# US 9,520,571 B2 · Organic photoelectric device and image sensor

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- Number: US 9,520,571 B2
- Document ID: US9520571B2
- Status: Granted
- Kind: B2
- Application number: 13/943,834
- Filed: 2013-07-17
- Published: 2014-04-10
- Granted: 2016-12-13
- Earliest claimed: 2012-10-08
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Kwang Hee Lee; Kyu Sik Kim; Kyung Bae Park; Dong-Seok Leem; Seon-Jeong Lim
- Web page: https://patentgrep.com/patent/US9520571B2

## CPC

- H10K 85/322: {comprising boron}
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organic photoelectric device may include a first electrode and a second electrode facing each other and an active layer between the first electrode and the second electrode, the active layer including a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2. An image sensor may include the organic photoelectric device.

## Claims

### Claim 1

An organic photoelectric device comprising:
a first electrode and a second electrode facing each other; and
an active layer between the first electrode and the second electrode, the active layer including a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2:
wherein, in Chemical Formula 1,
each of R1 and R2 are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy group, and a combination thereof, and
each of R3 to R12 are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy group, a halogen atom, a halogen-containing group, and a combination thereof,
wherein, in Chemical Formula 2,
each of Ra to Rl are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen atom, a halogen-containing group, and a combination thereof, and
X is an anion.

### Claim 2 (depends on 1)

The organic photoelectric device of claim 1, wherein the compound represented by the above Chemical Formula 1 includes at least one selected from compounds represented by the following Chemical Formulae 1a to 1e:
wherein, in Chemical Formulae 1a to 1e,
each of R1 and R2 are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, and a combination thereof.

### Claim 3 (depends on 1)

The organic photoelectric device of claim 1, wherein at least one of Ra to Rl of Chemical Formula 2 includes a halogen atom.

### Claim 4 (depends on 1)

The organic photoelectric device of claim 1, wherein the compound represented by the above Chemical Formula 2 includes at least one of compounds represented by the following Chemical Formulae 2a to 2e:

### Claim 5 (depends on 1)

The organic photoelectric device of claim 1, wherein
the compound represented by the above Chemical Formula 1 is a p-type semiconductor, and
the compound represented by the above Chemical Formula 2 is an n-type semiconductor.

### Claim 6 (depends on 1)

The organic photoelectric device of claim 1, wherein the active layer selectively absorbs light at a green wavelength region.

### Claim 7 (depends on 1)

The organic photoelectric device of claim 1, wherein the active layer has a maximum absorption peak in a wavelength region of about 500 nm to about 600 nm.

### Claim 8 (depends on 1)

The organic photoelectric device of claim 1, wherein the active layer has a light-absorption curve having a full width at half maximum (FWHM) of about 50 nm to 150 nm.

### Claim 9 (depends on 1)

The organic photoelectric device of claim 1, wherein the active layer includes an intrinsic layer including the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 at a ratio of about 1:100 to about 100:1.

### Claim 10 (depends on 9)

The organic photoelectric device of claim 9, wherein the active layer includes the intrinsic layer including the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 at a ratio of about 1:10 to about 10:1.

### Claim 11 (depends on 9)

The organic photoelectric device of claim 9, wherein the active layer further comprises a p-type layer including the compound represented by the above Chemical Formula 1.

### Claim 12 (depends on 9)

The organic photoelectric device of claim 9, wherein the active layer further comprises an n-type layer including the compound represented by the above Chemical Formula 2.

### Claim 13 (depends on 9)

The organic photoelectric device of claim 9, wherein the active layer further comprises:
a p-type layer on one side of the intrinsic layer, the p-type layer including the compound represented by the above Chemical Formula 1, and
an n-type layer on the other side of the intrinsic layer, the n-type layer including the compound represented by the above Chemical Formula 2.

### Claim 14 (depends on 1)

The organic photoelectric device of claim 1, wherein the active layer comprises a p-type layer including the compound represented by the above Chemical Formula 1 and an n-type layer including the compound represented by the above Chemical Formula 2.

### Claim 15 (depends on 1)

The organic photoelectric device of claim 1, further comprising:
a charge auxiliary layer between at least one of the first electrode and the second electrode and the active layer.

### Claim 16 (depends on 1)

The organic photoelectric device of claim 1, wherein the first electrode is an anode and the second electrode is a cathode.

### Claim 17 (depends on 1)

An image sensor comprising the organic photoelectric device according to claim 1.

### Claim 18 (depends on 1)

The organic photoelectric device of claim 1, wherein
the compound represented by Chemical Formula 1 is a p-type semiconductor,
the compound represented by Chemical Formula 2 is an n-type semiconductor, and
the p-type semiconductor and the n-type semiconductor form a pn junction.
