Asymmetric Perylene Diimide Compounds for Organic Thin-Film Transistors
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Solution Overview
Problem
Existing organic thin film transistors using compounds with N-functionalized fused ring imides have insufficient carrier mobility due to low solubility in organic solvents, which hinders their performance in modern applications.
Innovation Solution
A compound with a perylene diimide skeleton, where at least one oxygen atom in the imide skeleton is substituted with a sulfur atom, selenium, or tellurium, and the structure is made asymmetric by introducing a ring structure, enhancing solubility and carrier mobility.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If a compound with N-functionalized fused ring imide is used in an organic thin film transistor, then the device can be manufactured with low cost and simple process, but the carrier mobility is insufficient due to low solubility in organic solvents
Solution Approach 1:
The patent applies asymmetry by introducing a ring structure at the R1 or R2 position of the perylene diimide core, creating an asymmetric molecular geometry. This asymmetric structure disrupts the symmetric packing of molecules in the solid state, thereby improving solubility in organic solvents while maintaining good carrier mobility in the thin film transistor device.
Solution Approach 2:
The patent changes the molecular parameters by substituting oxygen atoms in the imide skeleton with sulfur, selenium, or tellurium atoms. This parameter change (atomic substitution) modifies the molecular weight, polarizability, and intermolecular interaction, leading to improved solubility while preserving the electronic properties necessary for high carrier mobility.
2Reliability
If the solubility of the organic semiconductor compound is improved by molecular modification, then the carrier mobility increases, but the molecular structure becomes more complex
Solution Approach 1:
The patent segments the molecular modification into two distinct parts: (1) the core perylene diimide structure which is maintained for electronic functionality, and (2) the substituent groups (ring structures at R1/R2 and heteroatom substitutions at X1-X4) which are optimized for solubility. This segmentation allows independent optimization of electronic properties and solubility without excessive molecular complexity.
Solution Approach 2:
The patent creates a composite molecular structure combining the perylene diimide core with additional ring structures and heteroatom substitutions. This composite approach integrates multiple functional elements (electron transport capability from the core, solubility enhancement from ring structures and heteroatoms) into a single molecule, achieving both high carrier mobility and good solubility with controlled complexity.
Data Source
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Figure 4A~5
AI summary
An object of the present invention is to provide an organic thin film transistor that has an organic semiconductor film manufactured by using a compound having excellent solubility to an organic solvent and that has excellent carrier mobility, a novel compound, an organic thin film transistor material, an organic semiconductor film, an organic thin film transistor composition, and a method of manufacturing an organic thin film transistor using this. The organic thin film transistor according to the present invention has an organic semiconductor film containing a compound represented by Formula (1).