Photoelectric conversion element, optical sensor, imaging element, and compound

Patent metadata

Field	Value
Publication number	US-11201294-B2
Application number	US-202016796955-A
Country	US
Kind code	B2
Filing date	Feb 21, 2020
Priority date	Sep 11, 2017
Publication date	Dec 14, 2021
Grant date	Dec 14, 2021

Abstract

The invention provides a photoelectric conversion element exhibiting excellent photoelectric conversion efficiency even in a case where the photoelectric conversion film is a thin film. Also, the invention provides an optical sensor and an imaging element including the photoelectric conversion element.
The invention provides a compound applied to the photoelectric conversion element.
The photoelectric conversion element of the invention includes a conductive film, a photoelectric conversion film, and a transparent conductive film, in this order, in which the photoelectric conversion film contains a compound represented by Formula (1).

First claim

What is claimed is:

1. A photoelectric conversion element comprising:
a conductive film;
a photoelectric conversion film;
a transparent conductive film, in this order; and
one or more interlayers between the conductive film and the transparent conductive film, in addition to the photoelectric conversion film,
wherein the photoelectric conversion film contains a compound represented by Formula (1),

in Formula (1), R 1 and R 2 each independently represent an aryl group which may have a substituent, a heteroaryl group which may have a substituent, or an alkyl group which may have a substituent, provided that, at least one of R 1 or R 2 represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, R 3 to R 5 each independently represent a hydrogen atom or a substituent, and A represents a ring containing at least two carbon atoms.

2. The photoelectric conversion element according to claim 1 , wherein the compound represented by Formula (1) is a compound represented by Formula (2),

in Formula (2), R 1 and R 2 each independently represent an aryl group which may have a substituent, a heteroaryl group which may have a substituent, or an alkyl group which may have a substituent, provided that, at least one of R 1 or R 2 represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, R 3 to R 9 each independently represent a hydrogen atom or a substituent, X represents a carbonyl group, a thiocarbonyl group, a dicyanomethylene group, —S—, —O—, or —CR 10 R 11 —, and R 10 and R 11 each independently represent a hydrogen atom or a substituent.

3. The photoelectric conversion element according to claim 1 ,
wherein the compound represented by Formula (1) is a compound represented by Formula (3),

in Formula (3), R 1 and R 2 each independently represent an aryl group which may have a substituent, a heteroaryl group which may have a substituent, or an alkyl group which may have a substituent, provided that, at least one of R 1 or R 2 represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, and R 3 to R 9 each independently represent a hydrogen atom or a substituent.

4. The photoelectric conversion element according to claim 1 ,
wherein at least one of R 1 or R 2 bonds to any of R 3 and R 4 directly or via a linking group to form a ring.

5. The photoelectric conversion element according to claim 1 ,
wherein both of R 1 and R 2 represent an aryl group which may have a substituent.

6. The photoelectric conversion element according to claim 1 ,
wherein both of R 1 and R 2 represent an unsubstituted aryl group.

7. An optical sensor comprising the photoelectric conversion element according to claim 1 .

8. An imaging element comprising the photoelectric conversion element according to claim 1 .

9. A photoelectric conversion film containing a compound represented by Formula (1),

in Formula (1), R 1 and R 2 each independently represent an aryl group which may have a substituent, a heteroaryl group which may have a substituent, or an alkyl group which may have a substituent, provided that, at least one of R 1 or R 2 represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, R 3 to R 5 each independently represent a hydrogen atom or a substituent, and A represents a ring containing at least two carbon atoms,
wherein the photoelectric conversion film further contains an n-type organic semiconductor, and the photoelectric conversion film has a bulk hetero structure formed in a state where the compound represented by Formula (1) and the n-type organic semiconductor are mixed.

10. The compound according to claim 9 which is a compound represented by Formula (2),

in Formula (2), R 1 and R 2 each independently represent an aryl group which may have a substituent, a heteroaryl group which may have a substituent, or an alkyl group which may have a substituent, provided that, at least one of R 1 or R 2 represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, R 3 to R 9 each independently represent a hydrogen atom or a substituent, X represents a carbonyl group, a thiocarbonyl group, a dicyanomethylene group, —S—, —O—, or —CR 10 R 11 —, and R 10 and R 11 each independently represent a hydrogen atom or a substituent.

11. The compound according to claim 9 which is a compound represented by Formula (3),

in Formula (3), R 1 and R 2 each independently represent an aryl group which may have a substituent, a heteroaryl group which may have a substituent, or an alkyl group which may have a substituent, provided that, at least one of R 1 or R 2 represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, and R 3 to R 9 each independently represent a hydrogen atom or a substituent.

12. The photoelectric conversion element according to claim 2 ,
wherein at least one of R 1 or R 2 bonds to any of R 3 and R 4 directly or via a linking group to form a ring.

13. The photoelectric conversion element according to claim 2 ,
wherein both of R 1 and R 2 represent an aryl group which may have a substituent.

14. The photoelectric conversion element according to claim 2 ,
wherein both of R 1 and R 2 represent an unsubstituted aryl group.

15. The photoelectric conversion element according to claim 2 ,
wherein the photoelectric conversion film further contains an n-type organic semiconductor, and the photoelectric conversion film has a bulk hetero structure formed in a state where the compound represented by Formula (2) and the n-type organic semiconductor are mixed.

16. An optical sensor comprising the photoelectric conversion element according to claim 2 .

17. An imaging element comprising the photoelectric conversion element according to claim 2 .

Assignees

• Fujifilm Corp

Inventors

• Fukuzaki Eiji
• Yoshioka Tomoaki

Classifications

• H10K85/653

  comprising only oxygen as heteroatom · CPC title

• H10F30/20

  the devices having potential barriers, e.g. phototransistors · CPC title

• H10F39/12

  Image sensors · CPC title

• C07D491/16 Primary

  Peri-condensed systems · CPC title

• C07D491/147

  the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom · CPC title