IP Library Granted Patent US 9,660,193
Granted Patent B2
US 9,660,193 · App. 13/980,713 · Granted May 23, 2017

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

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,660,193
App. No.
13/980,713
Granted
May 23, 2017
Kind
B2
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).

Claims (19)

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.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2020
From: KONICA MINOLTA, INC.
To: SONY SEMICONDUCTOR SOLUTIONS CORPORATION
Reel/Frame 051922/0959 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 19, 2013
From: TAKAGI, HIROSHI; ITO, HIROHIDE
To: KONICA MINOLTA, INC.
Reel/Frame 030838/0962 →