Compounds and photoelectric elements, infrared absorbing materials, infrared absorbing / blocking films, and sensors and electronic devices containing the same

Abstract

To provide a compound with an excellent infrared absorption characteristic, and a photoelectric element, an infrared absorption material, and an infrared absorption / block film including the compound, an organic sensor including the compound or the photoelectric element, and an electronic device including the photoelectric element or the organic sensor.SOLUTION: The compound according to the present invention is represented by the following Chemical Formula 1, in which R1 to R4, R11a to R14c, and n are defined in the detailed description.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a compound, and a photoelectric element, an infrared absorbing material, an infrared absorbing / blocking film, and an organic sensor and electronic device containing the same, and in particular to a compound having excellent infrared absorbing properties, and a photoelectric element, an infrared absorbing material, an infrared absorbing / blocking film, and an organic sensor and electronic device containing the same. [Background technology]

[0002] Digital cameras and camcorders use image sensors that capture images and store them as electrical signals. The image sensor includes a sensor that separates incident light into wavelengths and converts each component into an electrical signal. In recent years, research and development of infrared photoelectric elements for improving sensor sensitivity in low-light environments or for use as biometric authentication devices has become an issue. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2015-200878 A Summary of the Invention [Problem to be solved by the invention]

[0004] The present invention has been made in consideration of the above-mentioned problems with conventional photoelectric elements, and an object of the present invention is to provide a compound having excellent infrared absorbing properties. Another object of the present invention is to provide a photoelectric element, an infrared absorbing material, and an infrared absorbing / blocking film containing the compound, as well as a sensor (e.g., an image sensor) containing the compound or the photoelectric element, and an electronic device containing the photoelectric element or the sensor. [Means for solving the problem]

[0005] The compound according to the present invention, which has been made to achieve the above object, is characterized by being represented by the following chemical formula 1. [ka] (In the above Chemical Formula 1, R 1 ~R 4 each independently represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms; R 11a ~R 14c are each independently hydrogen, deuterium, a halogen, a cyano group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a functional group represented by the following chemical formula 1A, 11a ~R 14c At least one of R is a functional group represented by the following chemical formula 1A. 11a ~R 14c are present independently of each other, or two adjacent functional groups are linked to each other to form a condensed ring with benzoindole; n is an integer of 1 or 2. [ka] (In the above Chemical Formula 1A, L 1 is a substituted or unsubstituted heteroaromatic ring group having 2 to 15 carbon atoms, L 2 is a substituted or unsubstituted heteroaromatic ring group having 2 to 15 carbon atoms, a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, Ar is a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring group having 2 to 30 carbon atoms, a fused ring thereof, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylamine group having 2 to 30 carbon atoms, m is 0, 1 or 2.

[0006] In the above Chemical Formula 1A, L 1 and L 2 are preferably each independently a heteroaromatic ring group selected from the groups represented by Chemical Formula 1A-11 to Chemical Formula 1A-15 below, or a combination thereof. [ka] (In the above Chemical Formulas 1A-11 to 1A-15, X 1 , X 2 and X 3 are each independently O, S, Se, Te, S(=O), S(=O) 2 , N.R. a , SiR b R c , or GeR d R e (where R a , R b , R c , R d , and R e are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof; The hydrogen of each heteroaromatic ring is selected from the group consisting of deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, aryl group having 6 to 10 carbon atoms, aryloxy group having 6 to 10 carbon atoms, -SiH 3 group, or an alkylsilyl group having 1 to 10 carbon atoms.)

[0007] In the above Chemical Formula 1A, L 1 and L2 are preferably each independently a heteroaromatic ring group selected from the groups represented by Chemical Formula 1A-16 to Chemical Formula 1A-20 below, or a combination thereof. [ka] (In the above Chemical Formulas 1A-16 to 1A-20, X 1 and X 2 are each independently O, S, Se, Te, S(=O), S(=O) 2 , N.R. a , SiR b R c , or GeR d R e (where R a , R b , R c , R d , and R e are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 4 are each independently x or N, where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), provided that in Chemical Formulae 1A-16 to 1A-18, Z 1 ~Z 4 One of them is CR x and R x is a single bond, The hydrogen of each aromatic ring can be replaced by deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, -SiH 3 group, or an alkylsilyl group having 1 to 10 carbon atoms. Said L 1 and L 2 are preferably each independently a combination of a heteroaromatic ring group selected from those of Chemical Formulae 1A-11 to 1A-15 and a heteroaromatic ring group selected from those of Chemical Formulae 1A-16 to 1A-20. In the above Chemical Formula 1A, Ar is preferably an aromatic ring group selected from the following Chemical Formulas 1B-11 to 1B-15. [ka] (In the above Chemical Formulae 1B-11 to 1B-15, X 1 , X 2 , and X 3 are each independently O, S, Se, Te, S(=O), S(=O) 2 ), N.R. a , SiR b R c , or GeR d R e (where R a , R b , R c , R d , and R e are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof; The hydrogen of each heteroaromatic ring is selected from the group consisting of deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, aryl group having 6 to 10 carbon atoms, aryloxy group having 6 to 10 carbon atoms, -SiH 3 group, or an alkylsilyl group having 1 to 10 carbon atoms.) In the above Chemical Formula 1A, Ar is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted acenaphthenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalyl group, a substituted or unsubstituted quinazolyl group, or a substituted or unsubstituted phenanthrolyl group.

[0008] In the above Chemical Formula 1A, Ar may be a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylamine group having 2 to 30 carbon atoms, and the above arylamine group or heteroarylamine group is preferably represented by the following Chemical Formula 1C-1. [ka] (In the above Chemical Formula 1C-1, Ar 21 and Ar 22 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0009] The above-mentioned formula 1C-1 is preferably represented by the following formula 1C-1a or 1C-1b. [ka] (In the above Chemical Formula 1C-1a, Z 1 ~Z 10 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2, an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 10 CR x In the case of R x exist independently, or Z 1 ~Z 10 adjacent two of these are linked to each other to form a 5-membered or 6-membered aromatic ring. [ka] (In the above Chemical Formula 1C-1b, X a and X b are each independently -O-, -S-, -Se-, -Te-, or -NR a -, -SiR b R c - and -GeR d R e - is selected from (where R a , R b , R c , R d and R e are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Z 1 ~Z 6 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 6 CR x In the case of R x exist independently, or Z 1~Z 6 two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0010] In the above formula 1A, Ar may be a heteroaromatic ring group, and the heteroaromatic ring group is preferably an N-containing heterocyclic group represented by the following formula 1C-2. [ka] (In the above Chemical Formula 1C-2, Ar 23 and Ar 24 are each independently selected from a substituted or unsubstituted arene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarene group having 3 to 15 carbon atoms; G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -,-GeR d R e -, -(CR f R g ) n - and -(C(R h )=C(R i ))--where R a , R b , R c , R d , R e , R f , R g , R h , and R i are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R b and R c , R d and R e , R f and R g , or R h and R i each independently may exist or may be linked to each other to form a ring; -(CR f R g ) n-n is an integer of 1 or 2.

[0011] The above-mentioned formula 1C-2 is preferably represented by the following formula 1C-2a, 1C-2b or 1C-2c. [ka] (In the chemical formula 1C-2a, G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -,-GeR d R e -, -(CR f R g ) n - and -(C(R h )=C(R i ))-selected from (where R a , R b , R c , R d , R e , R f , R g , R h , and R i are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R b and R c , R d and R e , R f and R g , or R h and R i each independently may exist or may be linked to each other to form a ring; -(CR f R g ) n - n is an integer of 1 or 2, Z 1 ~Z 8 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 8 CR x In the case of R x exist independently, or Z 1 ~Z 8 adjacent two of these are linked to each other to form a 5-membered or 6-membered aromatic ring. [ka] [ka] (In the above Chemical Formula 1C-2b and Chemical Formula 1C-2c, G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -,-GeR d R e -, -(CR f R g ) n - and -(C(R h )=C(R i ))-selected from (where R a , R b , R c , R d , R e , R f , R g , R h , and R i are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R b and R c , R d and R e , R f and R g , or R h and R ieach independently may exist or may be linked to each other to form a ring; -(CR f R g ) n - n is an integer of 1 or 2, X a and X b are each independently -O-, -S-, -Se-, -Te-, or -NR p -, -SiR q R r - and -GeR s R t - is selected from (where R p , R q , R r , R s and R t are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Z 1 ~Z 4 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 4 CR x In the case of R x exist independently, or Z 1 ~Z 4 adjacent two of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0012] In the above Chemical Formula 1A, Ar is preferably an aromatic ring group selected from the following Chemical Formulas 1B-16 to 1B-25. [ka] (In the above Chemical Formulae 1B-16 to 1B-25, X 1 and X 2 are each independently O, S, Se, Te, S(=O), S(=O) 2 , N.R. a , SiR b R ec , or GeR d R e (where R a , R b , R c , R d , and R e are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 4 are each independently x or N, where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), provided that in Chemical Formula 1B-20, Z 1 ~Z 4 One of them is CR x and R x is a single bond, Ar 11 and Ar 12 are each independently selected from a substituted or unsubstituted arene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarene group having 3 to 30 carbon atoms; The hydrogen of each aromatic ring or heteroaromatic ring is preferably selected from the group consisting of deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, aryl group having 6 to 10 carbon atoms, aryloxy group having 6 to 10 carbon atoms, -SiH 3 group, or an alkylsilyl group having 1 to 10 carbon atoms.) The aromatic ring groups represented by Chemical Formulae 1B-16 to 1B-25 are each preferably substituted with an arylamine group, and the arylamine group is preferably represented by Chemical Formula 1C-1. The formula 1C-1 is preferably represented by the formula 1C-1a or 1C-1b. The aromatic ring groups represented by the chemical formulae 1B-16 to 1B-25 are preferably substituted with an N-containing heterocyclic group, and the N-containing heterocyclic group is preferably represented by the chemical formula 1C-2. The compound represented by Chemical Formula 1C-2 is preferably represented by Chemical Formula 1C-2a, Chemical Formula 1C-2b, or Chemical Formula 1C-2c.

[0013] In the above formula 1, R 11a , R 11b , R 11c , R 12a , R 12b and R 12c At least one of R is a functional group represented by Chemical Formula 1A. 13a , R 13b , R 13c , R 14a , R 14b and R 14c At least one of them is preferably a functional group represented by Chemical Formula 1A. In the above formula 1, R 11a ~R 11c At least one of R is a functional group represented by Chemical Formula 1A. 13a ~R 13c At least one of them is preferably a functional group represented by Chemical Formula 1A. In the above formula 1, R 12a ~R 12c At least one of R is a functional group represented by Chemical Formula 1A.14a ~R 14c At least one of them is preferably a functional group represented by Chemical Formula 1A. In the above formula 1, R 11a and R 13a is preferably a functional group represented by Chemical Formula 1A. In the above formula 1, R 12a and R 14a is preferably a functional group represented by Chemical Formula 1A.

[0014] The infrared absorbing material according to the present invention, which has been made to achieve the above object, is characterized by containing the compound according to the present invention. The infrared absorbing material can exhibit a peak absorption wavelength in the wavelength region of about 750 nm to about 3000 nm.

[0015] The infrared absorbing / blocking film according to the present invention, which has been made to achieve the above object, is characterized by containing the compound of the present invention.

[0016] In order to achieve the above object, the present invention provides a photoelectric element comprising a first electrode and a second electrode facing each other, and a photoactive layer located between the first electrode and the second electrode, the photoactive layer including a compound represented by Chemical Formula 1. Another photoelectric device according to the present invention, which has been made to achieve the above object, includes a first electrode and a second electrode facing each other, a photoactive layer located between the first electrode and the second electrode, and a charge auxiliary layer between the first electrode and the photoactive layer or between the second electrode and the photoactive layer, and at least one of the first electrode, the second electrode, the photoactive layer, or the charge auxiliary layer includes a compound represented by Chemical Formula 1. The image sensor according to the present invention, which has been made to achieve the above object, includes a semiconductor substrate, a first photoelectric element located on the semiconductor substrate and configured to selectively absorb light in a first infrared wavelength region, and an additional sensor configured to selectively absorb light in another wavelength region different from the first infrared wavelength region. The first photoelectric element may include a compound represented by Formula 1 above. The additional sensor may be an infrared sensor at least partially embedded in the semiconductor substrate, and the separate wavelength range may be a separate infrared wavelength range different from the first infrared wavelength range. The first photoelectric element and the infrared sensor may overlap in a direction perpendicular to an upper surface of the semiconductor substrate. The additional sensor may include a plurality of photodiodes at least partially embedded within a semiconductor substrate, the plurality of photodiodes being configured to selectively absorb light in a separate visible wavelength region, and the first photosensitive element and the plurality of photodiodes may overlap in a direction perpendicular to a top surface of the semiconductor substrate. The additional sensor may include at least one additional photoelectric element vertically stacked between the first photoelectric element and the semiconductor substrate, and each of the at least one additional photoelectric element may include a photoelectric conversion layer and may be configured to selectively absorb light in a separate wavelength range different from the first infrared wavelength range. The first photoelectric element includes a first electrode and a second electrode facing each other, and a photoactive layer between the first electrode and the second electrode, the photoactive layer including the compound described above. The first photoelectric element includes a first electrode and a second electrode facing each other, a photoactive layer between the first electrode and the second electrode, and a charge auxiliary layer between the photoactive layer and the first electrode or between the photoactive layer and the second electrode, and at least one of the first electrode, the second electrode, the photoactive layer, or the charge auxiliary layer may include the above-mentioned compound.

[0017] The organic sensor according to the present invention, which has been made to achieve the above object, is characterized by including the photoelectric element according to the present invention.

[0018] In order to achieve the above object, the present invention provides an electronic device that includes the photoelectric element or organic sensor of the present invention. Effect of the Invention

[0019] The compound according to the present invention provides a compound that exhibits good absorption properties in the infrared region, and can be effectively used in photoelectric elements, infrared absorbing materials, infrared absorbing / blocking films, organic sensors, and electronic devices. [Brief description of the drawings]

[0020] [Figure 1] 1 is a cross-sectional view showing a schematic configuration of a photoelectric element according to an embodiment of the present invention. [Diagram 2] FIG. 11 is a cross-sectional view showing a schematic configuration of a photoelectric element according to another embodiment of the present invention. [Diagram 3] 1 is a cross-sectional view showing a schematic configuration of an image sensor according to an embodiment of the present invention. [Figure 4] FIG. 11 is a cross-sectional view showing a schematic configuration of an image sensor according to another embodiment of the present invention. [Diagram 5] FIG. 11 is a cross-sectional view showing a schematic configuration of an image sensor according to yet another embodiment of the present invention. [Figure 6] FIG. 11 is a cross-sectional view showing a schematic configuration of an image sensor according to yet another embodiment of the present invention. [Figure 7] FIG. 11 is a cross-sectional view showing a schematic configuration of an image sensor according to yet another embodiment of the present invention. [Figure 8] 1 is a cross-sectional view showing a schematic configuration of an image sensor including a plurality of sensors according to an embodiment of the present invention. [Figure 9] FIG. 11 is a cross-sectional view showing a schematic configuration of an image sensor according to yet another embodiment of the present invention. [Figure 10] FIG. 11 is a cross-sectional view showing a schematic configuration of an image sensor according to yet another embodiment of the present invention. [Figure 11] 1 is a block diagram showing a schematic configuration of a digital camera including an image sensor according to an embodiment of the present invention; [Figure 12] 1 is a block diagram showing a schematic configuration of an electronic device according to an embodiment of the present invention; [Figure 13] 1 is a graph showing the results of measuring the photoelectric conversion efficiency of the photoelectric elements of Example 1, Example 6, and Comparative Example 1. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0021] Next, specific examples of embodiments for carrying out the compound according to the present invention and the photoelectric element, infrared absorbing material, infrared absorbing / blocking film, and organic sensor and electronic device containing the compound will be described with reference to the drawings.

[0022] DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. However, actual applications may take many different forms and should not be construed as limited to the embodiments set forth herein. In the drawings, the thicknesses of the various layers and regions are exaggerated for clarity. When a part such as a layer, film, region, or plate is said to be "on" another part, this includes not only the case where it is "directly on" the other part, but also the case where there is another part between them. Conversely, when a part is said to be "directly on" another part, it means that there is no other part between them. In the drawings, in order to clearly explain the present embodiment, parts unnecessary for the explanation are omitted, and the same reference numerals are given to the same or similar components throughout the specification. As used herein, the term "combination" includes mixtures of two or more, mutual substitutions, and stacked structures of two or more.

[0023] Unless otherwise defined in this specification, "substitution" means that a hydrogen atom in a compound is replaced with a halogen, a hydroxy group, a nitro group, a cyano group, an amino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl group, a thiol group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a silyl group, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 6 to 3 carbon atoms, or a substituted or unsubstituted alkyl group having 6 to 3 carbon atoms. This means that the alkyl group is substituted with a substituent selected from an aryl group having 7 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a heteroalkyl group having 1 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a heteroarylalkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a cycloalkenyl group having 3 to 15 carbon atoms, a cycloalkynyl group having 6 to 15 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof.

[0024] Unless otherwise defined in this specification, "hetero" means containing 1 to 4 heteroatoms selected from N, O, S, Se, Te, Si, and P. Unless otherwise defined in this specification, an "aromatic ring" refers to a functional group in which all elements of a cyclic functional group have p-orbitals and these p-orbitals form conjugation, and a "heteroaromatic ring" refers to an aromatic ring containing a heteroatom. The "aromatic ring" means an arene group having 6 to 30 carbon atoms, for example, an arene group having 6 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms, for example, an aryl group having 6 to 20 carbon atoms, and the "heteroaromatic ring" can be a heteroarene group having 3 to 30 carbon atoms, for example, a heteroarene group having 3 to 20 carbon atoms, or a heteroaryl group having 6 to 30 carbon atoms, for example, a heteroaryl group having 6 to 20 carbon atoms.

[0025] Unless otherwise defined herein, an "arene group" is a hydrocarbon group having an aromatic ring, including monocyclic and polycyclic hydrocarbon groups, where the additional rings in polycyclic hydrocarbon groups can be aromatic or non-aromatic. A "heteroarene group" refers to an arene group containing from 1 to 3 heteroatoms selected from N, O, S, Se, Te, P, and Si in the ring.

[0026] Unless otherwise defined in the present specification, the term "aryl group" refers to a general concept of a group having one or more hydrocarbon aromatic moieties, and includes a form in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group, naphthyl group, etc., a form in which two or more hydrocarbon aromatic moieties are linked through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group, etc. The aryl group includes a monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) functional group.

[0027] Unless otherwise defined in this specification, a "heteroaryl group" means a group containing at least one heteroatom selected from the group consisting of N, O, S, Se, Te, P, and Si in place of carbon (C) in the ring. When a heteroaryl group is a fused ring, at least one of the rings forming the heteroaryl group contains a heteroatom, and each ring contains a heteroatom. Unless otherwise defined herein, "ring" means an aromatic ring, a non-aromatic ring, a heteroaromatic ring, a heteronon-aromatic ring, fused rings thereof, and / or combinations thereof. The aromatic ring is as described above, and the non-aromatic ring can be a cycloalkyl group having 3 to 30 carbon atoms, a cycloalkenyl group having 3 to 30 carbon atoms, or a cycloalkynyl group having 3 to 30 carbon atoms.

[0028] Unless otherwise defined in this specification, "halogen" is any one of F, Cl, Br, and I, and a haloalkyl group is an alkyl group in which at least one hydrogen is replaced with a halogen, such as -CF 3 The group may be a perfluoroalkyl group such as: Unless otherwise defined in this specification, in a substituted or unsubstituted alkylene group, a "substituted alkylene group" may have at least one hydrogen replaced with the above-mentioned substituent, or at least one methylene group replaced with -O-, -C(=O)-, -OC(=O)- or -C(=O)O-.

[0029] Furthermore, unless otherwise defined in this specification, a "cyano-containing group" may mean a monovalent functional group in which at least one hydrogen atom of a C1 to C30 alkyl group, a C2 to C30 alkenyl group, or a C2 to C30 alkynyl group is substituted with a cyano group. Also, the cyano-containing group is ═CR x '-(CR x R y ) p -CR y '(CN) 2 In some embodiments, the functional group may include a divalent functional group, such as a functional group represented by x , R y , R x ' and R y Each ' is independently hydrogen or a C1 to C10 alkyl group, and p is an integer of 0 to 10 (or 1 to 10). For example, there are a dicyanomethyl group, a dicyanomethenyl group, or a cyanomethynyl group.

[0030] Unless otherwise defined in this specification, the "infrared wavelength region" is a wavelength region from about 750 nm to about 3000 nm, including the near-infrared / infrared wavelength region.

[0031] The compounds according to one embodiment of the present invention are described below. A compound according to one embodiment of the present invention is represented by Chemical Formula 1 shown below. [ka]

[0032] In chemical formula 1, R 1 ~R 4 each independently represents a hydrogen atom, a deuterium atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms; R 11a ~R 14c are each independently hydrogen, deuterium, a halogen, a cyano group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a functional group represented by the following chemical formula 1A, 11a ~R 14c At least one of R is a functional group represented by the following chemical formula 1A. 11a ~R 14c may exist independently of each other, or two adjacent functional groups may be linked to each other to form a condensed ring with benzoindole; n is an integer of 1 or 2. [ka] In chemical formula 1A, L 1 is a substituted or unsubstituted heteroaromatic ring group having 2 to 15 carbon atoms, L 2 is a substituted or unsubstituted heteroaromatic ring group having 2 to 15 carbon atoms, a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, Ar is a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring group having 2 to 30 carbon atoms, a fused ring thereof (a fused ring of a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms and / or a substituted or unsubstituted heteroaromatic ring group having 2 to 30 carbon atoms), a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylamine group having 2 to 30 carbon atoms; m is 0, 1 or 2.

[0033] Materials that absorb long-wavelength light such as infrared rays should have a small HOMO-LUMO bandgap energy. In order to have a small band gap energy, the conjugation length is increased, but the film formation process becomes difficult when the conjugation length is increased. The compound represented by Chemical Formula 1 comprises a conjugated core (squaraine (SQ) or croconaine (CR) in Chemical Formula 1) having electron-accepting properties and an electron-donating benzo[cd]indole moiety, the moiety comprising a functional group represented by Chemical Formula 1A.

[0034] The compound has a donor-acceptor-donor (DAD) structure, which gives it excellent photoelectric conversion efficiency and charge transfer characteristics, and it has a small band gap energy and can effectively absorb light in the near-infrared / infrared wavelength region (e.g., about 750 nm to about 3000 nm, particularly in the long wavelength region of 1000 nm or more). 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, thereby increasing the extinction coefficient. The functional group represented by formula 1A is L 1 , L 2 By using various combinations of , and Ar, the band gap of the compound represented by Formula 1 can be easily tuned. Hereinafter, the energy band gap (or band gap energy) of a compound, film, layer, etc. refers to the absolute value of the difference between the HOMO energy level and the LUMO energy level. As shown in Table 2 below, in some embodiments, the energy band gap of the compound represented by Chemical Formula 1 or a layer, film, etc. including the compound may be about 0.99 eV to about 1.40 eV, for example, about 0.99 eV to about 1.18 eV.

[0035] The functional group represented by Chemical Formula 1A is a heteroaromatic ring group (L 1 and optionally L 2 ) and a (hetero)aromatic ring group (Ar), the compound represented by chemical formula 1, shifts the absorption wavelength to a longer wavelength and increases the extinction coefficient. In chemical formula 1A, L 1 and L 2 are the same or different and each independently represent a heteroaromatic ring group, and Ar can be a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring group having 2 to 30 carbon atoms, a fused ring thereof, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylamine group having 2 to 30 carbon atoms.

[0036] In chemical formula 1A, L 1 and L 2 may each independently be a heteroaromatic ring group selected from Chemical Formula 1A-11 to Chemical Formula 1A-15 shown below, or a combination thereof. Here, these combinations mean that two or more heteroaromatic ring groups selected from Chemical Formula 1A-11 to Chemical Formula 1A-15 are linked by a single bond or a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms (e.g., a methylene group). [ka]

[0037] In chemical formula 1A-11~chemical formula 1A-15, X 1 , X 2 , and X 3are each independently O, S, Se, Te, S(=O), S(=O) 2 , N.R. a , SiR b R c , or GeR d R e (where R a , R b , R c , R d , and R e each independently represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof; The hydrogen of each heteroaromatic ring is selected from the group consisting of deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, aryl group having 6 to 10 carbon atoms, aryloxy group having 6 to 10 carbon atoms, -SiH 3 group, or an alkylsilyl group having 1 to 10 carbon atoms.

[0038] In chemical formula 1A, L 1 and L 2 may each independently be a heteroaromatic ring group selected from Chemical Formulae 1A-16 to 1A-20 shown below, or a combination thereof. Here, these combinations mean that two or more heteroaromatic ring groups selected from Chemical Formulae 1A-16 to 1A-20 are linked by a single bond or a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms (e.g., a methylene group). [ka]

[0039] In chemical formula 1A-16~chemical formula 1A-20, X 1 and X 2 are each independently O, S, Se, Te, S(=O), S(=O) 2 , N.R. a , SiR b R c , or GeRd R ge (where R a , R b , R c , R d , and R e each independently represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 4 are each independently x or N, where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), provided that in Chemical Formulae 1A-16 to 1A-18, Z 1 ~Z 4 One of them is CR x and R x is a single bond, The hydrogen of each aromatic ring or heteroaromatic ring can be replaced by deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, -SiH 3 group, or an alkylsilyl group having 1 to 10 carbon atoms.

[0040] L 1 and L 2 may each independently be a combination of a heteroaromatic ring group selected from Chemical Formulae 1A-11 to 1A-15 and a heteroaromatic ring group selected from Chemical Formulae 1A-16 to 1A-20. Here, these combinations mean that a heteroaromatic ring group selected from Chemical Formulae 1A-11 to 1A-15 and a heteroaromatic ring group selected from Chemical Formulae 1A-16 to 1A-20 are linked by a single bond or a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms (e.g., a methylene group).

[0041] In Chemical Formula 1A, Ar can be a heteroaromatic ring selected from Chemical Formulas 1B-11 to 1B-15 shown below. [ka] In chemical formula 1B-11~chemical formula 1B-15, X 1 , X 2 , and X 3 are each independently O, S, Se, Te, S(=O), S(=O) 2 , N.R. a , SiR b R c , or GeR d R e (where R a , R b , R c , R d , and R e are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof; The hydrogen of each heteroaromatic ring is selected from the group consisting of deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, aryl group having 6 to 10 carbon atoms, aryloxy group having 6 to 10 carbon atoms, -SiH 3 group, or an alkylsilyl group having 1 to 10 carbon atoms.

[0042] In Chemical Formula 1A, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted acenaphthenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalyl group, a substituted or unsubstituted quinazolyl group, or a substituted or unsubstituted phenanthrolyl group. In one embodiment of the present invention, a substituent for Ar is a halogen or an alkoxy group having 1 to 30 carbon atoms.

[0043] In Chemical Formula 1A, Ar is an arylamine group or a heteroarylamine group, and the arylamine group or the heteroarylamine group is represented by Chemical Formula 1C-1 shown below. [ka] In chemical formula 1C-1, Ar 21 Ar 22 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0044] Chemical formula 1C-1 is represented by chemical formula 1C-1a shown below. [ka] In the chemical formula 1C-1a, Z 1 ~Z 10 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 10 CR x In the case of R x exist independently, or Z 1 ~Z 10 adjacent two of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0045] In one embodiment of the present invention, Z of formula 1C-1a 2 ~Z 4 At least one of and Z 7 ~Z 9 At least one of the following is CR x and R x can be a haloalkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms. In one embodiment of the present invention, Z of formula 1C-1a 3 and Z 8 CR x and R x can be a haloalkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.

[0046] Chemical formula 1C-1a is represented by the following chemical formulae 1C-1a-1 to 1C-1a-12. [ka]

[0047] In chemical formula 1C-1a-1~chemical formula 1C-1a-12, a and b are each independently an integer of 1 to 5; c and d are each independently an integer of 1 to 4. e is an integer from 1 to 3; R 3a ~R 3eare each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a halogen, a cyano group (-CN), a cyano-containing group, and combinations thereof, or optionally, when a, b, c, d, and e are 2 or more, a plurality of R 3a Two or more adjacent R 3b Two or more adjacent R 3c Two or more adjacent R 3d Two or more adjacent R 3e two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0048] Moreover, chemical formula 1C-1 is represented by chemical formula 1C-1b shown below. [ka] In the chemical formula 1C-1b, X a and X b are each independently -O-, -S-, -Se-, -Te-, or -NR a -, -SiR b R c - and -GeR d R e - (where R a , R b , R c , R d , and R e are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Z 1 ~Z 6 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 6 CR x In the case of R x exist independently, or Z 1 ~Z 6 adjacent two of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0049] In one embodiment of the present invention, Z of formula 1C-1b 1 ~Z 3 At least one of and Z 4 ~Z 6 At least one of the following is CR x and R x can be a haloalkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms. In one embodiment of the present invention, Z in formula 1C-1a 2 and Z 5 CR x and R x can be a haloalkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.

[0050] In Chemical Formula 1A, Ar may be a heteroaromatic ring group, and the heteroaromatic ring group may be an N-containing heterocyclic group represented by Chemical Formula 1C-2 shown below. [ka]

[0051] In chemical formula 1C-2, Ar 23 and Ar 24 are each independently selected from a substituted or unsubstituted arene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarene group having 3 to 15 carbon atoms; G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiRb R c -,-GeR d R e -, -(CR f R g ) n - and -(C(R h )=C(R i ))--wherein R a , R b , R c , R d , R e , R f , R g , R h , and R i are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R b and R c , R d and R e , R f and R g , or R h and R i each independently exists or are joined to each other to form a ring, -(CR f R g ) n - n is an integer of 1 or 2.

[0052] Chemical formula 1C-2 is represented by chemical formula 1C-2a shown below. [ka]

[0053] In chemical formula 1C-2a, G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -,-GeR d R e -, -(CR f R g ) n - and -(C(R h )=C(R i))--where R a , R b , R c , R d , R e , R f , R g , R h , and R i are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R b and R c , R d and R e , R f and R g , or R h and R i each independently exists or is linked to each other to form a ring; -(CR f R g ) n - n is an integer of 1 or 2, Z 1 ~Z 8 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 8 CR x In the case of R x exists independently or Z 1 ~Z 8 adjacent two of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0054] In one embodiment of the present invention, Z in formula 1C-2a 2 ~Z 4 At least one of and Z 6 ~Z 8At least one of the following is CR x and R x can be a haloalkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms. In one embodiment of the present invention, Z in formula 1C-2a 3 and Z 7 CR x and R x can be a haloalkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms. According to one embodiment of the present invention, in formula 1C-2a, Z 1 ~Z 4 At least one of and / or Z 5 ~Z 8 At least one of may be N. According to one embodiment of the present invention, in formula 1C-2a, Z 1 ~Z 4 At least two of and / or Z 5 ~Z 8 At least two of may be N.

[0055] Chemical formula 1C-2a is represented by any one of chemical formulas 1C-2a-1 to 1C-2a-12 shown below. [ka]

[0056] In chemical formula 1C-2a-1~chemical formula 1C-2a-12, a and b are each independently an integer of 1 to 4; c and d each independently represent an integer of 1 to 3; e is an integer of 1 or 2; G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -,-GeR d R e -, -(CR f R g ) n - and -(C(R h)=C(R i ))--where R a , R b , R c , R d , R e , R f , R g , R h , and R i are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R b and R c , R d and R e , R f and R g , or R h and R i each independently exists or is linked to each other to form a ring; -(CR f R g ) n - n is an integer of 1 or 2, R 3a ~R 3e are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a halogen, a cyano group (-CN), a cyano-containing group, and combinations thereof, or optionally, when a, b, c, d, and e are 2 or more, a plurality of R 3a Two or more adjacent R 3b Two or more adjacent R 3c Two or more adjacent R 3d Two or more adjacent R 3e two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0057] Chemical formula 1C-2 is represented by chemical formula 1C-2b shown below. [ka] In chemical formula 1C-2b, G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -,-GeR d R e -, -(CR f R g ) n - and -(C(R h )=C(R i ))--where R a , R b , R c , R d , R e , R f , R g , R h , and R i are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R b and R c , R d and R e , R f and R g , or R h and R i each independently exists or is linked to each other to form a ring; -(CR f R g ) n - n is an integer of 1 or 2, X a and X b are each independently -O-, -S-, -Se-, -Te-, or -NR p -, -SiR q R r - and -GeR s R t - (where R p , R q , R r , R s , and R t are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Z 1 ~Z 4are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 4 CR x In the case of R x exist independently, or Z 1 ~Z 4 adjacent two of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0058] In one embodiment of the present invention, Z in formula 1C-2b 1 and Z 2 At least one of and Z 3 and Z 4 At least one of the following is CR x and R x can be a haloalkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms. In one embodiment of the present invention, Z in formula 1C-2b 2 and Z 4 CR x and R x can be a haloalkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms. According to one embodiment of the present invention, Z in formula 1C-2b 1 and Z 2 At least one of and / or Z 3 and Z 4 At least one of may be N. According to one embodiment of the present invention, in Formula 1C-2b, Z 1 and Z 2 and / or Z 3 and Z 4 can be N.

[0059] Chemical formula 1C-2 is represented by chemical formula 1C-2c shown below. [ka]

[0060] In the chemical formula 1C-2c, G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR a -, -SiR b R c -,-GeR d R e -, -(CR f R g ) n - and -(C(R h )=C(R i ))--where R a , R b , R c , R d , R e , R f , R g , R h , and R i are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R b and R c , R d and R e , R f and R g , or R h and R i each independently exists or is linked to each other to form a ring; -(CR f R g ) n - n is an integer of 1 or 2, X a and X b are each independently -O-, -S-, -Se-, -Te-, or -NR p -, -SiR q R r - and -GeR s R t - (where R p , Rq , R r , R s , and R t are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Z 1 ~Z 4 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 4 CR x In the case of R x exists independently or Z 1 ~Z 4 adjacent two of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0061] In one embodiment of the present invention, Z in formula 1C-2c 1 and Z 2 At least one of and Z 3 and Z 4 At least one of the following is CR x and R x may be a haloalkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms. In one embodiment of the present invention, Z in formula 1C-2c 2 and Z 4 is CR x and R x may be a haloalkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms. According to one embodiment of the present invention, in Formula 1C-2c, Z 1 and Z 2 At least one of and / or Z3 and Z 4 At least one of Z may be N. According to one embodiment of the present invention, in Formula 1C-2c, 1 and Z 2 and / or Z 3 and Z 4 can be N.

[0062] In Chemical Formula 1A, Ar can be an aromatic ring group selected from Chemical Formulas 1B-16 to 1B-25 shown below. [ka]

[0063] Chemical formula 1B-16~Chemical formula 1B-25, X 1 and X 2 are each independently O, S, Se, Te, S(=O), S(=O) 2 , N.R. a , SiR b R c , or GeR d R e (where R a , R b , R c , R d , and R e are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 4 are each independently x or N, where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2, an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), provided that Z in Chemical Formula 1B-20 is 1 ~Z 4 One of them is CR x and R x is a single bond, Ar 11 and Ar 12 are each independently selected from a substituted or unsubstituted arene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarene group having 3 to 30 carbon atoms; The hydrogen of each aromatic ring or heteroaromatic ring is preferably selected from the group consisting of deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, aryl group having 6 to 10 carbon atoms, aryloxy group having 6 to 10 carbon atoms, -SiH 3 group, or an alkylsilyl group having 1 to 10 carbon atoms.

[0064] Formula 1B-17 can be formula 1B-17-1 or formula 1B-17-2 shown below. [ka] In Chemical Formula 1B-17-1 and Chemical Formula 1B-17-2, Z 1 ~Z 6 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 1 ~Z 4 CR x In the case of R xexists independently or Z 1 ~Z 4 adjacent two of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0065] Formula 1B-18 can be formula 1B-18-1 or formula 1B-18-2 shown below. [ka]

[0066] In Chemical Formula 1B-18-1 and Chemical Formula 1B-18-2, Z 1 ~Z 8 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), X a and X b are each independently -O-, -S-, -Se-, -Te-, or -NR p -, -SiR q R r - and -GeR s R t - (where R p , R q , R r , R s , and R t are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; In chemical formula 1B-18-1, Z 1 ~Z 8 CR x In the case of R x exists independently or Z 1~Z 4 Two adjacent ones of and / or Z 5 ~Z 8 two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring; In chemical formula 1B-18-2, Z 1 and Z 2 and / or Z 3 and Z 4 CR x In the case of R x exists independently or Z 1 and Z 2 and / or Z 3 and Z 4 are linked to each other to form a 5-membered or 6-membered aromatic ring.

[0067] Formula 1B-20 can be formula 1B-20-1 or formula 1B-20-2 shown below. [ka]

[0068] In Chemical Formula 1B-20-1 and Chemical Formula 1B-20-2, Z 1 ~Z 10 are each independently N or CR x (where R x is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH 3 , an alkylsilyl group having 1 to 10 carbon atoms, -NH 2 , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z 5 ~Z 8 CR x In the case of R x exists independently or Z 5 ~Z 8 adjacent two of these are linked to each other to form a 5-membered or 6-membered aromatic ring. The aromatic ring groups represented by the above chemical formulae 1B-16 to 1B-25 (for example, chemical formulae 1B-17-1, 1B-17-2, 1B-18-1, 1B-18-2, 1B-20-1 and 1B-20-2) are substituted with an arylamine group or a heteroarylamine group, and the arylamine group or the heteroarylamine group is represented by the above chemical formula 1C-1. The above chemical formula 1C-1 is represented by the above chemical formula 1C-1a or 1C-1b.

[0069] The aromatic ring groups represented by Chemical Formulae 1B-16 to 1B-25 (e.g., Chemical Formulae 1B-17-1, 1B-17-2, 1B-18-1, 1B-18-2, 1B-20-1, and 1B-20-2) are substituted with an N-containing heterocyclic group, and the N-containing heterocyclic group is represented by Chemical Formula 1C-2. Chemical formula 1C-2 is represented by chemical formula 1C-2a, chemical formula 1C-2b, or chemical formula 1C-2c.

[0070] In Chemical Formula 1, by including a functional group represented by Chemical Formula 1A, the charge transfer characteristics can be enhanced and the band gap energy can be reduced. When there are two or more functional groups represented by Formula 1A, they may be linked at symmetric or asymmetric positions relative to the core of the conjugated structure (squaraine (SQ) or croconaine (CR) in Formula 1). In chemical formula 1, R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c At least one of R is a functional group represented by Chemical Formula 1A. 13a , R 13b , R 13c , R 14a , R 14b , and R 14c At least one of may be a functional group represented by Formula 1A.

[0071] Also, R 11a ~R 11cAt least one of R is a functional group represented by Chemical Formula 1A. 13a ~R 13c At least one of may be a functional group represented by Formula 1A. Also, R 12a ~R 12c At least one of R is a functional group represented by Chemical Formula 1A. 14a ~R 14c At least one of may be a functional group represented by Formula 1A. Also, R 11a and R 13a can be a functional group represented by Formula 1A. Also, R 12a and R 14a can be a functional group represented by Formula 1A.

[0072] In one embodiment of the present invention, R 11a ~R 14c exist independently of each other, or two adjacent functional groups are linked to each other to form a condensed ring with benzoindole. In one embodiment of the present invention, R 11a , R 11b , R 11c , R 12a , R 12b , R 12c , R 13a , R 13b , R 13c , R 14a , R 14b , and R 14c Among these, two adjacent functional groups are linked to form an arene group having 6 to 10 carbon atoms (such as benzene or naphthalene) or a heteroarene group having 3 to 10 carbon atoms (such as thiophene, pyrrole, pyridine or pyrimidine), and such arene group or heteroarene group forms a condensed ring with benzoindole.

[0073] Compounds according to one embodiment of the invention may include compounds of Group 1 shown below. [ka] [ka]

[0074] The compounds of the present invention can absorb light in the infrared wavelength range, and the peak absorption wavelength (λ max ) may be, for example, about 750 nm or more, for example, about 780 nm or more, for example, about 790 nm or more, for example, about 800 nm or more, for example, about 810 nm or more, for example, about 820 nm or more, or about 830 nm or more. The peak absorption wavelength of the compound belongs to a wavelength region of, for example, about 750 nm to 3000 nm, and within the above range, belongs to a wavelength region of, for example, about 750 nm to 2500 nm, for example, about 780 nm to 2200 nm, for example, about 790 nm to 2100 nm, for example, about 800 nm to 2000 nm, for example, about 810 nm to 2000 nm, for example, about 820 nm to 2000 nm, or for example, about 830 nm to 2000 nm. In one embodiment, the compound of the present invention or a layer, film, etc. containing the compound has a peak absorption wavelength (λ ) of, for example, about 1000 nm to about 3000 nm, for example, about 1060 nm to about 1350 nm. max ).

[0075] The compound of the present invention can exhibit good charge transport properties, and therefore has good photoelectric conversion properties for absorbing light and converting it into an electrical signal, and can be effectively used as a photoelectric conversion material in a photoelectric element. Other embodiments of the present invention provide infrared absorbing materials and infrared absorbing / blocking films comprising the compounds of the present invention. The compound, infrared absorbing material, and infrared absorbing / blocking (absorbing and / or blocking) film of the present invention can be applied to various fields where absorption properties in the infrared wavelength region are required. The compound and infrared absorbing material simultaneously have light absorption properties and photoelectric properties in the near infrared / infrared wavelength region, and therefore can be effectively used as a photoelectric conversion material.

[0076] FIG. 1 is a cross-sectional view showing a schematic configuration of a photoelectric device according to one embodiment of the present invention. Referring to FIG. 1, a photoelectric device 100 according to an embodiment of the present invention includes a first electrode 10 and a second electrode 20 facing each other, and a photoactive layer 30 disposed between the first electrode 10 and the second electrode 20.

[0077] A substrate (not shown) is disposed on the first electrode 10 side or the second electrode 20 side. The substrate may be made of, for example, an inorganic material such as glass, an organic material such as polycarbonate, polymethylmethacrylate, polyethyleneterephthalate, polyethylenenaphthalate, polyamide, polyethersulfone, or combinations thereof, or a silicon wafer. The substrate may be omitted.

[0078] Either the first electrode 10 or the second electrode 20 is an anode, and the other is a cathode. For example, the first electrode 10 is an anode and the second electrode 20 is a cathode. At least one of the first electrode 10 and the second electrode 20 may be a light-transmitting electrode. The light-transmitting electrode may be made of, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO 2 ), aluminum tin oxide (AlTO), and fluorine-doped tin oxide (FTO), or thin metal films of low thickness, either in single or multiple layers. When one of the first electrode 10 and the second electrode 20 is an opaque electrode, it is made of an opaque conductor such as aluminum (Al), silver (Ag), or gold (Au), for example. As an example, the first electrode 10 and the second electrode 20 may both be light-transmitting electrodes. As an example, the second electrode 20 may be a light receiving electrode located on the side receiving light.

[0079] The photoactive layer 30 is a layer where a p-type semiconductor and an n-type semiconductor form a pn junction. When exposed to light from the outside, the photoactive layer 30 generates excitons and then separates the generated excitons into holes and electrons. The p-type semiconductor and the n-type semiconductor are light-absorbing substances that absorb light in at least a certain wavelength region, and the compound represented by the above-mentioned Chemical Formula 1 or the infrared absorbing material can be used as the p-type semiconductor or the n-type semiconductor. As an example, the compound or infrared absorbing material represented by the above-mentioned Chemical Formula 1 can be used as a p-type semiconductor, and can include a fullerene or a fullerene derivative as an n-type semiconductor. Thus, the photoactive layer 30 has a peak absorption wavelength (λ) in a wavelength region of, for example, about 750 nm or more, about 780 nm or more, about 790 nm or more, about 800 nm or more, about 810 nm or more, about 820 nm or more, or about 830 nm or more, for example, about 750 nm to 3000 nm, about 750 nm to 2500 nm, about 780 nm to 2200 nm, about 790 nm to 2100 nm, about 800 nm to 2000 nm, about 810 nm to 2000 nm, about 820 nm to 2000 nm, or about 830 nm to 2000 nm. max ) can be shown. The photoactive layer 30 includes an intrinsic layer including a p-type semiconductor and an n-type semiconductor, where the p-type semiconductor and the n-type semiconductor are included in a volume ratio of about 1:9 to 9:1, within the above range, for example, about 2:8 to 8:2, within the above range, for example, about 3:7 to 7:3, within the above range, for example, about 4:6 to 6:4, within the above range, and for example, about 5:5, within the above range.

[0080] In addition to the intrinsic layer, the photoactive layer 30 further includes a p-type layer and / or an n-type layer. The p-type layer includes the p-type semiconductor described above, and the n-type layer includes the n-type semiconductor described above. For example, various combinations such as p-type layer / I layer, I layer / n-type layer, and p-type layer / I layer / n-type layer are included. The photovoltaic device 100 further includes an auxiliary layer disposed 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.

[0081] A photoelectric element 100' having such a structure is shown in FIG. FIG. 2 is a cross-sectional view showing a schematic configuration of a photoelectric device according to another embodiment of the present invention. Referring to FIG. 2, the photoelectric device 100′ according to this embodiment includes a first electrode 10 and a second electrode 20 facing each other, and a photoactive layer 30 located between the first electrode 10 and the second electrode 20, similar to the above-described embodiments. However, unlike the above-described embodiments, the photoelectric device 100' according to this embodiment further includes charge auxiliary layers (40, 45) between the first electrode 10 and the photoactive layer 30 and between the second electrode 20 and the photoactive layer 30, respectively.

[0082] The charge auxiliary layers (40, 45) facilitate the movement of holes and electrons separated in the photoactive layer 30 to increase efficiency. The charge auxiliary layer (40, 45) includes at least one selected from a hole injecting layer (HIL) that facilitates the injection of holes, a hole transporting layer (HTL) that facilitates the transport of holes, an electron blocking layer (EBL) that blocks the movement of electrons, an electron injecting layer (EIL) that facilitates the injection of electrons, an electron transporting layer (ETL) that facilitates the transport of electrons, and a hole blocking layer (HBL) that blocks the movement of holes. The charge auxiliary layer (40, 45) may, for example, be organic, inorganic, or organic-inorganic. The organic materials are organic compounds that have hole or electronic properties, and the inorganic materials are metal oxides such as molybdenum oxide, tungsten oxide, nickel oxide, and the like. The charge auxiliary layers (40, 45) include, for example, the infrared absorbing material described above. In one embodiment, the photoelectric device 100' includes at least one charge auxiliary layer (at least one of the first charge auxiliary layer 40 and the second charge auxiliary layer 45), and at least one of the first electrode 10, the second electrode 20, the photoactive layer 30, or the charge auxiliary layer may include a compound represented by the above-mentioned Chemical Formula 1. Charge auxiliary layers 40 and / or 45 may contain a compound of the present invention, and first electrode 10, second electrode 20, and photoactive layer 30 may not contain a compound of the present invention. The charge auxiliary layers 40 and / or 45 and the photoactive layer 30 may contain a compound of the present invention, while the first electrode 10 and the second electrode 20 may not contain a compound of the present invention. The photoactive layer 30 may include a compound of the present invention, and the first electrode 10, the second electrode 20, and the charge auxiliary layers 40 and / or 45 may not include a compound of the present invention.

[0083] The optical auxiliary layer is located in the light incident direction of the photoelectric element, for example, on top of the photoactive layer 30 when the second electrode 20 is a light receiving electrode. For example, the optical auxiliary layer is disposed between the second electrode 20 and the photoactive layer 30 .

[0084] The photoelectric element (100, 100') further includes an anti-reflection layer 47 on one side of the first electrode 10 or the second electrode 20. The anti-reflection layer can be disposed on the light incident side to reduce the reflectance of the incident light, thereby further improving the light absorption. For example, when light is incident on the first electrode 10 side, the anti-reflection layer 47 is disposed on one side of the first electrode 10, and when light is incident on the second electrode 20 side, the anti-reflection layer is disposed on one side of the second electrode 20. The anti-reflection layer 47 may include a material having a refractive index of, for example, about 1.6 to 2.5, and may include, for example, at least one of a metal oxide, a chalcogen oxide, a semi-metal oxide, a metal sulfide, and an organic material having a refractive index in the above range.

[0085] The antireflective layer can include, but is not limited to, for example, metal oxides or semi-metal oxides such as aluminum-containing oxides, molybdenum-containing oxides, tungsten-containing oxides, vanadium-containing oxides, rhenium-containing oxides, niobium-containing oxides, tantalum-containing oxides, titanium-containing oxides, nickel-containing oxides, copper-containing oxides, cobalt-containing oxides, manganese-containing oxides, chromium-containing oxides, tellurium-containing oxides, or combinations thereof; metal sulfides such as zinc sulfide; or organics such as amine derivatives.

[0086] When light is incident on the photoelectric element (100, 100') from the first electrode 10 or second electrode 20 side and the photoactive layer 30 absorbs the light in a predetermined wavelength range, excitons are generated inside the photoelectric element (100, 100'). The excitons are separated into holes and electrons in the photoactive layer 30, and the separated holes move to the anode side of one of the first electrode 10 and the second electrode 20, and the separated electrons move to the cathode side of the other of the first electrode 10 and the second electrode 20, causing a current to flow. The photoelectric element (100, 100') may be applied to sensors such as image sensors (CMOS image sensors), photodetectors, optical sensors (infrared optical sensors), solar cells, etc., but is not limited thereto. The photoelectric element is applied, for example, to a sensor. The sensor is an organic CMOS sensor, for example an organic CMOS infrared light sensor or an organic CMOS image sensor.

[0087] Hereinafter, an image sensor including a photoelectric element according to the present invention will be described with reference to the drawings. FIG. 3 is a cross-sectional view showing a schematic configuration of an image sensor according to one embodiment of the present invention. Referring to FIG. 3, an image sensor 200 according to an embodiment of the present invention includes a semiconductor substrate 110 , an insulating layer 80 and a photoelectric element 100 . Although FIG. 3 illustrates an image sensor 200 including the photoelectric element 100 of FIG. 1, the image sensor 200 may also include the photoelectric element 100' of FIG.

[0088] The semiconductor substrate 110 is a silicon substrate on which a transfer transistor (not shown) and a charge reservoir 55 are integrated. A charge reservoir 55 is integrated for each pixel. The charge reservoir 55 is electrically connected to the photoelectric element 100, and the information in the charge reservoir 55 is conveyed by a transfer transistor. Metal wiring (not shown) and pads (not shown) are also formed on the semiconductor substrate 110 . The metal lines and pads are made of metals having low resistivity to reduce signal delay, such as, but not limited to, aluminum (Al), copper (Cu), silver (Ag), and alloys thereof. However, the present invention is not limited to the above structure, and the metal wiring and pads may be disposed under the semiconductor substrate 110 .

[0089] An insulating layer 80 is formed over the metal lines and pads. The insulating layer 80 is made of inorganic insulating materials such as silicon oxide and / or silicon nitride, or low dielectric constant (low K) materials such as SiC, SiCOH, SiCO, and SiOF. The insulating layer 80 has a trench 85 that exposes the charge reservoir 55 . The trench 85 is filled with a filling material.

[0090] On top of the insulating layer 80, the photoelectric element 100 described above is formed. The photovoltaic device 100 includes a first electrode 10, a photoactive layer 30, and a second electrode 20 as described above. The figure presents a structure in which a first electrode 10, a photoactive layer 30, and a second electrode 20 are stacked in sequence, but this is not limited thereto, and the second electrode 20, the photoactive layer 30, and the first electrode 10 may be arranged in this order. The first electrode 10 and the second electrode 20 are both transparent electrodes, and the photoactive layer 30 is as described above. Photoactive layer 30 selectively absorbs light in the infrared wavelength range. Of the light incident from the second electrode 20 side, the light in the infrared wavelength region is mainly absorbed by the photoactive layer 30 and is photoelectrically converted.

[0091] A condenser lens (not shown) is further formed on the photoelectric element 100 . A focusing lens controls the direction of incoming light to focus it at a single point. The focusing lens may be, for example, cylindrical or hemispherical, but is not limited thereto.

[0092] FIG. 4 is a cross-sectional view showing a schematic configuration of an image sensor according to another embodiment of the present invention. Referring to FIG. 4, an image sensor 300 according to another embodiment of the present invention includes a semiconductor substrate 110 in which photo-sensing elements (50a, 50b, 50c), transfer transistors (not shown) and charge storages 55 are integrated, a lower insulating layer 60, color filter layers (70a, 70b, 70c), an upper insulating layer 80, and a photoelectric element 100.

[0093] The semiconductor substrate 110 has integrated thereon the light sensing elements (50a, 50b, 50c), a transfer transistor (not shown), and a charge reservoir 55. The light-sensing elements (50a, 50b, 50c) are photodiodes (eg, silicon-based diodes). The photo-sensing element (50a, 50b, 50c), the transfer transistor and / or the charge reservoir 55 are integrated per pixel, and as an example, the photo-sensing element 50a is included in a red pixel, the photo-sensing element 50b is included in a green pixel, and the photo-sensing element 50c is included in a blue pixel. The photo-sensing elements (50a, 50b, 50c) sense light, and the sensed information is transmitted by the transmission transistor. The charge reservoir 55 is electrically connected to the photoelectric element 100, and the information of the charge reservoir 55 is transmitted by the transmission transistor.

[0094] Metal wiring (not shown) and pads (not shown) are also formed on the semiconductor substrate 110 . The metal lines and pads are made of metals having low resistivity to reduce signal delay, such as, but not limited to, aluminum (Al), copper (Cu), silver (Ag), and alloys thereof. However, the present invention is not limited to the above structure, and the metal wiring and pads may be disposed under the photo-sensing elements 50a and 50b. A lower insulating layer 60 is formed on the metal lines and pads. The lower insulating layer may be formed of the materials described for the insulating layer 80.

[0095] On the lower insulating film 60, color filters (70a, 70b, 70c) are formed. The color filters (70a, 70b, 70c) include a red filter 70a formed in a red pixel, a green filter 70b formed in a green pixel, and a blue filter 70c formed in a blue pixel. An upper insulating layer 80 is formed over the color filters (70a, 70b, 70c). The upper insulating layer 80 is flattened by removing steps caused by the color filters (70a, 70b, 70c).

[0096] On top of the upper insulating layer 80, the above-mentioned photoelectric element 100 is formed. The photovoltaic device 100 includes a first electrode 10, a photoactive layer 30, and a second electrode 20 as described above. The figure shows an example of a structure in which a first electrode 10, a photoactive layer 30, and a second electrode 20 are stacked in sequence, but this is not limited to this, and the second electrode 20, the photoactive layer 30, and the first electrode 10 may be arranged in this order. The first electrode 10 and the second electrode 20 are both transparent electrodes, and the photoactive layer 30 is as described above. Photoactive layer 30 selectively absorbs light in the infrared wavelength range.

[0097] Of the light incident from the second electrode 20 side, the light in the infrared wavelength region is mainly absorbed by the photoactive layer 30 and is photoelectrically converted. Light in the remaining wavelength range passes through the first electrode 10 and the color filters (70a, 70b, 70c), and the light in the red wavelength range that passes through the color filter 70a is sensed by the photo-sensing element 50a, the light in the green wavelength range that passes through the color filter 70b is sensed by the photo-sensing element 50b, and the light in the blue wavelength range that passes through the color filter 70c is sensed by the photo-sensing element 50c.

[0098] FIG. 5 is a cross-sectional view showing a schematic configuration of an image sensor according to still another embodiment of the present invention. Referring to FIG. 5, the image sensor 400 according to this embodiment includes a semiconductor substrate 110 in which an infrared light charge storage 55IR, a blue light charge storage 55B, a green light charge storage 55G, a red light charge storage 55R, and a transfer transistor (not shown) are integrated, a lower insulating layer 65, a blue light sensing element 100B, a green light sensing element 100G, a red light sensing element 100R, and an infrared light sensing element 100IR.

[0099] The semiconductor substrate 110 is a silicon substrate on which an infrared light charge reservoir 55IR, a blue light charge reservoir 55B, a green light charge reservoir 55G, a red light charge reservoir 55R, and a transfer transistor (not shown) are integrated. A blue photocharge reservoir 55B, a green photocharge reservoir 55G, and a red photocharge reservoir 55R are integrated for each blue, green, and red pixel. The infrared light charge storage 55IR, the blue light charge storage 55B, the green light charge storage 55G, and the red light charge storage 55R are portions where charges absorbed in the infrared light sensing element 100IR, the blue light sensing element 100B, the green light sensing element 100G, and the red light sensing element 100R move and are accumulated, and are electrically connected to the infrared light sensing element 100IR, the blue light sensing element 100B, the green light sensing element 100G, and the red light sensing element 100R, respectively.

[0100] Metal wiring (not shown) and pads (not shown) are also formed on the semiconductor substrate 110 . The metal lines and pads are made of metals having low resistivity to reduce signal delay, such as, but not limited to, aluminum (Al), copper (Cu), silver (Ag), and alloys thereof. A lower insulating layer 65 is formed over the metal lines and pads. The lower insulating layer 65 is made of inorganic insulating materials such as silicon oxide and / or silicon nitride, or low dielectric constant (low K) materials such as SiC, SiCOH, SiCO, and SiOF.

[0101] On the lower insulating layer 65, a blue light-sensing element 100B, a green light-sensing element 100G, a red light-sensing element 100R, and an infrared light-sensing element 100IR are formed. The blue light-sensing element 100B includes a first electrode 10B, a second electrode 20B, and a photoactive layer 30B that selectively absorbs light in the blue wavelength region, the green light-sensing element 100G includes a first electrode 10G, a second electrode 20G, and a photoactive layer 30G that selectively absorbs light in the green wavelength region, the red light-sensing element 100R includes a first electrode 10R, a second electrode 20R, and a photoactive layer 30R that selectively absorbs light in the red wavelength region, and the infrared light-sensing element 100IR includes a first electrode 10IR, a second electrode 20IR, and a photoactive layer 30IR that selectively absorbs light in the infrared wavelength region.

[0102] The first electrodes (10B, 10G, 10R, 10IR) and the second electrodes (20B, 20G, 20R, 20IR) are light-transmitting electrodes and are made of a transparent conductor such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO), aluminum tin oxide (AlTO), and fluorine-doped tin oxide (FTO), or are thin metal films having a thickness of several nanometers to several tens of nanometers or thin metal films doped with metal oxide and having a thickness of several nanometers to several tens of nanometers.

[0103] The photoactive layers (30B, 30G, 30R, 30IR) include a p-type semiconductor compound and an n-type semiconductor compound. The photoactive layer 30B of the blue light-sensing element 100B contains a p-type semiconductor compound that selectively absorbs light in the blue wavelength region and an n-type semiconductor compound that selectively absorbs light in the blue wavelength region, the photoactive layer 30G of the green light-sensing element 100G contains a p-type semiconductor compound that selectively absorbs light in the green wavelength region and an n-type semiconductor compound that selectively absorbs light in the green wavelength region, the photoactive layer 30R of the red light-sensing element 100R contains a p-type semiconductor compound that selectively absorbs light in the red wavelength region and an n-type semiconductor compound that selectively absorbs light in the red wavelength region, and the photoactive layer 30IR of the infrared light-sensing element 100IR contains the compound of the present invention described above. The infrared light sensing element 100IR selectively absorbs light in the infrared region of not less than about 750 nm and not more than about 3000 nm without absorbing light in the visible light region.

[0104] FIG. 6 is a cross-sectional view showing a schematic configuration of an image sensor according to still another embodiment of the present invention. Referring to FIG. 6, the image sensor 500 includes a semiconductor substrate 110 in which an infrared light charge storage 55IR, a blue light charge storage 55B, a green light charge storage 55G, a red light charge storage 55R, and a transfer transistor (not shown) are integrated, a lower insulating layer 65, an upper insulating layer 90, a blue light sensing element 100B, a green light sensing element 100G, a red light sensing element 100R, and an infrared light sensing element 100IR. The infrared light-sensing element 100IR is formed in front of the blue light-sensing element 100B, the green light-sensing element 100G, and the red light-sensing element 100R. The remaining configuration is similar to that of the image sensor shown in FIG.

[0105] In the configuration of FIG. 6, the infrared light-sensing element 100IR exists on the lower insulating layer 65, and the blue light-sensing element 100B, the green light-sensing element 100G, and the red light-sensing element 100R may also be disposed thereon. An image sensor 600 having such a configuration is shown in FIG. The infrared light sensing element 100IR selectively absorbs light in the infrared region of about 750 nm to about 3000 nm, and has a wide absorption area to improve efficiency.

[0106] A sensor according to an embodiment of the present invention includes multiple sensors with different functions. As an example, at least one of the multiple sensors with different functions is a biometric sensor, and the biometric sensor may be, for example, but is not limited to, an iris sensor, a distance sensor, a fingerprint sensor, a vascularity sensor, etc. As an example, one of a plurality of image sensors having different functions is an iris sensor and another is a depth sensor.

[0107] An iris sensor is a sensor that uses the unique characteristics of the iris of each person to identify an individual. It performs iris authentication by capturing an image of the user's eye using the sensor within an appropriate distance from the user, processing the captured image, and comparing it with a pre-stored image. A depth sensor is a sensor that grasps the shape and position of an object from 3D object information. It photographs an object using the sensor within an appropriate distance from the user and processes the photographed image to confirm the shape and position of the object. Such distance sensors are used, for example, in face recognition sensors.

[0108] In one embodiment of the invention, the sensors are configured to detect a first wavelength λ 2 , for example in the infrared wavelength range. 1 a first infrared light sensor for detecting light in the infrared region having a second wavelength λ 2 and a second infrared light sensor for sensing infrared light having a first infrared light sensor. First wavelength λ 1 and the second wavelength λ 2 are different from each other within a wavelength region of, for example, about 800 nm to 3000 nm, for example, the first wavelength λ 1 and the second wavelength λ 2 The difference is about 30 nm or more, and within the above range, about 50 nm or more, about 70 nm or more, about 80 nm or more, and about 90 nm or more.

[0109] As an example, the first wavelength λ 1 and the second wavelength λ 2 One of them belongs to the wavelength region of about 780 nm to 900 nm, and the first wavelength λ 1 and the second wavelength λ 2 The other one belongs to the wavelength region of more than about 900 nm and less than or equal to 1000 nm. As an example, the first wavelength λ 1 and the second wavelength λ 2 One of them belongs to the wavelength region of about 780 nm to 840 nm, and the first wavelength λ 1 and the second wavelength λ 2 The other one belongs to the wavelength region of about 910 nm to 970 nm. As an example, the first wavelength λ 1 and the second wavelength λ 2 One of them belongs to a wavelength region of about 800 nm to 830 nm, and the first wavelength λ 1 and the second wavelength λ 2 The other one belongs to the wavelength region of about 930 nm to 950 nm. As an example, the first wavelength λ 1 and the second wavelength λ 2 One of them belongs to the wavelength region of about 805 nm to 815 nm, and the first wavelength λ 1 and the second wavelength λ 2 The other one belongs to the wavelength region of about 935 nm to 945 nm. As an example, the first wavelength λ 1 and the second wavelength λ 2 One of the wavelengths is about 810 nm, and the first wavelength λ 1 and the second wavelength λ 2 The other one is at about 940 nm.

[0110] FIG. 8 is a cross-sectional view showing a schematic configuration of an image sensor including a plurality of sensors according to an embodiment of the present invention. The image sensor 700 according to this embodiment includes a semiconductor substrate 110 in which a dual bandpass filter 95, a first infrared light sensor 100A, an insulating layer 80, and a second infrared light sensor 120 are integrated (at least partially buried). The first infrared light sensor 100A and the second infrared light sensor 120 are stacked in a direction perpendicular to the upper surface 110S of the semiconductor substrate 110, for example.

[0111] The dual bandpass filter 95 is disposed on the front side of the first infrared light sensor 100A and is configured to filter a first wavelength λ 1 Infrared light including a second wavelength λ 2 The material selectively transmits infrared light, including infrared rays, and blocks and / or absorbs other light. Here, other light includes light in the ultraviolet and visible light regions. 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 is similar to the photoelectric element (100, 100') of the above-described embodiments. The second infrared light sensor 120 is integrated in the semiconductor substrate 110 and is a light sensing element. The semiconductor substrate 110 is, for example, a silicon substrate, on which the second infrared light sensor 120, the charge reservoir 55 and a transfer transistor (not shown) are integrated.

[0112] The second infrared light sensor 120 is a photodiode that senses incident light, and the sensed information is transmitted by a transmission transistor. Here, the light incident on the second infrared light sensor 120 is light that has passed through the dual bandpass filter 95 and the first infrared light sensor 100A and has a second wavelength λ 2 The infrared light is in a predetermined range including the infrared light. First wavelength λ 1 The infrared light in the predetermined region including the above is entirely absorbed by the photoactive layer 30 of the first infrared light sensor and does not reach the second infrared light sensor 120. In this case, a separate filter for wavelength selectivity of the light incident on the second infrared light sensor 120 is not required. However, the first wavelength λ 1In case that infrared light in a predetermined region including the above is not completely 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.

[0113] The sensor according to this embodiment not only functions as a composite sensor by including two infrared light sensors that perform separate functions, but also doubles the number of pixels that perform the function of each sensor by stacking two sensors that perform separate functions in each pixel while maintaining the same size, thereby significantly improving sensitivity. FIG. 9 is a cross-sectional view showing a schematic configuration of an image sensor according to still another embodiment of the present invention. Referring to FIG. 9, as in the previous embodiments, an image sensor 800 includes a visible light sensor 50 and a photosensitive element 100 . The visible light sensor 50 includes a red light sensing element 50a, a green light sensing element 50b, and a blue light sensing element 50c integrated on a semiconductor substrate 110, where the red light sensing element 50a, the green light sensing element 50b, and the blue light sensing element 50c may be photodiodes (e.g., silicon-based photodiodes) and are configured to selectively absorb light in the visible light range. The red light-sensing element 50a, the green light-sensing element 50b, and the blue light-sensing element 50c are stacked in a direction perpendicular to the substrate. The red light-sensing element 50a, the green light-sensing element 50b, and the blue light-sensing element 50c are configured to selectively absorb and / or convert (photoelectrically convert into an electrical signal) and sense light in each wavelength region depending on the depth of the stack. FIG. 10 is a cross-sectional view showing a schematic configuration of an image sensor according to still another embodiment of the present invention. Referring to FIG. 10, the image sensor 900 includes a first photoelectric element (e.g., infrared photoelectric element 1200d) configured to selectively absorb and / or convert (e.g., photoelectric conversion to an electrical signal) light in an infrared wavelength spectrum (e.g., a first infrared wavelength region) of incident light, and at least one additional photoelectric element (e.g., 1200a-1200c) vertically stacked between the first photoelectric element and a semiconductor substrate (e.g., 110), the additional photoelectric elements including respective photoelectric conversion layers and configured to selectively absorb and / or convert (e.g., photoelectric conversion) a separate (e.g., each) wavelength region of the incident light that is different from the first infrared wavelength region. The individual (eg, each) wavelength region may be a visible or non-visible wavelength region. For example, as shown in FIG. 10, image sensor 900 includes additional photoelectric elements including a red photoelectric element 1200a configured to selectively absorb and / or convert (photoelectrically convert to an electrical signal) light in the red wavelength spectrum of the incident light, a green photoelectric element 1200b configured to selectively absorb and / or convert (photoelectrically convert to an electrical signal) light in the green wavelength spectrum of the incident light, and a blue photoelectric element 1200c configured to selectively absorb and / or convert (photoelectrically convert to an electrical signal) light in the blue wavelength spectrum of the incident light. The red photoelectric element 1200a, the green photoelectric element 1200b, and the blue photoelectric element 1200c are stacked in a direction perpendicular to the top surface 110S of the semiconductor substrate 110 (eg, the y direction). Although image sensor 900 is illustrated as including multiple additional photoelectric elements (1200a-1200c) in addition to a first photoelectric element (e.g., fourth photoelectric element 1200d) configured to selectively absorb and / or convert light in the first near-infrared wavelength region, organic sensor 970 may include one additional photoelectric element (e.g., any one of 1200a-1200c) between photoelectric element 1200d and semiconductor substrate 110. The image sensor 900 according to this embodiment includes a semiconductor substrate 110, a lower insulating layer 80a, a first intermediate insulating layer 80b, a second intermediate insulating layer 80c, an upper insulating layer 80d, a first photoelectric element 1200a, a second photoelectric element 1200b, a third photoelectric element 1200c, and a fourth photoelectric element 1200d. In this embodiment, the fourth photoelectric element 1200d is a first photoelectric element configured to selectively absorb and / or convert (photoelectrically convert to an electrical signal) light in a first near-infrared wavelength region, and the first to third photoelectric elements (1200a to 1200c) collectively are at least one additional photoelectric element configured to selectively absorb and / or convert (photoelectrically convert to an electrical signal) light in one or more separate wavelength regions different from the first near-infrared wavelength region. As shown in the figure, the first to fourth photoelectric elements (1200a to 1200d) are vertically stacked on the semiconductor substrate 110, and the first to fourth photoelectric elements (1200a to 1200d) overlap each other in a direction extending perpendicular to the upper surface 110S of the semiconductor substrate 110. The semiconductor substrate 110 may be a silicon substrate, in which a transfer transistor (not shown) and a charge reservoir are integrated. A first photoelectric element 1200a is formed on the lower insulating layer 80a. The first photoelectric element 1200a includes a photoelectric conversion layer 1230a. The first photoelectric device 1200a is a photoelectric device according to any one of the above-mentioned embodiments. Photoelectric conversion layer 1230a selectively absorbs and / or converts (photoelectrically converts to an electrical signal) incident light in one of the infrared, red, blue, and green wavelength spectrums. For example, the first photoelectric element 1200a is a blue photoelectric element. A first intermediate insulating layer 80b is formed on the first photoelectric element 1200a. The second photoelectric element 1200b is formed on the first intermediate insulating layer 80b. The second photoelectric element 1200b includes a photoelectric conversion layer 1230b. The second photoelectric device 1200b is a photoelectric device according to any one of the above-mentioned embodiments. Photoelectric conversion layer 1230b selectively absorbs and / or converts (photoelectrically converts to an electrical signal) incident light in one of the infrared, red, blue, and green wavelength spectrums. For example, the second photoelectric element 1200b is a green photoelectric element. A second intermediate insulating layer 80c is formed on the second photoelectric element 1200b. The third photoelectric element 1200c is formed on the second intermediate insulating layer 80c. The third photoelectric element 1200c includes a photoelectric conversion layer 1230c. The third photoelectric device 1200c is a photoelectric device according to any one of the above-mentioned embodiments. Photoelectric conversion layer 1230c selectively absorbs and / or converts (photoelectrically converts to an electrical signal) incident light in one of the infrared, red, blue, and green wavelength spectrums. For example, the third photoelectric element 1200c is a red photoelectric element. An upper insulating layer 80d is formed on the third photoelectric element 1200c. The lower insulating layer 80a, the first and second intermediate insulating layers (80b, 80c) and the upper insulating layer 80d have a plurality of through holes or trenches (85a, 85b, 85c, 85d) exposing the charge reservoirs (55a, 55b, 55c, 55d). A fourth photoelectric element 1200d is formed on the upper insulating layer 80d. The fourth photoelectric element 1200d includes a photoelectric conversion layer 1230d. The fourth photoelectric device 1200d is a photoelectric device according to any one of the above-mentioned embodiments. Photoelectric conversion layer 1230d selectively absorbs and / or converts (photoelectrically converts to an electrical signal) incident light in one of the infrared, red, blue, and green wavelength spectrums. For example, the fourth photoelectric element 1200d is an infrared / near infrared photoelectric element that includes an infrared absorbing material. In FIG. 10, the first photoelectric element 1200a, the second photoelectric element 1200b, the third photoelectric element 1200c, and the fourth photoelectric element 1200d are stacked in sequence, however, the present invention is not limited thereto and the elements may be stacked in various orders. As described above, the first photoelectric element 1200a, the second photoelectric element 1200b, the third photoelectric element 1200c, and the fourth photoelectric element 1200d have a stacked structure, which can reduce the size of the organic sensor and achieve miniaturization. The image sensor described above may be applied to various electronic devices, such as, but not limited to, cameras, camcorders, mobile phones incorporating these, display devices, security devices, and medical devices.

[0114] FIG. 11 is a block diagram showing a schematic configuration of a digital camera including an image sensor according to an embodiment of the present invention. Referring to FIG. 11, a digital camera 1000 includes a lens 1010, an image sensor 1020, a motor 1030, and an engine 1040. The image sensor 1020 is any one of the image sensors according to the embodiments shown in FIGS.

[0115] The lens 1010 focuses the incident light onto the image sensor 1020 . The image sensor 1020 generates RGB data for the light received through the lens 1010 . In one embodiment of the present invention, the image sensor 1020 interfaces with the engine 1040 . Motor 1030 adjusts the focus of lens 1010 or adjusts the shutter in response to a control signal received from engine 1040 . The engine 1040 regulates the image sensor 1020 and the motor 1030 . The engine 1040 is connected to a host / application 1050 .

[0116] FIG. 12 is a block diagram showing a schematic configuration of an electronic device according to an embodiment of the present invention. Referring to FIG. 12, an electronic device 1100 includes a processor 1120, a memory 1130, and an image sensor 1140 electrically connected to each other via a bus 1110. Image sensor 1140 includes any image sensor according to the embodiments described above. The memory 1130 is a non-transitory computer-readable medium capable of storing a program of instructions.

[0117] The memory 1130 may be a non-volatile memory such as flash memory, phase-change random access memory (PRAM), magneto-resistive RAM (MRAM), resistive RAM (ReRAM), or ferro-electric RAM (FRAM®), or a volatile memory such as static RAM (SRAM), dynamic RAM (DRAM), or synchronous DRAM (SDRAM). The processor 1120 executes stored command programs to perform one or more functions. For example, the processor 1120 is configured to process the electrical signals generated by the image sensor 1140 . The processor 1120 is configured to generate an output (eg, an image to be displayed on a display interface) based on the above processing.

[0118] One or more of the components disclosed above may include or be implemented by processing circuitry, such as hardware including logic circuitry (either a hardware / software combination, such as a processor executing software, or a combination thereof). For example, the processing circuit 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-chip (SoC), a programmable logic device, a microprocessor, an application-specific integrated circuit (ASIC), and the like.

[0119] The above-mentioned embodiments of the present invention will now be described in more detail with reference to the following examples. However, the following examples are merely illustrative and are not intended to limit the scope of the present invention.

[0120] <<Synthesis example>> Synthesis Example 1: Synthesis of compound represented by chemical formula 1-1 (compound (6)) [ka] [ka] [ka] [ka]

[0121] i) Step 1: Synthesis of compound (1) 1-octylbenzo[cd]indol-2(1H)-one (2.0 g, 7.1 mmol) was dissolved in 10 mL of dry tetrahydrofuran (THF), to which ethylmagnesium bromide solution (3 M in diethyl ether, 7.1 mL, 21.3 mmol) was slowly added, and the mixture was stirred at 60°C for 6 hours. Then, 1N HCl (20 mL) was slowly added at 0°C, and the THF was evaporated to remove the remaining solution, which was then dissolved in KI (2.36 g, 14.2 mmol, in 20 mL H 2 O) solution. The precipitate was then filtered to obtain compound (1) (1.8 g, yield: about 60%). LC-MS: Confirmation of molecular weight of 294.21m / z

[0122] ii) Step 2: Synthesis of compound (2) "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 stirred at 95°C for 3 hours. Then, thionyl chloride was evaporated, and compound (1) (0.32 g, 0.8 mmol) was added at room temperature and stirred for 1 hour. Next, triethylamine (0.76 g, 7.5 mmol), H 2 O (0.55 g, 7.5 mmol) and acetone (6 mL) were added and stirred continuously at room temperature. After 12 hours, H 2 The material was dissolved in O (30 mL), and the insoluble portion was removed by filtration. Finally, the pH was adjusted to 2 with 2N HCl (10 mL) and then extracted with methylene chloride (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%). LC-MS: Confirmation of molecular weight of 390.28m / z

[0123] iii) Third step: synthesis of compound (3) 6-Bromobenzo[cd]indol-2(1H)-one (3 g, 12.1 mmol) was dissolved in DMF (60 mL), and NaH (60% in mineral oil, 0.73 g, 18.0 mmol) was gradually added at 0° C. and stirred. After 1 hour, 1-bromooctane (4.7 g, 24.2 mmol) was added at room temperature and the mixture was stirred for 12 hours. After the reaction was completed, the mixture was extracted with EA and then purified by silica gel column chromatography (EA:n-Hex=1:10 v / v) to obtain compound (3) (3.8 g, yield: about 88%). LC-MS: Confirmation of molecular weight of 360.10m / z

[0124] iv) Fourth step: synthesis of compound (4) "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 stirred at 110 °C for 18 hours. After the reaction was completed, toluene was concentrated, and the residue 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%). LC-MS: Confirmation of molecular weight of 559.24m / z

[0125] v) Fifth step: synthesis of compound (5) A solution of compound (4) (1.0 g, 1.8 mmol) in dry tetrahydrofuran (6 mL) was slowly added with a methylmagnesium chloride solution (3 M in THF, 0.78 mL, 2.3 mmol) and the mixture was stirred at 60° C. for 6 hours. Then, at 0°C, 2 O (5 mL) and 1.5 mL of perchloric acid were added slowly in sequence. Finally, the product was extracted with EA, then precipitated in hexane and filtered to obtain compound (5) (0.9 g, yield: about 76%). LC-MS: Confirmation of molecular weight of 557.25m / z

[0126] vi) Step 6: Synthesis of the compound represented by formula 1-1 (compound (6)) 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 the mixture was stirred at 80° C. for 1 hour. After the reaction was completed, the solvent was removed, and the residue was purified by silica gel column chromatography (EA:n-Hex=1:2 v / v) to obtain compound (6) (0.03 g, yield: about 31%). LC-MS: Confirmation of molecular weight of 928.54m / z

[0127] Synthesis Example 2: Synthesis of compound represented by chemical formula 1-2 (compound (10)) [ka] [ka]

[0128] i) Step 1: Synthesis of compound (7) Benzo[cd]indol-2(1H)-one (1 g, 5.9 mmol) was dissolved in DMF (24 mL), and NaH (60% in mineral oil, 0.36 g, 8.9 mmol) was slowly added at 0° C. and stirred. After 1 hour, benzyl bromide (2.0 g, 11.8 mmol) was added at room temperature and the mixture was stirred for 12 hours. After the reaction was completed, the mixture was extracted with EA and then purified by silica gel column chromatography (EA:n-Hex=1:10 v / v) to obtain compound (7) (1.5 g, yield: about 98%). LC-MS: Confirmation of molecular weight of 260.13m / z

[0129] ii) Step 2: Synthesis of compound (8) Compound (7) (1.5 g, 5.8 mmol) was dissolved in "dry THF" (10 mL) and an ethylmagnesium bromide solution (3 M in diethyl ether, 5.8 mL, 17.4 mmol) was gradually added thereto, followed by stirring at 60°C for 6 hours. Then, 1N HCl (20 mL) was slowly added at 0°C, and the THF was evaporated. The remaining solution was dissolved in KI (1.92 g, 11.6 mmol, in 20 mL H2 O) solution. The precipitate was then filtered to obtain compound (8) (0.9 g, yield: about 40%). LC-MS: Confirmation of molecular weight of 272.11m / z

[0130] iii) Third step: synthesis of compound (9) 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 toluene (8 mL) and stirred at 95° C. for 3 hours. Then, after evaporating thionyl chloride, compound (8) (0.3 g, 0.8 mmol) was added at room temperature and stirred for 1 hour. Next, "triethylamine" (0.76g, 7.5mmol), H 2 O (0.55 g, 7.5 mmol) and acetone (6 mL) were added and stirred at room temperature. After 12 hours, H 2 The material was dissolved in O (30 mL), and the insoluble portion was removed by filtration. Finally, the pH was adjusted to 2 with 2N HCl (10 mL) and then extracted with MC. The obtained 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: about 72%). LC-MS: Confirmation of molecular weight of 368.15m / z

[0131] iv) Fourth step: Synthesis of the compound represented by formula 1-2 (compound (10)) 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 the mixture was stirred at 80° C. for 1 hour. After the reaction was completed, the solvent was removed, and the residue was purified by silica gel column chromatography (EA:n-Hex=1:2 v / v) to obtain compound (10) (0.02 g, yield: about 21%). LC-MS: Confirmation of molecular weight of 906.58m / z

[0132] Synthesis Example 3: Synthesis of compound represented by chemical formula 1-3 (compound 19) [ka] [ka] [ka] [ka]

[0133] i) Step 1: Synthesis of compound (11) 6-bromobenzo[cd]indol-2(1H)-one (6.1 g, 24.7 mmol) and Lawesson reagent (5.0 g, 12.4 mmol) were dissolved in 250 mL of toluene and stirred at 110° C. for 12 hours. Then, the temperature was lowered to room temperature, the toluene was evaporated, and the product was 2 Compound (11) was obtained by precipitation in O (5.3 g, yield: about 82%). LC-MS: Confirmation of molecular weight of 263.85m / z

[0134] ii) Step 2: Synthesis of compound (12) Compound (11) (2 g, 7.6 mmol) and iodomethane (1.3 g, 9.1 mmol) were dissolved in 1N NaOH (10 mL) and THF (50 mL) and stirred at room temperature. After 1 h, extraction with EA and evaporation gave compound (12) (3 g, yield: about 98%).

[0135] iii) Third step: synthesis of compound (13) Compound (12) (3 g, 7.4 mmol), "Meldrum's acid" (2 g, 13.9 mmol), and sodium acetate (1.14 g, 13.9 mmol) were dissolved in 60 mL of ethanol and stirred at 80°C for 2 hours. The product was cooled to room temperature and filtered to immediately obtain compound (13) (2.1 g, yield: about 75%).

[0136] iv) Step 4: Synthesis of compound (14) 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 DMF (20 mL) and stirred at 120° C. for 8 hours. The product 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%). LC-MS: Confirmation of molecular weight of 488.19m / z

[0137] v) 5th step: synthesis of compound (15) 4-methyl-N,N-bis(4-(octyloxy)phenyl)-2-(trimethylstannyl)-4H-selenopheno[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 stirred at 110 °C for 18 hours. After the reaction was completed, toluene was concentrated, and the residue 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%). LC-MS: Confirmation of molecular weight of 841.41m / z

[0138] vi) Step 6: Synthesis of compound (16) Compound (15) (0.9 g, 1.1 mmol) was dissolved in anhydrous THF and stirred at -78°C. 2.5M "n-BuLi" (in n-Hex, 0.5mL, 1.3mmol) was gradually added and the mixture was stirred for 3 hours. Then, 1M "trimethyltin chloride" (in THF, 1.3mL, 1.3mmol) was added and the mixture was allowed to warm to room temperature. The obtained product (compound (16), 1.0 g, yield: about 93%) was extracted with chloroform and then used in the next reaction without further purification. LC-MS: Confirmation of molecular weight of 1005.31m / z

[0139] vii) Step 7: Synthesis of compound (17) 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 stirred at 110°C for 18 hours. After the reaction was completed, toluene was concentrated, and the residue 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%). LC-MS: Confirmation of molecular weight of 1248.58m / z

[0140] viii) Step 8: Synthesis of compound (18) Compound (17) (0.1 g, 0.08 mmol) was dissolved in acetic acid (5 mL), and HCl (0.2 mL) was slowly added. After stirring at 70°C for 1 hour, NaPF 6 (0.13g, 0.8mmol) in H 2 When O (1 mL) was added, the product precipitated, which was filtered to give compound (18) (0.09 g, yield: about 89%). LC-MS: Confirmation of molecular weight of 1118.54m / z

[0141] ix) 9th step: Synthesis of the compound represented by formula 1-3 (compound (19)) 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 the mixture was stirred at 80° C. for 1 hour. After the reaction was completed, the solvent was removed, and the residue was purified by silica gel column chromatography (EA:n-Hex=1:2 v / v) to obtain compound (19) (0.015 g, yield: about 20%). LC-MS: Confirmation of molecular weight of 1490.97m / z

[0142] Synthesis Example 4: Synthesis of compound represented by chemical formula 1-4 (compound (22)) [ka] [ka] [ka]

[0143] i) Step 1: Synthesis of compound (20) 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%) were dissolved in toluene (20 mL) and stirred at 110°C for 18 hours. After the reaction was completed, toluene was concentrated, and the residue 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%). LC-MS: Confirmation of molecular weight of 937.61m / z

[0144] ii) Step 2: Synthesis of compound (21) Compound (20) (0.35 g, 0.37 mmol) was dissolved in acetic acid (20 mL), and 1 mL of HCl (35%) was slowly added. After stirring at 70 °C for 1 h, KI (0.13 g, 0.8 mmol, in H 2 When O (10 mL) was added, the product precipitated, which was filtered to obtain compound (21) (0.30 g, yield: about 86%). LC-MS: Confirmation of molecular weight at 807.50m / z

[0145] iii) Third step: Synthesis of a compound represented by chemical formula 1-4 (compound (22)) Compound (2) (0.030 g, 0.08 mmol) and compound (21) (0.072 g, 0.08 mmol) were dissolved in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and the mixture was stirred at 80° C. for 1 hour. After the reaction was completed, the solvent was removed, and the residue was purified by silica gel column chromatography (EA:n-Hex=1:2 v / v) to obtain compound (22) (0.03 g, yield: about 33%). LC-MS: Confirmation of molecular weight of 1178.48m / z

[0146] Synthesis Example 5: Synthesis of compound represented by chemical formula 1-5 (compound (23)) [ka] [ka]

[0147] i) Step 1: Synthesis of the compound represented by formula 1-5 (compound (23)) 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 the mixture was stirred at 110° C. for 1 hour. After the reaction was completed, the solvent was removed, and the residue was purified by silica gel column chromatography (EA:n-Hex=1:2 v / v) to obtain compound (23) (0.02 g, yield: about 28%). LC-MS: Confirmation of molecular weight of 1692.90m / z

[0148] Synthesis Example 6: Synthesis of compound represented by chemical formula 1-6 (compound (25)) [ka] [ka]

[0149] i) Step 1: Synthesis of compound (24) 2-Methyl-1-octylbenzo[cd]indol-1-ium iodide (0.4 g, 1.0 mmol) and croconic acid (0.2 g, 1.4 mmol) were dissolved in acetone (6 mL) and H 2 The mixture was dissolved in a mixed solvent of 2H2O (6 mL) and stirred at room temperature for 72 h. After that, H 2 O (40 mL) was added and all soluble impurities were removed using a filter. The remaining precipitate 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%). LC-MS: Confirmation of molecular weight at 404.20m / z

[0150] ii) Second step: Synthesis of the compound represented by formula 1-6 (compound (25)) Compound (5) (0.067 g, 0.1 mmol) and compound (24) (0.041 g, 0.1 mmol) were dissolved in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and the mixture was stirred at 110° C. for 1 hour. After the reaction was completed, the solvent was removed, and the residue was purified by silica gel column chromatography (EA:n-Hex=1:2 v / v) to obtain compound (25) (0.02 g, yield: about 21%). LC-MS: Confirmation of molecular weight of 942.68m / z

[0151] Synthesis Example 7: Synthesis of compound represented by chemical formula 1-7 (compound (26)) [ka] [ka]

[0152] i) Step 1: Synthesis of the compound represented by formula 1-7 (compound (26)) Compound (21) (0.070 g, 0.07 mmol) and compound (24) (0.030 g, 0.07 mmol) were dissolved in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL) and stirred at 110° C. for 1 hour. After the reaction was completed, the solvent was removed, and the residue was purified by silica gel column chromatography (EA:n-Hex=1:2 v / v) to obtain compound (26) (0.015 g, yield: about 17%). LC-MS: Confirmation of molecular weight of 1192.44m / z

[0153] Synthesis Example 8: Synthesis of compound represented by chemical formula 1-8 (compound (27)) [ka] [ka]

[0154] i) Step 1: Synthesis of compound represented by chemical formula 1-8 (compound (27)) Compound (21) (0.080 g, 0.09 mmol) and croconic acid (0.006 g, 0.04 mmol) were dissolved in a mixed solvent of 1-butanol (3 mL) and toluene (3 mL), and the mixture was stirred at 110° C. for 1 hour. After the reaction was completed, the solvent was removed, and the residue was purified by silica gel column chromatography (EA:n-Hex=1:2 v / v) to obtain compound (27) (0.02 g, yield: about 27%). LC-MS: Confirmation of molecular weight of 1721.76m / z

[0155] Comparative Synthesis Example 1: Synthesis of compound represented by formula 2-1 It was synthesized according to the method described in ACS Appl. Mater. Interfaces, 10, 11063 (2018). [ka] [ka]

[0156] Comparative Synthesis Example 2: Synthesis of compound represented by chemical formula 2-2 [ka] [ka]

[0157] 2-Methyl-1-octylbenzo[cd]indol-1-lium iodide (0.4 g, 1.0 mmol) and croconic acid (0.056 g, 0.4 mmol) were dissolved in acetone (6 mL) and H 2 The mixture was dissolved in O (6 mL) and stirred at room temperature for 72 h. After that, H 2 O (40 mL) was added and all soluble impurities were removed using a filter. The remaining precipitate 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%). LC-MS: Confirmation of molecular weight of 665.26m / z

[0158] <<Evaluation I>> Absorption characteristics The compounds obtained in Synthesis Examples 1 to 8 and Comparative Synthesis Example 1 were dissolved in dichloromethane at 1×10 -5 The compounds were dissolved to a concentration of M to prepare solutions, and the absorption characteristics of the compounds in solution were evaluated. The results are shown in Table 1 below. The absorption characteristics were measured using a Shimadzu UV-3600 Plus UV-Vis-NIR spectrometer at the maximum absorption wavelength λ max was measured.

[0159] Furthermore, the compounds obtained in Synthesis Examples 1 to 8 and Comparative Synthesis Example 1 were each coated on a glass substrate by spin coating, and the light absorption characteristics in a thin film state were evaluated. The absorption characteristics were measured using a Shimadzu UV-3600 Plus UV-Vis-NIR spectrometer at the maximum absorption wavelength λ max was measured. The results are shown in Table 1 below.

[0160] [Table 1]

[0161] Referring to Table 1, it can be seen that the compounds according to Synthesis Examples 1 to 8 exhibit better wavelength water absorbency in the infrared wavelength region than the compound according to Comparative Synthesis Example 1.

[0162] <<Evaluation II>>Energy levels and band gaps The HOMO energy level, LUMO energy level, and band gap of the above thin film were calculated using the "B3LYP / 6-31 G(d) level" theory described in "MJ Frisch, et al., Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT (2009)". The results are shown in Table 2 below.

[0163] [Table 2]

[0164] Referring to Table 2, it can be seen that the compounds of Synthesis Examples 1 to 8 have smaller band gap energies than the compound of Comparative Synthesis Example 1, and therefore can effectively absorb light in the infrared wavelength region.

[0165] <<Examples and Comparative Examples>> Fabrication of photoelectric elements An anode was formed by laminating ITO on a glass substrate by sputtering. Next, PEDOT (poly(3,4-ethylenedioxythiophene)) was spin-coated on the anode to form a hole transport layer having a thickness of 45 nm. The compounds obtained in Synthesis Examples 1 to 8 and Comparative Synthesis Examples 1 and 2 were analyzed by PC 70 A solution of BM in chloroform at a mass ratio of 2.5:7.5 was spin-coated onto the hole transport layer to form a photoactive layer (photoelectric conversion layer). Then, C was deposited on the photoactive layer. 60 was evaporated to form a 30 nm thick auxiliary layer. ITO was then sputtered onto the auxiliary layer to form a cathode. Then, after sealing with a glass plate, annealing was performed sequentially at 120° C. and 140° C. for 30 minutes to prepare photoelectric devices according to Examples 1 to 8 and Comparative Synthesis Examples 1 and 2.

[0166] <<Evaluation III>> Photoelectric conversion efficiency The photoelectric conversion efficiency (EQE) of the photoelectric elements 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 Tech, Korea). First, the apparatus was calibrated using a Si photodiode (Hamamatsu Corporation), and then a photoelectric element was attached to the apparatus, and measurements were performed in the wavelength range of about 400 nm to about 1600 nm. Among them, the photoelectric conversion efficiencies (EQE) of the photoelectric elements of Example 1, Example 6, and Comparative Example 1 are shown in FIG. FIG. 13 is a graph showing the results of measuring the photoelectric conversion efficiency of the photoelectric elements of Example 1, Example 6 and Comparative Example 1.

[0167] 13, it can be seen that the photoelectric devices according to Examples 1 and 6 exhibit superior photoelectric conversion efficiency in the long wavelength region of about 1000 nm compared to the photoelectric device according to Comparative Example 1.

[0168] The present invention is not limited to the above-described embodiment, and various modifications can be made without departing from the technical scope of the present invention. [Explanation of symbols]

[0169] 10, 10B, 10G, 10R, 10IR 1st electrode 20, 20B, 20G, 20R, 20IR 2nd electrode 30, 30B, 30G, 30R, 30IR photoactive layer 40, 45 Charge auxiliary layer 50a, 50b, 50c Light sensing element 55 Charge reservoir 55B Blue Light Charge Storage 55G Green Light Charge Storage 55R Red Light Charge Storage 55IR Infrared photocharge reservoir 65 Lower insulation layer 70, 70a, 70b, 70c Color filters (layers) 80 Upper insulating layer 85 Trench 90 Upper insulation layer 95 Dual Bandpass Filter 100, 100' Photoelectric element 100A 1st infrared light sensor 110 Semiconductor substrate 100B Blue light sensing element 100G green light sensing element 100R Red light sensing element 100IR Infrared light sensing element 120 Second infrared light sensor 300, 400, 500, 600, 700 Image Sensor 1000 Digital Camera 1010 Lens 1020 image sensor 1030 Motor 1040 Engine 1050 Host / Application 1100 Electronic equipment 1110 Bus 1120 Processor 1130 Memory 1140 Image Sensor

Claims

1. A compound represented by the following chemical formula 1. 【Chemistry 1】 (In the above Chemical Formula 1, R １ ~R ４ each independently represents a hydrogen atom, a deuterium atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms; R １１ａ ~R １４ｃ are each independently hydrogen, deuterium, a halogen, a cyano group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a functional group represented by the following chemical formula 1A, １１ａ ~R １４ｃ At least one of R is a functional group represented by the following chemical formula 1A. １１ａ ~R １４ｃ exist independently of each other or two adjacent functional groups are linked to each other to form a condensed ring with benzoindole; n is an integer of 1 or 2. 【Chemistry 1A】 (In the above Chemical Formula 1A, L １ is a substituted or unsubstituted heteroaromatic ring group having 2 to 15 carbon atoms, L ２ is a substituted or unsubstituted heteroaromatic ring group having 2 to 15 carbon atoms, a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, Ar is a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring group having 2 to 30 carbon atoms, a fused ring thereof, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylamine group having 2 to 30 carbon atoms; m is 0, 1, or 2.

2. In the above Chemical Formula 1A, L １ and L ２ are each independently a heteroaromatic ring group selected from the following formulas 1A-11 to 1A-15, or a combination thereof. 【Chemical 1A-11-1A-15】 (In the above Chemical Formula 1A-11 to Chemical Formula 1A-15, X １ , X ２ , and X ３ are each independently O, S, Se, Te, S(=O), S(=O) ２ , N.R. ａ , SiR ｂ R ｃ , or GeR ｄ R ｅ (where R ａ , R ｂ , R ｃ , R ｄ , and R ｅ are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof); Each hydrogen atom in the heteroaromatic ring is unsubstituted or substituted with deuterium, halogen, cyano, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, -SiH ３ and an alkylsilyl group having 1 to 10 carbon atoms.)

3. In the above Chemical Formula 1A, L １ and L ２ are each independently a heteroaromatic ring group selected from the following formulas 1A-16 to 1A-20, or a combination thereof. 【Chemical 1A-16-1A-20】 (In the above Chemical Formula 1A-16 to Chemical Formula 1A-20, X １ and X ２ are each independently O, S, Se, Te, S(=O), S(=O) ２ , N.R. ａ , SiR ｂ R ｃ , or GeR ｄ R ｅ (where R ａ , R ｂ , R ｃ , R ｄ , and R ｅ each independently represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z ４ are each independently ｘ or N, where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), provided that in Chemical Formula 1A-16 to Chemical Formula 1A-18, Z １ ~Z ４ One of them is CR ｘ and R ｘ is a single bond, Each hydrogen atom in the aromatic ring or heteroaromatic ring is unsubstituted or substituted with deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, -SiH ３ and an alkylsilyl group having 1 to 10 carbon atoms.)

4. Said L １ and L ２ are each independently a combination of a heteroaromatic ring group selected from Chemical Formula 1A-11 to Chemical Formula 1A-15 shown below and a heteroaromatic ring group selected from Chemical Formula 1A-16 to Chemical Formula 1A-20 shown below. 【Chemical 1A-11-1A-15】 (In the above Chemical Formula 1A-11 to Chemical Formula 1A-15, X １ , X ２ , and X ３ are each independently O, S, Se, Te, S(=O), S(=O) ２ , N.R. ａ , SiR ｂ R ｃ , or GeR ｄ R ｅ (where R ａ , R ｂ , R ｃ , R ｄ and R e are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof; Each hydrogen atom in the heteroaromatic ring is unsubstituted or substituted with deuterium, halogen, cyano, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, -SiH ３ and an alkylsilyl group having 1 to 10 carbon atoms.) 【Chemical 1A-16-1A-20】 (In the above Chemical Formula 1A-16 to Chemical Formula 1A-20, X １ and X ２ are each independently O, S, Se, Te, S(=O), S(=O) ２ , N.R. ａ , SiR ｂ R ｃ , or GeR ｄ R ｅ (where R ａ , R ｂ , R ｃ , R ｄ , and R ｅ each independently represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z ４ are each independently ｘ or N, where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), provided that in Chemical Formula 1A-16 to Chemical Formula 1A-18, Z １ ~Z ４ One of them is CR ｘ and R ｘ is a single bond, Each hydrogen atom in the aromatic ring or heteroaromatic ring is unsubstituted or substituted with deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, -SiH ３ and an alkylsilyl group having 1 to 10 carbon atoms.)

5. The compound according to claim 1, wherein, in Chemical Formula 1, Ar is a heteroaromatic ring group selected from the following Chemical Formulas 1B-11 to 1B-15. 【Chemical 1B-11-1B-15】 (In the above Chemical Formula 1B-11 to Chemical Formula 1B-15, X １ , X ２ , and X ３ are each independently O, S, Se, Te, S(=O), S(=O) ２ , N.R. ａ , SiR ｂ R ｃ , or GeR ｄ R ｅ (where R ａ , R ｂ , R ｃ , R ｄ , and R ｅ are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof); Each hydrogen atom in the heteroaromatic ring is unsubstituted or substituted with deuterium, halogen, cyano, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, -SiH ３ and an alkylsilyl group having 1 to 10 carbon atoms.)

6. The compound according to claim 1, wherein, in Chemical Formula 1, Ar is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms, or a fused ring thereof.

7. The compound according to claim 1, wherein, in Formula 1, Ar is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, acenaphthenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted tetracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalyl, substituted or unsubstituted quinazolyl, or substituted or unsubstituted phenanthrolyl.

8. The compound according to claim 1, wherein in Chemical Formula 1, the arylamine group or heteroarylamine group is represented by Chemical Formula 1C-1 below. 【Chemical 1C-1】 (In the above Chemical Formula 1C-1, Ar ２１ and Ar ２２ are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

9. The compound according to claim 8, wherein the formula 1C-1 is represented by the following formula 1C-1a or 1C-1b. 【Chemical 1C-1a】 (In the above Chemical Formula 1C-1a, Z １ ~Z １０ are each independently N or CR ｘ (where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z １０ is CR ｘ In the case of R ｘ are independently present, or Z １ ~Z １０ two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring. 【Chemistry 1C-1b】 (In the above Chemical Formula 1C-1b, X ａ and X ｂ each independently represents -O-, -S-, -Se-, -Te-, or -NR ａ --, --SiR ｂ R ｃ - and - GeR ｄ R ｅ - (where R ａ , R ｂ , R ｃ , R ｄ and R ｅ are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Z １ ~Z ６ are each independently N or CR ｘ (where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z ６ is CR ｘ In the case of R ｘ are independently present, or Z １ ~Z ６ two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

10. The compound according to claim 1, wherein in Chemical Formula 1, the heteroaromatic ring group is an N-containing heteroaromatic ring group represented by Chemical Formula 1C-2 below. 【Chemical 1C-2】 (In the above Chemical Formula 1C-2, Ar ２３ and Ar ２４ are each independently selected from a substituted or unsubstituted arene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarene group having 3 to 15 carbon atoms; G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR ａ --, --SiR ｂ R ｃ -, -GeR ｄ R ｅ -, - (CR ｆ R ｇ ) ｎ -, and -(C(R ｈ ) = C(R ｉ ))--wherein R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , and R ｉ are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R ｂ and R ｃ , R ｄ and R ｅ , R ｆ and R ｇ , or R ｈ and R ｉ each independently exists or are joined to each other to form a ring, - (CR ｆ R ｇ ) ｎ -n is an integer of 1 or 2).

11. The compound according to claim 10, wherein the formula 1C-2 is represented by the following formula 1C-2a, 1C-2b, or 1C-2c. 【Chemical 1C-2a】 (In the chemical formula 1C-2a, G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR ａ --, --SiR ｂ R ｃ -, -GeR ｄ R ｅ -, - (CR ｆ R ｇ ) ｎ -, and -(C(R ｈ ) = C(R ｉ ))--wherein R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ and R ｉ are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R ｂ and R ｃ , R ｄ and R ｅ , R ｆ and R ｇ , or R ｈ and R ｉ each independently exists or are linked to each other to form a ring; -(CR ｆ R ｇ ) ｎ -n is an integer of 1 or 2; Z １ ~Z ８ are each independently N or CR ｘ (where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z ８ is CR ｘ In the case of R ｘ are independently present, or Z １ ~Z ８ two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring. 【Chemical 1C-2b】 【Chemistry 1C-2c】 (In the above Chemical Formula 1C-2b and Chemical Formula 1C-2c, G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR ａ --, --SiR ｂ R ｃ -, -GeR ｄ R ｅ -, - (CR ｆ R ｇ ) ｎ -, and -(C(R ｈ ) = C(R ｉ ))--wherein R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , and R ｉ are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R ｂ and R ｃ , R ｄ and R ｅ , R ｆ and R ｇ , or R ｈ and R ｉ each independently exists or are linked to each other to form a ring; -(CR ｆ R ｇ ) ｎ -n is an integer of 1 or 2), X ａ and X ｂ each independently represents -O-, -S-, -Se-, -Te-, or -NR ｐ --, --SiR ｑ R ｒ - and - GeR ｓ R ｔ - (where R ｐ , R ｑ , R ｒ , R ｓ , and R ｔ are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Z １ ~Z ４ are each independently N or CR ｘ (where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z ４ is CR ｘ In the case of R ｘ are independently present, or Z １ ~Z ４ two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

12. The compound according to claim 1, wherein, in Chemical Formula 1, Ar is an aromatic ring group or a heteroaromatic ring group selected from the following Chemical Formulas 1B-16 to 1B-25. 【Chemical 1B-16-1B-25】 (In the above Chemical Formula 1B-16 to Chemical Formula 1B-25, X １ and X ２ are each independently O, S, Se, Te, S(=O), S(=O) ２ , N.R. ａ , SiR ｂ R ｃ , or GeR ｄ R ｅ (where R ａ , R ｂ , R ｃ , R ｄ , and R ｅ each independently represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z ４ are each independently ｘ or N, where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an arylamine group having 6 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), provided that in Chemical Formula 1B-20, Z １ ~Z ４ One of them is CR ｘ and R ｘ is a single bond, Ar １１ and Ar １２ are each independently selected from a substituted or unsubstituted arene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarene group having 3 to 30 carbon atoms; Each hydrogen atom in the aromatic ring or heteroaromatic ring is unsubstituted or substituted with deuterium, halogen, cyano group, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, aryl group having 6 to 10 carbon atoms, aryloxy group having 6 to 10 carbon atoms, -SiH ３ and an alkylsilyl group having 1 to 10 carbon atoms.)

13. The aromatic ring groups represented by Chemical Formula 1B-16 to Chemical Formula 1B-25 are arylamine groups or substituted with arylamine groups; The compound according to claim 12, characterized in that the arylamine group or arylamine group is represented by the following chemical formula 1C-1. 【Chemical 1C-1】 (In the above Chemical Formula 1C-1, Ar ２１ and Ar ２２ are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

14. The compound according to claim 13, wherein the formula 1C-1 is represented by the following formula 1C-1a or 1C-1b. 【Chemical 1C-1a】 (In the above Chemical Formula 1C-1a, Z １ ~Z １０ are each independently N or CR ｘ (where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z １０ is CR ｘ In the case of R ｘ are independently present, or Z １ ~Z １０ two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring. 【Chemistry 1C-1b】 (In the above Chemical Formula 1C-1b, X ａ and X ｂ each independently represents -O-, -S-, -Se-, -Te-, or -NR ａ --, --SiR ｂ R ｃ - and - GeR ｄ R ｅ - (where R ａ , R ｂ , R ｃ , R ｄ , and R ｅ are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Z １ ~Z ６ are each independently N or CR ｘ (where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z ６ is CR ｘ In the case of R ｘ are independently present, or Z １ ~Z ６ two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

15. The aromatic ring groups represented by Chemical Formulae 1B-16 to 1B-25 are substituted with an N-containing heterocyclic group; The compound according to claim 12, wherein the N-containing heterocyclic group is represented by the following formula 1C-2: 【Chemical 1C-2】 (In the above Chemical Formula 1C-2, Ar ２３ and Ar ２４ are each independently selected from a substituted or unsubstituted arene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarene group having 3 to 15 carbon atoms; G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR ａ --, --SiR ｂ R ｃ -, -GeR ｄ R ｅ -, - (CR ｆ R ｇ ) ｎ -, and -(C(R ｈ ) = C(R ｉ ))--wherein R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , and R ｉ are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R ｂ and R ｃ , R ｄ and R ｅ , R ｆ and R ｇ , or R ｈ and R ｉ each independently exists or are linked to each other to form a ring; -(CR ｆ R ｇ ) ｎ -n is an integer of 1 or 2.

16. The compound according to claim 15, wherein the formula 1C-2 is represented by the following formula 1C-2a, 1C-2b, or 1C-2c. 【Chemical 1C-2a】 (In the chemical formula 1C-2a, G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR ａ --, --SiR ｂ R ｃ -, -GeR ｄ R ｅ -, - (CR ｆ R ｇ ) ｎ -, and -(C(R ｈ ) = C(R ｉ ))--wherein R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , and R ｉ are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R ｂ and R ｃ , R ｄ and R ｅ , R ｆ and R ｇ , or R ｈ and R ｉ each independently exists or is linked to each other to form a ring; -(CR ｆ R ｇ ) ｎ -n is an integer of 1 or 2), Z １ ~Z ８ are each independently N or CR ｘ (where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z ８ is CR ｘ In the case of R ｘ are independently present, or Z １ ~Z ８ two adjacent ones of which are linked to each other to form a 5-membered or 6-membered aromatic ring. 【Chemical 1C-2b】 【Chemistry 1C-2c】 (In the above Chemical Formula 1C-2b and Chemical Formula 1C-2c, G is a single bond, -O-, -S-, -Se-, -Te-, -N=, -NR ａ --, --SiR ｂ R ｃ -, -GeR ｄ R ｅ -, - (CR ｆ R ｇ ) ｎ -, and -(C(R ｈ ) = C(R ｉ ))--wherein R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , and R ｉ are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; R ｂ and R ｃ , R ｄ and R ｅ , R ｆ and R ｇ , or R ｈ and R ｉ each independently exists or is linked to each other to form a ring; -(CR ｆ R ｇ ) ｎ -n is an integer of 1 or 2), X ａ and X ｂ each independently represents -O-, -S-, -Se-, -Te-, or -NR ｐ --, --SiR ｑ R ｒ - and - GeR ｓ R ｔ -, where R ｐ , R ｑ , R ｒ , R ｓ , , and R ｔ are each independently selected from hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Z １ ~Z ４ are each independently N or CR ｘ (where R ｘ represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -SiH ３ , an alkylsilyl group having 1 to 10 carbon atoms, —NH ２ , an alkylamine group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a halogen, a cyano group, or a combination thereof), Z １ ~Z ４ is CR ｘ In the case of R ｘ are independently present, or Z １ ~Z ４ two adjacent ones of these are linked to each other to form a 5-membered or 6-membered aromatic ring.

17. In the above formula 1, R １１ａ , R １１ｂ , R １１ｃ , R １２ａ , R １２ｂ , and R １２ｃ At least one of the functional groups represented by Chemical Formula 1A is R １３ａ , R １３ｂ , R １３ｃ , R １４ａ , R １４ｂ , and R １４ｃ The compound according to claim 1, characterized in that at least one of the functional groups is represented by the chemical formula 1A.

18. In the above formula 1, R １１ａ ~R １１ｃ At least one of the functional groups represented by Chemical Formula 1A is R １３ａ ~R １３ｃ The compound according to claim 1, characterized in that at least one of the functional groups is represented by the chemical formula 1A.

19. In the above formula 1, R １２ａ ~R １２ｃ At least one of the functional groups represented by Chemical Formula 1A is R １４ａ ~R １４ｃ The compound according to claim 1, characterized in that at least one of the functional groups is represented by the chemical formula 1A.

20. In the above formula 1, R １１ａ and R １３ａ The compound according to claim 1 , wherein:

21. In the above formula 1, R １２ａ and R １４ａ The compound according to claim 1 , wherein:

22. An infrared absorbing material comprising a compound according to any one of claims 1 to 21.

23. An infrared absorbing / blocking film comprising the compound according to any one of claims 1 to 21.

24. a first electrode and a second electrode facing each other; a photoactive layer located between the first electrode and the second electrode; 22. A photoelectric device, characterized in that the photoactive layer comprises a compound according to any one of claims 1 to 21.

25. The photoelectric device of claim 24 , wherein the photoactive layer further comprises fullerene or a fullerene derivative.

26. The photoelectric device according to claim 24, wherein the peak absorption wavelength of the photoactive layer is in the wavelength range of 750 nm to 3000 nm.

27. The semiconductor device includes a first electrode and a second electrode facing each other, a photoactive layer located between the first electrode and the second electrode, and a charge auxiliary layer between the first electrode and the photoactive layer or between the second electrode and the photoactive layer; 22. A photoelectric device, wherein at least one of the first electrode, the second electrode, the photoactive layer, or the charge auxiliary layer comprises a compound according to any one of claims 1 to 21.

28. The present invention includes a semiconductor substrate, a first photoelectric element disposed on the semiconductor substrate and configured to selectively absorb light in a first infrared wavelength region, and an additional sensor configured to selectively absorb light in another wavelength region different from the first infrared wavelength region, 22. An image sensor, wherein the first photoelectric element comprises a compound according to claim 1.

29. 28. An organic sensor comprising a photoelectric element according to any one of claims 24 to 27.

30. 30. An electronic device comprising the organic sensor of claim 29.

31. 28. An electronic device comprising a photoelectric element according to any one of claims 24 to 27.

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