Tetraazapyrene Core Organic Semiconductors for Charge Transport

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Solution Overview

Problem

There is a need for improved n-type organic semiconducting materials with enhanced properties such as charge-carrier mobility, on/off ratio, oxidative stability, and long lifetime for use in electronic devices, as current materials do not meet the requirements for advanced applications like organic photodetectors and solar cells.

Innovation Solution

Development of organic semiconducting compounds with a tetraazapyrene core, specifically designed to improve charge transport and stability, which can be used in blends with other compounds to create materials for various electronic devices, including organic photodetectors and solar cells.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Speed

If conventional n-type organic semiconducting materials are used, then device fabrication is simpler, but charge-carrier mobility is insufficient for advanced applications

Engineering Contradiction:
Improvecharge-carrier mobilityVSAvoidoxidative stability
Core Design Contradiction:
SpeedVSReliability

Solution Approach 1:

The patent modifies the molecular structure of n-type organic semiconducting materials by introducing a tetraazapyrene core with specific substituents (R1-R6 groups), changing chemical parameters to achieve both high charge-carrier mobility and oxidative stability simultaneously

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures combining the tetraazapyrene core with various functional groups (electron-withdrawing groups, aromatic hydrocarbyl groups, heteroaryl groups) to achieve synergistic effects that improve both charge transport and stability

Inventive Principle:
Principle #40Composite materials

2Reliability

If existing organic semiconducting materials are used, then material synthesis is easier, but on/off ratio is insufficient for high-performance devices

Engineering Contradiction:
Improveon/off ratioVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The molecular structure is segmented into distinct functional modules: the tetraazapyrene core (formula I) and separate substituent groups (R1-R6), allowing systematic optimization of each module's contribution to on/off ratio while managing overall complexity

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Different regions of the molecule are assigned specific functions: the core provides charge transport capability while specific substituents (electron-withdrawing groups at R2-R4) enhance electron affinity and on/off ratio, creating local functional optimization

Inventive Principle:
Principle #3Local quality

3Duration of action of stationary object

If current n-type materials are used, then device manufacturing is simpler, but lifetime is insufficient for long-term applications

Engineering Contradiction:
Improvedevice lifetimeVSAvoidprocessability
Core Design Contradiction:
Duration of action of stationary objectVSEase of manufacture

Solution Approach 1:

The patent optimizes molecular parameters including molecular weight, glass transition temperature, and solubility by selecting specific substituent groups (R1-R6) to achieve both long device lifetime and good processability through solution-based fabrication methods

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS11098050B2Organic semiconducting compounds comprising a tetraazapyrene core
Publication Date: 2021.08.24 MERCK PATENT GMBH
  • US11098050B2 patent drawing
  • US11098050B2 patent drawing
  • US11098050B2 patent drawing

AI summary

The present invention relates to organic semiconducting compounds of formula (I) wherein X1 is C, Si or Ge; X2 is 0, S or Se; and X3 is N or P as well as to organic electronic devices comprising such organic semiconducting compounds. (I)