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WO2015046004A1 - Luminophore infrarouge - Google Patents

Luminophore infrarouge Download PDF

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Publication number
WO2015046004A1
WO2015046004A1 PCT/JP2014/074655 JP2014074655W WO2015046004A1 WO 2015046004 A1 WO2015046004 A1 WO 2015046004A1 JP 2014074655 W JP2014074655 W JP 2014074655W WO 2015046004 A1 WO2015046004 A1 WO 2015046004A1
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WO
WIPO (PCT)
Prior art keywords
titanium oxide
infrared
infrared phosphor
phosphor
group
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Ceased
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PCT/JP2014/074655
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English (en)
Japanese (ja)
Inventor
幸平 増田
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Shin Etsu Chemical Co Ltd
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Shin Etsu Chemical Co Ltd
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Priority to JP2015539147A priority Critical patent/JPWO2015046004A1/ja
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Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/67—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing refractory metals
    • C09K11/671—Chalcogenides
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F19/00—Integrated devices, or assemblies of multiple devices, comprising at least one photovoltaic cell covered by group H10F10/00, e.g. photovoltaic modules
    • H10F19/80—Encapsulations or containers for integrated devices, or assemblies of multiple devices, having photovoltaic cells
    • H10F19/85—Protective back sheets
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F77/00—Constructional details of devices covered by this subclass
    • H10F77/40—Optical elements or arrangements
    • H10F77/42—Optical elements or arrangements directly associated or integrated with photovoltaic cells, e.g. light-reflecting means or light-concentrating means
    • H10F77/45—Wavelength conversion means, e.g. by using luminescent material, fluorescent concentrators or up-conversion arrangements
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10H—INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
    • H10H20/00—Individual inorganic light-emitting semiconductor devices having potential barriers, e.g. light-emitting diodes [LED]
    • H10H20/80—Constructional details
    • H10H20/85—Packages
    • H10H20/851—Wavelength conversion means
    • H10H20/8511—Wavelength conversion means characterised by their material, e.g. binder
    • H10H20/8512—Wavelength conversion materials
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/52—PV systems with concentrators

Definitions

  • the present invention relates to an infrared phosphor made of titanium oxide and the use of titanium oxide as an infrared phosphor. More specifically, it is a method of using titanium oxide, which is preferably surface-treated with a silicon compound having affinity for other objects, as an infrared phosphor, and used as a wavelength conversion material, a radiation heat dissipation material, and a biological imaging material. It relates to a possible infrared phosphor.
  • Infrared fluorescence refers to the property of emitting infrared light when absorbing light in the ultraviolet-visible region. Many phosphors whose emission region is in the ultraviolet-visible region have been known so far, but only a limited example of phosphors whose emission region is in the infrared region is known. Infrared rays have excellent permeability to living tissue and can be used as fluorescent probes. Although they can be used for biological research, medical research, diagnosis, etc., the development of infrared fluorescent materials has been delayed. .
  • Patent Document 1 discloses an infrared phosphor mainly composed of organic molecules.
  • An infrared phosphor mainly composed of organic molecules is characterized by a small Stokes shift (wavelength difference between excitation light and light emission) of about 20 to 30 nm.
  • a small Stokes shift is disadvantageous in that an image with a clear signal / noise ratio is obtained.
  • a technique for reducing the line width by using a double grating or the like has been developed. Has been hindered.
  • Infrared phosphors mainly composed of organic molecules are often unstable to heat and light because organic molecules having a long conjugated system are often used. Such characteristics have made the infrared phosphors expensive and special and have not only prevented simple use but also have become a serious defect that limits the targets of biological research. For example, it is possible to detect thermophilic bacteria that produce thermostable DNA polymerase (Non-patent Document 1: Science, 1988, 239, 487-491), which is also applied to the polymerase chain reaction, with an infrared fluorescent probe. However, it is still difficult with a probe using a conventional infrared phosphor. However, it is considered that a long conjugated system is indispensable for emitting infrared fluorescence, and no improvement method for this wrinkle has been proposed.
  • An object of the present invention is to provide an infrared phosphor having a large Stokes shift, excellent in thermal stability, and having affinity with other objects, and a method for using the same.
  • the present inventor has found that it is effective to use titanium oxide as the infrared phosphor.
  • the present invention provides the following infrared phosphor and a method for using the same.
  • Infrared phosphor made of titanium oxide.
  • R 1 p R 2 q R 3 r Si (OR 4 ) 4-pqr (1) In the formula, R 1 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 2 , R 3 and R 4 each independently represents an alkyl group having 1 to 6 carbon atoms.
  • an infrared phosphor having a large Stokes shift, excellent thermal stability, and affinity with other objects can be obtained.
  • an infrared phosphor comprising the titanium oxide of the present invention and a method for using the titanium oxide as an infrared phosphor will be described in detail.
  • Titanium oxide may be any polymorph of anatase type, rutile type or brookite type.
  • the anatase type and the rutile type are preferable because they can be easily prepared as a fine particle dispersion.
  • the size of the titanium oxide particles is not limited.
  • when it is intended for applications such as imaging materials it is preferably transparent in the visible region.
  • the volume average 50% cumulative particle size measured by the dynamic light scattering method is preferably 1 nm to 100 nm. If it is smaller than 1 nm, it may be difficult to handle as a colloidal solution. When it is larger than 100 nm, the influence of scattering may be increased in the visible region.
  • Titanium oxide may be used in any form of solid or dispersion.
  • a dispersion is preferable because of its excellent dispersibility in tissues.
  • solids can also be used when intended for use as a general infrared phosphor.
  • the dispersion medium when titanium oxide is used as a dispersion those generally used as a solvent such as water, methanol, ethanol, isopropyl alcohol, hydrocarbon, BTX component, etc. can be used.
  • a dispersion medium such as water or ethanol having excellent biocompatibility is preferable.
  • hydrocarbons and BTX components can also be used for applications as imaging materials for industrial tests and wavelength conversion materials.
  • Such titanium oxide may be synthesized using titanium alkoxide or peroxotitanium as a precursor, or a commercially available product may be used.
  • covered the surface of titanium oxide with other metal oxides, such as a zirconia, an alumina, a silica can be used.
  • Examples of the commercially available titanium oxide that can be used in the present invention include Optolake (manufactured by JGC Catalysts and Chemicals, product number “1130Z”) and the like.
  • Infrared fluorescence in the present invention is directed to those having an emission wavelength of 700 nm to 1,200 nm, preferably 750 nm to 1,200 nm, more preferably 800 nm to 1,200 nm. If the emission wavelength is smaller than 700 nm, it becomes a phosphor in the visible region and is not a subject of the present invention. If the emission wavelength is larger than 1,200 nm, it may be used for excitation of the rotational level or vibration level of the molecule, and the biological transparency may not be sufficient.
  • the excitation wavelength in the present invention is 300 nm to 400 nm, preferably 310 nm to 390 nm, and more preferably 320 nm to 380 nm. If the excitation wavelength is less than 300 nm, the ultraviolet light may damage the sample when used as a biological imaging material. If it is larger than 400 nm, unintentional excitation may always occur when used in a bright room.
  • the difference between the emission wavelength and the excitation wavelength is called Stokes shift.
  • the Stokes shift in the method of the present invention is 300 nm to 900 nm, preferably 400 nm to 900 nm, more preferably 500 nm to 900 nm.
  • the infrared phosphors known so far are characterized by a small Stokes shift of about 20 to 30 nm.
  • the excitation light is close to the light emitting region, and the excitation light is mixed in the observation system, which causes a decrease in the ratio due to an increase in the signal / noise ratio.
  • a technique for reducing the half width of a signal by a double grating method using two or more diffraction gratings is known, but there is a drawback that the apparatus becomes complicated.
  • a special light source such as an infrared LED is often required as a light source used for excitation.
  • the Stokes shift of the infrared phosphor may generally be larger than 900 nm as long as it has an appropriate functional structure.
  • Excitation does not have to be performed simultaneously with light emission, and an infrared phosphor previously excited by ultraviolet rays may be introduced into a living body and a delayed fluorescence may be observed.
  • the delay time of delayed fluorescence is preferably 1 minute or longer, more preferably 5 minutes or longer, and even more preferably 10 minutes or longer. If the delay time is shorter than 1 minute, it will be extinguished by the introduction and observation may be difficult.
  • the infrared phosphor in the present invention is preferably surface-treated with a silicon compound represented by the following general formula (1).
  • a silicon compound represented by the following general formula (1) when it is intended to be used as an imaging material, it is preferably treated with a silicon compound having an affinity for other objects.
  • the surface treatment is not necessarily performed with a silicon compound.
  • R 1 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms
  • R 2 , R 3 and R 4 each independently represents an alkyl group having 1 to 6 carbon atoms.
  • P is an integer of 1 to 3
  • q is 0, 1 or 2
  • r is 0, 1 or 2
  • p + q + r is an integer of 1 to 3.
  • R 1 include a hydrogen atom, an unsubstituted monovalent hydrocarbon group such as an alkyl group having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, an alkenyl group, an aryl group, and an aralkyl group, and the monovalent hydrocarbon group.
  • an unsubstituted monovalent hydrocarbon group such as an alkyl group having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, an alkenyl group, an aryl group, and an aralkyl group, and the monovalent hydrocarbon group.
  • Groups especially one or more of the hydrogen atoms of the alkyl group, epoxy groups such as (meth) acryloxy groups, glycidoxy groups, epoxycyclohexyl groups, halogen atoms such as chloro groups, fluoro groups, mercapto groups, thiol groups, sulfide groups And a substituted monovalent hydrocarbon group substituted with an amino-containing group such as an amino group and an aminoethylamino group, a carboxyl group, an oxiranyl group, an isocyanate group, and an isocyanurate group.
  • epoxy groups such as (meth) acryloxy groups, glycidoxy groups, epoxycyclohexyl groups, halogen atoms such as chloro groups, fluoro groups, mercapto groups, thiol groups, sulfide groups
  • a substituted monovalent hydrocarbon group substituted with an amino-containing group such as an amino group and an aminoethylamino group, a carboxyl
  • the amount of silicon compound used relative to the infrared phosphor is 0 to 10% by mass, preferably 0 to 8% by mass, and more preferably 0 to 5% by mass.
  • 0.5 mass% or more, especially 1 mass% or more are preferable.
  • the amount of the silicon compound used is more than 10% by mass, a free silicon oligomer that has not been subjected to the surface treatment may be easily formed, which is not preferable. Free silicon oligomers that have not been subjected to surface treatment are preferably removed by ultrafiltration.
  • the infrared of the present invention is particularly suited for applications as bioimaging materials. It may act on the subject competitively with the phosphor, forming a background and causing a decrease in the effective signal.
  • the silicon compound represented by the general formula (1) has a reactive site that becomes a factor indicating affinity with other objects.
  • the reaction site may be an electrophilic group or a nucleophilic group.
  • Electrophilic groups easily react with nucleobases constituting deoxyribonucleic acid and ribonucleic acid, and can be used effectively as a linker.
  • Nucleobase as used herein refers to adenine, thymine, cytosine, guanine, and uracil sites.
  • Electrophilic groups can also be suitably used as linkers because they can be subjected to nucleophilic attack from the N-terminus of amino acids and peptides, hydroxyl groups of sugars, and the like.
  • electrophilic group examples include oxiranyl group, vinyl group, acrylic group, carboxyl group, and chloro group.
  • Nucleophilic groups can act with amino acids and the C-terminus of peptides, electrophilic sites of enzymes, and the like. Moreover, since it can act also as a metal porphyrin or a ligand of a zerovalent metal colloid, it can be used suitably as a linker. Examples of the nucleophilic group that can be used for such purposes include amino groups, thiol groups, and sulfide groups.
  • Examples of other objects to which the silicon compound can exhibit affinity include biomaterial compounds and chemical bonds or functional groups contained in the biomaterial compounds. Specifically, adenine, thymine, cytosine, guanine, uracil, and nucleobases of these methylated derivatives, glucose, ribose, deoxyribose, galactose, saccharides such as allose, talose, gulose, altrose, mannose, idose, Amino acids and amino acid derivatives such as alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, porphyrin and A metal porphyrin etc. can be mentioned.
  • the method of surface-treating the above-mentioned titanium oxide with an organosilicon compound of formula (1) or a partially hydrolyzed condensate thereof comprises reacting water, titanium oxide and the compound of formula (1) in the presence of an acid and a base catalyst.
  • an acid catalyst include monovalent carboxylic acids such as formic acid, acetic acid, propionic acid and benzoic acid, divalent carboxylic acids such as oxalic acid, malonic acid, glutaric acid, adipic acid and pimelic acid, methanesulfonic acid and p-toluenesulfone.
  • Examples thereof include organic acids such as acids, mineral acids such as hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid and boric acid, and cation exchange resins.
  • As the base catalyst sodium hydroxide, lithium hydroxide, barium hydroxide, alkali (earth) metal hydroxide such as calcium hydroxide, ammonia, ammonia derivatives such as tetramethylammonium hydroxide, tetrabutylammonium hydroxide, Examples thereof include nitrogen-containing organic compounds such as trimethylamine, triethylamine, pyridine, pyrazine and urea.
  • the acid and base catalyst can be used in an amount of 0.01 to 10% by mass, preferably 0.1 to 5% by mass, based on the organosilicon compound of the formula (1).
  • Water can use more than the stoichiometric amount necessary for the organosilicon compound of formula (1) to be completely hydrolyzed.
  • the reaction can be carried out at 10 to 200 ° C, preferably 20 to 100 ° C.
  • a heat medium using conductive heat transfer such as an oil bath or radiant heat transfer such as microwaves can be used.
  • the infrared phosphor in the present invention is characterized by having a large Stokes shift and thermal stability, and further having affinity with other objects.
  • a site having affinity with another target may be used while having an electrophilic group or a nucleophilic group in the hope of being chemically modified in vivo.
  • it may be used after reacting with a sugar chain, a peptide, a nucleobase, and a derivative thereof in advance.
  • Example 1 Ion-exchanged water (100 g), ammonium nitrate (0.01 g), ion-exchange resin (manufactured by Organo Corporation, trade name “Amberlite 200CT (H) -AG”, 10 g), titanium oxide dispersion (manufactured by JGC Catalysts & Chemicals Co., Ltd.) , Trade name “OPTRAIK 1130Z”, non-volatile content 30% by mass, 100 g), 3-glycidoxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name “KBM-403”, 1 g), 3-glycid Xylpropylmethyldiethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name “KBE-402”, 0.5 g) was added and stirred at room temperature for 2 hours.
  • the ion exchange resin was removed by filtration, and the obtained dispersion was filtered with an ultrafilter (manufactured by Andritz) while adding ethanol, and the non-volatile content concentration in the filtration residue was adjusted to 10% by mass. It was confirmed by gel permeation chromatography (manufactured by Tosoh Corporation, product name “HLC-8320”, polystyrene-packed column “TSKgel G3000HXL”, using eluent THF) that the filtration residue did not contain a free oligomer of silicon compound. .
  • the obtained dispersion liquid was measured for infrared fluorescence using a spectroscope (manufactured by Horiba, product name “FluoroLog3”, detector InGaAs array).
  • the measurement results are shown in FIG. FIG. 1 is an emission spectrum when the dispersion was excited at 370 nm, and it was revealed that it had a peak top near 840 nm. Although it became clear from FIG. 1 that the continuous emission spectrum was shown, it was suggested that it was based on a clear band structure.
  • titanium oxide has never been observed. As shown in Example 1, it was found that characteristic infrared fluorescence characteristics were exhibited, and it was revealed that titanium oxide can be used as an infrared phosphor. The usefulness of titanium oxide as an infrared phosphor has never been mentioned so far.
  • the infrared phosphor provided by the present invention has a large Stokes shift, a clear image can be easily provided when used as a biological imaging material.
  • a near-infrared filter blocking most of the ultraviolet-visible light and blocking near-infrared light
  • An image having a large contrast can be obtained simply by attaching a filter that transmits light.
  • Such simple infrared fluorescence observation is difficult when a conventional infrared phosphor having a small Stokes shift is used.
  • the excitation does not need to be performed simultaneously with the light emission, and a method may be employed in which delayed fluorescent light is observed by introducing a previously excited infrared phosphor into the living body.
  • the infrared phosphor provided by the present invention has applicability as a heat dissipation material for light-emitting elements such as LEDs and organic ELs. Conventionally, energy relaxation when absorbing ultraviolet light is often compensated in the form of vibrational level enhancement, in which case thermal fatigue accumulates in the sealing resin, causing cracks and yellowing. It was.
  • the infrared phosphor of the present invention can be used for the purpose of removing such unnecessary ultraviolet energy by radiant heat radiation.
  • the infrared phosphor provided by the present invention has the potential to be used as a filler for solar cell backsheets. Excitation and emission may be reversible, and infrared phosphors may emit ultraviolet light when two-photon absorption occurs in the infrared region. By utilizing this characteristic, it is possible to reuse infrared light transmitted without being absorbed by the solar cell as ultraviolet light.

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  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Luminescent Compositions (AREA)
  • Led Device Packages (AREA)
  • Photovoltaic Devices (AREA)

Abstract

La présente invention concerne un luminophore infrarouge comprenant de l'oxyde de titane. Selon la présente invention, il est possible de produire un luminophore infrarouge ayant un déplacement de Stokes important, une excellente stabilité thermique et une affinité pour d'autres matériaux d'intérêt.
PCT/JP2014/074655 2013-09-25 2014-09-18 Luminophore infrarouge Ceased WO2015046004A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2015539147A JPWO2015046004A1 (ja) 2013-09-25 2014-09-18 赤外蛍光体

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JP2013-197969 2013-09-25
JP2013197969 2013-09-25

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WO2015046004A1 true WO2015046004A1 (fr) 2015-04-02

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018536993A (ja) * 2015-11-25 2018-12-13 エージーシー グラス ユーロップＡｇｃ Ｇｌａｓｓ Ｅｕｒｏｐｅ 光起電力デバイス
WO2019035160A1 (fr) 2017-08-14 2019-02-21 日産自動車株式会社 Corps mobile comportant une couche de régulation de reflet

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018536993A (ja) * 2015-11-25 2018-12-13 エージーシー グラス ユーロップＡｇｃ Ｇｌａｓｓ Ｅｕｒｏｐｅ 光起電力デバイス
WO2019035160A1 (fr) 2017-08-14 2019-02-21 日産自動車株式会社 Corps mobile comportant une couche de régulation de reflet
US20200194605A1 (en) * 2017-08-14 2020-06-18 Nissan Motor Co., Ltd. Mobile body having reflection control layer
US11011659B2 (en) 2017-08-14 2021-05-18 Nissan Motor Co., Ltd. Mobile body having reflection control layer

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