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

Patent metadata

Field	Value
Publication number	US-9818956-B2
Application number	US-201514931413-A
Country	US
Kind code	B2
Filing date	Nov 3, 2015
Priority date	Nov 4, 2014
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

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 between the first electrode and the second electrode, the active layer including the compound represented by Chemical Formula 1.

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 phenyl group and a naphthyl group, provided at least one of Ar 1 and Ar 2 is a naphthyl group,
each of R 1 to R 4 are independently one of hydrogen, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a halogen, and CN,
R a is one of hydrogen, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a halogen, and CN,
p is an integer of 1 or 2,
n is 0 or 1,
m is an integer ranging from 1 to 4, and
the compound has 7 aromatic rings.

2. The compound of claim 1 , wherein the compound is represented by Chemical Formula 2:

wherein, in Chemical Formula 2,
each of R 1 to R 4 are independently one of hydrogen, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a halogen, and CN, and
m is an integer ranging from 1 to 4.

3. The compound of claim 1 , wherein the compound is represented by Chemical Formula 3:

wherein, in Chemical Formula 3,
each of R 1 to R 4 are independently one of hydrogen, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a halogen, and CN, and
m is an integer ranging from 1 to 4.

4. The compound of claim 1 , wherein the compound is represented by Chemical Formula 4:

wherein, in Chemical Formula 4,
each of R 1 to R 4 are independently one of hydrogen, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a halogen, and CN,
R a is independently one of hydrogen, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a halogen, and CN,
p is an integer of 1 or 2, and
m is an integer ranging from 1 to 4.

5. The compound of claim 1 , wherein the compound is represented by Chemical Formula 5:

wherein, in Chemical Formula 3,
each of R 1 to R 4 are independently one of hydrogen, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a halogen, and CN,
R a is independently one of hydrogen, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a halogen, and CN,
p is an integer of 1 or 2, and
m is an integer ranging from 1 to 4.

6. The compound of claim 1 , wherein the compound has a maximum absorption wavelength (λ max ) of about 530 nm to about 570 nm in a thin film state.

7. The compound of claim 1 , wherein the compound shows a light absorption curve having a full width at half maximum (FWHM) of about 50 nm to about 100 nm in a thin film state.

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

9. 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 phenyl group and a naphthyl group, provided at least one of Ar 1 and Ar 2 is a naphthyl group,
each of R 1 to R 4 are independently one of hydrogen, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a halogen, and CN,
R a is one of hydrogen, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a halogen, and CN,
p is an integer of 1 or 2,
n is 0 or 1, and
m is an integer ranging from 1 to 4,
the compound having a maximum absorption wavelength (λ max ) of about 530 nm to about 570 nm in a thin film state, and
the compound showing a light absorption curve having a full width at half maximum (FWHM) of about 50 nm to about 100 nm in a thin film state.

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 of claim 1 .

11. The organic photoelectric device of claim 10 , wherein the active layer further comprises an n-type semiconductor compound.

12. The organic photoelectric device of claim 11 , wherein the n-type semiconductor compound is one of sub-phthalocyanine, fullerene or a fullerene derivative, thiophene or a thiophene derivative, and a combination thereof.

13. The organic photoelectric device of claim 11 , wherein the active layer comprises an intrinsic layer including the compound represented by Chemical Formula 1.

14. The organic photoelectric device of claim 13 , wherein the active layer further comprises at least one of a p-type layer on one side of the intrinsic layer and an n-type layer on the other side of the intrinsic layer.

15. The organic photoelectric device of claim 11 , wherein the active layer further comprises a second p-type semiconductor compound configured to selectively absorb green light.

16. The organic photoelectric device of claim 15 , wherein the second p-type semiconductor compound is represented by Chemical Formula 9:

wherein, in Chemical Formula 9,
each of R 21 to R 23 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 aliphatic hydrocarbon group, a substituted or unsubstituted C 6 to C 30 aromatic hydrocarbon group, a substituted or unsubstituted C 1 to C 30 aliphatic heterocyclic group, a substituted or unsubstituted C 2 to C 30 aromatic heterocyclic group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 6 to C 30 aryloxy group, a thiol group, a substituted or unsubstituted C 1 to C 30 alkylthio group, a substituted or unsubstituted C 6 to C 30 arylthio group, a cyano group, a cyano-containing group, a halogen, a halogen-containing group, a substituted or unsubstituted sulfonyl group, and a combination thereof,
R 21 to R 23 are independently present or are fused to each other to provide a ring,
each of L 1 to L 3 are independently one of a single bond, a substituted or unsubstituted C 1 to C 30 alkylene group, a substituted or unsubstituted C 6 to C 30 arylene group, a divalent substituted or unsubstituted C 3 to C 30 heterocyclic group, and a combination thereof, and
each of R 31 to R 33 are independently one of 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 3 to C 30 heterocyclic group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, and a combination thereof.

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

18. The image sensor of claim 17 , 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 plura

Assignees

• Samsung Electronics Co Ltd

Inventors

• Ro Takkyun
• Lim Seon-Jeong
• Park Kyung Bae
• Yun Sung Young
• Lee Gae Hwang
• Leem Dong-Seok
• Jin Yong Wan
• Tadao Yagi
• Han Moon Gyu
• Heo Chuljoon

Classifications

• H01L51/0046

  Electricity · mapped topic

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title

• H01L51/0067

  Electricity · mapped topic

• H01L51/4293

  Electricity · mapped topic

• H01L51/008

  Electricity · mapped topic