Organic Electronics for Electrochromic Materials and Devices

 
 
Wiley-VCH (Verlag)
  • erschienen am 20. April 2021
  • |
  • 528 Seiten
 
E-Book | ePUB mit Adobe-DRM | Systemvoraussetzungen
978-3-527-83062-6 (ISBN)
 
All types of organic electrochoromic materials and multi-functional devices are well presented.
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Prof. Hong Meng received his Ph.D. from University of California Los Angeles in 2002. He has been working in the field of organic electronics for more than 20 years. His career experiences including working in the Institute of Materials Science and Engineering at Singapore, Lucent Technologies Bell Labs, DuPont Experimental Station. In 2014, he moved to School of Advanced Materials Peking University Shenzhen Graduate School. He has contributed over 120 peer-reviewed papers (citation: 6000) in chemistry and materials science fields, filed over 46 US patents, 50 Chinese patents.
INTRODUCTION OF ORGANIC ELECTROCHROMISM
General Introduction
History of Electrochromism
The Key Parameters of Electrochromism
Conclusion

ADVANCES IN POLYMER ELECTROLYTES FOR ELECTROCHROMIC APPLICATION
Introduction
Requirements of Polymer Electrolytes in Electrochromic Applications
Types of Polymer Electrolytes
Conclusions

ELECTROCHROMIC SMALL MOLECULES
Background of Small Molecule Electrochromic
Technology Development of CP
Violene-cyanine Hybrids(AIE PL OEC)
Terephthalate Derivatives(Multi-color OEC)
Isophthalate Derivatives
Methyl Ketone Derivatives
Diphenylacetylenes
Fluoran Dye Derivatives
pH-Responsive Molecules Derivatives
TPA Dye Derivatives
Hydrocarbon Derivatives-NIR-OEC

VIOLOGEN EC
The Introduction of OEC and Viologen
Different Structures of Amethyst Electrochromic Materials
Viologen Electrochromic Device
Companies Operating in the Field of Viologen Electrochromism
Conclusions

PRUSSIAN BLUE AND METALLOHEXACYANATES
Background
Technology Development of PB
Crystal structure
Electrochromic Mechanism
Synthesis
Assembled Electrochromic Devices (ECDs)
Nanocompsites
PB analogues
Electrochromic & Multi-applications

CONJUGATED ELECTROCHROMIC POLYMERS
Introduction
Poly(thiophene)-Based Conjugated Electrochromic Polymers
Poly(pyrrole)-Based Conjugated Electrochromic Polymers
Polycarbazole-Based Conjugated Electrochromic Polymers

TPA-PI/PA BASED CONJUGATED/NON-CONJUGATED ELECTROCHROMIC POLYMERS
Introduction
Development of TA-based Electrochromic Polyimides and Polyamides
Conclusions

METALLO-SUPERMOLECULAR POLYMERS
Introduction
Single Metallic System
Hetero-Metallic System.
The Fabrication Method of Metallopolymer film
Conclusion

METAL ORGANIC FRAMEWORK (MOFS) / COVALENT ORGANIC FRAMEWORK (COFS) BASED EC
Introduction
Current Studies in EC MOFs
Current studies in EC COFs
Conclusion and Prospect

NANOSTRUCTURED ELECTROCHROMIC MATERIALS
Introduction
Current Studies of Nanostructure in Electrochromism
Conclusion and Prospect

METAL ORGANIC FRAMEWORK (MOF) BASED EC
Introduction
Current studies in EC MOFs
Conclusion and Prospect

ORGANIC ELECTROLUMINOCHROMIC MATERIALS
Introduction
Conventional Mechanisms of Electroluminochromism
Electroluminochromic Performance Parameters
Classical Materials
Future Perspectives and Conclusion

ORGANIC PHOTOELECTROCHROMIC DEVICES
Introduction
Structure Design of PECDs
Future Perspectives and Conclusion

APPLICATION OF OEC DEVICES
Smart Window
Dimmable Rearview Mirror
Sensors
The Application of Electrochromic Device in Display

COMMERCIALIZED OEC MATERIALS AND RELATED ANALYSIS OF COMPANY PATENTS
General Introduction
Gentex Corporation
Ricoh Company, Ltd
Canon Inc.
BOE Technology Group Co., Ltd. and OPPO Guangdong Mobile Communications Co., Ltd.
Other Important Enterprises
Conclusion

MAIN CHALLENGES FOR THE COMMERCIALIZATION OF OEC
The Long-term Stability of OEC Materials
The Mechanical Stability of OEC Devices (Encapsulation Technology)
Large-Area Process Technology: Spray Coating and Roll-to-Roll Processes
Conclusions and Perspective

1
Introduction


1.1 General Introduction


Electrochromism is the phenomenon that describes the optical (absorbance/transmittance/reflectance) change in material via a redox process induced by an external voltage or current [1]. Usually the electrochromic (EC) materials exhibit color change between a colored state and colorless state or between two colors, even multicolor. In nature, its origin is from the change of occupation number of material's internal electronic states. As the core of EC technology, the EC materials have built up many categories during decades of development, for example, according to the coloration type, it could be classified as anodically coloring materials (coloration upon oxidation) or cathodically coloring materials (coloration upon reduction) [2]. Based on the light absorption region in the solar radiation, which consists of these three parts: ultraviolet (UV), visible (Vis), and near-infrared radiation (NIR) lights (Figure 1.1), it could be divided into visible EC materials (wavelength: 380-780?nm), which can be seen by the human eye and therefore are suitable for smart window and indicator applications, and NIR EC materials (wavelength: 780-2500?nm), which have great potential for thermal regulation technologies and even in national defense-related applications [3]. And on the basis of materials species, there are mainly inorganic, organic, and hybrid EC materials [4, 5] (https://commons.wikimedia.org/wiki/File:Solar_spectrum_en.svg). Inorganic EC materials are transition metal oxides (TMOs) (WO3, NiO, TiO2, and Prussian Blue [PB]), organic EC materials including small molecules (e.g. viologen), conjugated polymers (e.g. poly(pyrrole), poly(thiophene), and poly(carbazole)) and aromatic polymers (e.g. polyimides [PIs] and polyamides [PAs]), organic-inorganic hybrid materials referring to metallo-supermolecular polymers, and metal-organic framework (MOF). Among them, inorganic materials exhibit excellent long-term stability compared with organic ones; however, considering the structure variety, flexibility, and low-cost solution processability, organic EC materials are superior to inorganic materials. The organic-inorganic hybrid materials are designed to combine advantages of both organic and inorganic materials.

Figure 1.1 Solar irradiance spectrum above atmosphere and at the surface of the Earth.

Source: Nick84: https://commons.wikimedia.org/wiki/File:Solar_spectrum_en.svg, Licensed under CC BY-SA 3.0.

EC materials exhibit color changes during the redox process; therefore the electrochromic devices (ECDs) generally consist of three elements: electrodes, EC materials, and electrolyte solution. The electrodes offer a constant supply of electric current, and ions are conducted by the electrolyte solution. Then the EC materials undergo electrochemical oxidation and/or reduction, which results in changes in the optical bandgap and colors. As shown in Figure 1.2, a typical ECD has five layers: two transparent conducting oxide (TCO) layers, EC layer, ion-conducting layer (electrolyte solution), ion storage layer. Particularly, the ion storage layer acts as the "counter electrode" to store ions and keep electric charge balance. And according to the exact state of EC materials, there are three types of ECD: film type (I), solution type (II), and hybrid type (III). The Type I ECD is the most common; many kinds of EC materials are suitable for this type including TMOs, conjugated/non-conjugated polymers, metallo-supermolecular polymers, and MOF/covalent organic framework (COF) materials, which using spin-coating, spray-coating, and dip-coating processes to form uniform films; these films won't dissolute in electrolyte solutions. Type II ECD requires that the EC materials have good solubility in electrolyte solutions. Therefore many organic small molecules such as viologen, terephthalate derivatives, and isophthalate derivatives are appropriate for this type of device. Meanwhile the fabrication method for this type of device is the most simple one. It just needs to dissolve the electrolyte and EC material in a specific solvent and inject into the prepared conducting cell. Type III ECD uses film-type EC materials as working electrode and solution-type EC materials as ion storage layer.

Figure 1.2 The scheme of three types of electrochromic devices.

1.2 The History of Electrochromic Materials


The word "electrochromism" was invented by John R. Platt in 1960 [6], in analogy to "thermochromism" and "photochromism." However, the EC phenomenon could be traced to the nineteenth century, as early as 1815. Berzelius observed the color change of pure tungsten trioxide (WO3) during the reduction when warmed under a flow of dry hydrogen gas. Then from 1913 to 1957, some patents described the earliest form of ECD based on WO3 [7, 8]. Therefore the origins of electrochromism are the nineteenth and twentieth centuries. After then, electrochromism technology began to undergo rapid development, especially the exploration of many classes of EC materials. As showed in the technology roadmap (Figure 1.3), we summarized several generations of EC materials during long-term development.

Figure 1.3 The roadmap of EC materials development.

The first-generation EC material is TMOs (e.g. WO3, NiO, and PB). Among them, WO3 plays an important role in the electrochromism field; as the first founded EC material, it has already realized commercialization in smart windows application. PB was discovered as a dye by Diesbach in 1704, and then the electrochemical behavior and EC performance of PB was firstly reported by Neff at 1978 [9]. Benefitted from the structure stability and reversible redox process of those inorganic TMOs, the electrochromism based on the thin-film TMOs are widely investigated, including the development of new TMOs materials, introduction of new nanostructures, and different element doping.

Following the first-generation TMO EC materials, organic small molecule EC materials have emerged since 1970. Among them, viologen as the most representative small molecule was first discovered by Michaelis and Hill in 1932 [10], and because of the violet on the reduction, these 1,1´-disubstituted-4,4´-bipyridine compounds were named "viologen." Then in 1973, Shoot made a new flat alphanumeric display using heptyl viologen; this can be regarded as the beginning of the use of viologen for electrochromism [11]. After a century's development, viologen already has been successfully commercialized. Besides the viologen, other small molecules EC materials such as terephthalate derivatives, isophthalate derivatives, methyl ketone derivatives, and some dye molecules have also attracted much attentions from scientists due to their simple structure and low cost.

The third-generation EC materials are conjugated polymers. In 1983, Francis Garnier and coworkers firstly characterized the EC properties of a series of five-membered heterocyclic polymers including poly(pyrrole), poly(thiophene), poly(3-methylthiophene), poly(3,4-dimethylthiophene), and poly(2,2´-dithiophene). Since then, conjugated polymers were given rise to the rapid emerge as a new class of electrochromism [12]. Five years later, Berthold Schreck observed the electrochromism phenomenon of poly(carbazole), which showed a color change from pale yellowish to green together with the conductivity enhancement [13]. To date, the conjugated polymer EC system has been well developed, from better understandings on mechanisms to completed color pallette with soluble or electro-deposited polymers, and even full-color display samples or roll-to-roll fabricated flexible devices.

Later, in early 2000, triarylamine (TA)-based aromatic polymers especially the PIs and PAs have drawn considerable attention from the research community as the fourth-generation EC materials. The correlation between electrochemical properties and chemical structures of different aromatic PIs was firstly described in 1990. Ten years later, Zhiyuan Wang and coworkers [14] reported the first EC behavior of poly(ether naphthalimide)s, which showed stepwise coloration process, from colorless to red and to dark blue corresponding to the neutral, radical anion, and dianion species, respectively. However, due to the high rigidity of the PIs/PAs backbone and strong intermolecular interactions, the poor processability limited the development of PIs or PAs EC materials. Therefore the TA groups were introduced to the PIs/PAs backbone to improve the solubility of aromatic polymers. The first TA-based polyamide PA was synthesized in 1990 [15], and the first aromatic polyimides integrating interesting EC properties containing TA groups were disclosed in 2005 [16]. Since then, Liou, Hsiao and, other groups have developed numerous TA-based EC PIs/PAs. Most of the PIs/PAs were solution processible...

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