Photoelectric conversion element, imaging device, optical sensor, and method of using photoelectric conversion element

Patent metadata

Field	Value
Publication number	US-2016013426-A1
Application number	US-201514863962-A
Country	US
Kind code	A1
Filing date	Sep 24, 2015
Priority date	Mar 28, 2013
Publication date	Jan 14, 2016
Grant date	—

Abstract

The present invention provides a photoelectric conversion element having a photoelectric conversion film which exhibits excellent photoelectric conversion efficiency and responsiveness, an imaging device, an optical sensor, and a method of using a photoelectric conversion element. In the photoelectric conversion element of the invention, a photoelectric conversion material contains at least one selected from the group consisting of a compound represented by General formula (1), a compound represented by General formula (2), and a compound represented by General formula (3).

First claim

What is claimed is:

1 . A photoelectric conversion element in which a conductive film, a photoelectric conversion film containing a photoelectric conversion material, and a transparent conductive film are laminated in this order,
wherein the photoelectric conversion material contains at least one compound selected from the group consisting of a compound represented by General formula (1), a compound represented by General formula (2), and a compound represented by General formula (3),

(in General formulae (1) to (3), each of X 1 and X 2 independently represents an oxygen atom, a sulfur atom, ═CR 1a R 1b , or ═NR 1c ; each of Y 1 and Y 2 independently represents an oxygen atom, a sulfur atom, >CR 1d R 1e , or >SiR 1f R 1g ; each of R 1a to R 1g independently represents a hydrogen atom or a substituent; Q represents a group selected from the group consisting of groups represented by General formulae (4) to (8); each of R 1 and R 2 independently represents a substituent; each of R 3 to R 24 independently represents a hydrogen atom or a substituent; n represents 0 or 1; and
when n=1, carbon atoms represented by *1 to *4 in General formulae (4) to (8) correspond to carbon atoms represented by *1 to *4 in General formulae (1) to (3), respectively; and when n=0, the compounds represented by General formulae (1) to (3) are compounds represented by General formulae (9) to (11), respectively).

2 . The photoelectric conversion element according to claim 1 ,
wherein the photoelectric conversion material contains at least one compound selected from the group consisting of a compound represented by General formula (12) and a compound represented by General formula (13),

(in General formulae (12) and (13), definitions of Q, R 1 , and R 2 are same as definitions described in claim 1 ).

3 . The photoelectric conversion element according to claim 1 ,
wherein each of R 1 and R 2 in General formulae (1) to (3) represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent.

4 . The photoelectric conversion element according to claim 1 ,
wherein at least one of R 1 and R 2 in General formulae (1) to (3) is a group represented by General formula (14),

(in General formula (14), each of R 30 and R 31 independently represents an alkyl group, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent; R 32 represents an arylene group which may have a substituent or a heteroarylene group which may have a substituent; R 30 to R 32 may form a ring by being linked to each other; and *5 represents a bonding position).

5 . The photoelectric conversion element according to claim 4 ,
wherein in General formula (14), R 30 and R 31 , R 30 and R 32 , or R 31 and R 32 form a ring by being directly bonded to each other or by being bonded to each other through a linking group.

6 . The photoelectric conversion element according to claim 1 ,
wherein in General formulae (1) to (3), at least one of R 1 and R 2 is a group represented by General formula (18),

(in General formula (18), each of R 33 to R 37 independently represents a hydrogen atom or a substituent; R 32 represents an arylene group which may have a substituent or a heteroarylene group which may have a substituent; R 31 represents an alkyl group, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent; R 33 and R 32 , R 37 and R 31 , or R 31 and R 32 may form a ring by being linked to each other; and *5 represents a bonding position).

7 . The photoelectric conversion element according to claim 1 ,
wherein in General formulae (1) to (3), at least one of R 1 and R 2 is a group represented by General formula (15),

(in General formula (15), each of R 33 to R 42 independently represents a hydrogen atom or a substituent; R 32 represents an arylene group which may have a substituent or a heteroarylene group which may have a substituent; R 37 and R 38 , R 32 and R 33 , and
R 32 and R 42 may form a ring by being linked to each other; and *5 represents a bonding position).

8 . The photoelectric conversion element according to claim 1 ,
wherein in General formulae (1) to (3), n=0.

9 . The photoelectric conversion element according to claim 1 ,
wherein in General formulae (1) to (3), R 1 and R 2 represent a same substituent.

10 . The photoelectric conversion element according to claim 6 ,
wherein R 1 and R 2 both represent the group represented by General formula (18), each of X 1 and X 2 represents an oxygen atom, each of Y 1 and Y 2 represents an oxygen atom, n=0, and R 1 and R 2 represent a same substituent.

11 . The photoelectric conversion element according to claim 1 ,
wherein the photoelectric conversion film further contains an n-type organic compound.

12 . The photoelectric conversion element according to claim 11 ,
wherein the n-type organic compound contains a fullerene-based compound selected from the group consisting of fullerenes and derivatives thereof.

13 . The photoelectric conversion element according to claim 12 ,
wherein a content ratio of the fullerene-based compound to a sum of the fullerene-based compound and one or more of the compounds represented by General formulae (1) to (3) (film thickness of the fullerene-based compound expressed in terms of a single layer/(film thickness of one or more of the compounds represented by General formulae (1) to (3) expressed in terms of a single layer+film thickness of the fullerene-based compound expressed in terms of a single layer)) is equal to or greater than 50% by volume.

14 . The photoelectric conversion element according to claim 1 ,
wherein a charge blocking film is disposed between the conductive film and the transparent conductive film.

15 . The photoelectric conversion element according to claim 14 , comprising the conductive film, the charge blocking film, the photoelectric conversion film, and the transparent conductive film in this order, or the conductive film, the photoelectric conversion film, the charge blocking film, and the transparent conductive film in this order.

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

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

18 . A method of using the photoelectric conversion element according to claim 1 ,
wherein the conductive film and the transparent conductive film constitute a pair of electrodes, and an electric field of 1×10 −5 V/cm to 1×10 7 V/cm is applied between the pair of electrodes.

19 . A compound represented by General formula (16),

(in General formula (16), each of R 43 and R 44 independently represents an aryl group which ma

Assignees

• Fujifilm Corp

Inventors

• Yoshioka Tomoaki
• Tsukase Masaaki
• Ichiki Takahiko
• Sawaki Daigo

Classifications

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D493/04 Primary

  Ortho-condensed systems · CPC title