Bithiophene Derivatives for Air-Stable Organic Semiconductors

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Solution Overview

Problem

Conventional organic semiconductor materials, such as pentacyclic molecules, oxidize in air, leading to a decline in electrical performance over time, necessitating the development of novel materials with improved stability and solubility for efficient large-area fabrication.

Innovation Solution

A soluble bithiophene derivative with long alkyl chains and sulfur atoms is introduced, facilitating molecular arrangement regularity and solubility, enabling high carrier mobility and air stability through a liquid-liquid low-temperature process for large-area fabrication.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If pentacyclic molecule materials are used as organic semiconductor materials, then electrical performance can be achieved, but the materials oxidize in air over time causing electrical performance to decline

Engineering Contradiction:
Improveelectrical performance stabilityVSAvoidoxidation resistance
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical parameters of the semiconductor material by introducing sulfur atoms at specific positions in the bithiophene derivative structure. This structural modification alters the material's chemical stability and oxidation resistance while maintaining electrical performance, directly resolving the contradiction between reliability and compositional stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining bithiophene core with long alkyl chains (C8-25) and sulfur-containing groups. This composite approach integrates multiple functional components: the bithiophene provides electrical conductivity, the long alkyl chains provide solubility and stability, and the sulfur atoms enhance molecular arrangement and oxidation resistance, collectively solving both reliability and stability issues.

Inventive Principle:
Principle #40Composite materials

2Productivity

If conventional organic semiconductor materials are used, then device fabrication can proceed, but solubility is poor limiting large-area fabrication capabilities

Engineering Contradiction:
Improvelarge-area fabrication capabilityVSAvoidsolubility
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes the physical parameter of solubility by attaching long alkyl chains (C8-25) to the bithiophene core structure. This structural modification significantly improves the material's solubility in common organic solvents, enabling solution-based processing methods for large-area fabrication while maintaining the material's semiconductor properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent enables liquid-liquid processing methods by improving material solubility, allowing the use of solution-based deposition techniques such as spin-coating, dip-coating, or inkjet printing for large-area fabrication. This transitions from solid-state processing to fluid-based processing, enhancing manufacturability and scalability.

Inventive Principle:
Principle #29Pneumatics and hydraulics

3Ease of manufacture

If soluble bithiophene derivatives with long alkyl chains are used, then solubility and molecular arrangement regularity improve, but molecular structure complexity increases

Engineering Contradiction:
Improvesolubility and molecular arrangementVSAvoidmolecular structure
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent segments the molecular structure into distinct functional modules: a bithiophene core unit, long alkyl chain segments (C8-25), and sulfur-containing functional groups. This segmentation allows each component to perform its specific function independently while simplifying the overall design and synthesis approach despite the increased molecular complexity.

Inventive Principle:
Principle #1Segmentation

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 bithiophene derivative exhibits high carrier mobility, stability against oxidation, and simplified fabrication steps, enhancing the electrical performance and manufacturing convenience of semiconductor devices.

Implementation Method 1

the sulfur atoms are conducted into the molecule structure of the material, advancing the regularity of molecular arrangements and the solubility of the material through the strong interaction force between the sulfur atoms and Van der Waals force formed between the long alkyl chains

Methodology Applied
Scientific EffectVan der Waals force: Van der Waals Force

Data Source

PatentUS8759543B2Bithiophene derivatives and semiconductor devices comprising the same
Publication Date: 2014.06.24 IND TECH RES INST
  • US8759543B2 patent drawing
  • US8759543B2 patent drawing
  • US8759543B2 patent drawing

AI summary

In an embodiment of the disclosure, a bithiophene derivative is provided. The bithiophene derivative has formula (I):In formula (I), R is C8-25 alkyl, and A includesIn another embodiment of the disclosure, a semiconductor device including the bithiophene derivative is further provided.