N-type semiconductor composition and thin film, organic photoelectric element, image sensor and electronic device containing the same

Abstract

To provide an N-type semiconductor composition capable of improving color clarity of an organic photoelectric device.SOLUTION: The N-type semiconductor composition includes: fullerene or a fullerene derivative; and a fullerene subunit derivative represented by the chemical formula 1 shown in the figure. In the chemical formula 1, X, Cy and R1 to R8 are as defined in the specification.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an N-type semiconductor composition and a thin film, an organic photoelectric device, an image sensor and an electronic device including the same, and more particularly to an N-type semiconductor composition capable of improving the color vividness of an organic photoelectric device, and an organic photoelectric device, an image sensor and an electronic device including the same. [Background technology]

[0002] Fullerene is a molecule with a closed-cage structure made of carbon, and is used in various fields due to its stable structure and good electrical properties. The organic photoelectric device is a device that converts light into an electrical signal using a photoelectric effect, and includes a photodiode and a phototransistor, and can be applied to electronic devices such as an image sensor. Organic photovoltaic devices can include fullerenes in the active layer, which have high light absorption properties and good electrical properties.

[0003] However, fullerene has a problem in that it absorbs light in the blue region and may reduce the color clarity of an organic photoelectric device to which it is applied. Therefore, a method for controlling the absorption of fullerenes in the blue region is needed, and its development is a challenge. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2010-103457 A Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention has been made in consideration of the problems in the conventional organic photoelectric device, and an object of the present invention is to provide an N-type semiconductor composition that can improve the color vividness of an organic photoelectric device. Another object of the present invention is to provide an organic photoelectric device including the N-type semiconductor composition, and an image sensor and an electronic device including the organic photoelectric device. [Means for solving the problem]

[0006] In order to achieve the above object, the present invention provides an N-type semiconductor composition, which comprises a fullerene or a fullerene derivative, and a compound represented by the following chemical formula 1: 、 Cy in the above formula 1 is selected from the moieties represented by the following formula 2A: The present invention is characterized by having a fullerene subunit derivative. do.

[0007] [ka]

[0008] [ka]

[0009] In the chemical formula 1 and the chemical formula 2A, Y 1 is NR c and R c is a bulky substituent selected from a branched alkyl group having 3 to 7 carbon atoms and a substituted or unsubstituted aryl group having 6 carbon atoms; Z 1 and Z 2 is O, *=* is a moiety that is linked to Chemical Formula 1; X is R c and R 1 、R 3~R 6 , and R 8 are each independently hydrogen; R 2 and R 7 is a bulky substituent selected from a branched alkyl group having 4 carbon atoms, a branched alkoxy group having 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 carbon atoms. .

[0010] R c Branched chain alkyl groups having 3 to 7 carbon atoms , and The substituent of the substituted aryl group having 6 carbon atoms is an isopropyl group. R 2 and R 7 Branched chain alkoxy with 4 carbon atoms The base is , t-butoxy group, and Place The substituents of the substituted aryl group having 6 carbon atoms are , isopropyl group, or t -Butyl Based on It is preferable that there is.

[0014] According to another embodiment of the present invention, there is provided an N-type semiconductor composition comprising a fullerene or a fullerene derivative and a fullerene subunit derivative represented by any of the chemical formulae A to E shown below.

[0015] [ka] [ka] [ka] [ka] [ka]

[0016] Books According to another embodiment of the invention, a fullerene or fullerene derivative and Any one of the compounds represented in groups 1, 2, 4 and 5 and a fullerene subunit derivative represented by the formula: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0017] The thin film according to the present invention, which has been made to achieve the above object, is characterized by having the N-type semiconductor composition according to the present invention.

[0018] The extinction coefficient of the thin film at a wavelength of 450 nm is preferably less than the extinction coefficient of a thin film containing unsubstituted C60 fullerene at a wavelength of 450 nm.

[0019] The organic photoelectric element according to the present invention, which has been made to achieve the above object, comprises a first electrode and a second electrode facing each other, and an organic layer disposed between the first electrode and the second electrode, and the organic layer contains the N-type semiconductor composition according to the present invention.

[0020] The organic layer preferably includes an active layer, the active layer preferably includes a P-type semiconductor and an N-type semiconductor forming a PN junction, and the N-type semiconductor preferably includes the N-type semiconductor composition. The fullerene subunit derivative preferably has an average distance from the P-type semiconductor of 6 Å or less.

[0021] In order to achieve the above object, an image sensor according to the present invention includes an organic photoelectric element according to the present invention. In order to achieve the above object, an electronic device according to the present invention is characterized by comprising an organic photoelectric element according to the present invention. Effect of the Invention

[0022] According to the N-type semiconductor composition and the organic photoelectric element, image sensor and electronic device including the same according to the present invention, the N-type semiconductor composition having the fullerene subunit derivative of Chemical Formula 1 can reduce the absorption of fullerene or fullerene derivative in the blue region, thereby suppressing the aggregation of fullerene or fullerene derivative, thereby improving the color clarity of the organic photoelectric element. [Brief description of the drawings]

[0023] [Figure 1] 1 is a cross-sectional view illustrating an organic photoelectric device according to an embodiment of the present invention. [Diagram 2] 11 is a cross-sectional view showing a photoelectric device according to another embodiment of the present invention; [Diagram 3] 1 is a plan view illustrating a schematic configuration of a CMOS image sensor according to an embodiment of the present invention; [Figure 4] FIG. 4 is a cross-sectional view showing an example of the CMOS image sensor of FIG. [Diagram 5] FIG. 11 is a cross-sectional view showing another example of a CMOS image sensor. [Figure 6] FIG. 11 is a cross-sectional view showing another example of a CMOS image sensor. [Figure 7]11 is a plan view illustrating a schematic configuration of a CMOS image sensor according to another embodiment of the present invention. [Figure 8] 11 is a cross-sectional view of a CMOS image sensor according to yet another embodiment of the present invention. [Figure 9] 1 is a block diagram of a digital camera including an image sensor according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0024] Next, specific examples of embodiments for implementing the N-type semiconductor composition according to the present invention, and the organic photoelectric device, image sensor and electronic device including the same will be described with reference to the drawings.

[0025] In the drawings, the thicknesses of layers and regions are exaggerated for clarity, and like parts are designated by the same reference numerals throughout the specification. When a part such as a layer, film, region, or plate is said to be "on" another part, this includes not only the part "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 order to clearly explain the present embodiment in the drawings, parts unnecessary for the explanation are omitted, and the same reference numerals are used throughout the specification to refer to the same or similar components. Hereinafter, a 'combination' includes mixtures of two or more, substitutions with one another, and stacked structures of two or more.

[0026] Unless otherwise defined in this specification, “substituted” means that a hydrogen atom of a compound, functional group, or moiety is substituted with a halogen (-F, -Cl, -Br, -I), a hydroxyl group, a nitro group, a cyano group, an amino group, an azide group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamoyl group, a thiol group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl ... It means that the alkyl group is substituted with a substituent selected from an alkyl group, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, an alkoxy group having 1 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 (for example, a haloalkyl group having 1 to 20 carbon atoms, such as a trifluoroalkyl group having 1 to 20 carbon atoms).

[0027] Unless otherwise defined in this specification, 'hetero' means that a compound, functional group, or moiety contains 1-3 heteroatoms selected from N, O, S, P, and Si, with the remainder being carbon. 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, such as a phenyl group or naphthyl group, have p-orbitals and these p-orbitals form a conjugation, such as a form in which two or more hydrocarbon aromatic moieties, such as a biphenyl group, a terphenyl group, or a quaterphenyl group, are linked through a sigma bond, and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties, such as a fluorenyl group, are directly or indirectly fused.

[0028] Unless otherwise defined in this specification, the term "heterocyclic group" refers to a generic concept including a heteroaryl group having 2 to 30 carbon atoms (e.g., 2 to 20 carbon atoms), a heterocycloalkyl group having 2 to 30 carbon atoms (e.g., 2 to 20 carbon atoms), or a fused ring group thereof, and refers to a group containing one or more heteroatoms (e.g., 1 to 3) instead of carbon (C) in a ring such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, where the heteroatom may be, for example, but is not limited to, N, O, S, P, Se, Te and / or Si. When the heterocycle is a fused ring, the entire heterocycle group or each individual ring can contain one or more (eg 1 to 3) heteroatoms.

[0029] Unless otherwise defined herein, a 'heteroaryl group' means an aryl group containing one or more heteroatoms, which may be, for example, but not limited to, N, O, S, P, Se, Te and / or Si. Two or more heteroaryl groups may be directly linked through a sigma bond, or two or more heterocycles may be fused together. When the heteroaryl group is a fused ring, each ring can contain 1 to 3 of said heteroatoms. Unless otherwise defined in this specification, a "heteroalkyl group" refers to an alkyl group containing one or more heteroatoms in the main chain, specifically, a methylene group such as -O-, -S-, -C(=O)-, -C(=S ... 2 It means an alkyl group substituted with at least one functional group selected from -, -OC(=O)-, and -C(=O)O-. Unless otherwise defined in this specification, a 'cyclic hydrocarbon group' can include an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a fused ring group thereof, or a heterocyclic group containing a heteroatom.

[0030] Unless otherwise defined in this specification, the term "alicyclic hydrocarbon group" means at least one non-aromatic ring (alicyclic ring) selected from a cycloalkyl group having 3 to 30 carbon atoms, for example, a cycloalkyl group having 3 to 20 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 30 carbon atoms, for example, a cycloalkenyl group having 3 to 20 carbon atoms or a cycloalkenyl group having 3 to 10 carbon atoms, and a heterocycloalkyl group having 2 to 30 carbon atoms, for example, a heterocycloalkyl group having 2 to 20 carbon atoms or a heterocycloalkyl group having 3 to 10 carbon atoms, or a fused ring in which these non-aromatic rings are linked to each other. Unless otherwise defined in this specification, an 'aromatic hydrocarbon group' may contain at least one aromatic ring (arene ring) or a fused ring thereof, such as an aryl group having 6 to 30 carbon atoms, for example, an aryl group having 6 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms. Unless otherwise defined in the specification, a 'bulky substituent' may be a substituted or unsubstituted branched alkyl group, a substituted or unsubstituted linear or branched alkoxy group, a substituted or unsubstituted linear or branched alkylsilyl group, a substituted or unsubstituted linear or branched heteroalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, or a combination thereof. In one embodiment, the 'bulky substituent' may be a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms (e.g., 4 to 20 carbon atoms), a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms (e.g., 4 to 20 carbon atoms), a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms (e.g., 4 to 20 carbon atoms), a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms (e.g., 4 to 20 carbon atoms), a substituted or unsubstituted aryl group having 6 to 30 carbon atoms (e.g., 6 to 20 carbon atoms), a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms (e.g., 3 to 20 carbon atoms), a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms (e.g., 4 to 20 carbon atoms), a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms (e.g., 4 to 20 carbon atoms), and combinations thereof. As used herein, 'at least one of A, B, or C', 'one of A, B, C, or a combination thereof', and 'one of A, B, C, and a combination thereof' refer to each and every component and combination thereof (e.g., A; B; A and B; A and C; B and C; or A, B, and C).

[0031] Hereinafter, an N-type semiconductor composition according to one embodiment of the present invention will be described. According to one embodiment of the present invention, there is provided an N-type semiconductor composition comprising a fullerene or a fullerene derivative, and a fullerene subunit derivative represented by Chemical Formula 1 shown below. [ka]

[0032] In the above chemical formula 1, Cy is a cyclic hydrocarbon group or a condensed ring group of two or more cyclic hydrocarbon groups selected from an alicyclic hydrocarbon group having 3 to 20 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms; X is at least one bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; R 1 ~R 8each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R 1 ~R 8 At least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof.

[0033] The fullerene subunit derivative of formula 1 includes a hydrocarbon ring group (Cy) having at least one bulky substituent (X) and at least one (R 1 ~R 8 By further containing a bulky substituent such as at least one of the following, the crystallinity of the fullerene subunit derivative can be effectively suppressed, and by effectively interacting with the fullerene or fullerene derivative, aggregation of the fullerene or fullerene derivative can be suppressed. By suppressing the aggregation of fullerene or fullerene derivatives, the light absorption in the blue region (400 nm to 500 nm) can be significantly reduced, improving the color vividness of the device.

[0034] The bulky substituent (X) can effectively adjust the steric hindrance between the fullerene subunit derivatives to maintain a certain distance. R 1 ~R 8 A bulky substituent present in at least one of the above reduces the crystallinity of the fullerene subunit derivative, and the fullerene subunit derivative is well mixed with the P-type semiconductor and N-type semiconductor (fullerene or fullerene derivative) in the active layer. Also, R 1 ~R 8 The bulky substituent present in at least one of the groups can suppress aggregation of the fullerene or fullerene derivative by allowing the corannulene skeleton of the derivative to surround the fullerene or fullerene derivative well. Also, R 1 ~R 8 At least one bulky substituent among these can improve the thermal stability of the fullerene subunit derivative, and can improve the high temperature properties when applied to a device.

[0035] The fullerene subunit derivative of Chemical Formula 1 has a structure that can inhibit aggregation of fullerene or fullerene derivatives, and by not extending the conjugated structure of corannulene, it is possible to suppress an increase in crystallinity and to perform sublimation purification, which is advantageous for the thin film formation process. Cyclic hydrocarbon groups contain one or more heteroatoms in the ring. Specifically, the cyclic hydrocarbon group is -N=, -NR-, -O-, -S-, -Se-, -Te-, -C(=O)-, -C(=S)-, -C(=Se)-, -C(=Te)-, -C(=C(CN) 2 )-, and -C(=NR), where R is an alkyl group having 1 to 10 carbon atoms. In this way, when Cy is a heterocyclic group, the N-type characteristics of the fullerene subunit derivative can be further enhanced.

[0036] The HOMO / LUMO levels of the fullerene subunit derivative can be adjusted by the combination of the cyclic hydrocarbon group and the bulky substituent (X) substituted thereon. For example, when Cy is a hydrocarbon group that does not contain an electron-withdrawing functional group (eg, -C(=O)-, -N=, -NR-, etc.), an electron-withdrawing functional group is introduced into the bulky substituent (X). Examples of the bulky substituent (X) having an electron-withdrawing functional group include N-containing ring groups such as pyrrolyl, pyridyl, pyrimidinyl, and triazinyl groups, or fluorine (F) groups, cyano (CN) groups, carboxyl groups having 1 to 10 carbon atoms or ester groups thereof (e.g., acetate groups), and trifluoroalkyl groups having 1 to 10 carbon atoms (e.g., trifluoromethyl (CF 3 )) is an aryl group having 6 to 20 carbon atoms substituted with.

[0037] R 1 ~R 8 At least two of these, for example, three or four, may be bulky substituents selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof.

[0038] R in Chemical Formula 1 1 ~R 3 At least one of, and R 6 ~R 8at least one of them may be the same or different and may be a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof.

[0039] R 1 ~R 3 At least one bulky substituent selected from the group consisting of 6 ~R 8 At least one bulky substituent among may be located symmetrically with respect to Cy. R in Chemical Formula 1 1 ~R 8 At least two of the groups may be bulky substituents selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof. When the fullerene subunit derivative contains two or more bulky substituents at symmetric positions with respect to Cy in Chemical Formula 1, the fullerene subunit derivative can effectively surround the fullerene or fullerene derivative, thereby suppressing their aggregation.

[0040] The fullerene is a fullerene having 60 to 120 carbon atoms, and specifically may be C60, C70, C74, C76, C78, ​​C80, C82, C84, C90 or C96, but is not limited thereto. The fullerene derivative means a compound having a substituent on a fullerene. Examples of the substituent may be an alkyl group, an aryl group or a heterocyclic group. The alkyl group is an alkyl group having 1 to 12 carbon atoms, for example, an alkyl group having 1 to 5 carbon atoms. The aryl group can be a phenyl group, a naphthyl group or an anthracenyl group. Here, the heterocyclic group can be a furyl group, a thienyl group, a pyrrolyl group, an oxazolyl group, a pyridyl group, a quinolyl group or a carbazolyl group. Specific examples of fullerene derivatives include, but are not limited to, phenyl-C61-butyric acid methylester (PCBM), ICBA (indene-C60 bisadduct), and ICMA (indene-C60 monoadduct).

[0041] R in Chemical Formula 1 1 ~R 3 At least one of and R 6 ~R 8 at least one of them may be the same or different and may be a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof. In this case, the steric hindrance can be effectively adjusted to suppress aggregation of fullerene or fullerene derivatives during the deposition process.

[0042] R in Chemical Formula 1 1 and R 2 At least one of and R 7 and R 8at least one of them is the same or different and is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R 3 , R 4 , R 5 and R 6 can be hydrogen, deuterium, a halogen, a cyano group, a linear alkyl group having 1 to 20 carbon atoms, or a combination thereof. In this case, the steric hindrance can be effectively adjusted to suppress aggregation of fullerene or fullerene derivatives during the deposition process.

[0043] R in Chemical Formula 1 2 and R 7 is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R 1 , R 3 , R 4 , R 5 , R 6 and R 8 can be hydrogen, deuterium, a halogen, a cyano group, a linear alkyl group having 1 to 20 carbon atoms, or a combination thereof. In this case, the steric hindrance effect can be effectively controlled by having bulky substituents on both sides of Cy, thereby suppressing aggregation of fullerene or fullerene derivatives during deposition.

[0044] According to one embodiment, R in Formula 1 1 ~R 3 and R 6 ~R 8 Two adjacent substituents among these are linked to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms. Such an alicyclic hydrocarbon group having 3 to 20 carbon atoms can block the expansion of the conjugated structure of corannulene, thereby suppressing an increase in crystallinity. An alicyclic hydrocarbon group having 3 to 20 carbon atoms is present in a condensed form with an aromatic hydrocarbon group having 6 to 20 carbon atoms.

[0045] R in Chemical Formula 1 2 and R 3 are linked together to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and R 6 and R 7 are linked to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms. An alicyclic hydrocarbon group having 3 to 20 carbon atoms is present in a condensed form with an aromatic hydrocarbon group having 6 to 20 carbon atoms. The structure in which an alicyclic hydrocarbon group having 3 to 20 carbon atoms is a 5-membered ring and a condensed benzene ring is as shown in Chemical Formula 1A below. [ka]

[0046] In the above chemical formula 1A, Cy is a cyclic hydrocarbon group or a condensed ring group of two or more cyclic hydrocarbon groups selected from an alicyclic hydrocarbon group having 3 to 20 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms; X is at least one bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; R 1 , R 2a , R 4 , R 5 , R 6a and R 8 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; a1 and a2 each independently represents an integer of 1 to 4.

[0047] Cy in Chemical Formula 1 may be pyrrole, furan, pyrroline, pyrrolidinedione, cyclopentanediene, cyclopentanedione, pyrroloimidazole, pyrroloimidazole containing a ketone (C=O) group in the ring, pyridine, pyrimidine, indole, pyridine, phthalimide, benzimidazole, benzothiazole, or a condensed ring of any of these with a benzene ring.

[0048] Cy in Formula 1 can be selected from the moieties represented by Formula 2A shown below. [ka]

[0049] In the above chemical formula 2A, Y 1 CR a R b or NR c and R a and R b each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R a and R b at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R cis a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; Z 1 and Z 2 are O, S, Se, Te, and C(CN) 2 and N.R. d is selected from Here, R d is an alkyl group having 1 to 10 carbon atoms, or Y in Chemical Formula 2A 1 can be linked to form a fused ring, *=* is the moiety that is linked to Chemical Formula 1.

[0050] For example, the moiety represented by formula 2A can be a moiety represented by formula 2A-1, shown below. [ka]

[0051] In the above chemical formula 2A-1, R a and R b each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R aand R b at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R c is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0052] Z 2 NR d and R d is Y in formula 2A 1 When linked to form a fused ring, it can be a moiety represented by formula 2A-2, shown below. [ka]

[0053] In the above chemical formula 2A-2, Y 1 CR a or N, Z 1 are O, S, Se, Te, and C(CN) 2 and NR; Ar is an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms.

[0054] Cy in Chemical Formula 1 can be selected from the moieties represented by Chemical Formula 2B shown below. [ka]

[0055] In the above chemical formula 2B, Y 2 CR a R b , N.R. c , O, S, Se, and Te; Here, R a , R b and R c each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x is hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; Y 2 CR a R b or NRc In the case of R a , R b and R x At least one of and R c and R x at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; Y 2 When is O, S, Se or Te, R x is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0056] For example, the moiety represented by formula 2B can be a moiety represented by formula 2B-1, shown below. [ka]

[0057] In the above chemical formula 2B-1, R a , R b and R ceach independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x is hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R a , R b and R x At least one of and R c and R x at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0058] For example, the moiety represented by formula 2B can be a moiety represented by formula 2B-2 shown below. [ka]

[0059] In the above chemical formula 2B-2, R x is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0060] Cy in Chemical Formula 1 can be selected from the moieties represented by Chemical Formula 2C shown below. [ka]

[0061] In the above chemical formula 2C, Y 2 CR a R b , N.R. c , O, S, Se and Te; Here, R cis hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x and R y is hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; Y 2 NR c In the case of R a , R b , R x and R y At least one of and R c , R x and R y at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; Y 2If is O, S, Se or Te, then R x and R y at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0062] For example, the moiety represented by formula 2C can be a moiety represented by formula 2C-1, shown below. [ka]

[0063] In the above chemical formula 2C-1, R c is hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x and R yis hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R c , R x and R y at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0064] For example, the moiety represented by formula 2C can be a moiety represented by formula 2C-2 shown below. [ka]

[0065] In the above chemical formula 2C-2, R x and R yis hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x and R y at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0066] Cy in Chemical Formula 1 can be selected from moieties represented by Chemical Formulas 3A to 3D shown below. [ka]

[0067] In the above chemical formula 3A, R x , R y and R zeach independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x , R y and R z at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0068] [ka] In the above chemical formula 3B, R x and R yeach independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x and R y at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0069] [ka] In the above chemical formula 3C, R x and R yeach independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x and R y at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0070] [ka] In the above chemical formula 3D, R x and R yeach independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x and R y at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; *=* is the moiety that is linked to Chemical Formula 1.

[0071] Cy in Formula 1 can be selected from the moieties represented by Formula 4A shown below. [ka]

[0072] In the above chemical formula 4A, Y 1 CR a R b or NR c and R a and R beach independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R a and R b at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R c is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R p , R q , R r and R s are each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, n is an integer from 0 to 2, Z 1 and Z 2are O, S, Se, Te, and C(CN) 2 , and N.R. d is selected from Here, R d is an alkyl group having 1 to 10 carbon atoms, or Y in formula 4A 1 can be linked to form a fused ring, *=* is the moiety that is linked to Chemical Formula 1.

[0073] For example, the moiety represented by formula 4A can be a moiety represented by formula 4A-1, shown below. In the chemical formula 4A-1 shown below, only the case where n in the chemical formula 4A is 0 is shown, but the case where n is 1 or 2 is also similarly represented by the chemical formula 4A-1 shown below. [ka]

[0074] In the above chemical formula 4A-1, R a and R b each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R a and R bat least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R c is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R p and R q are each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, *=* is the moiety that is linked to Chemical Formula 1.

[0075] Cy in Formula 1 can be selected from the moieties represented by Formula 4B shown below. [ka]

[0076] In the above chemical formula 4B, Y 2 CR a R b , N.R. c , O, S, Se, and Te; Here, R a , R b and R ceach independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x is hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; Y 2 CR a R b or NR c In the case of R a , R b and R x At least one of and R c and R x at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; Y 2When is O, S, Se or Te, R x is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R p , R q , R r and R s are each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, n is an integer from 0 to 2, *=* is the moiety that is linked to Chemical Formula 1.

[0077] For example, the moiety represented by formula 4B can be a moiety represented by formula 4B-1, shown below. In the chemical formula 4B-1 shown below, only the case where n in the chemical formula 4B is 0 is shown, but the case where n is 1 or 2 is also similarly represented by the chemical formula 4B-1 shown below. [ka]

[0078] In the above chemical formula 4B-1, R a and R beach independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x is hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R a , R b and R x At least one of and R c and R x at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R p and R q are each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, *=* is the moiety that is linked to Chemical Formula 1.

[0079] For example, the moiety represented by formula 4B can be a moiety represented by formula 4B-2 shown below. In the chemical formula 4B-2 shown below, only the case where n in chemical formula 4B is 0 is shown, but the case where n is 1 or 2 is also similarly represented by the chemical formula 4B-2 shown below. [ka]

[0080] In the above chemical formula 4B-2, R x is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R p and R q are each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, *=* is the moiety that is linked to Chemical Formula 1.

[0081] Cy in Chemical Formula 1 can be selected from the moieties represented by Chemical Formula 4C shown below. [ka]

[0082] In the above chemical formula 4C, Y 2 CR a R b , N.R. c , O, S, Se, and Te; Here, Ra , R b and Rc each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x and R y is hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; Y 2 CR a R b or NR c In the case of R a , R b , R x and R y At least one of and R c , R x and R yat least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; Y 2 When is O, S, Se or Te, R x and R y at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R p , R q , R r and R s are each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, n is an integer from 0 to 2, *=* is the moiety that is linked to Chemical Formula 1.

[0083] For example, the moiety represented by formula 4C can be a moiety represented by formula 4C-1, shown below. In the chemical formula 4C-1 shown below, only the case where n in the chemical formula 4C is 0 is shown, but the case where n is 1 or 2 is also similarly represented by the chemical formula 4C-1 shown below. [ka]

[0084] In the above chemical formula 4C-1, R c is hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x and R y is hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R c , R x and R y at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R p and R qare each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, *=* is the moiety that is linked to Chemical Formula 1.

[0085] For example, the moiety represented by formula 4C can be a moiety represented by formula 4C-2 shown below. In the chemical formula 4C-2 shown below, only the case where n in the chemical formula 4C is 0 is shown, but the case where n is 1 or 2 is also similarly represented by the chemical formula 4C-2 shown below. [ka]

[0086] In the above chemical formula 4C-2, R x and R y is hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched heteroalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, or a combination thereof; R x and R y at least one of the groups is a bulky substituent selected from a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted branched heteroalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and combinations thereof; R p and R qare each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, *=* is the moiety that is linked to Chemical Formula 1.

[0087] In one embodiment of the present invention, the substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms and the substituted or unsubstituted branched alkoxy group having 3 to 20 carbon atoms are represented by Chemical Formula 5A shown below. [ka]

[0088] In the above chemical formula 5A, R a and R b is a hydrogen atom, a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms, n1 is an integer from 0 to 10, R 11 ~R 13 is hydrogen, halogen, a cyano group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, or an alkylsilyl group having 1 to 10 carbon atoms; R 11 ~R 13 At least two of them are an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms.

[0089] In one embodiment of the present invention, the branched alkyl group having 3 to 20 carbon atoms is an isopropyl group, a 1-methylpropyl group, an isobutyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a 1-propylbutyl group, an isopentyl group, a 1-methylpentyl group, a 1-ethylpentyl group, a 1-propylpentyl group, a 2-methylpentyl group, a 2-ethylpentyl group, a 2-propylpentyl group, a 3-methylpentyl group, a 3-ethylpentyl group, a 3-propylpentyl group, an isohexyl group, a 1-methylhexyl group, a 1-ethylhexyl group, a 1-propylhexyl group, a 2-methylhexyl group, a 2-ethylhexyl group, a 2-propylhexyl group, a 3-methylhexyl group, a 3-ethylhexyl group, a 3-propylhexyl group, The alkyl group may be, but is not limited to, an isoheptyl group, a 1-methylheptyl group, a 1-ethylheptyl group, a 1-propylheptyl group, a 2-methylheptyl group, a 2-ethylheptyl group, a 2-propylheptyl group, a 3-methylheptyl group, a 3-ethylheptyl group, a 3-propylheptyl group, an isooctyl group, a 1-methyloctyl group, a 1-ethyloctyl group, a 1-propyloctyl group, a 2-methyloctyl group, a 2-ethyloctyl group, a 2-propyloctyl group, a 3-methyloctyl group, a 3-ethyloctyl group, a 3-propyloctyl group, a 1-methylnonyl group, a 1,1-dimethylnonyl group, a t-butyl group, a t-pentyl group, a t-hexyl group, a neopentyl group, or a neohexyl group.

[0090] In one embodiment of the present invention, the branched heteroalkyl group having 3 to 20 carbon atoms is represented by -C(R c R d )- instead of -O-, -S-, -S(=O)-, -S(=O) 2 A functional group substituted with a functional group selected from -, -C(=O)-, -C(=O)O-, -OC(=O)-, and combinations thereof, and is represented by chemical formula 5B shown below. [ka]

[0091] In the above chemical formula 5B, R c and R drepresents hydrogen, halogen, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an ether group having 2 to 10 carbon atoms, or an ester group having 2 to 10 carbon atoms, n2 is an integer from 2 to 10, R 21 ~R 23 is a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms; R 21 ~R 23 At least two of them are an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms.

[0092] In one embodiment of the present invention, the substituted or unsubstituted branched alkylsilyl group having 3 to 20 carbon atoms is represented by the following chemical formula 5C. [ka]

[0093] In the above chemical formula 5C, R e and R f is a hydrogen atom, a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms, n3 is an integer from 0 to 10, R 31 ~R 33 is hydrogen, halogen, a cyano group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, or an alkylsilyl group having 1 to 10 carbon atoms; R 31 ~R 33 At least two of them are an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms.

[0094] Specific examples of the fullerene subunit derivative include the compounds of Groups 1 to 8 shown below. [ka] [ka] [ka] [ka]

[0095] The two substituents (OtBu groups) of corannulene in Group 1 may be substituted with branched alkyl groups such as an isopropyl (iPr) group, a tert-butyl (tBu) group, a 2-methylpropyl group, or a trimethylsilyl (TMS) group.

[0096] In group 2, the two substituents (O t Bu group) instead of tert-butyl ( t In group 2, structures substituted with a trimethylsilyl (TMS) group are listed.

[0097] [ka] [ka] [ka]

[0098] [ka] [ka] [ka]

[0099] In group 4, the two substituents of the corannulene in group 1 (O t The structures in which a phenyl group is substituted instead of the Bu group are listed below. [ka] [ka] [ka]

[0100] In Group 4, the two phenyl (Ph) groups of the substituent of corannulene may be substituted with at least one substituent selected from a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 3 to 12 carbon atoms. A plurality of these substituents may be present, and in this case, they may be the same or different. The position of the substituents may be at the ortho, meta or para position.

[0101] For example, structures substituted with an isopropyl group or a t-butyl group at the ortho position are listed in Group 5 below. [ka] [ka] [ka]

[0102] The two substituents of group 1 corannulene (O t Bu group) may be substituted with a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms (for example, a pyridyl group, a pyrimidinyl group, a triazinyl group, a thienyl group, etc.). The position of the heteroatom (eg, nitrogen, sulfur, etc.) of the substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms may be located at the ortho, meta, or para position relative to the bonding position. The heteroaryl group may be substituted with at least one substituent selected from a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 3 to 12 carbon atoms.

[0103] Group 6 lists structures substituted with a pyridyl group as the heteroaryl group, and Group 7 lists structures substituted with a thienyl group, a furanyl group, a pyrrolyl group, a selenophenyl group, or a tellurophenyl group as the heteroaryl group. [ka] [ka] [ka] In Group 6, the pyridyl group may be substituted with at least one substituent selected from a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 3 to 12 carbon atoms.

[0104] [ka] In Group 7, the thienyl group, the furanyl group, the pyrrolyl group, the selenophenyl group or the tellurophenyl group may be substituted with at least one substituent selected from a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 12 carbon atoms and a heteroaryl group having 3 to 12 carbon atoms. In addition, the hydrogen of the pyrrolyl group may be substituted with at least one substituent selected from a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 3 to 12 carbon atoms.

[0105] A phenyl (Ph) group in Group 5, or a pyridyl group in Group 6, can be fused to the corannulene with an alicyclic hydrocarbon group such as cyclopentadiene. Such structures are listed in Group 8. [ka]

[0106] The fullerene subunit derivatives (N-type semiconductors) can have an average distance from the P-type semiconductor of about 6.0 Å or less, such as about 5.5 Å or less, or 5.0 Å or less. The fullerene subunit derivative can adjust the average distance to the P-type semiconductor within the above range by containing a bulky substituent (X) and a bulky substituent on the side. When the average distance with the P-type semiconductor is maintained within the above range, the fullerene subunit derivative (N-type semiconductor) and the P-type semiconductor are well mixed to form a bulk hetero junction (BHJ).

[0107] The fullerene subunit derivative may be included in an amount of 50 parts by volume, for example 60 parts by volume or more, or 70 parts by volume or more, and 150 parts by volume or less, for example 140 parts by volume or less, or 130 parts by volume or less, per 100 parts by volume of fullerene or fullerene derivative. The fullerene subunit derivative in the above range can effectively suppress aggregation of fullerenes or fullerene derivatives, thereby reducing unnecessary light absorption in the blue region and increasing light absorption in the green region. The fullerene subunit derivatives can be formed into thin films by vacuum deposition via sublimation along with the fullerene or fullerene derivative. During the deposition process, the inherent properties of the fullerene or fullerene derivative can be maintained, and the optical properties can be prevented from being deformed due to aggregation of the fullerene or fullerene derivative that occurs during the formation of a thin film.

[0108] A thin film manufactured using an N-type semiconductor composition including a fullerene or a fullerene derivative and a fullerene subunit derivative may have reduced abnormal absorption in the short wavelength region of visible light of about 400 nm to about 500 nm. For example, the absorption coefficient of a thin film comprising an N-type semiconductor composition at a wavelength of 450 nm may be less than the absorption coefficient of a thin film comprising an unsubstituted fullerene (e.g., C60 fullerene) at a wavelength of 450 nm, e.g., the absorption coefficient of a thin film comprising an N-type semiconductor composition at a wavelength of 450 nm may be about 75% or less than the absorption coefficient of a thin film comprising an unsubstituted fullerene (e.g., C60 fullerene) at a wavelength of 450 nm.

[0109] Hereinafter, an organic photoelectric device including the above-mentioned N-type semiconductor composition will be described. FIG. 1 is a cross-sectional view illustrating an organic photoelectric device according to an embodiment of the present invention. Referring to FIG. 1, an organic photoelectric device 100 according to an embodiment of the present invention includes a first electrode 10, a second electrode 20 facing each other, and an organic layer 30 located between the first electrode 10 and the second electrode 20.

[0110] A substrate (not shown) may be disposed on the first electrode 10 side, and is disposed on 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. One of the first electrode 10 and the second electrode 20 is an anode, and the other is a cathode. For example, the first electrode 10 is an anode and the second electrode 20 is a cathode.

[0111] At least one of the first electrode 10 and the second electrode 20 may be a light-transmitting electrode, which is made of a conductive oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO), aluminum tin oxide (AlTO), and fluorine-doped tin oxide (FTO), or a thin single-layer or multi-layer metal film. When either the first electrode 10 or the second electrode 20 is an opaque electrode, it is made of an opaque conductor such as aluminum (Al), silver (Ag) or gold (Au). As an example, the first electrode 10 and the second electrode 20 are both light-transmitting electrodes. As an example, the second electrode 20 is a light receiving electrode located on the side receiving light.

[0112] The organic layer 30 includes an active layer. The active layer is a layer where a P-type semiconductor and an N-type semiconductor form a PN junction. It receives light from the outside and generates excitons, and then separates the generated excitons into holes and electrons. The P-type semiconductor and the N-type semiconductor are light-absorbing materials that absorb at least a portion of light in the visible light region. For example, the P-type semiconductor is a light-absorbing material that can selectively absorb mainly any one of the wavelength regions of about 400 nm or more and less than 500 nm, the wavelength region of about 500 nm to 600 nm, and / or the wavelength region of about more than 600 nm and not more than 700 nm, and the N-type semiconductor is the above-mentioned N-type semiconductor composition.

[0113] As an example, a P-type semiconductor is a light-absorbing material that selectively mainly absorbs light in any one of the wavelength regions of about 400 nm or more and less than 500 nm, about 500 nm to 600 nm, and about 600 nm to 700 nm, and an N-type semiconductor is the aforementioned N-type semiconductor composition. As an example, the P-type semiconductor is a light absorbing material that selectively absorbs mainly light in the wavelength region of about 500 nm to 600 nm, and the N-type semiconductor is the above-mentioned N-type semiconductor composition. As an example, a P-type semiconductor is a light absorbing material that has a LUMO energy level of, for example, about 3.0 eV to 3.6 eV and a HOMO energy level of, for example, about 5.1 eV to 5.7 eV. Within the above range, a P-type semiconductor is, for example, a light absorbing material having a LUMO energy level of about 3.1 eV to 3.5 eV and a HOMO energy level of about 5.2 eV to 5.6 eV. As an example, a P-type semiconductor is a light-absorbing material having a core structure including, for example, an electron-donating moiety, a π-conjugated linking group, and an electron-accepting moiety. As such a P-type semiconductor, the compounds disclosed in U.S. Patent Application Publication No. 2018-0062112 may be used.

[0114] The P-type semiconductor is a compound having a core structure, and may include, for example, a compound represented by the following Chemical Formula 8, but is not limited thereto. [ka]

[0115] In the above chemical formula 8, Y is Se, Te, S, SO, SO 2 or SiR h R i and EDG is an electron donating group, EAG is an electron accepting group. R 21 , R 22 , R h and R i are each independently hydrogen or a monovalent substituent. Here, the monovalent substituent may be, for example, 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 substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a halogen, or a cyano group, but is not limited to these.

[0116] The P-type semiconductor may be, for example, a light absorbing material represented by the following formula 8A, but is not limited thereto. [ka]

[0117] In the above chemical formula 8A, Y is Se, Te, S, SO, SO 2 or SiR h R i and Ar p is a substituted or unsubstituted 5-membered ring, a substituted or unsubstituted 6-membered ring, or a fused ring of two or more of these, Ar 1a and Ar 2a each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Ar 1a and Ar 2a each independently exists, or G 1 can be linked by a linker to form a ring; Here, G 1 is a single bond, -(CR j R k ) n2 -, -O-, -S-, -Se-, -N=, -NR l -, -SiR m R n - and -GeR o R p - one selected from where n2 is 1 or 2; R 1a ~R 3a , R h ~Rp are each independently a hydrogen atom, 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 substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a halogen atom, or a cyano group.

[0118] The P-type semiconductor may be, for example, a light absorbing material represented by any one of the following chemical formulas 8A-1 to 8A-4, but is not limited thereto. [ka] [ka] [ka] [ka]

[0119] In the above chemical formulas 8A-1 to 8A-4, Y is Se, Te, S, SO, SO 2 or SiR h R i and Z 1 is O or CR q R r and Y 1 is N or CR s and Y 2 is O, S, Se, Te and C(R t )(CN), Y 3 is O, S, Se or Te, Y 4 is N or NR 18a and Y 5 CR 19a or C=CR 20a (CN), Ar 1a and Ar2a are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Ar 1a and Ar 2a each independently exists or are joined to each other to form a ring, R 1a ~R 3a , R 11a , R 12a , R 15a ~R 20a , R 24a , R 25a , R h , R i , R q ~R t each independently represents a hydrogen atom, 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 substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a halogen atom, or a cyano group; n1 is 0 or 1, m1 is 0 or 1, and m2 is an integer of 0-4.

[0120] The light-absorbing substance represented by any one of chemical formulas 8A-1 to 8A-4 may be, for example, one of the compounds listed in Groups 9 to 12 shown below, but is not limited thereto. [ka] [ka] [ka] [ka]

[0121] Of groups 9 to 12, a hydrogen atom present in each aromatic ring is substituted with a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms, a halogen, a cyano group, a cyano-containing group, and a combination thereof; R 16 , R 17 , R 18 , R 20 may each independently be a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms, a halogen atom, a cyano group, a cyano-containing group, or a combination thereof.

[0122] As the N-type semiconductor, the above-mentioned N-type semiconductor composition is used. The fullerene or fullerene derivative has a LUMO energy level, a HOMO energy level and a band gap energy effective for electrical matching with the P-type semiconductors described above. The P-type semiconductor and N-type semiconductor compositions are formed into the active layer by co-deposition by sublimation. For example, the light absorption characteristics of an active layer including an N-type semiconductor composition are different from those of an active layer including an unsubstituted fullerene (e.g., C60 fullerene), and the active layer including an N-type semiconductor composition has reduced abnormal light absorption in the short wavelength region of visible light, for example, about 400 nm to 500 nm. For example, the extinction coefficient at 450 nm wavelength of an active layer including an N-type semiconductor composition is smaller than the extinction coefficient at 450 nm wavelength of an active layer including an unsubstituted fullerene (e.g., C60 fullerene), e.g., the extinction coefficient at 450 nm wavelength of an active layer including an N-type semiconductor composition is, for example, about 75% or less of the extinction coefficient at 450 nm wavelength of an active layer including an unsubstituted fullerene (e.g., C60 fullerene).

[0123] The light absorption characteristics of the active layer are expressed by a combination of the light absorption characteristics of the P-type semiconductor and the light absorption characteristics of the N-type semiconductor composition. As a result, for example, an active layer including a P-type semiconductor that selectively absorbs light in a wavelength range of about 500 nm to 600 nm and an N-type semiconductor composition can easily separate absorption peaks and improve wavelength selectivity compared to an active layer including a P-type semiconductor that selectively absorbs light in a wavelength range of about 500 nm to 600 nm and an unsubstituted fullerene (e.g., C60 fullerene). Therefore, it can be effectively used in organic photoelectric devices that require wavelength selectivity. The active layer includes an intrinsic layer in which the above-mentioned P-type semiconductor and N-type semiconductor compositions are co-deposited, and the P-type semiconductor and N-type semiconductor compositions are included in a volume ratio of about 1:9 to 9:1, about 2:8 to 8:2, about 3:7 to 7:3, about 4:6 to 6:4, or about 5:5. The active layer may further include a P-type layer and / or an N-type layer in addition to the intrinsic layer. The P-type layer includes a P-type semiconductor composition as described above, and the N-type layer includes an N-type semiconductor composition as described above. For example, various combinations such as P-type layer / I layer, I layer / N-type layer, P-type layer / I layer / N-type layer, etc. may be included.

[0124] The organic photoelectric device 100 further includes a charge auxiliary layer (not shown) located between the first electrode 10 and the active layer and / or between the second electrode 20 and the active layer. An organic photoelectric device 200 having such a structure is shown in Fig. 2. Fig. 2 is a cross-sectional view illustrating an organic photoelectric device according to another embodiment. 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 an organic layer 30 located between the first electrode 10 and the second electrode 20, similar to the previous embodiments. However, unlike the previous embodiments, the photoelectric device 100 according to this embodiment further includes charge auxiliary layers 40, 45 between the first electrode 10 and the organic layer 30 and between the second electrode 20 and the organic layer 30, respectively. The charge auxiliary layers 40 and 45 can facilitate the movement of holes and electrons separated in the organic layer 30 to increase efficiency. The charge auxiliary layers 40 and 45 include at least one selected from a hole injecting layer (HIL) that facilitates hole injection, a hole transporting layer (HTL) that facilitates hole transport, an electron blocking layer (EBL) that blocks electron transport, an electron injecting layer (EIL) that facilitates electron injection, an electron transporting layer (ETL) that facilitates electron transport, and a hole blocking layer (HBL) that blocks hole transport.

[0125] The charge auxiliary layers 40, 45 can comprise, for example, organic, inorganic, or organic-inorganic. The organic material can be an organic compound having hole or electronic properties, and the inorganic material can be a metal oxide such as, for example, molybdenum oxide, tungsten oxide, nickel oxide, and the like. The charge auxiliary layers 40, 45 may include the N-type semiconductor compositions described above.

[0126] The organic photoelectric element 100 or 200 further includes an anti-reflection layer (not shown) on one surface of the first electrode 10 or the second electrode 20 . An anti-reflection layer can be disposed on the light-incident side to further improve light absorption by reducing the reflectance of incident light. For example, when light is incident on the first electrode 10 side, the anti-reflection layer 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 contains a substance having a refractive index of, for example, about 1.6 to 2.5, and contains, for example, at least one of a metal oxide, a metal sulfide, and an organic substance having a refractive index in the above range. The antireflective layer can include, but is not limited to, metal oxides such as, for example, 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.

[0127] In the organic photoelectric device 100, 200, when light is incident from the first electrode 10 or second electrode 20 side and the organic layer (eg, active layer) 30 absorbs the light in a predetermined wavelength region, excitons are generated inside. The excitons separate into holes and electrons in the organic layer 30, and the separated holes move to the anode side, which is one of the first electrode 10 and the second electrode 20, and the separated electrons move to the cathode side, which is the other of the first electrode 10 and the second electrode 20, causing a current to flow. The organic photoelectric device 100, 200 may be applied to, but is not limited to, a solar cell, an image sensor, a photodetector, a photosensor, an organic light emitting diode, and the like. The organic photoelectric element can be applied to, for example, an image sensor.

[0128] Hereinafter, an example of an image sensor to which an organic photoelectric element is applied will be described with reference to the drawings. Here, an organic CMOS image sensor will be described as an example of an image sensor. FIG. 3 is a plan view illustrating a schematic configuration of an organic CMOS image sensor according to an embodiment of the present invention, and FIG. 4 is a cross-sectional view illustrating an example of the organic CMOS image sensor of FIG. 3 and 4, an organic CMOS image sensor 300 according to an embodiment of the present invention includes a semiconductor substrate 110 in which photo-sensing elements (50a, 50b), transfer transistors (not shown), and charge storages 55 are integrated, a lower insulating layer 60, a color filter layer 70, an upper insulating layer 80, and an organic photoelectric element 100.

[0129] The semiconductor substrate 110 is a silicon substrate on which the light sensing elements (50a, 50b), the transfer transistor (not shown), and the charge reservoir 55 are integrated. The light sensing elements (50a, 50b) are photodiodes. A light sensing element (50a, 50b), a transfer transistor and / or a charge reservoir 55 are integrated for each pixel, and by way of example, as shown in the figure, a light sensing element (50a, 50b) is included in the blue pixel and the red pixel, respectively, and a charge reservoir 55 is included in the green pixel. The light sensing elements (50a, 50b) sense light, and the sensed information is transmitted by a transmission transistor. The charge storage 55 is electrically connected to the organic photoelectric element 100 described later, and the information of the charge storage 55 is transmitted by the transmission transistor.

[0130] Metal wiring (not shown) and pads (not shown) are further 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 located under the photo-sensing elements 50a and 50b.

[0131] A lower insulating layer 60 is formed over the metal wiring and pads. The lower insulating layer 60 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 lower insulating layer 60 has a trench exposing the charge reservoir 55 . The trench is filled with a filling material.

[0132] A color filter layer 70 is formed on the lower insulating film 60 . The color filter layer 70 includes blue filters 70a formed in blue pixels and red filters 70b formed in red pixels. In this embodiment, an example in which a green filter is not provided will be described, but a green filter may be provided in some cases.

[0133] An upper insulating layer 80 is formed over the color filter layer 70 . The upper insulating layer 80 is formed to remove the steps caused by the color filter layer 70 and to flatten the surface. The upper insulating layer 80 and the lower insulating layer 60 have contact holes (not shown) exposing the pads and through holes 85 exposing the charge reservoirs 55 of the green pixels.

[0134] On the upper insulating layer 80, the above-mentioned organic photoelectric element 100 is formed. The organic photoelectric device 100 includes a first electrode 10, an organic layer 30, and a second electrode 20, as described above. In the drawings, a structure in which the first electrode 10, the organic layer 30, and the second electrode 20 are stacked in sequence is shown as an example, but this is not limited thereto, and the second electrode 20, the organic layer 30, and the first electrode 10 may also be arranged in this order. The first electrode 10 and the second electrode 20 are both transparent electrodes, and the organic layer 30 is as described above.

[0135] The organic layer 30 can selectively absorb light in the green wavelength region, for example, and can replace the color filter of a green pixel. Of the light incident from the second electrode 20 side, the light in the green wavelength region is mainly absorbed and photoelectrically converted by the organic layer 30, and the light in the remaining wavelength region passes through the first electrode 10 and is sensed by the light-sensing elements (50a, 50b). A condenser lens (not shown) is further disposed above the organic 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.

[0136] As described above, the organic photoelectric device 100 has a stacked structure, so that the size of the image sensor can be reduced, thereby realizing a miniaturized image sensor. In addition, as described above, the organic layer contains a fullerene derivative whose light absorption characteristics are shifted to the short wavelength side, thereby improving wavelength selectivity compared to the case where unsubstituted C60 fullerene is used.

[0137] Although the above describes an example of a structure in which organic photoelectric elements that selectively absorb light in the green wavelength region are stacked, the present invention is not limited thereto, and a structure in which organic photoelectric elements that selectively absorb light in the blue wavelength region are stacked and green and red light-sensing elements are integrated in the semiconductor substrate 110 may be used, or a structure in which organic photoelectric elements that selectively absorb light in the red wavelength region are stacked and green and blue light-sensing elements are integrated in the semiconductor substrate 110 may be used. 4 illustrates an example including the organic photoelectric device 100 of FIG 1, but is not limited thereto and may be similarly applied to a case including the organic photoelectric device 200 of FIG 2. FIG 5 is a cross-sectional view illustrating a CMOS image sensor 300' using the organic photoelectric device 200 of FIG 2.

[0138] FIG. 6 is a cross-sectional view showing another example of an organic CMOS image sensor. The organic CMOS image sensor 400 according to this embodiment includes a semiconductor substrate 110 in which photo-sensing elements (50a, 50b), transfer transistors (not shown) and charge storage elements 55 are integrated, an upper insulating layer 80 having a through hole 85, and an organic photoelectric element 100, similar to the above-described embodiments.

[0139] However, unlike the above-described embodiments, the organic CMOS image sensor 400 according to this embodiment has the photo-sensing elements 50a and 50b stacked vertically and does not include the color filter layer 70. The light-sensing elements (50a, 50b) are electrically connected to a charge reservoir (not shown) and are transmitted by a transfer transistor. The light-sensing elements (50a, 50b) can selectively absorb light in each wavelength region depending on the layer depth. A condenser lens (not shown) is further disposed above the organic 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.

[0140] As described above, by having a structure in which organic photoelectric elements that selectively absorb light in the green wavelength region are stacked and a structure in which red and blue light sensing elements are stacked, the size of the image sensor can be further reduced, thereby realizing a miniaturized image sensor. FIG. 6 illustrates an example of a structure in which organic photoelectric elements that selectively absorb light in the green wavelength region are stacked, but the present invention is not limited to this. A structure in which organic photoelectric elements that selectively absorb light in the blue wavelength region are stacked and green and red light-sensing elements are integrated in the semiconductor substrate 110 may be used, or a structure in which organic photoelectric elements that selectively absorb light in the red wavelength region are stacked and green and blue light-sensing elements are integrated in the semiconductor substrate 110 may be used.

[0141] FIG. 7 is a plan view illustrating an organic CMOS image sensor according to still another embodiment, and FIG. 8 is a cross-sectional view of the organic CMOS image sensor according to the another embodiment. The organic CMOS image sensor 500 according to this embodiment has a structure in which a green organic photoelectric element that selectively absorbs light in the green wavelength region, a blue organic photoelectric element that selectively absorbs light in the blue wavelength region, and a red organic photoelectric element that selectively absorbs light in the red wavelength region are stacked. The organic CMOS image sensor 500 according to the present embodiment includes a semiconductor substrate 110, a lower insulating layer 60, an intermediate insulating layer 65, an upper insulating layer 80, a first organic photoelectric element 100a, a second organic photoelectric element 100b, and a third organic photoelectric element 100c.

[0142] The semiconductor substrate 110 is a silicon substrate on which transfer transistors (not shown) and charge reservoirs (55a, 55b, 55c) are integrated. Metal wiring (not shown) and pads (not shown) are formed on the semiconductor substrate 110, and a lower insulating layer 60 is formed on the metal wiring and pads. The first organic photoelectric element 100a is formed on the lower insulating layer 60. The first organic photoelectric element 100a includes a first electrode 10a, a second electrode 20a facing each other, and an organic layer 30a located between the first electrode 10a and the second electrode 20a. The first electrode 10a, the second electrode 20a, and the organic layer 30a are as described above, and the organic layer 30a can selectively absorb light in any one of the wavelength regions of red, blue, and green. For example, the first organic photoelectric element 100a is a red organic photoelectric element. In the figure, a structure in which the first electrode 10a, the organic layer 30a, and the second electrode 20a are stacked in this order is shown as an example, but this is not limited to this, and the second electrode 20a, the organic layer 30a, and the first electrode 10a are arranged in this order.

[0143] An intermediate insulating layer 65 is formed on the first organic photoelectric element 100a. A second organic photoelectric element 100b is formed on the intermediate insulating layer 65. The second organic photoelectric element 100b includes a first electrode 10b, a second electrode 20b facing each other, and an organic layer 30b located between the first electrode 10b and the second electrode 20b. The first electrode 10b, the second electrode 20b, and the organic layer 30b are as described above, and the organic layer 30b can selectively absorb light in any one of the wavelength regions of red, blue, and green. For example, the second organic photoelectric element 100b is a blue organic photoelectric element. In the figure, a structure in which the first electrode 10b, the organic layer 30b, and the second electrode 20b are stacked in this order is shown as an example, but this is not limited to this, and the second electrode 20b, the organic layer 30b, and the first electrode 10b are arranged in this order.

[0144] An upper insulating layer 80 is formed on the second organic photoelectric element 100b. The lower insulating layer 60, the middle insulating layer 65, and the upper insulating layer 80 have a plurality of through holes exposing the charge reservoirs (55a, 55b, 55c). The third organic photoelectric element 100c is formed on the upper insulating layer 80. The third organic photoelectric element 100c includes a first electrode 10c, a second electrode 20c facing each other, and an organic layer 30c located between the first electrode 10c and the second electrode 20c. The first electrode 10c, the second electrode 20c, and the organic layer 30c are as described above, and the organic layer 30c selectively absorbs light in any one of the wavelength regions of red, blue, and green. For example, the third organic photoelectric element 100c can be a green organic photoelectric element. In the figure, a structure in which the first electrode 10c, the organic layer 30c, and the second electrode 20c are stacked in this order is shown as an example, but this is not limited to this, and the second electrode 20c, the organic layer 30c, and the first electrode 10c are arranged in this order.

[0145] A condenser lens (not shown) is further disposed above the organic photoelectric element 100c. 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. In the drawings, a structure in which the first organic photoelectric element 100a, the second organic photoelectric element 100b, and the third organic photoelectric element 100c are stacked in order is shown, but the stacking order is not limited thereto and may be variously changed.

[0146] As described above, the first organic photoelectric element 100a, the second organic photoelectric element 100b, and the third organic photoelectric element 100c, which absorb light in different wavelength regions, are stacked, thereby making it possible to further reduce the size of the image sensor and realize a miniaturized image sensor. The image sensor may be applied to various electronic devices, such as, but not limited to, mobile phones and digital cameras. FIG. 9 is a block diagram of a digital camera including an image sensor according to one embodiment. 9, a digital camera 1000 includes a lens 1010, an image sensor 1020, a motor 1030, and an engine 1040. The image sensor 1020 may be any of the image sensors according to the embodiments illustrated in FIGS. The lens 1010 focuses incident light onto the image sensor 1020. The image sensor 1020 generates RGB data from the light received through the lens 1010. In some embodiments, the image sensor 1020 may be interfaced with an engine 1040 . The motor 1030 may adjust the focus of the lens 1010 or adjust the shutter in response to a control signal received from the engine 1040. The engine 1040 may control the image sensor 1020 and the motor 1030. The engine 1040 is coupled to a host / application 1050 .

[0147] The above-described embodiment will now be described in more detail with reference to examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[0148] <Synthesis example: Synthesis of fullerene subunit derivatives> <Synthesis Example 1> [ka] [ka]

[0149] i) Phase 1 A suspension containing a 1,8-dibromocorannanulene derivative having dihydro-2,5-furandione (compound 1, 1.8 g, 3.8 mmol), isopropylamine (0.4 ml, 4.7 mmol) and N-methylpyrrolidone (NMP) (12 ml) was prepared and placed in a microwave reactor vessel. After reacting at 180° C. for 30 minutes, the suspension in the vessel was mixed. Next, NMP was removed by vacuum distillation (1 torr or less, temperature 50° C. or higher). Chloroform is then added to the residue, which is then purified by silica gel column chromatography (eluent: a mixture of chloroform and hexane (1:1 volume ratio)). After evaporating the solvent from the obtained solution, the solid was dissolved in chloroform and the product was separated using Recycle HPLC (Buckyprep 4.6φx250mm; eluent: chloroform). The solvent was evaporated from the solution to obtain an intermediate (compound 2) (0.7g, 1.4mmol, yield: 36.8%).

[0150] ii) Second stage The flask was charged with the intermediate (compound 2) (0.9 g, 1.7 mmol) and catalyst Pd(OAc). 2 (palladium(II) acetate, 6.5 mg, 0.3 mmol), base t BuONa(sodium tert-butoxide, 0.7g, 7.2mmol) and P( t Bu) 3 A toluene solution of (tri-tert-butylphosphine, 50 wt%, 0.3 ml, 0.6 mmol) and m-Xylene (78 ml) were mixed, and the mixture was stirred at 130° C. for 12 hours using an oil bath. Thereafter, the solvent was removed using an evaporator (300 mbar or less, temperature 40° C. or more). Next, chloroform was added to the residue, and the mixture was purified by silica gel column chromatography (eluent: a mixture of chloroform and hexane (volume ratio 1:1)). After evaporating the solvent from the obtained solution, the solid matter was dissolved in chloroform, and the product was separated using Recycle HPLC (Buckyprep 4.6φ×250 mm; eluent: chloroform). The solvent was evaporated from the above solution to obtain a compound represented by chemical formula A (compound 3) (0.6 g, 1.2 mmol, yield: 69.8%). 1 H NMR (CDCl 3 ):δ7.98(s, 1H), 7.95(s, 1H), 7.89(s, 2H), 7.75(s, 1H), 7.72(s, 1H), 4.50-4.60(m.1H), 1.70(s, 18H), 1.54(s, 3H), 1.52(s, 3H)

[0151] <Synthesis Example 2> [ka] [ka]

[0152] Compound (2) (1.5 g, 2.9 mmol) obtained in Synthesis Example 1, Pd(PPh 3 ) 4 (tetrakis(triphenylphosphine)palladium(0), 0.2g, 0.2mmol), Na 2 CO 3 (0.9g, 8.7mmol), phenylboronic acid (PhB(OH) 2 , 1.1 g, 8.7 mmol) and a mixed solvent (toluene 80 ml), EtOH (40 ml) and water (40 ml) were mixed, and then the mixture was stirred at 90°C for 12 hours using an oil bath to obtain a compound represented by chemical formula B (1.2 g, 2.3 mmol, yield: 78.7%). 1 H NMR (CDCl 3 ):δ8.55(s, 2H), 7.75-7.90(m, 6H), 7.10-7.65(m, 8H), 4.55-4.70(m, 1H), 1.58(s, 6H)

[0153] <Synthesis Example 3> [ka] [ka]

[0154] Compound (2) (1.0 g, 2.0 mmol) obtained in Synthesis Example 1, Pd(PPh 3 ) 4 (0.2g, 0.1mmol), Na 2 CO 3 (0.6 g, 5.9 mmol), phenylboronic acid ester (2-tert-butylphenylboronic acid pinacol ester, 0.3 g, 11.8 mmol) and a mixed solvent (toluene 72 ml), EtOH (32 ml) and water (32 ml) were mixed, and the mixture was stirred at 90°C for 12 hours using an oil bath to obtain a compound represented by chemical formula C (0.5 g, 0.8 mmol, yield: 40.6%). 1 H NMR (CDCl 3 ):δ8.35(s, 2H), 7.55-7.80(m, 4H), 7.00-7.50(m, 6H), 6.62(d, 2H), 4.40-4.62(m, 1H), 1.52(s, 24H)

[0155] <Synthesis Example 4> [ka] [ka]

[0156] i) Phase 1 In the first step of Synthesis Example 1, phenylamine (PhNH 2 An intermediate (compound 2) was synthesized (0.8 g, 1.5 mmol, yield: 38.9%) in the same manner as in Synthesis Example 1, except that ethyl acetate was used instead of ethyl acetate.

[0157] ii) Second stage The above intermediate (compound 2) (0.7 g, 1.3 mmol), Pd(PPh 3 ) 4 (0.1g, 0.1mmol), Na 2 CO 3 (0.4 g, 3.7 mmol), phenylboronic acid ester (2-tert-butylphenylboronic acid pinacolester, 1.9 g, 7.4 mmol) and a mixed solvent (toluene 44 ml), EtOH (20 ml) and water (20 ml) were mixed, and the mixture was stirred at 90°C for 12 hours using an oil bath to obtain a compound represented by chemical formula D (compound 3) (0.4 g, 0.6 mmol, yield: 50.1%). 1 H NMR (CDCl 3 ):δ8.35-8.45(m, 2H), 7.68-7.79(m, 4H), 7.43-7.56(m, 9H), 7.08-7.20(m, 2H), 6.60-6.68(m, 2H), 1.59(S, 9H)

[0158] <Synthesis Example 5> [ka] [ka]

[0159] i) Phase 1 In the first step of Synthesis Example 1, 2,6-diisopropylphenylamine ((iPr) 2 C 6 H 3 NH 2The intermediate (compound 2) was synthesized in the same manner as in Synthesis Example 1, except that ethyl acetate was used (0.9 g, 1.4 mmol, yield: 37.2%).

[0160] ii) Second stage Intermediate (compound 2) (1.2g, 1.8mmol), Pd(PPh 3 ) 4 (0.9g, 5.5mmol), Na 2 CO 3 (0.6 g, 5.5 mmol), phenylboronic acid ester (2-isopropylphenylboronic acid pinacol ester, 0.9 g, 5.5 mmol) and a mixed solvent (toluene 48 ml, EtOH 24 ml and water 24 ml) were mixed, and the mixture was reacted at 155°C for 1 hour using a microwave reactor to obtain a compound represented by chemical formula E (compound 3) (1.0 g, 1.4 mmol, yield: 75.8%). 1 H NMR (CDCl 3 ):δ7.34-7.40(m, 2H), 7.70-7.82(m, 2H), 7.42-7.62(m, 8H), 7.15-7.35 (m, 3H), 6.98-7.10(m, 2H), 2.72-2.85(m, 4H), 1.30(s, 6H), 1.20(s, 6H)

[0161] <Comparative Synthesis Example 1> [ka]

[0162] The compound represented by the chemical formula F was synthesized (0.1 g, 0.24 mmol, yield: 85%) in the same manner as in Scheme 2 of the above paper, except that Benzo[d]thiazol-5-ylboronic acid (128.9 mg, 0.72 mmol) was used instead of 9,9-dimethyl-fluorenyl-2-pinacolato boronic ester in Scheme 2 of the above paper. 1 H NMR (CDCl 3 ):δ7.76-7.73(m, 4H), 7.70(s, 2H), 7.64(d, J=7.92Hz, 2H), 7.58(s, 2H), 7.46(d, J=6.16Hz, 2H), 7.38-7.32(m, 4H), 1.55(s, 12H)

[0163] <Comparative Synthesis Example 2> [ka]

[0164] A compound represented by chemical formula G was synthesized (1.0 g, 2.7 mmol, yield: 38.0%) in the same manner as in Synthesis Example 10 described in the patent document "US2017-069690A1". 1 H NMR (DMSO-d6): δ8.70(d, 2H), 8.64(s, 2H), 8.11(t, 2H), 7.62-7.57(m, 4H)

[0165] <Comparative Synthesis Example 3> [ka]

[0166] A compound represented by the chemical formula H was synthesized (4.9 g, 10.1 mmol, yield: 42.0%) in the same manner as in Preparation Example 1 of the above-mentioned patent document "US2008-0142792A1", except that 2,3-dibromo-5-(trifluoromethyl)thiophene (3.1 g, 10.0 mmol) was used instead of 2,3-dibromothiophene in Preparation Example 1 (PREPARATIVE EXAMPLE 1) of the above-mentioned patent document. 1 H NMR(C 6 D 5 CD 3 )d7.80(d.2H), 7.45(s,4H)

[0167] <Comparative Synthesis Example 4> [ka] [ka]

[0168] In a flask, compound (2) (0.2 g, 0.3 mmol) obtained in Synthesis Example 1 and catalyst Pd(dba) 2 (bis(dibenzylideneacetone)palladium(0), 26.4 mg, 0.1 mmol), base Cs 2 CO 3 (17.8 mg, 0.8 mmol), SPhos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 20.9 mg, 50.9 μmol), m-Xylene (61 ml), and IPA (isopropyl alcohol, 5.0 ml) are mixed and stirred at 80°C for 12 hours using an oil bath. Thereafter, the solvent was removed using an evaporator (300 mbar or less, temperature 40° C. or more). Next, chloroform is added to the residue, and the mixture is purified by silica gel column chromatography (eluent: a mixture of chloroform and hexane (1:1 volume ratio)). After evaporating the solvent from the obtained solution, the solid matter was dissolved in chloroform, and the product was separated using Recycle HPLC (Buckyprep 4.6φ×250 mm; eluent: chloroform). The solvent was evaporated from the above solution to give the product (0.1 g, 0.2 mmol, yield: 60.2%). 1 H NMR (CDCl 3 ):δ8.45(d, 2H), 7.95(d, 2H), 7.85(d, 4H), 4.52-4.66(m, 1H), 1.55(s, 6H)

[0169] <Comparative Synthesis Example 5: C60 Fullerene> [ka]

[0170] C60 fullerene (trade name: nanom purple ST, manufactured by Frontier Carbon Corporation) was used.

[0171] ≪Example 1: Fabrication of Organic Optoelectronic Device≫ ITO was deposited on a glass substrate by sputtering to form an anode with a thickness of about 150 nm. On top of that, an N-type semiconductor composition containing a fullerene subunit derivative (N-type semiconductor compound) represented by Chemical Formula A according to Synthesis Example 1 and C60 fullerene represented by Chemical Formula J and a compound (P-type semiconductor compound) represented by Chemical Formula X shown below were co-evaporated to form an active layer with a thickness of 100 nm. The N-type semiconductor composition and the P-type semiconductor compound were used at a volume ratio of 1:1. The N-type semiconductor composition used the fullerene subunit derivative (N-type semiconductor compound) and C60 fullerene represented by Chemical Formula J at a volume ratio of 2:3. On top of that, a molybdenum oxide (MoOx, 0 < x ≦ 3) thin film was deposited as a charge assisting layer to a thickness of 10 nm. Next, ITO was deposited on the molybdenum oxide thin film by sputtering to form a cathode with a thickness of 7 nm, thereby fabricating an organic optoelectronic device.

Chemical Formula

[0172] ≪Examples 2 to 5 and Comparative Examples 4 and 5: Fabrication of Organic Optoelectronic Device≫ Organic optoelectronic devices were fabricated in the same manner as in Example 1, except that the fullerene subunit derivatives according to Synthesis Examples 2 to 5 and Comparative Synthesis Example 4 were used instead of the fullerene subunit derivative represented by Chemical Formula A according to Synthesis Example 1. An organic photoelectric device according to Comparative Example 5 was fabricated in the same manner as in Example 1, except that the fullerene subunit derivative represented by Formula A according to Synthesis Example 1 was not used, and C60 fullerene and a P-type semiconductor compound were co-deposited in a volume ratio of 1:1 to form an active layer.

[0173] <<Examples 6 to 10 and Comparative Examples 6 to 7: Fabrication of Organic CMOS Image Sensor (OCIS)>> The organic photoelectric elements according to Examples 1 to 5 and Comparative Examples 4 and 5 were arranged on the organic photoelectric element 100 of the image sensor 300 having the structure shown in FIG. 4 to manufacture an image sensor.

[0174] <Evaluation 1: Vapor deposition temperature of fullerene subunit derivatives> In order to evaluate the thermal stability of the fullerene subunit derivatives obtained in Synthesis Examples 1 to 5, the temperature at which 10% by weight of the derivatives sublimes at 10 Pa (Ts 10 , deposition temperature) and the temperature at which 50% by weight is sublimated at 10 Pa (Ts 50 , deposition temperature). For comparison, the deposition temperatures for the compounds of Comparative Synthesis Examples 1 to 5 are measured. All samples were used as high-purity powders refined to 99.9% or more and thoroughly dried, and the deposition temperature was measured by thermal gravimetric analysis (TGA). The measurement results of the compounds in Synthesis Examples 1 to 5, Comparative Synthesis Examples 1 to 3 and Comparative Synthesis Example 5 are shown in Table 1 below.

[0175] [Table 1] *Ts(℃)(-10wt%)(℃):The temperature at which the weight of the sample has decreased by 10wt% *Ts(℃)(-50wt%)(℃):The temperature at which the weight of the sample has decreased by 50wt%

[0176] Referring to Table 1, the fullerene subunit derivatives according to Synthesis Examples 1 to 5 exhibited lower deposition temperatures than the compounds according to Comparative Synthesis Examples 1 to 3 and Comparative Synthesis Example 5. From this, it was confirmed that the fullerene subunit derivatives of Synthesis Examples 1 to 5 are compounds that can be deposited by sublimation.

[0177] <Evaluation 2: Energy levels of fullerene subunit derivatives> After forming a thin film by vapor deposition of the fullerene subunit derivatives according to Synthesis Examples 1 to 5, the HOMO energy level and the LUMO energy level of each thin film are calculated using the "Gaussian 09 program" method in the "B3LYP / 6-31 G(d)level" theory described in "MJ Frisch, et al., Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT (2009)". Among these, the results of Synthesis Examples 1 to 5 and Comparative Synthesis Example 5 are shown in Table 2 below. For reference, the HOMO energy levels and LUMO energy levels of the compounds represented by the chemical formulas K and L, which are P-type semiconductor compounds, are also shown. [Table 2]

[0178] The structures of Chemical Formula K and Chemical Formula L shown in Table 2 are as follows: [ka] [ka]

[0179] Referring to Table 2, the compounds according to Synthesis Examples 1 to 5 were calculated by "B3LYP / 6-31 G(d)" with reference to "MJ Frisch, et al., Gaussian09, Revision D.01; Gaussian, Inc.: Wallingford, CT (2009)". As a result, it was confirmed that the HOMO is equivalent to that of C60 and the LUMO level is at a level for use as an N-type semiconductor. When the HOMO energy levels and LUMO energy levels of the P-type semiconductor compounds represented by the chemical formulas K and L are compared, it is found that they are suitable for use as N-type semiconductor compounds.

[0180] <Evaluation 3: Distance between N-type and P-type semiconductors> Using "Nanomatch software," the morphology of the active layer formed on the substrate when N-type and P-type semiconductors are co-deposited is evaluated. The average distance between the N-type semiconductor and the P-type semiconductor (compound of formula X) in the active layer was calculated and the results are shown in Table 3 below. The average distances were calculated from the “virtually formed blend morphology” created by the software, and the results are listed in Table 3. [Table 3]

[0181] The structures of Chemical Formulae M to Q shown in Table 3 are as follows. [ka] [ka] [ka] [ka] [ka]

[0182] Referring to Table 3, it was confirmed that the compounds represented by formulas A to E and MQ have a smaller distance from the P-type semiconductor than the compound represented by formula I, which does not have a bulky substituent on the side, by including a bulky substituent (X) and an additional bulky substituent on the side. This indicates that the crystallization of the compounds represented by chemical formulas A to E and MQ in the active layer is further reduced or suppressed compared to the compound represented by chemical formula I, and the compounds represented by chemical formulas A to E and MQ (N-type semiconductors) are well mixed with the P-type semiconductor to form the active layer. Therefore, it was found that the compounds represented by the chemical formulas A to E and MQ have a sufficiently low crystallinity themselves and exist in a state of being well mixed with the P-type semiconductor.

[0183] Evaluation 4: External quantum efficiency characteristics of the device The external quantum efficiency (EQE) of the organic photoelectric devices according to Examples 1 to 5 and Comparative Examples 4 and 5 is measured. The external quantum efficiency is measured using an IPCE measurement system (McScience, Korea). First, the equipment is calibrated using a Si photodiode (Hamamatsu, Japan), and then the organic photoelectric devices according to Examples 1 to 5 and Comparative Examples 4 and 5 are attached and measured in a wavelength range of about 350 nm to 750 nm. Among these, the results of Examples 1 to 5 and Comparative Examples 4 and 5 are shown in Table 4. [Table 4]

[0184] Referring to Table 4, the absorption in the blue region of the organic photoelectric devices according to Examples 1 to 5 was reduced by 30% to 50% or more compared to Comparative Example 5. The absorption of C60 in the blue region (450 nm) is known to be due to aggregation of C60 (Journal of Molecular Structure 526 (2000) 25-29). That is, the decrease in absorption in the blue region (450 nm) of the organic photoelectric elements according to Examples 1 to 5 indicates that the aggregation of C60 is reduced or eliminated. From this, it was confirmed that the organic photoelectric devices according to Examples 1 to 5 did not have abnormal light absorption characteristics in the blue region.

[0185] On the other hand, in Comparative Example 4, the EQE in the blue region decreased at room temperature before annealing as in Examples 1 to 5, but after annealing, the EQE performance decreased over the entire visible light region (Blue / Green / Red). Without being bound by any particular theory, it is believed that the reason why the EQE performance of the organic photovoltaic devices according to Examples 1 to 5 does not decrease even after annealing is that the fullerene subunit derivatives have three bulky substituents on the corannulene and therefore cannot be crystallized even at high temperatures. On the other hand, in the case of Comparative Example 4, in which the corannulene contains only one bulky substituent (X), it is believed that crystallization was promoted by annealing. This indicates that fullerene subunit derivatives with one bulky substituent have low thermal stability.

[0186] <Evaluation 5: Absorption coefficient in the blue region> The absorption coefficients of the organic photoelectric elements according to Examples 1 to 5 and Comparative Examples 4 and 5 in the blue region (450 nm) are measured. Among these, the measurement results of Examples 1 to 5 and Comparative Example 5 are shown in Table 5. [Table 5]

[0187] Referring to Table 5, it can be seen that the absorption in the blue region of the organic photoelectric devices according to Examples 1 to 5 was reduced by 25% or more compared to Comparative Example 5.

[0188] Rating 6: Mobility The mobility of the organic photoelectric elements according to Examples 1 to 5 and Comparative Examples 4 and 5 is measured. The mobility is measured by the “Space-charge-limited current (SCLC)” method described in the paper (Solar Energy Materials & Solar Cells 141 (2015) 87-92). Among these, the results of Examples 1 to 5 and Comparative Example 5 are shown in Table 6. [Table 6]

[0189] Referring to Table 6, it can be seen that the mobility of the organic photoelectric devices according to Examples 1 to 5 is 1.65 times higher than that of the organic photoelectric device according to Comparative Example 5. The partial aggregation(*) of C60, which is thought to exist within the “bulk hetero junction (BHJ)” of the active layer, was reduced or suppressed by the fullerene subunit derivative, and it is believed that the mobility was improved by suppressing the loss of charge at the aggregation site. In addition, since the fullerene subunit derivative has N-type properties, it is believed that it plays a role in charge transport, improving the mobility.

[0190] <Rating 7: YSNR10> For the image sensors of Examples 6 to 10 and Comparative Examples 6 and 7 including the organic photoelectric elements according to Examples 1 to 5 and Comparative Examples 4 and 5, YSNR10 is evaluated. The SNR10 was calculated when an 18% gray patch of a Macbeth chart was photographed under D-65 illumination. The photographing lens used was F2.8 with a transmittance of 80%, and a general interference lens was used as the infrared cut filter. The pixel size of the image sensor was 1.4 μm, and the frame rate was 15 fps. Here, YSNR10 is a value indicating the sensitivity of the image sensor, measured using the method in “Image Sensors and Image Quality in Mobile Phones” by Juha Alakarhu, published in the abstracts of the 2007 International Image Sensor Workshop (Ogunquit Maine, USA), and is the minimum illuminance in lux at which the signal-to-noise ratio becomes 10. The measurement results of the image sensors including the organic photoelectric elements of Example 1 and Comparative Example 5 are shown in Table 7. [Table 7]

[0191] Referring to Table 7, it can be seen that the YSNR10 of the image sensor including the organic photoelectric element according to Example 1 was improved by 10% compared to the image sensor including the organic photoelectric element of Comparative Example 5.

[0192] 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]

[0193] 100 Organic photoelectric element 10, 10a, 10b, 10c 1st electrode 20, 20a, 20b, 20c 2nd electrode 30, 30a, 30b, 30c organic layer 50a, 50b Light sensing element 55, 55a, 55b, 55c Charge reservoir 60 Lower insulation layer 65 Intermediate insulation layer 70 color filter layers 70a Blue filter 70b Red filter 80 Upper insulating layer 85 Through Hole 100a, 100b, 100c (1st to 3rd) organic photoelectric element 110 Semiconductor substrate 300, 400, 500 (organic CMOS) image sensor

Claims

1. 1. An N-type semiconductor composition comprising: A fullerene or a fullerene derivative, and represented by the following chemical formula 1: The N-type semiconductor composition, wherein Cy in Formula 1 has a fullerene subunit derivative selected from the moieties represented by Formula 2A below. 【Chemistry 1】 【Chemistry 2A】 (In the chemical formula 1 and the chemical formula 2A, Y 1 is NR c ; R c is a bulky substituent selected from a branched alkyl group having 3 to 7 carbon atoms and a substituted or unsubstituted aryl group having 6 carbon atoms; Z 1 and Z 2 are O; * = * is a moiety linked to Chemical Formula 1, X is Rc; R １ , R 3 to R 6 , and R ８ are each independently hydrogen; R 2 and R 7 are bulky substituents selected from a branched alkyl group having 4 carbon atoms, a branched alkoxy group having 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 carbon atoms.

2. The R ｃ the substituent of the branched alkyl group having 3 to 7 carbon atoms and the substituted aryl group having 6 carbon atoms is an isopropyl group; The R ２ and R ７ 2. The N-type semiconductor composition according to claim 1, wherein the branched alkoxy group having 4 carbon atoms is a t-butoxy group, and the substituent of the substituted aryl group having 6 carbon atoms is an isopropyl group or a t-butyl group.

3. An N-type semiconductor composition comprising a fullerene or a fullerene derivative, and a fullerene subunit derivative represented by any one of the following chemical formulas A to E. 【Chemistry A】 【Chemistry B】 【Chemical C】 【Chemistry D】 【Chemical E】

4. An N-type semiconductor composition, comprising: An N-type semiconductor composition comprising a fullerene or a fullerene derivative, and a fullerene subunit derivative represented by any one of the compounds represented by groups 1, 2, 4 and 5 below. 【comp-group1-1】 【comp-group1-2】 【comp-group1-3】 【comp-group2-1】 【comp-group2-2】 【comp-group2-3】 【comp-group4-1】 【comp-group4-2】 【comp-group4-3】 【comp-group5-1】 【comp-group5-2】 【comp-group5-3】

5. A thin film comprising the N-type semiconductor composition according to any one of claims 1 to 4.

6. 6. The thin film of claim 5, wherein the extinction coefficient of the thin film at a wavelength of 450 nm is less than the extinction coefficient of a thin film containing unsubstituted C60 fullerene at a wavelength of 450 nm.

7. An organic photoelectric device, a first electrode and a second electrode facing each other; an organic layer disposed between the first electrode and the second electrode; 5. An organic photoelectric device, wherein the organic layer comprises the N-type semiconductor composition according to claim 1.

8. the organic layer includes an active layer, the active layer including a P-type semiconductor and an N-type semiconductor forming a PN junction; The organic photoelectric device of claim 7, wherein the N-type semiconductor comprises the N-type semiconductor composition.

9. The organic photoelectric device according to claim 8, wherein the fullerene subunit derivative has an average distance from a P-type semiconductor of 6 Å or less.

10. An image sensor comprising the organic photoelectric element according to claim 7.

11. An electronic device comprising the organic photoelectric element according to claim 7.

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