Composition for anode buffer layer of organic thin film solar cell and organic thin film solar cell

Patent metadata

Field	Value
Publication number	US-10020449-B2
Application number	US-201415102775-A
Country	US
Kind code	B2
Filing date	Dec 5, 2014
Priority date	Dec 9, 2013
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

Provided is a composition comprising: a charge-transporting substance that comprises N,N′-diphenylbenzidine; an electron-accepting dopant substance; and an organic solvent. This composition is suitable, for example, as a composition for the anode buffer layer of an organic thin film solar cell, said composition being used to produce a thin film that is suitable for use as an anode buffer layer that makes it possible to achieve an organic thin film solar cell having a high photoelectric conversion efficiency.

First claim

The invention claimed is:

1. An organic thin film solar cell comprising:
an anode buffer layer produced from a composition for an anode buffer layer of an organic thin film solar cell; and
an active layer provided in such a manner as to make contact with the anode buffer layer;
wherein the composition comprises:
a charge-transporting substance including an aryldiamine derivative represented by the formula (1);
an electron-accepting dopant substance;
an organosilane compound; and
an organic solvent

wherein
R 1 to R 4 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, a C1-C20 alkoxy group, a C1-C20 thioalkoxy group, a C1-C20 alkyl group, a C1-C20 haloalkyl group, a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C7-C20 aralkyl group, or a C1-C20 acyl group,
R 5 to R 8 each independently represent a hydrogen atom, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a furanyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a thienyl group wherein these groups may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, a C1-C20 alkoxy group, a C1-C20 thioalkoxy group, a C1-C20 alkyl group, a C1-C20 haloalkyl group, a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C7-C20 aralkyl group, or a C1-C20 acyl group, or a group represented by the formula (2) provided that at least one of R 5 to R 8 is a hydrogen atom,

wherein
R 9 to R 12 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, a C1-C20 alkoxy group, a C1-C20 thioalkoxy group, a C1-C20 alkyl group, a C1-C20 haloalkyl group, a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C7-C20 aralkyl group, or a C1-C20 acyl group, and
R 13 and R 14 each independently represent a phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a furanyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a thienyl group wherein these groups may be bonded to each other to form a ring, and may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, a C1-C20 alkoxy group, a C1-C20 thioalkoxy group, a C1-C20 alkyl group, a C1-C20 haloalkyl group, a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C7-C20 aralkyl group, or a C1-C20 acyl group, and
n represents an integer of 2 to 5.

2. The organic thin film solar cell according to claim 1 , wherein R 5 and R 7 are hydrogen atoms, and R 6 and R 8 are phenyl groups.

3. The organic thin film solar cell according to claim 1 or 2 , wherein n is 2 or 3.

4. The organic thin film solar cell according to claim 1 , wherein the electron-accepting dopant substance includes an arylsulfonic acid compound.

5. The organic thin film solar cell according to claim 4 , wherein the arylsulfonic acid compound is represented by the formula (3),

wherein letter X represents O, letter A represents a naphthalene ring or an anthracene ring, letter B represents a perfluorobiphenyl group having a valence of 2 to 4, letter l represents the number of sulfonic acid groups bonded to the letter A and is an integer satisfying 1≤l≤4, and letter q represents the number of bonds of the letter B and the letter X and is an integer satisfying 2 to 4.

6. The organic thin film solar cell according to claim 5 , wherein the letter X represents O, and the letter A represents a naphthalene ring or an anthracene ring.

7. The organic thin film solar cell according to claim 1 , wherein the active layer includes a fullerene derivative.

8. The organic thin film solar cell according to claim 1 , wherein the active layer includes a polymer including a thiophene skeleton in a main chain.

9. The organic thin film solar cell according to claim 1 , wherein the active layer includes a fullerene derivative and a polymer including a thiophene skeleton in a main chain.

10. An organic thin film solar cell comprising:
an anode buffer layer produced from a composition, for an anode buffer layer of an organic thin film solar cell, comprising: a charge-transporting substance including an aryldiamine derivative represented by the formula (1); an electron-accepting dopant substance; and an organic solvent

wherein
n represents an integer of 2 to 5,
R 1 to R 4 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, a C1-C20 alkoxy group, a C1-C20 thioalkoxy group, a C1-C20 alkyl group, a C1-C20 haloalkyl group, a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C7-C20 aralkyl group, or a C1-C20 acyl group,
R 5 to R 8 each independently represent a hydrogen atom, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a furanyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a thienyl group wherein these groups may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, a C1-C20 alkoxy group, a C1-C20 thioalkoxy group, a C1-C20 alkyl group, a C1-C20 haloalkyl group, a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C7-C20 aralkyl group, or a C1-C20 acyl group, or a group represented by the formula (2) provided that at least one of R 5 to R 8 is a hydrogen atom,

wherein
R 9 to R 12 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, a C1-C20 alkoxy group, a C1-C20 thioalkoxy group, a C1-C20 alkyl group, a C1-C20 haloalkyl group, a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C7-C20 aralkyl group, or a C1-C20 acyl group, and
R 13 and R 14 each independently represent a phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a furanyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a thienyl group wherein these groups may be bonded to each other to form a ring, and may be substituted with a halogen atom, a nitro group, a cyano grou

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Oshima Juro
• Yoshimoto Takuji

Classifications

• H01L51/0036 Primary

  Electricity · mapped topic

• H01L51/0059

  Electricity · mapped topic

• C08G2261/344

  containing heteroatoms · CPC title

• H01L51/0094

  Electricity · mapped topic

• C08G2261/1412

  Saturated aliphatic units · CPC title