WO2023158976A1 - Boron-containing cyclic emissive compounds and color conversion film containing the same - Google Patents

Boron-containing cyclic emissive compounds and color conversion film containing the same Download PDF

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WO2023158976A1
WO2023158976A1 PCT/US2023/062461 US2023062461W WO2023158976A1 WO 2023158976 A1 WO2023158976 A1 WO 2023158976A1 US 2023062461 W US2023062461 W US 2023062461W WO 2023158976 A1 WO2023158976 A1 WO 2023158976A1
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complex
mmol
plc
photoluminescent
color conversion
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PCT/US2023/062461
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English (en)
French (fr)
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Shijun Zheng
Jeffrey R. Hammaker
Jie Cai
Xinliang DING
Hiep Luu
Peng Wang
Tissa Sajoto
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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
    • 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
    • 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
    • H01L25/00—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof
    • H01L25/03—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes
    • H01L25/04—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes the devices not having separate containers
    • H01L25/075—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes the devices not having separate containers the devices being of a type provided for in group H01L33/00
    • H01L25/0753—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes the devices not having separate containers the devices being of a type provided for in group H01L33/00 the devices being arranged next to each other

Definitions

  • the gamut or color 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
  • RGB TM Red Green Blue
  • 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.
  • FWHM full width half maximum
  • 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 dyes 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 film of the present disclosure reduced 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 xanthenoisoquinoline derivative; a linker complex comprising an unsubstituted ester or a substituted ester; and a boron-dipyrromethene (BODIPY) moiety.
  • the linker complex may covalently link the 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.
  • the BODIPY moiety absorbs the energy from the xanthenoisoquinoline derivative and emits a light energy of a second higher wavelength.
  • the photoluminescent complex has an emission quantum yield greater than 80%.
  • the photoluminescent complex may have an emission band with a full width half maximum [FWHM] of up to 40 nm.
  • the photoluminescent complex may have a stoke 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 photoluminescent complex may have a formula:
  • the xanthenoisoquinoline derivative may be of the following general formula: , wherein R 9 is H, C 1 -C 4 alkyl group, or an optionally substituted aryl group, wherein the substituted functional group may be an optionally substituted C 1 -C 3 methyl group, e.g., trifluoromethyl (-CF 3 ).
  • Some embodiments include a color conversion film comprising: a transparent substrate layer; a color conversion layer; and at least one photoluminescent complex.
  • the color conversion layer may comprise a resin matrix.
  • the at least one photoluminescent complex is dispersed within the resin matrix.
  • the resin matrix may comprise poly(butyl acrylate).
  • the color conversion film may comprise a thickness between 10 ⁇ 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 includes a color conversion film that may absorb blue light in the 15 400 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 a 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 comprising a color conversion film described herein.
  • Some embodiments include a display device comprising the backlight unit described herein.
  • the present application provides a photoluminescent complex’s having excellent color gamut and luminescent properties, a method for manufacturing a color conversion film comprising the photoluminescent complexes, and a backlight unit comprising the color conversion film.
  • FIG.1 is a graph depicting the absorption and emission spectra of one embodiment of a photoluminescent complex (PLC-1).
  • FIG.2 is a graph depicting the absorption and emission spectra of one embodiment of a photoluminescent complex (PLC-2).
  • DETAILED DESCRIPTION The current disclosure is related to photoluminescent boron-containing cyclic emissive complexes and their uses in color conversion films, backlight units, and display devices. These complexes are often more simply termed photoluminescent complexes 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 complexes 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 also includes methods for preparing the color conversion films described herein.
  • a substituted 30 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, or a C 3 -C 7 heteroalkyl.
  • alkyl group 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 includes 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 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, -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 (or30 “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 35 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 hydroxy, or carboxyl side chain on the compounds described herein may be esterified. Any suitable method may be used to prepare the esters of the present disclosure.
  • 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 color conversion film may comprise a transparent substrate layer” should be interpreted as, for example, “In some embodiments, the color conversion film comprises a transparent substrate layer,” or “In some embodiments, the color conversion film does not comprise a transparent substrate layer.”
  • the term “BODIPY,” as used herein, refers to a chemical moiety with the formula: , comprising a 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.
  • L is a linker complex.
  • xanthenoisoquinoline or “xanthenoisoquinoline derivative” or “XI” as used herein, refers to a chemical moiety with the 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 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.
  • Some embodiments include a photoluminescent complex.
  • the photoluminescent complex comprises: a blue light absorbing xanthenoisoquinoline derivative; a linker complex; and a boron-dipyrromethene (BODIPY) moiety.
  • the linker complex may covalently link the xanthenoisoquinoline derivative to the BODIPY moiety.
  • the photoluminescent complex may be represented by the formula B- L-X, wherein B is the BODIPY moiety, L is the linker complex, and X is the xanthenoisoquinoline derivative.
  • the photoluminescent complex may be represented by the following chemical formula:
  • the xanthenoisoquinoline derivative absorbs light of a first excitation wavelength and transfers energy to the BODIPY moiety, wherein the BODIPY moiety then emits a light energy of a second wavelength 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 about 50%, about 55%, about 60%, about 65%, or about 70%. about 75%, about 80%, about 85%, about 90%, or about 90%.
  • 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%), 20 0.92 (92%), 0.93 (93%), 0.94 (94%), 0.95 (95%), or up to nearly 100%.
  • Quantum yield measurements in film 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 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.
  • the FWHM is about 20 nm to about 25 nm, about 25-30 nm, about 30-35 nm, or about 35-40 nm.
  • the photoluminescent complex may have a Stokes shift that is equal to or greater than 45 nm.
  • 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. In some embodiments, 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.
  • utilizing different substituents on the BODIPY moiety may adjust the emission wavelength between about 610 nm to about 645 nm.
  • the photoluminescent complex may have an emission peak wavelength between about 610 nm to about 645 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, or any wavelength in a range bounded by any of these values.
  • 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 30 moiety of the photoluminescent complex and the xanthenoisoquinoline moiety of the photoluminescent complex may absorb light.
  • the blue light absorbing xanthenoisoquinoline moiety of the photoluminescent complex may have a peak absorption maximum wavelength between about 400 nm to about 470 nm.
  • the peak absorption may be between about 400 nm to about 405 nm, about 405-410 nm, about 35 410-415 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, or any wavelength in a range bounded by any of these values.
  • 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, 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
  • 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.
  • the photoluminescent complex has an emission quantum yield greater than 80%.
  • Some embodiments include a blue light absorbing xanthenoisoquinoline derivative (XI derivative), wherein the blue light absorbing xanthenoisoquinoline derivative may be of the following general formula: , wherein R 9 may independently be H, methyl, or an optionally substituted aryl group, and R 10 may independently be H, C 1-4 alkyl group, or an optionally substituted aryl group.
  • the optionally substituted aryl group may be a substituted phenyl or benzyl group.
  • the aryl group may be substituted with a trifluoromethyl moiety.
  • the substituted aryl group may be ,
  • the linker complex L covalently links the blue absorbing xanthenoisoquinoline derivative with the BODIPY moiety.
  • the linker complex may be adjusted to optimize the spatial distance between the blue light absorbing xanthenoisoquinoline derivative and the BODIPY moiety. By adjusting the spatial distance between the xanthenoisoquinoline derivative and the BODIPY moiety, the quantum yield may be improved.
  • the distance separating the blue light absorbing xanthenoisoquinoline derivative and the BODIPY moiety may be about 8 ⁇ or greater.
  • the linker complex may maintain a distance between the blue light absorbing xanthenoisoquinoline derivative and the BODIPY moiety.
  • the linker complex may comprise a single bond between the xanthenoisoquinoline derivative and the BODIPY moiety.
  • the linker complex may comprise an optionally substituted C 1 - C 6 ester group.
  • the linker complex may include one of the following structures: 20 , , .
  • the linker complex may comprise an unsubstituted ester group.
  • the linker complex may comprise one of the following structures: , , , the linker complex may comprise a substituted ester linker.
  • the substituted ester linker may comprise one of the following structures: .
  • the photoluminescent complex of the current disclosure may comprise a BODIPY moiety.
  • the BODIPY moiety may have the following general formula:
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 may be independently selected from H, C 1 -C 3 alkyl, aryl, ester, or an ether.
  • R 7 and R 8 may be independently selected from H or a methyl group (-CH 3 ).
  • R 2 and R 5 may be independently selected from H or a C 1 -C 12 ester.
  • R 2 and/or R 5 may comprise one of the following structures: ,
  • the BODIPY moiety of the present disclosure may be a BODIPY moiety wherein R 3 and R 4 may each be an optionally substituted aryl group, e.g., a phenyl group; R 1 , R 2 , R 5 and R 6 may be independently H, a substituted aryl group (e.g., an optionally substituted phenyl group) such as , a diphenyl group and/or a C 2 -C 10 alkyl ether substituted phenyl group (e.g. 10).
  • 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:
  • Some embodiments include a color conversion film, wherein the color conversion film comprises: 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 the color conversion film which may be about 1 ⁇ m to about 200 ⁇ m thick.
  • the color conversion film may be described as having a thickness of about 1 ⁇ m to about 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 and may emit light in the range of about 610 nm to about 645 nm. In other embodiments, the color conversion film may emit light in the 610 nm to about 645 nm range.
  • the color conversion film may 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 20 not particularly limited and one skilled in the art would be able to choose a transparent substrate from those used in the art.
  • 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)), PBE (polybutylene terephthalate), PTT (polytrimethylene terephthalate), PBA (polybutybutylene
  • a suitable polymer may be [HAB5], (Nitto Denko, Osaka, Japan). Any of the aforedescribed resins may be corresponding/respective monomers and/or polymers.
  • 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 butyl acrylate. In some embodiments, the binder resin may be a copolymer mixture 30 comprising 50 %, 75%, 95% butyl acrylate [co-polymers]. It is believed that, compared to PMMA, the Poly(butyl acrylate) (PBA) matrix may provide a more non-polar environment (having n-butyl alkyl chains in the structure). It is believed that the non-polar environment in PBA may cause chromophore dyes to aggregate/ stack more with each other within the matrix that may lead to charge transfer, as a result, a lower quantum yield is generally obtained in 35 PBA.
  • PMMA polymethacrylate
  • the binder resin may comprise butyl acrylate.
  • the binder resin may be a copolymer mixture 30 comprising 50 %, 75%, 95% butyl acrylate [co-polymers]. It is believed that
  • 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; propylene glycol and its derivatives, such as propylene glycol monomethyl 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, the device may comprise the backlight unit described hereinto.
  • each numerical parameter should at least be construed in light of the number of reported significant 30 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 35 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 a 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 C 1 -C4 alkyl group, or an optionally substituted aryl group.
  • Embodiment 3 The photoluminescent complex of embodiment 2 wherein the optionally substituted aryl group comprises , 20 Embodiment 4
  • 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, C 1 -C 3 alkyl, aryl, ester and / or an ether; and wherein R 7 , and R 8 can be independently selected from a bond, H, or a methyl group (-CH 3 ); and wherein L1 a linker complex, wherein the linker complex is an unsubstituted ester or substituted ester.
  • Embodiment 5 The photoluminescent complex of embodiment 4, wherein R 3 and R 4 can each be an aryl group, e.g., a phenyl group.
  • Embodiment 6 The photoluminescent complex of embodiments 5, wherein the aryl group can be a phenyl group.
  • Embodiment 7 The photoluminescent complex of embodiments 6, wherein the phenyl group comprises , or a diphenyl group
  • Embodiment 8 The photoluminescent complex of embodiment 4 wherein the ether can be a C 2 -C 10 alkyl ether group
  • Embodiment 9 The photoluminescent complex of embodiment 4, wherein R 2 and R 5 can each be an ester group.
  • Embodiment 10 The photoluminescent complex of embodiment 9, wherein the ester group can be a C 1 -C 12 ester Embodiment 11
  • Embodiment 12 The photoluminescent complex of embodiment 1, wherein the unsubstituted ester linker comprises 10
  • Embodiment 13 The photoluminescent complex of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, wherein the substituted ester of the linker complex is one of the following structures: or Embodiment 14
  • the photoluminescent complex of embodiment 1, wherein the photoluminescent complex is one of the following structures: 5 , PLC-1
  • Embodiment 15 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 complex comprises the photoluminescent compound of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, dispersed within the resin matrix.
  • Embodiment 16 The color conversion film of embodiment 15, wherein the resin matrix comprises polybutyl acrylate.
  • Embodiment 17 The color conversion film of embodiment 15, further comprising a singlet oxygen quencher.
  • Embodiment 18 The color conversion film of embodiment 15, further comprising a radical scavenger.
  • Embodiment 19 The color conversion film of embodiment 15, wherein the film has a thickness of between 10 ⁇ m and 200 ⁇ m.
  • Embodiment 20 The color conversion film of embodiment 15, wherein the film absorbs light in about 400 nm to about 480 nm wavelength range and emits light in the 575 nm to about 645 nm wavelength range.
  • Embodiment 21 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, 12, 13, or 14, and a binder resin within a solvent; and applying the mixture to one of the transparent substrates opposing surfaces.
  • Embodiment 22 The method of embodiment 21, wherein the binder resin comprises polybutyl acrylate (HAB5).
  • Embodiment 23 A backlight unit comprising the color conversion film of embodiment 15, 16, 17, 18, 19, or 20.
  • Embodiment 24 A display device comprising the back-light unit of embodiment 23.
  • Example 1.1 Comparative example 1 CE-1: 0.75 g of 4-hydoxyl-2,6-dimethylvenzaldehyde (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 1.2 Comparative Example 2 (CE-2): 25 Comparative Example 2 was synthesized as described in Wakamiya, Atsushi et al. Chemistry Letters, 37(10), 1094-1095; 2008.
  • Example 2 Synthesis of Photoluminescent Complexes Synthesis of Compound PLC-1 Compound PLC-1.1: A mixture of 4-bromo-1,8-naphthalic anhydride (2.77g, 10 mmol), 4-bromo-2-nitrophenol (3.27g, 15 mmol) was degassed under vacuum for 30 min, then anhydrous NMP (50 mL) was added, followed by addition of sodium hydroxide (0.2 g, 5mmol) and copper powder (0.318 g, 5 mmol).
  • Compound PLC-1.2 A mixture of PLC-1.1 (1.5 g, 3.6 mmol), iron powder (0.60 g, 10.8 mmol) in acetic acid (50 mL) was heated at 125 C for 30 min. After cooled to room temperature, to the mixture, 100 mL water was added while stirring. The resulted mixture was filtered and washed with water, dried in air and vacuum to give a solid (1.35 g, in 82% yield).
  • 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 the pure PLC-1.5 as a yellow/yellow brown solid.363.0 mg, 80% yield.
  • Compound PLC-3.5 A mixture of PLC-3.4 (649 mg, 1.23 mmol), 4- (trifluoromethyl)phenylboronic acid (467 mg, 2.46 mmol), Pd(dppf)Cl 2 (45 mg, 0.06 mmol), potassium carbonate (345 mg, 2.5 mmol) in cosolvents of THF/DMF/water (30mL/6mL/3mL) was degassed, then heated at 80 oC for overnight. The mixture was worked up with 300mL ethyl acetate and 50 mL 0.6 N hydrochloric acid aqueous solution. The aqueous phase was extracted with ethyl acetate (150 mL x 3).
  • Compound PLC-3 A mixture of PLC-1.6 (77.5 mg, 0.1 mmol), 4-(4-(1,3-dioxo-9-(4- (trifluoromethyl)phenyl)-1H-xantheno[2,1,9-def]isoquinolin-2(3H)-yl)phenyl)butanoic acid (100 mg, 0.17 mmol), DIC (0.1 mL, 0.63 mmol), DMAP/p-TsOH (29 mg, 0.1 mmol) in DCM (8 mL) was stirred at room temperature overnight, then diluted with 10 mL DCM and loaded on silica gel and purified by flash chromatography using eluents of DCM/EA (0% to 5% EA).
  • Compound PLC-4.2 (1-(4-(tert-butyl)phenyl)-4-nitro-3-phenylbutan-1-one): Compound PLC-4.2 was synthesized from Compound PLC-4.1 (9.018 mmol, 2.384 g) and KOH (1.804 mmol, 101 mg)) in 200 proof ethanol (11 mL) and nitromethane (11 mL) at 95 ° C for one hour in a manner similar to PLC-2.2 (vide infra). The crude reaction mixture was partitioned between water (100 mL) and EtOAc (100 mL). A small amount of NaCl was added to break the emulsion.
  • the combined organic phase was washed with 10% (w/w) Na 2 CO 3 in H 2 O and then brine. After dried over anhydrous Na 2 SO 4 , the solution was concentrated under vacuum rotavapor to provide desired product PLC-4.3 as an oil, which was used for the next step without further purification.
  • the crude product was verified by LCMS and NMR as the dimethyl acetal.
  • the crude acetal was dissolved in acetic acid (15 mL) and treated with ammonium acetate (33.155 mmol). After heating overnight at 100 ° C, the reaction mixture was cooled to room temperature and water was added. The resulting precipitate was filtered off, dissolved in DCM, dried over MgSO 4 .
  • PLC-4.5 (4-(3,7-bis(4-(tert-butyl)phenyl)-5,5-difluoro-1,9-diphenyl-5H- 4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-10-yl)-3,5-dimethylphenol):
  • PLC-4.5 was synthesized from PLC-4.4 (1.00 mmol, 275 mg), and 4-hydroxy-2,6-dimethylbenzaldehyde (0.500 mmol, 75 mg) ), and pTsOH.H 2 O (0.200 mmol, 38 mg), then DDQ (0.850 mmol, 193 mg) and 2X Et3N (4.00 mmol, 0.56 mL) and BF 3 .OEt 2 (6.00 mmol, 0.74 mL) in dry DCE (50 mL) at 60 °C, then 50 °C in a manner similar to PLC-2.5
  • the crude reaction mixture was diluted with hexanes and loaded onto ⁇ 20g of silica gel in a loader. Purified by flash chromatography on silica gel (120g, solid load, equilibrate 0% EtOAc/hexanes, eluting 0% (2 CV) to 20% EtOAc/hexanes (20 CV)). Fractions containing product were evaporated to dryness in vacuo. Gives a deep red solid, 219 mg (30% yield).
  • PLC-2.1 ((E)-1-(4-isobutylphenyl)-3-phenylprop-2-en-1-one): PLC-2.1 was synthesized from 1-(4-isobutylphenyl)ethan-1-one (19.57 mmol, 3.540 g), benzaldehyde (19.57 mmol, 2.077 g), and 5N NaOH/water (23.48 mmol, 4.70 mL) in 200 proof EtOH (10 mL) 5 and water (4.70 mL) in the same manner as PLC-4.1. Gives an off-white solid, 4.844 g (94% yield).
  • PLC-2.2 (1-(4-isobutylphenyl)-4-nitro-3-phenylbutan-1-one): PLC-2.2 was synthesized from PLC-4.1 (18.323 mmol, 4.844 g) and KOH (2.346 mmol, 137 mg) in nitromethane (15 mL) and 200 proof ethanol (15 mL) at 95 ° C in the same manner as PLC- 4.2. The reaction mixture was worked up in the same manner as PLC-4.2 to give a brown oil (which solidified very slowly at room temperature), 5.753 g (97% yield).
  • PLC-2.3 (2-(4-isobutylphenyl)-4-phenyl-1H-pyrrole): PLC-2.3 was synthesized from PLC-2.2 (17.670 mmol, 5.570 g) and KOH (45.765 mmol, 2.568 g) in dry THF (200 mL) and dry methanol (100 mL), then 96% H 2 SO 4 (22 mL) and dry MeOH (100 mL) at 0 ° C in the same manner as PLC-4.3. The crude product was purified in the same manner as PLC-4.3. Gives a blue-purplish solid, 2.981 g (61% yield from PLC-2.2).
  • reaction solution was poured into crashed ice and was extracted with EtOAc (150 ml *3).
  • the combined organic phase was washed with 10% (w/w) Na 2 CO 3 in H 2 O and then brine. After dried over anhydrous Na 2 SO 4 , the solution was concentrated under vacuum rotavapor to provide PLC-5.3 as a brown oil, which was used for the next step without further purification.
  • reaction mixture was sparged with Ar for 30 minutes, then p-TsOH•H 2 O (38.0 mg, 0.2 mmol) was added.
  • the reaction solution was heated up to 60 oC and has been kept at this temperature overnight.
  • DDQ 412.0 mg, 1.8 mmol
  • the reaction was kept at room temperature for 30 minutes.
  • BF 3 •OEt 2 (0.84 mL, 6.8 mmol) and Et 3 N (0.63 mL, 4.6 mmol) were added at room temperature.
  • the reaction mixture was heated up to 50 oC and has been kept at this temperature for 1 hour.
  • Compound PLC-10.1 (6-(4-(tert-butyl)-2-nitrophenoxy)-1H,3H- benzo[de]isochromene-1,3-dione): A 1 L 2N round bottom flask was placed in an aluminum heat block and charged with a stir bar. The flask was fitted with a finned condenser/gas 5 adapter, stopper, and flow control valve. The system was flushed with argon.
  • the reaction mixture was cooled to room temperature and treated with water (175 mL) and 1N HCl (44 mL). The reaction mixture was stirred for 30 minutes, then filtered off, washing with water. The precipitate was transferred to a flask with acetone/DCM and evaporated to dryness, then azeotroped with toluene.
  • the crude product was dissolved in a small amount of DCM and treated with methanol (300 mL). The DCM and some of the methanol were removed by rotary evaporation with a hot water bath (80 °C). When all of the DCM was removed, the mixture was cooled to room temperature and the solid was filtered off. Gives a tan powder, 8.180 g (52% yield).
  • the mixture was stirred at room temperature for a few minutes, then placed in an ice-water bath and stirred for ⁇ 1 minute.
  • the NaNO 2 was 35 added over a period of a period of ⁇ 10 minutes.
  • the diazo solution was stirred at 0 ° C for 1 hour. While the diazo solution was stirring, prepared a 250 mL 2N round bottom flask with a large stir bar. The flask was fitted with a finned condenser and a dropping funnel. The flask was clamped by the off-center neck and the dropping funnel was placed in the off-center neck, so the solution would hit the top of the vortex when stirring.
  • Compound PLC-13.2 (6-(2-aminophenoxy)-1H,3H-benzo[de]isochromene-1,3- dione): A mixture of PLC-13.1 (2.0 g, 6 mmol) and iron powder ( ⁇ 10 um, 0.91 g, 16 mmol) in acetic acid (75 mL) was heated to reflux for 30 min. The resulting solution was poured into water (220 mL). The resulted precipitate was collected by filtration and washed with water and dried thoroughly in air then under vacuum to afford a yellow solid (1.65 g, in 90% yield). Confirmed by LCMS (APCI): calcd for C 18 H 12 NO 4 (M+H): 306.1; Found: 306.
  • Compound PLC-13.6 (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): A 250 mL 2N round bottom flask was charged with a stir bar and fitted with a finned condenser/gas adapter and flow control. The system was flushed with argon.
  • Example 3 Fabrication of Thin Films for Optical Properties Evaluations
  • 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.
  • IPA isopropanol
  • 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 25 wt% solution of Poly(methylmethacrylate) (PMMA) (average M.W.
  • PLC-1 and PLC-2 were also prepared in poly(butyl acrylate) (PBA), where a PBA solution was utilized instead of the PMMA solution.
  • PBA poly(butyl acrylate)
  • the poly(butyl acrylate) (PBA) solution (average M.W. ⁇ 99,000 by GPC) was purchased from Sigma Aldrich, CAS: 9003-49-0.
  • the data for PLC-1 and PLC-2 prepared in PBA is shown in Table 2 and Table 3 below.
  • 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 resulting absorption/emission spectrum for PLC-1 is shown in FIG.1.
  • the resulting absorption/emission spectrum for PLC-2 is shown in FIG.2.
  • 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 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.
  • Table 1 The maximum emission and FWHM are shown in Table 1.
  • 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.
  • Table 1 The results of the film characterization (absorbance peak wavelength, FWHM, and quantum yield) are shown in Table 1. Table 1.
  • Table 1 the results of the quantum yield of the PMMA films and the PBA/AA films as described above are provided in Tables 2 and 3 below: Table 2 Table 3

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