WO2023158977A1 - 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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WO2023158977A1
WO2023158977A1 PCT/US2023/062465 US2023062465W WO2023158977A1 WO 2023158977 A1 WO2023158977 A1 WO 2023158977A1 US 2023062465 W US2023062465 W US 2023062465W WO 2023158977 A1 WO2023158977 A1 WO 2023158977A1
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mmol
compound
complex
color conversion
photoluminescent
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PCT/US2023/062465
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English (en)
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Shijun Zheng
Jeffrey R. Hammaker
Xinliang DING
Peng Wang
Tissa Sajoto
Jie Cai
Isamu KITAHARA
Hiep Luu
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Nitto Denko Corporation
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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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
    • H01L33/50—Wavelength conversion elements
    • H01L33/501—Wavelength conversion elements characterised by the materials, e.g. binder
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
    • H01L33/50—Wavelength conversion elements
    • H01L33/501—Wavelength conversion elements characterised by the materials, e.g. binder
    • H01L33/502—Wavelength conversion materials

Definitions

  • the present disclosure is related to compounds for use in a color conversion film, and backlight unit and a display apparatus including the same.
  • BACKGROUND Unless otherwise indicated in the present disclosure, the materials described in the present disclosure are not prior art to the claims in the present application and are not admitted to be prior art by inclusion in this section.
  • color reproduction the gamut, or color gamut, is a certain complete subset of colors available on a device such as a television or monitor.
  • RGB Red Green Blue
  • a wide-gamut color space achieved by using pure spectral primary colors was developed to provide a broader color gamut and offer a more realistic representation of visible colors viewed through a display.
  • Quantum dots suffer from a variety of shortcomings including toxicity, low efficiency, expensive encapsulating processes and size uniformity. Therefore, there exists a need for improving performance in color conversion films, backlight units, and display devices.
  • 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 provides 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 about 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 a light emitting apparatus.
  • the color conversion film of the present disclosure reduced color deterioration by reducing overlap within the color spectrum resulting in high quality color rendition.
  • the photoluminescent complex described herein may include a blue light absorbing xanthenoisoquinoline derivative; a linker complex, wherein the linker complex is an unsubstituted ester or substituted ester; and a boron-dipyrromethene (BODIPY) moiety, wherein the linker complex covalently links the xanthenoisoquinoline derivative and the BODIPY moiety, wherein the xanthenoisoquinoline 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 xanthenoisoquinoline 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
  • the xanthenoisoquinoline derivative may be of the general formula: , wherein R 10 is a bond, an H, a C1-C4 alkyl group, or an optionally substituted aryl group.
  • the optionally substituted aryl group may comprise , some embodiments, the BODIPY moiety may be of the general Formula 1 or Formula 2, as shown below: ; wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are independently H, a C1-C3 alkyl, an optionally substituted aryl group, or an optionally substituted ether group; R 7 , R 8 , and R 9 are independently H or a methyl group (-CH 3 ); and L1, L2, and L3 are linker complexes, independently comprising an optionally substituted ester moiety.
  • R 3 and R 4 may each be an aryl group, e.g., a phenyl group.
  • the aryl group may be an optionally substituted aryl group.
  • the optionally substituted aryl group can be a phenyl group ( ), or a diphenyl group .
  • the optionally substituted aryl group may comprise a 4-trifluoromethylphenyl group ( ), or a 3,5-bis(trifluoromethyl)phenyl group ( .
  • the linker complexes L1, L2, and L3, may be independently .
  • the linker complexes L1, L2, and L3, may be independently .
  • the color conversion film may comprise a transparent substrate layer, and a color conversion layer.
  • the color conversion layer includes a resin matrix, wherein the resin matrix comprises poly(butyl acrylate) or poly(methyl methacrylate), and a photoluminescent complex comprising the compounds described herein dispersed within the resin matrix.
  • the color conversion film may further comprise a singlet oxygen quencher.
  • the color conversion film may further comprise a radical scavenger.
  • the color conversion film may have a thickness of between 10 ⁇ m and 200 ⁇ m.
  • the film may absorb light in a wavelength range of about 400 nm to about 590 nm and emit light in a wavelength range of about the 600 nm to about 620 nm.
  • a method for preparing the color conversion film is described, the method may comprise dissolving the photoluminescent complex of the embodiments described above, and a binder resin within a solvent; and applying the mixture to one of the transparent substrates opposing surfaces.
  • a backlight unit is described, the backlit unit may include the color conversion film described above.
  • a display device is described, the display device may include the back-light unit described above.
  • FIG.1 is a graph depicting the absorption and emission spectra of one embodiment of a photoluminescent complex (Compound 5).
  • FIG.2 is a graph depicting the absorption and emission spectra of one embodiment of a photoluminescent complex (Compound 6).
  • FIG.3 is a graph depicting the absorption and emission spectra of one embodiment of a photoluminescent complex (Compound 7).
  • the current disclosure includes photoluminescent complexes and their uses in color conversion films, backlight units, and/or display devices.
  • a photoluminescent complex 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 a photoluminescent complex that may enhance the contrast or intensity between two colors, increasing their distinction from one another.
  • the present disclosure also includes methods for preparing the color conversion films described herein.
  • a 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.
  • a substituent group may have one or more substituent groups on the parent group structure. In one or more forms, the substituent groups may be independently selected from an optionally substituted alkyl, alkenyl, or a C 3 -C 7 heteroalkyl.
  • the term “optionally substituted” includes parent structures that may or may not be substituted as defined above.
  • alkyl as used herein refers to an aliphatic hydrocarbon group.
  • the alkyl group may be a “saturated alkyl” group, which means that it does not contain any alkene or alkyne moieties.
  • the alkyl moiety may also be an “unsaturated alkyl” moiety, which means that it contains at least one alkene or alkyne moiety.
  • the alkyl 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.
  • C1-C6 alkyl indicates that there are one to six carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, or t-butyl.
  • C 1 -C 6 alkyl includes C 1 -C 2 alkyl, C 1 -C 3 alkyl, C 1 -C 4 alkyl, C 1 -C 5 alkyl.
  • Alkyl groups may be substituted or unsubstituted.
  • Typical alkyl groups include, but are in no way limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
  • 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, -CH2-O-CH3, -CH2-CH2-O-CH3, -CH2-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, -CH2-NH-O-CH3, 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.
  • 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.
  • 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.
  • esters refers to a chemical moiety with the formula -COOR, where R is alkyl, cycloalkyl, aryl, heteroaryl (bonded through a ring carbon) or heterocyclic (bonded through a ring carbon). Any hydroxyl, or carboxyl side chain on the compounds described herein may be esterified. Any suitable procedure to prepare an ester may be used. 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 binder resin may comprise poly(methyl methacrylate)” should be interpreted as, for example, “In some embodiments, the binder resin comprises poly(methyl methacrylate),” or “In some embodiments, the binder resin does not comprise poly(methyl methacrylate).”
  • BODIPY refers to a chemical moiety with the general formula: , wherein the BODIPY compound is composed of a dipyrromethene moiety complexed with a di-substituted boron atom, typically a BF 2 unit.
  • the IUPAC name for the BODIPY core is 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene.
  • xanthenoisoquinoline or “xanthenoisoquinoline derivative” as used herein, refers to a chemical moiety with the general formula: .
  • the IUPAC name for the xanthenoisoquinoline core is 1H- xantheno[2,1,9-def]isoquinoline-1,3(2H)-dione.
  • the present disclosure is related to photoluminescent complexes that absorb light energy of a 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 optimized for the absorbing luminescent moiety to transfer its energy to the acceptor luminescent moiety, wherein the acceptor luminescent moiety then emits energy at a second wavelength that is larger than the absorbed first wavelength.
  • the photoluminescent complexes described herein comprise: a blue light absorbing xanthenoisoquinoline derivative (XI derivative); a linker complex; and a boron-dipyrromethene (BODIPY) moiety.
  • the linker complex may covalently link the xanthenoisoquinoline derivative to the BODIPY moiety.
  • the xanthenoisoquinoline 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. It is believed that energy transfer from the excited xanthenoisoquinoline derivative to the BODIPY moiety occurs through a Förster resonance energy transfer (FRET).
  • FRET Förster resonance energy transfer
  • the photoluminescent complex may have a high emission quantum yield.
  • the emission quantum yield may be greater than 50%, 60%, 70%, 80%, or 90%.
  • the emission quantum yield may be greater than 50%, or 55%, or 60%, or 65%, or 70%, or 75%, or 80%, or 85%, or 90%, or 95%.
  • 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%), 0.95 (95%), or up to 100%.
  • Quantum yield measurements of photoluminescent complex films may be made by spectrophotometer, e.g., Quantaurus-QY spectrophotometer (Hamamatsu, Inc., Campbell, CA, USA).
  • the photoluminescent complex has an emission band, wherein the emission band 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 55 nm, less than or equal to about 50 nm, less than or equal to about 45 nm, less than or equal to about 40 nm, less than or equal to about 35 nm, less than or equal to about 30 nm, less than or equal about 25 nm, less than or equal to about 20 nm, or about 39 nm, about 40 nm, or about 41 nm.
  • the photoluminescent complex may have a Stokes shift that is equal to or greater than 45 nm.
  • the term “Stokes shift” means the distance between the excitation peak of the photoluminescent complex (or a moiety thereof) and the emission peak of the photoluminescent complex (or a moiety thereof).
  • the Stokes shift of the photoluminescent complex may be about 45-50 nm, about 50-55 nm, about 55-60 nm, about 60-65 nm, about 65-70 nm, about 70-75 nm, about 75-80 nm, about 80-85 nm, about 85-90 nm, about 90-95 nm, about 95-100 nm, or greater than about 100 nm, or any number in a range bounded by any of these values.
  • the Stokes shift of the photoluminescent complex may be greater than 100 nm, greater than 120 nm, greater than 130, greater than 140 nm, greater than 150 nm, or greater than 170 nm.
  • the Stokes shift between the blue-light absorbing moiety and the emission peak of the BODIPY moiety may be any number or range disclosed herein.
  • the photoluminescent complex of the current disclosure may have a tunable (or adjustable) emission wavelength. By incorporating different substituents to the BODIPY moiety, the emission wavelength may be adjusted to between about 600 nm to about 645 nm.
  • the photoluminescent complex may absorb light energy at one or more wavelengths.
  • the xanthenoisoquinoline moiety of the photoluminescent complex may absorb light.
  • the BODIPY moiety of the photoluminescent complex may absorb light.
  • both the BODIPY moiety of the photoluminescent complex and the xanthenoisoquinoline moiety of the photoluminescent complex may absorb light.
  • the xanthenoisoquinoline moiety of the photoluminescent complex may have a peak absorption maximum wavelength between about 400 nm to about 470 nm, about 400-405 nm, about 405-410 nm, about 410-415 nm, about 415-420 nm, about 420-425 nm, about 425-430 nm, about 430-435 nm, about 435-440 nm, about 440-445 nm, about 445-450 nm, about 450-455 nm, about 455-460 nm, about 460-465 nm, about 465-470 nm.
  • the BODIPY moiety of the photoluminescent complex may have a peak absorption maximum wavelength between about 500 nm to about 600 nm, about 500-510 nm, about 510-520 nm, about 520-530 nm, about 530-540 nm, about 540-550 nm, about 550-555 nm, about 555-560 nm, about 560-565 nm, about 565-570 nm, about 570-575 nm, about 575-585 nm, about 585- 590 nm, about 590-600 nm, about 570-585 nm, or any wavelength in a range bounded by any of these values.
  • the photoluminescent complex may have an absorption wavelength between about 400 nm to about 405 nm, about 405-410 nm, about 410-415 nm, about 415-420 nm, about 420-425 nm, about 425-430 nm, about 430-435 nm, about 435-440 nm, about 440-445 nm, about 445-450 nm, about 450-455 nm, about 455-460 nm, about 460-465 nm, about 465-470 nm, about 500-600 nm, about 500-510 nm, about 510- 520 nm, about 520-530 nm, about 530-540 nm, about 540-550 nm, about 550-555 nm, about 555-560 nm, about 560-565 nm, about 565-570 nm, about 570-575 nm, about 575-585 nm,
  • the photoluminescent complex may have an emission peak wavelength between about 595 nm to about 645 nm, about 595-600 nm, about 600-605 nm, about 605-610 nm, about 610-615 nm, about 615-620 nm, about 620-625 nm, about 625-630 nm, about 630-635 nm, about 635-640 nm, about 640-645 nm, about 605-620 nm, or any wavelength in a range bounded by any these values.
  • inventions include photoluminescent complexes wherein the blue light absorbing xanthenoisoquinoline derivative and the BODIPY moiety’s spatial distance is adjusted through the linker complex, for improving the transfer of the blue light absorbing xanthenoisoquinoline derivative’s energy to the BODIPY moiety.
  • the linker complex covalently links the blue light absorbing xanthenoisoquinoline derivative and the BODIPY moiety.
  • the xanthenoisoquinoline 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 xanthenoisoquinoline derivative and emits a light energy of a second higher wavelength, and wherein the photoluminescent complex has an emission quantum yield greater than 80%.
  • Some embodiments include a blue light absorbing xanthenoisoquinoline derivative of the following general formula: wherein R 10 may be independently H, methyl (-CH3), a, optionally substituted alkyl group, or an optionally substituted aryl group.
  • the optionally substituted alkyl group may be a trifluoromethyl group (-CF 3 ) or a trichloromethyl group (-CCl 3 ).
  • the optionally substituted aryl group may be phenyl.
  • the optionally substituted aryl group may be a substituted phenyl or benzyl group.
  • the optionally substituted aryl group may comprise trifluoromethyl group.
  • the optionally substituted aryl group may be o .
  • the linker complex covalently links the blue absorbing xanthenoisoquinoline derivative with the BODIPY moiety.
  • the linker complex may be tuned (or adjusted) to optimize the spatial distance between the blue light absorbing xanthenoisoquinoline derivative and the BODIPY moiety. By optimizing the spatial distance between the xanthenoisoquinoline derivative and the BODIPY moiety, the quantum yield may be improved. In some embodiments, the distance separating the blue light absorbing xanthenoisoquinoline derivative and the BODIPY moiety may be about 8 ⁇ or greater. In some embodiments, the linker complex maintains a distance between the blue light absorbing xanthenoisoquinoline derivative and the BODIPY moiety.
  • the photoluminescent complex comprises a linker complex, wherein the linker complex covalently links the blue light absorbing xanthenoisoquinoline derivative to the BODIPY moiety.
  • the linker complex may comprise a single bond between the xanthenoisoquinoline derivative and the BODIPY moiety.
  • the linker complex (e.g., L1, L2 and/or L3) may comprise an optionally substituted C 2 -C 7 ester group.
  • the linker complex may be one of the following structures: , In some, embodiments, the linker complex may comprise an unsubstituted ester group, wherein the linker complex may be one of the following structures: .
  • the linker complexes L1, L2, and L3 may be the same or different. In some embodiments, L 1 , L 2 , and L 3 may all be identical. In some embodiments, L 1 , L2, and L3 may all be different. In some embodiments, L1, and L2 may be identical and L3 is different. All possible permutations for the linker complexes are contemplated.
  • the photoluminescent complex of the current disclosure may comprise a BODIPY moiety.
  • the BODIPY moiety may have the following general formulae; .
  • R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from a bond, H, a C 1 -C 3 alkyl, an aryl, or an ether.
  • the aryl group may be substituted.
  • the substituted aryl group may some embodiments, the substituted aryl group may be In some embodiments, R 7 , R 8 , and R 9 may be independently selected from a bond, H, or a methyl group (-CH3).
  • the BODIPY moiety of the present disclosure may be a BODIPY moiety wherein R 3 and R 4 may each be an aryl group, e.g., a phenyl group; R 1 , R 2 , R 5 and /or R 6 may be a bond or an
  • the photoluminescent complexes of the present disclosure may be represented by the following structure which are provided for purpose of illustration and are in no way to be construed as limiting: ,
  • Some embodiments include a color conversion film, comprising: a color conversion layer wherein the color conversion layer includes a resin matrix and photoluminescent complexes, described above, dispersed within the resin matrix.
  • the color conversion film may be described as comprising one or more of the complexes described herein.
  • Some embodiments include a color conversion film which may have a thickness of about 1 ⁇ m to about 200 ⁇ 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 about 10 ⁇ m, or any thickness in a range bounded by any of these values.
  • 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 (polymethyl acrylate), PMMA (polymethyl methacrylate), 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-3-hydroxyvalerate)
  • the binder resin may comprise poly(methyl methacrylate), also termed PMMA.
  • the binder resin may comprise poly(butyl acrylate), also termed PBA.
  • the binder resin may be a copolymer mixture comprising 50%, 75%, 95% butyl acrylate co-polymers/monomer. It is believed that, compared to PMMA, the poly(butyl acrylate) matrix may provide a more non-polar environment (having n-butyl alkyl chains in the structure).
  • 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.
  • 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 the 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.
  • the binder resin may be a polyester resin and/or acrylic resin.
  • the binder resin may comprise polymethacrylate (PMMA). In some embodiments, the binder resin may comprise poly (butyl acrylate) (PBA). Any suitable solvent or combination of solvents may be used for dissolving or dispersing the complex and the resin.
  • the solvent may be an alkane, such as butane, pentane, hexane, heptane, and octane; cycloalkanes, such as cyclopentane, cyclohexane, cycloheptane, and cyclooctane; an alcohol, 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; propylene glycol and its derivatives, such as propylene glycol monomethyl ether, propylene glycol monoethyl ether,
  • Some embodiments include a backlight unit, wherein the backlight unit may include the aforedescribed color conversion film.
  • Other embodiments may include a display device, wherein the device may include the backlight unit described herein.
  • 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 xanthenoisoquinoline derivative; a linker complex, wherein the linker complex is an unsubstituted ester or substituted ester; and a boron-dipyrromethene (BODIPY) moiety; wherein the linker complex covalently links the xanthenoisoquinoline derivative and the BODIPY moiety, wherein the xanthenoisoquinoline 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 xanthenoisoquinoline derivative and emits a light energy of a second higher wavelength, and wherein the photoluminescent complex has an emission quantum yield greater than 80%.
  • Embodiment 2 The photoluminescent complex of embodiment 1, wherein the xanthenoisoquinoline derivative is of the general formula: , wherein R 0 is a bond, an H, a C1-C4 alkyl group, or an optionally substituted aryl group.
  • Embodiment 3 The photoluminescent complex of embodiment 1 wherein the BODIPY moiety is of the general formula: ; wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are independently selected from a bond, an H, C1-C3 alkyl, aryl and/ or an ether; wherein R 7 , R 8 , and R 9 can be independently selected from a bond, H, or a methyl group (- CH3); and wherein L1, L2, and L3 are an independent linker complex, wherein the linker complex is an unsubstituted ester or substituted ester.
  • Embodiment 4 The photoluminescent complex of embodiment 3, wherein R3 and R4 can comprise an aryl group.
  • Embodiment 5 The photoluminescent complex of embodiment 4, wherein the aryl group comprises a phenyl group
  • Embodiment 6 The photoluminescent complex of embodiment 4, wherein the phenyl group comprises a 4-trifluromethylphenyl group, or a 3,5-bis(trifluoromethyl)phenyl group.
  • Embodiment 7 The photoluminescent complex of embodiment 3, wherein the substituted aryl group can be a phenyl group or a diphenyl group ( Embodiment 8 The photoluminescent complex of embodiment 3, wherein the ether group can be a C2-C10 alkyl ether group ( Embodiment 9 The photoluminescent complex of embodiment 1, wherein the linker , Embodiment 10 The photoluminescent complex of embodiment 1, 2, 3, 4, 5, 6, 7, 8, or 9, wherein the unsubstituted ester linker is , Embodiment 11 The photoluminescent complex of embodiment 1, 2, 3, 4, 5, 6, 7, 8, or 9, wherein the substituted ester of the linker complex is one of the following structures: .
  • Embodiment 12 The photoluminescent complex of embodiment 1, wherein the photoluminescent complex is one of the following structures: , ,
  • Embodiment 13 A color conversion film, comprising: a transparent substrate layer; a color conversion layer, wherein the color conversion layer includes a resin matrix, wherein the resin matrix comprises butyl acrylate; and at least one photoluminescent complex, wherein the at least one photoluminescent compound comprises the photoluminescent compound of embodiment, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12, dispersed within the resin matrix.
  • Embodiment 14 The color conversion film of embodiment 13, further comprising a singlet oxygen quencher.
  • Embodiment 15 The color conversion film of embodiment 13, further comprising a radical scavenger.
  • Embodiment 16 The color conversion film of embodiment 13, wherein the film has a thickness of between about 10 ⁇ m and about 200 ⁇ m.
  • Embodiment 17 The color conversion film of embodiment 13, wherein the film absorbs light in about 400 nm to about 600 nm wavelength range and emits light in the about 575 nm to about 645 nm wavelength range.
  • Embodiment 18 A method for preparing the color conversion film, the method comprising: dissolving the photoluminescent complex of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, and a binder resin within a solvent; and applying the mixture to one of the transparent substrates opposing surfaces.
  • Embodiment 19 A backlight unit including the color conversion film of embodiment 13.
  • Embodiment 20 A display device including the back-light unit of embodiment 19.
  • 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. The solution was stirred overnight under argon gas atmosphere at room temperature. To the resulting solution, DDQ (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone ) (2.0g) was added and the mixture was stirred overnight.
  • DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
  • CE-2 has the following structure:
  • Example 2 Synthesis of Photoluminescent Complexes:
  • Compound 1.1 To a solution of benzaldehyde (5 mmol), 4-methoxyacetophenone (995 mg, 5 mmol) in 10 mL ethanol, will be added a 10% sodium hydroxide aqueous solution (5 mL) dropwise. The mixture will be stirred for 15 min, filtration and washing with 20 mL ethanol/water (1:1) will give a white solid.
  • the resulted mixture will be stirred at 0 oC for additional one hour, then poured into 300 g ice slowly.
  • the ice-organic mixture will be extracted with ethyl acetate (200 mL x2), washed with 10% Potassium carbonate (K2CO3) aqueous solution (100 mL), brine (100 mL), dried over magnesium sulfate (MgSO4). After filtered off the solid, the solvents will be removed under reduced pressure to give a liquid which will be submitted for next step reaction without further purification.
  • Step-2 A mixture of liquid from reaction above (9 mmol) and ammonium acetate (3.54 g, 46 mmol) in 20 mL acetic acid will be heated at 100 °C for 5 hours. After cooled to room temperature, the mixture will be worked up with water (200 mL), extracted with ethyl acetate (250 mL). The organic phase will be washed with brine, loaded on silica gel, and purified by flash chromatography using eluents of hexanes/dichloromethane (DCM) (0% to 50% DCM). The main peak will be collected, and removal of solvents will give a solid.
  • DCM hexanes/dichloromethane
  • Compound 1 A mixture of Compound 1.5 (0.1 mmol), 2-(4-(1,3-dioxo-9-(4-(trifluoromethyl)phenyl)-1H- xantheno[2,1,9-def]isoquinolin-2(3H)-yl)phenyl)acetic acid (Compound 5.5, vide infra, 0.3 mmol), diisopropylcarbodiimide (DIC) (0.63 mmol), dimethylaminopyridine (DMAP)/TsOH salt (58 mg, 0.2 mmol) in DCM (10 mL) will be stirred at room temperature overnight.
  • DIC diisopropylcarbodiimide
  • DMAP dimethylaminopyridine
  • TsOH salt 58 mg, 0.2 mmol
  • TEA 0.75 mL, 5.25 mmol
  • BF3-Et2O 2.0 mL, 16.5 mmol
  • the resulted mixture will be diluted with 100 mL DCM, washed with water, dried over MgSO4, loaded on silica gel, and purified by flash chromatography using eluents of DCM/EA (0% to 10% EA). The desired peak will be collected, removal of solvents will give a dark purple solid.
  • Compound 2 A mixture of Compound 2.3 (0.1 mmol), 2-(4-(1,3-dioxo-9-(4-(trifluoromethyl)phenyl)-1H- xantheno[2,1,9-def]isoquinolin-2(3H)-yl)phenyl)acetic acid (Compound 5.5, 0.3 mmol), DIC (0.63 mmol), DMAP/TsOH salt (58 mg, 0.2 mmol) in DCM (10 mL) will be stirred at room temperature overnight. The resulted solution will be loaded on silica gel and purified by flash chromatography using eluents of DCM/EA (0% to 10% EA). The desired peak will be collected, and removal of solvent will give the product as solid. Synthesis of Compound 3
  • Compound 3 A mixture of Compound 7.7 (vide infra, 0.1 mmol), 2-(4-(1,3-dioxo-9-(4- (trifluoromethyl)phenyl)-1H-xantheno[2,1,9-def]isoquinolin-2(3H)-yl)phenyl)acetic acid (Compound 5.5, vide infra, 0.3 mmol), DIC (0.63 mmol), DMAP/TsOH salt (58 mg, 0.2 mmol) in DCM (10 mL) will be stirred at room temperature overnight. The resulted solution will be loaded on silica gel and purified by flash chromatography using eluents of DCM/EA (0% to 10% EA). The desired peak will be collected, and removal of solvent will give the product as solid. Synthesis of Compound 4
  • Compound 4 A mixture of Compound 4.5 (0.1 mmol), 2-(4-(1,3-dioxo-9-(4-(trifluoromethyl)phenyl)-1H- xantheno[2,1,9-def]isoquinolin-2(3H)-yl)phenyl)acetic acid (Compound 5.5, 0.3 mmol), DIC (0.63 mmol), DMAP/TsOH salt (58 mg, 0.2 mmol) in DCM (10 mL) will be stirred at room temperature overnight. The resulted solution was loaded on silica gel and purified by flash chromatography using eluents of DCM/EA (0% to 10% EA). The desired peak was collected, and removal of solvent will give the product as solid. Synthesis of Compound 5
  • Compound 5.4 (2-(4-(9-bromo-1,3-dioxo-1H-xantheno[2,1,9-def]isoquinolin-2(3H)- yl)phenyl)acetic acid): A mixture of Compound 5.3 (400.0 mg, 1.1 mmol), 4- aminophenylacetic acid (329.4 mg, 2.2 mmol) and DMAP (9.3 mg, 0.080 mmol) in DMF (8 mL) was degassed at room temperature. Then the mixture was heated up to 165 °C and has been kept at this temperature for 3 hrs. TLC and LCMS showed ⁇ 95% conversion without observable side-reaction. The mixture was cooled down to 50 °C.
  • reaction mixture was heated up to 80 °C and the reaction has been kept at this temperature overnight. TLC was used to monitor the reaction. After the completion, the reaction was worked up by the addition of 0.1N HCl (150 ml) and EtOAc (150 ml). The aqueous phase was further extracted by THF (150 ml*3). The combined organic phases were dried over anhydrous Na 2 SO 4 , concentrated under rotavapor, and purified by flash chromatography, using DCM in EtOAc (0-40%, with 0.1% TFA) as an eluant to provide pure Compound 5.5 as a yellow/ yellow brown solid. 363.0 mg, 80% yield.
  • Step 1 A mixture of 2-(4-bromophenyl)-4-phenyl-1H-pyrrole (synthesized according to literature: Synlett, 2016, 27(11), 1738-1742; 1.0 g, 3.36 mmol), 2,4,6-trimethylbenzaldehyde (also referred to as mesitaldehyde, 0.249 g, 1.68 mmol) and p-TsOH•H 2 O (100 mg) in 80 mL 1,2-dichloroethane was degassed, then heated at 60 °C for 40 hr.
  • Step 3 With ice-bath cooling, triethylamine (0.85 mL, 6 mmol), and BF3-diethyl etherate (1.1 mL, 9 mmol) was added to the mixture from step 2.
  • the resulted mixture was diluted with 200 mL DCM.
  • the DCM solution was washed with 0.1N HCl aqueous solution (100 mL), and water (100 mL), then loaded on silica gel and purified by flash chromatography using eluents of DCM/ethyl acetate (0% to 50% ethyl acetate).
  • the main peak was collected and concentrated under reduced pressure to give a red solid (Compound 5.7) (150 mg, in 80.4% yield).
  • Compound 7.2 (3-(3,5-bis(trifluoromethyl)phenyl)-1-(4-methoxyphenyl)-4-nitrobutan-1- one): A mixture of Compound 7.1 (4.233 g, 11.3 mmol), nitromethane (10 mL, 186 mmol) and KOH (150 mg, 2.68 mmol) was sparged with argon for 10 min, then heated at 70 oC for 30 min. The resulted mixture was poured into 300 mL water, extracted with EA. The organic phase was collected, dried over MgSO4, then removal of solvents gave a liquid (Compound 7.2) (5.21 g, in quantitative yield).
  • Compound 7.4 (4-(3,5-bis(trifluoromethyl)phenyl)-2-(4-methoxyphenyl)-1H-pyrrole): A mixture of Compound 7.3 (10 mmol), NH4OAc (3.85 g, 50 mmol) in acetic acid (20 mL) was heated at 100 °C for 5 hours. The resulted mixture was poured into 300 mL water, extracted with EA (200 mL), washed with brine, dried loaded on silica gel, and purified with flash chromatography using eluents of hexanes/DCM (0% to 50% DCM). The main peak was collected, and the solvents were removed to give a bluish solid (2.5 g, in 65% yield).
  • Step 3 To the solution above, TEA (1.0 mL), BF 3 -Et 2 O (2 mL) was added, then heated at 50 °C for one hour. The resulted mixture was diluted with DCM (200 mL), washed with water, then loaded on silica gel and purified by flash chromatography using eluents of hexanes/DCM (0% to 50 % DCM). The desired peak was collected, and removal of solvents gave a blue solid (400mg, in 62% yield).
  • the resulted mixture was diluted with 20 mL DCM, then loaded on silica gel, and purified by flash chromatography using eluents of DCM/EA (0% to 10% EA). The main peak was collected, concentrated under reduced pressure, then triturated with MeOH to crash out the solid. After filtration and dried in air, a dark purple crystalline solid was obtained (123 mg, in 66% yield).
  • Step 2 To the solution above, DDQ (0.27 g, 01.2 mmol) was added and stirred at room temperature for 45 min. LCMS analysis indicated that the oxidation reaction has completed.
  • Step 3 To the mixture from above, TEA (0.75 mL, 5.25 mmol), BF 3 -Et 2 O (2.0 mL, 16.5 mmol) was added at room temperature. The resulted mixture was heated at 50 °C for one hour. After cooled to room temperature, the mixture was diluted with 100 mL DCM, washed with water, dried over MgSO 4 , then loaded on silica gel and purified by flash chromatography using eluents of hexanes/DCM (0% to 50% DCM).
  • the reaction mixture was stirred at room temperature and Br2 (416.26 mmol, 21.3 mL) was added. The second neck was stoppered, and the reaction mixture was heated with an aluminum heat block at 75 °C open to air over the weekend. The reaction mixture was cooled to room temperature and a solid was filtered off. The filtrate was diluted with hexanes ( ⁇ 20% of volume) and a second precipitate was filtered off. Both of these precipitates were dried in vacuo at 100 °C. Orangish solids, 10.866 g total (69.9% yield). Both had similar LCMS and NMR.
  • Compound 9.2 (2-(4-(5,11-dibromo-1,3-dioxo-1H-xantheno[2,1,9- def]isoquinolin-2(3H)- yl)phenyl)acetic acid): Compound 9.2 was synthesized from Compound 9.1 (7.000 mmol, 3.136 g), 2-(4-aminophenyl)acetic acid (14.00 mmol, 2.117 g), and DMAP (2.100 mmol, 257 mg) in anhydrous DMF (65 mL) at 160 °C in a manner similar to Compound 5.4, above.
  • Compound 9.3 (2-(4-(1,3-dioxo-5,11-bis(4-(trifluoromethyl)phenyl)-1H-xantheno[2,1,9- def]isoquinolin-2(3H)-yl)phenyl)acetic acid): Compound 9.3 was synthesized from Compound 9.2 (3.500 mmol, 2.034 g), (4-(trifluoromethyl)phenyl)boronic acid (14.00 mmol, 2.659 g), K2CO3 (19.25 mmol, 2.661 g), and Pd(dppf)Cl2 (0.0245 mmol, 179 mg) in THF (/60 mL), DMF (12 mL), and water (6 mL) with heating at 80 °C under argon atmosphere overnight.
  • Compound 10.1 (2-(4-(5,11-bis(3,5-bis(trifluoromethyl)phenyl)-1,3-dioxo-1H- xantheno[2,1,9-def]isoquinolin-2(3H)-yl)phenyl)acetic acid): Compound 10.1 was synthesized from Compound 9.2 (3.500 mmol, 2.034 g), (3,5- bis(trifluoromethyl)phenyl)boronic acid (14.00 mmol, 3.611), K 2 CO 3 (19.25 mmol, 2.661 g), and Pd(dppf)Cl2 (0.0245 mmol, 179 mg) in THF (/60 mL), DMF (12 mL), and water (6 mL) with heating at 80 °C under argon atmosphere overnight.
  • Example 3 Fabrication of a Color Conversion Film
  • a glass substrate was prepared in substantially the following manner. 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.
  • DI detergent and deionized
  • IPA isopropanol
  • PMMA poly(methyl methacrylate)
  • Toluene poly(methyl methacrylate)
  • the PMMA/chromophore solution was then spin coated onto a prepared glass substrate at 1000 RPM for 20 s.
  • the resulting wet coating had a thickness of about 10 ⁇ m.
  • Three samples each were prepared in this manner for absorption, emission/FWHM and quantum yield measurements.
  • the spin coated samples were baked in an oven at 150 °C for 5 minutes to evaporate the remaining solvent.
  • Other examples were made in a similar manner, except that a poly(butyl acrylate) solution was utilized instead of the PMMA solution.
  • the poly(butyl acrylate) (PBA) solution (average M.W. ⁇ 99,000 by GPC) was purchased from Sigma Aldrich, CAS: 9003-49-0.
  • the 1-inch X 1-inch sample was inserted into a Shimadzu, UV-3600 UV-VIS- NIR spectrophotometer (Shimadzu Instruments, Inc., Columbia, MD, USA).
  • 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 normalized absorption and emission spectrum for Compound 5 is shown in FIG. 1.
  • the normalized absorption and emission spectrum for Compound 6 is shown in FIG.2.
  • the normalized absorption and emission spectrum for Compound 7 is shown in FIG.3.
  • Quantum yield of a 1-inch X 1-inch sample prepared as described above were determined by Hamamatsu C11347 Absolute PL quantum yield spectrometer (Hamamatsu Inc., Campbell CA, USA). Wavelengths were scanned every 30 nm from 390 nm- 450 nm (as excitation wavelengths) for quantum yield measurement. A 0.5’’x 0.5’’ size film was taken out from glass for measurement. The QY results at 450 nm are reported in Table 1. The structures of the compounds in the table may be found in the description and examples above. Table 1.

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Abstract

La présente divulgation concerne un nouveau complexe photoluminescent comprenant une fraction BODIPY liée de manière covalente à un dérivé de xanthéoisoquinoline absorbant la lumière bleue, et un film de conversion de couleur et une unité de rétroéclairage l'utilisant.
PCT/US2023/062465 2022-02-18 2023-02-13 Composés émissifs cycliques contenant du bore et film de conversion de couleur les contenant WO2023158977A1 (fr)

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Citations (4)

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WO2016151068A1 (fr) * 2015-03-26 2016-09-29 Basf Se Composés de benzoxanthène et de benzothioxanthène cyanatés
EP3505592A1 (fr) * 2016-08-23 2019-07-03 FUJIFILM Corporation Particules électroluminescentes et composé
US20190300782A1 (en) * 2016-12-19 2019-10-03 Fujifilm Corporation Wavelength conversion luminescent resin composition, method for producing wavelength conversion luminescent resin composition, wavelength conversion member, and light-emitting element
WO2020053124A1 (fr) * 2018-09-11 2020-03-19 Basf Se Récepteur comprenant un collecteur luminescent pour la communication optique de données

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Publication number Priority date Publication date Assignee Title
WO2016151068A1 (fr) * 2015-03-26 2016-09-29 Basf Se Composés de benzoxanthène et de benzothioxanthène cyanatés
EP3505592A1 (fr) * 2016-08-23 2019-07-03 FUJIFILM Corporation Particules électroluminescentes et composé
US20190300782A1 (en) * 2016-12-19 2019-10-03 Fujifilm Corporation Wavelength conversion luminescent resin composition, method for producing wavelength conversion luminescent resin composition, wavelength conversion member, and light-emitting element
WO2020053124A1 (fr) * 2018-09-11 2020-03-19 Basf Se Récepteur comprenant un collecteur luminescent pour la communication optique de données

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