Organic Semiconductor Compounds with Segmented Perylene Cores

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Solution Overview

Problem

The development of n-type organic semiconductor materials has lagged behind p-type materials, with existing n-type semiconductors exhibiting poor electrical performance, instability in air, and limited accessibility, hindering their use in efficient logic circuits and organic solar cells.

Innovation Solution

The development of novel organic compounds with specific chemical structures, such as those described by formulas (I), (II), (III), and (IV), which possess high electron mobility, excellent air stability, and can be synthesized through easily accessible processes, allowing for their use as p-type, n-type, or ambipolar semiconductor materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If perylene building blocks are used for n-type organic semiconductors, then electron mobility is improved, but structural rigidity and moderate solubility limit structural changes and material accessibility

Engineering Contradiction:

Improveelectron mobilityVSAvoidstructural changes accessibility

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The perylene core is divided into separate functional units by introducing flexible spacers and side chains. This segmentation allows the rigid perylene unit to maintain electron mobility while the flexible connecting units enable structural modifications and improve solubility, thus resolving the contradiction between reliability and adaptability.

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The patent creates composite molecular structures combining rigid perylene units with flexible side chains and spacer groups. This composite approach allows the material to simultaneously exhibit high electron mobility from the perylene core while gaining structural versatility and solubility from the flexible components, resolving the technical contradiction.

Inventive Principle:

Principle #40Composite materials

2Reliability

If fluorinated side chains are introduced to improve electron mobility, then air stability is improved, but device complexity increases

Engineering Contradiction:

Improveair stabilityVSAvoidmolecular structure complexity

Core Design Contradiction:

ReliabilityVSDevice complexity

Solution Approach 1:

Fluorination is applied locally to specific side chain positions rather than uniformly throughout the entire molecule. This localized approach provides the air stability benefits of fluorinated groups while minimizing the increase in molecular complexity, as only specific regions of the molecule are modified with fluorinated side chains.

Inventive Principle:

Principle #3Local quality

3Adaptability or versatility

If n-type organic semiconductor materials are developed for logic circuits, then electronic application versatility is improved, but electrical performance and stability are insufficient

Engineering Contradiction:

Improveapplication versatilityVSAvoidelectrical performance

Core Design Contradiction:

Adaptability or versatilityVSReliability

Solution Approach 1:

The patent systematically varies key molecular parameters including side chain length, degree of fluorination, and spacer group composition to optimize the balance between electrical performance and application versatility. By tuning these parameters, the material achieves both high electron mobility for electrical performance and structural diversity for application versatility in logic circuits and solar cells.

Inventive Principle:

Principle #35Parameter changes

Data Source

PatentUS9508936B2Organic semiconductor material

Publication Date: 2016.11.29 USINVEST LLC

AI summary

A novel compound useful as organic semiconductor material, and semiconductor devices containing such organic semiconductor material are described.