# US 11,910,698 B2 · Infrared absorption composition, and photoelectric device, organic sensor, and electronic device including the same

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,910,698 B2
- Document ID: US11910698B2
- Status: Granted
- Kind: B2
- Application number: 17/323,294
- Filed: 2021-05-18
- Published: 2021-11-25
- Granted: 2024-02-20
- Earliest claimed: 2020-05-19
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Insun Park; Rae Sung Kim; Dong-Seok Leem
- Web page: https://patentgrep.com/patent/US11910698B2

## CPC

- H10K 85/311: {Phthalocyanine}
- H10K 85/215: {comprising substituents, e.g. PCBM}
- H10K 85/30: Coordination compounds
- H10K 85/331: {Metal complexes comprising an iron-series metal, e.g. Fe, Co, Ni}
- H10K 85/381: {Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K 39/32: Organic image sensors
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Disclosed are an infrared absorption composition, and a photoelectric device, an organic sensor, and an electronic device including the same. The infrared absorption composition includes a p-type semiconductor compound represented by Chemical Formula 1 and an n-type semiconductor compound. The n-type semiconductor compound includes a compound represented by Chemical Formula 2A, a compound represented by Chemical Formula 2B, a compound represented by Chemical Formula 2C, a fullerene derivative, or a combination thereof. The p-type semiconductor compound and the n-type semiconductor compound provide a bulk heterojunction (BHJ) structure.

## Claims

### Claim 1

An infrared absorption composition, comprising
a p-type semiconductor compound represented by Chemical Formula 1, and
an n-type semiconductor compound including a compound represented by Chemical Formula 2A, a compound represented by Chemical Formula 2B, a compound represented by Chemical Formula 2C, a fullerene derivative, or a combination thereof,
wherein the p-type semiconductor compound and the n-type semiconductor compound provide a bulk heterojunction (BHJ) structure,
wherein, in Chemical Formula 1,
M is Sn, Ni, V, Al, Zn, Si, Co, or Ge,
X is a halogen,
m is an integer from 0 to 4,
n is 0 or 1,
two R1a's, two R2a's, two R3a's, and two R4a's are each independently hydrogen, deuterium, a halogen, a cyano group, a C1 to C20 haloalkyl group, a C1 to C20 cyanoalkyl group, a C1 to C20 alkyl group, or a C1 to C20 alkoxy group, provided that at least one of two R1a's, at least one of two R2a's, at least one of two R3a's, and at least one of two R4a's are a C1 to C20 alkyl group or a C1 to C20 alkoxy group,
R1b, R1c, R1d, R2b, R2c, R2d, R3b, R3c, R3d, R4b, R4c and R4d are each independently hydrogen, deuterium, a halogen, a C1 to C20 haloalkyl group, a cyano group, a C1 to C20 cyanoalkyl group, a C1 to C20 alkyl group, or a C1 to C20 alkoxy group,
b is an integer of 0 to 2, and
n1, n2, n3, and n4 are each independently an integer from 1 to 4,
wherein, in Chemical Formula 2A,
Ar1 is one of the moieties represented by Chemical Formula 3,
X1 and X2 are each independently S, Se, or Te,
Ar11, Ar12, Ar21, and Ar22 are each independently a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C10 heteroaryl group,
Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, or a fused ring thereof, and
R1 and R2 are each independently hydrogen or a C1 to C10 alkyl group,
wherein, in Chemical Formula 3,
Xa and Xb are each independently S, Se, or Te,
Ra and Rb are each independently hydrogen or a C1 to C20 alkyl group, and
a and b are each independently 1 or 2,
wherein, in Chemical Formula 2B,
Ar2 is one of the moieties represented by Chemical Formula 3,
X1, X2, X3, and X4 are each independently S, Se, or Te,
Ar11, Ar12, Ar21, and Ar22 are each independently a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C10 heteroaryl group,
Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, or a fused ring thereof, and
R1 and R2 are each independently hydrogen or a C1 to C10 alkyl group,
wherein, in Chemical Formula 2C,
Ar3 is one of the moieties represented by Chemical Formula 4,
X1, X2, X3, and X4 are each independently S, Se, or Te,
R3 and R4 are each independently hydrogen, a C1 to C20 alkyl group, a C6 to C10 aryl group, or a C2 to C10 heteroaryl group,
Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, or a fused ring thereof, and
R1 and R2 are each independently hydrogen or a C1 to C10 alkyl group,
wherein, in Chemical Formula 4,
Y1 is CRpRq, NRr, O, S, Se, or Te, wherein Rp, Rq, and Rr are each independently hydrogen or a C1 to C20 alkyl group, and
Z1 to Z4 are each independently CRs or N, wherein Rs is hydrogen or a C1 to C20 alkyl group.

### Claim 2 (depends on 1)

The infrared absorption composition of claim 1, wherein the p-type semiconductor compound represented by Chemical Formula 1 is one of compounds represented by Chemical Formulas 1A to 1C:
wherein, in Chemical Formulas 1A to 1C,
R1a, R1b, R1c, R1d, R2a, R2b, R2c, R2d, R3a, R3b, R3c, R3d, R4a, R4b, R4c, R4d, b, n1, n2, n3, and n4 are the same as in Chemical Formula 1,
wherein, in Chemical Formula 1C,
R5a and R5b are hydrogen, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group.

### Claim 3 (depends on 1)

The infrared absorption composition of claim 1, wherein in Chemical Formula 1, X is Cl.

### Claim 4 (depends on 1)

The infrared absorption composition of claim 1, wherein in Chemical Formula 1, two R1a's, two R2a's, two R3a's, and two R4a's are a C1 to C20 alkyl group or a C1 to C20 alkoxy group.

### Claim 5 (depends on 1)

The infrared absorption composition of claim 1, wherein in Chemical Formulas 2A and 2B, Ar11, Ar12, Ar21, and Ar22 are each independently:
a C6 to C10 aryl group substituted with a C1 to C20 alkyl group or a C1 to C20 alkoxy group, or
a C3 to C10 heteroaryl group substituted with a C1 to C20 alkyl group or a C1 to C20 alkoxy group.

### Claim 6 (depends on 1)

The infrared absorption composition of claim 1, wherein in Chemical Formulas 2A, 2B, and 2C, Ar31 and Ar32 are a cyclic group represented by one of Chemical Formulas 5A to 5F:
wherein, in Chemical Formula 5A,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
Z3 is N or CRc, wherein Rc is hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group,
R11, R12, R13, R14, and R15 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof, wherein R12, R13, R14, and R15 are each independently present or R12 and R13 and R14 and R15 are linked to each other to provide a fused aromatic ring,
n is 0 or 1, and
* is a linking position,
wherein, in Chemical Formula 5B,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
Z3 is O, S, Se, Te, or C(Ra)(CN), wherein Ra is hydrogen, a cyano group (—CN), or a C1 to C10 alkyl group,
R11 and R12 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), or a combination thereof, and
* is a linking position,
wherein, in Chemical Formula 5C,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
R11, R12, and R13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), or a combination thereof,
* is a linking position,
wherein, in Chemical Formula 5D,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
Z3 is N or CRc, wherein Rc is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
G1 is O, S, Se, Te, SiRxRy, or GeRzRw, wherein Rx, Ry, Rz, and Rw are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R11, R12, and R13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or a combination thereof, wherein R12 and R13 are each independently present or linked to each other to provide a fused aromatic ring,
n is 0 or 1,
* is a linking position,
wherein, in Chemical Formula 5E,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
Z3 is N or CRc, wherein Rc is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
G2 is O, S, Se, Te, SiRxRy, or GeRzRw, wherein Rx, Ry, Rz, and Rw are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R11, R12, and R13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or a combination thereof,
n is 0 or 1, and
* is a linking position,
wherein, in Chemical Formula 5F,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
R11 is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof, and
G3 is O, S, Se, Te, SiRxRy, or GeRzRw, wherein Rx, Ry, Rz, and Rw are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

### Claim 7 (depends on 1)

The infrared absorption composition of claim 1, wherein
the compound represented by Chemical Formula 2A is a compound represented by Chemical Formula 2A-1, and
the compound represented by Chemical Formula 2B is a compound represented by Chemical Formula 2B-1:
wherein, in Chemical Formula 2A-1,
Ar1 is one of the moieties represented by Chemical Formula 3,
X1 and X2 are each independently S, Se, or Te,
R1 and R2 are each independently hydrogen or a C1 to C10 alkyl group,
R11, R12, R21, and R22 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, x1, y1, x2, and y2 are each independently an integer from 0 to 5, and
Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, or a fused ring thereof,
wherein, in Chemical Formula 2B-1,
Ar2 is one of the moieties represented by Chemical Formula 3,
X1, X2, X3, and X4 are each independently S, Se, or Te,
R1 and R2 are each independently hydrogen or a C1 to C10 alkyl group,
R11, R12, R21, and R22 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, x1, y1, x2, and y2 are each independently an integer from 0 to 5, and
Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, or a fused ring thereof.

### Claim 8 (depends on 1)

The infrared absorption composition of claim 1, wherein the fullerene derivative comprises a C60 to C120 fullerene substituted with a first functional group of an aryl group or a heterocyclic group and a second functional group of an alkyl ester group.

### Claim 9 (depends on 1)

The infrared absorption composition of claim 1, wherein the fullerene derivative comprises [6,6]-phenyl-C61-butyric acid methyl ester (PC60BM), bis(1-[3-(methoxycarbonyl)propyl]-1-phenyl)-[6,6]C62 (bis-PCBM), phenyl-C70-butyric acid methyl ester (PC70BM), indene-C60 bisadduct (ICBA), or indene-C60 monoadduct (ICMA).

### Claim 10 (depends on 1)

The infrared absorption composition of claim 1, wherein the p-type semiconductor compound and the n-type semiconductor compound are included in a volume ratio (p:n) of about 1:0.1 to about 1:10.

### Claim 11 (depends on 1)

The infrared absorption composition of claim 1, wherein the infrared absorption composition has a peak absorption wavelength in a wavelength region of about 800 nm to about 3000 nm.

### Claim 12 (depends on 1)

The infrared absorption composition of claim 1, wherein
n is 0 or 1 in Chemical Formula 1, or
n1 to n4 are 1 in Chemical Formula 1.

### Claim 13 (depends on 1)

The infrared absorption composition of claim 1, wherein
X1, X2, X3, and X4 are S in Chemical Formulas 2A, 2B, and 2C.

### Claim 14

A photoelectric device, comprising:
a first electrode and a second electrode facing each other, and
a photoactive layer between the first electrode and the second electrode, wherein
the photoactive layer includes a p-type semiconductor compound represented by Chemical Formula 1 and an n-type semiconductor compound,
the n-type semiconductor compound includes a compound represented by Chemical Formula 2A, a compound represented by Chemical Formula 2B, a compound represented by Chemical Formula 2C, a fullerene derivative, or a combination thereof,
wherein the p-type semiconductor compound and the n-type semiconductor compound provide a bulk heterojunction (BHJ) structure,
wherein, in Chemical Formula 1,
M is Sn, Ni, V, Al, Zn, Si, Co, or Ge,
X is a halogen,
m is an integer from 0 to 4,
n is 0 or 1,
two R1a's, two R2a's, two R3a's, and two R4a's are each the same as or different from each other and are each independently hydrogen, deuterium, a halogen, a cyano group (—CN), a C1 to C20 haloalkyl group, a C1 to C20 cyanoalkyl group, a C1 to C20 alkyl group, or a C1 to C20 alkoxy group, provided that at least one of two R1a's, at least one of two R2a's, at least one of two R3a's, and at least one of two R4a's are a C1 to C20 alkyl group or a C1 to C20 alkoxy group,
R1b, R1c, R1d, R2b, R2c, R2d, R3b, R3c, R3d, R4b, R4c and R4d are each independently hydrogen, deuterium, a halogen, a C1 to C20 haloalkyl group, a cyano group (—CN), a C1 to C20 cyanoalkyl group, a C1 to C20 alkyl group, or a C1 to C20 alkoxy group,
b is an integer of 0 to 2, and
n1, n2, n3, and n4 are each independently an integer from 1 to 4,
wherein, in Chemical Formula 2A,
Ar1 is one of the moieties represented by Chemical Formula 3,
X1 and X2 are each independently S, Se, or Te,
Ar11, Ar12, Ar21, and Ar22 are each independently a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C10 heteroaryl group,
Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, or a fused ring thereof, and
R1 and R2 are each independently hydrogen or a C1 to C10 alkyl group,
wherein, in Chemical Formula 3,
Xa and Xb are each independently S, Se, or Te,
Ra and Rb are each independently hydrogen or a C1 to C20 alkyl group, and
a and b are each independently 1 or 2,
wherein, in Chemical Formula 2B,
Ar2 is one of the moieties represented by Chemical Formula 3,
X1, X2, X3, and X4 are each independently S, Se, or Te,
Ar11, Ar12, Ar21, and Ar22 are each independently a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C10 heteroaryl group,
Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, or a fused ring thereof,
R1 and R2 are each independently hydrogen or a C1 to C10 alkyl group,
wherein, in Chemical Formula 2C
Ar3 is one of the moieties represented by Chemical Formula 4,
X1, X2, X3, and X4 are each independently S, Se, or Te,
R3 and R4 are each independently hydrogen, a C1 to C20 alkyl group, a C6 to C10 aryl group, or a C2 to C10 heteroaryl group,
Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, or a fused ring thereof, and
R1 and R2 are each independently hydrogen or a C1 to C10 alkyl group:
wherein, in Chemical Formula 4,
Y1 is CRpRq, NRr, O, S, Se, or Te, wherein Rp, Rq and Rr are each independently hydrogen or a C1 to C20 alkyl group, and
Z1 to Z4 are each independently CRs or N, wherein, Rs is hydrogen or a C1 to C20 alkyl group.

### Claim 15 (depends on 14)

The photoelectric device of claim 14, wherein the p-type semiconductor compound represented by Chemical Formula 1 is represented by one of compounds represented by Chemical Formulas 1A to 1C:
wherein, in Chemical Formulas 1A to 1C,
R1a, R1b, R1c, R1d, R2a, R2b, R2c, R2d, R3a, R3b, R3c, R3d, R4a, R4b, R4c, R4d, b, n1, n2, n3, and n4 are the same as in Chemical Formula 1,
wherein, in Chemical Formula 1C,
R5a and R5b are hydrogen, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group.

### Claim 16 (depends on 14)

The photoelectric device of claim 14, wherein in Chemical Formula 1, X is Cl.

### Claim 17 (depends on 14)

The photoelectric device of claim 14, wherein in Chemical Formula 1, two R1a's, two R2a's, two R3a's, and two R4a's are a C1 to C20 alkyl group or a C1 to C20 alkoxy group.

### Claim 18 (depends on 14)

The photoelectric device of claim 14, wherein in Chemical Formulas 2A and 2B, Ar11, Ar12, Ar21, and Ar22 are each independently:
a C6 to C10 aryl group substituted with a C1 to C20 alkyl group or a C1 to C20 alkoxy group, or
a C3 to C10 heteroaryl group substituted with a C1 to C20 alkyl group or a C1 to C20 alkoxy group.

### Claim 19 (depends on 14)

The photoelectric device of claim 14, wherein in Chemical Formulas 2A, 2B, and 2C, Ar31 and Ar32 are a cyclic group represented by one of Chemical Formulas 5A to 5F:
wherein, in Chemical Formula 5A,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
Z3 is N or CRc, wherein Rc is hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group,
R11, R12, R13, R14, and R15 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof, wherein R12, R13, R14, and R15 are each independently present or R12 and R13 and R14 and R15 are linked to each other to provide a fused aromatic ring,
n is 0 or 1, and
* is a linking position,
wherein, in Chemical Formula 5B,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
Z3 is O, S, Se, Te, or C(Ra)(CN), wherein Ra is hydrogen, a cyano group, or a C1 to C10 alkyl group,
R11 and R12 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group, or a combination thereof, and
* is a linking position,
wherein, in Chemical Formula 5C,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
R11, R12, and R13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), or a combination thereof, and
* is a linking position,
wherein, in Chemical Formula 5D,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
Z3 is N or CRc, wherein Rc is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
G1 is O, S, Se, Te, SiRxRy, or GeRzRw, wherein Rx, Ry, Rz, and Rw are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R11, R12, and R13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or a combination thereof, wherein R12 and R13 are each independently present or linked to each other to provide a fused aromatic ring,
n is 0 or 1, and
* is a linking position,
wherein, in Chemical Formula 5E,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
Z3 is N or CRc, wherein Rc is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
G2 is O, S, Se, Te, SiRxRy, or GeRzRw, wherein Rx, Ry, Rz, or Rw are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R11, R12, and R13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or a combination thereof,
n is 0 or 1, and
* is a linking position,
wherein, in Chemical Formula 5F,
Z1 and Z2 are each independently O, S, Se, Te, or CRaRb, wherein Ra and Rb are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a cyano group,
R11 is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or a combination thereof, and
G3 is O, S, Se, Te, SiRxRy, or GeRzRw, wherein Rx, Ry, Rz, and Rw are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

### Claim 20 (depends on 14)

The photoelectric device of claim 14, wherein
the compound represented by Chemical Formula 2A is a compound represented by Chemical Formula 2A-1, and
the compound represented by Chemical Formula 2B is a compound represented by Chemical Formula 2B-1:
wherein, in Chemical Formula 2A-1,
Ar1 is one of the moieties represented by Chemical Formula 3,
X1 and X2 are each independently S, Se, or Te,
R1 and R2 are each independently hydrogen or a C1 to C10 alkyl group,
R11, R12, R21, and R22 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, x1, y1, x2, and y2 are each independently an integer from 0 to 5, and
Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, or a fused ring thereof,
wherein, in Chemical Formula 2B-1,
Ar2 is one of the moieties represented by Chemical Formula 3,
X1, X2, X3, and X4 are each independently S, Se, or Te,
R11, R12, R21, and R22 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, x1, y1, x2, and y2 are each independently an integer from 0 to 5, and
Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═(CN)2, or a fused ring thereof.

### Claim 21 (depends on 14)

The photoelectric device of claim 14, wherein the fullerene derivative comprises a C60 to C120 fullerene substituted with a first functional group of an aryl group or a heterocyclic group and a second functional group of an alkyl ester group.

### Claim 22 (depends on 14)

The photoelectric device of claim 14, wherein the fullerene derivative comprises [6,6]-phenyl-C61-butyric acid methyl ester (PC60BM), bis(1-[3-(methoxycarbonyl)propyl]-1-phenyl)-[6,6]C62 (bis-PCBM), phenyl-C70-butyric acid methyl ester (PC70BM), indene-C60 bisadduct (ICBA), or indene-C60 monoadduct (ICMA).

### Claim 23 (depends on 14)

The photoelectric device of claim 14, wherein the p-type semiconductor compound and the n-type semiconductor compound are included in a volume ratio (p:n) of about 1:0.1 to about 1:10.

### Claim 24 (depends on 14)

The photoelectric device of claim 14, wherein an infrared absorption composition including the p-type semiconductor compound and the n-type semiconductor compound has a peak absorption wavelength in a wavelength region of about 800 nm to about 3000 nm.

### Claim 25 (depends on 14)

An organic sensor comprising the photoelectric device of claim 14.

### Claim 26 (depends on 25)

An electronic device comprising:
the organic sensor of claim 25.

### Claim 27 (depends on 14)

An electronic device comprising:
the photoelectric device of claim 14.