Terphenylene Derivative for Oxidation-Resistant Organic Semiconductors
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Solution Overview
Problem
Current organic semiconductor materials face challenges in forming high-performance semiconductor active phases through coating processes due to issues like low solubility, oxidation, and the need for specialized fluorinating agents, which hinder the development of efficient and cost-effective organic thin-film transistors.
Innovation Solution
A novel terphenylene derivative with excellent oxidation resistance is developed, allowing for the formation of a semiconductor active phase via coating processes, and a tetrahaloterphenyl derivative is used as a precursor to produce this terphenylene derivative, enabling the creation of an oxidation-resistant organic semiconductor material.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If a coating process is used to prepare organic semiconductor active phase, then production costs are reduced and processing is simplified, but it becomes increasingly difficult to form high-performance semiconductor active phase as material performance increases
Solution Approach 1:
The patent modifies molecular parameters of the semiconductor material by introducing specific substituents (alkyl groups, alkoxy groups, aryl groups) at defined positions of the terphenylene core structure. These parameter changes enhance solubility while maintaining crystalline packing, enabling coating processability without sacrificing device performance
Solution Approach 2:
The patent creates composite molecular structures by combining a rigid terphenylene core with flexible substituent groups. This composite approach yields materials that exhibit both the high carrier mobility of crystalline materials and the solubility required for coating processes
2Reliability
If pentacene is used as organic semiconductor material, then high carrier mobility is achieved, but low solubility and easy oxidation require high-temperature heating and special processing conditions
Solution Approach 1:
The patent applies local quality modification by introducing specific functional groups at particular positions of the terphenylene molecule. The core structure maintains high carrier mobility characteristics, while peripheral substituents provide enhanced solubility and oxidation resistance, allowing room-temperature processing
Solution Approach 2:
The patent converts the harmful effect of strong molecular cohesiveness (which causes low solubility) into a beneficial feature by strategically placing substituents that maintain crystalline packing ability while improving solubility. The rigid core provides stability and high mobility, while substituents prevent aggregation and enable coating processing
3Adaptability or versatility
If fluorine substitution is performed to obtain n-type semiconductor properties, then n-type conductivity is achieved, but special fluorinating agents are required and yield is low
Solution Approach 1:
The patent replaces expensive and complex fluorinating agents with common, inexpensive substituents (alkyl, alkoxy, aryl groups) that can be introduced via standard organic synthesis methods. This disposable approach uses readily available reagents to achieve the desired semiconductor properties without requiring specialized fluorination chemistry
4Reliability
If unsubstituted terphenylene is used, then rigid rod-like structure with pentacene-like properties is obtained, but instability and complex synthesis with photoreaction steps make it industrially unpreferable
Solution Approach 1:
The patent applies preliminary action by pre-installing stable substituent groups on the terphenylene core during synthesis. This preliminary modification prevents decomposition and instability issues of unsubstituted terphenylene, while the substituents facilitate subsequent purification and processing steps
Solution Approach 2:
The patent extracts the problematic photoreactive and unstable portions from the molecule by replacing hydrogen atoms with stable substituents. This extraction of instability eliminates the need for photoreaction steps and complex synthesis procedures while maintaining the rigid rod-like structure necessary for high performance
Data Source
AI summary
An object of the present invention relates to provision of a terphenylene derivative having excellent oxidation resistance and capable of forming a semiconductor active phase by a coating process and an oxidation-resistant organic semiconductor material using the same, as well as an organic thin film.The invention relates to production of a terphenylene derivative represented by the formula (1) by tetralithiating a tetrahaloterphenyl derivative with a lithiating agent and subsequently treating the resulting compound with a copper compound:[ka 1]wherein R1 to R14 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, an aryl group having 4 to 30 carbon atoms, an alkynyl group having 3 to 20 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkyl group having 1 to 20 carbon atoms or a halogenated alkyl group having 1 to 20 carbon atoms, or a diarylamino group having 8 to carbon atoms; and l, m, and n each represents an integer of 0 or 1.