Fullerene Derivative Thermal Stability for Vacuum Deposition

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Solution Overview

Problem

Fullerene derivatives are typically thermally decomposed by vacuum deposition, limiting their film formation to solution coating, which results in lower product reliability compared to vacuum deposition.

Innovation Solution

A fullerene derivative with a specific structure (Ar-C-X-R, where Ar is an aromatic ring, * is a carbon atom, X is O, S, Se, or Te, and R is an organic group) is synthesized through a method involving Grignard reagent preparation, arylhydrofullerene synthesis, aryl fullerene dimer oxidation, and subsequent oxidation steps, allowing for deposition at temperatures equal to or higher than the sublimation temperature without thermal decomposition.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If vacuum deposition is used to form fullerene derivatives into films, then manufacturing reliability and product quality are improved, but thermal decomposition occurs during deposition

Engineering Contradiction:
Improveproduct reliabilityVSAvoidthermal decomposition
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent modifies the molecular structure of fullerene derivatives by introducing specific substituents (formula 1 with Ar, X, and R groups) that alter thermal stability parameters, enabling the material to withstand vacuum deposition temperatures without decomposition

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite fullerene derivative structures combining the C60 core with aromatic ring substituents and heteroatoms (O, S, Se, or Te), forming a composite material with enhanced thermal stability suitable for vacuum deposition

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If solution coating is used to form fullerene derivatives into films, then manufacturing cost is reduced, but manufacturing precision and product reliability deteriorate

Engineering Contradiction:
Improvemanufacturing costVSAvoidproduct reliability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

By changing the thermal stability parameters of fullerene derivatives through structural modification (formula 1), the material becomes suitable for vacuum deposition, transitioning from low-reliability solution coating to high-reliability vacuum deposition processes

Inventive Principle:
Principle #35Parameter changes

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 method enables the production of a fullerene derivative with excellent characteristics that can be used as an electron acceptor or transport material, achieving high-purity deposits and improved electronic device performance, including enhanced electron mobility and energy conversion efficiency in organic solar cells.

Implementation Method 1

a first step of preparing a Grignard reagent by reaction of an aryl halide with magnesium; a second step of synthesizing an arylhydrofullerene by reaction of the Grignard reagent and fullerene

Methodology Applied
Scientific EffectGrignard reaction: Chemical Bonding

Implementation Method 2

a third step of synthesizing an aryl fullerene dimer by oxidizing the arylhydrofullerene in the presence of a base

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 3

a fourth step of synthesizing a fullerene derivative having a structure of formula (1) by oxidizing the aryl fullerene dimer

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 4

a step of heating the fullerene derivative having a structure of formula (1) or formula (2) to a temperature equal to or higher than the sublimation temperature to deposit the fullerene derivative

Methodology Applied
Scientific EffectSublimation: Sublimation

Data Source

PatentUS20230099136A1Fullerene derivative, fullerene derivative production method, deposit, film, and electronic device
Publication Date: 2023.03.30 MITSUBISHI CORPORATION
  • US20230099136A1 patent drawing
  • US20230099136A1 patent drawing
  • US20230099136A1 patent drawing

AI summary

A fullerene derivative has a structure of formula (1) or formula (2): wherein Ar is a substituted or unsubstituted aromatic ring, * is a carbon atom at the point of attachment to a fullerene core, X is O, S, Se, or Te, and R is an organic group.