Fused Polycyclic Aromatic Compound for Soluble Heat-Stable Thin Films
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Solution Overview
Problem
Existing fused polycyclic aromatic compounds, such as DNTT derivatives, face challenges with poor solubility in organic solvents, leading to difficulties in manufacturing organic semiconductor layers via solution processes, and their semiconductor characteristics degrade during thermal annealing, while their synthesis methods are not versatile and result in high dark electric current in photoelectric conversion elements.
Innovation Solution
A novel fused polycyclic aromatic compound with a specific structure, allowing for the introduction of various substituents through a simple synthesis method, forming organic thin films with excellent heat resistance and high bright-dark electric current ratios in low voltage regions, is developed, enabling the creation of field-effect transistors and photoelectric conversion elements with improved performance.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If DNTT derivatives are used as organic electronics compounds, then excellent electric charge mobility is achieved, but poor solubility in organic solvents prevents manufacturing by solution processes
Solution Approach 1:
The patent modifies the molecular structure parameters of DNTT derivatives by introducing specific substituent groups (aromatic hydrocarbon groups with 9-18 carbon atoms) to change the solubility characteristics while preserving the core electronic properties. This structural parameter change enables the compound to be processed by solution methods without sacrificing charge mobility.
2Ease of manufacture
If aromatic groups with large number of ring structures are substituted in DNTT skeleton, then solubility improves, but sublimation temperature increases causing thermal decomposition in vapor deposition process
Solution Approach 1:
The patent carefully selects aromatic hydrocarbon groups with controlled carbon atom counts (9-18 atoms) to achieve optimal balance. This parameter control ensures sufficient solubility improvement while keeping the sublimation temperature below the decomposition point, enabling successful vapor deposition processing.
3Ease of manufacture
If DNTT derivatives are processed through thermal annealing, then organic semiconductor layer is formed, but semiconductor characteristics decrease remarkably
Solution Approach 1:
The patent introduces aromatic substituents that modify the thermal stability parameters of the DNTT derivative. These structural modifications raise the thermal stability threshold, allowing the material to withstand thermal annealing temperatures without degrading its semiconductor characteristics, thus maintaining high charge mobility after thermal processing.
4Ease of manufacture
If existing synthesis methods are used for DNTT derivatives, then compound is obtained, but synthesis method has low versatility and requires advance substitution at 2-position or 3-position of naphthalene skeleton
Solution Approach 1:
The patent inverts the conventional synthesis approach by introducing substituents at the 1-position of the naphthalene skeleton rather than the traditional 2-position or 3-position. This inverted substitution pattern provides superior synthesis versatility and simplifies the manufacturing process while maintaining the desired electronic properties of the DNTT derivative.
Data Source
AI summary
The present invention includes a fused polycyclic aromatic compound represented by general formula (1), where in formula (1), one among R1 and R2 is represented by general formula (2) and represents a substituent having three to five ring structures, and the other among R1 and R2 represents a hydrogen atom, where in formula (2), n represents an integer of 0-2, R3 represents a divalent linking group obtained by removing two hydrogen atoms from benzene or naphthalene, R4 represents a divalent linking group obtained by removing two hydrogen atoms from an aromatic ring of an aromatic hydrocarbon, and when n is 2, a plurality of R4's may be the same as or different from each other, R5 represents an aromatic hydrocarbon group.