N-Dopant Compounds for Stable Organic Semiconductor Doping

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Solution Overview

Problem

Existing n-doping methods for organic semiconductors face challenges in achieving stable compounds that can effectively dope organic semiconductors in solution, leading to instability and inefficiency in forming charge-transfer salts for organic electronic devices.

Innovation Solution

Development of specific compounds, such as those of formulas (I) and (II), which are used to form charge-transfer salts by doping organic semiconductors, where R1, R2, R3, and R4 are alkyl or aromatic groups, and Ar1 and Ar2 are aromatic or heteroaromatic groups, allowing for activation to enhance n-doping efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing n-doping methods are used for organic semiconductors, then doping can be achieved, but the compounds are unstable and doping efficiency is low

Engineering Contradiction:
Improvestability of n-doped organic semiconductorVSAvoiddoping efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent changes the chemical parameters of the dopant compounds by introducing specific molecular structures (compounds of formula I and II with aromatic or heteroaromatic groups and alkyl substituents). These structural parameter changes result in compounds that are stable in solution while maintaining effective n-doping capability, resolving the contradiction between stability and doping efficiency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite charge-transfer salts formed by the interaction between the newly designed stable n-dopant compounds and organic semiconductor materials. These composite materials combine the stability of the dopant compounds with the semiconducting properties of the organic materials, achieving both reliability and productivity

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If stable n-dopant compounds are used, then solution stability is improved, but charge-transfer salt formation efficiency decreases

Engineering Contradiction:
Improvesolution stability of n-dopantVSAvoidcharge-transfer salt formation efficiency
Core Design Contradiction:
Stability of the object's compositionVSProductivity

Solution Approach 1:

The patent optimizes the chemical parameters of the dopant compounds (formula I and II) to achieve optimal balance between solution stability and reactivity. The specific molecular structure parameters allow the compounds to remain stable in solution while maintaining the ability to form charge-transfer salts efficiently upon activation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs preliminary action by using stable precursor compounds that can be stored and handled in solution without degradation. These precursors are then activated in situ to form the active n-dopant species, combining the benefits of solution stability with efficient charge-transfer salt formation

Inventive Principle:
Principle #10Preliminary action

Data Source

PatentUS11856845B2Compound
Publication Date: 2023.12.26 SUMITOMO CHEM CO LTD
  • US11856845B2 patent drawing
  • US11856845B2 patent drawing
  • US11856845B2 patent drawing

AI summary

Compound A compound of formula (I): (I) wherein R1 and R2 are each independently a linear, branched or cyclic C1-20alkyl group; and Ar1 and Ar2 are each independently an aromatic or heteroaromatic group which is unsubstituted or substituted with one or more substituents. The compound may be used in n-doping of an organic semiconductor. Such an n-doped organic semiconductor may be used in an organic electronic device, for example an electron injection layer of an organic light-emitting device.