π-Extended Quinoid Compounds for Organic Electronics
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Solution Overview
Problem
There is a need for n-type organic semiconducting compounds with improved properties such as high charge carrier mobility, solubility, and stability for use in organic electronic devices like OPV cells and OFETs, as existing n-type OSCs are limited in commercial potential and performance.
Innovation Solution
Development of π-extended ω-disubstituted dicyanomethylene quinoid compounds that serve as electron-deficient n-type semiconductors, offering enhanced electron mobility and solubility, suitable for mass production and integration in organic electronic devices.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional n-type OSCs are used, then device fabrication is possible, but charge carrier mobility is low
Solution Approach 1:
The patent modifies molecular parameters by introducing π-extended quinoid structures with dicyanomethylene groups at ω-positions, changing the electronic and structural properties to achieve higher charge carrier mobility while maintaining synthetic feasibility through established organic synthesis methods
Solution Approach 2:
The invention creates composite molecular structures combining quinoid cores with dicyanomethylene substituents and various aromatic groups, producing n-type OSCs with superior electron mobility that overcome the limitations of conventional single-structure materials
2Ease of manufacture
If conventional n-type OSCs are used, then device fabrication is possible, but solubility in organic solvents is poor
Solution Approach 1:
The patent introduces solubilizing groups at specific positions on the quinoid core while maintaining the essential π-conjugated structure, creating local modifications that enhance solubility without compromising the overall structural organization required for semiconductor functionality
Solution Approach 2:
By modifying molecular parameters through substitution patterns and choosing appropriate side chains, the patent achieves improved solubility in organic solvents while preserving the structural characteristics necessary for effective charge transport
3Reliability
If conventional n-type OSCs are used, then basic semiconductor function is achieved, but stability and lifetime are insufficient
Solution Approach 1:
The patent divides the semiconductor molecule into functional segments: a stable quinoid core providing structural integrity, dicyanomethylene groups for electron affinity, and substituent groups for stability enhancement, allowing each segment to contribute specifically to overall device performance and longevity
Solution Approach 2:
By constructing composite molecular architectures with multiple functional groups strategically positioned, the patent creates n-type OSCs with enhanced oxidative and thermal stability that extend device lifetime, balancing structural complexity with performance benefits
4Reliability
If π-extended structures are introduced to improve electron mobility, then charge carrier mobility increases, but molecular weight and processing difficulty increase
Solution Approach 1:
The patent optimizes the extent of π-conjugation by carefully selecting the size and arrangement of aromatic groups on the quinoid core, achieving sufficient electron mobility while controlling molecular weight to maintain processability and reduce synthesis complexity
Data Source
AI summary
The invention relates to novel organic semiconducting compounds containing a π-extended ω-disubstituted dicyanomethylene quinoid structure, to methods for their preparation and educts or intermediates used therein, to compositions, polymer blends and formulations containing them, to the use of the compounds, compositions and polymer blends as organic semiconductors in, or for the preparation of, organic electronic (OE) devices, especially organic photovoltaic (OPV) devices, perovskite-based solar cell (PSC) devices, organic photodetectors (OPD), organic field effect transistors (OFET) and organic light emitting diodes (OLED), and to OE, OPV, PSC, OPD, OFET and OLED devices comprising these compounds, compositions or polymer blends.