Fluorinated BODIPY Compounds for Near-Infrared Absorption
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Solution Overview
Problem
Conventional near-infrared (NIR) absorbers for organic optoelectronic elements face challenges such as insufficient processability, thermal stability, absorption intensity, and photo stability, particularly when evaporated under reduced pressure, leading to suboptimal performance in thin films and multi-junction devices.
Innovation Solution
Development of new organic photoactive compounds of specific chemical formulas (Ia) and (Ib) that exhibit improved absorption in the near-infrared range, thermal stability up to 300°C, and efficient energy transfer, allowing for the formation of J-aggregates in thin films, which enhance absorption and transport properties.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If conventional NIR absorbers are evaporated under reduced pressure, then deposition is achieved, but thermal stability deteriorates leading to decomposition
Solution Approach 1:
The patent modifies molecular parameters by introducing fluorinated alkyl groups and specific heteroaryl substituents at defined positions (R1-R10) of the BODIPY core structure. These parameter changes enhance thermal stability (allowing evaporation at 100-300°C) while maintaining processability through controlled molecular weight and structural rigidity.
Solution Approach 2:
The patent creates composite molecular structures combining the BODIPY chromophore core with fluorinated alkyl chains and heteroaryl groups. This composite approach integrates the light-absorbing functionality of BODIPY with the thermal stability of fluorinated groups and the structural diversity of heteroaryl moieties, achieving both deposition ease and thermal reliability.
2Illumination intensity
If conventional NIR absorbers are used in thin films, then absorption is achieved, but absorption intensity deteriorates
Solution Approach 1:
The patent applies local quality by introducing specific substituents at defined positions (R1-R10) of the BODIPY molecule. The fluorinated alkyl groups at positions R1-R3 enhance molecular packing in thin films, while heteroaryl groups at R4-R5 improve intermolecular interactions, collectively enhancing absorption intensity specifically in the thin film state without compromising overall film quality.
Solution Approach 2:
The patent utilizes color changes by extending the conjugation of the BODIPY core through heteroaryl groups and fluorinated alkyl chains, resulting in a bathochromic shift that enhances near-infrared absorption intensity. The molecular structure is designed to maximize molar extinction coefficient in the NIR region while maintaining appropriate film morphology.
3Illumination intensity
If conventional NIR absorbers are used, then absorption is achieved, but photo stability deteriorates
Solution Approach 1:
The patent creates an inert molecular environment by introducing fluorinated alkyl groups (CF3, CF2H, CHF2) at positions R1-R3 of the BODIPY core. These fluorinated groups provide steric protection and electronic stabilization, creating a chemically inert environment around the photosensitive BODIPY chromophore that resists photo-oxidation and degradation, thereby enhancing photo stability while maintaining NIR absorption capability.
4Productivity
If multi-junction devices are constructed, then efficiency is improved, but device complexity increases
Solution Approach 1:
The patent achieves universality by designing a single BODIPY molecular platform (with variable R1-R10 substituents) that can function across multiple absorption bands and device architectures. The core structure can be systematically modified to target different wavelength ranges, enabling the same molecular framework to serve in single-junction, tandem, or multi-junction devices, thereby reducing overall system complexity while maintaining high efficiency.
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 new compounds demonstrate broad near-infrared absorption, high open-circuit voltage values, and reduced parasitic absorption, enabling higher transparency and efficiency in organic solar cells and optoelectronic devices, suitable for single or multi-junction applications.
Implementation Method 1
a photoactive layer, preferably as a light-absorbing layer... which layer actively contributes as an absorber layer by absorption of light into electrical energy
Implementation Method 2
In organic photovoltaic elements free charge carriers are not directly created by light in organic photoactive compounds, but rather excitons are initially formed. In a second stage excitons are separated into free charge carriers which then contribute to the electrical current flow
Implementation Method 3
thermal stability up to 300°C
Data Source
AI summary
Compounds of formula (Ia) and/or formula (Ib),are disclosed wherein R1 and R3 are independently selected from the group consisting of H, halogen, alkyl, fluorinated or partly fluorinated alkyl, and heteroaryl, R2 is selected from the group consisting of halogen, fluorinated and partly fluorinated alkyl, R4 and R5 are independently selected from the group consisting of halogen, alkyl, fluorinated or partly fluorinated alkyl, alkenyl, alkinyl, alkoxy, aryl, and heteroaryl, Z is independently selected from the group consisting of CH2, CHR6 or CR7R8, with R6, R7 and R8 independently selected from the group consisting of H, halogen, alkyl, alkoxy, aryl, and heteroaryl, wherein n is independently 1, 2 or 3, U, V and W of formula (Ia) independently form an aryl ring or a heteroaryl ring, and T, U, V and W of formula (Ib) form an aryl ring or a heteroaryl ring.