E-configuration DPP Copolymer Air Stability

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Solution Overview

Problem

Diketopyrrolopyrrole (DPP) copolymers used in organic thin film transistors (OTFTs) and photovoltaics face challenges due to their sensitivity to oxygen and moisture, leading to instability and reduced charge carrier mobility when not well-matched with electrode work functions.

Innovation Solution

Development of DPP-based copolymers with a specific structure featuring a carbon-carbon double bond in the E-configuration, enhancing charge carrier mobility and stability by optimizing interfacial properties and incorporating vinyl groups, which are synthesized in an oxygen-free environment to prevent degradation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If DPP copolymers are used to achieve high charge carrier mobility, then charge carrier mobility is improved, but air stability deteriorates due to sensitivity to oxygen and moisture

Engineering Contradiction:

Improvecharge carrier mobilityVSAvoidair stability

Core Design Contradiction:

ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies local quality by introducing specific functional groups (vinyl groups in E-configuration) at particular positions within the DPP copolymer structure. This localized structural modification enhances air stability without compromising the overall charge carrier mobility of the material

Inventive Principle:

Principle #3Local quality

Solution Approach 2:

The patent creates composite materials by combining DPP copolymers with vinyl groups in E-configuration to form a new copolymer structure. This composite approach integrates the high mobility characteristics of DPP with the enhanced stability provided by the vinyl groups, achieving both improved charge carrier mobility and air stability

Inventive Principle:

Principle #40Composite materials

2Reliability

If DPP copolymers are used to achieve high charge carrier mobility, then charge carrier mobility is improved, but device fabrication under ambient conditions deteriorates due to oxygen and moisture sensitivity

Engineering Contradiction:

Improvecharge carrier mobilityVSAvoidfabrication under ambient conditions

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The patent introduces vinyl groups at specific positions in the DPP copolymer structure to locally enhance stability properties, enabling the material to withstand ambient conditions during fabrication while maintaining high charge carrier mobility

Inventive Principle:

Principle #3Local quality

Solution Approach 2:

The patent develops a composite copolymer structure combining DPP units with vinyl groups in E-configuration, creating a material that is both highly mobile and resistant to degradation during ambient fabrication processes

Inventive Principle:

Principle #40Composite materials

Data Source

PatentUS8558109B2Semiconductor composition for high performance organic devices

Publication Date: 2013.10.15 XEROX CORP

AI summary

A copolymer having a structure represented by:wherein R1 and R2 are independently selected from a hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Ar1 and Ar2 are independently an aromatic or heteroaromatic group including about 4 to about 30 carbon atoms, and can be optionally substituted; a and b are independently an integer from 1 to about 4; Ar3 and Ar4 are independently an aromatic or heteroaromatic group comprising about 4 to about 20 carbon atoms, and can be optionally substituted; c and e are independently an integer from about 0 to about 2; d is 1 to 4 and the carbon-carbon double bond is in the E-configuration; and n represents a number from 2 to about 5,000.