N-type semiconductor compositions, and films, organic optoelectronic devices, image sensors, and electronic devices comprising the same

Abstract

Disclosed are N-type semiconductor compositions, and films, organic optoelectronic devices, image sensors, and electronic devices including the same, the N-type semiconductor compositions including: a fullerene or a fullerene derivative; and a fullerene subunit derivative represented by Chemical Formula 1. In Chemical Formula 1, X, Cy, and R 1 - R 8 are the same as defined in the detailed description.[Chemical Formula 1]

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2019-0057222, filed on May 15, 2019, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Examples of implementations provide N-type semiconductor compositions and films including the same, organic optoelectronic devices, image sensors, and electronic devices. Background Technology

[0004] Fullerenes are closed cage-like molecules made of carbon and are used in a variety of fields due to their stable structure and good electrical properties.

[0005] Organic optoelectronic devices are devices that convert light into electrical signals using the photoelectric effect. Organic optoelectronic devices include photodiodes and phototransistors, and can be applied to electronic devices such as image sensors. Organic optoelectronic devices may include fullerenes in an active layer that possess high light absorption properties and good electrical properties.

[0006] However, fullerenes can absorb light in the blue region and reduce the color clarity of organic optoelectronic devices in which fullerenes are applied.

[0007] Therefore, a method for controlling the absorption of the blue region of fullerenes may be needed. Summary of the Invention

[0008] Examples of implementations provide N-type semiconductor compositions capable of improving the color clarity of organic optoelectronic devices.

[0009] Example embodiments also provide organic optoelectronic devices comprising the N-type semiconductor composition.

[0010] Example implementations also provide image sensors and electronic devices that include the organic optoelectronic devices.

[0011] According to an example embodiment, the N-type semiconductor composition includes: a fullerene or a fullerene derivative; and a fullerene subunit derivative represented by chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In chemical formula 1,

[0015] Cy is a cyclic hydrocarbon group selected from C3-C20 alicyclic hydrocarbon groups and C6-C20 aromatic hydrocarbon groups, or a fused cyclic group of two or more cyclic hydrocarbon groups.

[0016] X is at least one bulky substituent selected from the following: substituted or unsubstituted C3-C30 branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0017] R 1 -R 8 Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0018] The condition is R 1 -R 8 At least one of them is a bulky substituent selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0019] In some embodiments, in chemical formula 1, R 1 -R 3 at least one and R 6 -R 8 At least one of them may be the same or different, and R 1 -R 3 at least one and R 6 -R 8 At least one of them may be a bulky substituent selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0020] In some embodiments, in chemical formula 1, R 1 -R3 At least one large-volume substituent and R 6 -R 8 At least one bulky substituent may exist symmetrically with respect to the axis of Cy.

[0021] In some embodiments, in chemical formula 1, R 1 and R 2 At least one of and R 7 and R 8 At least one of them may be the same or different, and may be a bulky substituent selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0022] In some embodiments, in chemical formula 1, R 2 and R 7 It can be a bulky substituent selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. And R 1 R 3 R 4 R 5 R 6 and R 8 It can be hydrogen, deuterium, halogen, cyano, C1-C20 straight-chain alkyl, or a combination thereof.

[0023] In some embodiments, in chemical formula 1, R 1 -R 3 Two adjacent substituents and R 6 -R 8 Two adjacent substituents can be linked together to provide C3-C20 alicyclic hydrocarbon groups.

[0024] In some embodiments, in chemical formula 1, R 2 and R 3 They can be connected to each other to provide C3-C20 alicyclic hydrocarbon groups, and R 6 and R 7They can be connected to each other to provide C3-C20 alicyclic hydrocarbon groups.

[0025] In some embodiments, the fullerene subunit derivative represented by Formula 1 may be a compound represented by Formula 1A.

[0026] [Chemical Formula 1A]

[0027]

[0028] In chemical formula 1A,

[0029] Cy can be a cyclic hydrocarbon group selected from C3-C20 alicyclic hydrocarbon groups and C6-C20 aromatic hydrocarbon groups, or a fused cyclic group of two or more cyclic hydrocarbon groups.

[0030] X may be at least one bulky substituent selected from the following: substituted or unsubstituted C3-C30 branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0031] R 1 R 2a R 4 R 5 R 6a and R 8 It may independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof, and

[0032] a1 and a2 can be independent integers from 1 to 4.

[0033] In some embodiments, the cyclic hydrocarbon group in Cy may be a heterocyclic group comprising at least one functional group selected from the following: -N=, -NR-, -O-, -S-, -Se-, -Te-, -C(=O)-, -C(=S)-, -C(=Se)-, -C(=Te)-, -C(=C(CN)2)-, and -C(=NR)-, wherein R may be a C1-C10 alkyl group.

[0034] In some embodiments, in Formula 1, Cy may be pyrrole, furan, pyrrolin, pyrrolidinone, cyclopentadiene, cyclopentanedione, pyrrolidinone, pyrrolidinone, pyrrolidinone including a ketone (C=O) group in the ring, pyridine, pyrimidine, indole, phthalimide, benzimidazole, benzothiazole, or a fused ring of these rings and a benzene ring.

[0035] In some embodiments, in chemical formula 1, Cy can be selected from the portion represented by chemical formulas 2A to 2C.

[0036] [Chemical Formula 2A]

[0037]

[0038] In chemical formula 2A,

[0039] Y 1 For CR a R b or NR c ,

[0040] R a and R b Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0041] The condition is R a and R b At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0042] R cThe substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0043] Z 1 and Z 2 For O, S, Se, Te, C(CN)2, or NR d , where R d It is a C1-C10 alkyl group or Y attached to the chemical formula 2A. 1 To provide fused rings, and

[0044] *=* is the part connecting to chemical formula 1.

[0045] [Chemical Formula 2B]

[0046]

[0047] In chemical formula 2B,

[0048] Y 2 For CR a R b NR c , O, S, Se, or Te,

[0049] Where R a R b and R c Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0050] R xIt can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0051] When Y 2 For CR a R b or NR c At that time, R a R b and R x At least one of and R c and R x At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0052] When Y 2 When R is O, S, Se, or Te x The bulk substituent is selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0053] *=* is the part connecting to chemical formula 1.

[0054] [Chemical formula 2C]

[0055]

[0056] In chemical formula 2C,

[0057] Y 2 For CR a R b NR c , O, S, Se, or Te,

[0058] Where R c It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0059] R x and R y It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0060] When Y 2 For CR a R b or NR c At that time, 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 following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0061] When Y 2 When R is O, S, Se, or Te x and R yAt least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0062] *=* is the part connecting to chemical formula 1.

[0063] In chemical formula 1, Cy can be selected from the parts represented by chemical formulas 3A to 3D.

[0064] [Chemical Formula 3A]

[0065]

[0066] In chemical formula 3A,

[0067] R x R y and R z Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0068] R x R y and R z At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0069] *=* is the part connecting to chemical formula 1.

[0070] [Chemical Formula 3B]

[0071]

[0072] In chemical formula 3B,

[0073] R x and R y Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0074] R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0075] *=* is the part connecting to chemical formula 1.

[0076] [Chemical formula 3C]

[0077]

[0078] In the chemical formula 3C,

[0079] R x and R y Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0080] R x and R yAt least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0081] *=* is the part connecting to chemical formula 1.

[0082] [Chemical Formula 3D]

[0083]

[0084] In chemical formula 3D,

[0085] R x and R y Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0086] R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0087] *=* is the part connecting to chemical formula 1.

[0088] In some embodiments, in chemical formula 1, Cy can be selected from the portion represented by chemical formulas 4A to 4C.

[0089] [Chemical Formula 4A]

[0090]

[0091] In chemical formula 4A,

[0092] Y 1 For CR a R b or NR c ,

[0093] R a and R b Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0094] The condition is R a and R b At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0095] R c The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0096] R p R q R r and R s Independently hydrogen, deuterium, or C1-C10 alkyl,

[0097] n is an integer between 0 and 2.

[0098] Z 1 and Z 2 For O, S, Se, Te, C(CN)2, or NR d , where R d It is a C1-C10 alkyl group or Y attached to chemical formula 4A1 To provide fused rings, and

[0099] *=* is the part connecting to chemical formula 1.

[0100] [Chemical Formula 4B]

[0101]

[0102] In chemical formula 4B,

[0103] Y 2 For CR a R b NR c , O, S, Se, or Te,

[0104] Where R a R b and R c Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0105] R x It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0106] When Y 2 For CR a R b or NR c At that time, R a R b and R x At least one of and R c and R xAt least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0107] When Y 2 When R is O, S, Se, or Te x The bulky substituent is selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof, and

[0108] R p R q R r and R s Independently hydrogen, deuterium, or C1-C10 alkyl,

[0109] n is an integer between 0 and 2, and

[0110] *=* is the part connecting to chemical formula 1.

[0111] [Chemical formula 4C]

[0112]

[0113] In the chemical formula 4C,

[0114] Y 2 For CR a R b NR c , O, S, Se, or Te,

[0115] Where R a R b and R cIndependently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0116] R x and R y It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0117] When Y 2 For CR a R b or NR c At that time, 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 following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0118] When Y 2 When R is O, S, Se, or Te x and R yAt least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0119] R p R q R r and R s Independently hydrogen, deuterium, or C1-C10 alkyl,

[0120] n is an integer between 0 and 2, and

[0121] *=* is the part connecting to chemical formula 1.

[0122] In some embodiments, in chemical formula 1, R 1 -R 8 At least one of them can be a group represented by chemical formula 5A:

[0123] [Chemical Formula 5A]

[0124]

[0125] In chemical formula 5A,

[0126] R a and R b It can be hydrogen, halogen, cyano, or C1-C6 alkyl.

[0127] n1 is an integer between 0 and 10, and

[0128] R 11 -R 13 It is hydrogen, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl, provided that R 11 -R 13 At least two of them are C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl.

[0129] In some implementations, R 1 -R 8 At least one of them can be a group represented by the chemical formula 5B.

[0130] [Chemical Formula 5B]

[0131]

[0132] In chemical formula 5B,

[0133] R c and R d It can be hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C2-C10 ether, or C2-C10 ester.

[0134] n² is an integer between 2 and 10.

[0135] -C(R c R d - is replaced by functional groups selected from the following: -O-, -S-, -S(=O)-, -S(=O)2-, -C(=O)-, -C(=O)O-, -OC(=O)-, and combinations thereof.

[0136] R 21 -R 23 It is hydrogen, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl, provided that R 21 -R 23 At least two of them are C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl.

[0137] In some embodiments, in chemical formula 1, R 1 -R 8 At least one of them can be a group represented by the chemical formula 5C.

[0138] [Chemical formula 5C]

[0139]

[0140] In the chemical formula 5C,

[0141] R e and R f It can be hydrogen, halogen, cyano, or C1-C6 alkyl.

[0142] n3 is an integer between 0 and 10, and

[0143] R 31 -R 33 It is hydrogen, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, or C1-C10 alkylsilyl, provided that R 31 -R 33 At least two of them are C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl.

[0144] In some embodiments, in chemical formula 1, R 1 -R 8 At least one of the following can independently be isopropyl, 1-methylpropyl, isobutyl, 1-methylbutyl, 1-ethylbutyl, 1-propylbutyl, isopentyl, 1-methylpentyl, 1-ethylpentyl, 1-propylpentyl, 2-methylpentyl, 2-ethylpentyl, 2-propylpentyl, 3-methylpentyl, 3-ethylpentyl, 3-propylpentyl, isohexyl, 1-methylhexyl, 1-ethylhexyl, 1-propylhexyl, 2-methylhexyl, 2-ethylhexyl, 2-propylhexyl, 3-methylhexyl, 3-ethylhexyl, 3-propylhexyl, 3-propyl Hexyl, isoheptyl, 1-methylheptyl, 1-ethylheptyl, 1-propylheptyl, 2-methylheptyl, 2-ethylheptyl, 2-propylheptyl, 3-methylheptyl, 3-ethylheptyl, 3-propylheptyl, isooctyl, 1-methyloctyl, 1-ethyloctyl, 1-propyloctyl, 2-methyloctyl, 2-ethyloctyl, 2-propyloctyl, 3-methyloctyl, 3-ethyloctyl, 3-propyloctyl, 1-methylnonyl, 1,1-dimethylnonyl, tert-butyl, tert-pentyl, tert-hexyl, neopentyl, or neohexyl.

[0145] In some embodiments, the fullerene subunit derivative may have a distance from the p-type semiconductor of less than or equal to approximately The average distance.

[0146] According to another embodiment, a thin film comprising the N-type semiconductor composition is provided.

[0147] In some embodiments, the absorption coefficient of the film at a wavelength of about 450 nm may be less than that of a film comprising unsubstituted C60 fullerene at a wavelength of about 450 nm.

[0148] Another embodiment provides an organic optoelectronic device comprising: a first electrode and a second electrode facing each other, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises the N-type semiconductor composition.

[0149] In some embodiments, the organic layer may include an active layer, and the active layer may include a P-type semiconductor and an N-type semiconductor forming a pn junction, and the N-type semiconductor may include the N-type semiconductor composition.

[0150] According to another embodiment, an image sensor including the organic optoelectronic device is provided.

[0151] According to another embodiment, an electronic device including the organic optoelectronic device is provided.

[0152] According to an example embodiment, the N-type semiconductor composition includes: a fullerene or a fullerene derivative; and a fullerene subunit derivative represented by chemical formula 1.

[0153] [Chemical Formula 1]

[0154]

[0155] In chemical formula 1,

[0156] Cy includes C3-C20 alicyclic hydrocarbon groups, C6-C20 aromatic hydrocarbon groups, or fused cyclic groups of two or more cyclic hydrocarbon groups.

[0157] X includes substituted or unsubstituted C3-C30 branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C3-C30 heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups, and

[0158] R 1 -R 8 Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0159] The condition is R 1 -R 8 At least one of them includes substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0160] In some embodiments, the fullerene or fullerene derivative may be a fullerene.

[0161] In some embodiments, the fullerene or fullerene derivative may be a fullerene derivative.

[0162] In some embodiments, the organic optoelectronic device may include: a first electrode and a second electrode facing each other, and an organic layer between the first electrode and the second electrode. The organic layer may include the N-type semiconductor composition.

[0163] In some implementations, the image sensor may include an organic optoelectronic device.

[0164] The N-type semiconductor composition can improve the color clarity of the organic optoelectronic device by reducing the absorption of the blue region of the fullerene or fullerene derivative. Attached Figure Description

[0165] Figure 1 A cross-sectional view illustrating an organic optoelectronic device according to one embodiment is provided.

[0166] Figure 2 A cross-sectional view is provided to illustrate an organic optoelectronic device according to another embodiment.

[0167] Figure 3 For illustrative purposes, a plan view of a CMOS image sensor according to one embodiment is shown.

[0168] Figure 4 To explain Figure 3 A cross-sectional view of an example of a CMOS image sensor.

[0169] Figure 5 To show a cross-sectional view of another example of a CMOS image sensor,

[0170] Figure 6 To show a cross-sectional view of another example of a CMOS image sensor,

[0171] Figure 7 For illustrative purposes, a plan view of a CMOS image sensor according to another embodiment is shown.

[0172] Figure 8 A cross-sectional view of a CMOS image sensor according to another embodiment, and

[0173] Figure 9 This is a block diagram of a digital camera including an image sensor according to an embodiment. Detailed Implementation

[0174] Hereinafter, exemplary embodiments of the present disclosure will be described in detail so that those skilled in the art will understand them. However, the present disclosure may be embodied in many different forms and is not to be construed as limited to the exemplary embodiments set forth herein.

[0175] In the accompanying drawings, the thicknesses of layers, films, panels, regions, etc., are enlarged for clarity. The same reference numerals denote the same elements throughout the specification. It will be understood that when an element, such as a layer, film, region, or substrate, is referred to as being "on" another element, it may be directly on said other element or there may be intermediate elements present. Conversely, when an element is referred to as being "directly on" another element, there are no intermediate elements.

[0176] In the accompanying drawings, for clarity of implementation, parts unrelated to the description have been omitted, and the same or similar constituent elements are indicated by the same reference numerals throughout the specification.

[0177] As used herein, “combination” includes mixtures of two or more types, intersubstitution, and stacked structures of two or more types.

[0178] As used herein, unless otherwise specifically defined, “substituted” means that a compound, functional group, or part of the hydrogen atom is replaced by: a halogen atom (-F, -Cl, -Br, or -I), a hydroxyl group, a nitro group, a cyano group, an amino group, an azide group, an amido group, a hydrazine group, a hydrazone 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, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C30 aryl group, a C7-C30 aralkyl group, a C1-C20 alkoxy group, a C3-C20 heteroaryl group, a C3-C30 cycloalkyl group, a C3-C15 cycloalkenyl group, a C6-C15 cycloalkynyl group, a C3-C30 heterocycloalkyl group, or a combination thereof (e.g., a C1-C20 haloalkyl group, such as a C1-C20 trifluoroalkyl group).

[0179] As used herein, unless otherwise defined, “heterogeneous” means one to three heteroatoms selected from N, O, S, P, and Si, plus the remaining carbon, in a compound, functional group, or part thereof.

[0180] As used herein, unless otherwise defined, “aryl” means a group comprising: at least one aromatic hydrocarbon moiety, for example, all elements of the aromatic hydrocarbon moiety having conjugated p-orbitals, such as phenyl or naphthyl; two or more aromatic hydrocarbon moiety moiety connected by σ bonds, such as biphenyl, terphenyl, or tetraphenyl; and two or more aromatic hydrocarbon moiety moiety moiety, such as fluorenyl, directly or indirectly fused to provide a non-aromatic fused ring.

[0181] As used herein, unless otherwise defined, a “heterocyclic group” is a hypernym of a C2-C30 (e.g., C2-C20) heteroaryl, a C2-C30 (e.g., C2-C20) heterocyclic alkyl, or a fused cyclic group thereof, and may include at least one (e.g., 1-3) heteroatoms replacing carbon (C) in the ring, such as an aryl, cycloalkyl, its fused cyclic group, or a combination thereof, wherein the heteroatoms may be, for example, N, O, S, P, Se, Te, and / or Si, but are not limited thereto. When the heterocyclic group is a fused cyclic group, at least one (e.g., 1-3) heteroatoms may be included in the entire ring or in each ring of the heterocyclic group.

[0182] As used herein, unless otherwise defined, "heteroaryl" refers to an aryl group comprising at least one heteroatom, which may be, for example, N, O, S, P, Se, Te, and / or Si, but is not limited thereto. At least two heteroaryl groups may be directly linked by a σ bond, or at least two heterocyclic groups may be fused together. When the heteroaryl group is a fused ring, each ring may comprise one to three heteroatoms.

[0183] As used herein, unless otherwise defined, “heteroalkyl” means an alkyl group that includes at least one heteroatom in the main chain of an alkyl group, and may in particular be an alkyl group in which at least one methylene group is replaced by -O-, -S-, -C(=O)-, -C(=S)-, -OC(=O)-, and -C(=O)O-.

[0184] As used herein, unless otherwise defined, "cyclic hydrocarbon group" means a C3-C20 alicyclic hydrocarbon group, a C6-C20 aromatic hydrocarbon group, a fused cyclic group of two or more cyclic hydrocarbon groups, or a heterocyclic group that includes heteroatoms.

[0185] As used herein, unless otherwise defined, "alicyclic hydrocarbon group" means at least one non-aromatic ring (alicyclic ring) or a fused ring wherein such non-aromatic rings are fused together, selected from C3-C30 cycloalkyl, such as C3-C20 cycloalkyl or C3-C10 cycloalkyl; C3-C30 cycloalkenyl, such as C3-C20 cycloalkenyl or C3-C10 cycloalkenyl; and C2-C30 heterocyclic alkyl, such as C2-C20 heterocyclic alkyl or C3-C10 heterocyclic alkyl.

[0186] As used herein, unless otherwise defined, an "aromatic group" may include at least one aromatic ring (aromatic ring) or its fused ring, such as a C6-C30 aryl, such as a C6-C20 aryl or a C6-C10 aryl.

[0187] As used herein, unless otherwise defined, “volume substituent” means a substituted or unsubstituted branched alkyl, a substituted or unsubstituted branched alkoxy, a substituted or unsubstituted branched alkylsilyl, a substituted or unsubstituted branched heteroalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted heterocycloalkyl, or a combination thereof. In some embodiments, "volume substituent" refers to substituted or unsubstituted C3-C20 (e.g., C4-C20) branched alkyl, substituted or unsubstituted C3-C20 (e.g., C4-C20) branched alkoxy, substituted or unsubstituted C3-C20 (e.g., C4-C20) branched alkylsilyl, substituted or unsubstituted C3-C20 (e.g., C4-C20) branched heteroalkyl, substituted or unsubstituted C6-C30 (e.g., C6-C20) aryl, substituted or unsubstituted C2-C30 (e.g., C3-C20) heteroaryl, substituted or unsubstituted C3-C30 (e.g., C4-C20) cycloalkyl, substituted or unsubstituted C3-C30 (e.g., C4-C20) heteroalkyl, and combinations thereof.

[0188] The expression "at least one of..." modifies the entire list of elements (e.g., A, B, and C) but does not modify any individual elements of the list when it precedes or follows the list of elements. For example, "at least one of A, B, and C", "at least one of A, B, or C", "A, B, C, or any combination thereof", and "A, B, C, or any combination thereof" can be interpreted as covering any of the following combinations: A; B; A and B; A and C; B and C; and A, B, and C.

[0189] The following describes an N-type semiconductor composition according to an embodiment.

[0190] According to an embodiment, the N-type semiconductor composition includes: fullerene or fullerene derivative; and fullerene subunit derivative represented by chemical formula 1.

[0191] [Chemical Formula 1]

[0192]

[0193] In chemical formula 1,

[0194] Cy is a cyclic hydrocarbon group selected from C3-C20 alicyclic hydrocarbon groups and C6-C20 aromatic hydrocarbon groups, or a fused cyclic group of two or more cyclic hydrocarbon groups.

[0195] X is at least one bulky substituent selected from the following: substituted or unsubstituted C3-C30 branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, and

[0196] R 1 -R 8 Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof, provided that R 1 -R 8 At least one of them is a bulky substituent selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0197] The fullerene subunit derivative of Formula 1 includes a cyclic hydrocarbon group (Cy) having at least one bulky substituent (X), and at positions other than Cy (R). 1 -R 8 The fullerene subunit derivative further comprises at least one bulky substituent at at least one location, thereby effectively suppressing the crystallinity (crystallinity) of the fullerene subunit derivative. The fullerene subunit derivative of Formula 1 can interact with the fullerene or fullerene derivative, thereby effectively suppressing the aggregation of the fullerene or fullerene derivative. By suppressing the aggregation of the fullerene or fullerene derivative, light absorption in the blue region (approximately 400 nm to approximately 500 nm) can be significantly reduced, thereby improving the color clarity of the device.

[0198] The bulky substituent (X) can effectively control the steric hindrance between the fullerene subunit derivatives to maintain a constant spacing. 1 -R 8 At least one bulky substituent can reduce the crystallinity of the fullerene subunit derivative and can be well mixed with the P-type and N-type semiconductors (fullerenes or fullerene derivatives) in the active layer. Additionally, R1 -R 8 At least one large-volume substituent can suppress the aggregation of the fullerene or fullerene derivative by allowing the cardiocycloene skeleton of the derivative to well surround the fullerene or fullerene derivative. Additionally, R 1 -R 8 At least one large-volume substituent can improve the thermal stability of the fullerene subunit derivative, which can improve high-temperature properties when applied to devices.

[0199] The fullerene subunit derivative of Formula 1 has a structure that can suppress the aggregation of the fullerene or fullerene derivative, but does not extend the conjugated structure of the cardiocycloene, thereby suppressing the increase in crystallinity and making it advantageous to perform sublimation purification during film formation.

[0200] The cyclic hydrocarbon group may include one or more heteroatoms in the ring. Specifically, the cyclic hydrocarbon group may be a heterocyclic group comprising at least one functional group selected from the following: -N=, -NR-, -O-, -S-, -Se-, -Te-, -C(=O)-, -C(=S)-, -C(=Se)-, -C(=Te)-, -C(=C(CN)2)-, and -C(=NR)-, where R is a C1-C10 alkyl group. Thus, when Cy is a heterocyclic group, the N-type properties of the fullerene subunit derivative can be further enhanced.

[0201] The HOMO / LUMO level of the fullerene subunit derivative can be adjusted by a combination of the cyclic hydrocarbon group and a bulk substituent (X) therein. For example, when Cy is a hydrocarbon group that does not include an electron-withdrawing functional group (e.g., -C(=O)-, -N=, -NR-, etc.), an electron-withdrawing functional group can be introduced into the bulk substituent (X). Examples of bulk substituents (X) having an electron-withdrawing functional group include: N-containing cyclic groups such as pyrrole, pyridyl, pyrimidinyl, triazine, etc.; or C6-C20 aryl groups substituted with fluorine (F) groups, cyano (CN) groups, C1-C10 carboxyl or ester groups (e.g., acetate groups) or C1-C10 trifluoroalkyl (e.g., trifluoromethyl (CF3)).

[0202] R 1 -R 8At least two, such as three or four, may be bulk substituents selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0203] In chemical formula 1, R 1 -R 3 at least one and R 6 -R 8 At least one of them may be the same or different. And may be a bulky substituent selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0204] R 1 -R 3 At least one large-volume substituent and R 6 -R 8 At least one large-volume substituent may exist at a position symmetrical to Cy.

[0205] In chemical formula 1, R 1 -R 8 At least two of them may be bulk substituents selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0206] In Formula 1, when two or more bulky substituents are included at positions symmetrical to Cy, the fullerene subunit derivative can effectively cover the fullerene or fullerene derivative, thereby inhibiting their aggregation.

[0207] The fullerene may be a C60-C120 fullerene, and particularly may be C60, C70, C74, C76, C78, ​​C80, C82, C84, C90, or C96, but is not limited thereto.

[0208] The fullerene derivative refers to a compound having substituents on a fullerene. Examples of substituents may be alkyl, aryl, or heterocyclic groups. The alkyl group may be C1-C12 alkyl, such as C1-C5 alkyl. The aryl group may be phenyl, naphthyl, or anthracene. Here, the heterocyclic group may be furanyl, thiophene, pyrroleyl, etc. Azolyl, pyridyl, quinolinyl, or carbazole.

[0209] Specific examples of the fullerene derivatives may include, but are not limited to, methyl phenyl-C61-butyrate (PCBM, [6,6]-phenyl-C61-butyrate), ICBA (indene-C60 diadduct), and ICMA (indene-C60 monoadduct).

[0210] In chemical formula 1, R 1 -R 3 at least one and R 6 -R 8 At least one of the following may be the same or different, and may be a bulky substituent selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. In this case, steric hindrance can be effectively controlled to suppress the aggregation of fullerenes or fullerene derivatives during deposition.

[0211] In chemical formula 1, R 1 and R 2 At least one of and R 7 and R 8 At least one of them may be the same or different, and may be a bulky substituent selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof, and R 3 R 4 R 5 and R6 It can be hydrogen, deuterium, halogen, cyano, C1-C20 straight-chain alkyl, or a combination thereof. In this case, steric hindrance can be effectively controlled to suppress the aggregation of fullerenes or fullerene derivatives during deposition.

[0212] In chemical formula 1, R 2 and R 7 It may be a bulky substituent selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof, and R 1 R 3 R 4 R 5 R 6 and R 8 It can be hydrogen, deuterium, halogen, cyano, C1-C20 straight-chain alkyl, or a combination thereof. In this case, by having large-volume substituents on both sides relative to Cy, steric hindrance can be effectively controlled to suppress the aggregation of fullerenes or fullerene derivatives during deposition.

[0213] According to the implementation method, in chemical formula 1, R 1 -R 3 Two adjacent substituents and R 6 -R 8 Two adjacent substituents can connect with each other to form a C3-C20 alicyclic hydrocarbon group. Such a C3-C20 alicyclic hydrocarbon group can inhibit the expansion of the conjugated structure of the cardiocycloene to suppress the increase in crystallinity. The C3-C20 alicyclic hydrocarbon group can be fused with a C6-C20 aromatic hydrocarbon group.

[0214] In chemical formula 1, R 2 and R 3 They can connect with each other to form C3-C20 alicyclic hydrocarbon groups, and R 6 and R 7 They can be linked together to form C3-C20 alicyclic hydrocarbon groups. The C3-C20 alicyclic hydrocarbon groups can be fused with C6-C20 aromatic hydrocarbon groups. The C3-C20 alicyclic hydrocarbon groups can be pentagonal rings, and the structure in which the pentagonal ring can be fused with a benzene ring is represented by chemical formula 1A.

[0215] [Chemical Formula 1A]

[0216]

[0217] In chemical formula 1A,

[0218] Cy is a cyclic hydrocarbon group selected from C3-C20 alicyclic hydrocarbon groups and C6-C20 aromatic hydrocarbon groups, or a fused cyclic group of two or more cyclic hydrocarbon groups.

[0219] X is at least one bulky substituent selected from the following: substituted or unsubstituted C3-C30 branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0220] R 1 R 2a R 4 R 5 R 6a and R 8 Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof, and

[0221] a1 and a2 are independent integers from 1 to 4.

[0222] In chemical formula 1, Cy can be pyrrole, furan, pyrrolin, pyrrolidinone, cyclopentadiene, cyclopentadione, pyrrolidinazole, pyrrolidinazole including a ketone (C═O) group in the ring, pyridine, pyrimidine, indole, pyridine, phthalimide, benzimidazole, benzothiazole, or a fused ring of these and a benzene ring.

[0223] In chemical formula 1, Cy can be the part represented by chemical formula 2A.

[0224] [Chemical Formula 2A]

[0225]

[0226] In chemical formula 2A,

[0227] Y 1 For CR a R b or NR c ,

[0228] R a and R bIndependently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof, provided that R a and R b At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0229] R c The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0230] Z 1 and Z 2 For O, S, Se, Te, C(CN)2, or NR d , where R d It is a C1-C10 alkyl group or Y attached to the chemical formula 2A. 1 To provide fused rings, and

[0231] *=* is the part connecting to chemical formula 1.

[0232] For example, the part represented by chemical formula 2A can be the part represented by chemical formula 2A-1.

[0233] [Chemical Formula 2A-1]

[0234]

[0235] In chemical formula 2A-1,

[0236] R a and R bIndependently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof, provided that R a and R b At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0237] R c The bulk substituent is selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0238] *=* is the part connecting to chemical formula 1.

[0239] When Z 2 For NR d And R d Connected to Y in chemical formula 2A 1 When a fused ring is formed, chemical formula 2A can be the part represented by chemical formula 2A-2.

[0240] [Chemical Formula 2A-2]

[0241]

[0242] In chemical formula 2A-2,

[0243] Y 1 For CR a Or N,

[0244] Z 1 For O, S, Se, Te, C(CN)2, or NR d ,and

[0245] Ar is a C6-C30 aryl or C3-C30 heteroaryl.

[0246] In chemical formula 1, Cy can be the part represented by chemical formula 2B.

[0247] [Chemical Formula 2B]

[0248]

[0249] In chemical formula 2B,

[0250] Y 2 For CR a R b NR c , O, S, Se, or Te,

[0251] Where R a R b and R c Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0252] R x It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0253] When Y 2 For CR a R b or NR c At that time, R a R b and R x At least one of and R c and R xAt least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0254] When Y 2 When R is O, S, Se, or Te x The bulk substituent is selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0255] *=* is the part connecting to chemical formula 1.

[0256] For example, the part represented by chemical formula 2B can be the part represented by chemical formula 2B-1.

[0257] [Chemical Formula 2B-1]

[0258]

[0259] In chemical formula 2B-1,

[0260] R a R b and R c Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0261] R xIt can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0262] R a R b and R x At least one of and R c and R x At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0263] *=* is the part connecting to chemical formula 1.

[0264] For example, the portion represented by chemical formula 2B may be selected from the portion represented by chemical formula 2B-2.

[0265] [Chemical Formula 2B-2]

[0266]

[0267] In chemical formula 2B-2,

[0268] R x The bulk substituent is selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0269] *=* is the part connecting to chemical formula 1.

[0270] In chemical formula 1, Cy can be the part represented by chemical formula 2C.

[0271] [Chemical formula 2C]

[0272]

[0273] In chemical formula 2C,

[0274] Y 2 For CR a R b NR c , O, S, Se, or Te,

[0275] Where R c It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0276] R x and R y It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0277] When Y 2 For CR a R b or NR c At that time, 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 following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0278] When Y2 When R is O, S, Se, or Te x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0279] *=* is the part connecting to chemical formula 1.

[0280] For example, the part represented by chemical formula 2C can be the part represented by chemical formula 2C-1.

[0281] [Chemical formula 2C-1]

[0282]

[0283] In chemical formula 2C-1,

[0284] R c It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0285] R x and R y It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0286] R c R x and R yAt least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0287] *=* is the part connecting to chemical formula 1.

[0288] For example, the part represented by chemical formula 2C can be the part represented by chemical formula 2C-2.

[0289] [Chemical formula 2C-2]

[0290]

[0291] In the chemical formula 2C-2,

[0292] R x and R y It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0293] R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0294] *=* is the part connecting to chemical formula 1.

[0295] In chemical formula 1, Cy can be selected from the parts represented by chemical formulas 3A to 3D.

[0296] [Chemical Formula 3A]

[0297]

[0298] In chemical formula 3A,

[0299] R x R y and R z Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0300] R x R y and R z At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0301] *=* is the part connecting to chemical formula 1.

[0302] [Chemical Formula 3B]

[0303]

[0304] In chemical formula 3B,

[0305] R x and R y Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0306] R x and R yAt least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0307] *=* is the part connecting to chemical formula 1.

[0308] [Chemical formula 3C]

[0309]

[0310] In the chemical formula 3C,

[0311] R x and R y Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0312] R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0313] *=* is the part connecting to chemical formula 1.

[0314] [Chemical Formula 3D]

[0315]

[0316] In chemical formula 3D,

[0317] R x and R yIndependently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0318] R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0319] *=* is the part connecting to chemical formula 1.

[0320] In chemical formula 1, Cy can be the part represented by chemical formula 4A.

[0321] [Chemical Formula 4A]

[0322]

[0323] In chemical formula 4A,

[0324] Y 1 For CR a R b or NR c ,

[0325] R a and R b Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof, provided that R a and R bAt least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0326] R c The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0327] R p R q R r and R s Independently hydrogen, deuterium, or C1-C10 alkyl,

[0328] n is an integer between 0 and 2.

[0329] Z 1 and Z 2 For O, S, Se, Te, C(CN)2, or NR d , where R d It is a C1-C10 alkyl group or Y attached to chemical formula 4A 1 To provide fused rings, and

[0330] *=* is the part connecting to chemical formula 1.

[0331] For example, the portion represented by chemical formula 4A can be the portion represented by chemical formula 4A-1. Chemical formula 4A-1 describes the case where n of chemical formula 4A is 0, but compounds in which n of chemical formula 4A is 1 or 2 can be represented in the same way as in chemical formula 4A-1.

[0332] [Chemical Formula 4A-1]

[0333]

[0334] In chemical formula 4A-1,

[0335] R a and R bIndependently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof, provided that R a and R b At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0336] R c The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0337] R p and R q Independently hydrogen, deuterium, or C1-C10 alkyl, and

[0338] *=* is the part connecting to chemical formula 1.

[0339] In chemical formula 1, Cy can be represented by chemical formula 4B.

[0340] [Chemical Formula 4B]

[0341]

[0342] In chemical formula 4B,

[0343] Y 2 For CR a R b NR c , O, S, Se, or Te,

[0344] Where R a Rb and R c Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0345] R x It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0346] When Y 2 For CR a R b or NR c At that time, R a R b and R x At least one of and R c and R x At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0347] When Y 2 When R is O, S, Se, or Te x The bulky substituent is selected from the following: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof, and

[0348] R p R q R r and R s Independently hydrogen, deuterium, or C1-C10 alkyl,

[0349] n is an integer between 0 and 2, and

[0350] *=* is the part connecting to chemical formula 1.

[0351] For example, the portion represented by chemical formula 4B can be the portion represented by chemical formula 4B-1. Chemical formula 4B-1 describes the case where n of chemical formula 4B is 0, but compounds in which n of chemical formula 4B is 1 or 2 can be represented in the same way as in chemical formula 4B-1.

[0352] [Chemical Formula 4B-1]

[0353]

[0354] In chemical formula 4B-1,

[0355] R a and R b Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0356] R x It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0357] R a R b and R x At least one of and R c and R xAt least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0358] R p and R q Independently hydrogen, deuterium, or C1-C10 alkyl, and

[0359] *=* is the part connecting to chemical formula 1.

[0360] For example, the portion represented by chemical formula 4B can be the portion represented by chemical formula 4B-2. Chemical formula 4B-2 describes the case where n of chemical formula 4B is 0, but compounds in which n of chemical formula 4B is 1 or 2 can be represented in the same way as in chemical formula 4B-2.

[0361] [Chemical Formula 4B-2]

[0362]

[0363] In chemical formula 4B-2,

[0364] R x The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0365] R p and R q Independently hydrogen, deuterium, or C1-C10 alkyl, and

[0366] *=* is the part connecting to chemical formula 1.

[0367] In chemical formula 1, Cy can be selected from the part represented by chemical formula 4C.

[0368] [Chemical formula 4C]

[0369]

[0370] In the chemical formula 4C,

[0371] Y 2 For CR a R b NR c , O, S, Se, or Te,

[0372] Where R a R b and R c Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof.

[0373] R x and R y It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0374] When Y 2 For CR a R b or NR c At that time, 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 following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0375] When Y 2 When R is O, S, Se, or Tex and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0376] R p R q R r and R s Independently hydrogen, deuterium, or C1-C10 alkyl,

[0377] n is an integer between 0 and 2, and

[0378] *=* is the part connecting to chemical formula 1.

[0379] For example, the portion represented by chemical formula 4C can be the portion represented by chemical formula 4C-1. Chemical formula 4C-1 indicates the case where n of chemical formula 4C is 0, but compounds in which n of chemical formula 4C is 1 or 2 can be represented in the same way as in chemical formula 4C-1.

[0380] [Chemical formula 4C-1]

[0381]

[0382] In chemical formula 4C-1,

[0383] R c It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0384] R x and R yIt can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0385] R c R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0386] R p and R q Independently hydrogen, deuterium, or C1-C10 alkyl, and

[0387] *=* is the part connecting to chemical formula 1.

[0388] For example, the portion represented by chemical formula 4C can be the portion represented by chemical formula 4C-2. Chemical formula 4C-2 indicates the case where n of chemical formula 4C is 0, but compounds in which n of chemical formula 4C is 1 or 2 can be represented in the same way as in chemical formula 4C-2.

[0389] [Chemical formula 4C-2]

[0390]

[0391] In the chemical formula 4C⁻²,

[0392] R x and R y It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof.

[0393] R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof.

[0394] R p and R q Independently hydrogen, deuterium, or C1-C10 alkyl, and

[0395] *=* is the part connecting to chemical formula 1.

[0396] In embodiments, substituted or unsubstituted C3-C20 branched alkyl groups and substituted or unsubstituted C3-C20 branched alkoxy groups may be represented by chemical formula 5A.

[0397] [Chemical Formula 5A]

[0398]

[0399] In chemical formula 5A,

[0400] R a and R b It can be hydrogen, halogen, cyano, or C1-C6 alkyl.

[0401] n1 is an integer between 0 and 10, and

[0402] R 11 -R 13 It is hydrogen, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, or C1-C10 alkylsilyl, provided that R 11 -R 13 At least two of them are C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl.

[0403] In embodiments, the C3-C20 branched alkyl group may be isopropyl, 1-methylpropyl, isobutyl, 1-methylbutyl, 1-ethylbutyl, 1-propylbutyl, isopentyl, 1-methylpentyl, 1-ethylpentyl, 1-propylpentyl, 2-methylpentyl, 2-ethylpentyl, 2-propylpentyl, 3-methylpentyl, 3-ethylpentyl, 3-propylpentyl, isohexyl, 1-methylhexyl, 1-ethylhexyl, 1-propylhexyl, 2-methylhexyl, 2-ethylhexyl, 2-propylhexyl, 3-methylhexyl, 3-ethylhexyl, 3 -propylhexyl, isoheptyl, 1-methylheptyl, 1-ethylheptyl, 1-propylheptyl, 2-methylheptyl, 2-ethylheptyl, 2-propylheptyl, 3-methylheptyl, 3-ethylheptyl, 3-propylheptyl, isooctyl, 1-methyloctyl, 1-ethyloctyl, 1-propyloctyl, 2-methyloctyl, 2-ethyloctyl, 2-propyloctyl, 3-methyloctyl, 3-ethyloctyl, 3-propyloctyl, 1-methylnonyl, 1,1-dimethylnonyl, tert-butyl, tert-pentyl, tert-hexyl, neopentyl, or neohexyl, but not limited to these.

[0404] In embodiments, the C3-C20 branched heteroalkyl group may be wherein -C(R) c R d A group that is replaced by a functional group selected from -O-, -S-, -S(=O)-, -S(=O)2-, -C(=O)-, -C(=O)O-, -OC(=O)-, or a combination thereof and can be represented by the chemical formula 5B.

[0405] [Chemical Formula 5B]

[0406]

[0407] In chemical formula 5B,

[0408] R c and R d It can be hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C2-C10 ether, or C2-C10 ester.

[0409] n² is an integer between 2 and 10, and

[0410] R 21 -R 23 It is hydrogen, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl, provided that R 21 -R 23 At least two of them are C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl.

[0411] In embodiments, substituted or unsubstituted C3-C20 branched alkylsilyl groups may be represented by the chemical formula 5C.

[0412] [Chemical formula 5C]

[0413]

[0414] In the chemical formula 5C,

[0415] R e and R f It can be hydrogen, halogen, cyano, or C1-C6 alkyl.

[0416] n3 is an integer between 0 and 10, and

[0417] R 31 -R 33 It is hydrogen, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, or C1-C10 alkylsilyl, provided that R 31 -R 33 At least two of them are C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl.

[0418] Specific examples of the fullerene subunit derivatives include compounds from groups 1 to 8.

[0419] [Group 1]

[0420]

[0421]

[0422]

[0423]

[0424] Branched alkyl groups, such as isopropyl (iPr), tert-butyl (tBu), 2-methylpropyl, and trimethylsilyl (TMS), can replace two substituents (O) of the cardiocycloene in group 1. t The Bu group is substituted. Group 2 illustrates substitution by the tert-butyl group. t The Bu group replaces two substituents (O) of the cyclohexene in group 1. t Group 3 describes the structure substituted with the Bu group and the structure substituted with the trimethylsilyl (TMS) group.

[0425] [Group 2]

[0426]

[0427]

[0428]

[0429] [Group 3]

[0430]

[0431]

[0432]

[0433] Group 4 explains the two substituents (O) of the cycloene in Group 1 that are replaced by phenyl groups. t The structure is formed by substituting the Bu group.

[0434] [Group 4]

[0435]

[0436]

[0437]

[0438] In group 4, the two phenyl (Ph) groups that are substituents of the cardiocycloene are substituted by at least one substituent selected from: C1-C20 straight-chain alkyl, C3-C20 branched alkyl, C6-C12 aryl, and C3-C12 heteroaryl. Multiple substituents may be present, and in this case, they may be the same as or different from each other. The substituents may be located at ortho, meta, or para positions. For example, a structure substituted at the ortho position with isopropyl or tert-butyl is shown in group 5.

[0439] [Group 5]

[0440]

[0441]

[0442]

[0443] The cardiocycloene of group 1 may be replaced by substituted or unsubstituted C2-C30 heteroaryl groups (e.g., pyridyl, pyrimidinyl, triazine, thiophene, etc.) instead of the two substituents (O). t Bu) is substituted. The heteroatom (e.g., nitrogen, sulfur, etc.) of the substituted or unsubstituted C2-C30 heteroaryl group may be located at ortho, meta, or para positions relative to the bonding position. The heteroaryl group may be substituted by at least one substituent selected from: C1-C20 straight-chain alkyl, C3-C20 branched alkyl, C6-C12 aryl, and C3-C12 heteroaryl.

[0444] Group 6 illustrates structures in which pyridyl is substituted as the heteroaryl group, and Group 7 illustrates structures in which thiophene, furanyl, pyrrole, selenophene, or tellureneyl is substituted as the heteroaryl group.

[0445] [Group 6]

[0446]

[0447]

[0448]

[0449] In group 6, the pyridyl group may be substituted by at least one substituent selected from the following: C1-C20 straight-chain alkyl, C3-C20 branched alkyl, C6-C12 aryl, and C3-C12 heteroaryl.

[0450] [Group 7]

[0451]

[0452] In group 7, the thiophene, furanyl, pyrrole, selenyl, or telluryl group may be substituted with at least one substituent selected from the following: C1-C20 straight-chain alkyl, C3-C20 branched alkyl, C6-C12 aryl, and C3-C12 heteroaryl. Additionally, the hydrogen atom of the pyrrole group may be substituted with at least one substituent selected from the following: C1-C20 straight-chain alkyl, C3-C20 branched alkyl, C6-C12 aryl, and C3-C12 heteroaryl.

[0453] The phenyl (Ph) group of group 5 or the pyridyl group of group 6 can be fused to a cyclocyclic alkene via an alicyclic hydrocarbon group such as cyclopentadiene. These structures are shown in group 8.

[0454] [Group 8]

[0455]

[0456] The fullerene subunit derivative (N-type semiconductor) may have a content less than or equal to approximately For example, less than or equal to approximately Or less than or equal to approximately The average distance from the P-type semiconductor. By including bulk substituents (X) and additional bulk substituents on the sides, the fullerene subunit derivative can adjust the average distance from the P-type semiconductor within the above range. When the average distance from the P-type semiconductor is maintained within the above range, the fullerene subunit derivative (N-type semiconductor) and the P-type semiconductor can be well mixed to form a bulk heterojunction (BHJ).

[0457] The fullerene subunit derivative may include the following amounts: greater than or equal to about 50 parts by volume, for example greater than or equal to about 60 parts by volume, or greater than or equal to about 70 parts by volume and less than or equal to about 150 parts by volume, for example less than or equal to about 140 parts by volume, or less than or equal to about 130 parts by volume, based on 100 parts by volume of the fullerene or fullerene derivative. Within the above ranges, the fullerene subunit derivative effectively inhibits the aggregation of the fullerene or fullerene derivative, thereby reducing unwanted absorption in the blue region and increasing absorption in the green region.

[0458] The fullerene subunit derivative, together with the fullerene or fullerene derivative, can be formed into a thin film using sublimation vacuum deposition. While maintaining the inherent properties of the fullerene or fullerene derivative during the deposition process, optical properties are prevented from being distorted by the aggregation of fullerene or fullerene derivatives generated during film formation. Thin films made from an N-type semiconductor composition comprising the fullerene or fullerene derivative and the fullerene subunit derivative can reduce anomalous absorption in the short wavelength region of visible light from about 400 nm to about 500 nm. For example, the absorption coefficient of a thin film comprising the N-type semiconductor composition at 450 nm can be less than that of a thin film comprising an unsubstituted fullerene (e.g., C60 fullerene) at 450 nm. For example, the absorption coefficient of a thin film comprising the N-type semiconductor composition at 450 nm can be about 75% or less of the absorption coefficient of a thin film comprising an unsubstituted fullerene (e.g., C60 fullerene) at 450 nm.

[0459] The following describes organic optoelectronic devices comprising the aforementioned N-type semiconductor composition.

[0460] Figure 1 A cross-sectional view illustrating an organic optoelectronic device according to one embodiment.

[0461] Reference Figure 1 According to an embodiment, the organic optoelectronic device 100 includes a first electrode 10 and a second electrode 20 facing each other, and an organic layer 30 disposed between the first electrode 10 and the second electrode 20.

[0462] A substrate (not shown) may be disposed on the side of the first electrode 10 or the second electrode 20. The substrate may be made, for example, of: inorganic materials such as glass; organic materials such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, polyethersulfone, or combinations thereof; or a silicon wafer. The substrate may be omitted.

[0463] One of the first electrode 10 and the second electrode 20 is an anode and the other is a cathode. For example, the first electrode 10 may be a cathode and the second electrode 20 may be an anode.

[0464] At least one of the first electrode 10 and the second electrode 20 may be a light-transmitting electrode, and the light-transmitting electrode may be made, for example, 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 single or multiple metal thin layer. When one of the first electrode 10 and the second electrode 20 is a non-light-transmitting electrode, it may be made of, for example, an opaque conductor such as aluminum (Al), silver (Ag), or gold (Au). For example, both the first electrode 10 and the second electrode 20 may be light-transmitting electrodes. For example, the second electrode 20 may be a light-receiving electrode disposed on the light-receiving side.

[0465] The organic layer 30 may include an active layer (active layer).

[0466] The active layer is a layer comprising P-type and N-type semiconductors to provide a pn junction, which generates excitons by receiving light from the outside and then separates holes and electrons from the generated excitons.

[0467] The P-type semiconductor and the N-type semiconductor may each be a light-absorbing material that absorbs at least a portion of light in the visible light region. For example, the P-type semiconductor may be a light-absorbing material capable of selectively absorbing any of the following: a wavelength region greater than or equal to about 400 nm to less than about 500 nm, a wavelength region from about 500 nm to about 600 nm, and / or a wavelength region greater than about 600 nm and less than or equal to about 700 nm, and the N-type semiconductor may be the aforementioned N-type semiconductor composition.

[0468] In one example, the P-type semiconductor selectively absorbs light in a wavelength region greater than or equal to about 400 nm to less than 500 nm, a wavelength region of about 500 nm to about 600 nm, and a wavelength region greater than about 600 nm and less than or equal to about 700 nm. It can be a light-absorbing material, and the N-type semiconductor can be the aforementioned N-type semiconductor composition. For example, the P-type semiconductor can be an light-absorbing material that selectively absorbs light in a wavelength region of about 500 nm to about 600 nm, and the N-type semiconductor can be the aforementioned N-type semiconductor composition.

[0469] For example, the P-type semiconductor may be a light-absorbing material having a LUMO energy level of about 3.0 eV to about 3.6 eV and a HOMO energy level of about 5.1 eV to about 5.7 eV. Within this range, the P-type semiconductor may be a light-absorbing material having a LUMO energy level of about 3.1 eV to about 3.5 eV and a HOMO energy level of 5.2 eV to about 5.6 eV.

[0470] For example, the P-type semiconductor may be a light-absorbing material having a core structure including, for example, an electron-donating portion, a π-conjugated linker group, and an electron-accepting portion.

[0471] The P-type semiconductor may include, for example, a compound represented by chemical formula 8 as a compound having the core structure, but is not limited thereto.

[0472] [Chemical Formula 8]

[0473]

[0474] In chemical formula 8,

[0475] Y is Se, Te, S, SO, SO2, or SiR h R i ,

[0476] EDG is an electron-donating group.

[0477] EAG is an electron-accepting group, and

[0478] R 21 R 22 R h and R i It can be hydrogen or a monovalent substituent independently.

[0479] Here, the monovalent substituent may be, for example, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl, a substituted or unsubstituted C1-C6 alkoxy, a halogen, or a cyano, but is not limited thereto.

[0480] The P-type semiconductor may be, for example, a light-absorbing material represented by chemical formula 8A, but is not limited thereto.

[0481] [Chemical Formula 8A]

[0482]

[0483] In chemical formula 8A,

[0484] Y is Se, Te, S, SO, SO2, or SiR h R i ,

[0485] Ar p A substituted or unsubstituted 5-membered ring, a substituted or unsubstituted 6-membered ring, or two or more fused rings of the aforementioned rings.

[0486] Ar 1a and Ar 2aIndependently substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, wherein Ar 1a and Ar 2a Exists independently or through connector G 1 Connect them to form a ring, where G 1 For single bond, -(CR) j R k ) n2 -, -O-, -S-, -Se-, -N=, -NR l -、-SiR m R n -、and-GeR o R p - one of them, and n2 is 1 or 2, and

[0487] R 1a -R 3a and R h -R p It is independently hydrogen, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl, a substituted or unsubstituted C1-C6 alkoxy, a halogen, or a cyano.

[0488] The P-type semiconductor may be, for example, a light-absorbing material represented by one of the chemical formulas 8A-1 to 8A-4, but is not limited thereto.

[0489] [Chemical Formula 8A-1]

[0490]

[0491] [Chemical Formula 8A-2]

[0492]

[0493] [Chemical Formula 8A-3]

[0494]

[0495] [Chemical Formula 8A-4]

[0496]

[0497] In chemical formulas 8A-1 to 8A-4,

[0498] Y is Se, Te, S, SO, SO2, or SiR h R i ,

[0499] Z 1 For O or CR q R r,

[0500] Y 1 For N or CR s ,

[0501] Y 2 For O, S, Se, Te, and C(R) t (CN) one of them,

[0502] Y 3 For O, S, Se, or Te,

[0503] Y 4 For N or NR 18a ,

[0504] Y 5 For CR 19a Or C = CR 20a (CN),

[0505] Ar 1a and Ar 2a Independently substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, wherein Ar 1a and Ar 2a They can exist independently or be connected to each other to form a ring.

[0506] R 1a -R 3a R 11a R 12a R 15a -R 20a R 24a R 25a R h R i and R q -R t Independently, it is hydrogen, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl, a substituted or unsubstituted C1-C6 alkoxy, a halogen, or a cyano.

[0507] n1 is 0 or 1, m1 is 0 or 1, and m2 is an integer in the range 0-4.

[0508] The light-absorbing material represented by one of the chemical formulas 8A-1 to 8A-4 may be, for example, one of the compounds in groups 9 to 12, but is not limited thereto.

[0509] [Group 9]

[0510]

[0511] [Group 10]

[0512]

[0513] [Group 11]

[0514]

[0515] [Group 12]

[0516]

[0517] In groups 9-12,

[0518] The hydrogen atoms of each aromatic ring may be replaced by substituents selected from the following: substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C1-C30 alkoxy groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, halogens, cyano groups, cyano-containing groups, and combinations thereof.

[0519] R 16 R 17 R 18 and R 20 Independently, it is hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or a combination thereof.

[0520] The aforementioned N-type semiconductor composition can be used as the N-type semiconductor.

[0521] The fullerene or fullerene derivative has a LUMO level, a HOMO level, and a band gap energy that are effective for electrical matching with the aforementioned P-type semiconductor.

[0522] The P-type semiconductor and the N-type semiconductor composition can be formed as an active layer by using sublimation co-deposition.

[0523] For example, the light absorption characteristics of an active layer comprising the N-type semiconductor composition may differ from those of an active layer comprising an unsubstituted fullerene (e.g., C60 fullerene), and the active layer comprising the N-type semiconductor composition may have reduced anomalous absorption in the short wavelength region of visible light (e.g., from about 400 nm to about 500 nm). For example, the absorption coefficient of the active layer comprising the N-type semiconductor composition at a wavelength of 450 nm may be less than that of the active layer comprising an unsubstituted fullerene (e.g., C60 fullerene) at a wavelength of 450 nm. For example, the absorption coefficient of the active layer comprising the N-type semiconductor composition at a wavelength of 450 nm may be, for example, about 75% or less of the absorption coefficient of the active layer comprising an unsubstituted fullerene (e.g., C60 fullerene) at a wavelength of 450 nm.

[0524] The light absorption characteristics of the active layer can be expressed by combining the light absorption characteristics of the P-type semiconductor with those of the N-type semiconductor composition. Therefore, an active layer comprising a P-type semiconductor and the N-type semiconductor composition that selectively absorbs light in the wavelength region of about 500 nm to about 600 nm exhibits improved wavelength selectivity due to the easier separation of absorption peaks, compared to an active layer comprising a P-type semiconductor and an unsubstituted fullerene (e.g., C60 fullerene) that selectively absorbs light in the wavelength region of about 500 nm to about 600 nm. Therefore, the former active layer can be effectively used in organic optoelectronic devices requiring wavelength selectivity.

[0525] The active layer may include an intrinsic layer (I layer) formed by co-depositing the aforementioned P-type semiconductor and N-type semiconductor composition, and may include the P-type semiconductor and N-type semiconductor composition in a volume ratio of about 1:9 to about 9:1, for example about 2:8 to about 8:2, about 3:7 to about 7:3, about 4:6 to about 6:4, or about 5:5.

[0526] In addition to the intrinsic layer, the active layer may further include a P-type layer and / or an N-type layer. The P-type layer may include the P-type semiconductor, and the N-type layer may include the aforementioned N-type semiconductor composition. For example, the active layer may include various combinations such as a P-type layer / I-layer, an I-layer / N-type layer, a P-type layer / I-layer / N-type layer, etc.

[0527] The organic optoelectronic device 100 may further include a charge-assisted layer (not shown) between the first electrode 10 and the active layer and / or a charge-assisted layer between the second electrode 20 and the active layer. The organic optoelectronic device is shown in... Figure 2 middle.

[0528] Figure 2 A cross-sectional view of an organic optoelectronic device according to another embodiment is shown.

[0529] Reference Figure 2 Similar to the above embodiments, the organic optoelectronic device 200 according to this embodiment includes a first electrode 10 and a second electrode 20 facing each other, and an organic layer 30 between the first electrode 10 and the second electrode 20.

[0530] However, unlike the above embodiments, the organic optoelectronic device 200 according to this embodiment further includes charge-assisted layers 40 and 45 between the first electrode 10 and the active layer and between the second electrode 20 and the organic layer 30.

[0531] The charge-assisted layers 40 and 45 facilitate the transport of holes and electrons separated in the organic layer 30 to improve efficiency.

[0532] The charge-assisted layers 40 and 45 may include at least one selected from: a hole injection layer for promoting hole injection, a hole transport layer for promoting hole transport, an electron blocking layer for preventing electron transport, an electron injection layer for promoting electron injection, an electron transport layer for promoting electron transport, and a hole blocking layer for preventing hole transport.

[0533] The charge-assisted layers 40 and 45 may comprise, for example, organic materials, inorganic materials, or organic / inorganic materials. The organic materials may be organic materials with hole or electron properties, and the inorganic materials may be, for example, metal oxides such as molybdenum oxide, tungsten oxide, or nickel oxide.

[0534] The charge-assisted layers 40 and 45 may include the aforementioned N-type semiconductor composition.

[0535] Organic optoelectronic devices 100 and 200 may further include an anti-reflective layer (not shown) on one surface of the first electrode 10 or the second electrode 20. The anti-reflective layer is disposed on the light incident side and reduces the light reflectivity of the incident light, thereby further improving the light absorption rate. For example, the anti-reflective layer may be disposed on the first electrode 10 when light enters from the first electrode 10, and under the second electrode 20 when light enters from the second electrode 20.

[0536] The antireflective layer may include, for example, a material having a refractive index of about 1.6 to about 2.5, and may include at least one of a metal oxide, a metal sulfide, and an organic material having a refractive index within the said range. The antireflective layer may include, for example, metal oxides such as oxides containing aluminum, oxides containing molybdenum, oxides containing tungsten, oxides containing vanadium, oxides containing rhenium, oxides containing niobium, oxides containing tantalum, oxides containing titanium, oxides containing nickel, oxides containing copper, oxides containing cobalt, oxides containing manganese, oxides containing chromium, oxides containing tellurium, or combinations thereof; metal sulfides such as zinc sulfide; or organic materials such as amine derivatives, but are not limited thereto.

[0537] In organic optoelectronic devices 100 and 200, excitons can be generated internally when light enters from the first electrode 10 or the second electrode 20 and the organic layer 30 (e.g., an active layer) absorbs the light within a predetermined wavelength region. The excitons are separated into holes and electrons in the organic layer 30, and the separated holes are transported to the anode, which is one of the first electrode 10 and the second electrode 20, while the separated electrons are transported to the cathode, which is the other of the first electrode 10 and the second electrode 20, to allow current to flow.

[0538] Organic optoelectronic devices 100 and 200 can be used in solar cells, image sensors, photodetectors, photoelectric sensors, and organic light-emitting diodes (OLEDs), but are not limited thereto.

[0539] The organic optoelectronic device can be used, for example, in image sensors.

[0540] Hereinafter, examples of image sensors including the aforementioned optoelectronic devices are described with reference to the accompanying drawings. An organic CMOS image sensor is described as an example of an image sensor.

[0541] Figure 3 A schematic top plan view of an organic CMOS image sensor according to one embodiment and Figure 4 To display Figure 3 A cross-sectional view of an example of an organic CMOS image sensor.

[0542] Reference Figure 3 and 4 An organic CMOS image sensor 300 according to an example embodiment includes a semiconductor substrate 110 integrating photosensing devices 50a and 50b, a transfer transistor (not shown) and a charge memory 55, a lower insulating layer 60, a color filter layer 70, an upper insulating layer 80, and an organic optoelectronic device 100.

[0543] The semiconductor substrate 110 may be a silicon substrate and integrates photosensing devices 50a and 50b, a transfer transistor (not shown), and a charge storage device 55. The photosensing devices 50a and 50b may be photodiodes.

[0544] Light sensing devices 50a and 50b, a transfer transistor, and / or a charge memory 55 may be integrated in each pixel, and as shown in the figure, light sensing devices 50a and 50b may be included in the blue pixel and the red pixel, respectively, and the charge memory 55 may be included in the green pixel.

[0545] Light sensing devices 50a and 50b sense light, and the information sensed by the light sensing devices can be transmitted through the transmission transistor. Charge memory 55 is electrically connected to organic optoelectronic device 100, which will be described later, and the information in charge memory 55 can be transmitted through the transmission transistor.

[0546] Metal lines (not shown) and pads (not shown) are formed on the semiconductor substrate 110. To reduce signal delay, the metal lines and pads may be made of metals with low resistivity, such as aluminum (Al), copper (Cu), silver (Ag), and their alloys, but are not limited thereto. Furthermore, the structure is not limited to described above, and the metal lines and pads may be disposed beneath the photosensitive devices 50a and 50b.

[0547] A lower insulating layer 60 is formed on the metal wire and the pad. The lower insulating layer 60 may be made of an inorganic insulating material such as silicon oxide and / or silicon nitride, or a low dielectric constant (low K) material such as SiC, SiCOH, SiCO, and SiOF. The lower insulating layer 60 has trenches that expose the charge storage device 55. The trenches may be filled with filler.

[0548] A color filter layer 70 is formed on the lower insulating layer 60. The color filter layer 70 includes a blue filter 70a formed in the blue pixels and a red filter 70b formed in the red pixels. In this embodiment, a green filter is not included, but may be further included.

[0549] An upper insulating layer 80 is formed on the color filter layer 70. The upper insulating layer 80 eliminates the steps created by the color filter layer 70 and smooths the surface. The upper insulating layer 80 and the lower insulating layer 60 may include contact holes (not shown) that expose pads and vias 85 that expose the charge memory 55 of the green pixels.

[0550] The aforementioned organic optoelectronic device 100 is formed on the upper insulating layer 80. As described above, the organic optoelectronic device 100 includes a first electrode 10, an organic layer 30, and a second electrode 20. In the figure, the first electrode 10, the organic layer 30, and the second electrode 20 are stacked sequentially, but this disclosure is not limited thereto, and for example, they may be stacked in the order of the second electrode 20, the organic layer 30, and the first electrode 10.

[0551] The first electrode 10 and the second electrode 20 may both be light-transmitting electrodes, and the organic layer 30 is the same as described above. The organic layer 30 may, for example, selectively absorb light in the green wavelength region and may replace the color filter of the green pixel.

[0552] Light entering from the second electrode 20 in the green wavelength region is mainly absorbed by the organic layer 30 and photoelectrically converted, while light in the remaining wavelength region is transmitted through the first electrode 10 and sensed by the photosensitive devices 50a and 50b.

[0553] A focusing lens (not shown) may be further formed on the organic optoelectronic device 100. The focusing lens can control the direction of the incident light and focus the light into a region. The focusing lens may have, for example, a cylindrical or hemispherical shape, but is not limited thereto.

[0554] As described above, the organic optoelectronic device 100 has a stacked structure, thereby reducing the size of the image sensor to achieve a miniaturized image sensor.

[0555] In addition, the organic layer includes a fullerene derivative having optical absorption properties shifted toward shorter wavelengths as described above, and thus, wavelength selectivity is improved compared to that including unsubstituted C60 fullerenes.

[0556] Organic optoelectronic devices that selectively absorb light in the green wavelength region may be stacked, but this disclosure is not limited thereto. For example, organic optoelectronic devices that selectively absorb light in the blue wavelength region may be stacked and green and red light sensing devices may be integrated in a semiconductor substrate 110, or organic optoelectronic devices that selectively absorb light in the red wavelength region may be stacked and green and blue light sensing devices may be integrated in a semiconductor substrate 110.

[0557] Figure 4 The instructions include Figure 1 The embodiments of the organic optoelectronic device 100 are described, but are not limited thereto, and Figure 2 The optoelectronic device 200 can be applied to it. Figure 5 A cross-sectional view illustrating a CMOS image sensor 300' including an organic optoelectronic device 200.

[0558] Figure 6 A cross-sectional view showing another example of an organic CMOS image sensor.

[0559] The organic CMOS image sensor 400 according to this embodiment, like the embodiments described above, includes a semiconductor substrate 110 integrating photosensitive devices 50a and 50b, a transmission transistor (not shown), and a charge storage device 55, an upper insulating layer 80 having a through-hole 85, and an organic optoelectronic device 100.

[0560] However, unlike the embodiments described above, in the CMOS image sensor 400 according to this embodiment, light sensing devices 50a and 50b are stacked in the vertical direction, but the color filter layer 70 is omitted. Light sensing devices 50a and 50b are electrically connected to a charge memory (not shown) and can be transmitted via the transfer transistor. Light sensing devices 50a and 50b can selectively absorb light in various wavelength regions depending on the stacking depth.

[0561] A focusing lens (not shown) may be further formed on the organic optoelectronic device 100. The focusing lens can control the direction of the incident light and focus the light into a region. The focusing lens may have, for example, a cylindrical or hemispherical shape, but is not limited thereto.

[0562] As described above, organic optoelectronic devices that selectively absorb light in the green wavelength region are stacked, and red and blue light sensing devices are stacked, thereby reducing the size of the image sensor to achieve a miniaturized image sensor.

[0563] exist Figure 6 In this disclosure, organic optoelectronic devices that selectively absorb light in the green wavelength region are stacked, for example, but the disclosure is not limited thereto. For example, organic optoelectronic devices that selectively absorb light in the blue wavelength region may be stacked and green light sensing devices and red light sensing devices may be integrated in the semiconductor substrate 110, or organic optoelectronic devices that selectively absorb light in the red wavelength region may be stacked and green light sensing devices and blue light sensing devices may be integrated in the semiconductor substrate 110.

[0564] Figure 7 A schematic top plan view of an organic CMOS image sensor according to another embodiment is shown. Figure 8 This is a cross-sectional view of an organic CMOS image sensor according to another embodiment.

[0565] The organic CMOS image sensor 500 according to this embodiment includes stacked green organic optoelectronic devices that selectively absorb light in the green wavelength region, blue organic optoelectronic devices that selectively absorb light in the blue wavelength region, and red organic optoelectronic devices that selectively absorb light in the red wavelength region.

[0566] The organic CMOS image sensor 500 according to this embodiment includes a semiconductor substrate 110, a lower insulating layer 60, a middle insulating layer 65, an upper insulating layer 80, a first organic optoelectronic device 100a, a second organic optoelectronic device 100b, and a third organic optoelectronic device 100c.

[0567] The semiconductor substrate 110 may be a silicon substrate and integrates a transfer transistor (not shown) and charge storage devices 55a, 55b, and 55c.

[0568] Metal lines (not shown) and pads (not shown) are formed on the semiconductor substrate 110, and a lower insulating layer 60 is formed on the metal lines and pads.

[0569] The first organic optoelectronic device 100a is formed on the lower insulating layer 60.

[0570] The first organic optoelectronic device 100a includes a first electrode 10a and a second electrode 20a facing each other, and an organic layer 30a disposed between the first electrode 10a and the second electrode 20a. The first electrode 10a, the second electrode 20a, and the organic layer 30a are the same as described above, and the organic layer 30a can selectively absorb light in a wavelength region of red, blue, and green. For example, the first organic optoelectronic device 100a can be a red organic optoelectronic device.

[0571] In the figure, the first electrode 10a, the organic layer 30a, and the second electrode 20a are stacked sequentially, but this disclosure is not limited thereto, and for example, they can be stacked sequentially as the second electrode 20a, the organic layer 30a, and the first electrode 10a.

[0572] An intermediate insulating layer 65 is formed on the first organic optoelectronic device 100a.

[0573] The second organic optoelectronic device 100b is formed on the intermediate insulating layer 65.

[0574] The second organic optoelectronic device 100b includes a first electrode 10b and a second electrode 20b facing each other, and an organic layer 30b disposed between the first electrode 10b and the second electrode 20b. The first electrode 10b, the second electrode 20b, and the organic layer 30b are the same as described above, and the organic layer 30b can selectively absorb light in a wavelength region of red, blue, and green. For example, the second optoelectronic device 100b can be a blue organic optoelectronic device.

[0575] In the figure, the first electrode 10b, the organic layer 30b, and the second electrode 20b are stacked sequentially, but this disclosure is not limited thereto, and for example, they can be stacked sequentially as the second electrode 20b, the organic layer 30b, and the first electrode 10b.

[0576] An upper insulating layer 80 is formed on the second organic optoelectronic device 100b. The lower insulating layer 60, the middle insulating layer 65, and the upper insulating layer 80 have multiple through-holes that expose the charge storage devices 55a, 55b, and 55c.

[0577] A third organic optoelectronic device 100c is formed on an upper insulating layer 80. The third organic optoelectronic device 100c includes a first electrode 10c and a second electrode 20c facing each other, and an organic layer 30c disposed between the first electrode 10c and the second electrode 20c. The first electrode 10c, the second electrode 20c, and the organic layer 30c are the same as described above, and the organic layer 30c can selectively absorb light in a wavelength region of red, blue, and green. For example, the third organic optoelectronic device 100c can be a green organic optoelectronic device.

[0578] In the figure, the first electrode 10c, the organic layer 30c, and the second electrode 20c are stacked sequentially, but this disclosure is not limited thereto, and for example, they can be stacked sequentially as the second electrode 20c, the organic layer 30c, and the first electrode 10c.

[0579] A focusing lens (not shown) may be further formed on the organic optoelectronic device 100c. The focusing lens can control the direction of the incident light and focus the light into a region. The focusing lens may have, for example, a cylindrical or hemispherical shape, but is not limited thereto.

[0580] In the figure, the first organic optoelectronic device 100a, the second organic optoelectronic device 100b, and the third organic optoelectronic device 100c are stacked sequentially, but this disclosure is not limited thereto, and they can be stacked in various orders (different orders).

[0581] As described above, a first organic optoelectronic device 100a, a second organic optoelectronic device 100b, and a third organic optoelectronic device 100c that absorb light in different wavelength regions are stacked, thereby reducing the size of the image sensor to achieve a miniaturized image sensor.

[0582] The image sensor can be applied to various electronic devices such as mobile phones or digital cameras, but is not limited thereto.

[0583] Figure 9 This is a block diagram of a digital camera including an image sensor according to an embodiment.

[0584] Reference Figure 9 The digital camera 1000 includes a lens 1010, an image sensor 1020, a motor 1030, and an engine 1040. The image sensor 1020 can be based on... Figure 3-8 One of the image sensors shown in the embodiment.

[0585] Lens 1010 focuses incident light onto image sensor 1020. Image sensor 1020 generates RGB data for the light received through lens 1010.

[0586] In some implementations, the image sensor 1020 may be interfaced with the engine 1040.

[0587] The motor 1030 can adjust the focus of the lens 1010 or execute the shutter in response to control signals received from the engine 1040. The engine 1040 can control the image sensor 1020 and the motor 1030.

[0588] Engine 1040 can be connected to host / application 1050.

[0589] In exemplary embodiments, motor 1030, engine 1040, and host / application 1050 may include: processing circuitry, such as hardware including logic circuitry; hardware / software combinations, such as a processor executing software; or combinations thereof. For example, the processing circuitry may more specifically include, but is not limited to, a central processing unit (CPU), an arithmetic logic unit (ALU), a digital signal processor, a microcomputer, a field-programmable gate array (FPGA), a system-on-a-chip (SoC), a programmable logic unit, a microprocessor, an application-specific integrated circuit (ASIC), etc.

[0590] The embodiments are described in more detail below with reference to examples. However, these embodiments are exemplary, and the scope of the claims is not limited thereto.

[0591] Synthetic Examples: Synthesis of Fullerene Subunit Derivatives

[0592] Synthesis Example 1

[0593] [Chemical Formula A]

[0594]

[0595] [Reaction Scheme A]

[0596]

[0597] i) Step 1

[0598] A suspension comprising a 1,8-dibromocortinene 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 container of a microwave reactor. After reacting them at 180 °C for 30 min, the suspensions in the container were mixed. Subsequently, NMP was removed by vacuum distillation (less than or equal to 1 Torr, greater than or equal to 50 °C). Chloroform was then added to the residue, and purification was then carried out by silica gel column chromatography (eluent: a mixture of chloroform and hexane in a 1:1 volume ratio).

[0599] After evaporating the solvent from the resulting solution, the resulting solid was dissolved in chloroform, and the resulting product was analyzed using Recycle HPLC (Buckyprep). Separation was performed using chloroform as the eluent. The solvent was evaporated from the solution to give the intermediate (compound (2), 0.7 g, 1.4 mmol, yield: 36.8%).

[0600] ii) Second step

[0601] The intermediate (compound (2), 0.9 g, 1.7 mmol), catalyst Pd(OAc)2 (palladium(II) acetate, 6.5 mg, 0.3 mmol), and base were prepared. t BuONa (sodium tert-butoxide, 0.7g, 7.2mmol), P ( t A toluene solution of Bu (50 wt%, 0.3 ml, 0.6 mmol) and m-xylene (78 ml) were mixed in a flask and then stirred at 130 °C for 12 hours using an oil bath.

[0602] The solvent was then removed using an evaporator (less than or equal to 300 mbar, greater than or equal to 40°C). Chloroform was then added to the residue, and purification was subsequently performed by silica gel column chromatography (eluent: a mixture of chloroform and hexane in a 1:1 volume ratio).

[0603] After evaporating the solvent from the solution, the resulting solid was dissolved in chloroform, and the resulting product was analyzed using Recycle HPLC (Buckyprep). Separation was performed using chloroform as the eluent. The solvent was evaporated from the solution to give the compound represented by chemical formula A (compound (3), 0.6 g, 1.2 mmol, yield: 69.8%).

[0604] 1 H NMR (CDCl3): 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)

[0605] Synthesis Example 2

[0606] [Chemical Formula B]

[0607]

[0608] [Reaction Plan B]

[0609]

[0610] Compound (2) (1.5 g, 2.9 mmol) from Synthetic Example 1, Pd(PPh3)4 (tetra(triphenylphosphine)palladium (0), 0.2 g, 0.2 mmol), Na2CO3 (0.9 g, 8.7 mmol), 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 stirred at 90 °C for 12 hours using an oil bath to give the compound represented by chemical formula B (1.2 g, 2.3 mmol, yield: 78.7%).

[0611] 1 H NMR (CDCl3): 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).

[0612] Synthesis Example 3

[0613] [Chemical formula C]

[0614]

[0615] [Reaction Scheme C]

[0616]

[0617] Compound (2) (1.0 g, 2.0 mmol), Pd(PPh3)4 (0.2 g, 0.1 mmol), Na2CO3 (0.6 g, 5.9 mmol), phenyl borate ester (pinacol ester of 2-tert-butylphenyl borate, 0.3 g, 11.8 mmol), and a mixed solvent (toluene (72 ml), EtOH (32 ml), and water (32 ml)) were mixed and then stirred at 90 °C for 12 hours using an oil bath to give the compound represented by chemical formula C (0.5 g, 0.8 mmol, yield: 40.6%).

[0618] 1 H NMR (CDCl3): 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).

[0619] Synthesis Example 4

[0620] [Chemical formula D]

[0621]

[0622] [Reaction Scheme D]

[0623]

[0624] i) Step 1

[0625] The intermediate (compound (2), 0.8 g, 1.5 mmol, yield: 38.9%) was synthesized according to the same method as in Synthesis Example 1, except that phenylamine (PhNH2) was used instead of isopropylamine in the first step of Synthesis Example 1.

[0626] ii) Second step

[0627] The intermediate (compound (2), 0.7 g, 1.3 mmol), Pd(PPh3)4 (0.1 g, 0.1 mmol), Na2CO3 (0.4 g, 3.7 mmol), phenyl borate ester (2-tert-butylphenyl borate pinacol ester, 1.9 g, 7.4 mmol), and mixed solvent (toluene (44 ml), EtOH (20 ml), and water (20 ml)) were mixed and then stirred at 90 °C for 12 hours using an oil bath to give the compound represented by chemical formula D (compound (3), 0.4 g, 0.6 mmol, yield: 50.1%).

[0628] 1 H NMR (CDCl3): δ 8.35-8.45 (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).

[0629] Synthesis Example 5

[0630] [Chemical Formula E]

[0631]

[0632] [Reaction Scheme E]

[0633]

[0634] i) Step 1

[0635] The intermediate (compound (2), 0.9 g, 1.4 mmol, yield: 37.2%) was synthesized according to the same method as in Synthesis Example 1, except that 2,6-diisopropylphenylamine ((iPr)2C6H3NH2) was used instead of isopropylamine in the first step of Synthesis Example 1.

[0636] ii) Second step

[0637] The intermediate (compound (2), 1.2 g, 1.8 mmol), Pd(PPh3)4 (0.9 g, 5.5 mmol), Na2CO3 (0.6 g, 5.5 mmol), phenyl borate ester (2-isopropylphenyl borate pinacol ester, 0.9 g, 5.5 mmol) and mixed solvent (toluene (48 ml), EtOH (24 ml), and water (24 ml)) were mixed and then reacted at 155 °C for 1 h using a microwave reactor to give the compound represented by chemical formula E (compound (3), 1.0 g, 1.4 mmol, yield: 75.8%).

[0638] 1H NMR(CDCl3): 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).

[0639] Synthetic Comparative Example 1

[0640] [Chemical formula F]

[0641]

[0642] The compound represented by chemical formula F (0.1 g, 0.24 mmol, yield: 85%) was synthesized according to the same method as Scheme 2 disclosed in Synthetic Metals 146 (2004) 251-257, except that benzo[d]thiazolyl-5-ylboronic acid (128.9 mg, 0.72 mmol) was used instead of 9,9-dimethyl-fluorenyl-2-pinacol boronic acid ester.

[0643] 1 H NMR (CDCl3): 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).

[0644] Synthetic Comparative Example 2

[0645] [Chemical formula G]

[0646]

[0647] The compound represented by chemical formula G (1.0 g, 2.7 mmol, yield: 38.0%) was synthesized according to the same method as in Synthesis Example 10 disclosed in patent reference US 2017-069690A1.

[0648] 1 H NMR (DMSO-d6): δ 8.70 (d, 2H), 8.64 (s, 2H), 8.11 (t, 2H), 7.62-7.57 (m, 4H).

[0649] Synthetic Comparative Example 3

[0650] [Chemical formula H]

[0651]

[0652] The compound represented by chemical formula H (4.9 g, 10.1 mmol, yield: 42.0%) was synthesized according to the same method as Preparation Example 1 disclosed in patent reference US 2008-0142792A1, except that 2,3-dibromo-5-(trifluoromethyl)thiophene (3.1 g, 10.0 mmol) was used instead of 2,3-dibromothiophene.

[0653] 1 H NMR (C6D5CD3)d 7.80 (d.2H), 7.45 (s, 4H).

[0654] Synthetic Comparative Example 4

[0655] [Chemical Formula I]

[0656]

[0657] [Reaction Scheme I]

[0658]

[0659] Compound (2) from Synthetic Example 1 (0.2 g, 0.3 mmol), catalyst Pd(dba)2 (bis(dibenzylacetone)palladium(0), 26.4 mg, 0.1 mmol), base Cs2CO3 (17.8 mg, 0.8 mmol), SPhos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 20.9 mg, 50.9 μmol), m-xylene (61 mL), and IPA (isopropanol, 5.0 mL) were mixed in a flask and then stirred at 80 °C for 12 hours using an oil bath. The solvent was then removed using an evaporator (≤300 mbar, ≥40 °C). The residue was then added to chloroform and purified by silica gel column chromatography (eluent: chloroform and hexane in a 1:1 volume ratio).

[0660] After evaporating the solvent from the solution, the resulting solid is dissolved in chloroform, and the product is then analyzed using Recycle HPLC (Buckyprep). Separation was performed using chloroform as the eluent. The solvent was evaporated from the solution to give the product (0.1 g, 0.2 mmol, yield: 60.2%).

[0661] 1 H NMR (CDCl3): δ 8.45 (d, 2H), 7.95 (d, 2H), 7.85 (d, 4H), 4.52-4.66 (m, 1H), 1.55 (s, 6H).

[0662] Comparative Example 5: C60 Fullerene

[0663] [Chemical formula J]

[0664]

[0665] C60 fullerene (Nanom purple ST, Frontier Carbon Corp.) was used.

[0666] Example 1: Fabrication of an Organic Optoelectronic Device

[0667] ITO was sputtered and deposited on a glass substrate to form an anode with a thickness of about 150 nm, and a N-type semiconductor composition including a fullerene subunit derivative represented by Chemical formula A (N-type semiconductor compound) according to Synthesis Example 1 and C60 fullerene represented by Chemical formula J, and a compound represented by Chemical formula X (P-type semiconductor compound) were co-deposited thereon to form an active layer with a thickness of 100 nm. The N-type semiconductor composition and the P-type semiconductor compound were used in a volume ratio of 1:1, and the N-type semiconductor composition included the fullerene subunit derivative (N-type semiconductor compound) and C60 fullerene represented by Chemical formula J in a volume ratio of 2:3. On the active layer, a 10-nm-thick molybdenum oxide (MoOx, where 0 < x ≤ 3) thin film was formed as a charge-assist layer. Subsequently, ITO was deposited by sputtering on the molybdenum oxide thin film to form a cathode with a thickness of 7 nm, and an organic optoelectronic device was fabricated.

[0668] [Chemical formula X]

[0669]

[0670] Examples 2 - 5 and Comparative Examples 4 and 5: Fabrication of Organic Optoelectronic Devices

[0671] Organic optoelectronic devices were fabricated according to the same method as in Example 1, except that the fullerene subunit derivatives according to Synthesis Examples 2 - 5 and Synthesis Comparative Example 4 were used respectively instead of the fullerene subunit derivative represented by Chemical formula A according to Synthesis Example 1.

[0672] The organic optoelectronic device of Comparative Example 5 was fabricated according to the same method as in Example 1, except that C60 fullerene and the P-type semiconductor compound were co-deposited in a volume ratio of 1:1 to form the active layer, without using the fullerene derivative represented by Chemical formula A according to Synthesis Example 1.

[0673] Examples 6 - 10 and Comparative Examples 6 and 7: Fabrication of an Organic CMOS Image Sensor (OCIS)

[0674] The organic optoelectronic devices according to Examples 1 - 5 and Comparative Examples 4 and 5 were used respectively as having Figure 4 The image sensor 300 shown is manufactured using an organic optoelectronic device 100.

[0675] Evaluation 1: Deposition temperature of fullerene subunit derivatives

[0676] To evaluate the thermal stability of the fullerene subunit derivatives synthesized according to Examples 1-5, the deposition temperature (Ts) at which 10% by weight sublimated at 10 Pa was measured. 10 ) and the deposition temperature (Ts) at which 50% by weight sublimation occurs at 10 Pa. 50 In addition, the deposition temperatures of the compounds synthesized according to Comparative Examples 1-5 were measured. Here, all samples were prepared by thoroughly drying purified powders to a purity greater than or equal to 99.9%, and the deposition temperatures were measured by thermogravimetric analysis (TGA). The results of synthesizing Examples 1-5 and the compounds synthesized according to Comparative Examples 1-3 and 5 are shown in Table 1.

[0677] (Table 1)

[0678]

[0679]

[0680] *T s (-10 wt%) (°C): The temperature at which 10 wt% of the sample weight sublimates.

[0681] *T s (-50 wt%) (°C): The temperature at which 50 wt% of the sample weight sublimates.

[0682] Referring to Table 1, the fullerene subunit derivatives from synthesis Examples 1-5 exhibited lower deposition temperatures than the compounds from synthesis Comparative Examples 1-3 and 5. Therefore, the fullerene subunit derivatives from synthesis Examples 1-5 have been shown to be compounds capable of being deposited via sublimation.

[0683] Evaluation 2: Energy levels of fullerene subunit derivatives

[0684] Fullerene subunit derivatives according to Synthesis Examples 1-5 were deposited to form thin films, and the HOMO and LUMO levels of each film were measured using the B3LYP / 6-31G(d) energy level theory described in "MJ Frisch et al., Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT 2009" using the Gaussian 09 procedure. The results of Synthesis Examples 1-5 and Synthesis Comparative Example 5 are shown in Table 2. For reference, the HOMO and LUMO levels of compounds represented by the chemical formulas K and L as p-type semiconductor compounds are provided.

[0685] (Table 2)

[0686] compound HOMO(eV) LUMO(eV) Chemical Formula A (Synthesis Example 1) -6.3 -2.9 Chemical formula B (Synthesis Example 2) -6.3 -3.0 Chemical formula C (Synthesis Example 3) -6.4 -3.0 Chemical formula D (Synthesis Example 4) -6.5 -3.1 Chemical formula E (Synthesis Example 5) -6.4 -3.1 Chemical formula J (C60, comparative example 5) -6.4 -3.7 Chemical formula K -5.4 -2.5 Chemical formula L -5.6 -2.6

[0687] The chemical formulas K and L shown in Table 2 have the following structures.

[0688]

[0689] Referring to Table 2, when the compounds of Synthetic Examples 1-5 were measured using a B3LYP / 6-31G(d) with reference to "MJ Frisch et al., Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT 2009", their HOMO energy levels were comparable to those of C60, and their LUMO energy levels were not high enough to be used as N-type semiconductors. Compared to the HOMO and LUMO energy levels of compounds of the chemical formulas K and L, which are P-type semiconductor compounds, the compounds of Synthetic Examples 1-5 are suitable for use as N-type semiconductor compounds.

[0690] Evaluation 3: The distance between N-type and P-type semiconductors

[0691] The morphology of the active layer formed on a substrate by co-deposition of N-type and P-type semiconductors was evaluated using Nanomatch software. The results of calculating the average distance between the N-type and P-type semiconductors (compounds represented by chemical formula X) in the active layer are shown in Table 3. The morphology of the virtually formed blend obtained using the software was used to calculate the average distance, and the results are shown in Table 3.

[0692] (Table 3)

[0693]

[0694] The structures of chemical formulas M to Q shown in Table 3 are as follows.

[0695]

[0696]

[0697] Referring to Table 3, the compounds represented by chemical formulas A to E and M to Q include bulky substituent X and additional bulky substituents on their sides, and therefore have a shorter distance to the P-type semiconductor compared to the compound represented by chemical formula I, which does not have bulky substituents. This is because the crystallization of the compounds represented by chemical formulas A to E and M to Q (N-type semiconductors) is further reduced or suppressed compared to the crystallization of the compound represented by chemical formula I, thus these compounds mix well with the P-type semiconductor and form an active layer. Therefore, the crystallinity of these compounds is not only sufficiently low, but the compounds represented by chemical formulas A to E and M to Q also mix well with the P-type semiconductor.

[0698] Evaluation 4: External quantum efficiency characteristics of the device

[0699] The external quantum efficiency (EQE) of the organic optoelectronic devices according to Examples 1-5 and Comparative Examples 4 and 5 was measured. The EQE was measured using an IPCE measurement system (McScience Inc, Korea). First, a Si photodiode (Hamamatsu Photonics KK, Japan) calibration system was used, and the organic optoelectronic devices according to Examples 1-5 and Comparative Examples 4 and 5 were mounted thereon, and the EQE was measured in the wavelength range of approximately 350 nm to 750 nm. The results for Examples 1-5 and Comparative Examples 4 and 5 are shown in Table 4.

[0700] (Table 4)

[0701]

[0702]

[0703] Referring to Table 4, compared with the absorption of the organic optoelectronic device in the blue region of Comparative Example 5, the absorption of the organic optoelectronic devices according to Examples 1-5 in the blue region is reduced by 30% to 50% or more. The absorption of C60 in the blue region (450 nm) is known to be due to the aggregation of C60 (Journal of Molecular Structure 526(2000)25-29). In other words, the reduced absorption of the organic optoelectronic devices of Examples 1-5 in the blue region (450 nm) means that the aggregation of C60 is reduced or disappears. Therefore, the anomalous light absorption properties of the organic optoelectronic devices of Examples 1-5 in the blue region do not occur.

[0704] On the other hand, similar to Examples 1-5, Comparative Example 4 showed a decrease in EQE in the blue region at room temperature before annealing, but its EQE performance deteriorated across the entire visible light region (blue / green / red) after annealing.

[0705] Although not bound by any theory, the reason why the EQE performance of the organic optoelectronic devices in Examples 1-5 did not deteriorate after annealing is that the fullerene subunit derivatives contain three bulky substituents in the centrifugal ene and therefore do not crystallize at high temperatures. On the other hand, Comparative Example 4, which includes a bulky substituent X in the centrifugal ene, crystallizes due to annealing. Therefore, the fullerene subunit derivatives with a bulky substituent exhibit low thermal stability.

[0706] Evaluation 5: Absorption coefficient within the blue area

[0707] The absorption coefficient in the blue region (450 nm) was measured for the organic optoelectronic devices of Examples 1-5 and Comparative Examples 4 and 5. The results for Examples 1-5 and Comparative Example 5 are shown in Table 5.

[0708] (Table 5)

[0709]

[0710] Referring to Table 5, compared with the absorption of the organic optoelectronic device in the blue region of Comparative Example 5, the absorption of the organic optoelectronic devices in Examples 1-5 in the blue region is reduced by 25% or more.

[0711] Evaluation 6: Migration Rate

[0712] The mobility of the organic optoelectronic devices of Examples 1-5 and Comparative Examples 4 and 5 was measured. The mobility was measured according to the space charge confinement current (SCLC) method disclosed in Solar Energy Materials & Solar Cells 141 (2015) 87-92. The results of Examples 1-5 and Comparative Example 5 are shown in Table 6.

[0713] (Table 6)

[0714]

[0715] Referring to Table 6, the mobility of the organic optoelectronic devices in Examples 1-5 is 1.65 times higher or more than that of the organic optoelectronic device in Example 5.

[0716] Since the partial aggregation of C60 in the bulk heterojunction (BHJ) of the active layer is reduced or suppressed by the fullerene subunit derivative, the mobility can be improved by suppressing charge loss at the aggregation sites. Furthermore, the fullerene subunit derivative has N-type properties and therefore can act as a charge transporter and improve mobility.

[0717] Rating 7: YSNR10

[0718] For YSNR10, the evaluation includes the image sensors of Examples 6-10 and Comparative Examples 6 and 7, which are organic optoelectronic devices of Examples 1-5 and Comparative Examples 4 and 5, respectively.

[0719] YSNR10 was measured by photographing an 18% gray patch of the Macbeth chart under a D-65 light source. The lens used had an F-number of 2.8 and 80% transmittance, and an interferometric lens was used as an infrared stop filter. The image sensor had a pixel size of 1.4 μm and a frame rate of 15 fps.

[0720] Here, YSNR10 was used to evaluate the sensitivity of the image sensor and was measured according to the method of Juha Alakarhu, “Image Sensors and Image Quality in Mobile Phones,” published in the outline of the 2007 International Image Sensor Workshop (Ogunquit Maine, USA), but the lowest brightness with a signal-to-noise ratio of 10 was expressed as lux. The results for the image sensors including the organic optoelectronic devices of Example 1 and Comparative Example 5 are shown in Table 7.

[0721] (Table 7)

[0722]

[0723] Referring to Table 7, compared with the image sensor including the organic optoelectronic device of Comparative Example 5, the image sensor including the organic optoelectronic device of Example 1 exhibits a 10% improvement in YSNR10.

[0724] Although this disclosure has been described with respect to exemplary embodiments which are now considered practical, it will be understood that the inventive concept is not limited to the disclosed embodiments. Rather, the inventive concept is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

[0725] <Symbol Explanation>

[0726] 100: Organic optoelectronic devices

[0727] 10: First electrode

[0728] 20: Second electrode

[0729] 30: Organic layer

[0730] 300, 400, 500: Organic CMOS image sensors.

Claims

1. An N-type semiconductor composition, comprising: Fullerenes or fullerene derivatives; and Derivatives of fullerene subunits represented by chemical formula 1: [Chemical Formula 1] In chemical formula 1, Cy is a cyclic group selected from C3-C20 alicyclic groups and C6-C20 aromatic groups, or a fused cyclic group of two or more cyclic groups. The cyclic group in Cy is a heterocyclic group comprising at least one functional group selected from the following: -N=, -NR-, -O-, -S-, -Se-, -Te-, -C(=O)-, -C(=S)-, -C(=Se)-, -C(=Te)-, -C(=C(CN)2)-, and -C(=NR)-, wherein R is a C1-C10 alkyl group. X is at least one bulky substituent selected from the following: substituted or unsubstituted C3-C30 branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. R 2 and R 7 The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof, and R 1 R 3 R 4 R 5 R 6 and R 8 It is hydrogen, deuterium, halogen, cyano, C1-C20 straight-chain alkyl or a combination thereof.

2. The N-type semiconductor composition of claim 1, wherein in formula 1, Cy is pyrrole, furan, pyrrolin, pyrrolidinone, cyclopentanedione, pyrrolidinone, pyrrolidinone, pyrrolidinone comprising a ketone (C=O) group in the ring, pyridine, pyrimidine, indole, phthalimide, benzimidazole, benzothiazole, or a fused ring of the foregoing rings and benzene rings.

3. The N-type semiconductor composition of claim 1, wherein in chemical formula 1, Cy is selected from the portions represented by chemical formulas 2A to 2C: [Chemical Formula 2A] in, In chemical formula 2A, Y 1 For CR a R b or NR c , R a and R b Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof. The condition is R a and R b At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. R c The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. Z 1 and Z 2 For O, S, Se, Te, C(CN)2 or NR d , where R d It is a C1-C10 alkyl group or Y attached to the chemical formula 2A. 1 To provide fused rings, and *=* represents the part connecting to chemical formula 1. [Chemical Formula 2B] In chemical formula 2B, Y 2 For CR a R b NR c ,O,S,Se or Te, Where R a R b and R c Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof, R x It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof. When Y 2 For CR a R b or NR c At that time, R a R b and R x At least one of and R c and R x At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. When Y 2 When R is O, S, Se or Te x The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. *=* represents the part connecting to chemical formula 1. [Chemical formula 2C] In the chemical formula 2C, Y 2 For NR c ,O,S,Se or Te, Where R c It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof. R x and R y It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof. When Y 2 For NR c At that time, R c R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. When Y 2 When R is O, S, Se or Te x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. *=* is the part connecting to chemical formula 1.

4. The N-type semiconductor composition of claim 1, wherein in chemical formula 1, Cy is selected from the portions represented by chemical formulas 3A to 3D: [Chemical Formula 3A] in, In chemical formula 3A, R x R y and R z Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof. R x R y and R z At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. *=* represents the part connecting to chemical formula 1. [Chemical Formula 3B] In the chemical formula 3B, R x and R y Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof. R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. *=* represents the part connecting to chemical formula 1. [Chemical formula 3C] Among them, in the chemical formula 3C, R x and R y Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof. R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. *=* represents the part connecting to chemical formula 1. [Chemical Formula 3D] In chemical formula 3D, R x and R y Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof. R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. *=* is the part connecting to chemical formula 1.

5. The N-type semiconductor composition of claim 1, wherein in chemical formula 1, Cy is selected from the portions represented by chemical formulas 4A to 4C: [Chemical Formula 4A] in, In chemical formula 4A, Y 1 For CR a R b or NR c , R a and R b Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof. The condition is R a and R b At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. R c The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. R p R q R r and R s Independently hydrogen, deuterium, or C1-C10 alkyl. n is an integer between 0 and 2. Z 1 and Z 2 For O, S, Se, Te, C(CN)2 or NR d , where R d It is a C1-C10 alkyl group or Y attached to chemical formula 4A 1 To provide fused rings, and *=* represents the part connecting to chemical formula 1. [Chemical Formula 4B] In the chemical formula 4B, Y 2 For CR a R b NR c ,O,S,Se or Te, Where R a R b and R c Independently, it is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or a combination thereof. R x It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof. When Y 2 For CR a R b or NR c At that time, R a R b and R x At least one of and R c and R x At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. When Y 2 When R is O, S, Se or Te x The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. n is an integer between 0 and 2. R p R q R r and R s Independently hydrogen, deuterium, or C1-C10 alkyl, and *=* represents the part connecting to chemical formula 1. [Chemical formula 4C] In the chemical formula 4C, Y 2 For NR c ,O,S,Se or Te, Where R c It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof. R x and R y It can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof. When Y 2 For NR c At that time, R c R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. When Y 2 When it is O, S, Se or Te, R x and R y At least one of the following bulk substituents is selected from: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof. n is an integer between 0 and 2. R p R q R r and R s Independently hydrogen, deuterium, or C1-C10 alkyl, and *=* is the part connecting to chemical formula 1.

6. The N-type semiconductor composition of claim 1, wherein... In chemical formula 1, R 2 and R 7 At least one of them is a group represented by chemical formula 5A: [Chemical Formula 5A] in, In chemical formula 5A, R a and R b It can be hydrogen, halogen, cyano, or C1-C6 alkyl. n1 is an integer between 0 and 10, and R 11 -R 13 It is hydrogen, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl, provided that R 11 -R 13 At least two of them are C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl or C2-C10 alkynyl.

7. The N-type semiconductor composition of claim 1, wherein... In chemical formula 1, R 2 and R 7 At least one of them is a group independently represented by chemical formula 5B: [Chemical Formula 5B] in, In chemical formula 5B, R c and R d It can be hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C2-C10 ether, or C2-C10 ester. n² is an integer between 2 and 10. -C(R c R d - is replaced by at least one functional group selected from the following: -O-, -S-, -S(=O)-, -S(=O)2-, -C(=O-, -C(=O)O-, -OC(=O-)-, and combinations thereof, and R 21 -R 23 It is hydrogen, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, or C2-C10 alkynyl, provided that R 21 -R 23 At least two of them are C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl or C2-C10 alkynyl.

8. The N-type semiconductor composition of claim 1, wherein... In chemical formula 1, R 2 and R 7 At least one of them is a group represented by the chemical formula 5C: [Chemical formula 5C] in, In the chemical formula 5C, R e and R f It can be hydrogen, halogen, cyano, or C1-C6 alkyl. n3 is an integer between 0 and 10, and R 31 -R 33 It is hydrogen, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, or C1-C10 alkylsilyl, provided that R 31 -R 33 At least two of them are C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl or C2-C10 alkynyl.

9. The N-type semiconductor composition of claim 1, wherein... In chemical formula 1, R 2 and R 7 At least one of the following is independently isopropyl, 1-methylpropyl, isobutyl, 1-methylbutyl, 1-ethylbutyl, 1-propylbutyl, isopentyl, 1-methylpentyl, 1-ethylpentyl, 1-propylpentyl, 2-methylpentyl, 2-ethylpentyl, 2-propylpentyl, 3-methylpentyl, 3-ethylpentyl, 3-propylpentyl, isohexyl, 1-methylhexyl, 1-ethylhexyl, 1-propylhexyl, 2-methylhexyl, 2-ethylhexyl, 2-propylhexyl, 3-methylhexyl, 3-ethylhexyl, 3-propyl Hexyl, isoheptyl, 1-methylheptyl, 1-ethylheptyl, 1-propylheptyl, 2-methylheptyl, 2-ethylheptyl, 2-propylheptyl, 3-methylheptyl, 3-ethylheptyl, 3-propylheptyl, isooctyl, 1-methyloctyl, 1-ethyloctyl, 1-propyloctyl, 2-methyloctyl, 2-ethyloctyl, 2-propyloctyl, 3-methyloctyl, 3-ethyloctyl, 3-propyloctyl, 1-methylnonyl, 1,1-dimethylnonyl, tert-butyl, tert-pentyl, tert-hexyl, neopentyl or neohexyl.

10. An N-type semiconductor composition comprising: Fullerenes or fullerene derivatives; and Fullerene subunit derivatives represented by chemical formula 1A: [Chemical Formula 1A] In chemical formula 1A, Cy is a cyclic group selected from C3-C20 alicyclic groups and C6-C20 aromatic groups, or a fused cyclic group of two or more cyclic groups. The cyclic group in Cy is a heterocyclic group comprising at least one functional group selected from the following: -N=, -NR-, -O-, -S-, -Se-, -Te-, -C(=O)-, -C(=S)-, -C(=Se)-, -C(=Te)-, -C(=C(CN)2)-, and -C(=NR)-, wherein R is a C1-C10 alkyl group. X is at least one bulky substituent selected from the following: substituted or unsubstituted C3-C30 branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. R 1 R 2a R 4 R 5 R 6a and R 8 Independently comprising hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C3-C20 straight-chain or branched alkylsilyl, substituted or unsubstituted C2-C20 straight-chain or branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, or combinations thereof, and a1 and a2 are independent integers from 1 to 4.

11. An N-type semiconductor composition comprising: Fullerenes or fullerene derivatives; and Derivatives of fullerene subunits represented by chemical formula 1: [Chemical Formula 1] In chemical formula 1, Cy includes C3-C20 alicyclic cyclic groups, C6-C20 aromatic cyclic groups, or fused cyclic groups of two or more cyclic groups. The cyclic group in Cy is a heterocyclic group comprising at least one functional group selected from the following: -N=, -NR-, -O-, -S-, -Se-, -Te-, -C(=O)-, -C(=S)-, -C(=Se)-, -C(=Te)-, -C(=C(CN)2)-, and -C(=NR)-, wherein R is a C1-C10 alkyl group. X includes substituted or unsubstituted C3-C30 branched alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C3-C30 heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups, and R 2 and R 7 The substituent is selected from the following bulky substituents: substituted or unsubstituted C3-C20 branched alkyl, substituted or unsubstituted C3-C20 branched alkoxy, substituted or unsubstituted C3-C20 branched alkylsilyl, substituted or unsubstituted C3-C20 branched heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, and combinations thereof, and R 1 R 3 R 4 R 5 R 6 and R 8 It is hydrogen, deuterium, halogen, cyano, C1-C20 straight-chain alkyl or a combination thereof.

12. Membranes, including: The N-type semiconductor composition according to any one of claims 1-11.

13. The membrane of claim 12, wherein the absorption coefficient of the membrane at a wavelength of about 450 nm is less than the absorption coefficient of the membrane comprising unsubstituted C60 fullerene at a wavelength of about 450 nm.

14. Organic optoelectronic devices, including: The first and second electrodes facing each other, and An organic layer between the first electrode and the second electrode The organic layer comprises the N-type semiconductor composition as described in any one of claims 1-11.

15. The organic optoelectronic device of claim 14, wherein... The organic layer includes an active layer. The active layer includes a P-type semiconductor and an N-type semiconductor forming a pn junction, and The N-type semiconductor includes the N-type semiconductor composition.

16. The organic optoelectronic device of claim 15, wherein... The fullerene subunit derivative has an average distance of less than or equal to 6 Å from the p-type semiconductor.

17. An image sensor, including: The organic optoelectronic device as described in claim 14 or 15.

18. Electronic devices, including: The organic optoelectronic device as described in claim 14 or 15.

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