Perylenetetracarboxylic Diimide Semiconductor Solubility and Mobility

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Solution Overview

Problem

Current polymer solar cells face limitations in energy conversion efficiency due to low carrier mobility, mismatched spectral response with solar radiation, and poor solubility and film-forming performance of perylenetetracarboxylic diimide materials, which restrict their application and efficiency.

Innovation Solution

A perylenetetracarboxylic diimide organic semiconductor material with a dithieno[3,2-b:2',3'-d]silole unit is developed, enhancing solubility and carrier mobility through structural modifications and copolymerization, extending absorption to the near-infrared region and improving charge transfer properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If perylenetetracarboxylic diimide and its derivatives are used as organic semiconductor materials, then electron mobility and light stability are improved, but solubility and film-forming performance deteriorate

Engineering Contradiction:
Improveelectron mobilityVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the molecular structure of perylenetetracarboxylic diimide by introducing dithieno[3,2-b:2′,3′-d]silole units and various substituent groups (alkyl, alkoxy, aryl) to change the physical and chemical parameters of the material. This structural modification maintains the core electron-transporting properties while improving solubility through enhanced molecular flexibility and reduced intermolecular interactions.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures by combining perylenetetracarboxylic diimide core with dithieno[3,2-b:2′,3′-d]silole units and various functional groups. This composite approach integrates the high electron mobility of the diimide core with the solubility-enhancing properties of the silole and substituent groups, achieving both improved reliability and ease of manufacture.

Inventive Principle:
Principle #40Composite materials

2Reliability

If perylenetetracarboxylic diimide and its derivatives are used, then electron affinity is improved, but absorption range and spectral matching with sunlight deteriorate

Engineering Contradiction:
Improveelectron affinityVSAvoidabsorption range
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent extends the absorption spectrum of perylenetetracarboxylic diimide by introducing conjugated dithieno[3,2-b:2′,3′-d]silole units and various aromatic substituent groups. These modifications change the HOMO-LUMO energy gap and extend absorption into the near-infrared region while maintaining the high electron affinity of the diimide core through appropriate substituent selection.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures that combine the electron-accepting diimide core with electron-donating or conjugated groups. This composite approach enables the material to maintain high electron affinity from the diimide core while achieving broadened absorption spectrum from the conjugated silole and aromatic groups, improving spectral matching with sunlight.

Inventive Principle:
Principle #40Composite materials

3Ease of manufacture

If conventional polymer solar cell materials are used, then production cost is reduced, but energy conversion efficiency deteriorates

Engineering Contradiction:
Improveproduction costVSAvoidenergy conversion efficiency
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent develops composite polymer materials combining perylenetetracarboxylic diimide with dithieno[3,2-b:2′,3′-d]silole units and various functional groups. This composite structure maintains the low-cost advantage of organic polymers while achieving enhanced energy conversion efficiency through improved charge transport, broadened light absorption, and better phase separation morphology.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent modifies the molecular parameters of conventional polymer solar cell materials by incorporating high-performance perylenetetracarboxylic diimide core structures with optimized side chains and conjugated units. This parameter optimization enables the material to maintain processability and low cost while achieving energy conversion efficiencies comparable to or exceeding conventional materials.

Inventive Principle:
Principle #35Parameter changes

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 modified material exhibits improved solubility, strong absorbance, and increased sunlight utilization, enhancing the energy conversion efficiency and stability of organic solar cells.

Implementation Method 1

the energy conversion efficiency of the blend system of PTB7 and PC71BM has attained 7.4%... the photoinduced electron transfer phenomenon between the conjugated polymer and C60... the modified material exhibits improved solubility, strong absorbance, and increased sunlight utilization, enhancing the energy conversion efficiency

Methodology Applied
Scientific EffectPhotoelectric conversion: Photovoltaic Effect

Implementation Method 2

Since N.S. Sariciftci et al. reported in 1992 in the SCIENCE about the photoinduced electron transfer phenomenon between the conjugated polymer and C60

Methodology Applied
Scientific EffectPhotoinduced electron transfer: Photoelectric Effect

Implementation Method 3

high electron mobility along the stacking direction because of the π-π stacking between its big conjugated π bonds

Methodology Applied
Scientific Effectπ-π stacking:

Data Source

PatentEP2615097B1Perylenetetracarboxylic acid diimide organic semiconductive material, preparation method and use thereof
Publication Date: 2015.03.04 OCEANS KING LIGHTING SCI&TECH CO LTD
  • EP2615097B1 patent drawingFigure 1~2
  • EP2615097B1 patent drawingFigure 3
  • EP2615097B1 patent drawing

AI summary

Disclosed is a perylenetetracarboxylic acid diimide organic semiconductive material represented by the following formula (I), which belongs to the field of photoelectric material. In formula (I), n is an integer of 1-100, R1, R2 or R3 is hydrogen, C1-C20 alkyl, C1-C20 alkoxyl, phenyl or alkoxyphenyl, R4 or R5 is C1-C20 alkyl, R6 or R7 is hydrogen, C1-C20 alkyl, C1-C20 alkoxyl or phenyl. The preparation method of said perylenetetracarboxylic acid diimide organic semiconductive material and the use thereof are also disclosed.