US20170301477A1 - Electro-polarizable compound and capacitor - Google Patents

Electro-polarizable compound and capacitor Download PDF

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Publication number
US20170301477A1
US20170301477A1 US15/449,587 US201715449587A US2017301477A1 US 20170301477 A1 US20170301477 A1 US 20170301477A1 US 201715449587 A US201715449587 A US 201715449587A US 2017301477 A1 US2017301477 A1 US 2017301477A1
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Prior art keywords
polarizable
unit
composite
composite oligomeric
capacitor
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Abandoned
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US15/449,587
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English (en)
Inventor
Pavel Ivan LAZAREV
Paul T. Furuta
Barry K. Sharp
Yan Li
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Capacitor Sciences Inc
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Capacitor Sciences Inc
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Priority to US15/449,587 priority Critical patent/US20170301477A1/en
Priority to JP2019503386A priority patent/JP2019520466A/ja
Priority to SG11201808716PA priority patent/SG11201808716PA/en
Priority to PCT/US2017/024150 priority patent/WO2017176477A1/en
Priority to CN201780026853.4A priority patent/CN109478460A/zh
Priority to CA3019919A priority patent/CA3019919A1/en
Priority to EP17779524.2A priority patent/EP3440681A4/en
Priority to TW106111417A priority patent/TW201809035A/zh
Assigned to CAPACITOR SCIENCES INCORPORATED reassignment CAPACITOR SCIENCES INCORPORATED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FURUTA, PAUL T, LI, YAN, SHARP, BARRY K, LAZAREV, PAVEL IVAN
Priority to US15/710,587 priority patent/US10319523B2/en
Publication of US20170301477A1 publication Critical patent/US20170301477A1/en
Priority to US16/243,906 priority patent/US10872733B2/en
Priority to US16/436,269 priority patent/US10755857B2/en
Priority to US16/924,809 priority patent/US20200343045A1/en
Abandoned legal-status Critical Current

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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/004—Details
    • H01G9/07—Dielectric layers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/024—Polyamines containing oxygen in the form of ether bonds in the main chain
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G4/00—Fixed capacitors; Processes of their manufacture
    • H01G4/002—Details
    • H01G4/018—Dielectrics
    • H01G4/06—Solid dielectrics
    • H01G4/14—Organic dielectrics
    • H01G4/18—Organic dielectrics of synthetic material, e.g. derivatives of cellulose
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/004—Details
    • H01G9/04—Electrodes or formation of dielectric layers thereon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate

Definitions

  • a capacitor is an energy storage device that stores an applied electrical charge for a period of time and then discharges it. It is charged by applying a voltage across two electrodes and discharged by shorting the two electrodes. A voltage is maintained until discharge even when the charging source is removed.
  • a capacitor blocks the flow of direct current and permits the flow of alternating current.
  • the energy density of a capacitor is usually less than for a battery, but the power output of a capacitor is usually higher than for a battery.
  • Capacitors are often used for various purposes including timing, power supply smoothing, coupling, filtering, tuning and energy storage. Batteries and capacitors are often used in tandem such as in a camera with a flash. The battery charges the capacitor that then provides the high power needed for a flash. The same idea works in electric and hybrid vehicles where batteries provide energy and capacitors provide power for starting and acceleration.
  • a capacitor is a passive electronic component that is used to store energy in the form of an electrostatic field, and comprises a pair of electrodes separated by a dielectric layer. When a potential difference exists between the two electrodes, an electric field is present in the dielectric layer.
  • An ideal capacitor is characterized by a single constant value of capacitance, which is a ratio of the electric charge on each electrode to the potential difference between them. For high voltage applications, much larger capacitors have to be used.
  • a dielectric material One important characteristic of a dielectric material is its breakdown field. This corresponds to the value of electric field strength at which the material suffers a catastrophic failure and conducts electricity between the electrodes.
  • the electric field in the dielectric can be approximated by the voltage between the two electrodes divided by the spacing between the electrodes, which is usually the thickness of the dielectric layer. Since the thickness is usually constant it is more common to refer to a breakdown voltage, rather than a breakdown field.
  • the geometry of the conductive electrodes is important factor affecting breakdown voltage for capacitor applications. In particular, sharp edges or points hugely increase the electric field strength locally and can lead to a local breakdown. Once a local breakdown starts at any point, the breakdown will quickly “trace” through the dielectric layer until it reaches the opposite electrode and causes a short circuit.
  • Breakdown of the dielectric layer usually occurs as follows. Intensity of an electric field becomes high enough to “pull” electrons from atoms of the dielectric material and makes them conduct an electric current from one electrode to another. Presence of impurities in the dielectric or imperfections of the crystal structure can result in an avalanche breakdown as observed in semiconductor devices.
  • dielectric permittivity Another important characteristic of a dielectric material is its dielectric permittivity.
  • dielectric materials include ceramics, polymer film, paper, and electrolytic capacitors of different kinds.
  • the most widely used polymer film materials are polypropylene and polyester. Increasing dielectric permittivity allows for increasing volumetric energy density, which makes it an important technical task.
  • One method for creating dielectrics with high permittivity is to use highly polarizable materials which when placed in between two electrodes and subjected to an electric field can more easily absorb more electrons due to polarized ends of the molecule orienting toward oppositely charged electrodes.
  • U.S. patent application Ser. No. 15/043,186 (Attorney Docket No. CSI-019A) demonstrates a method of incorporating highly polarizable molecules into an oligomer to create such a dielectric material and is hereby incorporated in its entirety by reference.
  • Disperse Red 1 (DR1) was attached to Si atoms by a carbamate linkage to provide the functionalized silane via the nucleophilic addition reaction of 3-isocyanatopropyl triethoxysilane (ICTES) with DR1 using triethylamine as catalyst.
  • ICTES 3-isocyanatopropyl triethoxysilane
  • the physical properties and structure of ICTES-DR1 were characterized using elemental analysis, mass spectra, 1 H-NMR, FTIR, UV-visible spectra and differential scanning calorimetry (DSC). ICTES-DR1 displays excellent solubility in common organic solvents.
  • NLO nonlinear optical
  • Chromophoric orientation is obtained by applying a static electric field or by optical poling. Whatever the poling process, poled-order decay is an irreversible process which tends to annihilate the NLO response of the materials and this process is accelerated at higher temperature.
  • the most probable candidate must exhibit inherent properties that include: (i) high thermal stability to withstand heating during poling; (ii) high glass transition temperature (T g ) to lock the chromophores in their acentric order after poling.
  • the first example presents the joint theoretical/experimental characterization of a new family of multi-addressable NLO switches based on benzazolo-oxazolidine derivatives.
  • the second focuses on the photoinduced commutation in merocyanine-spiropyran systems, where the significant NLO contrast could be exploited for metal cation identification in a new generation of multiusage sensing devices.
  • Castet et. al. illustrated the impact of environment on the NLO switching properties, with examples based on the keto-enol equilibrium in aniline derivatives. Through these representative examples, Castet et. al. demonstrated that the rational design of molecular NLO switches, which combines experimental and theoretical approaches, has reached maturity. Future challenges consist in extending the investigated objects to supramolecular architectures involving several NLO-responsive units, in order to exploit their cooperative effects for enhancing the NLO responses and contrasts.
  • the molecular structure, molecular weight distribution, film morphology, and optical and thermal properties of these polythiophene derivatives were determined by NMR, FT-IR, UV-Vis GPC, DSC-TGA, and AFM.
  • the third-order nonlinear optical response of these materials was performed with nanosecond and femtosecond laser pulses by using the third-harmonic generation (THG) and Z-scan techniques at infrared wavelengths of 1300 and 800 nm, respectively. From these experiments it was observed that although the TRD19 incorporation into the side chain of the copolymers was lower than 5%, it was sufficient to increase their nonlinear response in solid state.
  • the third-order nonlinear electric susceptibility of solid thin films made of these copolymers exhibited an increment of nearly 60% when TDR19 incorporation increased from 3% to 5%.
  • Scale invariance was used to estimate fundamental limits for these polarizabilities.
  • ⁇ (1) ij , ⁇ (2) ijk , ⁇ (3) ijkl symmetry determines whether a molecule can support second-order nonlinear processes or not.
  • examples of the frequency dispersion based on a two-level model ground state and one excited state
  • examples of the ⁇ ijk are the simplest possible for ⁇ ijk and examples of the resulting frequency dispersion were given.
  • the third-order susceptibility is too complicated to yield simple results in terms of symmetry properties.
  • Single crystals of doped aniline oligomers can be produced via a simple solution-based self-assembly method (see Yue Wang et. al., “Morphological and Dimensional Control via Hierarchical Assembly of Doped Oligoaniline Single Crystals”, J. Am. Chem. Soc. 2012, v. 134, pp. 9251-9262).
  • Detailed mechanistic studies reveal that crystals of different morphologies and dimensions can be produced by a “bottom-up” hierarchical assembly where structures such as one-dimensional (1-D) nanofibers can be aggregated into higher order architectures.
  • a large variety of crystalline nanostructures including 1-D nanofibers and nanowires, 2-D nanoribbons and nanosheets, 3-D nanoplates, stacked sheets, nanoflowers, porous networks, hollow spheres, and twisted coils can be obtained by controlling the nucleation of the crystals and the non-covalent interactions between the doped oligomers.
  • These nanoscale crystals exhibit enhanced conductivity compared to their bulk counterparts as well as interesting structure—property relationships such as shape—dependent crystallinity. Further, the morphology and dimension of these structures can be largely rationalized and predicted by monitoring molecule—solvent interactions via absorption studies.
  • doped tetraaniline as a model system, the results and strategies presented by Yue Wang et. al. provide insight into the general scheme of shape and size control for organic materials.
  • Hu Kang et. al. detail the synthesis and chemical/physical characterization of a series of unconventional twisted ⁇ -electron system electro-optic (EO) chromophores (“Ultralarge Hyperpolarizability Twisted ⁇ -Electron System Electro-Optic Chromophores: Synthesis, Solid-State and Solution-Phase Structural Characteristics, Electronic Structures, Linear and Nonlinear Optical Properties, and Computational Studies”, J. AM. CHEM. SOC. 2007, vol. 129, pp. 3267-3286).
  • EO electro-optic
  • Crystallographic analysis of these chromophores reveals large ring-ring dihedral twist angles (80-89°) and a highly charge-separated zwitterionic structure dominating the ground state.
  • NOE NMR measurements of the twist angle in solution confirm that the solid-state twisting persists essentially unchanged in solution.
  • Optical, IR, and NMR spectroscopic studies in both the solution phase and solid state further substantiate that the solid-state structural characteristics persist in solution.
  • the aggregation of these highly polar zwitterions is investigated using several experimental techniques, including concentration-dependent optical and fluorescence spectroscopy and pulsed field gradient spin-echo (PGSE) NMR spectroscopy in combination with solid-state data.
  • PGSE pulsed field gradient spin-echo
  • SA-CASSCF state-averaged complete active space self-consistent field
  • U.S. Pat. No. 5,395,556 Tricyanovinyl Substitution Process for NLO Polymers demonstrate NLO effect of polymers that specifies a low dielectric constant.
  • U.S. patent application Ser. No. 11/428,395 High Dielectric, Non-Linear Capacitor develops high dielectric materials with non-linear effects. It appears to be an advance in the art to achieve non-linear effects through supramolecular chromophore structures that are insulated from each other that include doping properties in the connecting insulating or resistive elements to the composite organic compound. It further appears to be an advance in the art to combine composite organic compounds with non-linear effects that form ordered structures in a film and are insulated from each other and do not rely on forming self-assembled monolayers on a substrate electrode.
  • Capacitors as energy storage device have well-known advantages versus electrochemical energy storage, e.g. a battery. Compared to batteries, capacitors are able to store energy with very high power density, i.e. charge/recharge rates, have long shelf life with little degradation, and can be charged and discharged (cycled) hundreds of thousands or millions of times. However, capacitors often do not store energy in small volume or weight as in case of a battery, or at low energy storage cost, which makes capacitors impractical for some applications, for example electric vehicles. Accordingly, it may be an advance in energy storage technology to provide capacitors of higher volumetric and mass energy storage density and lower cost.
  • the capacitor of the present disclosure builds on past work on non-linear optical chromophores and non-linear capacitors comprising said chromophores.
  • the capacitors used do not have high dielectric losses.
  • ferroelectric ceramic capacitors with a high dielectric constant the presence of domain boundaries and electrostriction provide loss mechanisms that are significant.
  • the high dielectric mechanism disclosed in this disclosure involves the movement of an electron in a long molecule and its fixed donor. This occurs extremely rapidly so that losses even at gigahertz frequencies are small.
  • a second very useful property of the type of capacitor disclosed in the disclosure is its non-linearity.
  • the disclosed capacitors have such a property; as the mobile electron moves to the far end of the chromophore as the voltage increases, its motion is stopped so that with additional voltage little change in position occurs. As a consequence, the increase in the electric moment of the dielectric is reduced resulting in a diminished dielectric constant.
  • a third useful property of the type of capacitor disclosed in the disclosure is its resistivity due to ordered resistive tails covalently bonded to the composite organic compound.
  • electron mobility is hindered by a matrix of resistive materials.
  • Ordered resistive tails can enhance the energy density of capacitors by increasing the density of polarization units in organized structures such as lamella or lamella-like or micelle structures, while also limiting mobility of electrons on the chromophores.
  • the ordered resistive tails may also crosslink to further enhance the structure of the dielectric film which can reduce localized film defects and enhance the film's breakdown voltage or field.
  • ordered resistive tails can improve solubility of the composite compound in organic solvents. Still further, the ordered resistive tails act to hinder electro-polar interactions between supramolecular structures formed from pi-pi stacking of the optionally attached polycyclic conjugated molecule.
  • resistive tails may be rigid in structure, thereby stabilizing pi-pi stacking by holding the individual ring system in place and stabilizing the overall material by preventing the presence of voids due to coiling of alkyl chains. This is described in greater detail in U.S. patent application Ser. No. 15/043,247 (Attorney Docket No. CS1-51B), which is incorporated herein in its entirety by reference.
  • a fourth very useful property of the type of capacitor disclosed in the disclosure is enhancing the non-linear response of the chromophores by using non-ionic dopant groups to change electron density of the chromophores.
  • Manipulation of the electron density of the chromophores can significantly increase the non-linear response which is useful for increasing the polarizability and the type of dopant groups on chromophores is also important to achieving enhanced non-linear polarization versus a neutral or deleterious effect on the non-linearity of the chromophore.
  • a fifth very useful property of the type of capacitor disclosed in the disclosure is enhancing the non-linear response of the chromophores by using non-ionic dopant connecting groups to change electron density of the chromophores.
  • Manipulation of the electron density of the chromophores can significantly increase the non-linear response which is useful for increasing the polarization of the capacitor and thus energy density of said capacitor.
  • placement and type of dopant connecting groups on chromophores is also important to achieving enhanced non-linear polarization versus a neutral or deleterious effect on the non-linearity of the chromophore.
  • FIG. 1 shows a metacapacitor with two electrodes and a metadielectric according to aspects of the present disclosure.
  • FIG. 2A shows a formation of two metal strips on top and bottom surfaces of the plastic layer for a coiled metacapacitor according to an aspect of the present disclosure.
  • FIG. 2B shows a winding of the multilayered tape for a coiled metacapacitor according to an aspect of the present disclosure.
  • FIG. 3 shows a coiled film metacapacitor according to an aspect of the present disclosure.
  • FIG. 4 shows an example of a chemical structure of a YanLi material that may be used to form a metadielectric for a metacapacitor according to aspects of the present disclosure.
  • a YanLi material is a composite oligomeric material comprised of monomers that have polarizable and insulating components.
  • the monomers may include a polarizable unit having a non-linear polarizable core that includes a conjugated ring system and at least one dopant group.
  • the monomers also include an insulating tail as a side chain on the polarizable unit, on the handle linking a polarizable unit to the monomer backbone, or directly attached to the monomer backbone. Additionally, the polarizable unit may be partially or fully incorporated into the monomer backbone.
  • a particular subclass of YanLi materials are referred to herein as YanLi dielectrics, which are polymers of one or more YanLi materials.
  • One aspect of the present disclosure is to provide a capacitor with a high power output.
  • a further aspect of the present disclosure is to provide a capacitor featuring a high dielectric constant sustainable to high voltage.
  • a still further aspect of the present disclosure is to provide a capacitor featuring voltage dependent capacitance.
  • a method to make such a capacitor is provided.
  • the capacitor in its simplest form, comprises a first electrode, a second electrode and a composite oligomer between the first electrode and the second electrode.
  • the composite oligomer includes resistive tails and polarizable oligomer groups attached as a pendant to a monomer backbone or incorporated in a monomer backbone forming a composite monomer.
  • the polarizable unitson the monomer backbone may have dopant groups which can be independently selected from electron acceptor and electron donor groups separated by a conjugated ring system with or without a conjugated bridge.
  • the conjugated bridge comprises one or more double bonds that alternate with single bonds in an unsaturated compound. Among the many elements that may be present in the double bond, carbon, nitrogen, oxygen and sulfur are the most preferred heteroatoms.
  • the ⁇ electrons in the conjugated ring system are delocalized across the length of the ring system.
  • resistive tails that may be present in the composite monomer
  • alkyl chains, branched alkyl chains, fluorinated alkyl chains, branched flouroalkyl chains, poly(methyl methacrylate) chains are examples.
  • the composite oligomer becomes more or less polarized with electron density moving to compensate the field induced by the applied bias.
  • the capacitor comprises a plurality of YanLi oligomers (varying in length and/or type of monomer units) as a structured dielectric film.
  • an energy storage device such as a capacitor
  • Conductors include, but are not limited to, metals, conducting polymers, carbon nano-materials, and graphite including graphene sheets.
  • Semiconductors include, but are not limited to, silicon, germanium, silicon carbide, gallium arsenide and selenium.
  • the electrode may or may not be formed on a flat support.
  • Flat supports may include, but are not limited to, glass, plastic, silicon, and metal surfaces.
  • the present disclosure provides a metacapacitor comprising two metal electrodes positioned parallel to each other and which can be rolled or flat and planar and a metadielectric layer between said electrodes and optionally an insolation layer.
  • the metadielectric layer comprises the electro-polarizable compounds as disclosed below.
  • a metadielectric layer may be a film made from composite oligomers referred to herein as YanLi materials.
  • Such a composite oligomeric material is characterized by a chemical structure that includes a repeating backbone unit, a polarizable unit, and a resistive tail.
  • the polarizable unit may be incorporated into or connected as a pendant to the backbone unit and the resistive tail may be connected to the backbone unit or polarizable unit or a separate backbone unit.
  • polarizable unit to mean any multicyclic arrangement where electrons are delocalized over the entire portion of the chemical structure via conjugated single and double bonds.
  • anisometric is defined as the condition of a molecule possessing charge or partial charge asymmetry along an axis. Possible, non-limiting, forms of this conjugation are polycyclic fused aromatic systems or a conjugated bridge where aromatic systems are connected by alternating single and double bonds.
  • the metadielectric layer maybe comprised of any organic composite oligomers, compounds, or polymers as disclosed in U.S. patent application Ser. No. 14/710,491 (attorney docket number CSI-003) filed May 12, 2015, Ser. No. 15/043,186 (attorney docket number CSI-019A) filed Feb. 12, 2016, Ser. No. 15/043,209 (attorney docket number CSI-019B) filed Feb. 12, 2016, Ser. No. 15/194,224 (attorney docket number CSI-044) filed Jun. 27, 2016, Ser. No. 15/043,247 (attorney docket number CSI-046) filed Feb. 12, 2016, Ser. No.
  • FIG. 1 illustrates an example of a metacapacitor having a first electrode 1 , a second electrode 2 , and a metadielectric layer 3 disposed between said first and second electrodes.
  • the electrodes 1 and 2 may be made of a metal, such as copper, zinc, or aluminum or other conductive material such as graphite or carbon nanomaterials and are generally planar in shape.
  • the electrodes 1 , 2 may be flat and planar and positioned parallel to each other.
  • the electrodes may be planar and parallel, but not necessarily flat, they may be coiled, rolled, bent, folded, or otherwise shaped to form the capacitor. It is also possible for the electrodes to be non-flat, non-planar, or non-parallel or some combination of two or more of these.
  • a spacing d between the electrodes 1 and 2 may range from about 3 nm to about 100 ⁇ m.
  • the metacapacitor may have an insulation layer to insulate electrodes 1 and 2 from making ohmic contact with each other in coiled, rolled, bent, and folded embodiments.
  • the insolation layer include metadielectric material, polypropylene (PP), polyethylene terephthalate polyester (PET), polyphenylene sulfide (PPS), polyethylene naphthalate (PEN), polycarbonate (PP), polystyrene (PS), and polytetrafluoroethylene (PTFE).
  • the electrodes 1 and 2 may have the same shape as each other, the same dimensions, and the same area A.
  • the area A of each electrode 1 and 2 may range from about 0.01 m 2 to about 1000 m 2 .
  • the capacitance C of the capacitor may be approximated by the formula:
  • ⁇ o is the permittivity of free space (8.85 ⁇ 10 ⁇ 12 Coulombs 2 /(Newton ⁇ meter 2 )) and ⁇ is the dielectric constant of the dielectric layer.
  • the energy storage capacity U of the capacitor may be approximated as:
  • the energy storage capacity U is determined by the dielectric constant ⁇ , the area A, the electrode spacing d, and the breakdown field E bd .
  • a capacitor or capacitor bank may be designed to have any desired energy storage capacity U.
  • a capacitor in accordance with aspects of the present disclosure may have an energy storage capacity U ranging from about 500 Joules to about 2 ⁇ 10 16 Joules.
  • a capacitor of the type described herein may have a specific energy capacity per unit mass ranging from about 10 W ⁇ h/kg up to about 100,000 W ⁇ h/kg, though implementations are not so limited.
  • electrodes 1 and 2 may have different shapes from each other with the same or different dimensions, and the same or different areas.
  • the present disclosure includes metacapacitors that are coiled, e.g., as depicted in FIGS. 2A, 2B and 3 .
  • electrodes 19 , 21 e.g., metal electrodes
  • margin portions 18 , 20 that are free of metal located on opposite edges of the metadielectric layer 17 .
  • an electrically insulating layer 15 e.g., a plastic material is formed over one of the electrodes 21 or a plastic film is overlaid on one of the electrodes 21 .
  • the electrically insulating layer 15 may include metadielectric materials or common capacitor insulating materials such as PET.
  • the metadielectric lay 17 may be formed, e.g., by applying a solution containing YanLi material to the electrode 19 and then drying the applied solution to form a solid layer of the YanLi material.
  • electrodes 19 and 21 may be formed onto opposite surfaces of an insulating layer 15 with margin portions 18 , 20 that are free of electrode material located on opposite edges of the insulating layer 15 .
  • a configuration of electrodes 19 , 21 and insulating layer 15 form a tape or a multilayered tape.
  • the electrically insulating layer 15 may include metadielectric materials or common capacitor insulating materials such as PET.
  • the metadielectric lay 17 may be formed, e.g., by applying a solution containing YanLi material to the electrode 19 and then drying the applied solution to form a solid layer of the YanLi material.
  • the applied YanLi material may be a polymerized solution of YanLi oligomers which is dried to form a metadielectric.
  • the YanLi material may be polymerized to form a metadielectric.
  • the thickness of the metadielectric layer may be a relatively uniformly thick layer.
  • the metadielectric layer thickness may range from 0.1 ⁇ m to 50 ⁇ m depending on the desired maximum capacitor voltage. In general thicker metadielectric layers are used for higher maximum capacitor voltages.
  • the metadielectric layer thickness may vary due to normal manufacturing process variations, e.g., by about 1% to 10% of a nominal thickness value. In the example shown in FIG.
  • the first metal electrode 19 is formed on a portion of a first surface of the metadielectric layer 17 with a first margin portion 18 that is free of metal.
  • the second electrode 21 is formed on a portion of a second surface of the plastic layer with a second margin portion 20 located on an opposite edge of the metadielectric layer 17 being free of metal.
  • the multilayered structure depicted in FIG. 2A may be wound into a coil as shown in FIG. 2B .
  • the insulating layer 15 prevents undesired electrical shorts between the first and second electrodes after being wound into the coil.
  • the insulating layer 15 may include a metadielectric material, polypropylene (PP), polyethylene terephthalate polyester (PET), polyphenylene sulfide (PPS), polyethylene naphthalate (PEN), polycarbonate (PP), polystyrene (PS), or polytetrafluoroethylene (PTFE).
  • PP polypropylene
  • PET polyethylene terephthalate polyester
  • PPS polyphenylene sulfide
  • PEN polyethylene naphthalate
  • PP polycarbonate
  • PS polystyrene
  • PTFE polytetrafluoroethylene
  • a metacapacitor 22 comprises a first electrode 23 , a second electrode 25 , and a metadielectric material layer 24 of the type described herein disposed between said first and second electrodes.
  • the electrodes 23 and 25 may be made of a metal, such as copper, zinc, or aluminum or other conductive material such as graphite or carbon nanomaterials and are generally planar in shape.
  • the electrodes and metadielectric material layer 24 are in the form of long strips of material that are sandwiched together and wound into a coil along with an insulating material 26 , e.g., a plastic film such as polypropylene or polyester to prevent electrical shorting between the electrodes 23 and 25 .
  • the insulating material may include a metadielectric layer comprised of any composite oligomer or polymer formed therefrom, as described herein below.
  • suitable coiled capacitors are described in and U.S. patent application Ser. No. 14/752,600 (Attorney Docket No. CSI-017) which is herein incorporated by reference in their entirety.
  • the present invention provides a coiled capacitor comprising a coil formed by a flexible multilayered tape, and a first terminating electrode (a first contact layer) and a second terminating electrode (a second contact layer) which are located on butts of the coil.
  • the flexible multilayered tape contains the following sequence of layers: first metal layer, a layer of a plastic, second metal layer, a layer of energy storage material.
  • the first metal layer forms an ohmic contact with the first terminating electrode (the first contact layer) and the second metal layer (the second contact layer) forms an ohmic contact with the second terminating electrode.
  • the layer of energy storage material may be any oligomer or polymer described herein
  • FIG. 4 illustrates an example of the in the chemical structure of a YanLi material as a monomer of a polymer, wherein the polarizable unit is a doped chromophore 48 , having an electron donor 44 , two conjugated bridges 43 , an electron acceptor 42 ; and where in the tail 41 is covalently bounded to the electron donor group 44 .
  • a composite oligomer forming the polarizable unit can have more than one electron donor 44 , electron acceptor 42 , and tail 41 .
  • the composite oligomer forming the polarizable unit has an aromatic ring system in conjugation with a conjugated bridge.
  • the aromatic ring system consists of fused aromatic rings in conjugation.
  • a composite oligomer may comprise a mixture of molecules.
  • a YanLi material made of monomers of the type shown in FIG. 4 may be polymerized to form a YanLi dielectric.
  • the layer's relative permittivity is greater than or equal to 1000.
  • the polarization (P) of the metadielectric layer comprises first-order ( ⁇ (1) ) and second-order ( ⁇ (2) ) and third order ( ⁇ (3) ) permittivities according to the following formula:
  • permittivity of a capacitor is a function of applied voltage and thickness of the capacitor's dielectric (d). Where voltage is the DC-voltage which is applied to the metadielectric layer, and d is the layer thickness.
  • the layer's resistivity is greater than or equal to 10 15 ohm cm.
  • the layer's resistivity is between 10 16 ohm cm and 10 22 ohm cm.
  • the composite oligomer comprises more than one type of resistive tails. In another embodiment, the composite oligomer comprises more than one type of ordered resistive tails. In yet another embodiment, the composite oligomer comprises at least one type of resistive tail or at least one type of ordered resistive tails.
  • a liquid or solid composite oligomer is placed between the first and second electrodes.
  • a solid chromophore is, for example, pressed into a pellet and placed between the first electrode and the second electrode.
  • the chromophore can be ground into a powder before pressing.
  • At least one type of YanLi material or YanLi oligomer may be dissolved or suspended in a solvent.
  • the resultant material can be spin coated, extruded via slot die, roll-to-roll coated, or pulled and dried to form a dielectric film.
  • a tailless composite oligomer may be dissolved or suspended in a polymer.
  • This is termed a “guest-host” system where the oligomer is the guest and the polymer is the host.
  • Polymer hosts include, but are not limited to, poly(methyl methacrylate), polyimides, polycarbonates and poly(c-caprolactone). These systems are cross-linked or non-cross-linked.
  • a tailless composite oligomer may be attached to a polymer. This is termed a “side-chain polymer” system. This system has the advantages over guest-host systems because high composite oligomer concentrations are incorporated into the polymer with high order and regularity and without phase separation or concentration gradients.
  • Side chain polymers include, but are not limited to, poly[4-(2,2-dicyanovinyl)-N-bis(hydroxyethyl)aniline-alt-(4,4′-methylenebis(phenylisocyanate))]urethane, poly[4-(2,2-dicyanovinyl)-N-bis(hydroxyethyl)aniline-alt-(isophoronediisocyanate)]urethane, poly(9H-carbazole-9-ethyl acrylate), poly(9H-carbazole-9-ethyl methacrylate), poly(Disperse Orange 3 acrylamide), poly(Disperse Orange 3 methacrylamide), poly(Disperse Red 1 acrylate), poly(Disperse Red 13 acrylate), poly(Disperse Red 1 methacrylate), poly(Disperse Red 13 methacrylate), poly[(Disperse Red 19)-alt-(1,4-diphenylmethane urethane)], poly(Disp
  • tailless composite oligomers may be embedded in matrices such as oxides, halides, salts and organic glasses.
  • matrices such as oxides, halides, salts and organic glasses.
  • An example of a matrix is inorganic glasses comprising the oxides of aluminum, boron, silicon, titanium, vanadium and zirconium.
  • the oligomers that make up a YanLi material may be aligned, partially aligned or unaligned.
  • the composite oligomer is preferably aligned for optimal geometric configuration of polarizing units as this results in higher capacitance values in the capacitor.
  • One method of alignment is to apply a DC electric field to the composite oligomer at a temperature at which the composite oligomer can be oriented. This method is termed “poling.” Poling is generally performed near the glass transition temperature of polymeric and glassy systems.
  • One possible method of poling is corona poling.
  • Other methods of alignment could be roll-to-roll, Meyer bar, dip, slot die, and air knife coating of solutions and liquid crystal solutions of said side-chain polymers or composite oligomers.
  • the side-chain polymer or composite oligomers may form liquid crystals in solution or solvent and with or without external influence.
  • liquid crystals include lyotropic and thermotropic liquid crystals.
  • external influences include heat, electric field, mechanical disturbances (e.g. vibration or sonication), and electromagnetic radiation.
  • Said liquid crystals are supramolecular structures comprised of said side-chain polymers or composite oligomer in solution or solvent and are ordered and aligned or partially ordered or partially aligned.
  • Such liquid crystal materials may be coated onto a substrate, e.g., by roll-to-roll, Meyer bar, dip, slot die, or air knife coating in a process that includes mechanical ordering of the liquid crystals, and drying of the liquid crystal solution or evaporation of the solvent such that the liquid crystals form a crystalline or semi-crystalline layer or film of metadielectric material.
  • structures 1-4 in Table 1 below are possible general structures for YanLi materials.
  • the term “Polar Unit” is equivalent to polarizable unit as defined above, “t” is an integer representing the number of repeat units of the oligomeric material, and “n” and “m” are integers representing the number of subunits present in the composite oligomeric material.
  • rylene fragments are a possible implementation of the polarizable unit.
  • Some non-limiting examples of the use of rylene fragments as the polarizable unit are listed in Table 2. These polarizable units could be incorporated as sidechains to the oligomer via a wide variety of linkers or used as crosslinking agents to join polymers into a polymer network.
  • Use of rylenes in capacitors is described in greater detail in U.S. patent application Ser. No. 14/919,337 (Attorney Docket No. CS1-022), which is incorporated herein in its entirety by reference.
  • Table 2 includes examples of rylene fragments, wherein the repeat unit can range from 0 to 8 repeats.
  • the rylene fragments may be made further polarizable by adding a variety of functional groups to various positions of the structure. Incorporating electron donors and electron acceptors is one way to enhance the polarizability.
  • Electrophilic groups are selected from —NO 2 , —NH 3 + and —NR 3 + (quaternary nitrogen salts), counterion Cl ⁇ or Br ⁇ , —CHO (aldehyde), —CRO (keto group), —SO 3 H (sulfonic acids), —SO 3 R (sulfonates), SO 2 NH 2 (sulfonamides), —COOH (carboxylic acid), —COOR (esters, from carboxylic acid side), —COCl (carboxylic acid chlorides), —CONH 2 (amides, from carboxylic acid side), —CF 3 , —CCl 3 , —CN, wherein R is radical selected from the list comprising alkyl (methyl, ethyl), quatern
  • Nucleophilic groups are selected from —O ⁇ (phenoxides, like —ONa or —OK), —NH 2 , —NHR, —NR 2 , —NRR′, —OH, OR (ethers), —NHCOR (amides, from amine side), —OCOR (esters, from alcohol side), alkyls, —C 6 H 5 , vinyls, wherein R and R′ are radicals independently selected from the list comprising alkyl (methyl, ethyl, isopropyl, tent-butyl, neopentyl, cyclohexyl etc.), allyl (—CH2-CH ⁇ CH2), benzyl (—CH2C6H5) groups, phenyl (+substituted phenyl) and other aryl (aromatic) groups.
  • Preferred electron donors include, but are not limited to, amino and phosphino groups and combinations thereof.
  • Preferred electron acceptors include, but are not limited to, nitro, carbonyl, oxo, thioxo, sulfonyl, malononitrile, isoxazolone, cyano, dicyano, tricyano, tetracycano, nitrile, dicarbonitrile, tricarbonitrile, thioxodihydropyrimidinedione groups and combinations thereof.
  • More conjugated bridges include, but are not limited to, 1,2-diphenylethene, 1,2-diphenyldiazene, styrene, hexa-1,3,5-trienylbenzene and 1,4-di(thiophen-2-yl)buta-1,3-diene, alkenes, dienes, trienes, polyenes, diazenes and combinations thereof.
  • the presence of the polarizable units leads to increasing of polarization ability of the disclosed material because of electronic conductivity of the polarizable units.
  • Ionic groups may increase polarization of the disclosed YanLi material.
  • the polarizable units can be nonlinearly polarizable and may be comprised of an aromatic polycyclic conjugated molecule with at least one dopant group, the polarizable units and are placed into a resistive envelope formed by resistive substituents.
  • the resistive substituents provide solubility of the organic compound in a solvent and act to electrically insulate supramolecular structures comprised of the YanLi material from neighboring supramolecular structures of the YanLi material.
  • a non-centrosymmetric arrangement of the dopant group(s) can lead to a strong nonlinear response of the compound's electronic polarization in the presence of an electric field.
  • an anisometric molecule or polarizing unit can lead to a strong nonlinear response of the compound's electronic polarization in the presence of an electric field.
  • Resistive substituents e.g. resistive tails described above
  • one or both ends of the rylene fragment may be attached to a polymer chain via T, T p , or T′ p , and may be functionalized for better polarizability at R m , R′ m , R 1 , R 2 , R 3 , or R 4 .
  • the preferred but non-limiting range for n, n 1 , n 2 , and n 3 are between 0 and 8, with the proviso that the rylene fragment needs at least one naphthalene unit in order to be considered a rylene fragment and n, n 1 , n 2 , and n 3 are independently selected from said range of integers.
  • Rylene fragments may also be fused with anthracene structures at the nitrogen containing ends. Some non-limiting examples are shown below. These species will similarly benefit in polarizability by the addition of dopant groups, as illustrated in the examples below.
  • R 1 , R 2 , R 3 , and R 4 substituents are independently absent, a resistive tail, or a dopant group in each occurrence
  • R A 1 , R A′ 1 , R A′′ 1 , R A′′′ 1 , R A′′′′ 1 , and R A′′′′′ 1 are each independently absent, a resistive tail, or a dopant group
  • each occurrence of n 1 , n 2 , and n 3 can be any integer independently selected from 0 to 8 with the provision that not all n 1 , n 2 , and n 3 values can equal 0.
  • the composite oligomer may include a repeating backbone and a polarizable unit in the form of one or more azo-dye chromophores.
  • the azo-dye chromophores may be phenyl groups in conjugated connection via an azo-bridge, such that there are “n” phenyl groups and “n ⁇ 1” azo-bridges where n is an integer between 2 and 16.
  • the repeating backbone may contain a portion of the chromophore or possess a handle allowing the chromophore to be present as sidechains. Sidechains may be added to the final polymerized product or incorporated into individual monomers that are then polymerized. If incorporated into the backbone the chromophores may be modified such that they react with the other segments of the backbone to form the final product or they may be incorporated into monomers that are then polymerized.
  • the composite oligomer may further include resistive tails that will provide insulation within the material.
  • the resistive tails can be substituted or unsubstituted carbon chains (C n X 2n+1 , where “X” represents hydrogen, fluorine, chlorine, or any combination thereof).
  • the resistive tails may be rigid fused polycyclic aryl groups in order to limit the motion of the sidechains, potential stabilizing van der Waals interactions between sidechains while simultaneously making the material more stable by eliminating voids.
  • the resistive tails may be rigid in order to limit voids within the material.
  • repeating backbones include, but are not limited to, (meth)acrylates, polyvinyls, peptides, peptoids, and polyimides.
  • chromophores examples include, but are not limited to, Disperse Red-1, Black Hole Quencher-1, and Black Hole Quencher-2. In many of the embodiments it may not be necessary for all monomer units to bear a chromophore, and in some it may be desirable to possess other side chains or sites within the repeating backbone that impart other qualities to the material such as stability, ease of purification, flexibility of finished film, etc.
  • the resistive tails may be added before the sidechains are attached to a finished oligomer, after sidechains have been chemically added to a finished oligomer, or incorporated into the oligomer during synthesis by incorporation into monomer units.
  • the tails may be attached to the finished composite oligomer or incorporated into monomer units and added during composite synthesis.
  • Non-limiting examples of suitable tails are alkyl, haloalkyl, cycloakyl, cyclohaloalkyl, and polyether.
  • reaction solution was filtered and THF was used to wash the insoluble; the filtrate was concentrated under vacuum and diluted in dichloromethane. The diluted solution was washed with water and the solvent was removed under vacuum. The crude product was purified with column chromatography and 3.2 g pure product was isolated as a black powder.
  • Polymer 1 Compound 2 (2.0 g), stearylmethacrylate (1.2 g) and AIBN (160 mg) were dissolved in anhydrous toluene (12 mL) in a sealed flask and the resulting solution was heated to 85° C. for 18 hours and then cooled to room temperature. The polymer was obtained by precipitating in isopropanol.
  • Polymer 2 was synthesized from compound 3 and stearylmethacrylate using preparation procedure of polymer 1.
  • reaction solution was filtered and THF was used to wash the insoluble; the filtrate was concentrated under vacuum and residue was taken in dichloromethane.
  • the crude product solution was washed with water and the solvent was removed under vacuum. The crude product was purified with column chromatography.
  • the pure product was dissolved in dichloromethane (10 mL) and TFA (3 mL) and the solution was stirred at room temperature for 2 hours. Then excess reagent and solvent were removed under vacuum. The resulting crude product was neutralized by NaHCO 3 solution, extracted with CH 2 Cl 2 (3 ⁇ 50 mL), dried over MgSO 4 and evaporated. The crude product was purified by silica column chromatography.

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SG11201808716PA SG11201808716PA (en) 2016-04-04 2017-03-24 Yanli material and dielectric and capacitor thereof
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CN201780026853.4A CN109478460A (zh) 2016-04-04 2017-03-24 Yanli材料及其电解质和电容器
CA3019919A CA3019919A1 (en) 2016-04-04 2017-03-24 Yanli material and dielectric and capacitor thereof
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TW106111417A TW201809035A (zh) 2016-04-04 2017-04-05 ＹａｎＬｉ材料及含彼之介電質和電容器
US15/710,587 US10319523B2 (en) 2014-05-12 2017-09-20 Yanli dielectric materials and capacitor thereof
US16/243,906 US10872733B2 (en) 2016-04-04 2019-01-09 YanLi material and dielectric and capacitor thereof
US16/436,269 US10755857B2 (en) 2014-05-12 2019-06-10 Yanli dielectric materials and capacitor thereof
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