CN110323335B - Application of natural blue pigment in organic semiconductor device - Google Patents

Application of natural blue pigment in organic semiconductor device Download PDF

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CN110323335B
CN110323335B CN201910566277.3A CN201910566277A CN110323335B CN 110323335 B CN110323335 B CN 110323335B CN 201910566277 A CN201910566277 A CN 201910566277A CN 110323335 B CN110323335 B CN 110323335B
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blue pigment
natural blue
thickness
semiconductor device
organic semiconductor
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CN110323335A (en
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占纪勋
亚历山大·科瓦连科
席克丹姆·尤姆萨克
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Hangzhou Viablife Biotechnology Co ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene

Abstract

The invention relates to the field of semiconductors, in particular to application of a natural blue pigment in an organic semiconductor device. The invention aims to provide an application of natural blue pigment in an organic semiconductor device. The natural blue pigment has a narrow band gap of 1.7eV, also has a very high molar extinction coefficient, is nearly in a planar structure, allows the combination of hydrogen bonds in molecules and among molecules and has a good adaptability energy level, is a mark of high charge carrier mobility, so that the natural blue pigment has a bipolar energy carrier characteristic, and an organic semiconductor device using the natural blue pigment has excellent optical characteristics and electrical characteristics.

Description

Application of natural blue pigment in organic semiconductor device
Technical Field
The invention relates to the field of semiconductors, in particular to application of a natural blue pigment in an organic semiconductor device.
Background
Over the past decades, semiconducting organic materials have been of particular interest to the industry because of their flexibility, ease of processing, low manufacturing cost, and large area fabrication (large area fabrication). Although organic semiconductors are considered more "environmentally friendly" due to their low processing temperatures, ease of handling (e.g., by biodegradation), and relative non-toxicity compared to traditional inorganic semiconductors, virtually most current techniques for the synthesis, purification, and deposition of organic semiconductors require the use of toxic halogenated solvents. Compared with traditional chemical synthesis, the biosynthesis method provides special advantages; enzymes, used in biosynthesis, are generally operated in a "bio-friendly" environment-aqueous media, at room temperature, at neutral PH, and under atmospheric conditions. Generally, biosynthetic methods can obtain complex molecules from inexpensive and abundant materials.
Recently, research has found an efficient method for producing natural cyanine (indigo), i.e. by mimicking the mechanism of biosynthesis of organisms in heterologous host cells. Natural blue pigment was isolated from the plant pathogen Erwinia and other bacteria. It can be synthesized by polymerization of two units of L-glutamine, primarily by PPTase (4' -phosphotheinyl transferase) -activated non-ribosomal peptide synthetase (NRPS), such as IndC from Erwinia chrysanthemii or S.aureus (Streptomyces aureus) CCM3239, bpsA from Streptomyces lavendae. The natural blue pigment is a high-efficiency free radical scavenger, and a carbon-carbon double bond conjugated with a carbonyl group exists in the structure of the natural blue pigment, so that the plant pathogen can resist the oxidative stress of organic peroxide and superoxide during the plant defense reaction and has antibacterial activity.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide an application of natural blue pigment in an organic semiconductor device, which has a narrow band gap of 1.7eV, a very high molar extinction coefficient, an approximately planar structure, an energy level which allows the combination of hydrogen bonds in molecules and between molecules and has good adaptability, is a mark of high charge carrier mobility, and enables the natural blue pigment to have bipolar energy carrier characteristics.
The purpose of the invention is realized by adopting the following technical scheme:
the invention provides an application of natural blue pigment in an organic semiconductor device.
Further, the organic semiconductor device is an optical element or an electronic device, and the natural blue pigment is included in the optical element and the electronic device.
Further, the optical element is an organic field effect transistor.
Further, the organic field effect transistor includes a substrate, a gate electrode, a source electrode, a drain electrode, a dielectric layer, and a semiconductor layer, wherein the semiconductor layer includes a natural blue pigment.
Further, the dielectric layer is made of any one of silicon dioxide, polystyrene, polyvinyl alcohol, polymethyl methacrylate, poly-4-vinylphenol, benzocyclobutene and polyimide; the source electrode and the drain electrode are made of gold or tantalum; any one of silicon, aluminum, tungsten, indium tin oxide, gold and tantalum is doped in the grid; the substrate is made of one or more than two of glass, polyether sulfone, polycarbonate, polyethylene terephthalate (PET) and polyethylene naphthalate.
Further, the thickness of the dielectric layer is 15-1500 nm; the thickness of the source electrode and the thickness of the drain electrode are both 5-80 nm; the thickness of the grid electrode is 10-1500 nm.
Further, the thickness of the dielectric layer is 30-1000 nm; the thickness of the source electrode and the thickness of the drain electrode are both 10-30 nm; the thickness of the gate electrode is 30-60 nm.
Further, the preparation method of the semiconductor layer comprises the following steps: includes the steps of dissolving the natural blue pigment in a solution, and coating the solution on a substrate by spin coating or doctor blading to form a semiconductor layer.
Further, the thickness of the semiconductor layer is 10 to 300nm.
Further, the thickness of the semiconductor layer is 20-80 nm.
Compared with the prior art, the invention has the beneficial effects that:
the natural blue pigment of the organic semiconductor material provided by the invention has a semiconductor with a narrow band gap of 1.7eV, also has a very high molar extinction coefficient, is nearly of a planar structure, allows the combination of hydrogen bonds in molecules and among molecules and has a good energy level of adaptability, is a mark of high charge carrier mobility, has the characteristic of bipolar energy carriers, is a high-quality organic semiconductor material for the fields of complementary metal oxide semiconductor type circuits, sensors, light-emitting transistors and the like, and can be widely applied to the field of organic semiconductors.
Drawings
FIG. 1 is a structural formula of a natural blue pigment according to the present invention;
FIG. 2A is a UV-VIS spectrum of natural blue pigment in dimethyl sulfoxide solution at different concentrations according to the present invention;
FIG. 2B is a Tauc chart of natural blue pigment in dimethyl sulfoxide solution at different concentrations according to the present invention;
FIG. 3A is a UV-VIS spectrum of a natural blue pigment film;
FIG. 3B is an atomic force microscope image of a natural blue pigment film;
FIG. 4 is a cyclic voltammogram of natural blue pigment;
FIG. 5 is an absorption spectrum of a monomer and a triplet;
FIG. 6A is an output characteristic of an organic field effect transistor based on natural blue pigment;
FIG. 6B is an output characteristic of an organic field effect transistor based on natural blue pigment;
FIG. 6C is a transfer characteristic of a natural blue pigment based organic field effect transistor;
FIG. 6D is a graph of transfer characteristics of a natural blue pigment based organic field effect transistor;
FIG. 7A is a schematic structural diagram of an organic field effect transistor;
FIG. 7B is a schematic structural diagram of an organic field effect transistor;
FIG. 7C is a schematic diagram of an organic field effect transistor;
fig. 7D is a schematic structural view of the organic field effect transistor.
In the figure: 1. a substrate; 2. a gate electrode; 3. a source electrode; 4. a drain electrode; 5. a dielectric layer; 6. a semiconductor layer.
Detailed Description
The present invention will now be described in more detail with reference to the accompanying drawings, in which the description of the invention is given by way of illustration and not of limitation. The various embodiments may be combined with each other to form other embodiments not shown in the following description.
The invention provides an application of natural blue pigment in an organic semiconductor device. The natural blue pigment (indigo) of the present invention can be efficiently synthesized in Escherichia coli. In addition to its antioxidant and antibacterial activity, natural blue pigments have also made a seat in industrial environmentally friendly dyes due to their stability and deep blue color. In addition, it is also an organic semiconductor due to the molecular structural characteristics of natural blue pigment, similar to its corresponding conventional indigo dye. The band gap of the small molecule is extremely narrow due to the completely conjugated aromatic part and intermolecular hydrogen bonds in the natural blue pigment, and the organic semiconductor device using the natural blue pigment has excellent optical and electrical properties. This in turn leads to a tight molecular packing in its solid form, opening the way for its wide application in organic and bioelectronic technology, such as electrochemical and field effect transistors, organic solar cells, biosensors, etc.
According to an embodiment of the present invention, the organic semiconductor device is an optical element or an electronic device such as a transistor, a diode, an OLED, a sensor, a memory, a display, a battery, a resistor, a capacitor, an inductor, or the like. Natural blue pigments are included in optical elements and electronic devices. The optical element is an organic field effect transistor. The organic semiconductor is an organic field effect transistor, an optical element, an electroluminescent element and the like, and the natural blue pigment can be used for preparing a solution of the organic field effect transistor, the optical element and the electroluminescent element. The organic field effect transistor, the optical element, and the electroluminescent element each include a natural blue pigment. That is, the natural blue dye can be applied to the fields of organic field effect transistors, optical devices, electroluminescent devices, and solutions containing the natural blue dye for producing transistors, optical devices, electroluminescent devices, and the like.
Further, the organic field effect transistor includes a substrate 1, a gate electrode 2, a source electrode 3, a drain electrode 4, a dielectric layer 5, and a semiconductor layer 6, wherein the semiconductor layer is made of natural blue pigment. It should be understood that the organic field effect transistor may be a bottom gate organic field effect transistor, i.e., the gate is on the substrate, the semiconductor layer is on top, and the source/drain is in or above the semiconductor layer, as shown in fig. 7A and 7B; or a top gate organic field effect transistor, i.e. the gate is on top, the semiconductor layer is on the substrate and the source/drain electrodes are in the semiconductor layer, see fig. 7A to 7D.
Further, the material of the dielectric layer is any one of silicon dioxide, polystyrene, polyvinyl alcohol, polymethyl methacrylate, poly 4-vinylphenol, benzocyclobutene and polyimide; the source/drain is gold or tantalum; any one of silicon, aluminum, tungsten, indium tin oxide, gold and tantalum is doped in the grid; the substrate is made of one or more than two of glass, polyether sulfone, polycarbonate, polyethylene terephthalate (PET) and polyethylene naphthalate.
Further, the thickness of the dielectric layer is 15 to 1500nm, preferably 30 to 1000nm; the thickness of the source/drain is 5-80 nm, preferably 10-30 nm; the thickness of the gate electrode is 10 to 1500nm, preferably 30 to 60nm.
The preparation method of the semiconductor layer comprises the following steps: includes the steps of dissolving natural blue pigment in a solution, and coating the solution on a substrate by spin coating or doctor blading to form a semiconductor layer. The thickness of the semiconductor layer is 10 to 300nm. Preferably, the thickness of the semiconductor layer is 20 to 80nm.
In the present invention, natural blue pigment preparation reference is made to patent application No. CN201210416265.0 "Synthesis and extraction Process of blue Natural dye", specifically, an engineered strain capable of synthesizing natural blue pigment is grown in LB broth (10 g/L tryptone, 5g/L yeast extract and 10g/L sodium chloride) supplemented with 50. Mu.g/mL kanamycin at 37 ℃ with shaking at 250 rpm. After the culture reached an OD600 of 0.4 to 0.6, 200. Mu.M IPTG was added to induce the expression of Sc-IndC (indigo structure synthetase) and then produce natural cyanine. The induced broth was held at 18 ℃ and 250rpm for an additional 36 hours. The natural blue pigment was then harvested and purified as a dark blue powder. Continuously extracting the crude product with Soxhlet extractor at 100 deg.C for 72 hr to obtain light blue powder with yield of 85.9%, and the structural formula of natural blue pigment is shown in figure 1.
Example a elemental analysis:
the obtained product was subjected to hydrocarbon nitrogen sulfur element analysis using an element analyzer (EURO EA 3000), and the results were as follows:
element (%) Nitrogen is present in Carbon (C) Hydrogen
Specific gravity mean value 20,520 45,610 4,319
Theoretical mean value 22,565 48,394 3,249
Difference in specific gravity -2,042 -2,784 1,07
The thin films used in the present invention for determining optical measurements, cyclic Voltammetry (CV) measurements and characterization of Organic Field Effect Transistors (OFETs) are prepared using an organic evaporation system (Vaksis R)&D and Engineering) by physical vapor deposition, thereby achieving precise control of the thickness. The sublimation treatment is carried out at 230-250 deg.C and 10 deg.C -6 Support ceramic crucible (Al) under ultra-high vacuum condition 2 O 3 ) The process was carried out as follows. The crucible was preheated to 230 ℃ with a closed substrate shield to eliminate volatile impurities prior to deposition.
EXAMPLE two Spectroscopy detection
The material was analyzed by UV-visible spectroscopy and fluorescence spectroscopy to prepare 0.006mM, 0.02mM, 0.6mM and 0.9mM solutions of natural blue pigment in dimethyl sulfoxide, and the molar extinction coefficient was determined by the Beer-Lambert method.
The new material measures the absorbance of uv-visible light within a certain frequency range, thereby obtaining the basic data of its optical properties, as shown in fig. 2A. The change in the electronic energy can be determined by absorbance measurement as long as the organic compound is excited by ultraviolet or visible light. The optical gap is measured by a Tauc diagram, as shown in fig. 2B, and a linear absorption characteristic is observed by the energy distribution of monochromatic light. The natural blue pigment is a natural compound, so the optical absorption of the natural blue pigment is cut off at about 1.7eV under the optical gap reference.
To examine the optical properties of the natural blue pigment in the solid state, films were prepared by means of vacuum thermal evaporation on quartz glass plates to a thickness of 50. + -.10 nm (Dektak XT profilometer, bruker).
The absorption spectrum of the 50nm natural blue pigment thin film shows the characteristic spectral characteristics of the amorphous organic semiconductor. The low energy absorption maximum is located at 650nm, as in FIG. 3A. In order to study the thermal recrystallization property of the material, the film is annealed at 100 ℃ for 60min.
UV/visible absorption spectra were determined using a Lambda 1050UV/Vis/NIR spectrometer (Perkinelmer).
Example three atomic force microscope
The natural blue pigment was formed into smooth microcrystals of about 1.17nm by thermal vacuum evaporation and subjected to morphological observation by atomic force microscopy, as shown in fig. 3B.
Example four Cyclic voltammetry
To determine the energy transition level of the natural blue pigment, we performed thin film cyclic voltammetry tests on indium tin oxide coated glass plates. The 100nm film of the indium tin oxide coating is used as a working electrode, the silver/silver chloride electrode is used as a reference electrode, and the platinum plate electrode is used as an auxiliary electrode. The electrolyte is 0.1M tetrabutylammonium hexafluorophosphate solution prepared from acetonitrile. The forward/reverse current was repeatedly measured until a steady current was established.
E HOMO ＝-(4.75+E ox onset vs.Fc/Fc+ )eV
E LUMO ＝-(4.75+E red onset vs.Fc/Fc+ )eV
Ferrocenium salt (Fc/Fc +) organic redox couple was used as external quasi-reference electrode. E ox onset vs.Fc/Fc The initial potential of an oxidation peak when a ferrocenium salt (Fc/Fc +) organic redox couple is used as an external quasi-reference electrode; e red onset vs.Fc/Fc The initial potential of a reduction peak when a ferrocenium salt (Fc/Fc +) organic redox couple is used as an external quasi-reference electrode; compared with a common hydrogen electrode, the obtained electrochemical potential is-4.75 eV, and the oxidation-reduction potential of the ferrocenium salt is 0.69V.
When the cyclic voltammetry test is at the peak of-1137 mV, the material is in an oxidation process, i.e., the energy of one electron is taken from the high energy orbit of the molecule. Accordingly, in the reduction stage, the low energy orbital needs to extract an electron energy from the molecule, which can be observed at the peak of 483mV, as shown in FIG. 4. Through cyclic voltammetry, the energy of the high-energy orbit of the natural blue pigment is calculated to be-5.23 eV, the energy of the low-energy orbit is calculated to be-3.61 eV, and the capacitance voltage between bands is 1.62eV.
Unlike organic dyes such as Diketopyridopyridines (DPP), benzophenones, divinylketones, indigoids, etc., natural blue pigments are not cross-conjugated but are fully conjugated with single and double bonds alternating along successive atoms. Such structural properties bring about low energy gaps that are rare in small molecule structures.
In DMSO solutions, the two conjugated rings are connected at a double-sided rotation angle of 1.2 ° and the geometric distribution is nearly coplanar. The two quaternary carbons form a subunit bridge, with a bond length of 1.38. In the molecule, hydrogen bonds are formed between oxygen atoms of carbonyl groups and tertiary carbons beside the subunit groups, so that 0.2qe of additional electric energy is formed. The molecules of the natural blue pigment triplet form 35.5 degrees of rotation, so that double bond bridges are formed by conjugation among the quaternary carbons, the Weber index value of the double bond bridges is 1.07, and the hydrogen bond energy between the biplanars is reduced along with the Weber index value of 0.006.
The natural blue pigment of the triplet has similarity with indigo. Geometric optimization of the triad indicates that the dihedral angle between the two aromatic rings is significantly greater than: the former is 35.5 deg. and the latter is 1.2 deg.. But the energy difference between the two is only 0.49eV, which indicates that the excited state is higher in energy than the triplet, and that photoexcitation can induce a "forbidden transition" between the triplet of the excited state and the ground state to form a "radiationless transition" within the relaxation time.
According to time-dependent density functional theory (TD-DFT), the absorption spectrum of the molecule was calculated by a slight excitation at 592nm, and excitation was carried out with 390nm for the triplet molecule, as shown in FIG. 5.
Monomer Triplet body
HOMO,eV 5.32 4.62
LUMO,eV 3.55 0.89
αrot,° 1.2 35.5
B.O.C-C 1.38 1.07
B.O.O-H 0.020 0.006
Q Mulliken ,qe +0.2 +0.18
γ max ,nm 592 390
Wherein alpha is rot The dihedral angle between two aromatic rings, B.O.C-C is the Weber index (natural bond sequence) of the double bond bridge formed by conjugation between the quaternary carbons (Wiberg index) between the two quaternary carbons, and B.O.O.H is the Weber index (Wiberg index) between O and H, Q Mulliken Is a Mariken charge, gamma max The maximum absorption value.
As shown in FIGS. 6A to 6D, an electron field mobility of about 1X 10 can be observed -7 cm 2 the/Vs and hole field migration effect are about 1 × 10 -8 cm 2 Bipolar behavior of/Vs. Aromatic heterocycles in natural blue pigment (indigo) molecules have stronger electrophilic effect, enhance the conjugation effect and form pi-pi superposition. This makes it possible to stabilize its bipolar ability as long as the natural blue pigment (indigo) remains in a solid state when high-low energy orbital electron transition occurs between adjacent molecules after the semiconductor thin film is formed.
Natural blue pigment (indigo) is a semiconductor with a narrow bandgap of 1.7eV, has a high molar extinction coefficient, a nearly planar structure, allows for the incorporation of intramolecular and intermolecular hydrogen bonds, and a well-adapted energy level. These properties of the molecular structure, which may be indicative of a high charge carrier mobility, may allow for the use of natural blue pigments in OFET (Organic field-effect transistors) devices or solar cells.
In addition, the molecule also has functional groups such as carboxyl, amino and the like, so that a path is opened for the application of the molecule in the fields of super capacitor devices and batteries (compounds containing carbonyl, carboxyl or quinonyl are proved to be bionic energy storage electrode materials), or amino acute carbon dioxide capture is utilized.
In the present invention, a biosynthetic organic semiconductor material, natural cyanine (indigo), was tested, in particular its optical and electrical characteristics. The organic dye capable of being biosynthesized with high efficiency has high molar extinction coefficient and also has a plurality of advantages as an organic semiconductor material. The optical band gap of the organic thin film transistor is about 1.7eV, the organic thin film transistor is of a nearly planar structure, and the hydrogen bonds in molecules and among molecules enable the organic thin film transistor to have the characteristic of a bipolar energy carrier serving as organic thin film transistor equipment, so that the organic thin film transistor is a high-quality organic semiconductor material in the fields of complementary metal oxide semiconductor type circuits, sensors, light-emitting transistors and the like. Namely, the OFET semiconductor material has the following characteristics: the Lowest Unoccupied Molecular Orbital (LUMO) or Highest Occupied Molecular Orbital (HOMO) energy level of a single molecule facilitates electron or hole injection; the solid crystal structure should provide sufficient molecular orbital overlap to ensure that charge does not have excessive energy barriers when migrating between adjacent molecules; the size range of the semiconductor single crystal continuously spans two contact points of a source contact and a drain contact, and the orientation of the single crystal is parallel to the direction of high mobility and the direction of current; has low intrinsic conductivity, reduces off-state leakage current, and improves the on/off ratio of the device current. The organic semiconductor device using the natural blue pigment has excellent optical and electrical characteristics.
The above embodiments are only preferred embodiments of the present invention, and the protection scope of the present invention is not limited thereby, and any insubstantial changes and substitutions made by those skilled in the art based on the present invention are within the protection scope of the present invention.

Claims (7)

1. The application of the natural blue pigment in the organic semiconductor device is characterized in that the organic semiconductor device is an organic field effect transistor, the organic field effect transistor comprises a substrate, a grid electrode, a source electrode, a drain electrode, a dielectric layer and a semiconductor layer, wherein the semiconductor layer contains the natural blue pigment.
2. The use of the natural blue pigment according to claim 1 in an organic semiconductor device, wherein the material of the dielectric layer is any one of silicon dioxide, polystyrene, polyvinyl alcohol, polymethyl methacrylate, poly 4-vinylphenol, benzocyclobutene, polyimide; the source electrode and the drain electrode are made of gold or tantalum; any one of silicon, aluminum, tungsten, indium tin oxide, gold and tantalum is doped in the grid; the substrate is made of one or more than two of glass, polyether sulfone, polycarbonate, polyethylene terephthalate (PET) and polyethylene naphthalate.
3. The use of the natural blue pigment according to claim 1 in an organic semiconductor device, wherein the dielectric layer has a thickness of 15 to 1500nm; the thickness of the source electrode and the thickness of the drain electrode are both 5-80 nm; the thickness of the grid electrode is 10-1500 nm.
4. The use of the natural blue pigment according to claim 3 in an organic semiconductor device, wherein the thickness of the dielectric layer is 30 to 1000nm; the thickness of the source electrode and the thickness of the drain electrode are both 10-30 nm; the thickness of the gate electrode is 30-60 nm.
5. The use of the natural blue pigment according to claim 1 in an organic semiconductor device, wherein the semiconductor layer is prepared by a method comprising: includes the steps of dissolving a natural blue pigment in a solvent to form a solution, and coating the solution on a substrate by spin coating or doctor blading to form a semiconductor layer.
6. The use of the natural blue pigment according to claim 5, wherein the thickness of said semiconductor layer is 10 to 300nm.
7. The use of the natural blue pigment according to claim 6 in an organic semiconductor device, wherein the thickness of the semiconductor layer is 20 to 80nm.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008062181A (en) * 2006-09-07 2008-03-21 Gifu Univ Method for manufacturing porous zinc oxide electrode and dye-sensitized solar cell
CN102082229A (en) * 2010-11-19 2011-06-01 无锡中科光远生物材料有限公司 Organic field effect tube and preparation method thereof
CN104576931A (en) * 2015-01-12 2015-04-29 华南理工大学 Organic/polymer solar battery device and preparation method thereof
CN108894014A (en) * 2018-04-17 2018-11-27 德清亿玛生物科技有限公司 The method that natural blue pigment Indigoidine after colorant match dyes protein fibre fabric

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008062181A (en) * 2006-09-07 2008-03-21 Gifu Univ Method for manufacturing porous zinc oxide electrode and dye-sensitized solar cell
CN102082229A (en) * 2010-11-19 2011-06-01 无锡中科光远生物材料有限公司 Organic field effect tube and preparation method thereof
CN104576931A (en) * 2015-01-12 2015-04-29 华南理工大学 Organic/polymer solar battery device and preparation method thereof
CN108894014A (en) * 2018-04-17 2018-11-27 德清亿玛生物科技有限公司 The method that natural blue pigment Indigoidine after colorant match dyes protein fibre fabric

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