Thienoimide Organic Semiconductors for High Electron Mobility

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Solution Overview

Problem

Current n-type organic semiconductor materials exhibit poor electron mobility and stability, limiting their performance in electronic devices such as field-effect transistors and solar cells, and lack structural versatility and accessibility for efficient application.

Innovation Solution

Development of novel organic semiconductor compounds with a thienoimide moiety, which enhances electron affinity and mobility through strong electrowithdrawing effects, promoting high solubility and molecular planarity, and allowing for easy synthesis and modification to optimize electrical properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional n-type organic semiconductor materials are used, then device fabrication is possible, but electron mobility is poor and stability is limited

Engineering Contradiction:
ImprovestabilityVSAvoidaccessibility
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies molecular parameters by introducing the thienoimide moiety with specific substituents (R1-R6) to achieve optimal balance between stability and manufacturability. The thienoimide core structure with可调 substituents allows tuning of electronic properties while maintaining synthetic accessibility through established organic synthesis methods.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining the thienoimide electron-accepting unit with various aromatic substituents (such as thiophene, benzene rings) to form hybrid semiconductor materials that exhibit both high stability and good manufacturability.

Inventive Principle:
Principle #40Composite materials

2Reliability

If perylene building blocks are used, then electron mobility is improved, but structural rigidity and moderate solubility limit structural changes

Engineering Contradiction:
Improveelectron mobilityVSAvoidstructural changes
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent segments the semiconductor material into a thienoimide core unit and separate substituent groups (R1-R6). This segmentation allows the core to maintain high electron mobility while the peripheral substituents can be independently modified to achieve desired solubility and structural properties without affecting the core's electronic function.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention applies local quality by placing different functional groups at specific positions (R1-R6) around the thienoimide core. Each substituent can be optimized for specific properties (solubility, packing, stability) while the core maintains its electron transport function, enabling localized optimization without compromising overall performance.

Inventive Principle:
Principle #3Local quality

3Reliability

If fluorinated side chains are added to improve electron mobility, then mobility increases, but air stability decreases

Engineering Contradiction:
Improveelectron mobilityVSAvoidair stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical parameters by replacing fluorinated groups with alternative electron-withdrawing groups that provide both high electron mobility and air stability. The thienoimide core with specific substituents achieves the desired balance by modifying the LUMO level and molecular packing without introducing air-sensitive fluorine atoms.

Inventive Principle:
Principle #35Parameter changes

4Ease of operation

If conventional n-type materials are used, then device operation is possible, but threshold voltage is high and performance is unsatisfactory

Engineering Contradiction:
Improvedevice operationVSAvoidperformance
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The invention changes key electronic parameters by designing the thienoimide-based molecules with optimized HOMO-LUMO energy levels. This allows the materials to operate at lower threshold voltages while delivering superior electron mobility and stability, directly improving device performance without sacrificing ease of operation.

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 compounds demonstrate high electron mobility, excellent stability under atmospheric conditions, and structural versatility, enabling the creation of efficient and reproducible electronic devices with improved performance in OFETs and other applications.

Implementation Method 1

enhances electron affinity and mobility through strong electrowithdrawing effects

Methodology Applied
Scientific EffectElectrowithdrawing effect:

Data Source

PatentUS9450191B2Thieno[2,3-C]Pyrrole-dione derivatives and their use for organic semiconductors
Publication Date: 2016.09.20 USINVEST LLC
  • US9450191B2 patent drawing
  • US9450191B2 patent drawing
  • US9450191B2 patent drawing

AI summary

Compounds of formulae (I) and (II) useful as organic semiconductor materials, and semiconductor devices containing such organic semiconductor materials are described.