Compound for organic photoelectric device and organic photoelectric device, image sensor and electronic device including the same

Patent metadata

Field	Value
Publication number	US-9941477-B2
Application number	US-201615358726-A
Country	US
Kind code	B2
Filing date	Nov 22, 2016
Priority date	Nov 24, 2015
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

A compound for an organic photoelectric device is represented by Chemical Formula 1, and an organic photoelectric device, an image sensor and an electronic device include the same.

First claim

What is claimed is:

1. A compound for an organic photoelectric device represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,
X 1 is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b , wherein each of R a and R b is one of hydrogen and a C 1 to C 10 alkyl group,
X 2 is one of O, S, Se, Te, and C(R c )(CN), wherein R c is one of hydrogen, a cyano group (—CN), and a C 1 to C 10 alkyl group,
each of Ar 1 and Ar 2 is independently one of a substituted or unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 4 to C 30 heteroaryl group, and
each of R 1 to R 5 is independently one of hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 4 to C 30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof.

2. The compound of claim 1 , wherein each of the Ar 1 and Ar 2 is independently one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted benzotriazinyl group, a substituted or unsubstituted pyridopyrazinyl group, a substituted or unsubstituted pyridopyrimidinyl group, and a substituted or unsubstituted pyridopyridazinyl group.

3. The compound of claim 1 , wherein at least one of the Ar 1 and Ar 2 is one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted benzotriazinyl group, a substituted or unsubstituted pyridopyrazinyl group, a substituted or unsubstituted pyridopyrimidinyl group, and a substituted or unsubstituted pyridopyridazinyl group.

4. The compound of claim 1 , wherein the compound has a maximum absorption wavelength (λ max ) of about 500 nm to about 600 nm in a thin film state.

5. The compound of claim 1 , wherein the compound has a maximum absorption wavelength (λ max ) of about 525 nm to about 560 nm in a thin film state.

6. The compound of claim 1 , wherein the compound exhibits a light absorption curve having a full width at half maximum (FWHM) of about 50 nm to about 120 nm in a thin film state.

7. The compound of claim 1 , wherein a difference between a melting point and a deposition temperature of the compound is greater than or equal to about 5° C.

8. The compound of claim 1 , wherein a difference between a melting point and a deposition temperature of the compound is greater than or equal to about 30° C.

9. The compound of claim 1 , wherein a difference between a melting point and a deposition temperature of the compound is greater than or equal to about 50° C.

10. 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 the compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
X 1 is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b , wherein each of R a and R b is one of hydrogen and a C 1 to C 10 alkyl group,
X 2 is one of O, S, Se, Te, and C(R c )(CN), wherein R c is one of hydrogen, a cyano group (—CN), and a C 1 to C 10 alkyl group,
each of Ar 1 and Ar 2 is independently one of a substituted or unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 4 to C 30 heteroaryl group, and
each of R 1 to R 5 is independently one of hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 4 to C 30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and combination thereof.

11. The organic photoelectric device of claim 10 , wherein each of the Ar 1 and Ar 2 is independently one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted benzotriazinyl group, a substituted or unsubstituted pyridopyrazinyl group, a substituted or unsubstituted pyridopyrimidinyl group, and a substituted or unsubstituted pyridopyridazinyl group.

12. The organic photoelectric device of claim 10 , wherein at least one of the Ar 1 and Ar 2 is one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted benzotriazinyl group, a substituted or unsubstituted pyridopyrazinyl group, a substituted or unsubstituted pyridopyrimidinyl group, and a substituted or unsubstituted pyridopyridazinyl group.

13. The organic photoelectric device of claim 10 , wherein the active layer has a maximum absorption wavelength (λ max ) of about 500 nm to about 600 nm.

14. The organic photoelectric device of claim 10 , wherein the active layer has a maximum absorption wavelength (λ max ) of about 525 nm to about 560 nm.

15. The organic photoelectric device of claim 10 , wherein the active layer exhibits a light absorption curve having a full width at half maximum (FWHM) of about 50 nm to about 120 nm.

16. The organic photoelectric device of claim 10 , wherein a difference between a melting point and a deposition temperature of the compound is greater than or equal to about 5° C.

17. An image sensor comprising the organic photoelectric device of claim 10 .

18. The image sensor of claim 17 , further

Assignees

• Samsung Electronics Co Ltd

Inventors

• Choi Hyesung
• Yagi Tadao
• Sakurai Rie
• Lee Gae Hwang
• Lim Seon-Jeong
• Bulliard Xavier
• Yun Sung Young
• Leem Dong-Seok

Classifications

• C07D421/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D409/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/006

  Electricity · mapped topic