Perylene Diimide Semiconductors for Soluble High-Mobility Transistors

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Solution Overview

Problem

The development of environmentally stable, high-mobility organic n-type semiconductors for thin film devices is hindered by their vulnerability to ambient conditions and poor solubility in common solvents, which limits their application in large-area organic electronics.

Innovation Solution

1-alkyl substituted alkyl nitrogen-functionalized perylene diimide compounds with specific electron-withdrawing groups are developed, offering improved solubility and air stability, enabling higher carrier mobility and better current modulation in field-effect devices.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If high-mobility rylene compounds (e.g., PDI-FCN2 and NDI-F) are used, then charge transport properties are improved, but solubility deteriorates

Engineering Contradiction:
Improvecharge transport propertiesVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent changes the chemical structure parameters of perylene diimide compounds by introducing specific alkyl substituents at the imide nitrogen positions. These structural modifications alter the physical properties of the compounds, achieving a balance between charge transport mobility and solubility in common solvents like chloroform and toluene.

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If soluble rylene compounds are used, then solubility is improved, but charge transport properties deteriorate

Engineering Contradiction:
ImprovesolubilityVSAvoidcharge transport properties
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent modifies the molecular structure of perylene diimide compounds by introducing specific alkyl groups (such as 1-alkyl substituted alkyl groups) at the imide nitrogen positions. These parameter changes in molecular structure simultaneously improve both solubility in common solvents and charge transport properties, resolving the trade-off between these two characteristics.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If n-type organic semiconductors are developed for thin film devices, then electron-transporting capability is improved, but environmental stability deteriorates due to vulnerability to ambient conditions

Engineering Contradiction:
Improveelectron-transporting capabilityVSAvoidenvironmental stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical composition and molecular structure of perylene diimide compounds by introducing electron-withdrawing groups and specific alkyl substituents. These parameter changes create a more stable molecular structure that maintains electron-transporting capability while improving resistance to ambient conditions such as air and moisture.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP2240970B1Perylene semiconductors and methods of preparation and use thereof
Publication Date: 2018.03.14 FLEXTERRA INC
  • EP2240970B1 patent drawingFigure 1~2
  • EP2240970B1 patent drawingFigure 3~4
  • EP2240970B1 patent drawingFigure 5

AI summary

The present teachings provide semiconducting compounds, materials prepared from such compounds, methods of preparing such compounds and semiconductor materials, as well as various compositions, composites, and devices that incorporate the compounds and semiconductor materials. Specifically, compounds of the present teachings can have higher electron-transport efficiency and higher solubility in common solvents compared to related representative compounds.