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

Patent metadata

Field	Value
Publication number	US-10224486-B2
Application number	US-201615272580-A
Country	US
Kind code	B2
Filing date	Sep 22, 2016
Priority date	Sep 25, 2015
Publication date	Mar 5, 2019
Grant date	Mar 5, 2019

Abstract

A compound for an organic photoelectric device is represented by Chemical Formula 1. An organic photoelectric device includes a first electrode and a second electrode facing each other, and an active layer including the compound represented by Chemical Formula 1 between the first electrode and the second electrode.

First claim

What is claimed is:

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

wherein, in Chemical Formula 1,
each of Ar 1 and Ar 2 are 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,
X is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b (wherein each of R a and R b are independently one of hydrogen, a C 1 to C 10 alkyl group, a C 6 to C 10 aryl group, and a C 5 to C 10 heteroaryl group),
each of R 1 to R 6 are independently one of hydrogen, 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, and CN,
each of p and q are independently integers of 0 to 4,
r is an integer of 0 to 2,
n is 0 or 1, and
each of Ph 1 and Ph 2 are independently a fused phenylene ring, provided that at least one of Phi and Ph 2 are present.

2. The compound of claim 1 , wherein at least one of Ar 1 and Ar 2 is one of a naphthyl group and an anthracenyl group.

3. The compound of claim 1 , wherein the compound has a maximum absorption wavelength (λ max ) of about 500 nm to about 600 nm.

4. The compound of claim 1 , wherein the compound has a maximum absorption wavelength (λ max ) of about 530 nm to about 570 nm.

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

6. The compound of claim 1 , wherein the compound is a p-type semiconductor compound.

7. The compound of claim 6 , wherein the compound exhibits a light absorption curve having a full width at half maximum (FWHM) in a thin film state of about 50 nm to about 110 nm.

8. 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 Chemical Formula 1:

wherein in Chemical Formula 1,
each of Ar 1 and Ar 2 are 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,
X is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b (wherein each of R a and R b are independently one of hydrogen, a C 1 to C 10 alkyl group, a C 6 to C 10 aryl group, and a C 5 to C 10 heteroaryl group),
each of R 1 to R 6 are independently one of hydrogen, 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, and CN,
each of p and q are independently integers of 0 to 4,
r is an integer of 0 to 2,
n is 0 or 1, and
each of Ph 1 and Ph 2 are independently a fused phenylene ring, provided that at least one of Ph 1 and Ph 2 are present.

9. The organic photoelectric device of claim 8 , wherein the active layer has an absorption coefficient of greater than or equal to about 6×10 4 cm −1 when including the compound and C 60 in a volume ratio of about 0.9:1 to about 1.1:1.

10. The organic photoelectric device of claim 8 , wherein the active layer has an absorption coefficient of about 6×10 4 cm −1 to about 6.7×10 4 cm −1 when including the compound and C 60 in a volume ratio of about 0.9:1 to about 1.1:1.

11. The organic photoelectric device of claim 8 , wherein the active layer has a maximum absorption wavelength (λ max ) of about 500 nm to about 600 nm.

12. The organic photoelectric device of claim 8 , wherein the active layer has a maximum absorption wavelength (λ max ) of about 530 nm to about 570 nm.

13. The organic photoelectric device of claim 8 , wherein the active layer exhibits a light absorption curve having a full width at half maximum (FWHM) in a thin film state of about 50 nm to about 120 nm.

14. The organic photoelectric device of claim 8 , wherein the active layer exhibits a light absorption curve having a full width at half maximum (FWHM) in a thin film state of about 50 nm to about 110 nm.

15. The organic photoelectric device of claim 8 , wherein the compound is a p-type semiconductor compound.

16. The organic photoelectric device of claim 15 , wherein the active layer further comprises an n-type semiconductor compound.

17. The organic photoelectric device of claim 16 , wherein the n-type semiconductor compound includes one of sub-phthalocyanine, fullerene or a fullerene derivative, thiophene or a thiophene derivative, and a combination thereof.

18. An image sensor including the organic photoelectric device of claim 8 .

19. The image sensor of claim 18 , further comprising:
a semiconductor substrate integrated with a plurality of first photo-sensing devices configured to sense light in a blue wavelength region and a plurality of second photo-sensing devices configured to sense light in a red wavelength region, wherein the organic photoelectric device is on the semiconductor substrate and is configured to selectively absorb light in a green wavelength region.

20. The image sensor of claim 19 , wherein the plurality of first photo-sensing devices and the plurality of second photo-sensing devices are stacked in a vertical direction on the semiconductor substrate.

21. The image sensor of claim 19 , further comprising:
a color filter layer between the semiconductor substrate and the organic photoelectric device, the color filter layer including a blue filter configured to selectively absorb light in a blue wavelength region and a red filter configured to selectively absorb light in a red wavelength region.

22. The image sensor of claim 18 , wherein
the organic photoelectric device is a green photoelectric device, and
the green photoelectric device, a blue photoelectric device configured to selectively absorb light in a blue wavelength region, and a red photoelectric device configured to selectively absorb light in a red wavelength region are stacked.

23. An electronic device comprising the image sensor of claim 18 .

Assignees

• Samsung Electronics Co Ltd

Inventors

• Yagi Tadao
• Sakurai Rie
• Choi Hyesung
• IMASE Tatsuya
• Shibuya Hiromasa
• Yun Sung Young
• Lee Gae Hwang
• Lee Kwang Hee
• Leem Dong-Seok
• Lim Seon-Jeong
• Bulliard Xavier
• Jin Yong Wan
• Choi Yeong Suk
• Han Moon Gyu

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07D333/36

  Nitrogen atoms · CPC title

• H01L51/0061 Primary

  Electricity · mapped topic

• H01L51/0062

  Electricity · mapped topic

• H01L51/4253

  Electricity · mapped topic