Conjugated Polymers for Organic Electronics


Book Description

Covers the chemistry and physics of conjugated polymers, and how they can be designed and optimised for various electronic applications.







Design and Synthesis of Conjugated Polymers and Small Molecules Based on Thiophene-substituted Isoindigo, 5-acetyl-4H-cyclopenta[c]thiophene-4,6(5H)-dione, and Diketopyrrolopyrrole Electron-deficient Units


Book Description

Pi-Conjugated polymers and small molecules are useful for their semiconductor properties in organic electronic devices such as organic photovoltaics, light emitting diodes, and thin film transistors. They also find application in chemical detection for their high sensitivity to fluorescence quenching species. Described herein are the syntheses of two new electron deficient monomer units for polymers and small molecules. 5-acetyl-1,3-dibromo-4H- cyclopenta[c]thiophene-4,6(5H)-dione was synthesized for the first time. It can be conveniently polymerized by Stille coupling to form polymers initially insoluble in common solvents, which can be rendered soluble by deprotonation with various organic amines. Solutions in methanol are highly fluorescent and show strong quenching when exposed to Ni2+ and Cu2+. Additionally, films can be cast from chloroform or dichlorobenzene solutions with triethylamine. New polymers and small molecules based on the recently reported thiophene substituted isoindigo were also synthesized and employed in photovoltaic devices reaching a maximum of 3.75 % power conversion efficiency, the highest yet reported for this unit. Also discussed is a series of low band gap small molecule semiconductors incorporating two diketopyrrolopyrrole units and their photovoltaic applications. The best power conversion efficiency for a molecule in this series was 2.22 %.




Synthesis and Characterization of Novel Conjugated Polymers and Small Molecules for Photovoltaic Applications


Book Description

This dissertation describes the synthesis and characterization of several novel conjugated polymers and small molecules for use in research on organic photovoltaics (i.e. polymer solar cells/organic solar cells). Chapter 1 is an introductory chapter that briefly introduces semiconducting polymers and gives a brief overview of their use in polymer solar cells. Chapter 2 describes the synthesis and characterization of the conjugated polyelectrolyte, poly{(4,4-bis(3'-(N-ethyl-N,N-dimethylammonio)propyl)cyclopenta[2,1-b:3,4-b']dithiophene)-2,6-diyl-alt-(thiophene-2,5-diyl)} bromide (PCT). Chapter 3 describes the synthesis and characterization of a series of conjugated polymers containing substituted dithieno[3,2-a:2',3'-c]phenazine monomer units, and also describes the fabrication and analysis of solar cells devices made from these materials. Chapter 4 describes the synthesis and characterization of a series of conjugated polymers and small molecules based on the condensation of various aromatic o-diamines with o-diketones to produce novel N-heteroacenes. Chapter 5 gives a brief review of the work reported in this dissertation and provides suggestions for future work that can be built on those findings.




Synthesis of Conjugated Polymers and Block Copolymers Via Catalyst Transfer Polycondensation


Book Description

Conjugated polymers hold tremendous potential as low-cost, solution processable materials for electronic applications such organic light-emitting diodes and photovoltaics. While the concerted efforts of many research groups have improved the performance of organic electronic devices to near-relevant levels for commercial exploitation over the last decade, the overall performance of organic light-emitting diode and organic photovoltaic devices still lags behind that of their traditional, inorganic counterparts. Realizing the full potential of organic electronics will require a comprehensive, molecular-level understanding of conjugated polymer photophysics. Studying pure, well-defined, and reproducible conjugated polymer materials should enable these efforts; unfortunately, conjugated polymers are typically synthesized by metal-catalyzed step-growth polycondensation reactions that do not allow for rigorous control over polymer molecular weight or molecular weight distribution (i.e., dispersity). Chain-growth syntheses of conjugated polymers would not only allow for precise control over the aforementioned polymer metrics such as molecular weight and dispersity, but could also potentially create new applications by enabling the preparation of more advanced macromolecular structures such as block copolymers and surface grafted polymers. Our efforts toward realizing these goals as well as toward exploiting chain-growth methodologies to better understand fundamental conjugated polymer photophysics and self-assembly will be presented.




Three Dimensional Molecular Architectures for the Synthesis and Improved Properties of High Performance Polymers


Book Description

Conjugated polymers have found various uses in optoelectronic applications, including chemical sensors, light-emitting diodes, and photovoltaic materials. In this thesis, we investigate the effect of having a molecular architecture that is both rigid and three-dimensional might play in the synthesis and performance of conjugated polymers. We discuss the efficient synthesis of a hydrophilic monomer bearing a threedimensional noncompliant array of hydroxyl groups that prevents water-driven excimer features of hydrophobic poly(p-phenylene ethynylene) backbones. We also use the detection of 3-nitrotyrosine as a probe to learn more about its physical state in solution. We further utilize the monomer above in a biocompatible post-polymerization functionalization reaction, taking advantage of the polymer's structural motif for the controllable attachment of biotin. The utility of this method is demonstrated for a model biosensor that responds to streptavidin. Finally, we discuss how rigid molecular architectures can be harnessed to bring two reacting groups together for the annulation of various [pi]-systems. The optical effects of the transformation are both notable and predictable, and the molecules have potential as monomers for conjugated polymer application in high performance organic light emitting diodes and photovoltaic devices.




Organic Light Emitting Devices


Book Description

This high-class book reflects a decade of intense research, culminating in excellent successes over the last few years. The contributions from both academia as well as the industry leaders combine the fundamentals and latest research results with application know-how and examples of functioning displays. As a result, all the four important aspects of OLEDs are covered: - syntheses of the organic materials - physical theory of electroluminescence and device efficiency - device conception and construction - characterization of both materials and devices. The whole is naturally rounded off with a look at what the future holds in store. The editor, Klaus Muellen, is director of the highly prestigious MPI for polymer research in Mainz, Germany, while the authors include Nobel Laureate Alan Heeger, one of the most notable founders of the field, Richard Friend, as well as Ching Tang, Eastman Kodak's number-one OLED researcher, known throughout the entire community for his key publications.




Conjugated Polymers


Book Description

This book covers properties, processing, and applications of conducting polymers. It discusses properties and characterization, including photophysics and transport. It then moves to processing and morphology of conducting polymers, covering such topics as printing, thermal processing, morphology evolution, conducting polymer composites, thin films




Conjugated Polymers and Small Molecules with Latent Hydrogen-bonding for Organic Electronic Applications


Book Description

Conjugated polymers and small molecules are gaining a growing attention as the active materials for flexible and printed electronics. The present work discusses the exploration of novel conjugated polymers and small molecules with latent hydrogen-bonding on the conjugated backbone for electronic applications. In the first study, we synthesized a class of conjugated polymers with latent hydrogen-bonding utilizing Suzuki coupling reactions. The resulting polymers can be converted into actual hydrogen-bonded polymers upon thermal or UV removal of the t-butoxyl carbonyl (t-Boc) protection groups on the main chains. Large bathochromic absorption shift and dramatically decreased material solubility of the polymer were shown after the formation of hydrogen-bonding, indicating their enhanced interchain interactions. Photolithographic patterned electrochromic devices was fabricated and tested with the latent hydrogen-bonded conjugated polymers. The second study extends in assessing the field-effect transistor performance of two diketopyrrolopyrrole-based conjugated small molecules with latent hydrogen-bonding. Effects of the activation of latent hydrogen-bonding networks on the small molecule film properties, including UV/Vis absorption, band gap, solvent resistance, film morphology, molecular packing mode, and charge mobility are investigated. Highly crystalline films and improved field-effect mobility of the device was observed for both small molecules after the hydrogen-bonding activation, suggesting an efficient control of molecular organization and device performance of the latent hydrogen-bonding strategy. Based on similar principles, a series of conjugated statistical copolymers with varied latent hydrogen-bonding content on the main chain were studied in the third part of this work. Increased hole mobility was observed for the organic field-effect transistor devices of polymers in which higher percentage of hydrogen-bonded repeating units were comprised, which suggested the potential of latent hydrogen-bonding strategy in constructing solution-processed conjugated polymers with improved semiconducting performance.