Material composition for organic photoelectric conversion layer, organic photoelectric conversion element, method for producing organic photoelectric conversion element, and solar cell

Patent metadata

Field	Value
Publication number	US-9660193-B2
Application number	US-201213980713-A
Country	US
Kind code	B2
Filing date	Jan 10, 2012
Priority date	Jan 25, 2011
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

It is an object of the present invention to provide a material composition for a bulk-heterojunction-type organic photoelectric conversion layer having high photoelectric conversion efficiency and durability through formation of a stable phase-separated structure by drying in a short time with high productivity and to provide an organic photoelectric conversion element, a method of producing the organic photoelectric conversion element, and a solar cell. The material composition for an organic photoelectric conversion layer contains at least a p-type conjugated polymer semiconductor material being a copolymer having a main chain including an electron-donating group and an electron-withdrawing group, an n-type organic semiconductor material having electron acceptability, and a solvent. The solvent is represented by a general formula (1).

First claim

The invention claimed is:

1. A material composition for an organic photoelectric conversion layer, comprising:
a p-type conjugated polymer semiconductor material being a copolymer having a main chain comprising an electron-donating group and an electron-withdrawing group;
an n-type organic semiconductor material having electron acceptability; and
a solvent, wherein
the solvent comprises
at least one selected from the group consisting of: 2-chlorothiophene, 3-chlorothiophene, 2,5-dichlorothiophene, 2-bromothiophene, 3-bromothiophene, 2,3-dibromothiophene, 3,4-dibromothiophene, 3-bromofuran, and 2,5-dibromofuran,
wherein the electron-donating group in the p-type conjugated polymer semiconductor material has a structure represented by at least one of general formula (2) and general formula (3), or a carbazole moiety; and
the electron-withdrawing group in the p-type conjugated polymer semiconductor material has a structure selected from the group consisting of: a benzoselenadiazole skeleton, a 3,4-thiophenedicarboxylic acid imide skeleton, an isoindigo skeleton, a diketopyrrolopyrrole skeleton, a 4-acyl-thieno[3,4-b]thiophene skeleton, a pyrazolo[5, 1-c] [1,2,4] triazole skeleton, and a benzothiazole skeleton,

wherein Z 4 represents a carbon atom, a silicon atom, or a germanium atom; and each R 2 represents an alkyl group, a fluorinated alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or an alkylsilyl group, and may be substituted, where two R 2 s may be bonded together to form a ring and may be the same or different,

wherein R 3 represents an alkyl group, an alkylether group, or an alkylester group and may be substituted, where two R 3 s may be bonded together to form a ring and may be the same or different.

2. The material composition for an organic photoelectric conversion layer of claim 1 , wherein the solvent is contained in a range of 43 to 99% by mass to a total mass of the material composition for an organic photoelectric conversion layer.

3. The material composition for an organic photoelectric conversion layer of claim 1 , wherein the p-type organic semiconductor material and the n-type organic semiconductor material are contained in a mixing ratio of 2:8 to 8:2 by mass.

4. The material composition for an organic photoelectric conversion layer of claim 1 , wherein a concentration of solid content is 1 to 15% by mass.

5. A method for producing an organic photoelectric conversion element, comprising:
applying the material composition for an organic photoelectric conversion layer of claim 1 , which being heated to 50° C. or more; and
drying the applied material composition at 90° C. or more to form an organic photoelectric conversion layer.

6. The material composition for an organic photoelectric conversion layer of claim 1 , wherein the p-type conjugated polymer semiconductor material is PCDTBT (poly[N-9″-heptadecanyl-2,7-carbazole-alt-5,5-(4′,7′-di-2-thienyl-2′,1′,3′-benzothiadiazole)]):

wherein n is an integer.

7. The material composition for an organic photoelectric conversion layer of claim 1 , wherein the solvent is at least one of 2-chlorothiophene and 3-chlorothiophene.

Assignees

• Takagi Hiroshi
• Ito Hirohide
• Konica Minolta Inc

Inventors

• Takagi Hiroshi
• Ito Hirohide

Classifications

• C08G2261/344

  containing heteroatoms · CPC title

• C08G2261/124

  alternating · CPC title

• C08G2261/3246

  containing nitrogen and sulfur as heteroatoms · CPC title

• C08G2261/91

  Photovoltaic applications · CPC title

• C08G2261/1412

  Saturated aliphatic units · CPC title