Fused Polycyclic Aromatic Compound for Organic Semiconductors

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Solution Overview

Problem

Current methods for producing organic semiconductor materials with high electron field-effect mobility are complex and inefficient, often requiring multistage synthesis and resulting in materials with poor atmospheric stability due to a high number of fused rings, which hinders practical application.

Innovation Solution

A novel fused polycyclic aromatic compound with a benzodichalcogenophenobenzodichalcogenophene skeleton is developed, featuring additional fused rings that enhance intermolecular interaction and stability, produced through a simplified method involving the addition of an alkyl metal reagent and a liquid reagent containing chalcogen atoms, allowing for high-purity compounds with improved electron field-effect mobility.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If the fused-ring number is increased to improve electron field-effect mobility, then the electron field-effect mobility is improved, but the solubility and atmospheric stability deteriorate

Engineering Contradiction:
Improveelectron field-effect mobilityVSAvoidatmospheric stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The invention changes the chemical structure parameters by introducing specific heteroatoms (chalcogen atoms) and substituent groups at controlled positions in the fused ring system. This modifies the electronic properties and intermolecular interactions to achieve high mobility while maintaining stability through optimized molecular geometry and electronic distribution

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining the BXBX skeleton with additional aromatic rings and heterocyclic substituents. This composite approach allows the molecule to exhibit both high electron field-effect mobility (from the extended π-conjugation) and atmospheric stability (from the stable heterocyclic components) simultaneously

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional multistage synthesis methods are used to produce compounds with high fused-ring numbers, then compounds with high electron field-effect mobility can be obtained, but the manufacturing complexity and time increase

Engineering Contradiction:
Improveelectron field-effect mobilityVSAvoidsynthesis efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The invention performs preliminary structural design by establishing the stable BXBX core skeleton first, then systematically adding aromatic rings and heterocyclic substituents in predetermined positions. This preliminary action reduces the need for multiple purification and optimization stages, streamlining the synthesis process

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention segments the synthesis process into modular steps: (1) forming the BXBX core, (2) adding aromatic rings at specific positions, and (3) introducing heterocyclic substituents. This segmentation allows each step to be optimized independently and facilitates easier purification and quality control

Inventive Principle:
Principle #1Segmentation

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 new compound achieves high electron field-effect mobility and stability, enabling the development of efficient organic semiconductor devices with improved performance and durability, suitable for applications in thin film transistors and light-emitting devices.

Implementation Method 1

adding an alkyl metal reagent and a liquid reagent containing chalcogen atoms

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

adding an alkyl metal reagent and a liquid reagent containing chalcogen atoms

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentUS8232546B2Fused polycyclic aromatic compound, process for producing the same, and use thereof
Publication Date: 2012.07.31 NIPPON KAYAKU CO LTD
  • US8232546B2 patent drawing
  • US8232546B2 patent drawing
  • US8232546B2 patent drawing

AI summary

In one embodiment of the present invention, a novel fused polycyclic aromatic compound of the present invention is (a) a compound including a benzodichalcogenophenobenzodichalcogenophene (BXBX) skeleton further having an aromatic ring(s) located outside the BXBX skeleton, or (b) a compound including a BXBX skeleton in which a benzene ring is substituted with a heterocyclic ring. The compound can strengthen intermolecular interaction due to greater π electron orbits. This improves an electron field effect mobility of an organic semiconductor device that is manufactured by use of the compound as an organic semiconductor material. Further, since the number of fused rings included in the compound is small, the compound does not cause problems that generally occur in compounds having an extremely large number of fused rings, i.e., poor solubility in solvent and poor atmospheric stability due to high affinity to oxygen. As a result, the fused polycyclic aromatic compound of the present invention can be preferably used as an organic semiconductor material.