Indaceno Derivative Semiconductors for Liquid Processing

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Solution Overview

Problem

Existing organic semiconducting materials lack compatibility with liquid processing techniques and stability under ambient conditions, limiting their application in electronic devices such as OPVs, OFETs, and OPDs in terms of charge carrier mobility and mechanical flexibility.

Innovation Solution

Development of specific organic compounds with defined aromatic or heteroaromatic ring systems, incorporating various substituents and linkages, which can be processed using liquid techniques and exhibit high charge carrier mobility and stability, suitable for use in electronic devices like OFETs and OPVs.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional organic semiconducting materials are used, then device performance can be achieved, but compatibility with liquid processing techniques is poor

Engineering Contradiction:
Improvecompatibility with liquid processing techniquesVSAvoidstability under ambient conditions
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent modifies the chemical structure of organic semiconducting materials by introducing specific molecular weight ranges (1,000-1,000,000 g/mol) and incorporating particular functional groups and aromatic ring systems. These parameter changes enable the materials to be processed from solution while maintaining stability under ambient conditions, resolving the contradiction between ease of manufacture and reliability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite organic semiconducting materials that combine multiple functional components including electron-donating groups, electron-withdrawing groups, and specific aromatic ring systems within a single molecular structure. This composite approach allows the material to simultaneously exhibit solution processability and environmental stability, addressing both requirements.

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional organic semiconducting materials are used, then basic functionality is achieved, but charge carrier mobility is insufficient

Engineering Contradiction:
Improvecharge carrier mobilityVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent divides the organic semiconducting material into distinct functional segments: electron-donating groups (such as aromatic hydrocarbons), electron-withdrawing groups (such as heterocyclic rings with carbonyl or cyano groups), and connecting units. This segmentation allows each component to be optimized for its specific function while maintaining overall high charge carrier mobility through controlled molecular weight and architecture.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention applies local quality by positioning specific functional groups at particular locations within the molecular structure. Electron-donating groups are placed at terminal positions while electron-withdrawing groups are positioned to create appropriate electron transport pathways. This localized functional arrangement optimizes charge carrier mobility without requiring excessive overall molecular complexity.

Inventive Principle:
Principle #3Local quality

3Weight of moving object

If conventional organic semiconducting materials are used, then device functionality is achieved, but mechanical flexibility and weight are compromised

Engineering Contradiction:
Improvedevice weightVSAvoidmaterial stability
Core Design Contradiction:
Weight of moving objectVSStability of the object's composition

Solution Approach 1:

The patent specifies particular molecular weight ranges (1,000-1,000,000 g/mol) and incorporates flexible alkyl chain linkers between rigid aromatic cores. These parameter changes reduce the overall device weight while maintaining material stability through the balanced molecular architecture that prevents excessive chain entanglement and maintains crystalline order necessary for stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates organic semiconducting materials with inherent flexibility through the molecular structure design incorporating flexible alkyl chains and controlled molecular weights. This allows the materials to form mechanically flexible thin films that maintain compositional stability, enabling lightweight and bendable electronic devices.

Inventive Principle:
Principle #30Flexible shells and thin films

Data Source

PatentUS11778893B2Indaceno derivatives as organic semiconductors
Publication Date: 2023.10.03 CLAP CO LTD
  • US11778893B2 patent drawing
  • US11778893B2 patent drawing
  • US11778893B2 patent drawing

AI summary

The present invention provides compounds comprising at least one unit of formula (1) or (1′) as well as a process for the preparation of the compounds, intermediates of this process, electronic devices comprising the compounds, and the use of the compounds as semiconducting materials.