Organic electronics

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Organic CMOS logic circuit. Total thickness is less than 3 mm. Scale bar: 25 mm Organic CMOS logic circuit.jpg
Organic CMOS logic circuit. Total thickness is less than 3 μm. Scale bar: 25 mm

Organic electronics is a field of materials science concerning the design, synthesis, characterization, and application of organic molecules or polymers that show desirable electronic properties such as conductivity. Unlike conventional inorganic conductors and semiconductors, organic electronic materials are constructed from organic (carbon-based) molecules or polymers using synthetic strategies developed in the context of organic chemistry and polymer chemistry.

Contents

One of the promised benefits of organic electronics is their potential low cost compared to traditional electronics. [1] [2] [3] Attractive properties of polymeric conductors include their electrical conductivity (which can be varied by the concentrations of dopants) and comparatively high mechanical flexibility. Challenges to the implementation of organic electronic materials are their inferior thermal stability, high cost, and diverse fabrication issues.

History

Electrically conductive polymers

Traditional conductive materials are inorganic, especially metals such as copper and aluminum as well as many alloys.[ citation needed ]

In 1862 Henry Letheby described polyaniline, which was subsequently shown to be electrically conductive. Work on other polymeric organic materials began in earnest in the 1960s. For example in 1963, a derivative of tetraiodopyrrole was shown to exhibit conductivity of 1 S/cm (S = Siemens). [4] In 1977, it was discovered that oxidation enhanced the conductivity of polyacetylene. The 2000 Nobel Prize in Chemistry was awarded to Alan J. Heeger, Alan G. MacDiarmid, and Hideki Shirakawa jointly for their work on polyacetylene and related conductive polymers. [5] Many families of electrically conducting polymers have been identified including polythiophene, polyphenylene sulfide, and others.

J.E. Lilienfeld [6] first proposed the field-effect transistor in 1930, but the first OFET was not reported until 1987, when Koezuka et al. constructed one using Polythiophene [7] which shows extremely high conductivity. Other conductive polymers have been shown to act as semiconductors, and newly synthesized and characterized compounds are reported weekly in prominent research journals. Many review articles exist documenting the development of these materials. [8] [9] [10] [11] [12]

In 1987, the first organic diode was produced at Eastman Kodak by Ching W. Tang and Steven Van Slyke. [13]

Electrically conductive charge transfer salts

In the 1950s, organic molecules were shown to exhibit electrical conductivity. Specifically, the organic compound pyrene was shown to form semiconducting charge-transfer complex salts with halogens. [14] In 1972, researchers found metallic conductivity (conductivity comparable to a metal) in the charge-transfer complex TTF-TCNQ.

Light and electrical conductivity

André Bernanose [15] [16] was the first person to observe electroluminescence in organic materials. Ching W. Tang and Steven Van Slyke, [17] reported fabrication of the first practical OLED device in 1987. The OLED device incorporated a double-layer structure motif composed of copper phthalocyanine and a derivative of perylenetetracarboxylic dianhydride. [18]

In 1990, a polymer light emitting diodes was demonstrated by Bradley, Burroughes, Friend. Moving from molecular to macromolecular materials solved the problems previously encountered with the long-term stability of the organic films and enabled high-quality films to be easily made. [19] In the late 1990's, highly efficient electroluminescent dopants were shown to dramatically increase the light-emitting efficiency of OLEDs [20] These results suggested that electroluminescent materials could displace traditional hot-filament lighting. Subsequent research developed multilayer polymers and the new field of plastic electronics and organic light-emitting diodes (OLED) research and device production grew rapidly. [21]

Conductive organic materials

Edge-on view of portion of crystal structure of hexamethylene TTF-TCNQ charge transfer salt, highlighting the segregated stacking. Such molecular semiconductors exhibit anisotropic electrical conductivity. SegStackEdgeOnHMTFCQ.jpg
Edge-on view of portion of crystal structure of hexamethylene TTF-TCNQ charge transfer salt, highlighting the segregated stacking. Such molecular semiconductors exhibit anisotropic electrical conductivity.

Organic conductive materials can be grouped into two main classes: polymers and conductive molecular solids and salts. Polycyclic aromatic compounds such as pentacene and rubrene often form semiconducting materials when partially oxidized.

Conductive polymers are often typically intrinsically conductive or at least semiconductors. They sometimes show mechanical properties comparable to those of conventional organic polymers. Both organic synthesis and advanced dispersion techniques can be used to tune the electrical properties of conductive polymers, unlike typical inorganic conductors. Well-studied class of conductive polymers include polyacetylene, polypyrrole, polythiophenes, and polyaniline. Poly(p-phenylene vinylene) and its derivatives are electroluminescent semiconducting polymers. Poly(3-alkythiophenes) have been incorporated into prototypes of solar cells and transistors.

Organic light-emitting diode

An OLED (organic light-emitting diode) consists of a thin film of organic material that emits light under stimulation by an electric current. A typical OLED consists of an anode, a cathode, OLED organic material and a conductive layer. [23]

Br6A, a next generation pure organic light emitting crystal family Br6Acrystal.png
Br6A, a next generation pure organic light emitting crystal family
Schematic of a bilayer OLED: 1. Cathode (-), 2. Emissive layer, 3. Emission of radiation, 4. Conductive layer, 5. Anode (+) Bilayer-OLED.png
Schematic of a bilayer OLED: 1. Cathode (−), 2. Emissive layer, 3. Emission of radiation, 4. Conductive layer, 5. Anode (+)

OLED organic materials can be divided into two major families: small-molecule-based and polymer-based. Small molecule OLEDs (SM-OLEDs) include tris(8-hydroxyquinolinato)aluminium [17] fluorescent and phosphorescent dyes, and conjugated dendrimers. Fluorescent dyes can be selected according to the desired range of emission wavelengths; compounds like perylene and rubrene are often used. Devices based on small molecules are usually fabricated by thermal evaporation under vacuum. While this method enables the formation of well-controlled homogeneous film; is hampered by high cost and limited scalability. [24] [25] Polymer light-emitting diodes (PLEDs) are generally more efficient than SM-OLEDs. Common polymers used in PLEDs include derivatives of poly(p-phenylene vinylene) [26] and polyfluorene. The emitted color is determined by the structure of the polymer. Compared to thermal evaporation, solution-based methods are more suited to creating films with large dimensions.

Organic field-effect transistor

Rubrene-OFET with the highest charge mobility Rubrene.svg
Rubrene-OFET with the highest charge mobility

An organic field-effect transistor (OFET) is a field-effect transistor utilizing organic molecules or polymers as the active semiconducting layer. A field-effect transistor (FET) is any semiconductor material that utilizes electric field to control the shape of a channel of one type of charge carrier, thereby changing its conductivity. Two major classes of FET are n-type and p-type semiconductor, classified according to the charge type carried. In the case of organic FETs (OFETs), p-type OFET compounds are generally more stable than n-type due to the susceptibility of the latter to oxidative damage.

As for OLEDs, some OFETs are molecular and some are polymer-based system. Rubrene-based OFETs show high carrier mobility of 20–40 cm2/(V·s). Another popular OFET material is Pentacene. Due to its low solubility in most organic solvents, it's difficult to fabricate thin film transistors (TFTs) from pentacene itself using conventional spin-cast or, dip coating methods, but this obstacle can be overcome by using the derivative TIPS-pentacene.

Organic electronic devices

Organics-based flexible display Flexible display.jpg
Organics-based flexible display
Five structures of organic photovoltaic materials Organic photovoltaic material.pdf
Five structures of organic photovoltaic materials

Organic solar cells could cut the cost of solar power compared with conventional solar-cell manufacturing. [27] Silicon thin-film solar cells on flexible substrates allow a significant cost reduction of large-area photovoltaics for several reasons: [28]

  1. The so-called 'roll-to-roll'-deposition on flexible sheets is much easier to realize in terms of technological effort than deposition on fragile and heavy glass sheets.
  2. Transport and installation of lightweight flexible solar cells also saves cost as compared to cells on glass.

Inexpensive polymeric substrates like polyethylene terephthalate (PET) or polycarbonate (PC) have the potential for further cost reduction in photovoltaics. Protomorphous solar cells prove to be a promising concept for efficient and low-cost photovoltaics on cheap and flexible substrates for large-area production as well as small and mobile applications. [28]

One advantage of printed electronics is that different electrical and electronic components can be printed on top of each other, saving space and increasing reliability and sometimes they are all transparent. One ink must not damage another, and low temperature annealing is vital if low-cost flexible materials such as paper and plastic film are to be used. There is much sophisticated engineering and chemistry involved here, with iTi, Pixdro, Asahi Kasei, Merck & Co.|Merck, BASF, HC Starck, Sunew, Hitachi Chemical, and Frontier Carbon Corporation among the leaders. [29] Electronic devices based on organic compounds are now widely used, with many new products under development. Sony reported the first full-color, video-rate, flexible, plastic display made purely of organic materials; [30] [31] television screen based on OLED materials; biodegradable electronics based on organic compound and low-cost organic solar cell are also available.

Fabrication methods

Small molecule semiconductors are often insoluble, necessitating deposition via vacuum sublimation. Devices based on conductive polymers can be prepared by solution processing methods. Both solution processing and vacuum based methods produce amorphous and polycrystalline films with variable degree of disorder. "Wet" coating techniques require polymers to be dissolved in a volatile solvent, filtered and deposited onto a substrate. Common examples of solvent-based coating techniques include drop casting, spin-coating, doctor-blading, inkjet printing and screen printing. Spin-coating is a widely used technique for small area thin film production. It may result in a high degree of material loss. The doctor-blade technique results in a minimal material loss and was primarily developed for large area thin film production. Vacuum based thermal deposition of small molecules requires evaporation of molecules from a hot source. The molecules are then transported through vacuum onto a substrate. The process of condensing these molecules on the substrate surface results in thin film formation. Wet coating techniques can in some cases be applied to small molecules depending on their solubility.

Organic solar cells

Bilayer organic photovoltaic cell BilayerElectrode.pdf
Bilayer organic photovoltaic cell

Organic semiconductor diodes convert light into electricity. Figure to the right shows five commonly used organic photovoltaic materials. Electrons in these organic molecules can be delocalized in a delocalized π orbital with a corresponding π* antibonding orbital. The difference in energy between the π orbital, or highest occupied molecular orbital (HOMO), and π* orbital, or lowest unoccupied molecular orbital (LUMO) is called the band gap of organic photovoltaic materials. Typically, the band gap lies in the range of 1-4eV. [32] [33] [34]

The difference in the band gap of organic photovoltaic materials leads to different chemical structures and forms of organic solar cells. Different forms of solar cells includes single-layer organic photovoltaic cells, bilayer organic photovoltaic cells and heterojunction photovoltaic cells. However, all three of these types of solar cells share the approach of sandwiching the organic electronic layer between two metallic conductors, typically indium tin oxide. [35]

Illustration of thin film transistor device Tft.png
Illustration of thin film transistor device

Organic field-effect transistors

An organic field-effect transistor is a three terminal device (source, drain and gate). The charge carriers move between source and drain, and the gate serves to control the path's conductivity. There are mainly two types of organic field-effect transistor, based on the semiconducting layer's charge transport, namely p-type (such as dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene, DNTT), [36] and n-type (such phenyl C61 butyric acid methyl ester, PCBM). [37] Certain organic semiconductors can also present both p-type and n-type (i.e., ambipolar) characteristics. [38]

Such technology allows for the fabrication of large-area, flexible, low-cost electronics. [39] One of the main advantages is that being mainly a low temperature process compared to CMOS, different type of materials can be utilized. This makes them in turn great candidates for sensing. [40]

Features

Conductive polymers are lighter, more flexible, and less expensive than inorganic conductors. This makes them a desirable alternative in many applications. It also creates the possibility of new applications that would be impossible using copper or silicon.

Organic electronics not only includes organic semiconductors, but also organic dielectrics, conductors and light emitters.

New applications include smart windows and electronic paper. Conductive polymers are expected to play an important role in the emerging science of molecular computers.

See also

Related Research Articles

<span class="mw-page-title-main">OLED</span> Diode that emits light from an organic compound

An organic light-emitting diode (OLED), also known as organic electroluminescentdiode, is a type of light-emitting diode (LED) in which the emissive electroluminescent layer is an organic compound film that emits light in response to an electric current. This organic layer is situated between two electrodes; typically, at least one of these electrodes is transparent. OLEDs are used to create digital displays in devices such as television screens, computer monitors, and portable systems such as smartphones and handheld game consoles. A major area of research is the development of white OLED devices for use in solid-state lighting applications.

<span class="mw-page-title-main">Flexible electronics</span> Mounting of electronic devices on flexible plastic substrates

Flexible electronics, also known as flex circuits, is a technology for assembling electronic circuits by mounting electronic devices on flexible plastic substrates, such as polyimide, PEEK or transparent conductive polyester film. Additionally, flex circuits can be screen printed silver circuits on polyester. Flexible electronic assemblies may be manufactured using identical components used for rigid printed circuit boards, allowing the board to conform to a desired shape, or to flex during its use.

<span class="mw-page-title-main">Indium tin oxide</span> Chemical compound

Indium tin oxide (ITO) is a ternary composition of indium, tin and oxygen in varying proportions. Depending on the oxygen content, it can be described as either a ceramic or an alloy. Indium tin oxide is typically encountered as an oxygen-saturated composition with a formulation of 74% In, 8% Sn, and 18% O by weight. Oxygen-saturated compositions are so typical that unsaturated compositions are termed oxygen-deficient ITO. It is transparent and colorless in thin layers, while in bulk form it is yellowish to gray. In the infrared region of the spectrum it acts as a metal-like mirror.

<span class="mw-page-title-main">Conductive polymer</span> Organic polymers that conduct electricity

Conductive polymers or, more precisely, intrinsically conducting polymers (ICPs) are organic polymers that conduct electricity. Such compounds may have metallic conductivity or can be semiconductors. The main advantage of conductive polymers is that they are easy to process, mainly by dispersion. Conductive polymers are generally not thermoplastics, i.e., they are not thermoformable. But, like insulating polymers, they are organic materials. They can offer high electrical conductivity but do not show similar mechanical properties to other commercially available polymers. The electrical properties can be fine-tuned using the methods of organic synthesis and by advanced dispersion techniques.

Poly(<i>p</i>-phenylene vinylene) Chemical compound

Poly(p-phenylene vinylene) (PPV, or polyphenylene vinylene) is a conducting polymer of the rigid-rod polymer family. PPV is the only polymer of this type that can be processed into a highly ordered crystalline thin film. PPV and its derivatives are electrically conducting upon doping. Although insoluble in water, its precursors can be manipulated in aqueous solution. The small optical band gap and its bright yellow fluorescence makes PPV a candidate in applications such as light-emitting diodes (LED) and photovoltaic devices. Moreover, PPV can be doped to form electrically conductive materials. Its physical and electronic properties can be altered by the inclusion of functional side groups.

Organic semiconductors are solids whose building blocks are pi-bonded molecules or polymers made up by carbon and hydrogen atoms and – at times – heteroatoms such as nitrogen, sulfur and oxygen. They exist in the form of molecular crystals or amorphous thin films. In general, they are electrical insulators, but become semiconducting when charges are injected from appropriate electrodes or are introduced by doping or photoexcitation.

<span class="mw-page-title-main">Flexible organic light-emitting diode</span> Type of computer monitor

A flexible organic light-emitting diode (FOLED) is a type of organic light-emitting diode (OLED) incorporating a flexible plastic substrate on which the electroluminescent organic semiconductor is deposited. This enables the device to be bent or rolled while still operating. Currently the focus of research in industrial and academic groups, flexible OLEDs form one method of fabricating a rollable display.

<span class="mw-page-title-main">Organic field-effect transistor</span> Type of field-effect transistor

An organic field-effect transistor (OFET) is a field-effect transistor using an organic semiconductor in its channel. OFETs can be prepared either by vacuum evaporation of small molecules, by solution-casting of polymers or small molecules, or by mechanical transfer of a peeled single-crystalline organic layer onto a substrate. These devices have been developed to realize low-cost, large-area electronic products and biodegradable electronics. OFETs have been fabricated with various device geometries. The most commonly used device geometry is bottom gate with top drain and source electrodes, because this geometry is similar to the thin-film silicon transistor (TFT) using thermally grown SiO2 as gate dielectric. Organic polymers, such as poly(methyl-methacrylate) (PMMA), can also be used as dielectric. One of the benefits of OFETs, especially compared with inorganic TFTs, is their unprecedented physical flexibility, which leads to biocompatible applications, for instance in the future health care industry of personalized biomedicines and bioelectronics.

<span class="mw-page-title-main">PEDOT:PSS</span> Polymer

Poly(3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT:PSS) is a composite material where PEDOT provides electrical conductivity, and PSS acts as a counter-ion to balance the charge and improve the water solubility and processability of PEDOT. Polystyrene sulfonate is a sulfonated polystyrene. Part of the sulfonyl groups are deprotonated and carry a negative charge. The other component poly(3,4-ethylenedioxythiophene) (PEDOT) is a conjugated polymer and carries positive charges and is based on polythiophene. Together the charged macromolecules form a macromolecular salt.

<span class="mw-page-title-main">Pentacene</span> Hydrocarbon compound (C22H14) made of 5 fused benzene rings

Pentacene is a polycyclic aromatic hydrocarbon consisting of five linearly-fused benzene rings. This highly conjugated compound is an organic semiconductor. The compound generates excitons upon absorption of ultra-violet (UV) or visible light; this makes it very sensitive to oxidation. For this reason, this compound, which is a purple powder, slowly degrades upon exposure to air and light.

<span class="mw-page-title-main">Rubrene</span> Chemical compound

Rubrene (5,6,11,12-tetraphenyltetracene) is the organic compound with the formula (C18H84. It is a red colored polycyclic aromatic hydrocarbon. Because of its distinctive optical and electrical properties, rubrene has been extensively studied. It has been used as a sensitiser in chemoluminescence and as a yellow light source in lightsticks.

Hybrid solar cells combine advantages of both organic and inorganic semiconductors. Hybrid photovoltaics have organic materials that consist of conjugated polymers that absorb light as the donor and transport holes. Inorganic materials are used as the acceptor and electron transport. These devices have a potential for low-cost by roll-to-roll processing and scalable solar power conversion.

<span class="mw-page-title-main">Printed electronics</span> Electronic devices created by various printing methods

Printed electronics is a set of printing methods used to create electrical devices on various substrates. Printing typically uses common printing equipment suitable for defining patterns on material, such as screen printing, flexography, gravure, offset lithography, and inkjet. By electronic-industry standards, these are low-cost processes. Electrically functional electronic or optical inks are deposited on the substrate, creating active or passive devices, such as thin film transistors; capacitors; coils; resistors. Some researchers expect printed electronics to facilitate widespread, very low-cost, low-performance electronics for applications such as flexible displays, smart labels, decorative and animated posters, and active clothing that do not require high performance.

<span class="mw-page-title-main">Diindenoperylene</span> Chemical compound

Diindenoperylene (DIP) is an organic semiconductor which receives attention because of its potential application in optoelectronics (solar cells, OLEDs) and electronics (RFID tags). DIP is a planar perylene derivative with two indeno-groups attached to opposite sides of the perylene core. Its chemical formula is C32H16, the full chemical name is diindeno[1,2,3-cd:1',2',3'-lm]perylene. Its chemical synthesis has been described.

<span class="mw-page-title-main">PEDOT-TMA</span> Chemical compound

Poly(3,4-ethylenedioxythiophene)-tetramethacrylate or PEDOT-TMA is a p-type conducting polymer based on 3,4-ethylenedioxylthiophene or the EDOT monomer. It is a modification of the PEDOT structure. Advantages of this polymer relative to PEDOT are that it is dispersible in organic solvents, and it is non-corrosive. PEDOT-TMA was developed under a contract with the National Science Foundation, and it was first announced publicly on April 12, 2004. The trade name for PEDOT-TMA is Oligotron. PEDOT-TMA was featured in an article entitled "Next Stretch for Plastic Electronics" that appeared in Scientific American in 2004. The U.S. Patent office issued a patent protecting PEDOT-TMA on April 22, 2008.

Organic photovoltaic devices (OPVs) are fabricated from thin films of organic semiconductors, such as polymers and small-molecule compounds, and are typically on the order of 100 nm thick. Because polymer based OPVs can be made using a coating process such as spin coating or inkjet printing, they are an attractive option for inexpensively covering large areas as well as flexible plastic surfaces. A promising low cost alternative to conventional solar cells made of crystalline silicon, there is a large amount of research being dedicated throughout industry and academia towards developing OPVs and increasing their power conversion efficiency.

<span class="mw-page-title-main">Organic solar cell</span> Type of photovoltaic

An organic solar cell (OSC) or plastic solar cell is a type of photovoltaic that uses organic electronics, a branch of electronics that deals with conductive organic polymers or small organic molecules, for light absorption and charge transport to produce electricity from sunlight by the photovoltaic effect. Most organic photovoltaic cells are polymer solar cells.

<span class="mw-page-title-main">Transparent conducting film</span> Optically transparent and electrically conductive material

Transparent conducting films (TCFs) are thin films of optically transparent and electrically conductive material. They are an important component in a number of electronic devices including liquid-crystal displays, OLEDs, touchscreens and photovoltaics. While indium tin oxide (ITO) is the most widely used, alternatives include wider-spectrum transparent conductive oxides (TCOs), conductive polymers, metal grids and random metallic networks, carbon nanotubes (CNT), graphene, nanowire meshes and ultra thin metal films.

<span class="mw-page-title-main">Polyfluorene</span> Chemical compound

Polyfluorene is a polymer with formula (C13H8)n, consisting of fluorene units linked in a linear chain — specifically, at carbon atoms 2 and 7 in the standard fluorene numbering. It can also be described as a chain of benzene rings linked in para positions with an extra methylene bridge connecting every pair of rings.

<span class="mw-page-title-main">Contorted aromatics</span> Hydrocarbon compounds composed of rings fused such that the molecule is nonplanar

In organic chemistry, contorted aromatics, or more precisely contorted polycyclic aromatic hydrocarbons, are polycyclic aromatic hydrocarbons (PAHs) in which the fused aromatic molecules deviate from the usual planarity.

References

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