Organic compound and photoelectric conversion element

Patent metadata

Field	Value
Publication number	US-2019067590-A1
Application number	US-201816106534-A
Country	US
Kind code	A1
Filing date	Aug 21, 2018
Priority date	Aug 23, 2017
Publication date	Feb 28, 2019
Grant date	—

Abstract

Provided is an organic compound represented by the following general formula [1], the compound having an absorption peak in a long wavelength region:

where Ar 1 and Ar 2 each represent an aryl group having 6 or more and 18 or less carbon atoms or the like, R 1 and R 2 each represent an alkyl group or the like, R 3 represents a hydrogen atom or the like, Y 1 to Y 3 are each independently selected from a methine group and a nitrogen atom, R 4 represents a substituent represented by the general formula [1-1] or the like, and R 5 represents a hydrogen atom or a substituent.

First claim

What is claimed is:

1 . An organic compound, which is represented by the following general formula [1]:

in the general formula [1], Ar 1 and Ar 2 are each independently selected from the group consisting of an aryl group having 6 or more and 18 or less carbon atoms, and a heteroaryl group having 3 or more and 17 or less carbon atoms, the Ar 1 and the Ar 2 may each have a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group as a substituent, the alkyl group, the alkoxy group, the aryl group, or the heteroaryl group serving as the substituent may further have a halogen atom, a cyano group, an alkyl group, or an alkoxy group as a substituent, and the Ar 1 and the Ar 2 may be bonded to each other to form a ring,
R 1 and R 2 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group having 6 or more and 18 or less carbon atoms, and a heteroaryl group having 3 or more and 17 or less carbon atoms, the alkyl group represented by any one of the R 1 and the R 2 may have a halogen atom as a substituent, the aryl group having 6 or more and 18 or less carbon atoms, and the heteroaryl group having 3 or more and 17 or less carbon atoms each represented by any one of the R 1 and the R 2 may each have a halogen atom, a cyano group, an alkyl group, or an alkoxy group as a substituent, and the R 1 and the R 2 may be bonded to each other to form a ring,
R 3 is selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, and an alkyl group, and the alkyl group represented by the R 3 may have a halogen atom as a substituent,
Y 1 to Y 3 are each independently selected from the group consisting of a methine group and a nitrogen atom, and when any one of the Y 1 to the Y 3 represents a methine group, the methine group may have a substituent and the substituent is each independently selected from the group consisting of a halogen atom, a cyano group, and an alkyl group, and the alkyl group serving as the substituent that the methine group has may further have a halogen atom as a substituent, and
R 4 represents a substituent selected from the group consisting of the following general formulae [1-1] and [1-2], and * in each of the following general formulae [1-1] and [1-2] represents a bonding position:

in the general formulae [1-1] and [1-2], R 5 and R 8 to R 10 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an amino group, an amide group, an alkyl group, an alkoxy group, an alkenyl group, an alkynyl group, an aryl group having 6 or more and 18 or less carbon atoms, and a heteroaryl group having 3 or more and 17 or less carbon atoms, and the R 8 and the R 9 are bonded to each other to form a ring, and
the amino group, the amide group, the alkyl group, the alkoxy group, the alkenyl group, the alkynyl group, the aryl group having 6 or more and 18 or less carbon atoms, or the heteroaryl group having 3 or more and 17 or less carbon atoms represented by any one of the R 5 and the R 8 to the R 10 may have a halogen atom, a cyano group, an alkyl group having 1 or more and 8 or less carbon atoms, an alkoxy group having 1 or more and 8 or less carbon atoms, an aryl group having 6 or more and 12 or less carbon atoms, or a heteroaryl group having 4 or more and 11 or less carbon atoms as a substituent, and
in the general formula [1-2], Z 1 and Z 2 are each independently selected from groups represented by the following formulae [1-3] to [1-5], and * in each of the following formulae [1-3] to [1-5] represents a bonding position.

2 . An organic compound according to claim 1 , wherein the R 3 represents a hydrogen atom.

3 . An organic compound according to claim 1 , wherein the organic compound is represented by the following general formula [2]:

in the general formula [2], R 12 and R 13 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an amino group, an amide group, an alkyl group, an alkoxy group, an alkenyl group, an alkynyl group, an aryl group having 6 or more and 18 or less carbon atoms, and a heteroaryl group having 3 or more and 17 or less carbon atoms, the amino group, the amide group, the alkyl group, the alkoxy group, the alkenyl group, the alkynyl group, the aryl group having 6 or more and 18 or less carbon atoms, or the heteroaryl group having 3 or more and 17 or less carbon atoms represented by any one of the R 12 and the R 13 may have a halogen atom, a cyano group, an alkyl group having 1 or more and 8 or less carbon atoms, an alkoxy group having 1 or more and 8 or less carbon atoms, an aryl group having 6 or more and 12 or less carbon atoms, or a heteroaryl group having 4 or more and 11 or less carbon atoms as a substituent, and the R 12 and the R 13 are bonded to each other to form a ring.

4 . An organic compound according to claim 3 , wherein the organic compound is represented by the following general formula [3]:

5 . An organic compound according to claim 3 , wherein the ring formed by the bonding of the R 12 and the R 13 to each other comprises one of a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a thiophene ring, a benzothiophene ring, a furan ring, and a benzofuran ring.

6 . An organic compound according to claim 1 , wherein the organic compound is represented by the following general formula [4]:

7 . An organic compound according to claim 1 , wherein all of the Y 1 to the Y 3 represent methine groups.

8 . An organic compound according to claim 1 , wherein at least one of the Y 1 to the Y 3 represents a nitrogen atom.

9 . An organic compound according to claim 1 , wherein the Z 1 and the Z 2 each represent a group represented by the formula [1-3].

10 . An organic electronic element comprising:
a pair of electrodes; and an organic compound layer arranged between the pair of electrodes, wherein the organic compound layer contains the organic compound of claim 1 .

11 . A photoelectric conversion element comprising:
an anode; a cathode; and a first organic compound layer arranged between the anode and the cathode, wherein the first organic compound layer contains the organic compound of claim 1 .

12 . A photoelectric conversion element according to claim 11 , wherein the first organic compound layer comprises a photoelectric conversion layer and contains an organic n-type compound.

13 . A photoelectric conversion element according to claim 12 , wherein the organic n-type compound comprises one of a fullerene, a fullerene analog, and a fullerene derivative.

14 . A photoelectric conversion element according to claim 11 , further comprising a second organic compound layer arranged between the cathode and the first or

Assignees

• Canon Kk

Inventors

• Nishide Yosuke
• Yamada Naoki
• Ohrui Hiroki
• Iwawaki Hironobu
• Miyashita Hirokazu
• Yamaguchi Tomona
• Kamatani Jun

Classifications

• H01L51/006

  Electricity · mapped topic

• H01L51/0061 Primary

  Electricity · mapped topic

• H01L51/4253

  Electricity · mapped topic

• H01L51/0047

  Electricity · mapped topic

• H01L51/0074

  Electricity · mapped topic