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WO2021188762A1 - Composés émissifs cycliques contenant du bore et film de conversion de couleur les contenant - Google Patents

Composés émissifs cycliques contenant du bore et film de conversion de couleur les contenant Download PDF

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Publication number
WO2021188762A1
WO2021188762A1 PCT/US2021/022900 US2021022900W WO2021188762A1 WO 2021188762 A1 WO2021188762 A1 WO 2021188762A1 US 2021022900 W US2021022900 W US 2021022900W WO 2021188762 A1 WO2021188762 A1 WO 2021188762A1
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Prior art keywords
mmol
color conversion
alkyl
added
photoluminescent
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English (en)
Inventor
Shijun Zheng
Jeffrey R. Hammaker
Hiep Luu
Jan SASKA
Ozair Siddiqui
Peng Wang
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Nitto Denko Corp
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Nitto Denko Corp
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Priority to CN202180022500.3A priority Critical patent/CN115335488A/zh
Priority to KR1020227032539A priority patent/KR102818945B1/ko
Priority to JP2022555947A priority patent/JP7458498B2/ja
Publication of WO2021188762A1 publication Critical patent/WO2021188762A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • G02F1/01—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 for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—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 for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/1336—Illuminating devices
    • G02F1/133614—Illuminating devices using photoluminescence, e.g. phosphors illuminated by UV or blue light
    • 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
    • G02F1/01—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 for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—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 for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/1336—Illuminating devices
    • G02F1/133624—Illuminating devices characterised by their spectral emissions

Definitions

  • the gamut is a certain complete subset of colors available on a device such as a television or monitor.
  • a device such as a television or monitor.
  • RGB Red Green Blue
  • a wide-gamut color space achieved by using pure spectral primary colors
  • a device which could provide a wider gamut could enable the display to portray more vibrant colors.
  • high-definition large screen displays become more common, the demand for higher performance, slimmer and highly functional displays has increased.
  • LEDs Current light emitting diodes
  • a blue light source exciting a green phosphor, a red phosphor, or a yellow phosphor to obtain a white light source.
  • FWHM full width half maximum
  • the full width half maximum (FWHM) of the emission peak of the current green and red phosphors are quite large, usually greater than 40 nm, resulting in the green and red color spectrums overlapping and rendering colors that are not fully distinguishable from one another. This overlap leads to poor color rendition and the deterioration of the color gamut.
  • methods have been developed using films containing quantum dots in combination with LEDs.
  • quantum dots there are problems with the use of quantum dots.
  • cadmium-based quantum dots are extremely toxic and are banned from use in many countries due to health safety issues.
  • non-cadmium-based quantum dots have a very low efficiency in converting blue LED light to green and red light.
  • quantum dots require expensive encapsulating processes for protection against moisture and oxygen.
  • the cost of using quantum dots is high, because of the difficulties in controlling size uniformity during the production process.
  • SUMMARY Photoluminescent complexes described herein may be used to improve the contrast between distinguishable colors in televisions, computer monitors, smart devices and any other device that utilizes color displays.
  • the photoluminescent complexes of the present disclosure provide a novel color converting dye complex with good blue light absorbance and narrow emissions bandwidths, with the full width half maximum [FWHM] of emission band of less than 40 nm.
  • a photoluminescent complex absorbs light of a first wavelength and emits light of a second higher wavelength than the first wavelength.
  • the photoluminescent complexes disclosed herein may be utilized with a color conversion film for use in light emitting apparatuses.
  • the color conversion films of the present disclosure reduce color deterioration by reducing overlap within the color spectrum resulting in high quality color rendition.
  • Some embodiments include a photoluminescent complex, comprising a blue light absorbing azole derivative, a linker group (such as a linker group comprising an unsubstituted ester or a substituted ester), and a boron-dipyrromethene (BODIPY) moiety.
  • the linker group may covalently link the azole derivative to the BODIPY moiety.
  • the azole derivative absorbs light of a first excitation wavelength and transfers an energy to the BODIPY moiety.
  • the BODIPY moiety absorbs the energy from the azole derivative and emits a light energy of a second higher wavelength.
  • the photoluminescent complex has an emission quantum yield greater than 70%. In some embodiments, the photoluminescent complex may have an emission band with a full width half maximum [FWHM] of up to 40 nm. In some embodiments, the photoluminescent complex may have a Stokes shift, the difference between the excitation peak of the blue light absorbing moiety and the emission peak of the BODIPY moiety, of equal to or greater than 45 nm.
  • the azole derivative may be of the following general formula:
  • Z may be a nitrogen (NR 10 ). In some embodiments, Z may be sulfur (S). In some embodiments, Z may be oxygen (O).
  • R 9 may be H or a linker (such as an unsubstituted ester linker group or a substituted ester linker group).
  • R 10 may be H, a substituted aryl, or a linker group (such as an unsubstituted ester linker group or a substituted ester linker group).
  • the BODIPY derivative may be of the following general formula: Wherein R 1 -R 8 are as described in greater detail below, and L represents a linker group, such as a linker group comprising an unsubstituted ester or a substituted ester.
  • Some embodiments include a color conversion film, comprising a color conversion layer; wherein the color conversion layer includes a resin matrix; and a photoluminescent complex described herein dispersed within the resin matrix.
  • the color conversion film may comprise a thickness between 1 ⁇ m to about 200 ⁇ m.
  • the color conversion film of the present disclosure may absorb blue light in the 400 nm to about 480 nm range and emit light in the 510 nm to about 560 nm wavelength range.
  • Another embodiment describes a color conversion film that may absorb blue light in the 400 nm to about 480 nm range and emit light in the 575 nm to about 645 nm wavelength range.
  • the color conversion film may further comprise a transparent substrate layer.
  • the transparent substrate layer comprises two opposing surfaces, wherein the color conversion layer is disposed on one of the opposing surfaces.
  • Some embodiments include a method for preparing the color conversion film, the method comprises: dissolving at least one of the aforedescribed photoluminescent complex and a binder resin within a solvent; and applying the mixture on one of the transparent substrates opposing surfaces.
  • Some embodiments include a backlight unit including a color conversion film described herein.
  • Other embodiments include a display device including the backlight unit described herein.
  • FIG.2 is a graph depicting the absorption and emission spectra of one embodiment of a photoluminescent complex, PLC-5.
  • the current disclosure describes photoluminescent complexes and their uses in color conversion films.
  • the photoluminescent complexes may be used to improve and enhance the transmission of one or more desired emissive bandwidths within a color conversion film.
  • the photoluminescent complex may both enhance the transmission of a desired first emissive bandwidth and decrease the transmission of a second emissive bandwidth.
  • a color conversion film may enhance the contrast or intensity between two or more colors, increasing the distinction from one another.
  • the present disclosure describes photoluminescent complexes that may enhance the contrast or intensity between two colors, increasing their distinction from one another.
  • substituted group is derived from the unsubstituted parent structure wherein one or more hydrogen atoms on the parent structure have been independently replaced by one or more substituent groups.
  • the substituent groups may be independently selected from an optionally substituted alkyl, alkenyl, ketone, aryl, or a C 3 -C 7 heteroalkyl.
  • An alkyl, alkenyl, or alkynyl moiety, whether saturated or unsaturated, may be branched, straight chain, or cyclic.
  • the alkyl moiety may have 1 to 6 carbon atoms (whether it appears herein, a numerical range such as “1 to 6” refers to each integer in the given range: e.g., “1 to 6 carbon atoms” means that the alkyl group may have 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to and including 6 carbon atoms, although the present definition also covers the occurrence of the term “alkyl” where no numerical range is designated.
  • the alkyl group of the compounds designated herein may be designated as “C 1 -C 6 alkyl” or similar designations.
  • C 1 -C 6 alkyl indicates that there are one to six carbon atoms in the alkyl chain, i.e., the alkyl chain is selected from among methyl, ethyl, propyl, iso-propyl, n- butyl, iso-butyl, sec-butyl, and t-butyl.
  • C 1 -C6 alkyl includes C 1 -C 2 alkyl, C 1 -C3 alkyl, C 1 -C 4 alkyl, C 1 -C 5 alkyl.
  • Alkyl groups may be substituted or unsubstituted.
  • Typical alkyl groups include, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
  • Typical alkenyl groups include ethenyl, propenyl, butenyl, etc.
  • heteroalkyl refers to an alkyl group, as defined herein, in which one or more of the constituent carbon atoms have been replaced by a nitrogen, oxygen, or sulphur.
  • Examples include but are not limited to, -CH 2 -O-CH 3 , -CH 2 -CH 2 -O-CH 3 , -CH 2 -NH- CH 3 , -CH 2 -N(CH 3 )-CH 3 , -CH 2 -CH 2 -NH-CH 3 , -CH 2 -CH 2 -N(CH 3 )-CH 3 , -CH 2 -S-CH 2 -CH 3 , -CH 2 -CH 2 - S(O)-CH 3 .
  • up to two heteroatoms may be consecutive, such as, by way of example, -CH 2 -NH-O-CH 3 , etc.
  • aromatic refers to a planar ring having a delocalized ⁇ -electron system containing 4n+2 ⁇ electrons, where n is an integer. Aromatic rings may be formed from five, six, seven, eight, nine, or more than nine atoms. Aromatics may be optionally substituted.
  • aromatic includes both carbocyclic aryl (e.g., phenyl) and heterocyclic aryl (or “heteroaryl” or heteroaromatic”) group (e.g., pyridine).
  • the term includes monocyclic or fused-ring polycyclic (i.e., rings which share adjacent pairs of carbon atoms) groups.
  • hydrocarbon ring refers to a monocyclic or polycyclic radial that contains only carbon and hydrogen and may be saturated.
  • Monocyclic hydrocarbon rings include groups having from 3 to 12 carbon atoms.
  • Illustrative examples of monocyclic groups include the following moieties: and the like.
  • polycyclic groups include the following moieties: bicyclooctane], bicyclopentane], [bicycloheptane], [bicycloheptane], bicyclodecane], [decahydronaphthalene], octahydropentalene], [octahydroindene], [hexahydroindene], [1,2,3,4-tetrahydronaphthalene], [2,3-dihydro-1H-indene], [1,1-dimethyl-2,3-dihydro-1H-indene], [2’,3’- dihydrospiro[cyclopentane-1,1’-indene], or 1,2,3,3a- tetrahydropentalene].
  • aryl as used herein means an aromatic ring wherein each of the atoms forming the ring is a carbon atom.
  • Aryl rings may be formed by five, six, seven, eight, or more than eight carbon atoms.
  • Aryl groups may be substituted or unsubstituted. Examples of aryl groups include, but are not limited to phenyl, naphthalenyl, phenanthrenyl, etc.
  • aralkyl refers to an alkyl radical, as defined herein, substituted with an aryl, as defined herein. Non-limiting aralkyl groups include benzyl, phenethyl; and the like.
  • heteroaryl refers to an aryl group that includes one or more ring heteroatoms selected from nitrogen, oxygen, and sulfur, wherein the heteroaryl group has from 4 to 10 atoms in its ring system and with the proviso that the ring of the group does not contain two adjacent oxygen, or sulfur atoms. It is understood that the heteroaryl ring may have additional heteroatoms in the ring. In heteroaryls that have two or more heteroatoms, those two or more heteroatoms may be the same or different from one another. Heteroaryls may be optionally substituted.
  • An N-containing heteroaryl moiety refers to an aryl group in which at least one of the skeletal atoms of the ring is a nitrogen atom.
  • heteroaryl groups include the following moieties: pyrrole, imidazole, pyridine, etc.
  • halogen as used herein means fluorine, chlorine, bromine, and iodine
  • bond means a chemical bond between two atoms or to two moieties when the atoms joined by the bond are considered to be part of a larger structure.
  • moiety refers to a specific segment or functional group of a molecule. Chemical moieties are often recognized chemical entities embedded in or appended to a molecule.
  • cyano or “nitrile” as used herein refers to any organic compound that contains a -CN functional group.
  • ester refers to a chemical moiety with the formula -COOR, where R is selected from among alkyl, cycloalkyl, aryl, heteroaryl (bonded through a ring carbon) and heterocyclic (bonded through a ring carbon). Any hydroxy, or carboxyl side chain on the compounds described herein may be esterified. Any suitable method may be used to prepare such esters and may readily be found in conventional reference sources.
  • ether refers to a chemical moiety that contains an oxygen atom connected to two alkyl or aryl groups with the general formula of R-O-R’, where the term alkyl and aryl is as defined herein.
  • azole or “azole derivative” as used herein, refers to a chemical moiety with the formula: .
  • BODIPY refers to a chemical moiety with the formula:
  • the BODIPY moiety may be composed or dipyrromethene complexed with a di- substituted boron atom, typically a BF2 unit.
  • the IUPAC name for the BODIPY core is 4,4- difluoro-4-bora-3a,4a-diaza-s-indacene.
  • Use of the term “may” or “may be” should be construed as shorthand for “is” or “is not” or, alternatively, “does” or “does not” or “will” or “will not,” etc.
  • the statement “the distance separating the blue light absorbing azole derivative and the BODIPY moiety may be about 8 ⁇ or greater” should be interpreted as, for example, “In some embodiments, the distance separating the blue light absorbing azole derivative and the BODIPY moiety is about 8 ⁇ or greater,” or “In some embodiments, the distance separating the blue light absorbing azole derivative and the BODIPY moiety is not about 8 ⁇ or greater.”
  • the present disclosure relates to photoluminescent complexes that absorb light energy of first wavelength and emit light energy in a second higher wavelength.
  • the photoluminescent complex of the present disclosure comprises an absorbing luminescent moiety and an emitting luminescent moiety that are coupled through a linker such that their distance is tuned for the absorbing luminescent moiety to transfer its energy to the acceptor luminescent moiety, wherein the acceptor luminescent moiety then emits out at a second wavelength that is larger than the absorbed first wavelength.
  • a photoluminescent complex of the present disclosure comprises: a blue light absorbing azole derivative; a linker group; and a boron-dipyrromethene (BODIPY) moiety.
  • the linker group may covalently link the azole derivative to the BODIPY moiety.
  • the azole derivative absorbs light of a first excitation wavelength and transfers energy to the BODIPY moiety, the BODIPY moiety then emits a light energy of a second wavelength, wherein the light energy of the second wavelength is higher than the first wavelength.
  • FRET Forster resonance energy transfer
  • the photoluminescent complex may have a high emission quantum yield.
  • the emission quantum yield may be greater than 15%, greater than 20%, greater than 25%, greater than 30%, greater than 35%, greater than 40%, greater than 45%, greater than 50%, greater than 55%, greater than 60%, greater than 65%, greater than 70%, greater than 75%, greater than 80%, greater than 85%, greater than 90%, or greater than 95%; and/or up to 100%.
  • Emission quantum yield may be measured by dividing the number of photons emitted by the number of photons absorbed, which is equivalent to the emission efficiency of the luminescent moiety.
  • the absorbing luminescent moiety may have an emission quantum yield greater than 80%.
  • the quantum yield may be greater than 0.8 (80%), 0.81 (81%), 0.82 (82%), 0.83 (83%), 0.84 (84%), 0.85 (85%), 0.86 (86%), 0.87 (87%), 0.88 (88%), 0.89 (89%), 0.9 (90%), 0.91 (91%), 0.92 (92%), 0.93 (93%), 0.94 (94%), or 0.95 (95%); and/or up to 1 (100%).
  • Quantum yield measurements in film may be made by a spectrophotometer, e.g., Quantaurus-QY spectrophotometer (Humamatsu, Inc., Campbell, CA, USA).
  • the photoluminescent complex has an emission band which may have a full width half maximum (FWHM) of less than 40 nm.
  • the FWHM is the width of the emission band in nanometers at the emission intensity that is half of the maximum emission intensity for the band.
  • the photoluminescent complex has an emission band FWHM value that is less than or equal to about 35 nm, less than or equal to about 30 nm, less than or equal about 25 nm, or less than or equal to about 20 nm.
  • the photoluminescent complex may have a Stokes shift that is equal to or greater than 45 nm. As used herein the term “Stokes shift” means the distance between the excitation peak of the blue light absorbing moiety and the emission peak of the BODIPY moiety.
  • the photoluminescent complex of the current disclosure may have a tunable emission wavelength.
  • Different substitution patterns on the BODIPY moiety may tune the emission wavelength, e.g. the maximum emission wavelength or peak emission wavelength, to between 510 nm to about 560 nm, or between about 610 nm to about 645 nm, or any wavelength in a range bounded by any of these values.
  • the blue light absorbing moiety may have a peak absorption maximum between about 400 nm to about 470 nm wavelength.
  • the peak absorption may be between about 400 nm to about 405 nm, about 405 nm to about 410 nm, about 410 nm to about 415 nm, about 415 nm to about 420 nm, about 420 nm to about 425 nm, about 425 nm to about 430 nm, about 430 nm to about 435 nm, about 435 nm, to about 440 nm, about 440 nm to about 445 nm, about 445 nm, to about 450 nm, about 450 nm to about 455 nm, about 455 nm to about 460 nm, about 460 nm to about 465 nm, about 465 nm to about 470 nm, or any wavelength in a range bounded by any of these values.
  • the photoluminescent complex may have an emission peak between 510 nm and 560 nm.
  • the emission peak may be between about 510 nm to about 515 nm, about 515 nm to about 520 nm, about 520 nm to about 525 nm, about 525 nm to about 530 nm, about 530 nm to about 535 nm, about 535 nm to about 540 nm, about 540 nm to about 545 nm, about 545 nm to about 550 nm, about 550 nm to about 555 nm, about 555 nm to about 560 nm, or any wavelength in a range bounded by any of these values.
  • the photoluminescent complex may have an emission peak between 610 nm to 645 nm.
  • the emission peak may be between 610 nm to about 615 nm, about 615 nm to about 620 nm, about 620 nm to about 625 nm, about 625 nm to about 630 nm, about 630 nm to about 635 nm, about 635 nm to about 640 nm, about 640 nm to about 645 nm, or any wavelength in a range bounded by any of these values.
  • photoluminescent complex wherein the blue light absorbing azole derivative and the BODIPY moiety’s spatial distance is adjusted through the linker group, for transfer of the blue light absorbing azole derivative’s energy to the BODIPY moiety.
  • the present disclosure describes a photoluminescent complex, wherein the photoluminescent complex may comprise a blue light absorbing azole derivative, a linker group and a BODIPY moiety. The linker group covalently links the blue light absorbing azole derivative and the BODIPY moiety.
  • the azole derivative absorbs light energy of a first excitation wavelength and transfers an energy to the BODIPY moiety, wherein the BODIPY moiety absorbs the energy from the azole derivative and emits a light energy of a second higher wavelength.
  • the photoluminescent complex has an emission quantum yield that is 70-100%.
  • Some embodiments include a blue light absorbing azole derivative of the following general formula: , wherein Z may be selected from NR 10 , S, or O; R 9 is a H or a substituted ester linker; and R 10 is H, a substituted aryl, or a substituted ester linker.
  • Z is S.
  • Z is O.
  • Z is NR 10 .
  • R 10 is H.
  • R 10 is a substituted aryl.
  • R 10 is a substituted phenyl.
  • R 10 is fluorophenyl, such as .
  • R 10 is the linker group, such as a substituted ester linker group.
  • the azole derivative may be a compound wherein Z may be NR 10 , R 9 may be H, and R 10 may be an unsubstituted ester linker group.
  • the azole derivative may be a compound wherein Z may be NR 10 , R 9 may be H, and R 10 may a substituted ester linker group.
  • the azole derivative may be a compound wherein Z may be NR 10 , R 9 may be an unsubstituted ester linker, R 10 may a substituted aryl.
  • the azole derivative the azole derivative may be a compound wherein Z may be a S, and R 9 may be a substituted ester linker.
  • Z is NR 10
  • R 10 is a substituted aryl, wherein the substituted aryl may be selected from the following structure: .
  • the linker group covalently links the blue absorbing azole derivative with the BODIPY moiety.
  • the linker group may be varied to adjust the spatial distance between the blue light absorbing azole derivative and the BODIPY moiety.
  • L may represent the linker group.
  • the linker group, e.g. L may comprise a substituted ester linker group.
  • the substituted ester linker may comprise one of the following structures: .
  • the linker group, e.g. L may comprise an unsubstituted ester linker group.
  • the unsubstituted ester linker may comprise one of the following structures:
  • the photoluminescent complex of the current disclosure may comprise a BODIPY moiety.
  • R 1 may be H, alkyl, alkenyl, alkynyl, or an alkoxy-3-oxypropen-1-yl.
  • R 1 is H.
  • R 1 is alkyl, such as C 1-6 alkyl (e.g. methyl, ethyl, propyl, isopropyl,C 4 alkyl,C 5 alkyl, or C 6 alkyl).
  • R 1 is alkenyl, such as C 2-6 alkenyl (e.g. ethenyl, propenyl, C 4 alkenyl, C 5 alkenyl, C 6 alkenyl).
  • R 1 is alkynyl, such as C 2-6 alkynyl (e.g. ethynyl, propynyl, C 4 alkynyl, C 5 alkynyl, C 6 alkynyl).
  • R 1 is an alkoxy-3-oxypropen-1-yl, e some embodiments, R 1 is methoxy-3-oxypropen-1-yl, e some embodiments, R 1 is ethyoxy-3-oxypropen-1-yl, e some embodiments, R 1 is propoxy-3-oxypropen-1-yl.
  • Other alkoxy groups are also envisioned for the alkoxy-3-oxy-propen-1yl esters of R 1 .
  • R 6 may be H, alkyl, alkenyl, alkynyl, or an alkoxy- 3-oxypropen-1-yl. In some embodiments, R 6 is H. In some embodiments, R 6 is alkyl, such as C 1-6 alkyl (e.g. methyl, ethyl, propyl, isopropyl, C 4 alkyl, C 5 alkyl, or C 6 alkyl). In some embodiments, R 6 is alkenyl, such as C 2-6 alkenyl (e.g. ethenyl, propenyl, C 4 alkenyl, C 5 alkenyl, C 6 alkenyl).
  • C 1-6 alkyl e.g. methyl, ethyl, propyl, isopropyl, C 4 alkyl, C 5 alkyl, or C 6 alkyl.
  • R 6 is alkenyl, such as C 2-6 alkenyl (e.g. ethenyl, propeny
  • R 6 is alkynyl, such as C 2-6 alkynyl (e.g. ethynyl, propynyl, C 4 alkynyl, C 5 alkynyl, C 6 alkynyl).
  • R 6 is an alkoxy-3-oxypropen-1-yl, such as methoxy-3-oxypropen-1-yl, ethyoxy-3-oxypropen-1-yl, propoxy-3-oxypropen-1-yl, etc.
  • R 6 is ethoxy-3-oxypropen-1-yl.
  • R 3 may be H or alkyl, such as C 1-6 alkyl or C 1 -C 2 alkyl.
  • R 3 is H. In some embodiments, R 3 is C 1 -C 2 alkyl. In some embodiments, R 3 is methyl.
  • R 4 may be H or alkyl, such as C 1-6 alkyl or C 1 -C 2 alkyl. In some embodiments, R 4 is H. In some embodiments, R 4 is C 1 -C 2 alkyl. In some embodiments, R 4 is methyl.
  • R 2 may be H, alkyl, alkenyl, alkynyl, -CN, an alkyl ester (e.g., -C(O)OCH 2 CH 3 ), or an aryl ester (e.g., -COOCH 2 Ar). In some embodiments, R 2 is H.
  • R 2 is alkyl, such as C 1-6 alkyl (e.g. methyl, ethyl, propyl, isopropyl, C 4 alkyl, C 5 alkyl, or C 6 alkyl).
  • R 2 is alkenyl, such as C 2-6 alkenyl (e.g. ethenyl, propenyl, C 4 alkenyl, C 5 alkenyl, C 6 alkenyl).
  • R 2 is alkynyl, such as C 2-6 alkynyl (e.g. ethynyl, propynyl, C 4 alkynyl, C 5 alkynyl, C 6 alkynyl).
  • R 2 is -CN. In some embodiments, R 2 is an alkyl ester (e.g., -C(O)OCH 2 CH 3 ) . In some embodiments, R 2 is an aryl ester (e.g., - COOCH 2 Ar).
  • R 5 may be H, alkyl, alkenyl, alkynyl, -CN, an alkyl ester (e.g., -C(O)OCH 2 CH 3 ), or an aryl ester (e.g., -COOCH 2 Ar). In some embodiments, R 5 is H. In some embodiments, R 5 is alkyl, such as C 1-6 alkyl (e.g.
  • R 5 is alkenyl, such as C 2-6 alkenyl (e.g. ethenyl, propenyl, C 4 alkenyl, C 5 alkenyl, C 6 alkenyl).
  • R 5 is alkynyl, such as C 2-6 alkynyl (e.g. ethynyl, propynyl, C 4 alkynyl, C 5 alkynyl, C 6 alkynyl).
  • R 5 is -CN.
  • R 5 is an alkyl ester (e.g., -C(O)OCH 2 CH 3 ) .
  • R 5 is an aryl ester (e.g., - COOCH 2 Ar).
  • R 2 and R 3 may link together to form an additional monocyclic hydrocarbon ring structure, or a polycyclic hydrocarbon ring structure;
  • R 4 and R 5 may link together to form an additional monocyclic hydrocarbon ring structure, or a polycyclic hydrocarbon ring structure;
  • R 7 may be H or alkyl, such as C 1-6 alkyl (e.g. methyl, ethyl, propyl, isopropyl, C 4 alkyl, C 5 alkyl, or C 6 alkyl).
  • R 7 is H. In some embodiments, R 7 is methyl (- CH 3 ).
  • R 8 may be H or alkyl, such as C 1-6 alkyl (e.g. methyl, ethyl, propyl, isopropyl, C 4 alkyl, C 5 alkyl, or C 6 alkyl). In some embodiments, R 8 is H. In some embodiments, R 8 is methyl (- CH 3 ). L is the linker group, such as a substituted ester linker group. In some embodiments, R 7 and R 8 are methyl. In some embodiments, R 1 , R 3 , R 4 , and R 6 are C 1 -C 2 alkyl.
  • R 1 , R 3 , R 4 , and R 6 are methyl. In some embodiments, R 1 and R 6 are: In some examples, The BODIPY moiety of the present disclosure may be a BODIPY moiety wherein R 1 , R 3 , R 4 and R 6 are each a methyl; R 2 and R 5 are a cyano group; R 7 and R 8 are each a methyl; and L comprises a linker group.
  • the BODIPY moiety of the present disclosure may be a BODIPY moiety wherein R 1 , R 3 , R 4 and R 6 are each a methyl; R 2 and R 5 are a substituted ester group, wherein the substituted ester group contains an alkyl chain; R 7 and R 8 are each a methyl; and L comprises a linker group.
  • the BODIPY moiety of the present disclosure may be a BODIPY moiety wherein R 1 , R 3 , R 4 and R 6 are each a methyl; R 2 and R 5 are an aryl ester group; R 7 and R 8 are a methyl, group; and L comprises a linker group.
  • the BODIPY moiety of the present disclosure may comprise a BODIPY moiety, wherein R 1 and R 6 may be an alkenyl, R 2 and R 3 link together to form a monocyclic hydrocarbon ring structure, R 4 and R 5 link together to form a monocyclic hydrocarbon ring structure and R 7 and R 8 may be H or a methyl.
  • the BODIPY moiety of the present disclosure may comprise a BODIPY moiety, wherein R 1 and R 6 may be an alkenyl, R 2 and R 3 link together to form a polycyclic hydrocarbon ring structure, R 4 and R 5 link together to form a polycyclic hydrocarbon ring structure and R 7 and R 8 may be H or a methyl.
  • R 2 and R 5 may be a substituted ester wherein the substituted ester is an aryl ester.
  • the aryl ester may be the following structure:
  • R 2 and R 5 may be a substituted ester wherein the substituted ester is an alkyl ester.
  • the alkyl ester may be the following structure: .
  • R 1 and R 6 may be a substituted alkenyl group.
  • the substituted alkenyl group may be the following structure:
  • R 2 and R 3 may link together to form an additional monocyclic hydrocarbon ring structure, or polycyclic hydrocarbon ring structure.
  • the structure may be selected from the following: cyclobutane], cyclopentane], [cyclohexane], [cyclo heptane], cyclooctane], cyclohexene], [cyclohexa-1,4-diene], [c yclopentene], cyclohexa-1,3,diene], or [cyclododecane].
  • R 2 and R 3 are linked together to form a polycyclic hydrocarbon ring structure
  • the structure may be selected from the [hexahydroindene], [1,2,3,4-tetrahydronaphthalene], [2,3-dihydro-1H-indene], [1,1-dimethyl-2,3-dihydro-1H-indene], [2’,3’-dihydrospiro[cyclopentane-1,1’-indene], or [1,2,3,3a-tetrahydropentalene].
  • R 4 and R 5 may link together to form an additional monocyclic hydrocarbon ring structure, or polycyclic hydrocarbon ring structure.
  • the structure may be selected from the following: cyclobutane], cyclopentane], [cyclohexane], [cycloheptane], [cyclooctane], cyclohexene], , , [cyclopentene], cyclohexa-1,3,diene], or [cyclododecane].
  • the structure may be selected from the following: [bicyclo octane], [2,3-dihydro-1H-indene], dimethyl-2,3-dihydro-1H-indene], [2’,3’-dihydrospiro[cyclopentane-1,1’-indene], or [1,2,3,3a-tetrahydropentalene].
  • the photoluminescent complex may comprise a BODIPY moiety having the following chemical formula: wherein R 1 and R 2 may link together to form an additional monocyclic hydrocarbon ring structure or a polycyclic hydrocarbon ring structure; R 3 and R 4 may be H; R 5 and R 6 may link together to form an additional monocyclic hydrocarbon ring structure or a polycyclic hydrocarbon ring structure; R 7 and R 8 are independently selected from H, a methyl, or an ether group; and L represents the linker group comprising a substituted ester linker group.
  • R 1 and R 2 may link together to form polycyclic hydrocarbon ring structure;
  • R 3 and R 4 are methyl;
  • R 5 and R 6 may link together to form a polycyclic hydrocarbon ring structure;
  • R 7 and R 8 may be selected from a H, a methyl, or an ether group; and
  • L is the linker group.
  • R 1 and R 2 may link together to form an additional monocyclic hydrocarbon ring structure, or a polycyclic hydrocarbon ring structure.
  • the structure may be selected from the following: cyclobutane], [cyclopentane], [cyclohexane], [cycloheptane], [cyclooctane], [cyclohexene], [cyclohexa-1,4-diene], [cyclopentene], [cyclohexa-1,3,diene], or [cyclododecane].
  • the structure may be selected from the following: [bicyclooctane], [bicyclopentane],
  • R 5 and R 6 may link together to form an additional monocyclic hydrocarbon ring structure, or polycyclic hydrocarbon ring structure.
  • the structure may be selected from the following: cyclobutane], cyclopentane], [cyclohexane], [cycloheptane], [cyclooctane], cyclohexene], , , [cyclopentene], cyclohexa-1,3-diene], or [cyclododecane].
  • the structure may be selected from the [2,3-dihydro-1H-indene], dimethyl-2,3-dihydro-1H-indene], [2’,3’-dihydrospiro[cyclopentane-1,1’-indene], or [1,2,3,3a-tetrahydropentalene].
  • the distance separating the blue light absorbing azole derivative and the BODIPY moiety may be about 8 ⁇ or greater.
  • the linker group may maintain a distance between the blue light absorbing azole derivative and the BODIPY moiety.
  • the photoluminescent complex comprises a linker group, wherein the linker group covalently links the blue light absorbing azole derivative to the BODIPY moiety.
  • the linker group may comprise a single bond between the azole derivative and the BODIPY moiety.
  • the linker group may comprise an optionally substituted C 2 -C 16 ester group.
  • the linker group may be:
  • the linker group may comprise an unsubstituted ester group.
  • the linker group may be:
  • the photoluminescent complex of the present disclosure may be represented by the following structures which are provided for purpose of illustration and are in no way to be construed as limiting:
  • the photoluminescent complex comprises a blue light absorbing azole derivative.
  • the blue light absorbing azole derivative may comprise an organic lumiphore.
  • the azole derivative may have a maximum absorbance in the light in the range of 400 nm to about 480 nm, about 400 nm to about 410 nm, about 410 nm to about 420 nm, about 420 nm to about 430 nm, about 430 nm to about 440 nm, about 440 nm to about 450 nm, about 450 nm to about 460 nm, about 460 nm to about 470 nm, about 470 nm to about 480 nm, or any wavelength in a range bounded by any of these values.
  • the photoluminescent complex may have an absorbance maximum peak of about 450 nm.
  • the blue light absorbing azole derivative may have a maximum peak absorbance of about 405 nm.
  • the blue light absorbing azole derivative may have a maximum peak absorbance of about 480 nm.
  • Some embodiments include a color conversion film comprising: a color conversion layer comprising a resin matrix and a photoluminescent complex, described above, dispersed within the resin matrix.
  • the color conversion film may be described as comprising a combination of the complexes described herein.
  • Some embodiments include the color conversion film which may be about 1 ⁇ m to about 200 ⁇ m thick.
  • the color conversion film have a thickness of about 1 ⁇ m to about 2 ⁇ m, about 2-3 ⁇ m, about 3-4 ⁇ m, about 4-5 ⁇ m, about 5-6 ⁇ m, about 6-7 ⁇ m, about 7-8 ⁇ m, about 8-9 ⁇ m, about 9-10 ⁇ m, about 1-5 ⁇ m, about 5-10 ⁇ m, about 10-15 ⁇ m, about 15-20 ⁇ m, about 20-40 ⁇ m, about 40-80 ⁇ m, about 80-120 ⁇ m, about 120- 160 ⁇ m about 160-200 ⁇ m, or any thickness in a range bounded by any of these values.
  • the color conversion film may absorb light in the 400 nm to about 480 nm wavelength range and may emit light in the range of about 510 nm to about 560 nm or about 610 nm to about 645 nm. In other embodiments, color conversion film may emit light in the 510 nm to about 560 nm range, the 610 nm to about 645 nm range, or any combination thereof.
  • the color conversion film may further comprise a transparent substrate layer. The transparent substrate layer has two opposing surfaces, wherein the color conversion layer may be disposed on and in physical contact with the surfaces of the transparent layer that will be adjacent to a light emitting source.
  • the transparent substrate is not particularly limited and one skilled in the art would be able to choose a transparent substrate from those used in the art.
  • Some non-limiting examples of transparent substrates include PE (polyethylene), PP (polypropylene), PEN (polyethylene naphthalate), PC (polycarbonate), PMA (polymethylacrylate), PMMA (polymethylmethacrylate), CAB (cellulose acetate butyrate), PVC (polyvinylchloride), PET (polyethyleneterephthalate), PETG (glycol modified polyethylene terephthalate), PDMS (polydimethylsiloxane), COC (cyclo olefin copolymer), PGA (polyglycolide or polyglycolic acid), PLA (polylactic acid), PCL (polycaprolactone), PEA (polyethylene adipate), PHA (polyhydroxy alkanoate), PHBV (poly(3- hydroxybutyrate-co-3hydroxyvalerate)), P
  • the transparent substrate may have two opposing surfaces.
  • the color conversion film may be disposed on and in physical contact with one of the opposing surfaces.
  • the side of the transparent substrates without color conversion film disposed thereon may be adjacent to a light source.
  • the substrate may function as a support during the preparation of the color conversion film.
  • the type of substrates used are not particularly limited, and the material and/or thickness is not limited, as long as it is transparent and capable of functioning as a support. A person skilled in the art could determine which material and thickness to use as a supporting substrate.
  • Some embodiments include a method for preparing the color conversion film, wherein the method comprises: dissolving a photoluminescent compound, described herein, and a binder resin within a solvent; and applying the mixture on to the surface of a transparent substrate.
  • the binder resin which may be used with the photoluminescent complex(s) includes resins such as acrylic resins, polycarbonate resins, ethylene-vinyl alcohol copolymer resins, ethylene-vinyl acetate copolymer resins and saponification products thereof, AS resins, polyester resins, vinyl chloride-vinyl acetate copolymer resins, polyvinyl butyral resins, polyvinylphosphonic acid (PVPA), polystyrene resins, phenolic resins, phenoxy resins, polysulfone, nylon, cellulosic resins, and cellulose acetate resins.
  • resins such as acrylic resins, polycarbonate resins, ethylene-vinyl alcohol copolymer resins
  • the binder resin may be a polyester resin and/or acrylic resin.
  • the solvent which may be used for dissolving or dispersing the complex and the resin may include an alkane, such as butane, pentane, hexane, heptane, and octane; cycloalkanes, such as cyclopentane, cyclohexane, cycloheptane, and cyclooctane; alcohols, such as ethanol, propanol, butanol, amyl alcohol, hexanol, heptanol, octanol, decanol, undecanol, diacetone alcohol, and furfuryl alcohol; CellosolvesTM, such as Methyl CellosolveTM, Ethyl CellosolveTM, Butyl CellosolveTM, Methyl CellosolveTM acetate, and Ethyl CellosolveTM acetate; propyl alcohol
  • Some embodiments include a backlight unit, wherein the backlight unit may include the aforedescribed color conversion film.
  • Other embodiments may describe a display device, wherein the display device may include the backlight unit described hereinto.
  • all numbers expressing quantities of ingredients, properties, such as, molecular weight, reaction conditions, and so forth used in the specification and embodiments are to be understood as being modified in all instances by the term “about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the specification and attached embodiments are approximations that may vary depending upon the desired properties sought to be obtained. At the very least, and not as an attempt to limit the application of the doctrine of equivalents.
  • each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.
  • the functions performed in the processes and methods may be implemented in differing order, as may be indicated by context.
  • the outlined steps and operations are only provided as examples and some of the steps and operations may be optional, combined into fewer steps and operations, or expanded into additional steps and operations.
  • This disclosure may sometimes illustrate different components contained within, or connected with, different other components. Such depicted architectures are merely examples, and many other architectures may be implemented which achieve the same or similar functionality.
  • any disjunctive word and/or phrase presenting two or more alternative terms should be understood to contemplate the possibilities of including one of the terms, either of the terms, or both terms.
  • the phase “A or B” will be understood to include the possibilities of “A” or “B” or “A and B.”
  • the terms “a,” “an,” “the” and similar referents used in the context of describing the present disclosure are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context.
  • a photoluminescent complex comprising: a blue light absorbing azole derivative of general formula: , wherein Z is NR 10 , O or S; R 9 is selected from H, an unsubstituted ester linker group, or a substituted ester linker group; and R 10 is selected from a H, a substituted aryl, an unsubstituted ester linker group, or a substituted ester linker group.
  • linker group wherein the linker group is an unsubstituted ester or substituted ester; and a boron-dipyrromethene (BODIPY) moiety; wherein the linker group covalently links the azole derivative and the BODIPY moiety, wherein the azole derivative absorbs light energy of a first excitation wavelength and transfers an energy to the BODIPY moiety, wherein the BODIPY moiety absorbs the energy from the azole derivative and emits a light energy of a second higher wavelength, and wherein the photoluminescent complex has an emission quantum yield greater than 80%.
  • BODIPY boron-dipyrromethene
  • Embodiment 2 The azole derivative of embodiment 1, wherein Z is NR 10 , R 9 is H, and R 10 is an unsubstituted ester linker group.
  • Embodiment 3 The azole derivative of embodiment 1, wherein Z is NR 10 , R 9 is H, and R 10 is a substituted ester linker group.
  • Embodiment 4 The azole derivative of embodiment 1, wherein Z is NR 10 , R 9 is unsubstituted ester linker, and R 10 is a substituted aryl.
  • Embodiment 5 The azole derivative of embodiment 1, wherein Z is S, R 9 is substituted ester linker, and R 10 is H.
  • Embodiment 6 The azole derivative of embodiment 4, wherein the substituted aryl is: .
  • Embodiment 7 The photoluminescent complex of embodiment 1 wherein the BODIPY moiety is of the general formula: , wherein R 1 and R 6 are independently selected from H, a saturated or unsaturated alkyl group, or an alkenyl group; R 3 and R 4 are independently selected form a H or a C 1 -C 2 alkyl; R 2 and R 5 , are independently selected from H, a saturated alkyl, an unsaturated alkyl, a cyano (-CN), an alkyl ester, or an aryl ester; R 2 and R 3 may link together to form an additional monocyclic hydrocarbon ring structure, or a polycyclic hydrocarbon ring structure; R 4 and R 5 may link together to form an additional monocyclic hydrocarbon ring structure, or a polycyclic hydrocarbon ring structure; R 7 and R 8 may be independently selected from a H, a methyl group;
  • Embodiment 8 The BODIPY moiety of embodiment 7, wherein R 1 , R 3 , R 4 , and R 6 are methyl, R 2 and R 5 are a cyano, R 7 and R 8 are methyl and L is a linker group.
  • Embodiment 9 The BODIPY moiety of embodiment 7, wherein R 1 , R 3 , R 4 , and R 6 are methyl, R 2 and R 5 are selected from a substituted ester, R 7 and R 8 are methyl and L is a linker group.
  • Embodiment 10 The BODIPY moiety of embodiment 7, wherein R 1 , R 3 , R 4 , and R 6 are methyl, R 2 and R 5 are an aryl ester, R 7 and R 8 are a methyl, and L is a linker group.
  • Embodiment 11 The BODIPY moiety of embodiment 7, wherein R 1 and R 6 are each an alkenyl group, R 2 and R 3 link together to form a monocyclic hydrocarbon ring structure, R 4 and R 5 link together to form a monocyclic hydrocarbon ring structure, R 7 and R 8 are each a methyl and L is the linker group
  • Embodiment 12 The BODIPY moiety of embodiment 7, wherein the alkenyl group is the Embodiment 13
  • the photoluminescent complex of embodiment 1 wherein the BODIPY moiety is of the general formula: , R 1 and R 2 link together to form an additional polycyclic hydrocarbon ring structure; R 3 and R 4 are methyl; R 5 and R 6 link together to form an additional polycyclic hydrocarbon ring structure; R 7 and R 8 may be independently selected from a H, a methyl or an ether group; and L represents the linker group comprising a substituted ester linker group.
  • Embodiment 14 The BODIPY moiety of embodiment 13, wherein R 1 and R 2 link together to form a polycyclic hydrocarbon ring structure, R 3 and R 4 , are methyl, R 5 and R 6 may link together to form a polycyclic hydrocarbon ring structure, R 7 and R 8 is selected from a H, or methyl (-CH 3 ), and L is a linker group.
  • Embodiment 15 The photo luminescent complex of embodiments, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, and 14, wherein the unsubstituted ester linker is the following:
  • Embodiment 16 The photoluminescent complex of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 and 11, wherein the substituted ester of the linker group is selected from one if the following structures: ,or .
  • Embodiment 17 The photoluminescent complex of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, and 14, wherein the photoluminescent complex is selected from one of the following structures:
  • Embodiment 18 A color conversion film comprising: a transparent substrate layer; a color conversion layer, wherein the color conversion layer includes a resin matrix, and at least one photoluminescent complex, wherein the at least one photoluminescent compound is comprised the photoluminescent compound of embodiments, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, and 13, dispersed within the resin matrix.
  • Embodiment 19 The color conversion film of embodiment 18, further comprising a singlet oxygen quencher.
  • Embodiment 20 The color conversion film of embodiment 18, further comprising a radical scavenger.
  • Embodiment 21 The color conversion film of embodiment 18, wherein the film has a thickness of between 10 ⁇ m and 200 ⁇ m.
  • Embodiment 22 The color conversion film of embodiment 18, wherein the film absorbs light in about 400 nm to about 480 nm wavelength range and emits light in the 510 nm to about 560 and in the 575 nm to about 645 nm wavelength range.
  • Embodiment 23 A method for preparing the color conversion film of embodiments 18, 19, 20, and 21, the method comprising: dissolving the photoluminescent complex of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16 and 17, and a binder resin within a solvent; and applying the mixture to one of the transparent substrates opposing surfaces.
  • Embodiment 24 A backlight unit including the color conversion film of embodiment 18, 19, 20, and 21.
  • Embodiment 25 A display device including the backlight unit of embodiment 24.
  • Example 1.1 Comparative example 1 CE-1: 0.75 g of 4-hydoxyl-2,6-dimethylbenzaldehyde (5 mmol) and 1.04 g of 2,4- dimethylpyrrole (11 mmol) was dissolved in 100 mL of anhydrous dichloromethane. The solution was degassed for 30 minutes. Then one drop of trifluoroacetic acid was added.
  • Example 2 Synthesis of Photoluminescent Complexes:
  • Example 2.1 PLC-1
  • Compound 1.1 (4-(4-((4-(7-(4-(diphenylamino)phenyl)benzo[c][1,2,5]thiadiazol-4- yl)phenyl)(phenyl)amino)phenyl)-4-oxobutanoic acid):
  • Step 1 Compound 1.1.1 (methyl 4-(4-((4-(7-(4- (diphenylamino)phenyl)benzo[c][1,2,5]thiadiazol-4-yl)phenyl)(phenyl)amino)phenyl)-4- oxobutanoate):
  • a 300 mL 3-neck round bottomed flask was charged with a stir bar and purged with argon.
  • Step 2 Compound 1.1 (4-(4-((4-(7-(4- (diphenylamino)phenyl)benzo[c][1,2,5]thiadiazol-4-yl)phenyl)(phenyl)amino)phenyl)-4- oxobutanoic acid): A 250 mL 3 neck round bottomed flask was charged with a stir bar and flushed with argon. Compound 1.1.1 was added KOH (3.26 mmol, 183 mg), followed by water (5 mL). The flask was fitted with a finned air condenser and heated to 95 °C in an aluminum heating block under argon with vigorous stirring.
  • the dried precipitate was dissolved in anhydrous dichloromethane (500 mL) in an argon-flushed 1 L 2-neck round bottom flask charged with a stir bar.
  • the flask was sealed with a septum and cooled to -10 °C (water-ice/methanol bath) under argon atmosphere.
  • To this flask was added BF 3 ⁇ OEt 2 (571.2 mmol, 70.5 mL) via syringe with vigorous stirring.
  • the flask was fitted with a dropping funnel and anhydrous triethylamine (331.5 mmol, 46.2 mL) was placed in the dropping funnel. The triethylamine was added dropwise over 5 minutes with vigorous stirring.
  • PLC-1 diethyl 3,3'-(14-(4'-((4-(4-((4-(7-(4- (diphenylamino)phenyl)benzo[c][1,2,5]thiadiazol-4-yl)phenyl)(phenyl)amino)phenyl)-4- oxobutanoyl)oxy)-3,5-dimethyl-[1,1'-biphenyl]-4-yl)-7,7-difluoro-1,3,4,7,10,11,12,13- octahydro-2H-6l4,7l4-[1,3,2]diazaborinino[4,3-a:6,1-a']diisoindole-5,9-diyl)(2E,2'E)- diacrylate): A 40 mL screw-cap vial was charged with from Compound 1.2 (0.060 mmol, 42 mg) and Compound 1.1 (0.120 mmol,
  • the vial was sealed with a screw-cap septum and flushed with argon. To this vial was added anhydrous THF (6 mL), followed by DIC (0.182 mmol, 38 mg). After stirring overnight at room temperature under argon, water (35 mL) was added and the resulting precipitate was filtered off, washing with water. The wet precipitate was dissolved in DCM, separated from water, dried over MgSO 4 , filtered, and concentrated in vacuo. The product was purified by flash chromatography using an ethyl acetate/DCM gradient (100% DCM (1 CV) ⁇ 10% ethyl acetate/DCM (10 CV)).
  • Step 2 Methyl 5-(4,7-dibromo-2H-benzo[d][1,2,3]triazol-2-yl)pentanoate: In a small flask, combined 2 g (7.2mmol, 1eq) of the 4,7-dibromo-2H-benzo[d][1,2,3]triazole, 15.5 mL (21 mmol, 15 eq) of methyl 5-bromopentanoate. Added 20 mL N,N’-dimethylformamide. Then added 5 g (36 mmol, 5 eq) of the potassium carbonate. Heated the solution at 75 o C for about 1.5 hours.
  • Step 3 Methyl 5-(4,7-bis(4-(diphenylamino)phenyl)-2H-benzo[d][1,2,3]triazol-2- yl)pentanoate: In a small flask, combined 1.8 g (4.6 mmol, 1 eq) of the methyl 5-(4,7-dibromo- 2H-benzo[d][1,2,3]triazol-2-yl)pentanoate, 10 mL of n-butanol, 3 mL toluene and 3 mL of de- ionized water. Sparged the solution for about 30 minutes with argon.
  • Compound 2.2 Compound 2.2.1 (4,5-dihydro-1H-benzo[g]indole): A mixture of DMSO (50 mL), KOH (3.36 g) and NH 2 OH ⁇ HCl (4.17 g) was stirred at room temperature for 30 min, then 1-tetralone (7.3 g) in DMSO (25 mL) was added. The mixture was stirred at 70 oC for additional 30 min. Then KOH (8.41 g) was added and the resulting mixture was heated to 140 oC, and a solution of 1,2-dichloroethane (9.9 g) in DMSO (25 mL) was added dropwise over 4 hours.
  • PLC-2 ((T-4)-[2-[(4,5-dihydro-2H-benz[g]indol-2-ylidene- ⁇ N)-(3,5-dimethyl-4-(5- (4,7-bis(4-(diphenylamino)phenyl)-2H-benzo[d][1,2,3]triazol-2- yl)pentanoate)phenyl)methyl]-4,5-dihydro-1H-benz[g]indolato- ⁇ N]difluoroboron): A 40 mL screw cap vial was charged with a stir bar, compound 2.1 (0.050 mmol, 32 mg) and compound 2.2 (0.060 mmol, 42 mg), and DMAP:pTsOH 1:1 salt (0.200 mmol, 59 mg).
  • the flask was sealed with a septum and charged with magnesium turnings (145 mmol, 3.525 g) and anhydrous THF (100 mL) via syringe.
  • An oven-dried 100 mL 2 neck round bottom flask was fitted with a gas adapter and flushed with argon. This flask was sealed with a septum and charged with anhydrous THF (60 mL).
  • 1,5- dibromopentane 70.0 mmol, 8.30 mL
  • the 250 mL flask was cooled in an ice-water bath at 0°C°C and the solution of 1,5-dibromopentane was added via syringe with vigorous stirring over 5 minutes.
  • Step 2 (3-(1-(2-bromophenyl)cyclopentyl)-1-tosyl-1H-pyrrole/ 2-(1-(2- bromophenyl)cyclopentyl)-1-tosyl-1H-pyrrole)
  • a 250 mL 2 neck round bottom flask was charged with a stir bar and fitted with a gas adapter. The flask was flushed with argon and 1- (2-bromophenyl)cyclopentan-1-ol (10.0 mmol, 2.412 g) was added to the flask.
  • Step 3 (2-(1-(2-bromophenyl)cyclopentyl)-1-tosyl-1H-pyrrole)
  • a 40 mL screw cap vial was charged with a stir bar.
  • To this vial was added the mixture from Step 2 (estimated 2.37 mmol, 1.05 g).
  • the vial was flushed with argon.
  • To this vial was added potassium carbonate (4.86 mmol, 672 mg), Pd(PPh 3 ) 4 (0.0711 mmol, 82 mg), and anhydrous dimethylformamide (6 mL).
  • the vial was purged of oxygen by vacuum/backfill argon cycles (3 X).
  • the reaction mixture was stirred under argon in a heating block at 110 °C overnight.
  • reaction mixture was cooled to 0 °C with an ice-water bath and p-chloranil (0.655 mmol, 161 mg) was added with stirring.
  • the reaction was stirred at 0 °C for 20 minutes, at which point the oxidation was complete.
  • BF3 ⁇ OEt2 14.67 mmol, 1.8 mL
  • triethylamine 8.78 mmol, 1.2 mL
  • PLC-3 (4-(6',6'-difluoro-6'H-5'l4,6'l4-dispiro[cyclopentane-1,12'- indeno[2',1':4,5]pyrrolo[1,2-c]indeno[2',1':4,5]pyrrolo[2,1-f][1,3,2]diazaborinine-16',1''- cyclopentan]-14'-yl)-3,5-dimethylphenyl 4-(4-((4-(7-(4- (diphenylamino)phenyl)benzo[c][1,2,5]thiadiazol-4-yl)phenyl)(phenyl)amino)phenyl)-4- oxobutanoate): PLC-3 was synthesized from compound 3.1 (0.100 mmol, 60 mg) and compound 1.1 (0.400 mmol, 289 mg) in a manner similar to Compound 2.
  • PLC-4 ((T-4)-[2-[(4,5-dihydro-2H-benz[g]indol-2-ylidene-kN)-(3,5-dimethyl-4-(4-(4- ((4-(7-(4-(diphenylamino)phenyl)benzo[c][1,2,5]thiadiazol-4- yl)phenyl)(phenyl)amino)phenyl)-4-oxobutanoate)phenyl)methyl]-4,5-dihydro-1H- benz[g]indolato-kN]difluoroboron): A 40 mL screw cap vial was charged with a stir bar, Compound 2.2 (0.100 mmol, 60 mg), compound 1.1 (0.150 mmol, 51 mg), and DMAP:pTsOH 1:1 salt (0.200 mmol, 59 mg).
  • Example 2.5 PLC-5 Compound 5.1 [dibenzyl 5,5-difluoro-10-(4-hydroxy-2,6-dimethylphenyl)-1,3,7,9- tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2,8-dicarboxylate]: To a 250 mL round bottom flask 40 mL (241 mmol) of tert-butyl-3-oxobutanoate was dissolved in 80 mL of acetic acid. The mixture was cooled in an ice water bath to about 10 °C.
  • PLC-5 (dibenzyl 10-(4-((5-(4,7-bis(4-(diphenylamino)phenyl)-2H- benzo[d][1,2,3]triazol-2-yl)pentanoyl)oxy)-2,6-dimethylphenyl)-5,5-difluoro-1,3,7,9- tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2,8-dicarboxylate): PLC- 5 was prepared from compound 2.1 (0.050 mmol, 32 mg) and compound 5.1 (0.060 mmol, 42 mg) in a manner similar to compound 2.
  • Step 1 4,7-dibromo-2H-benzo[d][1,2,3]triazole: To 42 mL stirring solution of de-ionized water, added 2.85 g (41.4 mmol, 1.1 eq) of sodium nitrite. This solution was then slowly added to 42 mL of cooled glacial acetic acid. After about 10 mins of mixing, added 10 g (37.6 mmol, 1 eq) of the 3,6-dibromobenzene-1,2-diamine. The cooling bath was removed after completion of the addition. After about 2 hours of stirring at room temperature, the solution was filtered. The collected precipitate was then dried overnight under a room temperature vacuum oven.
  • Step 3 Methyl 4-(4-(4,7-bis(4-(diphenylamino)phenyl)-2H-benzo[d][1,2,3]triazol-2- yl)phenyl)butanoate: To a 2-neck flask equipped with a condenser and under argon, added 150 mg (583 mmol, 1 eq) of the 4,4'-(2H-benzo[d][1,2,3]triazole-4,7-diyl)bis(N,N- diphenylaniline) from previous step.
  • This flask was heated at 120 o C for 3 minutes. The first flask was put to 120 o C heating block. Then the contents of the vial with the ligand and catalyst were transferred to this flask. After about 2 hours of reaction, cooled reaction. Performed column chromatography using a gradient of Hexanes: Ethyl Acetate (9:1). The desired product, compound 6.1.1, was obtained as an orange powder (120 mg, in 26%).
  • PLC-6 dibenzyl 10-(4-((4-(4-(4,7-bis(4-(diphenylamino)phenyl)-2H- benzo[d][1,2,3]triazol-2-yl)phenyl)butanoyl)oxy)-2,6-dimethylphenyl)-5,5-difluoro-1,3,7,9- tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2,8-dicarboxylate): A 40 mL screw cap vial was charged with a stir bar, compound 5.1 (0.055 mmol, 35 mg), compound 6.1 (0.050 mmol, 38 mg), and DMAP:pTsOH 1:1 salt (0.200 mmol, 59 mg).
  • Step 2 A solution comprised of 14.85 g of 3-aminocrotonitrile (180.8 mmol) and 17.95 g of glycine N′-methoxy-N′-methylamide HBr salt (90.4 mmol) dissolved in 1 L of dry ethanol was stirred under argon gas for 16 hr at room temperature. The resulting solution was concentrated in vacuo to the volume of 50 mL. The solid residue was washed with 40 mL of cold EtOH, resulting in 16.71 g of a white solid. The solid was used for step 3 without further purification.
  • Step 3 To a solution comprised of 3.89 g of step 2’s white powder (21.2 mmol) dissolved in 150 mL of dry THF, 7.5 mL of 3.0 M MeMgBr in Et 2 O (1.1 equiv.) was added at - 10 o C while under a nitrogen gas atmosphere. The solution was stirred for 50 min.
  • Step 4 To a slurry comprising 2.67 g of the yellow solid from step 3 (19.3 mmol) in 75 mL of EtOH was added 273 mg of NaOEt (4.01 mmol, 0.2 equiv.).
  • Step 2 8 g of DDQ (35.2 mmol) was added to a solution comprised of step 1’s crude product dissolved in 50 mL of CHCl 3 plus 5 mL of EtOH. The solution was stirred for 1 hr. at room temperature. The solvents were removed under reduced pressure.
  • the solution was stirred for 16 hrs. at room temperature, then heated at 80 °C for 1 hour. Next, the solution was cooled to room temperature and 25 mL of aqueous solution of NaOH (1M) was added, forming an aqueous layer which was separated. The aqueous layer was neutralized with 4 N HCl aqueous solution then extracted with EtOAc. The combined organic layers were dried over MgSO 4 and the solvent was removed. The residue was chromatographed on column of silica gel using Hexanes/Et0Ac (1:1) as the eluent, resulting in 1.05 g of product (39 % yield).
  • PLC-7 (4-(2,8-dicyano-5,5-difluoro-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2- c:2',1'-f][1,3,2]diazaborinin-10-yl)-3,5-dimethylphenyl 4-(4-(4,7-bis(4- (diphenylamino)phenyl)-2H-benzo[d][1,2,3]triazol-2-yl)phenyl)butanoate): A 40 mL screw cap vial was charged with a stir bar, compound 7.1 (0.055 mmol, 35 mg) and compound 6.1 (0.050 mmol, 38 mg), and DMAP:pTsOH 1:1 salt (0.200 mmol, 59 mg).
  • Step 1 Oxone monopersulfate (78.88 g, 127.96 mmol) was added to a mixture 2- nitroaniline (10.58 g, 76 mmol) in H 2 O (210 mL), DCM (590 mL), and the resulting mixture was stirred at 40 o C for 48 hours. After cooling to RT, the reaction was separated. The aqueous layer was re-extracted with DCM (150 mL x 2), The DCM layers were combined washed with 1N HCl aqueous solution, water, and brine, then dried over MgSO 4 , and concentrated to dryness. The brownish color solid was triturated with EtOH, filtered, then air dried, affording 6.61 g light brown solid product.
  • Step 2 A mixture of 1-nitro-2-nitrosobenzene (1.4 g, 9.2 mmol), 4-fluoroaniline (1.02 g, 9.2 mmol) in AcOH (50 mL) was stirred at RT for 16 hours. The mixture was poured into ice water, the brown color solid was collected by filtering, the product was washed with water several times then dried in vacuo- oven to dryness, affording 2.0 g light brown solid product. Yield 89%. The product was used next step without further purification.
  • Step 3 Formamidine sulfinic acid (2.9 g, 26.89 mmol) was added to a mixture of (E/Z)- 1-(4-fluorophenyl)-2-(2-nitrophenyl) diazene (2.0 g, 8.15 mmol) in EtOH (50 mL) following by 4 N NaOH aqueous solution (42 mL), the resulting mixture was stirred at 85 o C for 16 hours.
  • PLC-8 (dibenzyl 10-(4-((4-(4-((4-(7-(4-(diphenylamino)phenyl)-2-(4-fluorophenyl)- 2H-benzo[d][1,2,3]triazol-4-yl)phenyl)(phenyl)amino)phenyl)butanoyl)oxy)-2,6- dimethylphenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'- f][1,3,2]diazaborinine-2,8-dicarboxylate): A 250 mL 2 neck round bottom flask was fitted with a finned condenser, stir bar, and a gas adapter.
  • PLC-9 (4-(2,8-dicyano-5,5-difluoro-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2- c:2',1'-f][1,3,2]diazaborinin-10-yl)-3,5-dimethylphenyl 4-(4-((4-(7-(4- (diphenylamino)phenyl)-2-(4-fluorophenyl)-2H-benzo[d][1,2,3]triazol-4- yl)phenyl)(phenyl)amino)phenyl)butanoate): A 250 mL 2-neck round bottom flask was fitted with a finned condenser, stir bar, and a gas adapter.
  • a 1.1 mm thick glass substrate measuring 1-inch X 1-inch was cut to size.
  • the glass substrate was then washed with detergent and deionized (DI) water, rinsed with fresh DI water, and sonicated for about 1 hour.
  • the glass was then soaked in isopropanol (IPA) and sonicated for about 1 hour.
  • the glass substrate was then soaked in acetone and sonicated for about 1 hour.
  • the glass was then removed from the acetone bath and dried with nitrogen gas at room temperature.
  • a 20 wt% solution of poly(methylmethacrylate) (PMMA) (average M.W. 120,000 by GPC from MilliporeSigma, Burlington, MA, USA) copolymer in cyclopentanone (99.9% pure) was prepared.
  • the prepared copolymer was stirred overnight at 40 °C.
  • the 20% PMMA solution prepared above (4 g) was added to 3 mg of the photoluminescent complex made as described above in a sealed container and mixed for about 30 minutes.
  • the PMMA/lumiphore solution was then spin coated onto a prepared glass substrate at 1000 RPM for 20 s and then 500 RPM for 5 s.
  • the resulting wet coating had a thickness of about 10 ⁇ m.
  • the samples were covered with aluminum foil before spin coating to protect them from exposure to light. Three samples each were prepared in this manner for each for Emission/FWHM and quantum yield.
  • the spin coated samples were baked in a vacuum oven at 80 °C for 3 hours to evaporate the remaining solvent.
  • the dried coating had a thickness of about 2 ⁇ m.
  • the 1-inch X 1-inch sample was inserted into a Shimadzu, UV-3600 UV-VIS- NIR spectrophotometer (Shimadzu Instruments, Inc., Columbia, MD, USA). All device operations were performed inside a nitrogen-filled glove-box.
  • the resulting absorption/emission spectrum for PLC-1 is shown in FIG.1, while the resulting absorption/emission spectrum for PLC-5 is shown in FIG.2.
  • the fluorescence spectrum of a 1-inch X 1-inch film sample prepared as described above was determined using a Fluorolog spectrofluorometer (Horiba Scientific, Edison, NJ, USA) with the excitation wavelength set at the respective maximum absorbance wavelength. The maximum emission and FWHM are shown in Table 1.
  • the quantum yield of a 1-inch X 1-inch sample prepared as described above were determined using a Quantarus-QY spectrophotometer (Hamamatsu Inc., Campbell CA, USA) was excited at the respective maximum absorbance wavelength. The results are reported in Table 1.
  • the results of the film characterization (absorbance peak wavelength, FWHM, and quantum yield) are shown in Table 1. Below. Table 1.

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Abstract

La présente invention concerne un nouveau complexe photoluminescent comprenant une fraction BODIPY liée de manière covalente à un dérivé azole absorbant la lumière bleue, un film de conversion de couleur et une unité de rétroéclairage l'utilisant.
PCT/US2021/022900 2020-03-20 2021-03-18 Composés émissifs cycliques contenant du bore et film de conversion de couleur les contenant Ceased WO2021188762A1 (fr)

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KR1020227032539A KR102818945B1 (ko) 2020-03-20 2021-03-18 보론 함유 환형 발광 화합물 및 이를 함유하는 색 변환 필름
JP2022555947A JP7458498B2 (ja) 2020-03-20 2021-03-18 含ホウ素環式放出化合物及びそれを含む色変換フィルム

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150171328A1 (en) * 2012-07-19 2015-06-18 Centre National De La Recherche Scientifique Fluorescent compounds of the boron thienyldipyrromethene type, and their use
US9399730B2 (en) 2011-12-06 2016-07-26 Nitto Denko Corporation Wavelength conversion material as encapsulate for solar module systems to enhance solar harvesting efficiency
WO2019031456A1 (fr) * 2017-08-10 2019-02-14 日本化薬株式会社 Composé chélate de bore de dibenzopyrrométhène, matériau absorbant la lumière proche infrarouge, couche mince et dispositif électronique organique
US20190270758A1 (en) * 2016-10-28 2019-09-05 Nippon Kayaku Kabushiki Kaisha Dibenzopyrromethene Boron Chelate Compound, Near-Infrared Light Absorbing Material, Thin Film and Organic Electronics Device

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105419379B (zh) * 2011-09-26 2018-11-20 日东电工株式会社 用于提高的日光采集效率的高荧光且光稳定性生色团
JP2016509621A (ja) * 2013-01-04 2016-03-31 日東電工株式会社 波長変換のための高蛍光性光安定性発色団
JP6367834B2 (ja) * 2013-01-31 2018-08-01 日東電工株式会社 色覚異常を矯正するための光学素子
WO2014160707A1 (fr) * 2013-03-26 2014-10-02 Nitto Denko Corporation Films à conversion de longueur d'onde comportant de multiples chromophores organiques photostables
WO2015023574A1 (fr) * 2013-08-13 2015-02-19 Nitto Denko Corporation Concentrateur solaire luminescent utilisant des composés organiques photostables chromophores
TWI708776B (zh) * 2016-03-08 2020-11-01 南韓商Ｌｇ化學股份有限公司 化合物與包含其之色轉換膜、背光單元及顯示裝置
CN110229659B (zh) 2019-05-24 2022-10-25 中山大学 一种过氧草酸酯/水凝胶发光相体系及其制备方法和应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9399730B2 (en) 2011-12-06 2016-07-26 Nitto Denko Corporation Wavelength conversion material as encapsulate for solar module systems to enhance solar harvesting efficiency
US20150171328A1 (en) * 2012-07-19 2015-06-18 Centre National De La Recherche Scientifique Fluorescent compounds of the boron thienyldipyrromethene type, and their use
US20190270758A1 (en) * 2016-10-28 2019-09-05 Nippon Kayaku Kabushiki Kaisha Dibenzopyrromethene Boron Chelate Compound, Near-Infrared Light Absorbing Material, Thin Film and Organic Electronics Device
WO2019031456A1 (fr) * 2017-08-10 2019-02-14 日本化薬株式会社 Composé chélate de bore de dibenzopyrrométhène, matériau absorbant la lumière proche infrarouge, couche mince et dispositif électronique organique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CAS, no. 9011-14-7

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