Fused Thiophene DPP Copolymers for Soluble High-Mobility Semiconductors

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Solution Overview

Problem

Unsubstituted fused thiophene-based materials suffer from low solubility, marginal processability, and oxidative instability, limiting their utility in electronic and optoelectronic devices.

Innovation Solution

Development of substituted fused thiophene compounds with specific alkyl and aryl substituents that enhance solubility and processability, and the use of a diketopyrrolopyrrole (DPP)-based monomer in conjunction with a fused thiophene compound to create polymers with improved molecular weight and oxidative stability through palladium-catalyzed coupling reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If unsubstituted fused thiophene-based materials are used, then high mobility and on/off ratio are achieved, but solubility and processability deteriorate

Engineering Contradiction:
Improvedevice performance (mobility and on/off ratio)VSAvoidsolubility and processability
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent introduces alkyl substituents at specific positions (β-positions) of the fused thiophene core, creating local structural modifications that enhance solubility without affecting the global π-conjugation system. This localized substitution strategy improves processability while preserving the high mobility and on/off ratio characteristics of the unsubstituted core structure.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent creates composite structures by combining the fused thiophene core with alkyl substituent groups, forming a hybrid material that exhibits both the electronic properties of the conjugated core and the solubility properties of the alkyl chains. This composite approach resolves the contradiction between performance and processability.

Inventive Principle:
Principle #40Composite materials

2Reliability

If unsubstituted fused thiophene-based materials are used, then high mobility is achieved, but oxidative stability deteriorates

Engineering Contradiction:
Improvecharge carrier mobilityVSAvoidoxidative stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent introduces alkyl substituents at specific positions (β-positions) of the fused thiophene core, creating local structural modifications that enhance solubility without affecting the global π-conjugation system. This localized substitution strategy improves processability while preserving the high mobility and on/off ratio characteristics of the unsubstituted core structure.

Inventive Principle:
Principle #3Local quality

3Reliability

If polymer molecular weight is increased, then oxidative stability and device performance are improved, but solubility and processability deteriorate

Engineering Contradiction:
Improveoxidative stability and device performanceVSAvoidsolubility and processability
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent introduces alkyl substituents at specific positions (β-positions) of the fused thiophene core, creating local structural modifications that enhance solubility without affecting the global π-conjugation system. This localized substitution strategy improves processability while preserving the high mobility and on/off ratio characteristics of the unsubstituted core structure.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent modifies the chemical structure by introducing alkyl substituents, which changes the physical parameters of the polymer including solubility, glass transition temperature, and processability. This parameter modification allows the polymer to maintain high molecular weight while remaining soluble and processable.

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 resulting polymers exhibit higher solubility, processability, and field-effect hole mobility, allowing for the synthesis of high molecular weight materials with improved π-π stacking and oxidative stability, suitable for advanced electronic devices.

Implementation Method 1

the use of a diketopyrrolopyrrole (DPP)-based monomer in conjunction with a fused thiophene compound to create polymers with improved molecular weight and oxidative stability through palladium-catalyzed coupling reactions

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS9580556B2DPP with branched alkyl-chain or (and) fused thiophene with branched alkyl-chain and the related designing strategy to increase the molecular weight of their semi-conducting copolymers
Publication Date: 2017.02.28 CORNING INC
  • US9580556B2 patent drawing
  • US9580556B2 patent drawing
  • US9580556B2 patent drawing

AI summary

Described herein are compositions including hereocyclic fused thiophene based compounds, polymers based on fused thiophene compounds, and methods for making the monomer and polymer along with uses in thin film-based and other devices.