# US 12,120,951 B2 · Infrared absorbers, infrared absorbing/blocking films and photoelectric devices and organic sensors and electronic devices

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- Number: US 12,120,951 B2
- Document ID: US12120951B2
- Status: Granted
- Kind: B2
- Application number: 17/160,860
- Filed: 2021-01-28
- Published: 2021-11-04
- Granted: 2024-10-15
- Earliest claimed: 2020-01-30
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Hwang Suk Kim; Bum Woo Park; Ohkyu Kwon; Changki Kim; In Sun Park; Dong-Seok Leem
- Web page: https://patentgrep.com/patent/US12120951B2

## CPC

- C07D 513/04: Ortho-condensed systems
- C07D 513/22: in which the condensed system contains four or more hetero rings
- C07D 517/04: Ortho-condensed systems
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 30/50: Photovoltaic [PV] devices
- H10K 39/32: Organic image sensors
- Y02E 10/549: Organic PV cells
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An infrared absorber includes a compound represented by Chemical Formula 1. An infrared absorbing/blocking film, a photoelectric device, an organic sensor, and an electronic device may include the infrared absorber. In Chemical Formula 1, Ar, X1, X2, Y1, Y2, R1, R2, R11, R12, R13, and R14 are the same as defined in the detailed description.

## Claims

### Claim 1

An infrared absorber, comprising:
a compound represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
Ar is a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted C3 to C30 heteroaromatic ring, or a combination thereof,
X1 is O, S, Se, Te, S(═O), S(═O)2, NRa1, BRa2, CRbRc, SiRdRe, GeRfRg, CRh═CRi, or CRhh═CRii, wherein
Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rh, and Ri are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
Rhh and Rii are independently
(CH)w wherein w is a positive integer, or
at least one heteroatom of O, N, S, Se, or Te, and
Rhh and Rii are linked to each other to form an aromatic ring, X2 is O, S, Se, Te, C, CRx—CRy, CRxx—CRyy, S(═O), or S(═O2), wherein
Rx and Ry are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
Rxx and Ryy are independently
(CH)v wherein v is a positive integer, or
at least one heteroatom of O, N, S, Se, or Te, and
Rxx and Ryy are linked to each other to form an aromatic ring,
Y1 and Y2 are independently O, S, Se, Te, S(═O), S(═O)2, NRp, or SiRqRr, wherein Rp, Rq and Rr are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a halogen, or a cyano group,
R1 and R2 are independently hydrogen, deuterium, or a C1 to C10 alkyl group,
one of R11 and R12 is a substituted or unsubstituted C1 to C40 alkoxy group and another of R11 and R12 is an electron donating heteroaromatic ring group, and
one of R13 and R14 is a substituted or unsubstituted C1 to C40 alkoxy group and another of R13 and R14 is an electron donating heteroaromatic ring group.

### Claim 2 (depends on 1)

The infrared absorber of claim 1, wherein
in Chemical Formula 1, Ar is a benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetracene ring, a substituted or unsubstituted pyrene ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted quinazoline ring, or a substituted or unsubstituted phenanthroline ring.

### Claim 3 (depends on 1)

The infrared absorber of claim 1, wherein Ar is one moiety of a set of moieties represented by Chemical Formula A-1, each moiety including at least one aromatic ring and left and right linking groups:
wherein, in Chemical Formula A-1,
hydrogen of each aromatic ring is not replaced or is replaced by deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a —SiH3 group, or a C1 to C10 alkylsilyl group,
separate adjacent pairs of *'s inside the at least one aromatic ring are linking portions with separate, respective ones of an N—X1—N-containing ring of Chemical Formula 1 or an N═X2═N-containing ring of Chemical Formula 1, and
*'s of the left and right linking groups are portions linked to separate, respective ones of a Y1-containing ring of Chemical Formula 1 or a Y2-containing ring of Chemical Formula 1.

### Claim 4 (depends on 1)

The infrared absorber of claim 1, wherein
in Chemical Formula 1, Ar is one moiety of a set of moieties represented by Chemical Formula A-2, each moiety including at least one aromatic ring and left and right linking groups:
wherein, in Chemical Formula A-2,
hydrogen of each aromatic ring is not replaced or is replaced by deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a —SiH3 group, or a C1 to C10 alkylsilyl group,
separate adjacent pairs of *'s inside the at least one aromatic ring are linking portions with separate, respective ones of an N—X1—N-containing ring of Chemical Formula 1 or an N═X2═N-containing ring of Chemical Formula 1, and
*'s of the left and right linking groups are portions linked to separate, respective ones of a Y1-containing ring of Chemical Formula 1 or a Y2-containing ring of Chemical Formula 1.

### Claim 5 (depends on 1)

The infrared absorber of claim 1, wherein
in Chemical Formula 1, X2 is CRxx—CRyy, Rxx and Ryy are linked to establish an aromatic ring, wherein the aromatic ring is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted acenaphthene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetracene ring, a substituted or unsubstituted pyrene ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted quinazoline ring, a substituted or unsubstituted phenanthroline ring, a substituted or unsubstituted pyrimidine ring, or a substituted or unsubstituted benzodithiophene ring.

### Claim 6 (depends on 1)

The infrared absorber of claim 1, wherein in Chemical Formula 1, X2 is CRxx—CRyy, Rxx and Ryy are linked to establish an aromatic ring, wherein the aromatic ring is one moiety of a set of moieties represented by Chemical Formula B-1 and Chemical Formula B-2, each moiety including at least one aromatic ring:
wherein, in Chemical Formula B-1,
hydrogen of each aromatic ring is not replaced or is replaced by a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, a C6 to C20 aryl group, or a C3 to C20 heteroaryl group, and
*'s inside the at least one aromatic ring are linking portions with a carbon of CRxx—CRyy, wherein, in Chemical Formula B-2,
hydrogen of each aromatic ring is not replaced or is replaced by a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, a C6 to C20 aryl group, or a C3 to C20 heteroaryl group, and
*'s inside the at least one aromatic ring are linking portions with a carbon of CRxx—CRyy.

### Claim 7 (depends on 1)

The infrared absorber of claim 1, wherein in Chemical Formula 1, X2 is CRxx—CRyy, Rxx and Ryy are linked to establish an aromatic ring, wherein the aromatic ring is one moiety of a set of moieties represented by Chemical Formula B-3-1 or a set of moieties represented by Chemical Formula B-3-2, each moiety including at least one aromatic ring:
wherein, in Chemical Formulas B-3-1 and B-3-2,
Ar11 and Ar12 are independently a substituted or unsubstituted C6 to C30 arene group or a substituted or unsubstituted C3 to C30 heteroarene group,
in Chemical Formula B-3-1, Z1 and Z2 are independently CRa or N, wherein Ra is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C10 arylamine group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
*'s inside the at least one aromatic ring are linking portions with a carbon of CRxx—CRyy.

### Claim 8 (depends on 7)

The infrared absorber of claim 7, wherein
one moiety of the set of moieties represented by Chemical Formula B-3-1 is one moiety of a set of moieties represented by Chemical Formula B-3-11, and
one moiety of the set of moieties represented by Chemical Formula B-3-2 is one moiety of a set of moieties represented by Chemical Formula B-3-21, each moiety including at least one aromatic ring:
wherein, in Chemical Formula B-3-11,
hydrogen of each aromatic ring is not replaced or is replaced by a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, a C6 to C20 aryl group, or a C3 to C20 heteroaryl group, and
*'s inside the at least one aromatic ring are linking portions with a carbon of CRxx—CRyy, wherein, in Chemical Formula B-3-21,
hydrogen of each aromatic ring is not replaced or is replaced by deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, a C6 to C20 aryl group, or a C3 to C20 heteroaryl group,
*'s inside the at least one aromatic ring are linking portions with a carbon of CRxx—CRyy, and
Xa and Xb are independently —O—, —S—, —Se—, —Te—, —NRa—, —SiRbRc—, or —GeRdRe—, wherein Ra, Rb, Rc, Rd, and Re are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group.

### Claim 9 (depends on 1)

The infrared absorber of claim 1, wherein in Chemical Formula 1, the electron donating heteroaromatic ring group is one moiety of a set of moieties represented by Chemical Formula C:
wherein, in Chemical Formula C,
Z1, Z2, and Z3 are independently O, S, Se, Te, S(═O), S(═O)2, NRa1, BRa2, SiRbRc, GeRdRe, or PRf, wherein Ra1, Ra2, Rb, Rc, Rd, Re, and Rf are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
Rb and Rc are independently present or are linked to each other to provide a ring,
Rd and Re are independently present or are linked to each other to provide a ring,
hydrogen of each aromatic ring is not replaced or is replaced by deuterium, a halogen, a cyano group, a C1 to C12 alkyl group, a C1 to C12 haloalkyl group, a C1 to C12 alkoxy group, a —SiH3 group, a C1 to C12 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C14 aryl group, or a C3 to C12 heteroaryl group, and
* is a linking point with Chemical Formula 1.

### Claim 10 (depends on 9)

The infrared absorber of claim 9, wherein hydrogen of each aromatic ring of Chemical Formula C is replaced by at least one arylamine group, and the arylamine group is represented by Chemical Formula D-1:
wherein, in Chemical Formula D-1,
Ar5 and Ar6 are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group, and
* is a linking point with Chemical Formula C.

### Claim 11 (depends on 9)

The infrared absorber of claim 9, wherein hydrogen of each aromatic ring of Chemical Formula C is replaced by at least one N-containing heterocyclic group, and the N-containing heterocyclic group is represented by Chemical Formula D-2:
wherein, in Chemical Formula D-2,
Ar7 and Ar8 are independently a substituted or unsubstituted C6 to C30 arene group or a substituted or unsubstituted C3 to C30 heteroarene group,
G is a single bond, —O—, —S—, —Se—, —Te—, —N═, —NRa—, —SiRbRc—, —GeRdRe—, —(CRfRg)n—, or —(C(Rh)═C(Ri))—, wherein Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, and Ri are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, Rb and Rc, Rd and Re, Rf and Rg, or Rh and Ri are independently present or are linked to each other to establish a ring, and n of —(CRfRg)n— is an integer of 1 or 2, and
* is a linking point with Chemical Formula C.

### Claim 12 (depends on 10)

The infrared absorber of claim 10, wherein Chemical Formula D-1 is represented by Chemical Formula D-1a or Chemical Formula D-1b:
wherein, in Chemical Formula D-1a,
Z1 to Z10 are independently N or CRa, wherein Ra is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z1 to Z10 are CRa, Ra is independently present or adjacent two of Z1 to Z10 are linked to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula C,
wherein, in Chemical Formula D-1b,
Xa and Xb are independently —O—, —S—, —Se—, —Te—, —NRa—, —SiRbRc—, or —GeRdRe—, wherein Ra, Rb, Rc, Rd, and Re are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,
Z1 to Z6 are independently N or CRx, wherein Rx is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z1 to Z6 are CRx, Rx is independently present or adjacent two of Z1 to Z6 are linked to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula C.

### Claim 13 (depends on 11)

The infrared absorber of claim 11, wherein Chemical Formula D-2 is represented by Chemical Formula D-2a, Chemical Formula D-2b, or Chemical Formula D-2c:
wherein, in Chemical Formula D-2a,
G is a single bond, —O—, —S—, —Se—, —Te—, —N═, —NRa—, —SiRbRc—, —GeRdRe—, —(CRfRg)n—, or —(C(Rh)═C(Ri))—, wherein Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, and Ri are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, Rb and Rc, Rd and Re, Rf and Rg, or Rh and Ri are independently present or are linked to each other to establish a ring, and n of —(CRfRg)n— is an integer of 1 or 2,
Z1 to Z8 are independently N or CRx, wherein Rx is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z1 to Z8 are CRx, Rx is independently present or adjacent two of Z1 to Z8 are linked to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula C,
wherein, in Chemical Formulas D-2b and D-2c,
G is a single bond, —O—, —S—, —Se—, —Te—, —N═, —NRa—, —SiRbRc—, —GeRdRe—, —(CRfRg)n—, or —(C(Rh)═C(Ri))—, wherein Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, and Ri are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, Rb and Rc, Rd and Re, Rf and Rg, or Rh and Ri are independently present or are linked to each other to establish a ring, and n of —(CRfRg)n— is an integer of 1 or 2,
Xa and Xb are independently —O—, —S—, —Se—, —Te—, —NRp—, —SiRqRr—, or —GeRsRt—, wherein Rp, Rq, Rr, Rs, and Rt are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,
Z1 to Z4 are independently N or CRx, wherein Rx is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z1 to Z4 are CRx, Rx is independently present or adjacent two of Z1 to Z4 are linked to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula C.

### Claim 14 (depends on 1)

The infrared absorber of claim 1, wherein the infrared absorber has a peak absorption wavelength in a wavelength region of about 750 nm to about 3000 nm.

### Claim 15 (depends on 1)

An infrared absorbing/blocking film comprising the infrared absorber of claim 1.

### Claim 16

A photoelectric 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 includes an infrared absorber that includes a compound represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
Ar is a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted C3 to C30 heteroaromatic ring, or a combination thereof,
X1 is O, S, Se, Te, S(═O), S(═O)2, NRa1, BRa2, CRbRc, SiRdRe, GeRfRg, CRh═CRi, or CRhh═CRii, wherein
Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rh, and Ri are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
Rhh and Rii are independently
(CH)w wherein w is a positive integer, or
at least one heteroatom of O, N, S, Se, or Te, and
Rhh and Rii are linked to each other to form an aromatic ring, X2 is O, S, Se, Te, C, CRx—CRy, CRxx—CRyy, S(═O), or S(═O2), wherein
Rx and Ry are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
Rxx and Ryy are independently
(CH)v wherein v is a positive integer, or
at least one heteroatom of O, N, S, Se, or Te, and
Rxx and Ryy are linked to each other to form an aromatic ring,
Y1 and Y2 are independently O, S, Se, Te, S(═O), S(═O)2, NRp, or SiRqRr, wherein Rp, Rq and Rr are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a halogen, or a cyano group),
R1 and R2 are independently hydrogen, deuterium or a C1 to C10 alkyl group,
one of R11 and R12 is a substituted or unsubstituted C1 to C40 alkoxy group and another of R11 and R12 is an electron donating heteroaromatic ring group, and
one of R13 and R14 is a substituted or unsubstituted C1 to C40 alkoxy group and another of R13 and R14 is an electron donating heteroaromatic ring group.

### Claim 17 (depends on 16)

The photoelectric device of claim 16, wherein in Chemical Formula 1, Ar is a benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetracene ring, a substituted or unsubstituted pyrene ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted quinazoline ring, or a substituted or unsubstituted phenanthroline ring.

### Claim 18 (depends on 16)

The photoelectric device of claim 16, wherein Ar is one moiety of a set of moieties represented by Chemical Formula A-1, each moiety including at least one aromatic ring and left and right linking groups:
wherein, in Chemical Formula A-1,
hydrogen of each aromatic ring is not replaced or is replaced by deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a —SiH3 group, or a C1 to C10 alkylsilyl group,
separate adjacent pairs of *'s inside the at least one aromatic ring are linking portions with separate, respective ones of an N—X1—N-containing ring of Chemical Formula 1 or an N═X2═N-containing ring of Chemical Formula 1, and
*'s of the left and right linking groups are portions linked to separate, respective ones of a Y1-containing ring of Chemical Formula 1 or a Y2-containing ring of Chemical Formula 1.

### Claim 19 (depends on 16)

The photoelectric device of claim 16, wherein in Chemical Formula 1, Ar is one moiety of a set of moieties represented by Chemical Formula A-2, each moiety including at least one aromatic ring and left and right linking groups:
wherein, in Chemical Formula A-2,
hydrogen of each aromatic ring is not replaced or is replaced by deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a —SiH3 group, or a C1 to C10 alkylsilyl group,
separate adjacent pairs of *'s inside the at least one aromatic ring are linking portions with separate, respective ones of an N—X1—N-containing ring of Chemical Formula 1 or an N═X2═N-containing ring of Chemical Formula 1, and
*'s of the left and right linking groups are portions linked to separate, respective ones of a Y1-containing ring of Chemical Formula 1 or a Y2-containing ring of Chemical Formula 1.

### Claim 20 (depends on 16)

The photoelectric device of claim 16, wherein
in Chemical Formula 1, X2 is CRxx—CRyy, Rxx and Ryy are linked to establish an aromatic ring, wherein the aromatic ring is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted acenaphthene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetracene ring, a substituted or unsubstituted pyrene ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted quinazoline ring, a substituted or unsubstituted phenanthroline ring, a substituted or unsubstituted pyrimidine ring, or a substituted or unsubstituted benzodithiophene ring.

### Claim 21 (depends on 16)

The photoelectric device of claim 16, wherein in Chemical Formula 1, X2 is CRxx—CRyy, Rxx and Ryy are linked to establish an aromatic ring, wherein the aromatic ring is one moiety of a set of moieties represented by Chemical Formula B-1 and Chemical Formula B-2, each moiety including at least one aromatic ring:
wherein, in Chemical Formula B-1,
hydrogen of each aromatic ring is not replaced or is replaced by a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, a C6 to C20 aryl group, or a C3 to C20 heteroaryl group, and
*'s inside the at least one aromatic ring are linking portions with a carbon of CRxx—CRyy,
wherein, in Chemical Formula B-2,
hydrogen of each aromatic ring is not replaced or is replaced by a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, a C6 to C20 aryl group, or a C3 to C20 heteroaryl group, and
*'s inside the at least one aromatic ring are linking portions with a carbon of CRxx—CRyy.

### Claim 22 (depends on 16)

The photoelectric device of claim 16, wherein in Chemical Formula 1, X2 is CRxx—CRyy, Rxx and Ryy are linked to establish an aromatic ring, wherein the aromatic ring is one moiety of a set of moieties represented by Chemical Formula B-3-1 or a set of moieties represented by Chemical Formula B-3-2, each moiety including at least one aromatic ring:
wherein, in Chemical Formulas B-3-1 and B-3-2,
Ar11 and Ar12 are independently a substituted or unsubstituted C6 to C30 arene group or a substituted or unsubstituted C3 to C30 heteroarene group,
in Chemical Formula B-3-1, Z1 and Z2 are independently CRa or N, wherein Ra is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C10 arylamine group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof, and
*'s inside the at least one aromatic ring are linking portions with a carbon of CRxx—CRyy.

### Claim 23 (depends on 22)

The photoelectric device of claim 22, wherein
one moiety of the set of moieties represented by Chemical Formula B-3-1 is one moiety of a set of moieties represented by Chemical Formula B-3-11, each moiety including at least one aromatic ring, and
one moiety of the set of moieties represented by Chemical Formula B-3-2 is one moiety of a set of moieties represented by Chemical Formula B-3-21, each moiety including at least one aromatic ring:
wherein, in Chemical Formulas B-3-11,
hydrogen of each aromatic ring is not replaced or is replaced by a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, a C6 to C20 aryl group, or a C3 to C20 heteroaryl group, and
*'s inside the at least one aromatic ring are linking portions with a carbon of CRxx—CRyy,
wherein, in Chemical Formula B-3-21,
hydrogen of each aromatic ring is not replaced or is replaced by deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, a C6 to C20 aryl group, or a C3 to C20 heteroaryl group,
*'s inside the at least one aromatic ring are linking portions with a carbon of CRxx—CRyy, and
Xa and Xb are independently —O—, —S—, —Se—, —Te—, —NRa—, —SiRbRc—, or —GeRdRe—, wherein Ra, Rb, Re, Rd, and Re are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group.

### Claim 24 (depends on 16)

The photoelectric device of claim 16, wherein in Chemical Formula 1, the electron donating heteroaromatic ring group is one moiety of a set of moieties represented by Chemical Formula C:
wherein, in Chemical Formula C,
Z1, Z2, and Z3 are independently O, S, Se, Te, S(═O), S(═O)2, NRa1, BRa2, SiRbRc, GeRdRe, or PRf, wherein Ra1, Ra2, Rb, Rc, Rd, Re and Rf are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
Rb and Rc are independently present or are linked to each other to provide a ring,
Rd and Re are independently present or are linked to each other to provide a ring,
hydrogen of each aromatic ring is not replaced or is replaced by deuterium, a halogen, a cyano group, a C1 to C12 alkyl group, a C1 to C12 haloalkyl group, a C1 to C12 alkoxy group, a —SiH3 group, a C1 to C12 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C14 aryl group, or a C3 to C12 heteroaryl group, and
*is a linking point with Chemical Formula 1.

### Claim 25 (depends on 24)

The photoelectric device of claim 24, wherein hydrogen of each aromatic ring of Chemical Formula C is replaced by at least one arylamine group, and the arylamine group is represented by Chemical Formula D-1:
wherein, in Chemical Formula D-1,
Ar5 and Ar6 are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group, and
* is a linking point with Chemical Formula C.

### Claim 26 (depends on 24)

The photoelectric device of claim 24, wherein hydrogen of each aromatic ring of Chemical Formula C is replaced by at least one N-containing heterocyclic group, and the N-containing heterocyclic group is represented by Chemical Formula D-2:
wherein, in Chemical Formula D-2,
Ar7 and Ar8 are independently a substituted or unsubstituted C6 to C30 arene group or a substituted or unsubstituted C3 to C30 heteroarene group,
G is a single bond, —O—, —S—, —Se—, —Te—, —N═, —NRa—, —SiRbRc—, —GeRdRe—, —(CRfRg)n—, or —(C(Rh)═C(Ri))—, wherein Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, and Ri are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, Rb and Rc, Rd and Re, Rf and Rg, or Rh and Ri are independently present or are linked to each other to establish a ring, and n of —(CRfRg)n— is an integer of 1 or 2, and
* is a linking point with Chemical Formula C.

### Claim 27 (depends on 25)

The photoelectric device of claim 25, wherein Chemical Formula D-1 is represented by Chemical Formula D-1a or Chemical Formula D-1b:
wherein, in Chemical Formula D-1a,
Z1 to Z10 are independently N or CRa, wherein Ra is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z1 to Z10 are CRa, Ra is independently present or adjacent two of Z1 to Z10 are linked to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula C,
wherein, in Chemical Formula D-1b,
Xa and Xb are independently —O—, —S—, —Se—, —Te—, —NRa—, —SiRbRc—, or —GeRdRe—, wherein Ra, Rb, Rc, Rd, and Re are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,
Z1 to Z6 are independently N or CRx, wherein Rx is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z1 to Z6 are CRx, Rx is independently present or adjacent two of Z1 to Z6 are linked to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula C.

### Claim 28 (depends on 26)

The photoelectric device of claim 26, wherein Chemical Formula D-2 is represented by Chemical Formula D-2a, Chemical Formula D-2b, or Chemical Formula D-2c:
wherein, in Chemical Formula D-2a,
G is a single bond, —O—, —S—, —Se—, —Te—, —N═, —NRa—, —SiRbRc—, —GeRdRe—, —(CRfRg)n—, or —(C(Rh)═C(Ri))—, wherein Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, and Ri are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, Rb and Rc, Rd and Re, Rf and Rg, or Rh and Ri are independently present or are linked to each other to establish a ring, and n of —(CRfRg)n— is an integer of 1 or 2,
Z1 to Z8 are independently N or CRx, wherein Rx is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z1 to Z8 are CRx, Rx is independently present or adjacent two of Z1 to Z8 are linked to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula C,
wherein, in Chemical Formulas D-2b and D-2c,
G is a single bond, —O—, —S—, —Se—, —Te—, —N═, —NRa—, —SiRbRc—, —GeRdRe—, —(CRfRg)n—, or —(C(Rh)═C(Ri))—, wherein Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, and Ri are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, Rb and Rc, Rd and Re, Rf and Rg, or Rh and Ri are independently present or are linked to each other to establish a ring, and n of —(CRfRg)n— is an integer of 1 or 2,
Xa and Xb are independently —O—, —S—, —Se—, —Te—, —NRp—, —SiRqRr—, or —GeRsRt—, wherein Rp, Rq, Rr, Rs, and Rt are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,
Z1 to Z4 are independently N or CRx, wherein Rx is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH3, a C1 to C10 alkylsilyl group, —NH2, a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z1 to Z4 are CRx, Rx is independently present or adjacent two of Z1 to Z4 are linked to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula C.

### Claim 29 (depends on 16)

The photoelectric device of claim 16, wherein the organic layer further includes fullerene.

### Claim 30 (depends on 16)

The photoelectric device of claim 16, wherein the infrared absorber has a peak absorption wavelength in a wavelength region of about 750 nm to about 3000 nm.

### Claim 31 (depends on 16)

An organic sensor comprising the photoelectric device of claim 16.

### Claim 32 (depends on 31)

An electronic device comprising the organic sensor of claim 31.

### Claim 33 (depends on 16)

An electronic device comprising the photoelectric device of claim 16.