IP Library Granted Patent US 9,130,175
Granted Patent B2
US 9,130,175 · App. 14/089,987 · Granted Sep 8, 2015

Organic photoelectric device and image sensor each having active layer including quinacridone and subPC compounds

Inventors: Kwang Hee Lee (Yongin-si, KR); Dong-Seok Leem (Hwaseong-si, KR); Kyu Sik Kim (Yongin-si, KR); Kyung Bae Park (Hwaseong-si, KR)
Assignee: Samsung Electronics Co., Ltd.
H01L51/0072H01L51/008H01L51/0059H01L27/307H01L51/4253
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Quick Facts
Patent No.
US 9,130,175
App. No.
14/089,987
Granted
Sep 8, 2015
Kind
B2
Abstract

An organic photoelectronic 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 a compound represented by Chemical Formula 1 or Chemical Formula 2, and a compound represented by Chemical Formula 3.

Claims (43)

1. An organic photoelectronic 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 3:

wherein, in the Chemical Formula 1,

each of the R 1 and R 2 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 or C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, and a combination thereof, and

each of R 3 to R 12 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 3 to C 30 heteroaryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a halogen atom, a halogen-containing group, and a combination thereof,

wherein, in the Chemical Formula 3,

each of R m to R y 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 3 to C 30 heteroaryl group, a halogen atom, a halogen-containing group, and a combination thereof, and

Z is a C 6 to C 20 aryloxy group having at least one halogen atom, wherein the compound represented by Chemical Formula 1 is a p-type semiconductor,

the compound represented by Chemical Formula 3 is an n-type semiconductor, and

the p-type semiconductor and the n-type semiconductor form a pn junction.

2. The organic photoelectronic device of claim 1 , wherein the Z of the Chemical Formula 3 is a phenoxy group having at least one fluorine atom.

3. The organic photoelectronic device of claim 2 , wherein the Z of the Chemical Formula 3 is represented by the following Chemical Formula A:

4. The organic photoelectronic device of claim 1 , wherein each of the R m to R y of the Chemical Formula 3 are independently hydrogen or at least one thereof includes a halogen atom.

5. The organic photoelectronic device of claim 1 , wherein the compound represented by the Chemical Formula 3 includes at least one selected from compounds represented by the following Chemical Formula 3a or Chemical Formula 3b:

6. The organic photoelectronic device of claim 1 , wherein the compound represented by the Chemical Formula 1 includes at least one selected from compounds represented by the following Chemical Formulae 1a to 1e:

wherein, in the Chemical Formulae 1a to 1e,

each of R 1 and R 2 are independently 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 3 to C 30 heteroaryl group, and a combination thereof.

7. The organic photoelectronic device of claim 1 , wherein

the compound represented by the Chemical Formula 1 is a p-type semiconductor, and

the compound represented by the Chemical Formula 3 is an n-type semiconductor.

8. The organic photoelectronic device of claim 1 , wherein the active layer selectively absorbs light in a green wavelength region.

9. The organic photoelectronic 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.

10. The organic photoelectronic device of claim 1 , wherein the active layer includes an intrinsic layer including the compound represented by the Chemical Formula 1 or 2 and the compound represented by the Chemical Formula 3 at a ratio of about 1:100 to about 100:1.

11. The organic photoelectronic device of claim 10 , wherein the active layer includes an intrinsic layer including the compound represented by the Chemical Formula 1 and the compound represented by the Chemical Formula 3 at a ratio of about 1:10 to about 10:1.

12. The organic photoelectronic device of claim 10 , wherein the active layer further comprises a p-type layer including the compound represented by the Chemical Formula 1.

13. The organic photoelectronic device of claim 10 , wherein the active layer further comprises an n-type layer including the compound represented by the Chemical Formula 3.

14. The organic photoelectronic device of claim 10 , wherein the active layer comprises:

a p-type layer on one side of the intrinsic layer, the p-type layer including the compound represented by the 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 Chemical Formula 3.

15. The organic photoelectronic device of claim 1 , wherein the active layer includes a p-type layer including the compound represented by the Chemical Formula 1 and an n-type layer including the compound represented by the Chemical Formula 3.

16. The organic photoelectronic device of claim 1 , further comprising:

a charge auxiliary layer between at least one of the first electrode and the active layer, and the second electrode and the active layer.

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

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

19. The image sensor of claim 18 , further comprising:

a semiconductor substrate including a photo-sensing device;

a lower insulation layer on the semiconductor substrate;

a color filter on the lower insulation layer; and

an upper insulation layer on the color filter,

wherein the organic photoelectronic device is on the upper insulation layer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2013
From: LEE, KWANG HEE; LEEM, DONG-SEOK; KIM, KYU SIK; PARK, KYUNG BAE
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 031679/0599 →
Priority Claims (1)
KR 10-2013-0059709 · May 27, 2013 · national
Continuity (1)
Related Publication 20140346466A1 · Nov 27, 2014