Coating Organic Semiconductor Layer Balancing Mobility and Solubility

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Solution Overview

Problem

Existing small-molecule organic semiconductor materials face challenges in achieving high carrier mobility, high heat resistance, and high solubility, which are essential for efficient device fabrication processes, particularly in organic thin film transistors.

Innovation Solution

A novel aromatic compound with specific substituents, represented by formulas (1-I) and (1-II), is developed to enhance carrier mobility, heat resistance, and solubility, suitable for use in organic semiconductor layers and transistors.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If alkyl groups are introduced to improve solubility, then solubility increases, but carrier mobility and heat resistance decrease

Engineering Contradiction:
ImprovesolubilityVSAvoidcarrier mobility
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The invention changes the chemical structure parameters by replacing alkyl groups with aromatic substituents (formula 2) containing specific ring systems and substituents (formula 3), which fundamentally alters the molecular properties to achieve simultaneous improvement in solubility, carrier mobility, and heat resistance

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining the core semiconductor skeleton (formula 1) with specifically designed aromatic substituent groups (formula 2), where the substituent itself contains nested structural elements (formula 3), effectively creating a multi-component composite material that achieves multiple performance targets simultaneously

Inventive Principle:
Principle #40Composite materials

2Reliability

If aromatic substituents are introduced to enhance carrier mobility through π-stacking, then carrier mobility increases, but solubility decreases significantly

Engineering Contradiction:
Improvecarrier mobilityVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The invention optimizes the aromatic substituent structure by specifying particular ring systems (thiophene, furan, selenophene, carbazole, indole, oxazole, isoxazole, pyridine) and their substitution patterns, which modifies the balance between π-stacking capability and solubility, achieving both high carrier mobility and high solubility simultaneously

Inventive Principle:
Principle #35Parameter changes

3Reliability

If small-molecule semiconductors with rod-shaped molecular major axis are used to achieve high carrier mobility, then carrier mobility increases, but solubility remains low

Engineering Contradiction:
Improvecarrier mobilityVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The invention segments the molecule into distinct functional regions: the rod-shaped core (formula 1) for carrier mobility and the aromatic substituent groups (formulae 2 and 3) for solubility, allowing each segment to independently contribute its beneficial properties without compromising the other

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention applies local quality by concentrating the solubility-enhancing aromatic groups at specific positions (2,7-positions of the core structure) while maintaining the rod-shaped core structure for charge transport, creating different functional zones within the same molecule

Inventive Principle:
Principle #3Local quality

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The aromatic compound provides high carrier mobility and heat resistance, enabling the production of organic thin film transistors with excellent semiconductor properties through coating processes.

Implementation Method 1

When the aromatic compound according to the present invention is used, it is possible to provide a coating-type organic semiconductor material having high carrier mobility with high heat resistance and high solubility

Methodology Applied
Scientific EffectSelf-assembly: Self-Assembly

Data Source

PatentEP4647432A1Aromatic compound, organic semiconductor layer, and organic thin film transistor
Publication Date: 2025.11.12 TOSOH CORP
  • EP4647432A1 patent drawingFigure 1
  • EP4647432A1 patent drawing
  • EP4647432A1 patent drawing

AI summary

Provided is an aromatic compound that is a coating-type organic semiconductor material having high carrier mobility, high heat resistance and high solubility. The aromatic compound is indicated by formula (1-I) or (1-II) below, where Ar denotes, for example, a monocyclic ring, X1 and X2 denote, for example, oxygen atoms, Y1 and Y2 denote, for example, CR6, R1 to R6 denote, for example, hydrogen atoms, and at least one of R1 to R6 is a group represented by formula (2) below. k and m denote 0 or 1, n denotes an integer of 1 to 8, l denotes an integer of 1 to 20, and Z1 and Z2 denote, for example, hydrogen atoms.