High-Purity Fullerene Derivative for Stable Organic Solar Cells

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Solution Overview

Problem

Current fullerene derivatives for organic thin-film solar cells, except for [6,6]-phenyl-C61-butyric acid methyl ester (PCBM), have not demonstrated high and stable photoelectric conversion efficiency, limiting the development of advanced n-type semiconductor materials.

Innovation Solution

A fullerene derivative with a purity of ≥99% is developed, represented by formula (1), where ring A is C60 fullerene, R1 is C1-6 alkyl or naphthyl optionally substituted with halogen, and Ar is phenyl or naphthyl optionally substituted with C1-8 alkyl groups, combined with a donor-acceptor type π-conjugated polymer, enhancing photoelectric conversion efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If fullerene derivatives other than PCBM are used as n-type semiconductor materials, then structural diversity and potential performance improvement are achieved, but stable and high photoelectric conversion efficiency has not been demonstrated

Engineering Contradiction:
Improvestructural diversityVSAvoidphotoelectric conversion efficiency stability
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent systematically varies key structural parameters of fullerene derivatives including substituent types (alkyl chains of different lengths, aromatic groups), substitution positions (mono-, di-, tri-substituted), and molecular weight to optimize photoelectric conversion efficiency while maintaining stability, moving beyond PCBM's fixed structure

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite material systems by combining specific fullerene derivative n-type semiconductors with p-type semiconductor polymers (such as P3HT, PTB7) to form bulk heterojunction structures, where the composite interface enables efficient charge separation and transport while achieving both high efficiency and stability

Inventive Principle:
Principle #40Composite materials

2Productivity

If bulk heterojunction structure is used in organic thin-film solar cells, then photoelectric conversion efficiency increases significantly, but device complexity and material selection requirements increase

Engineering Contradiction:
Improvephotoelectric conversion efficiencyVSAvoidmaterial selection requirements
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent optimizes the local properties of the bulk heterojunction by carefully selecting fullerene derivatives with specific molecular weights, solubility characteristics, and crystallinity to ensure proper phase separation and domain morphology at the nanoscale, enabling efficient charge separation while managing device complexity through targeted material design

Inventive Principle:
Principle #3Local quality

3Ease of manufacture

If conventional fullerene derivative synthesis methods are used, then production is achieved, but yield and purity are limited

Engineering Contradiction:
Improvesynthesis feasibilityVSAvoidpurity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent employs preliminary purification actions during synthesis including column chromatography and recrystallization steps to remove impurities and side products early in the process, ensuring high purity of the fullerene derivative materials before device fabrication, thereby achieving both manufacturing feasibility and high purity

Inventive Principle:
Principle #10Preliminary action

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The organic power-generating layer achieves high photoelectric conversion efficiency and easy film formation, forming a bulk heterojunction structure for improved solar cell performance.

Implementation Method 1

Organic thin-film solar cells are formed by a coating technique with a solution of an organic compound, which is a photoelectric conversion material

Methodology Applied
Scientific EffectPhotovoltaic effect: Photovoltaic Effect

Implementation Method 2

the use of the bulk heterojunction structure has particularly led to a significant increase in photoelectric conversion efficiency

Methodology Applied
Scientific EffectPhotoelectric conversion: Photoelectric Effect

Data Source

PatentEP2999018B1Fullerene derivative and n-type semiconductor material
Publication Date: 2024.02.28 DAIKIN INDUSTRIES LTD
  • EP2999018B1 patent drawing
  • EP2999018B1 patent drawing
  • EP2999018B1 patent drawing

AI summary

The object of the present invention is to provide a material having excellent performance as an n-type semiconductor material, in particular an n-type semiconductor for photoelectric conversion elements such as organic thin-film solar cells. The present invention provides an n-type semiconductor consisting of a fullerene derivative having a purity of 99% or more as defined below, the fullerene derivative being represented by formula (1): wherein ring A represents C60 fullerene; R1 represents a hydrogen atom, alkyl optionally having at least one substituent, or aryl optionally having at least one substituent; and Ar represents aryl optionally substituted with at least one alkyl group, the purity being defined by the following equation: Purity%=100−Dmax% wherein the Dmax (%) is the maximum value among the absolute value of the difference between an analysis value and a theoretical value obtained in elemental analysis of carbon, the absolute value of the difference between an analysis value and a theoretical value obtained in elemental analysis of hydrogen, and the absolute value of the difference between an analysis value and a theoretical value obtained in elemental analysis of nitrogen.