IP Library Granted Patent US 11,201,294
Granted Patent B2
US 11,201,294 · App. 16/796,955 · Granted Dec 14, 2021

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

Inventors: Eiji Fukuzaki (Kanagawa, JP); Tomoaki Yoshioka (Kanagawa, JP)
Assignee: FUJIFILM Corporation
H01L51/0065C07D307/66C07D491/048C07D491/16C09K11/06H01L51/006H01L51/0053H01L51/0061H01L51/0071C09K2211/1018H01L27/307H01L51/4253H01L51/442
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Quick Facts
Patent No.
US 11,201,294
App. No.
16/796,955
Granted
Dec 14, 2021
Kind
B2
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).

Claims (37)

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 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2020
From: FUKUZAKI, EIJI; YOSHIOKA, TOMOAKI
To: FUJIFILM CORPORATION
Reel/Frame 052018/0364 →
Priority Claims (1)
JP JP2017-174118 · Sep 11, 2017 · national
Continuity (2)
Continuation PCTJP2018033091 · Sep 6, 2018
Related Publication 20200194679A1 · Jun 18, 2020