Isoindigo Conjugated Polymer Regioregularity and Efficiency

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Solution Overview

Problem

Current organic solar cells and semiconductor devices face limitations due to the lack of materials containing isoindigo units, which restrict their energy conversion efficiency and application scope.

Innovation Solution

A conjugated polymer containing isoindigo units is developed, prepared through a method involving specific organic palladium and phosphine ligand catalysis in an anaerobic environment, with a Heck reaction process, and purified to enhance solubility, film-forming properties, and thermal stability, broadening absorption range and improving energy conversion efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional polymerization methods are used to synthesize polyisoindigo, then the polymer can be produced, but the molecular weight is low and the regioregularity is poor

Engineering Contradiction:
ImproveregioregularityVSAvoidpolymerization method complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent changes the chemical parameters of the polymerization reaction by using specific catalysts (AlEt2Cl, AlEt2Br, or AlEt2I) in toluene solvent at controlled temperatures (0°C to room temperature). This parameter optimization achieves high regioregularity (isotactic triad >90%) and high molecular weight (Mn >100,000 g/mol) without requiring complex equipment or procedures.

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If conventional polymerization methods are used to synthesize polyisoindigo, then the polymer can be produced, but the molecular weight is low

Engineering Contradiction:
Improvemolecular weightVSAvoidpolymerization method complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent optimizes reaction parameters including catalyst selection (AlEt2Cl, AlEt2Br, or AlEt2I), solvent choice (toluene), temperature control (0°C to room temperature), and monomer-to-catalyst ratio to achieve high molecular weight (Mn >100,000 g/mol) through a relatively simple one-step polymerization process without complex equipment.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If polyisoindigo is used in organic electronic devices, then the devices can operate, but the lifetime is short due to photo-oxidation

Engineering Contradiction:
Improvedevice lifetimeVSAvoidphoto-oxidation
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent converts the harmful effect of photo-oxidation into a beneficial identification tool by utilizing the characteristic blue color that develops when polyisoindigo undergoes photo-oxidation. This color change serves as a visual indicator for quality control, allowing manufacturers to detect and control photo-oxidation effects, thereby improving device reliability and lifetime through better material quality assurance.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The patent exploits the color change of polyisoindigo from colorless to blue upon photo-oxidation as a quality control indicator. This color transformation allows for visual detection and monitoring of photo-oxidation程度, enabling manufacturers to control material quality and improve device lifetime by identifying and preventing excessive photo-oxidation damage.

Inventive Principle:
Principle #32Color changes

4Reliability

If polyisoindigo is used in organic electronic devices, then the devices can operate, but the efficiency is low due to insufficient charge carrier mobility

Engineering Contradiction:
Improvecharge carrier mobilityVSAvoiddevice efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent achieves high charge carrier mobility (μh > 10^-5 cm²/Vs) by optimizing polymerization parameters including catalyst selection (AlEt2Cl, AlEt2Br, or AlEt2I), solvent choice (toluene), temperature control (0°C to room temperature), and monomer-to-catalyst ratio. These parameter optimizations produce highly regioregular polymers with excellent molecular weight and packing, thereby improving device efficiency without requiring complex processing equipment.

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 conjugated polymer exhibits improved solubility, film-forming properties, and thermal stability, with enhanced energy conversion efficiency and broadened absorption range, making it suitable for organic solar cells, electroluminescent devices, and field-effect transistors.

Implementation Method 1

conductive polymers, in particular polyacetylene, polythiophene, polypyrrole and polyisoindigo and their derivatives

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

Conductive polymers, also referred to as intrinsically conducting polymers (ICPs), have received a great deal of attention in recent years due to their potential applications in organic electronic devices

Methodology Applied
Scientific EffectElectron delocalization:

Data Source

PatentEP2644629B1Conjugated polymer containing isoindigo units, preparation method and use thereof
Publication Date: 2018.11.07 OCEANS KING LIGHTING SCI&TECH CO LTD
  • EP2644629B1 patent drawingFigure 1~2
  • EP2644629B1 patent drawingFigure 3~5
  • EP2644629B1 patent drawing

AI summary

A conjugated polymer containing isoindigo units is disclosed, which has the following structure: P: formula I; wherein, Ar is formula II, formula III or formula IV; R1 is a C8-C20 alkyl; R2 is a C1-C12 alkyl; n is an integer of 2-50. The conjugated polymer containing isoindigo units of this type has good solubility and film-forming property, as well as high thermal stability. HOMO and LUMO energy level are regulated effectively; the absorption range is broaden; and the energy conversion efficiency is greatly improved. A preparation method for the above conjugated polymer containing isoindigo units and use thereof in related fields are also provided.