WO2015115556A1 - イオン液体を含む光波長変換要素およびその光波長変換要素を含む物品 - Google Patents
イオン液体を含む光波長変換要素およびその光波長変換要素を含む物品 Download PDFInfo
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Images
Classifications
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/355—Non-linear optics characterised by the materials used
- G02F1/361—Organic materials
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0282—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aliphatic ring, e.g. morpholinium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/39—Photocatalytic properties
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/353—Frequency conversion, i.e. wherein a light beam is generated with frequency components different from those of the incident light beams
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/122—Ionic conductors
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/02—Details
- H01L31/0216—Coatings
- H01L31/02161—Coatings for devices characterised by at least one potential jump barrier or surface barrier
- H01L31/02162—Coatings for devices characterised by at least one potential jump barrier or surface barrier for filtering or shielding light, e.g. multicolour filters for photodetectors
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/054—Optical elements directly associated or integrated with the PV cell, e.g. light-reflecting means or light-concentrating means
- H01L31/055—Optical elements directly associated or integrated with the PV cell, e.g. light-reflecting means or light-concentrating means where light is absorbed and re-emitted at a different wavelength by the optical element directly associated or integrated with the PV cell, e.g. by using luminescent material, fluorescent concentrators or up-conversion arrangements
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- 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 a light wavelength conversion element containing an ionic liquid and an article (a solar cell, a photocatalyst, a photocatalytic hydrogen / oxygen generator, and a light upconversion filter) including the light wavelength conversion element.
- Light-secondary energy conversion elements elements that convert light into secondary energy
- solar cells with high light-secondary energy conversion efficiency high light-secondary energy conversion efficiency
- hydrogen-generating photocatalysts Is growing.
- Light-secondary energy conversion elements such as general solar cells and hydrogen-generating photocatalysts have a certain threshold wavelength that is unique to the light-secondary energy conversion element among light in a wide wavelength range included in sunlight. Only short wavelength components are used for conversion, and components longer than the threshold wavelength are unused. Therefore, as one of the technologies for effectively using light in a wide wavelength range included in sunlight, light up-conversion (that is, light by absorbing light of a long wavelength and emitting light of a shorter wavelength) Are being studied.
- Patent Document 1 discloses a composition for up-converting photon energy, a first component that functions as a photoreceptor such as at least phthalocyanine, metal porphyrin, metal phthalocyanine, and absorbs energy in a first wavelength region, and polyfluorene. , Oligofluorenes and copolymers thereof, and a second component that functions as a light emitter such as polyparaphenylene and emits energy in a second wavelength region.
- a photoreceptor such as at least phthalocyanine, metal porphyrin, metal phthalocyanine
- a second component that functions as a light emitter such as polyparaphenylene and emits energy in a second wavelength region.
- Non-Patent Document 1 describes an optical up-converter using relatively weak light such as sunlight in a toluene solvent using a triplet-triplet annihilation process (hereinafter referred to as “TTA process”) in an organic molecule.
- TTA process triplet-triplet annihilation process
- Non-patent Documents 2 and 3 There are also precedents using high molecular weight organic polymers as the medium of organic molecules contained in the optical upconverter.
- Patent Document 2 discloses a triplet energy of the sensitizer in a system including at least one polymer for light upconversion and at least one sensitizer containing at least one heavy atom. Systems are described where the level is higher than the triplet energy level of the polymer.
- Non-Patent Document 2 describes an optical upconverter using a polymer of cellulose acetate (molecular weight: about 100,000) as a dispersion medium of organic molecules.
- Non-Patent Document 3 describes an optical up-converter using a soft rubber-like polymer as a medium at room temperature where the glass transition temperature (Tg) is 236 K (minus 37 ° C.).
- Non-Patent Document 4 describes an optical upconverter using a styrene oligomer (a mixture of styrene trimer and styrene tetramer) as a medium for organic photosensitizer molecules and organic light emitting molecules.
- a styrene oligomer a mixture of styrene trimer and styrene tetramer
- Non-Patent Document 5 describes metalloporphyrins as organic photosensitizing molecules that can be used for light upconversion using the TTA process, and diphenylanthracene, 9,10-bis (phenylethynyl) as organic light emitting molecules. ) Anthracene and 9,10-bis (phenylethynyl) naphthacene are described, and toluene is described as a medium for organic photosensitizer and organic light emitting molecules.
- Non-Patent Document 6 discloses that boron dipyrromethene (BODIPY) derivative is used as a sensitizer for photoupconversion using TTA process, and perylene or 1-chloro-9,10-bis (phenylethynyl) anthracene is used as a medium. It is described that toluene is used.
- BODIPY boron dipyrromethene
- Non-Patent Document 7 describes light upconversion using biacetyl as a sensitizer, 2,5-diphenyloxazole (hereinafter referred to as “PPO”) as a luminescent molecule, and benzene as a medium.
- PPO 2,5-diphenyloxazole
- Non-Patent Document 8 describes light up-conversion of a polymethyl methacrylate film using 2-methoxythioxanthone as a sensitizer and PPO as a light emitting molecule.
- Non-patent Document 1 In optical upconverters using the TTA process, in principle, it is necessary for organic molecules to exchange energy in a medium in order to exchange energy, so that most prior art (Non-patent Document 1) is required.
- a volatile organic solvent such as toluene or benzene or a highly volatile medium such as styrene oligomer was used as the medium.
- highly volatile media such as volatile organic solvents and styrene oligomers have a safety problem due to their flammability, and lightly absorb resin materials that dissolve in the media or swell due to penetration of the media. The problem is that it cannot be used as a container for wavelength conversion elements.
- optical up-converter using a TTA process using a polymer compound such as cellulose acetate and flexible rubber as a medium
- the polymer compound is combustible.
- it since it is solid at room temperature (300K) and has low fluidity, there has been a problem that the intensity of the up-converted light is significantly reduced at room temperature (300K) and below.
- Non-Patent Document 3 optical up-conversion due to the TTA process is caused by the fact that organic molecules responsible for triplet excitation energy inside the medium need to exchange energy between organic molecules through diffusion motion and mutual collision.
- the upconversion emission intensity increases, but in the temperature range where the temperature is low and the fluidity of the medium is poor ( ⁇ 300K), the upconversion emission intensity. Is described to be very weak.
- the present inventors have proposed a light wavelength conversion element in which an organic photosensitizer molecule and an organic light emitting molecule are dissolved and / or dispersed in an ionic liquid in light upconversion using a TTA process.
- a decrease in upconversion light intensity due to high viscosity of the medium, flammability of the medium, and volatility of the medium are solved (Patent Document 3).
- Non-Patent Documents 7 and 8 describe optical up-conversion in which light having a wavelength in the visible region is converted into light having an ultraviolet wavelength in the vicinity of 350 to 440 nm, which is close to the visible region, but emits light at a wavelength of 360 nm or less. There is no prior art for converting the light into the wavelength of the ultraviolet region having the maximum wavelength.
- the present invention has been made in view of the above-mentioned problems, and its purpose is to have high light wavelength conversion efficiency applicable to light as weak as the intensity of sunlight and to have good temporal stability, and therefore, the sun.
- Light with a shorter wavelength for example, light with a wavelength in the ultraviolet region
- an article solar cell, photocatalyst, photocatalytic hydrogen / oxygen generator, and light up-conversion filter including the light wavelength conversion element.
- the light wavelength conversion element of the present invention comprises an organic photosensitizer molecule (A) and an organic light emitting molecule (B), which are a combination showing a triplet-triplet annihilation process, in an ionic liquid.
- A organic photosensitizer molecule
- B organic light emitting molecule
- C a light wavelength conversion element that is dissolved and / or dispersed in the eye and is visually homogeneous and transparent, and has an absorption maximum wavelength (however, a plurality of absorption maximum wavelengths of the organic photosensitizer molecule (A)). If present, the longest absorption maximum wavelength among them is characterized by being in the range of 250 to 499 nm.
- the organic photosensitizing molecule having an absorption maximum wavelength (however, when there are a plurality of absorption maximum wavelengths, the longest absorption maximum wavelength among them) is in the range of 250 to 499 nm. Since (A) is used, light having a wavelength of 250 to 499 nm in the ultraviolet to visible range can be converted into light having a shorter wavelength (for example, light having a wavelength in the ultraviolet range).
- a conventionally used flammable and highly volatile organic solvent such as toluene and benzene
- a rubbery polymer that is flammable and has poor fluidity and extremely high viscosity
- an ionic liquid generally having properties such as extremely low vapor pressure (very low volatility) and flame retardancy is used.
- the light wavelength conversion element having the above-described configuration is relatively safe in practical use because it has relatively low volatility and relatively high flame retardancy.
- the light wavelength conversion element having the above structure dissolves and / or disperses the organic photosensitizing molecule (A) and the organic light emitting molecule (B) in the ionic liquid (C) having relatively high fluidity.
- the TTA process by the diffusion movement / mutual collision of the organic photosensitizing molecule (A) and the organic light emitting molecule (B) can be sufficiently advanced.
- the light wavelength conversion element having the above configuration has a relatively high light wavelength conversion efficiency.
- the light wavelength conversion element having the above-described configuration is a state in which the organic photosensitizing molecule (A) and the organic light emitting molecule (B) are “visually homogeneous and transparent” in the ionic liquid (C) having good thermal stability. Since it is dissolved and / or dispersed in, it has good temporal stability.
- “visually homogeneous and transparent” means that no layer separation of two or more layers has occurred visually, and to the extent that it can be visually confirmed, has no solids and is homogeneous, It shall mean that it is transparent without turbidity or cloudiness.
- dissolution and / or dispersion means either dissolution and dispersion, or simultaneous dissolution and dispersion.
- the solar cell of the present invention is characterized by using the light wavelength conversion element.
- the light has a high light wavelength conversion efficiency that can be applied to light as weak as the intensity of sunlight, and has good temporal stability.
- a light wavelength conversion element that can be converted into light having a wavelength in the ultraviolet region is used, a solar cell with high photoelectric conversion efficiency can be realized.
- the photocatalyst of the present invention is characterized by using the light wavelength conversion element.
- the light has a high light wavelength conversion efficiency that can be applied to light as weak as the intensity of sunlight, and has good temporal stability.
- a photocatalyst with high catalyst efficiency can be realized because an optical wavelength conversion element that can convert light into a wavelength in the ultraviolet region) is used.
- the photocatalytic hydrogen / oxygen generator of the present invention is characterized by using the light wavelength conversion element.
- the light has a high light wavelength conversion efficiency that can be applied to light as weak as the intensity of sunlight, and has good temporal stability.
- a photocatalytic hydrogen / oxygen generator having high hydrogen / oxygen generation efficiency can be realized.
- the optical up-conversion filter of the present invention is an optical up-conversion filter that converts light into light having a shorter wavelength, and includes the optical wavelength conversion element and a cell serving as a sealing / holding shell thereof, The wavelength conversion element is encapsulated in the cell.
- a light wavelength conversion element having high light wavelength conversion efficiency applicable to light as weak as sunlight intensity is used, so a photocatalytic hydrogen / oxygen generator with high hydrogen / oxygen generation efficiency is realized. it can.
- light having a wavelength in the ultraviolet to visible range which has high light wavelength conversion efficiency applicable to light as low as the intensity of sunlight and good temporal stability, can be converted into light having a shorter wavelength (for example,
- An optical wavelength conversion element that can be converted into light having a wavelength in the ultraviolet region) and an article (a solar cell, a photocatalyst, a photocatalytic hydrogen / oxygen generator, and an optical upconversion filter) including the optical wavelength conversion element can be provided.
- FIG. 3 is a diagram showing an up-conversion emission spectrum of the light wavelength conversion element obtained in Example 1. It is a figure which shows the light absorption spectrum of the light wavelength conversion element obtained in Example 1.
- FIG. It is a figure which shows the up-conversion emission spectrum of the light wavelength conversion element obtained in Example 2.
- FIG. 6 is a diagram showing an up-conversion emission spectrum of the light wavelength conversion element obtained in Example 3.
- FIG. It is a figure which shows the light absorption spectrum of the light wavelength conversion element obtained in Example 3.
- FIG. It is a figure which shows the up-conversion emission spectrum of the light wavelength conversion element obtained in Example 4. It is a figure which shows the light absorption spectrum of the light wavelength conversion element obtained in Example 4.
- FIG. It is a figure which shows the up-conversion emission spectrum of the light wavelength conversion element obtained in Example 5. It is a figure which shows the light absorption spectrum of the light wavelength conversion element obtained in Example 5.
- FIG. It is a figure which shows the up-conversion emission spectrum of the light wavelength conversion element obtained in Example 6. It is a figure which shows the light absorption spectrum of the light wavelength conversion element obtained in Example 6.
- FIG. It is a figure which shows the up-conversion emission spectrum of the light wavelength conversion element obtained in Example 7. It is a figure which shows the light absorption spectrum of the light wavelength conversion element obtained in Example 7.
- FIG. It is a figure which shows the up-conversion emission spectrum of the light wavelength conversion element obtained in Example 8 and Example 9. It is a figure which shows the up-conversion emission spectrum of the light wavelength conversion element obtained in Example 10. It is a figure which shows the light absorption spectrum of the light wavelength conversion element obtained in Example 10.
- FIG. It is a figure which shows the up-conversion emission spectrum of the light wavelength conversion element obtained in Example 11. It is a figure which shows the light absorption spectrum of the light wavelength conversion element obtained in Example 11.
- FIG. It is a figure which shows the up-conversion emission spectrum of the light wavelength conversion element obtained in Example 12. It is a figure which shows the light absorption spectrum of the light wavelength conversion element obtained in Example 12.
- the light wavelength conversion element of the present invention is obtained by dissolving and / or dispersing an organic photosensitizing molecule (A) and an organic light emitting molecule (B), which are a combination showing a TTA process, in an ionic liquid (C).
- the organic photosensitizing molecule (A) and the organic light emitting molecule (B) can be used without limitation as long as the combination exhibits a TTA process (light emission based on the TTA process).
- the organic photosensitizer molecule (A) can be a ⁇ -conjugated molecule having a light absorption band in the ultraviolet to visible range, and the organic light emitting molecule (B) has a light emitting band in the ultraviolet to visible range.
- a ⁇ -conjugated molecule can be used.
- organic photosensitizing molecule (A) and the organic light emitting molecule (B) include aromatic ⁇ -electron conjugated compounds, particularly polycyclic aromatic ⁇ -electron conjugated compounds, and for example, described in Non-Patent Document 5.
- aromatic ⁇ -electron conjugated compounds particularly polycyclic aromatic ⁇ -electron conjugated compounds, and for example, described in Non-Patent Document 5.
- a wide range of low molecules and polymers can be used.
- the organic photosensitizer molecule (A) can be used without limitation as long as it has the longest absorption maximum wavelength in the range of 250 to 499 nm, but the longest absorption maximum in the range of 330 to 499 nm. Those having a wavelength are preferable, those having the longest absorption maximum wavelength in the range of 350 to 499 nm are more preferable, and those having the longest absorption maximum wavelength in the range of 350 to 410 are more preferable.
- organic photosensitizing molecule (A) molecular species, low molecular compounds, and high molecular compounds that have not been called dyes so far can be used as long as they have the longest absorption maximum wavelength in the range of 250 to 499 nm.
- Supramolecules and the like can be used without particular limitation.
- Examples of the organic photosensitizer molecule (A) include acenaphthene derivatives, acetophenone derivatives, anthracene derivatives, diphenylacetylene derivatives, acridan derivatives, acridine derivatives, acridone derivatives, thioacridone derivatives, angelicin derivatives, anthracene derivatives, anthraquinone derivatives, azafluorenes.
- Derivatives azulene derivatives, benzyl derivatives, carbazole derivatives, coronene derivatives, sumanene derivatives, biphenylene derivatives, fluorene derivatives, perylene derivatives, phenanthrene derivatives, phenanthroline derivatives, phenazine derivatives, benzophenone derivatives, pyrene derivatives, benzoquinone derivatives, biacetyl derivatives, bianthranyl derivatives , Fullerene derivatives, graphene derivatives, carotene derivatives, chlorophyll derivatives, Derivatives, cinnoline derivatives, coumarin derivatives, curcumin derivatives, dansylamide derivatives, flavone derivatives, fluorenone derivatives, fluorescein derivatives, helicene derivatives, indene derivatives, lumichrome derivatives, lumiflavin derivatives, oxadiazole derivatives, oxazole derivatives, perifuranthene derivatives
- organic photosensitizing molecule (A) examples include acridones such as N-methylacridone and N-butyl-2-chloroacridone; thioxanthones such as 2,4-diethylthioxanthone.
- Xanthones xanthenes
- acridines such as acridine yellow
- coumarins such as coumarin 6 and coumarin 314
- biacetyls such as 2,3-butanedione
- 9,10-dibromoanthracene and 9, Anthracene such as 9'-bianthryl
- oligoaryls such as bifuran, bithiophene, bis (benzoxazolyl) thiophene
- condensed polycyclic heteroaromatic compounds such as chrysene, phenanthrene or derivatives thereof, etc.
- the organic photosensitizer molecule (A) is more preferably an organic photosensitizer molecule having a structure containing no metal in the structure. Thereby, it is possible to avoid the occurrence of environmental pollution due to metal at the time of manufacturing or discarding the optical wavelength conversion element.
- a compound having the longest absorption maximum wavelength in the range of 250 to 499 nm is represented by the following general formula ( 1)
- R 1 to R 8 each independently represents an arbitrary substituent containing a hydrogen atom and may be the same or different, and two of R 1 to R 8 adjacent to each other are connected to each other to form hydrogen
- a 5-membered or 6-membered ring having an arbitrary substituent containing an atom may be formed, and X is a thio group (—S—), a sulfinyl group (—S ( ⁇ O) —), a sulfonyl group (—S ( ⁇ O) 2 —), a divalent group represented by —N (R 9 ) —, or a divalent group represented by —C (R 10 ) (R 11 ) —, and R 9 to R 11 Each independently represents an optional substituent containing a hydrogen atom)
- the “arbitrary substituent containing a hydrogen atom” means a hydrogen atom or an arbitrary substituent other than a hydrogen atom.
- R 1 to R 8 in the general formula (1) examples include a hydrogen atom, an alkyl group (for example, an alkyl group having 1 to 12 carbon atoms), an alkenyl group, an alkynyl group, a halogen atom, a hydroxy group (hydroxyl group), Alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, carboxylate, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aminocarbonyl group, alkylaminocarbonyl group, dialkylaminocarbonyl group , Alkylthiocarbonyl group, alkoxyl group, phosphate group, phosphonate group, phosphinate group, cyano group, amino group (alkylamino group, dialkylamino group, arylamino group, diarylamino group, and alkylarylamino group ), Acylamino groups (including
- R 9 to R 11 include a hydrogen atom, an alkyl group (eg, an alkyl group having 1 to 12 carbon atoms), an alkenyl group, an alkynyl group, a heterocyclic group, an alkylaryl group, an aryl group, or a heteroaryl group.
- an alkyl group eg, an alkyl group having 1 to 12 carbon atoms
- an alkenyl group e.g., an alkynyl group having 1 to 12 carbon atoms
- a heterocyclic group e.g., an alkyl group having 1 to 12 carbon atoms
- X is a thio group
- R 1 to R 8 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a cyano group, a nitro group, or an aryl group. Or a heteroaryl group.
- X is a thio group, that is, a thioxanthone, for example, in addition to unsubstituted thioxanthone (CAS number: 492-22-8), 2, Substituted thioxanthones such as 4-diethylthioxanthone (CAS number: 82799-44-8), 2-isopropylthioxanthone (CAS number: 5495-84-1) and 2-chlorothioxanthone (CAS number: 86-39-5) It is done.
- X is a sulfinyl group, that is, a thioxanthone oxide, for example, in addition to unsubstituted thioxanthone oxide (CAS number: 7605-15-4).
- thioxanthone oxide for example, in addition to unsubstituted thioxanthone oxide (CAS number: 7605-15-4)
- substituted thioxanthones such as 3-methylthioxanthone oxide (CAS number: 654670-82-3) and thioxanthone oxide derivatives described in JP-A No. 58-120605.
- X is a sulfonyl group, that is, a thioxanthone dioxide, for example, an unsubstituted thioxanthone dioxide (CAS number: 3166-15-2)
- substituted thioxanthones such as 2-methylthioxanthone dioxide (CAS number: 87548-99-0) and thioxanthone dioxide derivatives described in JP-A No. 58-120605 can be mentioned.
- X is a divalent group represented by —N (R 9 ) —, that is, an acridone, for example, an unsubstituted acridone (CAS number) : 578-95-0), N-methylacridone (CAS number: 719-54-0), N-methyl-2-iodoacridone (CAS number: 1493782-35-6), N-butyl- Examples thereof include substituted acridones such as 2-chloroacridone (CAS number: 128420-54-2) and acridone derivatives described in JP-A-8-67873.
- an acridone for example, an unsubstituted acridone (CAS number) : 578-95-0), N-methylacridone (CAS number: 719-54-0), N-methyl-2-iodoacridone (CAS number: 1493782-35-6), N-butyl- Examples thereof include substituted acridones such as 2-chloroa
- X is a divalent group represented by —C (R 10 ) (R 11 ) —, that is, an anthrone, for example, unsubstituted
- substituted anthrone such as 3-methylanthrone (CAS number: 69653-12-9) and benzanthrone (CAS number: 82-05-3) can be mentioned.
- organic photosensitizer molecules (A) may be used alone or in combination of two or more.
- alkyl group means a substituted or unsubstituted alkyl group.
- substituent that can be used in the compound in the present invention may be any substituent.
- substituents include halogen atoms, alkyl groups (including cycloalkyl groups, bicycloalkyl groups, and tricycloalkyl groups), alkenyl groups (including cycloalkenyl groups and bicycloalkenyl groups), alkynyl groups, and aryl groups.
- heterocyclic group also referred to as heterocyclic group
- cyano group carbamoyloxy group, Alkylsulfonylamino group or arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkylsulfinyl group or arylsulfinyl group, alkylsulfonyl group or arylsulfonyl group, acid Group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, arylazo group or heterocyclic azo group, imide group, phosphino group, phosphinyl group, phosphinyloxyloxy
- examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- the alkyl group includes a linear, branched, or cyclic substituted or unsubstituted alkyl group.
- the alkyl group is an aliphatic alkyl group (preferably a substituted or unsubstituted aliphatic alkyl group having 1 to 30 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, t-butyl group, n- Octyl group, eicosyl group, 2-chloroethyl group, 2-cyanoethyl group, 2-ethylhexyl group), cycloalkyl group (preferably a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, such as cyclohexyl group, cyclopentyl Group, 4-n-dodecylcyclohexyl group), bicycloalkyl group (preferably a substituted or unsubstituted bicycl
- Monovalent groups such as bicyclo [1,2,2] heptan-2-yl group, bicyclo [2 2,2] octane-3-yl group), is intended to encompass three or more ring structures often tricycloalkyl group.
- An alkyl group (for example, an alkyl group of an alkylthio group) in the substituents described below includes an alkenyl group and an alkynyl group in addition to the above-described alkyl group.
- the alkenyl group includes a linear, branched, or cyclic substituted or unsubstituted alkenyl group.
- the alkenyl group is an aliphatic alkenyl group (preferably a substituted or unsubstituted aliphatic alkenyl group having 2 to 30 carbon atoms, such as vinyl group, allyl group, prenyl group, geranyl group, oleyl group), cycloalkenyl group ( Preferably, it is a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom of a cycloalkene having 3 to 30 carbon atoms, such as 2-cyclopentene-1- Yl group, 2-cyclohexen-1-yl group, etc.), bicycloalkenyl group (substituted or unsubstituted bicycloalkenyl group, that is, a mono
- the alkynyl group is preferably a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, such as an ethynyl group, a propargyl group, a trimethylsilylethynyl group, and the like.
- the aryl group is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, biphenyl group, p-tolyl group, naphthyl group, m-chlorophenyl group, o-hexadecanoylaminophenyl group, etc. It is.
- the heterocyclic group is preferably a monovalent group obtained by removing one hydrogen atom from a 5- or 6-membered substituted or unsubstituted aromatic or non-aromatic heterocyclic compound, and more preferably, A 5- or 6-membered aromatic heterocyclic group having 3 to 30 carbon atoms.
- heterocyclic group examples include a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group.
- the heterocyclic group may be a cationic heterocyclic group such as 1-methyl-2-pyridinio group or 1-methyl-2-quinolinio group.
- the alkoxy group is preferably a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, such as a methoxy group, an ethoxy group, an isopropoxy group, a t-butoxy group, an n-octyloxy group, or a 2-methoxyethoxy group.
- the aryloxy group is preferably a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, such as a phenoxy group, 2-methylphenoxy group, 4-t-butylphenoxy group, 3-nitrophenoxy group, 2 -Tetradecanoylaminophenoxy group and the like.
- the silyloxy group is preferably a silyloxy group having 3 to 20 carbon atoms, such as a trimethylsilyloxy group or a t-butyldimethylsilyloxy group.
- the heterocyclic oxy group is preferably a substituted or unsubstituted heterocyclic oxy group having 2 to 30 carbon atoms, such as a 1-phenyltetrazol-5-oxy group, a 2-tetrahydropyranyloxy group, and the like.
- the acyloxy group is preferably a formyloxy group, a substituted or unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms, or a substituted or unsubstituted arylcarbonyloxy group having 6 to 30 carbon atoms, such as a formyloxy group.
- the carbamoyloxy group is preferably a substituted or unsubstituted carbamoyloxy group having 1 to 30 carbon atoms, such as N, N-dimethylcarbamoyloxy group, N, N-diethylcarbamoyloxy group, morpholinocarbonyloxy group, N , N-di-n-octylaminocarbonyloxy group, Nn-octylcarbamoyloxy group and the like.
- the alkylsulfonylamino group or arylsulfonylamino group is preferably a substituted or unsubstituted alkylsulfonylamino group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsulfonylamino group having 6 to 30 carbon atoms, such as methyl A sulfonylamino group, a butylsulfonylamino group, a phenylsulfonylamino group, a 2,3,5-trichlorophenylsulfonylamino group, a p-methylphenylsulfonylamino group, and the like.
- the alkylthio group is preferably a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, such as a methylthio group, an ethylthio group, or an n-hexadecylthio group.
- the arylthio group is preferably a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, such as a phenylthio group, a p-chlorophenylthio group, an m-methoxyphenylthio group.
- the heterocyclic thio group is preferably a substituted or unsubstituted heterocyclic thio group having 2 to 30 carbon atoms, such as a 2-benzothiazolylthio group, a 1-phenyltetrazol-5-ylthio group, and the like.
- the sulfamoyl group is preferably a substituted or unsubstituted sulfamoyl group having 0 to 30 carbon atoms, such as N-ethylsulfamoyl group, N- (3-dodecyloxypropyl) sulfamoyl group, N, N-dimethylsulfa group.
- the alkylsulfinyl group or arylsulfinyl group is preferably a substituted or unsubstituted alkylsulfinyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfinyl group having 6 to 30 carbon atoms, such as a methylsulfinyl group, ethyl And sulfinyl group, phenylsulfinyl group, p-methylphenylsulfinyl group and the like.
- the alkylsulfonyl group or arylsulfonyl group is preferably a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms or a substituted or unsubstituted arylsulfonyl group having 6 to 30 carbon atoms such as a methylsulfonyl group, ethyl A sulfonyl group, a phenylsulfonyl group, a p-methylphenylsulfonyl group, and the like.
- the acyl group is preferably a formyl group, a substituted or unsubstituted alkylcarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted group having 4 to 30 carbon atoms.
- Heterocyclic carbonyl groups bonded to carbonyl groups at substituted carbon atoms eg, acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, pn-octyloxyphenylcarbonyl, 2-pyridyl A carbonyl group, a 2-furylcarbonyl group, and the like.
- the aryloxycarbonyl group is preferably a substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms such as phenoxycarbonyl group, o-chlorophenoxycarbonyl group, m-nitrophenoxycarbonyl group, pt- And a butylphenoxycarbonyl group.
- the alkoxycarbonyl group is preferably a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group, an n-octadecyloxycarbonyl group, and the like.
- the carbamoyl group is preferably a substituted or unsubstituted carbamoyl group having 1 to 30 carbon atoms, such as a carbamoyl group, an N-methylcarbamoyl group, an N, N-dimethylcarbamoyl group, an N, N-di-n-octyl group.
- the arylazo group or heterocyclic azo group is preferably a substituted or unsubstituted arylazo group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic azo group having 3 to 30 carbon atoms such as a phenylazo group and p-chlorophenyl.
- the imide group is preferably an N-succinimide group, an N-phthalimide group, or the like.
- the phosphino group is preferably a substituted or unsubstituted phosphino group having 2 to 30 carbon atoms, such as a dimethylphosphino group, a diphenylphosphino group, a methylphenoxyphosphino group, and the like.
- the phosphinyl group is preferably a substituted or unsubstituted phosphinyl group having 2 to 30 carbon atoms, such as a phosphinyl group, a dioctyloxyphosphinyl group, a diethoxyphosphinyl group, and the like.
- the phosphinyloxy group is preferably a substituted or unsubstituted phosphinyloxy group having 2 to 30 carbon atoms, such as a diphenoxyphosphinyloxy group or a dioctyloxyphosphinyloxy group.
- the phosphinylamino group is preferably a substituted or unsubstituted phosphinylamino group having 2 to 30 carbon atoms, such as a dimethoxyphosphinylamino group or a dimethylaminophosphinylamino group.
- the silyl group is preferably a substituted or unsubstituted silyl group having 3 to 30 carbon atoms, such as a trimethylsilyl group, a t-butyldimethylsilyl group, or a phenyldimethylsilyl group.
- the hydrazino group is preferably a substituted or unsubstituted hydrazino group having 0 to 30 carbon atoms, such as a trimethylhydrazino group.
- the ureido group is preferably a substituted or unsubstituted ureido group having 0 to 30 carbon atoms, such as an N, N-dimethylureido group.
- substituents include those in which two substituents jointly form a ring.
- the ring is an aromatic or non-aromatic hydrocarbon ring or heterocyclic ring. These rings can be further combined to form a polycyclic fused ring. Examples of the ring include a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, triphenylene ring, naphthacene ring, biphenyl ring, pyrrole ring, furan ring, thiophene ring, imidazole ring, oxazole ring, thiazole ring, pyridine.
- substituents those having a hydrogen atom may be removed and further substituted with the above substituents.
- substituents include halogen atoms, alkyl groups (including cycloalkyl groups, bicycloalkyl groups, and tricycloalkyl groups), alkenyl groups (including cycloalkenyl groups and bicycloalkenyl groups), and alkynyl groups described above.
- alkyl groups including cycloalkyl groups, bicycloalkyl groups, and tricycloalkyl groups
- alkenyl groups including cycloalkenyl groups and bicycloalkenyl groups
- alkynyl groups described above.
- the organic light emitting molecule (B) is not particularly limited as long as it is an organic compound capable of emitting light up-converted by the TTA process when used with the organic photosensitizer molecule (A).
- the emission maximum wavelength from the light wavelength conversion element of the present invention is preferably in the range of 400 nm or less. Thereby, it is possible to realize an optical wavelength conversion element capable of converting light having a wavelength of 250 to 499 nm in the ultraviolet to visible range into light having a shorter wavelength and having a wavelength of 400 nm or less.
- Examples of the organic light emitting molecule (B) include acenaphthene derivatives, acetophenone derivatives, anthracene derivatives, diphenylacetylene derivatives, acridan derivatives, acridine derivatives, acridone derivatives, thioacridone derivatives, angelicin derivatives, anthracene derivatives, anthraquinone derivatives, azafluorene derivatives, Azulene derivatives, benzyl derivatives, carbazole derivatives, coronene derivatives, sumanene derivatives, biphenylene derivatives, fluorene derivatives, perylene derivatives, phenanthrene derivatives, phenanthroline derivatives, phenazine derivatives, benzophenone derivatives, pyrene derivatives, benzoquinone derivatives, biacetyl derivatives, bianthranyl derivatives, fullerenes Derivatives, graphene derivatives, carotene derivative
- organic light emitting molecule (B) those having a light emission maximum wavelength in the range of 200 to 400 nm are usually used, and those having a light emission maximum wavelength in the range of 250 to 400 nm are preferably used.
- organic light-emitting molecule (B) examples include 9,10-diphenylanthracene (CAS number: 1499-10-1) and derivatives thereof, and 9,10-bis (phenylethynyl) anthracene (CAS number).
- naphthalene and derivatives thereof eg 1-dodecylnaphthalene, naphthalene diimide, perfluoronaphthalene, 1-cyanonaphthalene, 1-methoxynaphthalene, 2-cyanonaphthalene, 2-methoxynaphthalene, 1-methyl Naphthalene, acenaphth ), 9,10-bis (phenylethynyl) naphthacene, 4,4′-bis (5-tetraaceenyl) -1,1′-biphenylene, indole, benzofuran, benzothiophene, biphenyl and its derivatives
- Z represents a divalent group represented by —C (R 18 ) ⁇ Y—, a divalent group represented by —N (R 20 ) —, an oxy group (—O—), or a thio group.
- Y represents a trivalent group represented by ⁇ C (R 19 ) — or an aza group ( ⁇ N—), and R 12 to R 20 each independently represents an arbitrary substituent containing a hydrogen atom. May be the same or different, and two of R 12 to R 20 that are adjacent to each other may be linked to each other to form a 5-membered or 6-membered ring having an arbitrary substituent containing a hydrogen atom)
- the compound represented by these is mentioned.
- R 12 to R 19 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a cyano group, a nitro group, an aryl group, or a heteroaryl group.
- R 20 is preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a heterocyclic group, an alkylaryl group, an aryl group, or a heteroaryl group.
- Y represents a trivalent group represented by ⁇ C (R 19 ) — or an aza group
- R 12 to R 19 each independently represents an arbitrary substituent containing a hydrogen atom
- Two of R 12 to R 19 that are adjacent to each other may be linked to each other to form a 5-membered or 6-membered ring having an arbitrary substituent containing a hydrogen atom
- the compound represented by these is preferable.
- R 12 to R 19 each independently represents an arbitrary substituent containing a hydrogen atom and may be the same or different, and two of R 12 to R 19 adjacent to each other are connected to each other to form hydrogen A 5-membered ring or a 6-membered ring having an arbitrary substituent containing an atom may be formed
- the compound represented by these is preferable.
- R 12 to R 19 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a cyano group, a nitro group, an aryl group, or a heteroaryl group. It is preferable that
- R 21 to R 26 each independently represents an arbitrary substituent containing a hydrogen atom, and may be the same or different, and two of R 21 to R 26 adjacent to each other are connected to each other to form hydrogen;
- a 5-membered ring or a 6-membered ring having an arbitrary substituent containing an atom may be formed,
- Q represents a divalent group represented by —N (R 27 ) —, an oxy group, or a thio group, and
- the compound represented by these is mentioned.
- R 33 to R 42 each independently represents an arbitrary substituent containing a hydrogen atom, and may be the same or different, and two of R 33 to R 42 adjacent to each other are connected to each other to form hydrogen;
- a 5-membered or 6-membered ring having an arbitrary substituent containing an atom may be formed, and R 33 and R 42 are connected to each other to form a 5-membered or 6-membered ring having an optional substituent containing a hydrogen atom
- a ring may be formed, and R 37 and R 38 may be linked to each other to form a 5-membered ring or a 6-membered ring having an arbitrary substituent containing a hydrogen atom
- the compound represented by these is mentioned.
- an arbitrary substituent containing a hydrogen atom means a hydrogen atom or an arbitrary substituent other than a hydrogen atom.
- R 12 to R 17 , R 21 to R 26 , and R 33 to R 42 in the general formulas (3) to (6) include a hydrogen atom, an alkyl group (for example, an alkyl group having 1 to 12 carbon atoms) ), Alkenyl group, alkynyl group, halogen atom, hydroxy group (hydroxyl group), alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, carboxylate, alkylcarbonyl group, arylcarbonyl group, Alkoxycarbonyl group, aminocarbonyl group, alkylaminocarbonyl group, dialkylaminocarbonyl group, alkylthiocarbonyl group, alkoxyl group, phosphate group, phosphonate group, phosphinate group, cyano group, amino group (alkylamino group, dialkylamino group , Arylamino , Diarylamino group, and alkyl
- R 20 , R 27 and R 28 include a hydrogen atom, an alkyl group (eg, an alkyl group having 1 to 12 carbon atoms), an alkenyl group, an alkynyl group, a heterocyclic group, an alkylaryl group, an aryl group, or a hetero group. Examples include, but are not limited to, aryl groups.
- R 12 to R 28 and R 33 to R 42 that may be included in the general formulas (3) to (6), two adjacent ones have a 5-membered ring or 6-membered ring formed by connecting each other A substituent, a substituent having a 5-membered ring or a 6-membered ring having an arbitrary substituent containing a hydrogen atom by bonding R 33 and R 42, and a hydrogen atom by bonding R 37 and R 38 to each other;
- optional substituents containing include, but are not limited to, the substituents listed as examples of R 1 to R 8 .
- Y is a trivalent group represented by —C (R 19 ) ⁇ , that is, naphthalene, for example, unsubstituted naphthalene (CAS number) : 91-20-3), octafluoronaphthalene (CAS number: 313-72-4), 2-methoxynaphthalene (CAS number: 93-04-9) and 2-cyanonaphthalene (CAS number: 613-46). -7), 1-dodecylnaphthalene (CAS number: 38641-16-6), 1-methylnaphthalene (CAS number: 90-12-0), acenaphthene (CAS number: 83-32-9), etc. Can be mentioned.
- naphthalene for example, unsubstituted naphthalene (CAS number) : 91-20-3), octafluoronaphthalene (CAS number: 313-72-4), 2-methoxynaphthalene (CAS number: 93-04-9) and 2-cyan
- Y is an aza group, that is, a quinoline, for example, in addition to unsubstituted quinoline (CAS number: 91-22-5), 6- Examples thereof include substituted naphthalenes such as tertiary butyl quinoline (CAS number: 68141-13-9) and benzo [h] quinoline (CAS number: 230-27-3).
- Z is a divalent group represented by —N (R 20 ) —, that is, an indole, for example, an unsubstituted indole (CAS number) : 120-72-9), and substituted indoles such as 1,2-dimethylindole (CAS number: 875-79-6) and naphthostyryl (CAS number: 130-00-7).
- an indole for example, an unsubstituted indole (CAS number) : 120-72-9), and substituted indoles such as 1,2-dimethylindole (CAS number: 875-79-6) and naphthostyryl (CAS number: 130-00-7).
- Z is an oxy group, that is, a benzofuran, for example, in addition to unsubstituted benzofuran (CAS number: 271-89-6), 2- Examples thereof include substituted benzofurans such as butyl benzofuran (CAS number: 4265-27-4) and diphenylene oxide (CAS number: 132-64-9).
- Z is a thio group, that is, a benzothiophene, for example, in addition to unsubstituted benzothiophene (CAS number: 95-15-8), Examples thereof include substituted benzofurans such as 2-methylbenzothiophene (CAS number: 1195-14-8) and dibenzothiophene (CAS number: 132-65-0).
- substituted benzofurans such as 2-methylbenzothiophene (CAS number: 1195-14-8) and dibenzothiophene (CAS number: 132-65-0).
- Q is a divalent group represented by —N (R 27 ) —
- R is a divalent group represented by —N (R 28 ) —.
- bipyrroles for example, in addition to unsubstituted bipyrrole (CAS number: 10090-64-6), 5,5′-dimethyl-bipyrrole (CAS number: 90888-56-5) and 1, Examples thereof include substituted bipyrroles such as 1′-dimethyl-bipyrrole (CAS number: 34671-26-6).
- Examples of the compound represented by the general formula (6) include unsubstituted biphenyl (CAS number: 92-52-4) and substitution such as p-terphenyl (CAS number: 92-94-4). Biphenyl is mentioned.
- These organic light emitting molecules (B) may be used alone or in combination of two or more.
- the organic photosensitizer molecule (A) and the organic light emitting molecule (B) can be freely selected from the above examples and can be used in any combination. However, in order to emit light up-converted light by the TTA process. In view of the efficiency of triplet-triplet energy transfer, it is preferable that the energy levels of the lowest triplet excited state of the organic photosensitizer molecule (A) and the organic light emitting molecule (B) are close. Therefore, the following formula
- the ⁇ E T represented by the formula (1) is preferably ⁇ 0.5 eV or more and 2.0 eV or less, more preferably ⁇ 0 .0V, for any combination of the organic photosensitizer molecule (A) and the organic light emitting molecule (B). It is 3 eV or more and 1.0 eV or less, more preferably ⁇ 0.2 eV or more and 0.5 eV or less, and particularly preferably ⁇ 0.1 eV or more and 0.3 eV or less.
- 1 eV is energy that an electron obtains when one electron is accelerated by a potential difference of 1 V.
- the absorption maximum wavelength of the longest wavelength is 250 to 499 nm, preferably 330 to 499 nm, more preferably 350 to 499 nm, Preferably absorbs light such as in the range of 350-410 nm and has a wavelength range of absorbed light of 200-400 nm, preferably 250-400 nm, more preferably 250-390 nm, even more preferably 250-360 nm.
- an optical wavelength conversion element optical upconverter having a light emission maximum wavelength in the wavelength region on the short wavelength side can be obtained.
- the contents of the organic photosensitizer molecule (A) and the organic light emitting molecule (B) in the light wavelength conversion element of the present invention are not particularly limited, but each is usually normal when the light wavelength conversion element is 100 parts by mass. Is 0.000001 to 10 parts by mass, preferably 0.00001 to 5 parts by mass, and more preferably 0.0001 to 1 part by mass.
- the ionic liquid (C) is a room temperature molten salt (a salt in a molten state (liquid state) at room temperature (25 ° C.)) composed of a cation and an anion. Generally, it is known that there are at least 1,000,000 kinds of compounds as ionic liquids depending on the combination of a cation and an anion.
- the ionic liquid (C) acts as a medium for the organic photosensitizing molecule (A) and the organic light emitting molecule (B), which is a combination showing the TTA process, and inside the organic photosensitizing molecule (A) and the organic The diffusion movement of the luminescent molecule (B) is allowed.
- the organic photosensitizing molecule (A) and the organic light emitting molecule (B), which are a combination showing the TTA process, are dissolved and / or dispersed in the ionic liquid (C) and visually observed. Since it is necessary to make it homogeneous and transparent, the ionic liquid (C) has a cation- ⁇ interaction with the organic photosensitizer molecule (A) and the organic light emitting molecule (B) and is immiscible with water.
- the ionic liquid (C) is “non-water miscible” means that 50% by mass or less of water is visually and homogeneously mixed with the ionic liquid (C) at 25 ° C. (for example, 5% by mass or less of water may be visually homogeneously and transparently mixed with the ionic liquid (C)), but 50% by mass of water is not visually homogeneously and transparently mixed with the ionic liquid (C). means.
- the cation constituting the ionic liquid (C) include, for example, a nitrogen-containing compound cation, a quaternary phosphonium cation, a sulfonium cation, and the like.
- the nitrogen-containing compound cation include heterocyclic aromatic amine cations such as imidazolium cation and pyridinium cation; piperidinium cation, pyrrolidinium cation, pyrazolium cation, thiazolium cation, and morpholinium cation.
- Heterocyclic aliphatic amine cations such as quaternary ammonium cations, aromatic amine cations, aliphatic amine cations, and alicyclic amine cations.
- Examples of the imidazolium cation include 1-ethyl-3-methylimidazolium, 1-butyl-3-methylimidazolium, 1-hexyl-3-methylimidazolium, and 1-octyl-3-methylimidazolium.
- 1-alkyl-3-methylimidazolium 1-ethyl-2,3-dimethylimidazolium, 1-propyl-2,3-dimethylimidazolium, 1-butyl-2,3-dimethylimidazolium, 1-pentyl- 1-alkyl-2 such as 2,3-dimethylimidazolium, 1-hexyl-2,3-dimethylimidazolium, 1-heptyl-2,3-dimethylimidazolium, 1-octyl-2,3-dimethylimidazolium , 3-Dimethylimidazolium; 1-cyanomethyl-3-methylimidazolium, 1- (2-hydride Kishiechiru) -3-methylimidazolium, and the like.
- Examples of the pyridinium cation include 1-butylpyridinium, 1-hexylpyridinium, N- (3-hydroxypropyl) pyridinium, N-hexyl-4-dimethylaminopyridinium, and the like.
- Examples of the piperidinium cation include 1- (methoxyethyl) -1-methylpiperidinium.
- Examples of the pyrrolidinium cation include 1- (2-methoxyethyl) -1-methylpyrrolidinium, N- (methoxyethyl) -1-methylpyrrolidinium, and the like.
- Examples of the morpholinium cation include N- (methoxyethyl) -N-methylmorpholium.
- Examples of the quaternary ammonium cation include N, N-diethyl-N-methyl-N- (2-methoxyethyl) ammonium, N-ethyl-N, N-dimethyl-2-methoxyethylammonium and the like.
- Examples of the quaternary phosphonium cation include tetraalkylphosphonium and tetraphenylphosphonium.
- Examples of the sulfonium cation include trialkylsulfonium and triphenylsulfonium. One kind of these cations may be present in the ionic liquid (C), or two or more kinds may be present.
- the cation constituting the ionic liquid (C) may be an organic photosensitizing molecule. Those having a “cation- ⁇ interaction” between (A) and the organic light emitting molecule (B) are preferred.
- the anion constituting the ionic liquid (C) is not particularly limited.
- an ionic liquid is miscible with water depending on the type of anion that constitutes the ionic liquid, but depending on the type of anion that constitutes the ionic liquid, the ionic liquid is not miscible with water to a certain extent, or a very small amount. Only miscible.
- the anion of the ionic liquid (C) is converted into the ionic liquid.
- An anion that imparts non-water miscibility is preferred.
- ionic liquid (C) a combination of a specific example of the anion and a specific example of the cation can be used.
- ionic liquid (C) more specifically, for example, 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide (CAS number: 174899-82-2, for example, the manufacturer is Ionic Liquids Technologies) GmbH is commercially available), 1-propyl-2,3-dimethylimidazolium bis (trifluoromethylsulfonyl) imide (CAS number: 169051-76-7, for example, the manufacturer is IoLiTech Ionic Liquids Technologies GmbH, Commercially available from Merck KGaA), 1-butyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide (CAS number: 174899-83-3, for example, manufacturer I Commercial products of LiTec Ionic Liquids Technologies GmbH and commercial products of Merck KGaA available from the manufacturer), 1-
- a commercial product manufactured by Nisshinbo Co., Ltd. and sold by Kanto Chemical Co., Ltd. product number: 11468-55
- 1-hexyl-3-methylimidazolium bis (trifluoromethylsulfonyl) Mido CAS number: 382150-50-7, for example, commercially available from the manufacturer Merck KGaA
- 1-octyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide (CAS number: 178631-4-4)
- the manufacturer is Nisshinbo Co., Ltd.
- the distributor is Kanto Chemical Co., Ltd.
- the organic light is selected from the ionic liquid (C).
- a combination of a cation having a “cation- ⁇ interaction” between the sensitizing molecule (A) and the organic light-emitting molecule (B) and an anion that imparts non-water miscibility to the ionic liquid is preferable.
- the ionic liquid (C) Also, non-water miscible ones are preferable.
- Examples of the ionic liquid (C) include 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide, 1-propyl-2,3-dimethylimidazolium bis ( Trifluoromethylsulfonyl) imide, 1-butyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide, 1-propyl-2,3-dimethylimidazolium tris (trifluoromethylsulfonyl) methide, N, N-diethyl -N-methyl-N- (2-methoxyethyl) ammonium bis (trifluoromethylsulfonyl) imide, 1-hexyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide, 1-octyl-3-methylimidazolium Bis (trifluoromethylsulfonyl) 1-ethyl-2,3-dimethyl
- the viscosity of the ionic liquid (C) at 26 ° C. is usually 10 mPa ⁇ s or more, preferably 50 mPa ⁇ s or more, more preferably 70 mPa ⁇ s or more.
- the pH of the water after washing is greater than 5. More preferred. As a result, an optical wavelength conversion element having higher optical wavelength conversion efficiency and better temporal stability can be realized.
- the pH of the water after washing is 9 times that of the ionic liquid (C) ( A method of separating the aqueous layer and measuring the pH of the aqueous layer after adding ultrapure water (9 times its volume by volume) and stirring.
- “ultra pure water” means water having an electrical resistivity of 15 M ⁇ ⁇ cm or more measured by a measuring method of JIS K 0552.
- ionic liquids often exhibit an acidic pH of 5 or less after washing when the ionic liquid is washed with 9 times its volume of ultrapure water.
- an ionic liquid (C) can be obtained, and the ionic liquid (C) can be used.
- Examples of the method for removing impurities from the ionic liquid include (1) a method of treating the ionic liquid with activated carbon, (2) a method of washing the ionic liquid with water, and (3) a method of washing the ionic liquid with an organic solvent (for example, see JP 2012-144441 A), (4) After obtaining a solution by dissolving an ionic liquid in a solvent, the temperature of the solution is lowered to crystallize the ionic liquid from the solution, and the crystallized ionic liquid (5) A column packed with a filler such as alumina after obtaining a solution by dissolving an ionic liquid in a solvent.
- (6) a method of treating an ionic liquid with a metal hydride (Japanese Patent Laid-Open No. 2005-89313) Reference), and the like. A plurality of these methods may be used in combination.
- water preferably ultrapure water
- the washing treatment for removing the aqueous layer is repeated until the pH of the water after washing becomes higher than 5.
- a method of distilling water (drying) by heating under reduced pressure can be used.
- the content of the ionic liquid (C) is usually 10 parts by mass or more, preferably 30 parts by mass or more with respect to 100 parts by mass of the light wavelength conversion element.
- the light wavelength conversion element of the present invention is a solution or dispersion obtained by dissolving and / or dispersing an organic photosensitizer molecule (A) and an organic light emitting molecule (B) in an ionic liquid (C) using a generally known technique.
- Can be produced by a method of obtaining In the above method, if necessary, other additives are mixed with the organic photosensitizer molecule (A) and the organic light emitting molecule (B) in the ionic liquid (C) using a generally known technique, and the solution or A dispersion may be obtained.
- a known disperser such as an ultrasonic disperser, a bead mill, a homogenizer, a wet jet mill, a ball mill, an attritor, a sand mill, a roll mill, and a microwave disperser may be used alone or in combination.
- the organic photosensitizing molecule (A) and the organic light emitting molecule (B) may be finely pulverized and finely dispersed to obtain a solution or dispersion.
- the organic photosensitizer molecule (A) and the organic light emitting molecule (B) are dissolved and / or dispersed in a volatile organic solvent, Next, the obtained solution and / or dispersion is stirred and mixed with the ionic liquid (C) to form a visually homogeneous and transparent solution and / or dispersion, and the solution and / or dispersion is further subjected to reduced pressure.
- the method of removing this volatile organic solvent to a trace amount or less can also be used. This method makes it easy to obtain a light wavelength conversion element that is homogeneously and transparently mixed, and a light wavelength conversion element having high stability and high light wavelength conversion efficiency can be obtained. Therefore, the light wavelength conversion element of the present invention is obtained. More preferable as a method.
- the volatile organic solvent used in the method can dissolve and / or disperse the organic photosensitizer molecule (A) and the organic light emitting molecule (B), and can be mixed homogeneously and transparently with the ionic liquid (C). Furthermore, there is no particular limitation as long as it is a volatile organic solvent that can be removed to a trace amount under reduced pressure.
- the “trace amount” is an amount that can detect the volatile organic solvent mixed in the ionic liquid (C) only at a noise level or less based on the measurement of the light absorption spectrum.
- the volatile organic solvent is preferably a volatile organic solvent that can dissolve the organic photosensitizing molecule (A) and the organic light emitting molecule (B).
- the volatile organic solvent aromatic solvents such as toluene, benzene and xylene can be used.
- a volatile organic solvent capable of dissolving the organic photosensitizing molecule (A) and the organic light emitting molecule (B) is used, the volatile organic solvent matches the solubility of the organic photosensitizing molecule and the organic light emitting molecule. Can be selected as appropriate.
- stirring and mixing means known techniques or devices such as ultrasonic waves, bubbling, agitators, liquid feed pumps, pulverizers, bead mills, homogenizers, wet jet mills, and microwaves can be used. These means may be used alone or in combination of two or more.
- the convenience during handling is improved as a component other than the organic photosensitizer molecule (A), the organic light emitting molecule (B), and the ionic liquid (C).
- Various additives such as ionic and nonionic gelling agents (D), antifoaming agents, leveling agents, light stabilizers, antioxidants, polymerization inhibitors, antistatic agents, UV absorbers, etc. Can be added.
- the light wavelength conversion element of the present invention may further contain a gelling agent (D) as described above. Since the light wavelength conversion element having the above-described structure contains the gelling agent (D), the fluidity is suppressed as compared with the case where the gelling agent (D) is not included, and the solar cell, photocatalyst, photocatalytic hydrogen, When used in articles such as oxygen generators and optical up-conversion filters, leakage of the light wavelength conversion element is unlikely to occur.
- a gelling agent (D) as described above. Since the light wavelength conversion element having the above-described structure contains the gelling agent (D), the fluidity is suppressed as compared with the case where the gelling agent (D) is not included, and the solar cell, photocatalyst, photocatalytic hydrogen, When used in articles such as oxygen generators and optical up-conversion filters, leakage of the light wavelength conversion element is unlikely to occur.
- the light wavelength conversion element of the present invention further comprising a gelling agent (D) is preferably in a gel state.
- a gelling agent (D) is preferably in a gel state.
- the gelling agent (D) a gel that is dissolved in the ionic liquid (C) and has a light transmittance that does not inhibit the light absorption of the organic photosensitizing molecule (A) and the light emission of the organic light emitting molecule (B).
- an ionic gelling agent and a nonionic polymer are preferable because a gel having sufficient light permeability can be formed.
- An ionic gelling agent is more preferable because a gel can be easily formed in D).
- A represents a divalent group or cyclohexanediyl group having one or more aromatic rings which may have a substituent
- B represents an alkylene having 1 to 10 carbon atoms which may have a substituent.
- X - represents a monovalent anion
- n is in each molecule represents a positive integer
- the average value of n of the total molecule is from 1 to 800
- the cyclohexanediyl group is, for example, a cyclohexane-1,4-diyl group.
- B in the general formula (A) is preferably an alkylene group having 1 to 6 carbon atoms which may have a substituent, and an alkylene having 2 to 6 carbon atoms which may have a substituent. More preferably, it is a group.
- the substituent that the alkylene group may have include an alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, and propyl groups; an alkoxy group having 1 to 6 carbon atoms such as methoxy, ethoxy, and propoxy groups. It is done.
- B in the general formula (A) include, for example, methylene group, ethane-1,2-diyl group, propane-1,4-diyl group, butane-1,4-diyl group, hexane-1 , 6-diyl group, 2-butene-1,4-diyl group and the like.
- X ⁇ in the general formula (A) is not limited, and examples thereof include halide ions (F ⁇ , Cl ⁇ , Br ⁇ , or I ⁇ ), bis (trifluoromethanesulfonyl) amide ions, Bis (fluorosulfonyl) amide ion, tetrafluoroborate ion (BF 4 ⁇ ), hexafluorophosphate ion (PF 6 ⁇ ), thiocyanate ion (SCN ⁇ ), nitrate ion (NO 3 ⁇ ), methosulphate ion ( CH 3 OSO 3 ⁇ ), bicarbonate ion (HCO 3 ⁇ ), hypophosphite ion (H 2 PO 2 ⁇ ), halogen oxoacid ion (YO 4 ⁇ , YO 3 ⁇ , YO 2 ⁇ , or YO ⁇ Y represents Cl, Br, or I), tris (tri
- X ⁇ in the general formula (A) is preferably bis (trifluoromethanesulfonyl) amide ion, bis (fluorosulfonyl) amide ion, or tetrafluoroborate ion (BF 4 ⁇ ).
- Preferred examples of the compound represented by the general formula (A) include the following general formula
- B represents an ethylene group, a 1,3-propylene group, a 1,4-butylene group or a 1,6-hexalene group
- X ⁇ represents a halide ion (F ⁇ , Cl ⁇ , Br ⁇ , or I ⁇ ), bis (trifluoromethanesulfonyl) amide ion, bis (fluorosulfonyl) amide ion, tetrafluoroborate ion (BF 4 ⁇ ), hexafluorophosphate ion (PF 6 ⁇ ), thiocyanate ion (SCN ⁇ ), nitrate ion (NO 3 ⁇ ), methosulfate ion (CH 3 OSO 3 ⁇ ), bicarbonate ion (HCO 3 ⁇ ), hypophosphite ion (H 2 PO 2 ⁇ ), halogen oxoacid Ion (YO 4 ⁇ ,
- the concentration of the ionic gelling agent in the light wavelength conversion element of the present invention is usually 0.3 to 100 g / L, preferably 0.5 to 60 g, although it depends on the value of n of the ionic gelling agent. More preferably, it is 1 to 20 g.
- concentration of the ionic gelling agent is less than 0.3 g / L, the light wavelength conversion element may not be sufficiently gelled.
- concentration of the ionic gelling agent exceeds 100 g / L, the light transmittance of the gel formed by dissolving the ionic gelling agent in the ionic liquid (C) is lowered, and the light wavelength conversion of the light wavelength conversion element There is a risk that the characteristics will deteriorate.
- the nonionic polymer at least one kind of a compound capable of forming a nonionic polymer by a polymerization reaction described in detail later can be used.
- the nonionic polymer preferably has a lower absorbance.
- the light wavelength conversion element of the present invention containing the gelling agent (D), for example, (1) A first solution and / or dispersion obtained by dissolving and / or dispersing an organic photosensitizing molecule (A) in an ionic liquid (C), and an organic luminescent molecule (B) as an ionic liquid (C) A liquid mixture obtained by dissolving a mixture of the second solution and / or dispersion liquid dissolved and / or dispersed therein, the ionic gelling agent and the ionic liquid (C) in a volatile organic solvent ( Solution), the second solution and / or dispersion liquid and the liquid mixture are mixed with the first solution and / or dispersion liquid, and then the volatile organic solvent is distilled off.
- a first solution and / or dispersion obtained by dissolving and / or dispersing an organic photosensitizing molecule (A) in an ionic liquid (C), and an organic luminescent molecule (B) as an ionic liquid (C)
- a solution and / or dispersion obtained by dissolving and / or dispersing the organic photosensitizing molecule (A) and the organic light-emitting molecule (B) in the ionic liquid (C) is converted into an ionic gelling agent and an ionic liquid.
- a method of mixing with a mixture (solution or gel) with (C) (3) A solution and / or dispersion obtained by dissolving and / or dispersing the organic photosensitizing molecule (A) and the organic light emitting molecule (B) in the ionic liquid (C) is made volatile with the ionic gelling agent.
- a method of distilling off a volatile organic solvent after mixing with a solution dissolved in an organic solvent It can manufacture using methods, such as.
- the method (1) is more preferable.
- the method (1) since the mixture of the ionic gelling agent and the ionic liquid (C) is used in a liquid state, it is compared with the method (2) in which a mixture having a high viscosity and often difficult to handle is used as it is. In addition, since the mixture has a low viscosity, it is easy to handle. As a result, the accuracy of the concentration of the ionic gelling agent in the light wavelength conversion element can be improved, and the light wavelength with higher uniformity can be obtained. A conversion element can be obtained.
- the liquid mixture obtained by dissolving the mixture of the ionic gelling agent and the ionic liquid (C) in the method (1) in a volatile organic solvent is, for example, (i) the ionic liquid (C).
- the mixture is volatile. It can be produced by a method of homogenizing by adding an organic solvent and stirring. In the method (ii), heating at a relatively high temperature (for example, 140 ° C.
- the gelling agent (D) is an ionic gelling agent.
- the gelling agent mixture is easy to homogenize and can be accurately weighed, and uniformly mixed with organic photosensitizer molecules (A), organic light emitting molecules (B), ionic liquids (C), etc. Any method that satisfies the requirements of being easy to do.
- a solution and / or dispersion obtained by dissolving and / or dispersing the organic photosensitizer molecule (A) and the organic light emitting molecule (B) used in the methods (2) and (3) in the ionic liquid (C) is:
- the organic photosensitizer molecule (A) is dissolved in a volatile organic solvent to prepare a solution of the organic photosensitizer molecule (A), and the organic light emitting molecule (B) is dissolved in a volatile organic solvent.
- the organic luminescent molecule (B) solution is prepared, and then the organic photosensitized molecule (A) solution, the organic luminescent molecule (B) solution, and the ionic liquid (C) are mixed and homogenized by stirring. Then, it can be produced by a method of distilling off the volatile organic solvent.
- the volatile organic solvent used in the production of the light wavelength conversion element of the present invention can dissolve and / or disperse the ionic gelling agent and / or can be mixed homogeneously and transparently with the ionic liquid (C).
- the “trace amount” is an amount that can detect the volatile organic solvent mixed in the ionic liquid (C) only at a noise level or less based on the measurement of the light absorption spectrum.
- the volatile organic solvent is preferably a volatile organic solvent that can dissolve the ionic gelling agent.
- an alcohol solvent such as methanol can be used.
- the light wavelength conversion element of the present invention containing the gelling agent (D) is, for example, (I) organic photosensitizing molecule (A) and organic After impregnating a nonionic polymer with a mixture of a volatile organic solvent and ionic liquid (C) in which the luminescent molecule (B) is dissolved and / or dispersed, the volatile organic solvent is removed under reduced pressure. (II) a solution and / or dispersion obtained by dissolving and / or dispersing the organic photosensitizing molecule (A) and the organic light emitting molecule (B) in the ionic liquid (C), and a polymerization reaction.
- a polymerizable compound capable of forming a nonionic polymer
- a polymerization reaction of the polymerizable compound is performed to obtain a nonionic polymer. It can manufacture using methods, such as the method of forming.
- a solution and / or dispersion obtained by dissolving and / or dispersing the organic photosensitizing molecule (A) and the organic light emitting molecule (B) in a volatile organic solvent and an ionic liquid (C) is, for example, organic light.
- the sensitized molecule (A) is dissolved in a volatile organic solvent to prepare a solution of the organic photosensitized molecule (A), and the organic luminescent molecule (B) is dissolved in a volatile organic solvent to prepare an organic luminescent molecule ( A solution of B) is prepared, and the solution of the organic photosensitizer molecule (A), the solution of the organic light emitting molecule (B), and the ionic liquid (C) are mixed and manufactured by a method of homogenizing by stirring. it can. Further, the order of mixing the solution of the organic photosensitizing molecule (A), the solution of the organic light emitting molecule (B), and the ionic liquid (C) is not particularly limited.
- the ionic liquid (C) On the other hand, after mixing the solution of the organic light emitting molecule (B), the solution of the organic photosensitized molecule (A) and the solution of the organic light emitting molecule (B) can also be mixed.
- the organic photosensitizer molecule (A) and the organic light emitting molecule (B) are dissolved and / or dispersed only in either the volatile organic solvent or the ionic liquid (C), respectively. It may be dissolved and / or dispersed in both the volatile organic solvent and the ionic liquid (C) in any ratio.
- a solution and / or dispersion obtained by dissolving and / or dispersing the organic photosensitizer molecule (A) and the organic light emitting molecule (B) in the ionic liquid (C) used in the method (II) is generally known.
- the organic photosensitizing molecule (A) and the organic light emitting molecule (B) can be produced by the method of dissolving and / or dispersing in the ionic liquid (C) using the above technique.
- other additives are mixed with the organic photosensitizer molecule (A) and the organic light emitting molecule (B) in the ionic liquid (C) using a generally known technique, and the solution is added. And / or a dispersion may be obtained.
- a known disperser such as an ultrasonic disperser, a bead mill, a homogenizer, a wet jet mill, a ball mill, an attritor, a sand mill, a roll mill, and a microwave disperser may be used alone or in combination.
- the organic photosensitizing molecule (A) and the organic light emitting molecule (B) may be finely pulverized and finely dispersed to obtain the solution and / or dispersion.
- the organic photosensitizer molecule (A) and the organic light emitting molecule (B) are dissolved and / or dispersed in a volatile organic solvent, and then the obtained solution and / or The dispersion is stirred and mixed with the ionic liquid (C) to produce a visually homogeneous and transparent solution and / or dispersion, and the trace amount of the volatile organic solvent is reduced from the solution and / or dispersion under reduced pressure.
- a method of removing up to In this method, a light wavelength conversion element in a state of being homogeneously and transparently mixed can be easily obtained, and a light wavelength conversion element having high stability and high light wavelength conversion efficiency can be obtained.
- the organic photosensitizing molecule (A) and This is more preferable as a method for obtaining a solution or dispersion obtained by dissolving and / or dispersing the organic light emitting molecule (B) in the ionic liquid (C).
- the volatile organic solvent used in the method (I) and the second method can dissolve and / or disperse the organic photosensitizing molecule (A) and the organic light emitting molecule (B), and is an ionic liquid.
- a volatile organic solvent that can be mixed homogeneously and transparently with (C) and can be removed to a trace amount under reduced pressure.
- the “trace amount” is an amount that can detect the volatile organic solvent mixed in the ionic liquid (C) only at a noise level or less based on the measurement of the light absorption spectrum.
- the volatile organic solvent is preferably a volatile organic solvent that can dissolve the organic photosensitizing molecule (A) and the organic light emitting molecule (B).
- the volatile organic solvent aromatic solvents such as toluene, benzene and xylene can be used.
- a volatile organic solvent capable of dissolving the organic photosensitizing molecule (A) and the organic light emitting molecule (B) is used, the volatile organic solvent matches the solubility of the organic photosensitizing molecule and the organic light emitting molecule. Can be selected as appropriate.
- stirring and mixing means in the method (I) and the second method known techniques such as ultrasonic waves, bubbling, agitator, liquid feed pump, pulverizer, bead mill, homogenizer, wet jet mill, microwave, etc.
- An apparatus can be used. These means may be used alone or in combination of two or more.
- the amount of gelling agent (D) used is usually less than that when an ionic gelling agent is used in order to achieve sufficient gelation.
- the content of the ionic liquid (C) when the entire light wavelength conversion element is 100 parts by mass is usually 10 parts by mass or more, and preferably 30 parts by mass or more.
- the nonionic polymer used in the method (I) is not particularly limited, but the organic photosensitizing molecule (A) and the organic light emitting molecule (B) are dissolved in the ionic liquid (C).
- a nonionic acrylic resin is preferable because it can easily swell after absorbing and / or dispersing the solution or dispersion.
- the nonionic acrylic resin is composed of a nonionic monomer composed mainly of (meth) acrylates ((meth) acrylic acid esters) such as methyl methacrylate, methyl acrylate, butyl acrylate, and hydroxyethyl methacrylate. It is a coalescence.
- (meth) acrylate means acrylate and / or methacrylate
- (meth) acryl means acryl and / or methacryl
- the nonionic polymer used in the method (I) may have any shape, for example, a film shape.
- the polymerizable compound used in the method (II) may be a compound capable of forming a nonionic polymer by a thermal polymerization reaction, or a compound capable of forming a nonionic polymer by a photopolymerization reaction. Also good.
- Examples of the compound capable of forming a nonionic polymer by the thermal polymerization reaction include nonionic (meth) acrylic esters such as methyl methacrylate, methyl acrylate, butyl acrylate, and hydroxyethyl methacrylate; acrylonitrile, methacrylate Nonionic (meth) acrylonitriles such as nitrile; Nonionic styrenes such as styrene, ⁇ -methylstyrene, p-methoxystyrene, p-cyanostyrene; Nonionic vinyl carboxylates such as vinyl acetate Nonionic chlorine-containing monomers such as vinyl chloride and vinylidene chloride; Nonionic (meth) acrylamides such as acrylamide; Nonionic fluorine-containing monomers such as tetrafluoroethylene; Methylvinyl Nonionic vinyl ketones such as ketones; Monomers such as olefins Ren and the like. These may
- a radical thermal polymerization initiator such as an azo compound or an organic peroxide is added to the compound capable of forming a nonionic polymer by the thermal polymerization reaction. And the thermal polymerization reaction of the compound may be performed.
- examples of the compound capable of forming a nonionic polymer by the thermal polymerization reaction include epoxy resins.
- the epoxy resins include an epoxy resin having an aliphatic cyclic structure, a bisphenol A type epoxy resin, and an aromatic polyfunctional epoxy resin having three or more epoxy groups in the molecule.
- the epoxy resins may be thermally cured using a basic curing agent such as an acid anhydride, an acid anhydride derivative, or an imidazole. In this method, a nonionic polymer with little coloration after curing can be obtained.
- Examples of the compound capable of forming a nonionic polymer by the photopolymerization reaction include monomers having a polymerizable group such as a vinyl group, a vinyl ether group, an allyl group, a maleimide group, and a (meth) acryloyl group. Among them, a monomer having a (meth) acryloyl group is preferable from the viewpoint of reactivity. Examples of the monomer having the (meth) acryloyl group include a monofunctional (meth) acrylate monomer having one (meth) acryloyl group in the structure; and a bifunctional having two (meth) acryloyl groups.
- (Meth) acrylate monomers such as a trifunctional or higher polyfunctional (meth) acrylate monomer having three or more acryloyl groups.
- (meth) acryloyl means acryloyl and / or methacryloyl.
- Examples of the monofunctional (meth) acrylate monomer include phenoxyethyl (meth) acrylate, phenyl (poly) ethoxy (meth) acrylate, p-cumylphenoxyethyl (meth) acrylate, tribromophenyloxyethyl (meth) ) Acrylate, phenylthioethyl (meth) acrylate, 2-hydroxy-3-phenyloxypropyl (meth) acrylate, phenylphenol (poly) ethoxy (meth) acrylate, phenylphenol epoxy (meth) acrylate, acryloylmorpholine, 2-hydroxy Propyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexane-1,4-dimethanol mono (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, Bornyl (meth) acrylate, dicyclopen
- bifunctional (meth) acrylate monomer examples include 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, Cyclodecane dimethanol di (meth) acrylate, bisphenol A polyethoxydi (meth) acrylate, bisphenol A polypropoxydi (meth) acrylate, bisphenol F polyethoxydi (meth) acrylate, ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) Acrylate, di (meth) acrylate of ⁇ -caprolactone adduct of neopentyl glycol hydroxybivalate (for example, KAYARAD (registered trademark) HX-220, KAYARAD (manufactured by Nippon Kayaku Co., Ltd.)) Trademark) HX-620, etc.) and
- trifunctional or higher polyfunctional (meth) acrylate monomer examples include tris (acryloxyethyl) isocyanurate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth).
- (meth) acrylate oligomers such as urethane (meth) acrylate, epoxy (meth) acrylate, and polyester (meth) acrylate can be used as the monomer having the (meth) acryloyl group. These may be used alone or in combination of two or more.
- a compound capable of forming a nonionic polymer by the photopolymerization reaction is added to a benzoin compound.
- one or more photopolymerization initiators such as acetophenones, anthraquinones, thioxanthones, ketals, benzophenones, and phosphine oxides are added, and the photopolymerization reaction of the compound is performed by irradiating with ultraviolet rays. Just do it.
- the light wavelength conversion element of the present invention preferably has a moisture content of 1% by mass or less, more preferably 0.1% by mass or less, and further preferably 0.01% by mass or less. Most preferably, it is 0.001 mass% or less. Thereby, the optical wavelength conversion element which has higher optical wavelength conversion efficiency is realizable.
- the light wavelength conversion element of the present invention preferably has an oxygen concentration of 100 ppm by mass or less, more preferably 10 ppm by mass or less, still more preferably 1 ppm by mass or less. Most preferably, it is 1 mass ppm or less. Thereby, the optical wavelength conversion element which has higher optical wavelength conversion efficiency is realizable.
- the light wavelength conversion element of the present invention if necessary, polymers such as acrylic polymer, polyester elastomer, urethane polymer, nitrile rubber, acrylic monomer (acrylic ester and / or methacrylic ester), and epoxy monomer Monomers such as, inorganic or organic light diffusing fillers and the like can also be added.
- a solvent can be added as necessary, but it is preferable not to add a solvent. Even when these components are added, the content of the ionic liquid (C) with respect to 100 parts by mass of the light wavelength conversion element is usually 10 parts by mass or more.
- the light wavelength conversion element of the present invention is a visually homogeneous and transparent solution and / or dispersion, and also has good stability.
- the light wavelength conversion element of the present invention can be used for solar cells, photocatalysts, photocatalytic hydrogen / oxygen generators, optical up-conversion filters, and the like.
- the solar cell of the present invention uses the light wavelength conversion element of the present invention.
- a solar cell according to an example of the present invention includes a photoelectric conversion layer (solar cell layer) 1 and a strip-shaped light receiving surface electrode disposed on a light incident side surface of the photoelectric conversion layer 1. 7, a transparent back electrode 2 laminated on the back surface of the light incident side of the photoelectric conversion layer 1, a transparent insulating film 3 laminated on the back surface of the light incident side of the transparent back electrode 2, and transparent The up-conversion layer 4 using the light wavelength conversion element of the present invention laminated on the back surface of the light incident side surface of the insulating film 3 and the back conversion surface of the up-conversion layer 4 on the light incident side surface. And a light reflecting film 5.
- the photoelectric conversion layer 1 is not particularly limited, and an organic photoelectric conversion layer such as a dye-sensitized solar cell or an organic thin film solar cell, a compound semiconductor photoelectric conversion layer, a silicon photoelectric conversion layer, or the like is used. it can.
- an organic photoelectric conversion layer such as a dye-sensitized solar cell or an organic thin film solar cell, a compound semiconductor photoelectric conversion layer, a silicon photoelectric conversion layer, or the like is used. it can.
- the light-receiving surface electrode 7 and the light reflection film 5 can be formed of a metal such as Ag, Al, Ti, Cr, Mo, W, Ni, or Cu.
- the transparent back electrode 2 can be formed of a transparent conductor such as ITO (indium tin oxide), SnO 2 , or ZnO.
- the transparent insulating film 3 can be formed of a resin such as polyethylene terephthalate, polycarbonate, polyimide resin, acrylic resin, and polyether nitrile.
- the up-conversion layer 4 may be formed of a cell and an optical wavelength conversion element enclosed in the cell, as in the optical up-conversion filter of the present invention described later, and is formed only of the optical wavelength conversion element. May be.
- a sealing member such as a sealing resin at the periphery thereof. Good.
- the up-conversion layer 4 up-converts incident light 6 from the sun (converts it into light having a shorter wavelength), so that the intensity of light in a wavelength range that the photoelectric conversion layer 1 can use for power generation.
- the power generation efficiency of the solar cell can be further increased.
- the up-conversion layer 4 is disposed between the transparent insulating film 3 and the light reflecting film 5, but the arrangement position of the up-conversion layer 4 is arranged on the light incident side of the light receiving surface electrode 7 or the like. You may change into other arrangement positions like. In that case, a transparent insulating film may be provided between the up-conversion layer 4 and the light-receiving surface electrode 7.
- the light receiving surface electrode 7 may be replaced with a transparent electrode formed on the entire light incident side surface of the photoelectric conversion layer 1.
- the transparent insulating film 3 may be omitted.
- the transparent insulating film 3 is replaced with the light wavelength conversion element and the transparent back electrode in order to avoid contact between the light wavelength conversion element and the transparent back electrode 2. 2 is preferable.
- the transparent back electrode 2 is used as a light reflecting electrode.
- the light reflecting film 5 may be omitted.
- the photocatalyst of the present invention uses the light wavelength conversion element of the present invention.
- a photocatalyst with high catalyst efficiency is realized by arranging a photocatalyst layer in place of the light-receiving surface electrode 7, the photoelectric conversion layer 1, the transparent back electrode 2, and the transparent insulating film 3 in the solar cell of FIG. Can do.
- the photocatalyst according to an example of the present invention contains a glass channel in which water 10 (photocatalyst layer) to which a photocatalyst is added is accommodated and gas 9 is filled in a space other than the water 10 to which the photocatalyst is added.
- the upconversion layer 4 formed on the side surface and the bottom surface of the glass channel 8
- the light reflecting film 5 formed on the outer surface of the upconversion layer 4
- the light reflecting film 5 And a mechanical support 11 formed on the outer surface of the light reflecting film 5.
- the conversion efficiency of the photocatalyst can be further increased by increasing the light intensity.
- the photocatalytic hydrogen / oxygen generator of the present invention uses the light wavelength conversion element of the present invention.
- the photoelectric conversion layer 1, the transparent back electrode 2, and the transparent insulating film 3 in the solar cell of FIG. -An oxygen generator can be realized.
- the optical up-conversion filter of the present invention is an optical up-conversion filter that converts light into light having a shorter wavelength, and includes the optical wavelength conversion element and a cell, and the optical wavelength conversion element includes the oxygen It is enclosed in the cell in a state where the concentration is 100 mass ppm or less.
- the cell is not particularly limited as long as it is a cell that can transmit light.
- two glass plates made of quartz glass, borosilicate glass, etc. are overlapped and their peripheral portions are fused.
- a cell having a bonded structure can be used.
- the light wavelength conversion element is preferably enclosed in the cell with an oxygen concentration of 100 mass ppm or less, more preferably encapsulated in the cell in a state of 10 mass ppm or less. More preferably, it is enclosed in the cell in a state of 1 mass ppm or less, and most preferably, it is enclosed in the cell in a state of 0.1 mass ppm or less.
- the oxygen concentration is kept low. As a result, it is possible to realize an optical up-conversion filter that stably exhibits high light wavelength conversion efficiency that can be applied even to light having a weak sunlight intensity.
- the optical up-conversion filter is obtained by, for example, injecting a light wavelength conversion element into a cell, performing deoxygenation treatment until the oxygen concentration becomes 100 mass ppm or less as necessary, and then sealing the cell.
- the deoxygenation method includes, for example, a method in which a light wavelength conversion element is decompressed using a vacuum pump such as a rotary pump or a turbo molecular pump, and an inert gas such as nitrogen gas or argon gas is used in the light wavelength conversion element. And a method in which the light wavelength conversion element is frozen and then decompressed (vacuum degassing) using a vacuum pump (freezing vacuum degassing method).
- the optical upconversion filter can be used as the upconversion layer 4 of the solar cell, photocatalyst, or photocatalytic hydrogen / oxygen generator.
- an oxygen getter is used to reduce the oxygen concentration of the light wavelength conversion element. You may coexist.
- a water absorbing material is used to reduce the oxygen concentration of the light wavelength conversion element. May coexist.
- Example 1 (Production of optical wavelength conversion element) 1-butyl-2,3-dimethylimidazolium bis (trifluoromethylsulfonyl) imide (CAS number), which is a non-water-miscible ionic liquid (C), in a glass vial with an internal volume of about 8 ml at room temperature. 350493-08-2, manufacturer: IoLiTech Ionic Liquids Technologies GmbH, hereinafter referred to as “ionic liquid # 1”) was added in an amount of 400 ⁇ l.
- ionic liquid # 1 IoLiTech Ionic Liquids Technologies GmbH
- naphthalene (CAS number: 91-20-3, manufacturer: Sigma-Aldrich Co. LLC) as an organic light-emitting molecule (B) was added to this liquid (a visually homogeneous and transparent single layer solution and / or dispersion).
- naphthalene (CAS number: 91-20-3, manufacturer: Sigma-Aldrich Co. LLC) as an organic light-emitting molecule (B) was added to this liquid (a visually homogeneous and transparent single layer solution and / or dispersion).
- luminanaphthalene (CAS number: 91-20-3, manufacturer: Sigma-Aldrich Co. LLC) as an organic light-emitting molecule (B) was added to this liquid (a visually homogeneous and transparent single layer solution and / or dispersion).
- luminescent molecule # 1 was added about 200 ⁇ l of a stock solution in which methanol was dissolved at a concentration of 2 ⁇ 10 ⁇ 2 M, and a visually inhomogeneous mixed liquid was
- this mixture liquid is repeatedly sucked and spouted using a glass Pasteur pipette (same as previously used) to obtain a single layer liquid mixture that is visually homogeneous and transparent. It was. Immediately thereafter, the glass vial was capped, and the mixture was stirred and homogenized for about 7 minutes with an ultrasonic bath sonicator (same as previously used). Then, as before, remove the glass vial lid, place the glass vial in a vacuum container, and vacuum at room temperature for about 2 hours using a scroll pump (same as previously used). It was. As a result, methanol as a volatile component was removed to a trace amount or less, and a visually homogeneous and transparent one-layer solution and / or dispersion (liquid) was obtained.
- This up-conversion light emission evaluation sample is fixed to a dedicated sample holder, and the continuous light laser emission emitted from a continuous light laser emitter (manufacturer: World Star Technologies Inc., model number: TECBL-30GC-405) as excitation light.
- a continuous light laser emitter manufactured by World Star Technologies Inc., model number: TECBL-30GC-405
- continuous light laser emission # 1 the light emitted from the sample is converted into parallel light by a condensing lens arranged in a direction perpendicular to the incident excitation light, and then converted into a spectroscope (manufacturer: Roper Scientific GmbH, model number: SP-2300i) by another lens.
- the light emission spectrum (spectral shape and intensity) by an electronically cooled silicon CCD (Charge Coupled Device) detector (manufacturer: Roper Scientific GmbH, model number: Pixis100BR) was measured.
- CCD Charge Coupled Device
- FIG. 3 shows the change in emission spectrum when the power (excitation intensity) of continuous light laser emission # 1 irradiated on the sample is changed between 0.25 mW, 0.5 mW, 1 mW, 2 mW, 4 mW, 8 mW and 16 mW. Is shown.
- Example 2 In Example 1, instead of ionic liquid # 1, 1-butyl-1-methylpyrrolidinium bis (trifluoromethylsulfonyl) imide (CAS number: 2234437-11) which is a non-water-miscible ionic liquid (C) 4.
- a light wavelength conversion element was prepared and evaluated in exactly the same procedure as in Example 1 except that the manufacturer: Merck KGaA (hereinafter referred to as “ionic liquid # 2”) was used. The results shown in FIG. The light emission maximum wavelength of the light wavelength conversion element was 315.9 nm, 321.0 nm, 330.8 nm, 335.4 nm). This is the same as the result shown in FIG.
- FIG. 6 shows a light absorption spectrum of the light wavelength conversion element measured with an ultraviolet-visible-near infrared spectrophotometer (in the light wavelength conversion element, 10-methyl as an organic photosensitizer molecule (A)). The longest absorption maximum wavelength derived from -9-acridone was 400 nm).
- Example 3 In the preparation procedure of the light wavelength conversion element of Example 1, ionic liquid # 2 was used instead of ionic liquid # 1, and 1-cyanonaphthalene (CAS number: 86) was used instead of luminescent molecule # 1 as the organic luminescent molecule (B). -53-3, manufacturer: Sigma-Aldrich Co. LLC (hereinafter referred to as “luminescent molecule # 2”) was used to produce a light wavelength conversion element in the same procedure as in Example 1.
- FIG. 8 shows a light absorption spectrum of the light wavelength conversion element measured by an ultraviolet-visible-near infrared spectrophotometer (in the light wavelength conversion element, 10-methyl as an organic photosensitizer molecule (A)).
- the absorption maximum wavelength of the longest wavelength derived from -9-acridone was 400.5 nm).
- Example 4 In the procedure for producing the light wavelength conversion element of Example 1, ionic liquid # 2 was used instead of ionic liquid # 1, and 2-methoxynaphthalene (CAS number: 93) was used instead of luminescent molecule # 1 as the organic luminescent molecule (B). -04-9, manufacturer: Tokyo Chemical Industry Co., Ltd.) was used to produce a light wavelength conversion element in the same procedure as in Example 1.
- FIG. 10 shows a light absorption spectrum of the light wavelength conversion element measured by an ultraviolet visible near infrared spectrophotometer (in the light wavelength conversion element, 10-methyl as an organic photosensitizer molecule (A)). The absorption maximum wavelength of the longest wavelength derived from -9-acridone was 400.5 nm).
- Example 5 In the preparation procedure of the light wavelength conversion element of Example 1, ionic liquid # 2 was used instead of ionic liquid # 1, and “stock solution in which sensitizing molecule # 1 was dissolved in toluene at a concentration of 4 ⁇ 10 ⁇ 3 M” was used. Instead of adding “about 20 ⁇ l”, the concentration of 2,4-diethylthioxanthone (CAS number: 82799, manufacturer: Nippon Kayaku Co., Ltd.) as an organic photosensitizer molecule (A) in methanol is 2 ⁇ 10 ⁇ 3 M.
- a light wavelength conversion element was prepared in the same procedure as in Example 1 except that about 80 ⁇ l of the stock solution dissolved in (1) was added.
- FIG. 12 shows a light absorption spectrum of the light wavelength conversion element measured by an ultraviolet visible near infrared spectrophotometer (in the light wavelength conversion element, 2, 4 as the organic photosensitizing molecule (A)). The longest absorption maximum wavelength derived from diethylthioxanthone was 387 nm).
- Example 6 In Example 5, a light wavelength conversion element was prepared in the same procedure as in Example 5 except that luminescent molecule # 2 was used instead of luminescent molecule # 1.
- this optical wavelength conversion element was irradiated with continuous light laser emission # 1 with a power of 5 mW and measured in the same procedure as the evaluation procedure for the optical wavelength conversion element described in Example 1, the upconversion shown in FIG. An emission spectrum (the emission maximum wavelength of the light wavelength conversion element: 331.2 nm, 338.4 nm) was observed.
- FIG. 14 shows a light absorption spectrum of the light wavelength conversion element measured by an ultraviolet-visible-near infrared spectrophotometer (in the light wavelength conversion element, 2, 4 as the organic photosensitizing molecule (A)). -The longest wavelength absorption maximum wavelength derived from diethylthioxanthone was 388 nm).
- Example 7 In the preparation procedure of the light wavelength conversion element of Example 1, ionic liquid # 2 was used instead of ionic liquid # 1, and “stock solution in which sensitizing molecule # 1 was dissolved in toluene at a concentration of 4 ⁇ 10 ⁇ 3 M” was used.
- FIG. 16 shows a light absorption spectrum of the light wavelength conversion element measured by an ultraviolet visible near infrared spectrophotometer (in the light wavelength conversion element, 10-methyl as an organic photosensitizer molecule (A)). The absorption maximum wavelength of the longest wavelength derived from -9-acridone was 400.5 nm).
- Example 8 As ionic liquid (C), purified and pre-dried methyltri-n-octylammonium bis (trifluoromethylsulfonyl) imide (CAS number: 375395-33-8, manufacturer: Merck KGaA) is used instead of ionic liquid # 1.
- the produced light wavelength conversion element was poured into a quartz tube with one end of 1 mm square inside a glove box in an argon atmosphere, and the open end of the quartz tube was sealed with solder.
- the concentration of sensitizing molecule # 1 in the present light wavelength conversion element is 1.33 ⁇ 10 ⁇ 4 M, and the concentration of luminescent molecule # 1 in the present light wavelength conversion element is 1.5 ⁇ 10 ⁇ 2 M. .
- Example 9 Instead of “100 ⁇ l of stock solution in which luminescent molecule # 1 was dissolved in methanol at a concentration of 6.0 ⁇ 10 ⁇ 2 M”, “1-dodecylnaphthalene (CAS number: 38641-16-) as organic luminescent molecule (B)” 6) was dissolved in toluene at a concentration of 1.33 ⁇ 10 ⁇ 1 M stock solution ”, and the second evacuation time was changed to 3 hours. An optical wavelength conversion element was produced.
- the produced light wavelength conversion element was poured into a quartz tube with one end of 1 mm square inside a glove box in an argon atmosphere, and the open end of the quartz tube was sealed with solder.
- the concentration of sensitizing molecule # 1 in the present light wavelength conversion element is 1.33 ⁇ 10 ⁇ 4 M, and the concentration of 1-dodecylnaphthalene in the present light wavelength conversion element is 1.0 ⁇ 10 ⁇ 2 M. .
- the optical wavelength conversion element of Example 8 and Example 9 was irradiated with continuous light laser emission # 1 with an excitation intensity (power) of 3 mW, and the same procedure as the evaluation procedure for the optical wavelength conversion element described in Example 1 was used. When the measurement was performed, an upconversion emission spectrum shown in FIG. 17 was observed.
- the light wavelength conversion element using 1-dodecylnaphthalene as the organic light emitting molecule (B) is much more than the excitation wavelength of 405 nm, similarly to the light wavelength conversion element using naphthalene as the organic light emitting molecule (B). It was found that remarkable up-conversion emission was observed in the short wavelength ultraviolet region (in this case, the ultraviolet region centered at about 320 to 360 nm). Further, from comparison between Example 8 and Example 9, the light wavelength conversion element using 1-dodecylnaphthalene as the organic light emitting molecule (B) is the light wavelength conversion element using naphthalene as the organic light emitting molecule (B). It was found that the emission intensity was higher than that in comparison.
- Example 10 In the preparation procedure of the light wavelength conversion element of Example 1, instead of “about 20 ⁇ l of a stock solution in which sensitizing molecule # 1 was dissolved in toluene at a concentration of 4 ⁇ 10 ⁇ 3 M”, “sensitizing molecule # 1 was added to toluene concentration 1.0 ⁇ 10 -3 with stock solution 53 ⁇ l "dissolved in M in, instead of the" luminescent molecule # stock solution of about 200 ⁇ l dissolved at a concentration of 2 ⁇ 10 -2 M to 1 in methanol " Using 40 ⁇ l of a stock solution in which 1-methylnaphthalene as an organic light emitting molecule (B) is dissolved in methanol at a concentration of 5.0 ⁇ 10 ⁇ 2 M, stirring and homogenization twice with an ultrasonic bath sonicator The light wavelength conversion element was produced in the same procedure as in Example 1 except that the processing time was changed to 5 minutes and evacuation was performed in the pass box of the glove box.
- the produced light wavelength conversion element was poured into a quartz tube with one end of 1 mm square inside a glove box in an argon atmosphere, and the open end of the quartz tube was sealed with solder.
- the concentration of sensitizing molecule # 1 in the present light wavelength conversion element is 1.33 ⁇ 10 ⁇ 4 M, and the concentration of 1-methylnaphthalene in the present light wavelength conversion element is 5.0 ⁇ 10 ⁇ 3 M. .
- the optical wavelength conversion element of this example was irradiated with continuous light laser emission # 1 having an excitation intensity (power) of 3 mW, and measurement was performed in the same procedure as the evaluation procedure for the optical wavelength conversion element described in Example 1. However, the upconversion emission spectrum shown in FIG. 18 was observed. Further, FIG. 19 shows a light absorption spectrum of the light wavelength conversion element measured by an ultraviolet visible near infrared spectrophotometer.
- the light wavelength conversion element using 1-methylnaphthalene as the organic light emitting molecule (B) is also in the ultraviolet region having a wavelength much shorter than the excitation wavelength of 405 nm (in this case, the ultraviolet region centered at about 320 to 350 nm). ) Showed significant up-conversion emission.
- Example 11 Instead of “40 ⁇ l of a stock solution in which 1-methylnaphthalene as an organic light emitting molecule (B) is dissolved in methanol at a concentration of 5.0 ⁇ 10 ⁇ 2 M”, “acenaphthene as an organic light emitting molecule (B) in methanol The light wavelength conversion element was prepared in the same procedure as in Example 10 except that 40 ⁇ l of a stock solution dissolved in 5.0 ⁇ 10 ⁇ 2 M was used.
- the produced light wavelength conversion element was poured into a quartz tube with one end of 1 mm square inside a glove box in an argon atmosphere, and the open end of the quartz tube was sealed with solder.
- the concentration of sensitizing molecule # 1 in the present light wavelength conversion element is 1.33 ⁇ 10 ⁇ 4 M, and the concentration of acenaphthene in the present light wavelength conversion element is 5.0 ⁇ 10 ⁇ 3 M.
- the optical wavelength conversion element of this example was irradiated with continuous light laser emission # 1 having an excitation intensity (power) of 3 mW, and measurement was performed in the same procedure as the evaluation procedure for the optical wavelength conversion element described in Example 1. However, an upconversion emission spectrum shown in FIG. 20 was observed.
- FIG. 21 shows a light absorption spectrum of the light wavelength conversion element measured with an ultraviolet-visible-near infrared spectrophotometer.
- the light wavelength conversion element using acenaphthene as the organic light emitting molecule (B) is also in the ultraviolet region far shorter than the excitation wavelength of 405 nm (in this case, the ultraviolet region centered at about 320 to 350 nm), It was found that it showed remarkable upconversion luminescence.
- Example 12 Instead of “40 ⁇ l of a stock solution in which 1-methylnaphthalene as an organic luminescent molecule (B) is dissolved in methanol at a concentration of 5.0 ⁇ 10 ⁇ 2 M”, “p-terphenyl as an organic luminescent molecule (B)” was used in the same procedure as in Example 10 except that a stock solution (133 ⁇ l) dissolved in toluene at a concentration of 1.5 ⁇ 10 ⁇ 2 M ”was used.
- the produced light wavelength conversion element was poured into a quartz tube with one end of 1 mm square inside a glove box in an argon atmosphere, and the open end of the quartz tube was sealed with solder.
- the concentration of sensitizing molecule # 1 in the present light wavelength conversion element is 1.33 ⁇ 10 ⁇ 4 M, and the concentration of p-terphenyl in the present light wavelength conversion element is 5.0 ⁇ 10 ⁇ 3 M. .
- the optical wavelength conversion element of this example was irradiated with continuous light laser emission # 1 having an excitation intensity (power) of 3 mW, and measurement was performed in the same procedure as the evaluation procedure for the optical wavelength conversion element described in Example 1. However, an upconversion emission spectrum shown in FIG. 22 was observed.
- FIG. 23 shows a light absorption spectrum of the light wavelength conversion element measured with an ultraviolet-visible-near infrared spectrophotometer.
- the light wavelength conversion element using p-terphenyl as the organic light emitting molecule (B) is also in the ultraviolet region having a wavelength much shorter than the excitation wavelength of 405 nm (in this case, the ultraviolet region centered at about 320 to 360 nm). ) Showed significant up-conversion emission.
- a compound represented by the formula: poly [(dimethylimino) hexane-1,6-diyl (dimethylimino) methylene-1,4-phenylenecarbonyliminotrans-cyclohexane-1,4-diyliminocarbonyl-1,4-phenylene Methylenebis (trifluoromethanesulfonyl) amide] (hereinafter referred to as “ionic gelling agent # 1”) was synthesized. The degree of polymerization n of the obtained ionic gelling agent # 1 is about 62 converted from the weight average molecular weight. The resulting ionic gelling agent # 1 was identified by the following NMR spectrum.
- Example 13 (Preparation of mixture of gelling agent (D) and ionic liquid (C)) First, 48 mg of the ionic gelling agent # 1 obtained in Synthesis Example 1 of the gelling agent (D) was placed in a washed glass vial (with an internal volume of 8 mL), and 150 ⁇ l of methanol was added dropwise thereto. . Next, the lid of the vial was closed and the vial was heated on a hot plate set at 80 ° C. for 20 minutes. Next, 400 ⁇ l of purified ionic liquid # 1 was added to the vial.
- the contents of the vial were mixed uniformly by repeatedly “sucking / discharging” using a glass Pasteur pipette (the same as that used in Example 1), and then the vial The lid was closed, and ultrasonic dispersion was performed for 15 minutes using an ultrasonic bath sonicator (same as that used in Example 1). The vial was then heated on a hot plate set at 80 ° C. for 10 minutes. Subsequently, the lid was removed from the vial, and the vial was placed in a vacuum drying oven (manufacturer: Yamato Scientific Co., Ltd., model number: ADP200) and heated in a vacuum at 90 ° C. for 2 hours.
- a vacuum drying oven manufactured by a vacuum drying oven
- the temperature of the vial was lowered to 80 ° C. and then removed from the vacuum drying oven.
- the lid of the vial was closed, and the vial was stored overnight in the dark and allowed to cool.
- a mixture of the gelling agent (D) and the ionic liquid (C) a mixture of the ionic gelling agent # 1 and the ionic liquid # 1 having a concentration of the ionic gelling agent # 1 of 120 g / L. (Gel; hereinafter referred to as “gel stock”).
- sample solution As an ionic liquid solution of the organic photosensitizer molecule (A), the organic light emitting molecule (B), and the gelling agent (D), the sensitizing molecule # 1, the light emitting molecule # 1, and the ionic gelling agent # 1 ionic liquid solution (hereinafter referred to as “sample solution”) was obtained.
- the vial containing the sample solution was placed on a hot plate set at 80 ° C. and heated for 10 minutes in the main box of the glove box under an argon atmosphere.
- a part of the sample solution in the vial is injected into a 2 mm square closed end quartz tube using a syringe with an injection needle, The open end of the quartz tube was sealed with solder in the box and left for about 1 day. The next day, it was confirmed that the sample solution in the quartz tube was gelled.
- the concentration of the sensitizing molecule # 1 in the present light wavelength conversion element is 1.33 ⁇ 10 ⁇ 4
- the concentration of the luminescent molecule # 1 in the present light wavelength conversion element is 1.5 ⁇ 10 ⁇ 2.
- the concentration of the ionic gelling agent # 1 in the light wavelength conversion element is 7 g / L.
- the light wavelength conversion element containing the gelling agent (D) is also in the ultraviolet region (in this case) much shorter than the excitation wavelength of 405 nm, as is the case with the light wavelength conversion element not containing the gelling agent (D). In the ultraviolet region centered at about 320 to 350 nm, up-conversion emission was found.
- a light wavelength conversion element was obtained in the same procedure as in Example 13 except that the heating temperature was changed to 70 ° C.
- the concentration of sensitizing molecule # 1 in the present light wavelength conversion element is 1.33 ⁇ 10 ⁇ 4 M, and the concentration of luminescent molecule # 2 in the present light wavelength conversion element is 1.5 ⁇ 10 ⁇ 2 M.
- the concentration of the ionic gelling agent # 1 in the light wavelength conversion element is 7 g / L.
- the light wavelength conversion element of this example was irradiated with continuous light laser emission # 1 with excitation intensity of 3 mW and continuous light laser emission # 1 with excitation intensity of 6 mW, respectively, and the evaluation procedure for the light wavelength conversion element described in Example 1 As a result of the measurement, the up-conversion emission spectrum shown in FIGS. 25 and 26 was observed.
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Abstract
Description
で表される化合物が挙げられる。ここで、「水素原子を含む任意の置換基」とは、水素原子、又は水素原子を除く任意の置換基を意味する。
で表される化合物が挙げられる。前記一般式(2)で表される化合物において、R12~R19がそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アルコキシ基、シアノ基、ニトロ基、アリール基、またはヘテロアリール基であり、前記一般式(2)のR20が、水素原子、アルキル基、アルケニル基、アルキニル基、複素環基、アルキルアリール基、アリール基、またはヘテロアリール基であることが好ましい。
で表される化合物が好ましい。
で表される化合物が好ましい。さらに、前記一般式(4)で表される化合物において、R12~R19がそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アルコキシ基、シアノ基、ニトロ基、アリール基、またはヘテロアリール基であることが好ましい。
で表される化合物が挙げられる。
で表される化合物が挙げられる。
で表されるΔETが、有機光増感分子(A)と有機発光分子(B)との任意の組み合わせについて、好ましくは-0.5eV以上2.0eV以下であり、より好ましくは-0.3eV以上1.0eV以下であり、さらに好ましくは-0.2eV以上0.5eV以下であり、特に好ましくは-0.1eV以上0.3eV以下である。1eVとは、電子1個を1Vの電位差で加速したときに電子が得るエネルギーである。
で表される化合物が好ましい。
で表される化合物、下記一般式
で表される化合物、下記一般式
で表される化合物等が挙げられる。
(1)有機光増感分子(A)をイオン液体(C)中に溶解および/または分散させてなる第1の溶液および/または分散液と、有機発光分子(B)をイオン液体(C)中に溶解および/または分散させてなる第2の溶液および/または分散液と、イオン性ゲル化剤とイオン液体(C)との混合物を揮発性有機溶媒に溶解させてなる液体状の混合物(溶液)とを用意し、前記第1の溶液および/または分散液に対して、前記第2の溶液および/または分散液と、前記液体状の混合物とを混合した後、揮発性有機溶媒を留去する方法、
(2)有機光増感分子(A)および有機発光分子(B)をイオン液体(C)中に溶解および/または分散させてなる溶液および/または分散液を、イオン性ゲル化剤とイオン液体(C)との混合物(溶液又はゲル)に対して混合する方法、
(3)有機光増感分子(A)および有機発光分子(B)をイオン液体(C)中に溶解および/または分散させてなる溶液および/または分散液を、イオン性ゲル化剤を揮発性有機溶媒に溶解させてなる溶液と混合した後、揮発性有機溶媒を留去する方法、
等の方法を用いて製造することができる。
(光波長変換要素の作製)
室温下で、内容積約8mlのガラスバイアル瓶内に、非水混和性のイオン液体(C)である1-ブチル-2,3-ジメチルイミダゾリウムビス(トリフルオロメチルスルホニル)イミド(CAS番号:350493-08-2、製造元:IoLiTec Ionic Liquids Technologies GmbH、以下「イオン液体#1」と称する)を400μl入れた。続いて、このイオン液体#1に、有機光増感分子(A)としての10-メチル-9-アクリドン(CAS番号:719-54-0、製造元:東京化成工業株式会社、以下「増感分子#1」と称する)をトルエン中に濃度4×10-3Mで溶解させたストック溶液を約20μl加えたところ、目視で不均質な混合液体が得られた。この混合液体に対し、特許文献3に記載した方法と同様に、ガラス製パスツールピペット(製造元:Fisher Scientific Inc.、製品番号:5-5351-01)を用いて「吸い・吐き」を繰り返し行うことにより、目視で均質かつ透明な一層の混合液を得た。そしてその直後、そのガラスバイアル瓶に蓋をして、その混合液を超音波バスソニケーター(製造元:Branson Ultrasonics Corp.、型番:Model3510)にて約7分間撹拌および均質化処理を行った。続いて、ガラスバイアル瓶の蓋を除き、ガラスバイアル瓶を真空容器内に入れ、室温下でスクロールポンプ(製造元:エドワーズ株式会社、型番:XDS35i、設計到達圧力:1Pa以下)を用いて約1時間真空引きを行った。その結果、揮発分であるトルエンは痕跡量以下まで除去され、目視上均質かつ透明な一層の溶液および/または分散体(液体)が得られた。
続いて、当該液体(光波長変換要素としての目視上均質かつ透明な液体)の一部を、不活性なアルゴンガスで満たされたグローブボックス中で、特許文献3に記載した方法と同様に、内寸1mm×1mm、外寸2mm×2mm、長さ約25mmの片端閉じ正方形石英管内にその全長の3/4程度、注入し、石英管の開口端を鉛ハンダで封止して、当該石英管に密閉されたアップコンバージョン発光評価用試料を得た。
実施例1において、イオン液体#1の代わりに非水混和性のイオン液体(C)である1-ブチル-1-メチルピロリジニウムビス(トリフルオロメチルスルホニル)イミド(CAS番号:223437-11-4、製造元:Merck KGaA、以下「イオン液体#2」と称する)を用いた他は、実施例1と全く同じ手順で光波長変換要素の作製および評価を行ったところ、図5に示す結果(光波長変換要素の発光極大波長:315.9nm、321.0nm、330.8nm、335.4nm)を得た。これは、性質が異なるイオン液体を用いたことに起因してアップコンバージョン発光スペクトルの形状が若干異なること以外は、図3に示した結果と同様であり、本発明がイオン液体の種類に依らず実施可能であることを確認した。また、図6に、紫外可視近赤外分光光度計により測定した、当該光波長変換要素の光吸収スペクトルを示す(当該光波長変換要素において、有機光増感分子(A)としての10-メチル-9-アクリドン由来の最長波長の吸収極大波長は400nmであった)。
実施例1の光波長変換要素の作製手順において、イオン液体#1の代わりにイオン液体#2を用い、有機発光分子(B)として発光分子#1の代わりに1-シアノナフタレン(CAS番号:86-53-3、製造元:Sigma-Aldrich Co. LLC、以下「発光分子#2」と称する)を用いた以外は実施例1と同じ手順で光波長変換要素の作製を行った。
実施例1の光波長変換要素の作製手順において、イオン液体#1の代わりにイオン液体#2を用い、有機発光分子(B)として発光分子#1の代わりに2-メトキシナフタレン(CAS番号:93-04-9、製造元:東京化成工業株式会社)を用いた以外は実施例1と同じ手順で光波長変換要素の作製を行った。
実施例1の光波長変換要素の作製手順において、イオン液体#1の代わりにイオン液体#2を用い、「増感分子#1をトルエン中に濃度4×10-3Mで溶解させたストック溶液約20μl」を加えた代わりに「有機光増感分子(A)としての2,4-ジエチルチオキサントン(CAS番号:82799、製造元:日本化薬株式会社)をメタノール中に濃度2×10-3Mで溶解させたストック溶液約80μl」を加えた以外は実施例1と同じ手順で光波長変換要素の作製を行った。
実施例5において、発光分子#1の代わりに発光分子#2を用いた以外は実施例5と同じ手順で光波長変換要素の作製を行った。この光波長変換要素に対し、パワー5mWの連続光レーザー発光#1を照射し、実施例1に記載した光波長変換要素の評価手順と同じ手順で計測を行ったところ、図13に示すアップコンバージョン発光スペクトル(光波長変換要素の発光極大波長:331.2nm、338.4nm)が観測された。また、図14に、紫外可視近赤外分光光度計により測定した、当該光波長変換要素の光吸収スペクトルを示す(当該光波長変換要素において、有機光増感分子(A)としての2,4-ジエチルチオキサントン由来の最長波長の吸収極大波長は388nmであった)。
実施例1の光波長変換要素の作製手順において、イオン液体#1の代わりにイオン液体#2を用い、「増感分子#1をトルエン中に濃度4×10-3Mで溶解させたストック溶液約20μl」を加えた代わりに「増感分子#1をトルエン中に濃度1×10-3Mで溶解させたストック溶液約50μl」を加え、「発光分子#1をメタノール中に濃度2×10-2Mで溶解させたストック溶液約200μl」を加えた代わりに「有機発光分子(B)としての2-シアノナフタレン(CAS番号:613-46-7、製造元:東京化成工業株式会社)をメタノール中に濃度1×10-2Mで溶解させたストック溶液約120μl」を加えた以外は実施例1と同じ手順で光波長変換要素の作製を行った。
イオン液体(C)として、イオン液体#1の代わりに精製および予備乾燥したメチルトリ-n-オクチルアンモニウムビス(トリフルオロメチルスルホニル)イミド(CAS番号:375395-33-8、製造元:Merck KGaA)を用い、「増感分子#1をトルエン中に濃度4×10-3Mで溶解させたストック溶液約20μl」の代わりに「増感分子#1をトルエン中に濃度1×10-3Mで溶解させたストック溶液60μl」を用い、「発光分子#1をメタノール中に濃度2×10-2Mで溶解させたストック溶液約200μl」の代わりに「発光分子#1をメタノール中に濃度6.0×10-2Mで溶解させたストック溶液100μl」を用い、超音波バスソニケーターによる2回の撹拌および均質化処理の時間を何れも5分間に変更し、真空引きをグローブボックスのパスボックス内で行った以外は、実施例1と同じ手順で、光波長変換要素を作製した。
「発光分子#1をメタノール中に濃度6.0×10-2Mで溶解させたストック溶液100μl」の代わりに「有機発光分子(B)としての1-ドデシルナフタレン(CAS番号:38641-16-6)をトルエン中に濃度1.33×10-1Mで溶解させたストック溶液30μl」を用い、2回目の真空引きの時間を3時間に変更した以外は、実施例8と同じ手順で、光波長変換要素を作製した。
実施例1の光波長変換要素の作製手順において、「増感分子#1をトルエン中に濃度4×10-3Mで溶解させたストック溶液約20μl」の代わりに「増感分子#1をトルエン中に濃度1.0×10-3Mで溶解させたストック溶液53μl」を用い、「発光分子#1をメタノール中に濃度2×10-2Mで溶解させたストック溶液約200μl」の代わりに「有機発光分子(B)としての1-メチルナフタレンをメタノール中に濃度5.0×10-2Mで溶解させたストック溶液40μl」を用い、超音波バスソニケーターによる2回の撹拌および均質化処理の時間を何れも5分間に変更し、真空引きをグローブボックスのパスボックス内で行った以外は、実施例1と同じ手順で、光波長変換要素を作製した。
「有機発光分子(B)としての1-メチルナフタレンをメタノール中に濃度5.0×10-2Mで溶解させたストック溶液40μl」の代わりに「有機発光分子(B)としてのアセナフテンをメタノール中に濃度5.0×10-2Mで溶解させたストック溶液40μl」を用いた以外は、実施例10と同じ手順で、光波長変換要素を作製した。
「有機発光分子(B)としての1-メチルナフタレンをメタノール中に濃度5.0×10-2Mで溶解させたストック溶液40μl」の代わりに「有機発光分子(B)としてのp-ターフェニルをトルエン中に濃度1.5×10-2Mで溶解させたストック溶液133μl」を用いた以外は、実施例10と同じ手順で、光波長変換要素を作製した。
Jun'ichi Nagasawa, et al., ACS Macro Lett., 2012, 1 (9), p. 1108-1112に記載の方法で、イオン性ゲル化剤であるゲル化剤(D)として、下記式
〔実施例13〕
(ゲル化剤(D)およびイオン液体(C)の混合物の調製)
まず、洗浄済のガラス製のバイアル瓶(内容量8mL)内に、ゲル化剤(D)の合成例1で得られたイオン性ゲル化剤♯1を48mg入れ、そこにメタノール150μlを滴下した。次に、バイアル瓶の蓋を閉め、バイアル瓶を80℃に設定されたホットプレート上で20分間加熱した。次に、バイアル瓶内に、精製済みのイオン液体#1を400μl加えた。その後すぐに、バイアル瓶の内容物を、ガラス製のパスツールピペット(実施例1で使用したものと同じ)を用いて「吸い・吐き」を繰り返し行うことにより均一に混和させた後、バイアル瓶の蓋を閉め、超音波バスソニケーター(実施例1で使用したものと同じ)を用いて15分間超音波分散を行った。次に、バイアル瓶を80℃に設定されたホットプレート上で10分間加熱した。続いて、バイアル瓶から蓋を外し、バイアル瓶を真空乾燥オーブン(製造元:ヤマト科学株式会社、型番:ADP200)に入れて90℃で2時間真空加熱した。バイアル瓶を80℃まで降温させてから真空乾燥オーブンから取り出し、バイアル瓶の蓋を閉め、暗所にて一晩保存し放冷した。これにより、ゲル化剤(D)とイオン液体(C)との混合物として、イオン性ゲル化剤♯1の濃度が120g/Lであるイオン性ゲル化剤♯1とイオン液体#1との混合物(ゲル;以下、「ゲルストック」と呼ぶ)を得た。
バイアル瓶内のゲルストックから別のバイアル瓶に250μlを分取し、メタノール250μl(イオン液体#1:メタノール=1:1(体積比))をゲルストックに滴下した。滴下後すぐに、ゲルが溶解し、ゲルストックは液体状となった。その後、バイアル瓶の蓋を閉め、超音波バスソニケーター(実施例1で使用したものと同じ)を用いて10分間超音波分散を行うことにより、液体状のゲルストックの均一性を高めた。これにより、イオン性ゲル化剤♯1の濃度が60g/Lである、均一性の高い液体状のゲルストックが得られた。
洗浄済のガラス製のバイアル瓶(容量8mL)に、イオン液体(C)としての精製済みのイオン液体#1を565μl入れ、有機光増感分子(A)としての増感分子#1のトルエン溶液(濃度1×10-3M)80μlを加えた。次に、バイアル瓶の内容物を、ガラス製のパスツールピペット(実施例1で使用したものと同じ)を用いて「吸い・吐き」を繰り返し行うことにより均一に混和させた後、バイアル瓶の蓋を閉め、超音波バスソニケーター(実施例1で使用したものと同じ)を用いて5分間超音波分散を行った。次に、このバイアル瓶から蓋を外し、その直後にこのバイアル瓶をグローブボックスのパスボックス内に入れ、パスボックス中でスクロールポンプ(実施例1で使用したものと同じ)を用いて1時間真空引きすることによりトルエンを除去した後、バイアル瓶をグローブボックスから取り出した。これにより、有機光増感分子(A)のイオン液体溶液として、増感分子#1のイオン液体溶液を得た。
バイアル瓶内の増感分子#1のイオン液体溶液に対して、有機発光分子(B)としての発光分子#1のメタノール溶液(濃度6.0×10-2M)150μlと、液体状のゲルストック70μl(メタノールおよびイオン液体#1をそれぞれ35μlずつ含む)とを加えた。次に、バイアル瓶の内容物を、ガラス製のパスツールピペット(実施例1で使用したものと同じ)を用いて「吸い・吐き」を繰り返し行うことにより均一に混和させた後、バイアル瓶の蓋を閉め、超音波バスソニケーター(実施例1で使用したものと同じ)を用いて5分間超音波分散を行った。次に、このバイアル瓶から蓋を外し、その直後にこのバイアル瓶をグローブボックスのパスボックス内に入れ、パスボックス中でスクロールポンプ(実施例1で使用したものと同じ)を用いて2時間真空引きすることにより、メタノールを除去した。次に、バイアル瓶をグローブボックスのメインボックスに移動させた後、アルゴン雰囲気下でバイアル瓶の蓋を閉めた。これにより、有機光増感分子(A)、有機発光分子(B)、およびゲル化剤(D)のイオン液体溶液として、増感分子#1、発光分子#1、およびイオン性ゲル化剤♯1のイオン液体溶液(以下、「試料溶液」と呼ぶ)を得た。
試料溶液が入ったバイアル瓶を、80℃に設定されたホットプレート上に置き、アルゴン雰囲気下のグローブボックスのメインボックス内で10分間加熱した。次に、アルゴン雰囲気下のグローブボックスのメインボックス内でバイアル瓶内の試料溶液の一部を注射針のついた注射器を用いて内寸2mm角の片端閉じ石英管に注入し、グローブボックスのメインボックス内で石英管の開口端をハンダで封止し、約1日間放置した。翌日、石英管内の試料溶液がゲル化していることが確認された。
(液体状のゲルストックの作製)
洗浄済のガラス製のバイアル瓶(内容量8mL)内に、イオン液体(C)としての精製済みのイオン液体#1を400μlと、メタノール400μl(イオン液体#1:メタノール=1:1(体積比))とを入れ、ゲル化剤(D)の合成例1で得られたイオン性ゲル化剤♯1を20mg添加した。バイアル瓶の蓋を固く閉め、超音波バスソニケーター(実施例1で使用したものと同じ)を用いて30分間超音波分散を行った。これにより、イオン液体#1とメタノールとの混合溶液中にイオン性ゲル化剤♯1が目視で均一に混和し、イオン性ゲル化剤♯1の濃度が25g/Lである、無色透明の液体状のゲルストックが得られた。
イオン液体#1の使用量を344μlに変更し、増感分子#1のトルエン溶液(濃度1×10-3M)の使用量を53μlに変更した以外は、実施例13と同じ手順で、増感分子#1のイオン液体溶液を調製した。
有機発光分子(B)としての発光分子#1のメタノール溶液(濃度6.0×10-2M)150μlの代わりに発光分子#2(1-シアノナフタレン)のメタノール溶液(濃度6.0×10-2M)100μlを用い、実施例13の手順で作製した液体状のゲルストック70μlの代わりに本実施例の手順で作製した液体状のゲルストック112μl(メタノールおよびイオン液体#1をそれぞれ56μlずつ含む)を用いた以外は、実施例13と同じ手順で、増感分子#1、発光分子#2、およびイオン性ゲル化剤♯1のイオン液体溶液を得た。
加熱温度を70℃に変更したこと以外は実施例13と同じ手順で、光波長変換要素を得た。本光波長変換要素中の増感分子#1の濃度は1.33×10-4Mであり、本光波長変換要素中の発光分子#2の濃度は1.5×10-2Mであり、本光波長変換要素中のイオン性ゲル化剤♯1の濃度は7g/Lである。
2 透明背面電極
3 透明絶縁膜
4 アップコンバージョン層
5 光反射膜
7 受光面電極
8 ガラスチャネル
9 ガス
10 光触媒が添加された水
11 機械的支持体
Claims (16)
- 三重項-三重項消滅過程を示す組み合わせである有機光増感分子(A)および有機発光分子(B)を、イオン液体(C)中に溶解および/または分散させてなる、目視上均質かつ透明な光波長変換要素であって、
前記有機光増感分子(A)の吸収極大波長(ただし、複数の吸収極大波長が存在する場合には、それらの中で最長波長の吸収極大波長)が、250~499nmの範囲内にあることを特徴とする光波長変換要素。 - 前記光波長変換要素からの発光極大波長が、400nm以下の範囲内にあることを特徴とする請求項1に記載の光波長変換要素。
- 前記一般式(1)のXがチオ基であり、R1~R8がそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アルコキシ基、シアノ基、ニトロ基、アリール基、またはヘテロアリール基であることを特徴とする請求項3に記載の光波長変換要素。
- 前記一般式(2)のR12~R19がそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アルコキシ基、シアノ基、ニトロ基、アリール基、またはヘテロアリール基であり、前記一般式(2)のR20が、水素原子、アルキル基、アルケニル基、アルキニル基、複素環基、アルキルアリール基、アリール基、またはヘテロアリール基であることを特徴とする請求項5に記載の光波長変換要素。
- 前記一般式(6)のR33~R42がそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アルコキシ基、シアノ基、ニトロ基、アリール基、またはヘテロアリール基であることを特徴とする請求項7に記載の光波長変換要素。
- ゲル化剤(D)をさらに含むことを特徴とする請求項1~8のいずれか一項に記載の光波長変換要素。
- ゲル状態となっていることを特徴とする請求項9に記載の光波長変換要素。
- 前記ゲル化剤(D)は、イオン性ゲル化剤であることを特徴とする請求項9又は10に記載の光波長変換要素。
- 前記ゲル化剤(D)は、非イオン性重合体であることを特徴とする請求項9又は10に記載の光波長変換要素。
- 請求項1~12のいずれか一項に記載の光波長変換要素を用いた太陽電池。
- 請求項1~12のいずれか一項に記載の光波長変換要素を用いた光触媒。
- 請求項1~12のいずれか一項に記載の光波長変換要素を用いた光触媒型水素・酸素発生装置。
- 光をより短い波長の光に変換する光アップコンバージョンフィルターであって、
請求項1~12のいずれか一項に記載の光波長変換要素と、
セルとを備え、
前記光波長変換要素が、前記セル中に封入されていることを特徴とする光アップコンバージョンフィルター。
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2015163676A (ja) * | 2014-01-31 | 2015-09-10 | 日本化薬株式会社 | イオン液体を含む光波長変換要素およびその光波長変換要素を含む物品 |
JP2018180277A (ja) * | 2017-04-13 | 2018-11-15 | 国立大学法人東京工業大学 | 深共晶溶媒を含む光波長変換要素およびその光波長変換要素を含む物品 |
JP2018194684A (ja) * | 2017-05-17 | 2018-12-06 | 国立大学法人東京工業大学 | 光アップコンバージョンフィルムおよび光アップコンバージョンフィルムを用いた物品 |
JP2019199582A (ja) * | 2018-05-18 | 2019-11-21 | 国立大学法人東京工業大学 | 光波長変換要素およびその光波長変換要素を含む物品 |
JP7054090B2 (ja) | 2018-05-18 | 2022-04-13 | 国立大学法人東京工業大学 | 光波長変換要素およびその光波長変換要素を含む物品 |
WO2022021662A1 (zh) * | 2020-07-28 | 2022-02-03 | 苏州科技大学 | 氮杂蒽衍生物上转换体系及其制备方法与应用 |
US11827610B2 (en) | 2021-09-15 | 2023-11-28 | Enko Chem, Inc. | Protoporphyrinogen oxidase inhibitors |
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JPWO2015115556A1 (ja) | 2017-03-23 |
CN105940083A (zh) | 2016-09-14 |
US20170084758A1 (en) | 2017-03-23 |
JP6436356B2 (ja) | 2018-12-12 |
US10175557B2 (en) | 2019-01-08 |
CN105940083B (zh) | 2019-06-11 |
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