Photoelectric conversion element, photoelectric conversion module, electronic device, and power supply module

Patent metadata

Field	Value
Publication number	US-12159759-B2
Application number	US-202117906339-A
Country	US
Kind code	B2
Filing date	Mar 12, 2021
Priority date	Mar 16, 2020
Publication date	Dec 3, 2024
Grant date	Dec 3, 2024

Abstract

A photoelectric conversion element including: first support; first electrode; electron-transporting layer; photoelectric conversion layer; hole-transporting layer; and second electrode, the hole-transporting layer including polymer including recurring unit of General Formula (1) below and compound of General Formula (2):

where Ar 1 represents aromatic hydrocarbon, which may have substituent; Ar 2 and Ar 3 each independently represent bivalent group of monocyclic aromatic hydrocarbon, non-condensed polycyclic aromatic hydrocarbon, or condensed polycyclic aromatic hydrocarbon, which may have substituent; Ar 4 represents bivalent group of benzene, thiophene, biphenyl, anthracene, or naphthalene, which may have substituent; R 1 to R 4 each independently represent hydrogen, alkyl, or aryl; and n represents integer that is 2 or more and allows the polymer of General Formula (1) to have weight average molecular weight of 2,000 or more; and

where R 5 to R 9 , which may be identical or different, represent hydrogen, halogen, alkyl, alkoxy, or aryl; and X represents a cation.

First claim

The invention claimed is:

1. A photoelectric conversion element comprising:
a first support;
a first electrode;
an electron-transporting layer;
a photoelectric conversion layer;
a hole-transporting layer that transports holes generated in the photoelectric conversion layer to a second electrode; and
the second electrode,
wherein the hole-transporting layer comprises a polymer comprising a recurring unit represented by General Formula (1) below and a compound represented by General Formula (2) below:

where, in the General Formula (1), Ar 1 represents an aromatic hydrocarbon group, and the aromatic hydrocarbon group may be substituted with a substituent; Ar 2 and Ar 3 each independently represent a bivalent group of a monocyclic aromatic hydrocarbon group, a non-condensed polycyclic aromatic hydrocarbon group, or a condensed polycyclic aromatic hydrocarbon group, which may be substituted with a substituent; Ar 4 represents a bivalent group of benzene, thiophene, biphenyl, anthracene, or naphthalene, which may be substituted with a substituent; R 1 to R 4 each independently represent a hydrogen atom, an alkyl group, or an aryl group; and n represents an integer that is 2 or more and allows the polymer represented by the General Formula (1) to have a weight average molecular weight of 2,000 or more; and

where, in the General Formula (2), R 5 to R 9 , which may be identical to or different from each other, represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an aryl group; X + represents a cation; and B − represents an anion, and
wherein a mass ratio (A:B) between the polymer A including the recurring unit represented by the General Formula (1) and the compound B represented by the General Formula (2) is from 20:1 through 1:1.

2. The photoelectric conversion element according to claim 1 , wherein the electron-transporting layer comprises, on an electron-transporting material on a surface thereof at a side of the photoelectric conversion layer, at least one compound selected from the group consisting of a phosphonic acid compound, a boronic acid compound, a sulfonic acid compound, a halogenated silyl compound, and an alkoxysilyl compound.

3. The photoelectric conversion element according to claim 2 , wherein the compound comprises a nitrogen atom.

4. The photoelectric conversion element according to claim 2 , wherein the compound is represented by General Formula (3) below:

where R 1 and R 2 , which may be identical to or different from each other, represent a hydrogen atom, an alkyl group, an aryl group, or a heterocycle, R 3 represents a bivalent alkylene group, a bivalent aryl group, or a bivalent heterocycle, R 4 represents a phosphonic acid group, a boronic acid group, a sulfonic acid group, a halogenated silyl group, or an alkoxysilyl group, and R 1 or R 2 , R 3 , and N may be joined together to form a ring structure.

5. The photoelectric conversion element according to claim 1 , wherein the photoelectric conversion element comprises at least one salt selected from the group consisting of an organic salt and an inorganic salt between the photoelectric conversion layer and the hole-transporting layer.

6. The photoelectric conversion element according to claim 5 , wherein the salt comprises a halogen atom as an anion.

7. The photoelectric conversion element according to claim 5 , wherein the organic salt is a halogenated hydroacid salt of amine, and the inorganic salt is a halide of an alkali metal.

8. The photoelectric conversion element according to claim 1 , wherein the photoelectric conversion layer comprises a compound represented by General Formula (4) below:
X α Y β Z γ   General Formula (4)

where a ratio of α:β:γ is 3:1:1; β and γ are each an integer of more than 1; X represents a halogen atom; Y represents an organic compound comprising an amino group; and Z represents a metal ion.

9. The photoelectric conversion element according to claim 1 , wherein the photoelectric conversion layer is a perovskite layer comprising a perovskite compound.

10. The photoelectric conversion element according to claim 9 , wherein the perovskite layer comprises a Sb atom, a Cs atom, a Rb atom, or a K atom.

11. The photoelectric conversion element according to claim 1 , further comprising
an amine compound between the photoelectric conversion layer and the hole-transporting layer, and the amine compound is different from an amine compound in the photoelectric conversion layer.

12. The photoelectric conversion element according to claim 1 , wherein the electron-transporting layer comprises a metal oxide.

13. The photoelectric conversion element according to claim 12 , wherein the metal oxide is tin oxide.

14. A photoelectric conversion module comprising photoelectric conversion elements that are electrically coupled in series or in parallel, each of the photoelectric conversion elements being the photoelectric conversion element according to claim 1 .

15. An electronic device comprising:
the photoelectric conversion module according to claim 14 ; and
a device configured to be driven by electric power generated through photoelectric conversion of the photoelectric conversion module.

16. An electronic device comprising:
the photoelectric conversion module according to claim 14 ;
an electricity storage device configured to store electric power generated through photoelectric conversion of the photoelectric conversion module; and
a device configured to be driven by at least one of the electric power generated through photoelectric conversion of the photoelectric conversion module and the electric power stored in the electricity storage device.

17. A power supply module comprising:
the photoelectric conversion module according to claim 14 ; and
a power supply integrated circuit.

18. The photoelectric conversion element according to claim 1 , which is a solar cell.

19. The photoelectric conversion element according to claim 1 , wherein polymer A comprises A-05 and wherein compound B comprises B-14:

Assignees

• Horiuchi Tamotsu
• Tamoto Nozomu
• Tanaka Yuuji
• Kanei Naomichi
• Ide Takahiro
• Ricoh Co Ltd

Inventors

• Horiuchi Tamotsu
• Tamoto Nozomu
• Tanaka Yuuji
• Kanei Naomichi
• Ide Takahiro

Classifications

• H10K85/322

  comprising boron · CPC title

• H10K30/30

  comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains · CPC title

• H10K30/20

  comprising organic-organic junctions, e.g. donor-acceptor junctions · CPC title

• H01G9/2009 Primary

  Solid electrolytes · CPC title

• H10K85/151 Primary

  Copolymers · CPC title