Naphthyridine Conjugated Polymers for OPV Charge Mobility

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Solution Overview

Problem

Current organic semiconducting polymers for organic electronic devices face challenges in achieving high charge carrier mobility, low bandgap, and stability, particularly for use in organic photovoltaic cells, where they need to be easily synthesized, have good solubility, and be suitable for mass production.

Innovation Solution

Development of compounds containing 2,6-disubstituted-[1,5]naphthyridine or 1,6-disubstituted-1H-[1,5]naphthyridine-2-one units, which enhance solubility and morphology, leading to improved electrical properties and device performance by incorporating these units into conjugated polymers as electron acceptors.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional conjugated polymers are used for OPV devices, then device manufacturing by solution-processing is enabled, but charge carrier mobility and power conversion efficiency remain insufficient

Engineering Contradiction:
Improvesolution-processing capabilityVSAvoidcharge carrier mobility
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent modifies the chemical structure of conjugated polymers by incorporating 2,6-disubstituted-[1,5]naphthyridine units with specific substituents (R1, R2, R3 groups) to optimize electronic properties. This structural parameter change enhances charge carrier mobility while preserving solution-processability, resolving the contradiction between ease of manufacture and device performance

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite polymer structures combining electron-rich donor units with the electron-deficient 2,6-disubstituted-[1,5]naphthyridine acceptor units. This composite approach at the molecular level achieves both high charge carrier mobility and good solubility, enabling solution-processing while improving power conversion efficiency

Inventive Principle:
Principle #40Composite materials

2Reliability

If polymers with high charge carrier mobility are developed, then device performance improves, but synthesis complexity and difficulty increase

Engineering Contradiction:
Improvecharge carrier mobilityVSAvoidsynthesis complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent divides the polymer structure into distinct functional segments: the 2,6-disubstituted-[1,5]naphthyridine core unit with specific substituents that can be independently optimized. This segmentation allows systematic modification of electronic properties through substituent selection while maintaining a standardized core structure, simplifying the synthesis approach

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention employs parameter changes in the substituent groups (R1, R2, R3) of the naphthyridine unit to tune charge carrier mobility. By varying these parameters systematically, high mobility is achieved through straightforward chemical modification rather than complex synthesis routes

Inventive Principle:
Principle #35Parameter changes

3Use of energy by moving object

If polymers with low bandgap are designed to absorb maximum solar spectrum, then light harvesting efficiency improves, but oxidative stability decreases

Engineering Contradiction:
Improvelight harvesting efficiencyVSAvoidoxidative stability
Core Design Contradiction:
Use of energy by moving objectVSStability of the object's composition

Solution Approach 1:

The patent designs composite alternating copolymers with electron-rich donor units and electron-deficient 2,6-disubstituted-[1,5]naphthyridine acceptor units. This composite structure creates a low bandgap for enhanced light harvesting while the specific substitution pattern on the naphthyridine unit provides oxidative stability, resolving the contradiction between energy efficiency and compositional stability

Inventive Principle:
Principle #40Composite materials

4Productivity

If conjugated polymers are optimized for high efficiency OPV, then power conversion efficiency increases, but solubility and processability may be compromised

Engineering Contradiction:
Improvepower conversion efficiencyVSAvoidsolubility
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent modifies structural parameters of the polymer by introducing specific substituent groups (R1, R2, R3) on the naphthyridine unit. These parameter changes simultaneously optimize electronic properties for high power conversion efficiency and enhance solubility through appropriate substituent selection, eliminating the need to compromise between efficiency and processability

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 resulting polymers exhibit high charge carrier mobility, oxidative stability, and efficient light harvesting, enabling higher power conversion efficiency in organic photovoltaic devices and other organic electronic devices.

Implementation Method 1

conjugated polymers have found use in OPVs as they allow devices to be manufactured by solution-processing techniques... The conjugated polymer serves as the main absorber of the solar energy in the bulk-heterojunction blend layer

Methodology Applied
Scientific EffectPhotovoltaic effect: Photovoltaic Effect

Data Source

PatentUS11603431B2Organic semiconductors
Publication Date: 2023.03.14 RAYNERGY TEK INC
  • US11603431B2 patent drawing
  • US11603431B2 patent drawing
  • US11603431B2 patent drawing

AI summary

The invention relates to novel compounds containing one or more units derived from 2,6-disubstituted-[1,5]naphthyridine or 1,6-disubstituted-1H-[1,5]naphthyridine-2-one, to methods for their preparation and educts or intermediates used therein, to mixtures and formulations containing them, to the use of the compounds, mixtures and formulations as organic semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices and organic photodetectors (OPD), and to OE, OPV and OPD devices comprising these compounds, mixtures or formulations.