Organic photoelectric conversion element, optical area sensor, image pickup device, and image pickup apparatus

Patent metadata

Field	Value
Publication number	US-11121182-B2
Application number	US-201816056270-A
Country	US
Kind code	B2
Filing date	Aug 6, 2018
Priority date	Feb 9, 2016
Publication date	Sep 14, 2021
Grant date	Sep 14, 2021

Abstract

An organic photoelectric conversion element includes an electron-collecting electrode, a hole-collecting electrode, and a photoelectric conversion portion which is disposed between the electron-collecting electrode and the hole-collecting electrode. The photoelectric conversion portion includes a first organic compound layer. A second organic compound layer is disposed between the hole-collecting electrode and the photoelectric conversion portion. The first organic compound layer contains a first compound having at least a fullerene skeleton and a second compound having a fluoranthene skeleton.

First claim

The invention claimed is:

1. An organic photoelectric conversion element comprising:
an anode;
a cathode; and
a photoelectric conversion portion which is disposed between the anode and the cathode,
wherein the photoelectric conversion portion includes a first organic compound having at least a fullerene skeleton and a second organic compound having a fluoranthene skeleton, and
wherein the second compound has a vinyl group provided that the second organic compound excludes a fluoranthene skeleton represented by general formulas (2) and (7) shown below:

wherein, in formula (2), R 11 to R 22 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a vinyl group represented by general formula (I) below, a substituted or unsubstituted amino group, or a cyano group:
wherein, in formula (7), R 54 to R 95 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a vinyl group represented by general formula (I) below, a substituted or unsubstituted amino group, or a cyano group:
—CR a =CR b R c   (I)

wherein, in formula (I), at least two substituents among R a , R b , and R c may combine to form a ring structure,
wherein the vinyl group is a substituent represented by any one of general formulas (21) to (25) below:

wherein, in formula (21), the asterisk represents a bond, and R 301 to R 304 each represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, an amino group, an alkoxy group, an aryloxy group, a halogen atom, or a cyano group;
wherein, in formula (22), the asterisk represents a bond, and R 305 to R 310 each represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, an amino group, an alkoxy group, an aryloxy group, a halogen atom, or a cyano group;
wherein, in formula (23), the asterisk represents a bond, and R 311 to R 316 each represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, an amino group, an alkoxy group, an aryloxy group, a halogen atom, or a cyano group;
wherein, in formula (24), the asterisk represents a bond, and R 317 and R 318 each represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, an amino group, an alkoxy group, an aryloxy group, a halogen atom, or a cyano group; and
wherein, in formula (25), the asterisk represents a bond, and R 319 represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, an amino group, an alkoxy group, an aryloxy group, a halogen atom, or a cyano group, R 320 and R 321 each represent a cyano group.

2. The organic photoelectric conversion element according to claim 1 , wherein the first organic compound is fullerene C60.

3. The organic photoelectric conversion element according to claim 1 , wherein the second organic compound is a compound represented by any one of general formulas (1), (3) to (6), and (8) to (17) below:

wherein, in formula (1), R 1 to R 10 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, the vinyl group, a substituted or unsubstituted amino group, or a cyano group,
at least one of the R 3 , R 4 , R 8 and R 9 represent the vinyl group;
wherein, in formula (3), R 23 to R 35 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, the vinyl group, a substituted or unsubstituted amino group, or a cyano group,
at least one of the R 25 , R 26 , R 31 and R 32 represent the vinyl group;
wherein, in formula (4), R 36 to R 53 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, the vinyl group, a substituted or unsubstituted amino group, or a cyano group,
at least one of the R 38 , R 39 , R 47 and R 48 represent the vinyl group;
wherein, in formula (5), R 54 to R 69 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, the vinyl group, a substituted or unsubstituted amino group, or a cyano group,
at least one of the R 56 , R 57 , R 63 and R 64 represent the vinyl group;
wherein, in formula (6), R 70 to R 83 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, the vinyl group, a substituted or unsubstituted amino group, or a cyano group,
at least one of the R 72 , R 73 , R 79 and R 80 are represent the vinyl group;
wherein, in formula (8), R 96 to R 107 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, the vinyl group, a substituted or unsubstituted amino group, or a cyano group,
at least one of the R 97 , R 98 , R 103 and R 104 are represent the vinyl group;
wherein, in formula (9), R 108 to R 121 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, the vinyl group, a substituted or unsubstituted amino group, or a cyano group,
at least one of the R 109 , R 110 , R 116 and R 117 are represent the vinyl group;
wherein, in formula (10), R 122 to R 137 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, the vinyl group, a substituted or unsubstituted amino group, or a cyano group,
at least one of the R 123 , R 124 , R 131 and R 132 are represent the vinyl group;
wherein, in formula (11), R 138 to R 153 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, the vinyl group, a substituted or unsubstituted amino group, or a cyano group,
at least one of the R 139 , R 140 , R 147 and R 148 are represent the vinyl group;
wherein, in formula (12), R 154 to R 167 each represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, the vinyl group, a substituted or unsubstituted amino group, or a cyano group,
at least one of the R 156 , R 157 , R 163 and R 164 are represent the vinyl group;
wherein, in formula (13), R 168 to R 185 each represent a hydrogen atom, a

Assignees

• Canon Kk

Inventors

• Kamatani Jun
• Yamada Naoki
• Ohrui Hiroki
• Kishino Kengo
• Iwawaki Hironobu
• Shiobara Satoru
• Yamaguchi Tomona
• Itabashi Masumi
• Nishide Yosuke
• Miyashita Hirokazu

Classifications

• H10K39/32

  Organic image sensors · CPC title

• H10K85/624 Primary

  containing six or more rings · CPC title

• H10F39/8063

  Microlenses · CPC title

• H10F39/8053

  Colour filters · CPC title

• H10F39/12

  Image sensors · CPC title