Solubilized Pentacene Semiconductors for Printable Organic Electronics

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Solution Overview

Problem

Current organic semiconductor materials face challenges in commercialization due to limitations in processability, particularly insolubility and photostability, which hinder the large-scale production of devices like OTFTs, OPVs, and OLEDs.

Innovation Solution

Development of polymeric and molecular semiconductors with specific structures, such as those represented by formulas (I) and (II), which exhibit excellent charge transport characteristics, solubility, and photostability, enabling high-performance field-effect devices and efficient fabrication of organic electronic devices.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If pentacene is used to achieve high hole mobility (>5 cm²/V·s), then charge transport performance is improved, but processability via printing methodologies deteriorates due to insolubility

Engineering Contradiction:
Improvecharge transport performanceVSAvoidprocessability via printing methodologies
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the molecular structure of pentacene by introducing solubilizing side chains and functional groups, changing physical parameters (solubility, molecular weight) while maintaining the core aromatic framework that provides high hole mobility. This allows the material to be processed via printing methodologies while retaining excellent charge transport characteristics.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite semiconductor materials by combining pentacene core units with various solubilizing moieties and functional groups. These composite structures integrate the high charge transport properties of pentacene with the processability advantages of soluble polymers and molecules, enabling both high performance and printability.

Inventive Principle:
Principle #40Composite materials

2Reliability

If organic semiconductor materials are designed for high performance, then device performance is improved, but photostability deteriorates

Engineering Contradiction:
Improvedevice performanceVSAvoidphotostability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent addresses photostability issues by incorporating photostabilizing functional groups and molecular structures that convert harmful photodegradation pathways into beneficial or neutral processes. The molecular designs include features that dissipate photogenerated energy safely, preventing degradation while maintaining high device performance.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The invention modifies the electronic and structural parameters of organic semiconductor materials to improve photostability. By adjusting HOMO-LUMO energy levels, molecular rigidity, and conjugation lengths, the materials achieve both high performance and enhanced resistance to photodegradation.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If new polymeric and molecular semiconductors are synthesized to improve processability, then ease of manufacture is improved, but achieving well-balanced semiconducting properties becomes more difficult

Engineering Contradiction:
ImproveprocessabilityVSAvoidachieving well-balanced semiconducting properties
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent employs modular molecular design where semiconductor-active units are segmented from solubilizing and functional groups. This segmentation allows independent optimization of charge transport properties and processability, then combines them through standardized coupling methods to achieve well-balanced materials without excessive complexity.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention develops universal building blocks and functional groups that can be applied across multiple semiconductor materials to achieve consistent performance and processability. These multi-functional modules simplify the synthesis of well-balanced semiconductors by reducing the need to redesign entire molecular structures for each application.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Data Source

PatentUS9035004B2Semiconducting compounds and devices incorporating same
Publication Date: 2015.05.19 USINVEST LLC
  • US9035004B2 patent drawing
  • US9035004B2 patent drawing
  • US9035004B2 patent drawing

AI summary

Disclosed are molecular and polymeric compounds having desirable properties as semiconducting materials. Such compounds can exhibit desirable electronic properties and possess processing advantages including solution-processability and/or good stability.