# US 10,319,533 B2 · Photoelectric conversion element and solar cell

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- Number: US 10,319,533 B2
- Document ID: US10319533B2
- Status: Granted
- Kind: B2
- Application number: 15/866,536
- Filed: 2018-01-10
- Published: 2018-07-12
- Granted: 2019-06-11
- Earliest claimed: 2017-01-12
- Assignees: Ricoh Company, Ltd.
- Applicants: Tamotsu Horiuchi; Yuuji Tanaka; Tsuyoshi Matsuyama; Takahiro Ide; Tokushige Kino; Shigeyo Suzuki; Naomichi Kanei
- Inventors: Tamotsu Horiuchi; Yuuji Tanaka; Tsuyoshi Matsuyama; Takahiro Ide; Tokushige Kino; Shigeyo Suzuki; Naomichi Kanei
- Web page: https://patentgrep.com/patent/US10319533B2

## CPC

- H01G 9/2059: {comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution}
- H01G 9/2018: {characterised by the ionic charge transport species, e.g. redox shuttles}
- H10K 30/82: Transparent electrodes, e.g. indium tin oxide [ITO] electrodes
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/621: {Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/653: {comprising only oxygen as heteroatom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/655: {comprising only sulfur as heteroatom}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 2102/00: Constructional details relating to the organic devices covered by this subclass
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- Y02E 10/542: Dye sensitized solar cells
- Y02E 10/549: Organic PV cells
- H01G: CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE (selection of specified materials as dielectric H01B3/00; capacitors having potential barriers H10D1/62, H10K10/10)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A photoelectric conversion element including a first electrode, an electron transport layer on the first electrode, a charge transfer layer, and a second electrode is provided. The electron transport layer includes an electron transport compound, and the electron transport compound carries a compound represented by the following formula (1) and a compound represented by the following formula (2): where each of X1 and X2 independently represents oxygen atom, sulfur atom, or selenium atom; R1 represents methine group; R2 represents an alkyl group, an aryl group, or a heterocyclic group; each of R3 independently represents an acidic group; m represents an integer of 1 or 2; and each of Z1 and Z2 independently represents a group forming a cyclic structure; R5—R4—COOH Formula (2) where R4 represents an aryl group or a heterocyclic group; and R5 represents an alkyl group, an alkoxy group, an alkenyl group, an alkylthio group, or an aryl ether group.

## Claims

### Claim 1

A photoelectric conversion element comprising:
a first electrode;
an electron transport layer on the first electrode, the electron transport layer comprising an electron transport compound, the electron transport compound carrying:
a compound represented by the following formula (1):
where each of X1 and X2 independently represents oxygen atom, sulfur atom, or selenium atom; R1 represents methine group; R2 represents an alkyl group, an aryl group, or a heterocyclic group; each of R3 independently represents an acidic group; m represents an integer of 1 or 2; and each of Z1 and Z2 independently represents a group forming a cyclic structure; and
a compound represented by the following formula (2):
R5—R4—COOH Formula (2)
where R4 represents an aryl group or a heterocyclic group; and R5 represents an alkyl group, an alkoxy group, an alkenyl group, an alkylthio group, or an aryl ether group;
a charge transfer layer; and
a second electrode; and wherein the compound represented by the formula (1) is represented by the following formula (4):
where each of X1 and X2 independently represents oxygen atom or sulfur atom; R2 represents an alkyl group, an aryl group, or a heterocyclic group; each of R3 independently represents an acidic group; and each of R6 and R7 independently represents an alkyl group, an aryl group, or a non-cyclic structure, or R6 and R7 share bond connectivity to form a cyclic structure.

### Claim 2 (depends on 1)

The photoelectric conversion element of claim 1, wherein the compound represented by the formula (2) is represented by the following formula (5):
where R8 represents an alkyl group, an alkenyl group, or an aryl group; and n represents an integer of from 1 to 3.

### Claim 3 (depends on 1)

The photoelectric conversion element of claim 1, further comprising a blocking layer between the first electrode and the electron transport layer.

### Claim 4 (depends on 1)

The photoelectric conversion element of claim 1, wherein the electron transport compound comprises an oxide semiconductor.

### Claim 5 (depends on 4)

The photoelectric conversion element of claim 4, wherein the oxide semiconductor comprises at least one selected from the group consisting of titanium oxide, zinc oxide, tin oxide, and niobium oxide.

### Claim 6 (depends on 1)

The photoelectric conversion element of claim 1, wherein the charge transfer layer comprises an organic hole transport material or an inorganic hole transport material.

### Claim 7 (depends on 6)

The photoelectric conversion element of claim 6, wherein the organic hole transport material comprises a compound represented by the following formula (6):
where each of R9 to R12 independently represents an amino group.

### Claim 8 (depends on 1)

The photoelectric conversion element of claim 1, further comprising an absorption wavelength control layer on one side of the first electrode opposite to the electron transport layer, the absorption wavelength control layer exhibiting a total light transmittance of 90% or more and a rate of blocking ultraviolet light having a wavelength of 385 nm or less of 99% or more.

### Claim 9 (depends on 1)

A solar cell comprising the photoelectric conversion element of claim 1.