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

12. An optoelectronic device, comprising: a first electrode and a second electrode facing each other; a photoactive layer between the first electrode and the second electrode; and a charge assisting layer between the photoactive layer and the first electrode or between the photoactive layer and the second electrode, wherein at least one of the first electrode, the second electrode, the photoactive layer, or the charge assisting layer comprises the compound according to any one of claims 1-6.

13. The optoelectronic device according to claim 12, wherein the charge assisting layer comprises the compound, and the photoactive layer, the first electrode, and the second electrode do not comprise the compound.

14. The optoelectronic device according to claim 12, wherein the photoactive layer comprises the compound, and the charge assisting layer, the first electrode and the second electrode do not comprise the compound.

15. The optoelectronic device according to claim 12, further comprising: a plurality of charge assisting layers, the plurality of charge assisting layers comprising the charge assisting layer, the plurality of charge assisting layers comprising a first charge assisting layer between the photoactive layer and the first electrode, and a second charge assisting layer between the photoactive layer and the second electrode, wherein at least one of the first electrode, the second electrode, the photoactive layer, the first charge assisting layer or the second charge assisting layer comprises the compound.

16. A sensor, comprising the optoelectronic device according to any one of claims 9-15.

17. An image sensor, comprising: a semiconductor substrate; a first optoelectronic device on the semiconductor substrate, the first optoelectronic device configured to selectively absorb light in a first infrared wavelength region; and an additional sensor configured to selectively absorb light in a separate wavelength region different from the first infrared wavelength region, wherein the first optoelectronic device comprises the compound according to any one of claims 1-6.

18. The image sensor according to claim 17, wherein the additional sensor is an infrared light sensor at least partially embedded in the semiconductor substrate, and the separate wavelength region is a separate infrared wavelength region different from the first infrared wavelength region, and the first optoelectronic device overlaps with the infrared light sensor in a vertical direction perpendicular to the upper surface of the semiconductor substrate.

19. The image sensor according to claim 17, wherein the additional sensor comprises a plurality of photodiodes at least partially embedded in the semiconductor substrate, the plurality of photodiodes configured to selectively absorb light in a separate visible wavelength region, and the first optoelectronic device overlaps with the plurality of photodiodes in a vertical direction perpendicular to the upper surface of the semiconductor substrate.

20. The image sensor according to claim 17, wherein the additional sensor comprises at least one additional optoelectronic device vertically stacked between the first optoelectronic device and the semiconductor substrate, each separate optoelectronic device of the at least one additional optoelectronic device comprising a separate photoelectric conversion layer and configured to selectively absorb light in a separate wavelength region different from the first infrared wavelength region.

21. The image sensor according to claim 17, wherein the first optoelectronic device comprises a first electrode and a second electrode facing each other; and a photoactive layer between the first electrode and the second electrode, wherein the photoactive layer comprises the compound.

22. The image sensor according to claim 17, wherein the first optoelectronic device comprises a first electrode and a second electrode facing each other; a photoactive layer between the first electrode and the second electrode; and a charge assisting layer between the photoactive layer and the first electrode, or between the photoactive layer and the second electrode, At least one of the first electrode, the second electrode, the photoactive layer, or the charge assisting layer includes the compound.

23. An electronic device, comprising the optoelectronic device according to any one of claims 9-15, the sensor according to claim 16, or the image sensor according to any one of claims 17-22.

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