Compounds for infrared light sensing devices, infrared light sensing devices, image sensors, and electronic devices including the same

Patent metadata

Field	Value
Publication number	US-10950800-B2
Application number	US-201815962230-A
Country	US
Kind code	B2
Filing date	Apr 25, 2018
Priority date	Apr 26, 2017
Publication date	Mar 16, 2021
Grant date	Mar 16, 2021

Abstract

A compound for an infrared light sensing device may be represented by a particular chemical formula and may be included in an infrared light sensing device. An image sensor may include the infrared light sensing device, and an electronic device may include the image sensor.

First claim

What is claimed is:

1. A compound for an infrared light sensing device,
the compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Y 1 to Y 6 are independently
a substituted or unsubstituted pentagonal ring including one of O, S, and Se, or
a fused ring of two or more substituted or unsubstituted pentagonal rings including one of O, S, and Se,

k, l, m, and n are independently 0 or 1, and
R a and R b are independently hydrogen or a monovalent organic group,

wherein the compound has a maximum absorption wavelength (λmax) in a wavelength range of greater than or equal to about 700 nm and less than or equal to about 1,400 nm in a thin film state, provided that,
when k, l, m, and n are all 0, Y 2 and Y 5 are independently represented by Chemical Formula 2 or Chemical Formula 3:

wherein, in Chemical Formulae 2 and 3,
X 1 is O,
X 2 and X 3 are independently O or Se,
R 1 to R 4 are independently hydrogen or a monovalent organic group, and
* is a linking point.

2. The compound of claim 1 , wherein, in Chemical Formula 1, R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a hydroxy group, a halogen atom, or a combination thereof.

3. The compound of claim 1 , wherein the compound is represented by one of Chemical Formulae 4 to 7:

wherein, in Chemical Formulae 4 to 7,
X 4 and X 5 are O,
X 6 to X 11 are independently one of O, S, and Se,
R c and R d are independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a hydroxy group, a halogen atom, or a combination thereof, and
R 5 to R 12 are independently hydrogen or a monovalent organic group.

4. The compound of claim 1 , wherein the compound is an n-type semiconductor compound.

5. An infrared light sensing device configured to sense light in an infrared wavelength region, the infrared light sensing device comprising:
an upper electrode and a lower electrode facing each other; and
an infrared light absorption layer between the upper electrode and the lower electrode, the infrared light absorption layer including a compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Y 1 to Y 6 are independently
a substituted or unsubstituted pentagonal ring including one of O, S, and Se, or
a fused ring of two or more substituted or unsubstituted pentagonal rings including one of O, S, and Se,

k, l, m, and n are independently 0 or 1, and
R a and R b are independently hydrogen or a monovalent organic group,

wherein the compound has a maximum absorption wavelength (λ max ) in a wavelength range of greater than or equal to about 700 nm and less than or equal to about 1,400 nm in a thin film state, provided that,
when k, l, m, and n are all 0, Y 2 and Y 5 are independently represented by Chemical Formula 2 or Chemical Formula 3:

wherein, in Chemical Formulae 2 and 3,
X 1 is O,
X 2 and X 3 are independently O or Se,
R 1 to R 4 are independently hydrogen or a monovalent organic group, and
* is a linking point.

6. The infrared light sensing device of claim 5 , wherein in Chemical Formula 1, R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a hydroxy group, a halogen atom, or a combination thereof.

7. The infrared light sensing device of claim 5 , wherein the compound is represented by one of Chemical Formulae 4 to 7:

wherein, in Chemical Formulae 4 to 7,
X 4 and X 5 are O,
X 6 to X 11 are independently one of O, S, and Se,
R c and R d are independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a hydroxy group, a halogen atom, or a combination thereof, and
R 5 to R 12 are independently hydrogen or a monovalent organic group.

8. The infrared light sensing device of claim 5 , wherein the compound is an n-type semiconductor compound.

9. An image sensor, comprising:
the infrared light sensing device of claim 5 , and
a visible light sensing device including at least one of a blue photo-sensing device configured to sense light in a blue wavelength region, a red photo-sensing device configured to sense light in a red wavelength region, and a green photo-sensing device configured to sense light in a green wavelength region.

10. The image sensor of claim 9 , wherein,
the blue wavelength region is associated with a maximum absorption wavelength (λ max ) of greater than or equal to about 400 nm and less than 500 nm,
the red wavelength region is associated with a maximum absorption wavelength (λ max ) of greater than 580 nm and less than about 700 nm,
the green wavelength region is associated with a maximum absorption wavelength (λ max ) of about 500 nm to about 580 nm, and
the infrared wavelength region has a maximum absorption wavelength (λ max ) of about 700 nm to about 1,400 nm.

11. The image sensor of claim 9 , wherein the visible light sensing device and the infrared light sensing device are stacked vertically.

12. The image sensor of claim 9 , wherein the visible light sensing device and the infrared light sensing device are in parallel horizontally.

13. An electronic device comprising the image sensor of claim 9 .

14. The electronic device of claim 13 , wherein the electronic device includes a mobile phone, a digital camera, or a biometric camera.

Assignees

• Samsung Electronics Co Ltd
• Imperial Innovations Ltd

Inventors

• Han Moon Gyu
• Park Kyung Bae
• Jin Yong Wan
• Heo Chul Joon
• Baatz Brett
• Heeney Martin
• Suh Minwon
• Han Yang
• Kim Ji-Seon

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K30/30

  comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title