# US 9,428,518 B2 · Perylenemonoimide and naphthalenemonoimide derivatives and their use in dye-sensitized solar cells

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- Number: US 9,428,518 B2
- Document ID: US9428518B2
- Status: Granted
- Kind: B2
- Application number: 14/772,488
- Filed: 2014-03-12
- Published: 2016-01-28
- Granted: 2016-08-30
- Earliest claimed: 2013-03-18
- Assignees: BASF SE; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.
- Applicants: BASF SE; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.
- Inventors: Henrike Wonneberger; Neil Gregory Pschirer; Flavio Luiz Benedito; Ingmar Bruder; Robert Send; Yulian Zagranyarski; Chen Li; Klaus Muellen; Long Chen; Artem Nikolaevich Skabeev
- Web page: https://patentgrep.com/patent/US9428518B2

## CPC

- C07D 491/06: Peri-condensed systems
- C07D 221/04: Ortho- or peri-condensed ring systems
- C07D 471/06: Peri-condensed systems
- C07D 493/06: Peri-condensed systems
- C07D 495/06: Peri-condensed systems
- C09B 5/62: Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
- C09B 57/08: Naphthalimide dyes; Phthalimide dyes
- H01G 9/2059: {comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution}
- 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 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H01G 9/2031: {comprising titanium oxide, e.g. TiO2 (H01G9/2036 takes precedence)}
- H10K 30/151: {the wide bandgap semiconductor comprising titanium oxide, e.g. TiO2}
- H10K 30/50: Photovoltaic [PV] devices
- Y02E 10/542: Dye sensitized solar cells
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- 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
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A sensitizer in a dye-sensitized solar cell, including a compound of formula (I′) where: R1 and R2 are hydrogen, a halogen, an alkyl group, a cycloalkyl group, an aryl group, a hetaryl group, an alkoxy group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, a diarylamino group, or a dialkylamino group; m, n are each independently an integer from 0-4; X is sulfur, oxygen, or NR3, where R3 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group, or a hetaryl group; Y1 is oxygen or N—Z-A, where A is —COOM, —SO3M, or —PO3M, where M is hydrogen, an alkali metal cation, or [NR′]4+, where each R′ is independently hydrogen or an alkyl group, and where Z is C1-C6-alkylene or 1,4-phenylene, where the phenylene radical is optionally substituted by one or more alkyl, nitro, cyano, and halogen substituents.

## Claims

### Claim 1

A sensitizer in a dye-sensitized solar cell, comprising a compound of formula (I′):
wherein:
R1, R2 are each independently hydrogen, a halogen, an alkyl group, a cycloalkyl group, an aryl group, a hetaryl group, an alkoxy group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, a diarylamino group, or a dialkylamino group;
m, n are each independently an integer of 0, 1, 2, 3, or 4;
X is sulfur, oxygen, or NR3, where R3 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group, or a hetaryl group; and
Y1 is oxygen or N—Z-A, wherein:
A is —COOM, —SO3M, or —PO3M, where M is hydrogen, an alkali metal cation, or [NR′]4+, where each R′ is independently hydrogen or an alkyl group; and
Z is C1-C6-alkylene or 1,4-phenylene, where the phenylene radical is optionally substituted by one or more alkyl, nitro, cyano and/or halogen substituents.

### Claim 2 (depends on 1)

The sensitizer according to claim 1, wherein, in formula (I′):
R1, R2 are each independently hydrogen, a halogen atom, an aryl group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, or a dialkylamino group;
m, n are each independently an integer of 0, 1, or 2;
R3 is an alkyl or aryl group;
A is —COOM; and
Z is C1-C6-alkylene or 1,4-phenylene.

### Claim 3

A method for making a compound of formula (I′):
wherein:
R1, R2 are each independently hydrogen, a halogen, an alkyl group, a cycloalkyl group, an aryl group, a hetaryl group, an alkoxy group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, a diarylamino group, or a dialkylamino group;
m, n are each independently an integer of 0, 1, 2, 3, or 4;
X is sulfur, oxygen, or NR3, where R3 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group, or a hetaryl group; and
Y1 is oxygen or N—Z-A, wherein:
A is —COOM, —SO3M, or —PO3M, where M is hydrogen, an alkali metal cation, or [NR′]14+, where each R′ is independently hydrogen or an alkyl group; and
Z is C1-C6-alkylene or 1,4-phenylene, where the phenylene radical is optionally substituted by one or more alkyl, nitro, cyano and/or halogen substituents,
the method comprising:
reacting a compound of formula (II) with a hydroxide alkaline agent or reacting the compound of formula (II) with a hydroxide alkaline agent and then an amine of formula (III):
wherein:
R1, R2 are each independently hydrogen, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, a hetaryl group, an alkoxy group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, a diarylamino group, or a dialkylamino group;
m, n are each independently an integer of 0, 1, 2, 3, or 4;
q is 1;
X is sulfur, oxygen, or NR3, where R3 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group, or a hetaryl group, and
Y2is NR4, where R4 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group or a hetaryl group,
H2N—Z-A (III)
wherein:
A is —COOM, —SO3M, or —PO3M, where M is hydrogen, an alkali metal cation, or [NR′]4+, where each R′ is independently hydrogen or an alkyl group: and
Z is C1-C6-alkylene or 1,4-phenylene, where the phenylene radical is optionally substituted by one or more alkyl, nitro, cyano and/or halogen substituents.

### Claim 4 (depends on 3)

The method according to claim 3, wherein, in formula (II):
R1, R2 are each independently hydrogen, a halogen atom, an aryl group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, or a dialkylamino group;
m, n are each independently an integer of 0, 1, or 2; and
X is sulfur, oxygen, or NR3, where R3 is an alkyl or aryl group.

### Claim 5

A dye-sensitized solar cell, comprising:
a compound of formula (I′)
wherein:
R1, R2 are each independently hydrogen, a halogen, an alkyl group, a cycloalkyl group, an aryl group, a hetaryl group, an alkoxy group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, a diarylamino group, or a dialkylamino group;
m, n are each independently an integer of 0, 1, 2, 3, or 4;
X is sulfur, oxygen, or NR3, where R3 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group, or a hetaryl group; and
Y1 is oxygen or N—Z-A, wherein:
A is —COOM, —SO3M, or —PO3M, where M is hydrogen, an alkali metal cation, or [NR′]4+, where each R′ is independently hydrogen or an alkyl group; and
Z is C1-C6-alkylene or 1,4-phenylene, where the phenylene radical is optionally substituted by one or more alkyl, nitro, cyano and/or halogen substituents.

### Claim 6 (depends on 5)

The dye-sensitized solar cell according to claim 5, wherein, in formula (I′):
R1, R2 are each independently hydrogen, a halogen atom, an aryl group, an aryloxy group, an arylthio group, a hetaryloxy group, a hetarylthio group, or a dialkylamino group;
m, n are each independently an integer of 0, 1, or 2;
R3 is an alkyl or aryl group;
A is —COOM; and
Z is C1-C6-alkylene or 1,4-phenylene.