WO2022178450A1 - Composés émissifs cycliques contenant du bore et film de conversion de couleur le contenant - Google Patents

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

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WO2022178450A1
WO2022178450A1 PCT/US2022/017373 US2022017373W WO2022178450A1 WO 2022178450 A1 WO2022178450 A1 WO 2022178450A1 US 2022017373 W US2022017373 W US 2022017373W WO 2022178450 A1 WO2022178450 A1 WO 2022178450A1
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mmol
plc
compound
dcm
complex
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PCT/US2022/017373
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English (en)
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Shijun Zheng
Jeffrey R. Hammaker
Hiep Luu
Peng Wang
Jie Cai
Xinliang DING
Tissa Sajoto
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Nitto Denko Corporation
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Priority to CN202280009460.3A priority Critical patent/CN117063288A/zh
Priority to JP2023545963A priority patent/JP2024511260A/ja
Priority to KR1020237022623A priority patent/KR20230147045A/ko
Publication of WO2022178450A1 publication Critical patent/WO2022178450A1/fr

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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
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • 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
    • C09K2211/18—Metal complexes
    • C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
    • 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
    • H01L33/504—Elements with two or more wavelength conversion 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
    • H01L33/507—Wavelength conversion elements the elements being in intimate contact with parts other than the semiconductor body or integrated with parts other than the semiconductor body

Definitions

  • the gamut In color reproduction 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 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. It is believed that a device which could provide a wider gamut could enable the display to portray more vibrant colors.
  • LEDs Current light emitting diodes
  • FWHM full width half maximum
  • quantum dots are extremely toxic and are banned from use in many countries due to health safety issues.
  • non-cadmium-based quantum dots have a very low efficiency in converting blue LED light to green and red light.
  • quantum dots require expensive encapsulating processes for protection against moisture and oxygen.
  • the cost of using quantum dots is high, because of the difficulties in controlling size uniformity during the production process. Therefore, there exists a need for improving performance in color conversion films, backlight units, and display devices.
  • 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, e.g., with a 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 can 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, wherein the photoluminescent complex may comprise: a blue light absorbing moiety; a linker complex wherein the linker complex is an substituted ester, a unsubstituted ester, a substituted ether, or a unsubstituted ether; and a boron- dipyrromethene (BODIPY) moiety.
  • the blue light absorbing moiety is a xanthenoisoquinoline derivative.
  • the linker complex can covalently link the xanthenoisoquinoline derivative to the BODIPY moiety.
  • the xanthenoisoquinoline derivative absorbs light 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 blue light absorbing moiety is a naphthalimide derivative.
  • the linker complex can covalently link the naphthalimide derivative to the BODIPY moiety.
  • the naphthalimide derivative absorbs light of a first excitation wavelength and transfers an energy to the BODIPY moiety.
  • the BODIPY moiety absorbs the energy from the naphthalimide derivative and emits a light energy of a second higher wavelength.
  • the photoluminescent complex has an emission quantum yield greater than 80%. In some embodiments, the photoluminescent complex can have an emission band with a full width half maximum [FWHM] of up to 40 nm. In some embodiments, the photoluminescent complex can have a Stokes shift, the difference between the excitation peak of the blue light absorbing moiety and the emission peak of the BODIPY moiety, of equal to or greater than 45 nm.
  • the xanthenoisoquinoline derivative can be of the following general formula: , wherein each R 0 and R 10 may independently be a hydrogen (H), a C 1 -C 4 alkyl g oup, a t uo o ethyl group, an alkoxy group, -(OCH 2 CH 2 ) n -OCH 3 (wherein n is 1, 2, 3, or 4), or an optionally substituted aryl group.
  • R 0 and R 10 may independently be a hydrogen (H), a C 1 -C 4 alkyl g oup, a t uo o ethyl group, an alkoxy group, -(OCH 2 CH 2 ) n -OCH 3 (wherein n is 1, 2, 3, or 4), or an optionally substituted aryl group.
  • the naphthalimide derivative can be of the following general formula: , wherein each R 0 and R 10 may independently be a hydrogen (H), a C 1 -C 4 alkyl g roup, a trifluoromethyl group, an alkoxy group, -(OCH2CH2)n-OCH3 (wherein n is 1, 2, 3, or 4), or an optionally substituted aryl group
  • the BODIPY moiety can be of the following general formula:
  • R 1 and R 6 may independently be a hydrogen (H), an alkyl group, or an alkene group.
  • R 3 and R 4 may be a C 1 - C 2 alkyl.
  • R 7 and R 8 may be a hydrogen (H), a methyl group, a halide, or a C 1 -C 3 alkoxy group.
  • the color conversion film may comprise: a color conversion layer; wherein the color conversion layer includes a resin matrix; and a photoluminescent complex, as described herein, dispersed within the resin matrix.
  • the color conversion film may have a thickness between 1 ⁇ m to about 200 ⁇ m.
  • the color conversion film of the present disclosure can absorb blue light in the 400 nm to about 480 nm range and emit light in the 500 nm to about 560 nm wavelength range.
  • Another embodiment includes a color conversion film that can absorb blue light in the 400 nm to about 480 nm range and emit light in the 575 nm to about 645 nm wavelength range.
  • the color conversion film can 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.
  • the color conversion film of the present disclosure may comprise a singlet oxygen quencher.
  • the color conversion film may further comprise a radical scavenger.
  • Some embodiments include a method for preparing the color conversion film, the method comprises: dissolving an aforedescribed photoluminescent complex and a binder resin within a solvent; and applying the mixture on one of the transparent substrates opposing surfaces.
  • Some embodiments include a backlight unit including a color conversion film described herein.
  • Some embodiments include a display device including the backlight unit described herein.
  • FIG.1 is a graph depicting the absorption spectra of one embodiment of a photoluminescent complex (PLC-1).
  • FIG.2 is a graph depicting the emission spectra of one embodiment of a photoluminescent complex (PLC-1).
  • FIG.3 is a graph depicting the absorption and emission spectra of one embodiment of a photoluminescent complex (PLC-2) DETAILED DESCRIPTION
  • PLC-2 photoluminescent complex
  • the present disclosure is related to photoluminescent compounds and complexes for use in color conversion films, backlight units, and display devices.
  • the current disclosure describes photoluminescent complexes and their uses in color conversion films.
  • the 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 can both enhance the transmission of a desired first emissive bandwidth and decrease the transmission of a second emissive bandwidth.
  • a color conversion film can enhance the contrast or intensity between two or more colors, increasing the distinction from one another.
  • the present disclosure includes a photoluminescent complex that can enhance the contrast or intensity between two colors, increasing their distinction from one another.
  • a compound or chemical structure when referred to as being “substituted” it can include one or more substituents.
  • 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.
  • the substituent groups may be independently selected from an optionally substituted alkyl, alkenyl, or a C3-C7 heteroalkyl.
  • An alkyl moiety may be branched, straight chain (i.e., unbranched), or cyclic.
  • the alkyl moiety may have 1 to 8 carbon atoms.
  • the alkyl group of the compounds designated herein may be designated as “C 1 -C 8 alkyl” or similar designations.
  • “ C 1 -C 8 alkyl” indicates that there are 1, 2, 3, 4, 5, 6, 7, or 8 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, and any isomers thereof.
  • C 1 -C 8 alkyl includes C 1 -C 2 alkyl, C 1 -C 3 alkyl, C 1 -C 4 alkyl, C 1 - C 5 alkyl, C 1 -C 6 alkyl, C 1 -C 7 alkyl, and C 1 -C 8 alkyl.
  • Alkyl groups can 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 can be formed from five, six, seven, eight, nine, or more than nine atoms. Aromatic rings can be optionally substituted.
  • aromatic includes both carbocyclic aryl (e.g., phenyl) and heterocyclic aryl (or “heteroaryl” or heteroaromatic”) group (e.g., pyridine).
  • the term includes monocyclic or fused-ring polycyclic (i.e., rings which share adjacent pairs of carbon atoms) groups.
  • hydrocarbon ring refers to a monocyclic or polycyclic ring or ring system that contains only carbon and hydrogen and may be saturated.
  • Monocyclic hydrocarbon rings include groups having from 3 to 12 carbon atoms.
  • Illustrative examples of monocyclic groups include the following moieties: , and the like.
  • Illustrative examples of polycyclic groups include the following moieties: y p , y p , y , tetrahydropentalene].
  • aryl refers to an aromatic ring wherein each of the atoms forming the ring is a carbon atom.
  • Aryl rings can be formed by five, six, seven, eight, or more than eight carbon atoms.
  • Aryl groups can be substituted or unsubstituted.
  • aryl groups include, but are not limited to phenyl, naphthalenyl, phenanthrenyl, etc.
  • aralkyl refers to an alkyl group substituted with an aryl. Non-limiting aralkyl groups include benzyl, phenethyl; and the like.
  • heteroaryl refers to an aryl group that includes one or more ring heteroatoms selected from nitrogen, oxygen and sulfur, wherein the heteroaryl group has from 4 to 10 atoms in its ring system. It is understood that the heteroaryl ring can have additional heteroatoms in the ring.
  • heteroaryls that have two or more heteroatoms
  • those two or more heteroatoms can be the same or different from one another.
  • Heteroaryls can be optionally substituted.
  • An N-containing heteroaryl moiety refers to an aryl group in which a skeletal atom of the ring is a nitrogen atom.
  • Illustrative examples of heteroaryl groups include the following moieties: pyrrole, imidazole etc.
  • halogen refers to fluorine, chlorine, bromine, and iodine
  • bond refers to a chemical bond between two atoms or to two moieties when the atoms joined by the bond are considered to be part of a larger structure.
  • moiety refers to a specific segment or functional group of a molecule. Chemical moieties are often recognized chemical entities embedded in or appended to a molecule.
  • cyano or “nitrile” as used herein refers to any organic compound that contains a - CN functional group.
  • esters refers to a chemical moiety with the formula -COOR, where R comprises 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 can be esterified. Any suitable procedures and specific groups to make such esters may be utilized.
  • ether refers to a chemical moiety that contains an oxygen atom connected to two alkyl or aryl groups with the general formula of R-O-R’, where R and R’ are alkyl and/or aryl.
  • alkoxy refers to a chemical moiety that contains an oxygen atom bonded to an alkyl group that is further bonded to an alkyl or aryl group.
  • BODIPY refers to a chemical moiety with the formula:
  • the BODIPY moiety may be composed of a dipyrromethene complexed with a di-substituted boron atom, typically a BF 2 unit.
  • the IUPAC name for the BODIPY core i.e., without any substituents 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 formula: e.g., 1H-xantheno[2,1,9-def]isoquinoline-1,3(2H)-dione.
  • naphthalimide or “naphthalimide derivative” as used herein, refers to a chemical moiety with the formula: .
  • the present disclosure 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 adjusted for the absorbing luminescent moiety to transfer its energy to the acceptor luminescent moiety, wherein the acceptor luminescent moiety then emits out at a second wavelength that is larger than the absorbed first wavelength.
  • a photoluminescent complex comprises: a blue light absorbing moiety, a linker complex, and a boron-dipyrromethene (BODIPY) moiety.
  • the blue light absorbing moiety is a xanthenoisoquinoline derivative.
  • the linker complex can 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.
  • the blue light absorbing moiety is a naphthalimide derivative.
  • the linker complex can covalently link the naphthalimide derivative to the BODIPY moiety.
  • the naphthalimide 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 or naphthalimide derivative to the BODIPY moiety occurs through a Förster resonance energy transfer (FRET).
  • FRET Förster resonance energy transfer
  • the photoluminescent complex can have a high emission quantum yield.
  • the emission quantum yield can be greater than 50%, 60%, 70%, 80%, or 90%.
  • the emission quantum yield can 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 can 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 can be greater than 0.8 (80%), 0.81 (81%), 0.82 (82%), 0.83 (83%), 0.84 (84%), 0.85 (85%), 0.86 (86%), 0.87 (87%), 0.88 (88%), 0.89 (89%), 0.9 (90%), 0.91 (91%), 0.92 (92%), 0.93 (93%), 0.94 (94%), or 0.95 (95%), and may be up to nearly 1 (100%).
  • the photoluminescent complex has an emission band, the emission band can 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 photoluminescent complex can 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 blue light absorbing moiety and the emission peak of the BODIPY moiety.
  • the photoluminescent complex of the current disclosure can have a tunable emission wavelength. By substituting in different substituents to the BODIPY moiety the emission wavelength can be tuned between about 500 nm to about 560 nm or any number bound by this range.
  • the blue light absorbing moiety can have a peak absorption maximum between about 400 nm to about 470 nm wavelength.
  • the peak absorption can be 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, or any wavelength in a range bounded by any of these values.
  • the photoluminescent complex can have an emission peak between about 500 nm and about 560 nm.
  • the emission peak can be between about 500 nm to about 515 nm, about 515 nm to about 520 nm, about 520 nm to about 525 nm, about 525 nm to about 530 nm, about 530 nm to about 535 nm, about 535 nm to about 540 nm, about 540 nm to about 545 nm, about 545 nm to about 550 nm, about 550 nm to about 555 nm, about 555 nm to about 560 nm, or any wavelength in a range bounded by any these ranges.
  • Some embodiments include the photoluminescent complex wherein the blue light absorbing xanthenoisoquinline or derivative and the BODIPY moiety’s spatial distance is adjusted through the linker complex, for transfer of the blue light absorbing xanthenoisoquinoline derivative’s energy to the BODIPY moiety.
  • Other embodiments include the photoluminescent complex wherein the blue light absorbing naphthalimide derivative and the BODIPY moiety’s spatial distance is adjusted through the linker complex, for transfer of the blue light absorbing naphthalimide derivative’s energy to the BODIPY moiety.
  • the present disclosure includes a photoluminescent complex (PLC), wherein the photoluminescent complex may comprise a blue light absorbing xanthenoisoquinoline derivative, a linker complex, and a 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, wherein the blue light absorbing xanthenoisoquinoline derivative may be of the following general formula: , wherein, R 0 and R 10 may be a hydrogen (H), a C 1 -C 4 alkyl group (e.g. methyl, n-butyl, t-butyl, etc.), a trifluoromethyl group, an optionally substituted aryl group, -(OCH 2 CH 2 )n-OCH 3 , wherein n is 1, 2, 3, or 4, or an alkoxy group.
  • R 0 and R 10 may be a hydrogen (H), a C 1 -C 4 alkyl group (e.g. methyl, n-butyl, t-butyl, etc.), a trifluoromethyl group, an optionally substituted aryl group, -(OCH 2 CH 2 )n-OCH 3 , wherein n is 1, 2, 3, or 4,
  • R 10 is C 1-4 alkyl, such as methyl, ethyl, n-propyl, isopropyl, butyl, t-butyl, etc. In some embodiments, R 10 is t-butyl.
  • R 10 may be unsubstituted phenyl, , In some embodiments, R 10 may be unsubstituted phenyl. In some embodiments, R 10 may be In some embo 10 diments, R may be ome embodiments, R 10 may be . In some embodiments, R 10 may be some embodiments, R 10 may be . In some embodiments, R 10 may be . In some embodiments, R 10 may be . In some embodiments, R 10 may be n some embodiments, R 10 may be In some embodiments, R 10 may comprise an alkoxy moiety, including, but not limited to, methoxy (-OMe), or . In some embodiments, R 10 may be methoxy. In some embodiments, R 10 may be .
  • Some embodiments include a photoluminescent complex (PLC), wherein the photoluminescent complex may comprise a blue light absorbing naphthalimide derivative, a linker complex, and a BODIPY moiety.
  • the linker complex covalently links the blue light absorbing naphthalimide derivative and the BODIPY moiety.
  • the naphthalimide 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 naphthalimide 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 naphthalimide derivative, wherein the blue light absorbing naphthalimide derivative may be of the following general formula: , wherein R 0 and R 10 are defined as above for the xanthenoisoquinoline derivatives.
  • the linker complex covalently links the blue absorbing xanthenoisoquinoline derivative (or the naphthalimide derivative) with the BODIPY moiety.
  • the linker complex can be tuned to adjust the spatial distance between the blue light absorbing xanthenoisoquinoline derivative (or the naphthalimide derivative) and the BODIPY moiety.
  • the quantum yield maybe tuned.
  • the distance separating the blue light absorbing xanthenoisoquinoline derivative (or the naphthalimide derivative) and the BODIPY moiety can be about 8 ⁇ or less.
  • the linker complex can maintain a distance between the blue light absorbing xanthenoisoquinoline derivative (or the naphthalimide 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 can comprise a single bond between the xanthenoisoquinoline derivative and the BODIPY moiety.
  • the photoluminescent complex comprises a linker complex, wherein the linker complex covalently links the blue light absorbing naphthalimide derivative to the BODIPY moiety.
  • the linker complex can comprise a single bond between the naphthalimide derivative and the BODIPY moiety.
  • the linker complex can comprise a substituted ester, an unsubstituted ester, a substituted ether, or an unsubstituted ether.
  • the linker complex can comprise an optionally substituted ester group.
  • the linker complex comprises a substituted ester group, wherein the linker complex may have the following structure: , In some embodiments, the linker complex may comprise an unsubstituted ester group, wherein the linker complex may have the following structure: , In some embodiments, the linker complex may be: In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: -O(CH 2 ) 6 -. In some embodiments, the linker complex may be: .
  • the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: . In some embodiments, the linker complex may be: -O(CH 2 ) 6 -. In some embodiments, the linker complex may be: .
  • the photoluminescent complex of the current disclosure can comprise a BODIPY moiety.
  • the BODIPY moiety can have the following general formula:
  • R 1 and R 6 can be independently selected from a hydrogen (H), a saturated or unsaturated alkyl group, e.g., a methyl group, and / or an alkene group; wherein R 3 and R 4 can be independently selected from a C 1 -C 2 alkyl, e.g., a methyl group; wherein R 2 and R 5 , can be independently selected from a hydrogen (H), a saturated alkyl, an unsaturated alkyl, a cyano (-CN), an alkyl ester (e.g., ethyl ester, 2-ethyl-hexyl ester, 2,2,2- trifluoroeethyl ester, a glycol ester), or an aryl ester (e.g., a benzyl ester (-COOCH 2 Ph)); wherein R 7 and R 8 can be independently selected from a hydrogen (H), a C 1 -C 3 alkyl (e.g.,
  • the BODIPY moiety of the present disclosure may be a BODIPY moiety wherein R 1 , R 3 , R 4 and R 6 are each a methyl; R 2 and R 5 are may be a substituted ester group, wherein the substituted ester group comprises a C 1 -C 7 alkyl chain or a polyglycol chain;R 7 and R 8 are each a methyl; and L comprises a linker complex.
  • R 2 and R 5 may be independently , , , or .
  • R 2 is .
  • R 2 is In some embodiments, R 2 is .
  • R 2 is In some embodiments, R 2 is or In some embodiments, R 5 is In some embodiments, R 5 is .
  • R 5 is .
  • R 5 is .
  • R 5 is In some embodiments, R 5 is The photoluminescent complex of the present disclosure may be represented by the following which are provided for purpose of illustration and are in no way to be construed as limiting:
  • Some embodiments include a photoluminescent complex, wherein the photoluminescent complex comprises a blue light absorbing xanthenoisoquinoline derivative.
  • the blue light absorbing xanthenoisoquinoline derivative can comprise an organic lumiphore.
  • the xanthenoisoquinoline derivative may have a maximum absorbance in the light in the range of 400 nm to about 480 nm, about 400 nm to about 410 nm, about 410 nm to about 420 nm, about 420 nm to about 430 nm, about 430 nm to about 440 nm, about 440 nm to about 450 nm, about 450 nm to about 460 nm, about 460 nm to about 470 nm, about 470 nm to about 480 nm, or any wavelength in a range that is bounded by any of these values.
  • the photoluminescent complex can have an absorbance maximum peak of about 450 nm. In other embodiments, the blue light absorbing xanthenoisoquinoline derivative can have a maximum peak absorbance of about 405 nm. In still other embodiments, the blue light absorbing xanthenoisoquinoline derivative can have a maximum peak absorbance of about 480 nm. Some embodiments include a photoluminescent complex, wherein the photoluminescent complex comprises a blue light absorbing naphthalimide derivative. The blue light absorbing naphthalimide derivative can comprise an organic lumiphore.
  • the naphthalimide derivative may have a maximum absorbance in the light in the range of 400 nm to about 480 nm, about 400 nm to about 410 nm, about 410 nm to about 420 nm, about 420 nm to about 430 nm, about 430 nm to about 440 nm, about 440 nm to about 450 nm, about 450 nm to about 460 nm, about 460 nm to about 470 nm, about 470 nm to about 480 nm, or any wavelength in a range that is bounded by any of these values.
  • the photoluminescent complex can have an absorbance maximum peak of about 450 nm.
  • the blue light absorbing naphthalimide derivative can have a maximum peak absorbance of about 405 nm.
  • the blue light absorbing naphthalimide derivative can have a maximum peak absorbance of about 480 nm.
  • 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 comprise one or more of the complexes described herein.
  • the color conversion film which may be about 1 ⁇ m to about 200 ⁇ m thick.
  • the color conversion film has a thickness of about 1 ⁇ m to about 5 ⁇ m, about 5 ⁇ m to about 10 ⁇ m, about 10 ⁇ m to about 15 ⁇ m, about 15 ⁇ m to about 20 ⁇ m, about 20 ⁇ m to about 40 ⁇ m, about 40 ⁇ m to about 80 ⁇ m, about 80 ⁇ m to about 120 ⁇ m, about 120 ⁇ m to about 160 ⁇ m about 160 ⁇ m to about 200 ⁇ m, or any thickness in a range bounded by any value above.
  • the color conversion film can absorb light in the wavelength range of about 400 nm to about 480 nm and can emit light in the wavelength range of about 500 nm to about 560 nm.
  • the color conversion film can further comprise a transparent substrate layer.
  • the transparent substrate layer has two opposing surfaces, wherein the color conversion layer can 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.
  • transparent substrates include PE (polyethylene), PP (polypropylene), PEN (polyethylene naphthalate), PC (polycarbonate), PMA (polymethyl acrylate), 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).
  • PE polyethylene
  • PP polyprop
  • the transparent substrate may have two opposing surfaces.
  • the color conversion film may be disposed on and in physical contact with one of the opposing surfaces.
  • the side of the transparent substrates without color conversion film disposed thereon may be adjacent to a light source.
  • the substrate may function as a support during the preparation of the color conversion film.
  • the type of substrates used are not particularly limited, and the material and/or thickness is not limited, as long as it is transparent and capable of functioning as a support. A person skilled in the art could determine which material and thickness to use as a supporting substrate.
  • Some embodiments include a method for preparing the color conversion film, wherein the method comprises: dissolving a photoluminescent compound, described herein, and a binder resin within a solvent; and applying the mixture on to the surface of the transparent substrate.
  • the binder resin which can be used with the photoluminescent complex(s) includes resins such as acrylic resins, polycarbonate resins, ethylene-vinyl alcohol copolymer resins, ethylene-vinyl acetate copolymer resins and saponification products thereof, AS resins, polyester resins, vinyl chloride-vinyl acetate copolymer resins, polyvinyl butyral resins, polyvinylphosphonic acid (PVPA), polystyrene resins, phenolic resins, phenoxy resins, polysulfone, nylon, cellulosic resins, and cellulose acetate resins.
  • resins such as acrylic resins, polycarbonate resins, ethylene-vinyl alcohol copolymer resins,
  • the binder resin can be a polyester resin and/or acrylic resin.
  • the solvent which can be used for dissolving or dispersing the complex and the resin can 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
  • Some embodiments include a backlight unit, wherein the backlight unit may include the aforedescribed color conversion film.
  • Other embodiments include a display device, wherein the device may include the backlight unit described hereinto.
  • 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 can 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 moiety; a linker complex; and a boron-dipyrromethene (BODIPY) moiety; wherein the linker complex covalently links the blue light absorbing moiety and the BODIPY moiety, wherein the blue light absorbing moiety 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 blue light absorbing moiety and emits a light energy of a second higher wavelength, and wherein the photoluminescent complex has an emission quantum yield greater than 80%.
  • BODIPY boron-dipyrromethene
  • Embodiment 2 The photoluminescent complex of embodiment 1, wherein the blue light absorbing moiety is a xanthenoisoquinoline derivative.
  • Embodiment 3 The photoluminescent complex of embodiment 2, wherein the xanthenoisoquinoline derivative is of the general formula: , wherein R 0 is independently selected from hydrogen (H), C 1 -C 3 alkyl, optional substituted aryl, or optional substituted heteroaryl.
  • Embodiment 4 The photoluminescent complex of embodiment 1, wherein the blue light absorbing moiety is a naphthalimide derivative.
  • Embodiment 5 The photoluminescent complex of embodiment 4, wherein the naphthalimide derivative is of the general formula:
  • R 0 is independently selected from a hydrogen (H), a substituted or unsubstituted aryl, a -CF 3, a 3,5-bis(trifluoromethyl)phenyl ( re is no substitution for R 0 ;
  • X is independently selected from a oxygen (O) or a sulfur (S); and wherein R 1 is independently selected from a hydrogen (H), a substituted or unsubstituted aryl, a C 1 -C 5 alkyl, a phenyl, a 3,5-bis(trifluoromethyl)phenyl ( ifluoromethyl)phenyl ( ), a 4-(tert-butyl)phenyl ( ), a 4-(2-(2-(2- methoxyethoxy)ethoxy)ethoxy)phenyl ( here is no substitution for R1.
  • Embodiment 6 The photoluminescent complex of embodiment 1, wherein the BODIPY moiety is of the general formula:
  • R 1 and R 6 are independently selected from a hydrogen (H), a saturated or unsaturated alkyl group, or an alkene group; wherein R 3 and R 4 are independently selected from a C 1 -C 2 alkyl; wherein R 2 and R 5 are independently selected from a hydrogen (H), a saturated alkyl, an unsaturated alkyl, a cyano (-CN), an alkyl ester (-COOCH 2 CH 3 ), an aryl ester (-COOCH 2 Ar), or EtO 2 C; and wherein R 7 and R 8 are independently selected from a hydrogen (H), a methyl group, a halide, or a C 1 -C 3 alkoxy.
  • Embodiment 7 The photoluminescent complex of embodiment 6, wherein R 1 , R 3 , R 4 , and R 6 are independently selected from a C 1 -C 3 alkyl or a methyl group; wherein R 2 and R 5 are independently selected from a C 1 -C 3 ester group or a CH 3 CH2CO2 ester; and wherein R 7 and R 8 are independently selected from a methyl group.
  • Embodiment 8 The photoluminescent complex of embodiment 1, wherein the BODIPY moiety comprises the following structure:
  • Embodiment 9 The photoluminescent complex of embodiment 1, wherein the BODIPY moiety comprises the following structure:
  • Embodiment 10 The photoluminescent complex of embodiment 6, wherein L is a linker complex that can be substituted ester, a unsubstituted ester, a substituted ether, or a unsubstituted ether.
  • Embodiment 11 The photoluminescent complex of embodiment 10, wherein the unsubstituted ester comprises one of the following structures: or .
  • Embodiment 12 The photoluminescent complex of embodiment 10, wherein the substituted ester comprises one of the following structures: , Embodiment 13
  • Embodiment 14 The photoluminescent complex as in embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, wherein the photoluminescent complex comprises one of the following structures:
  • 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 a photoluminescent complex, wherein the photoluminescent compound comprises the photoluminescent complex as in embodiments 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, further comprising a singlet oxygen quencher.
  • Embodiment 17 The color conversion film of embodiment 15, further comprising a radical scavenger.
  • Embodiment 18 The color conversion film of embodiment 15, wherein the color conversion film has a thickness of between 10 ⁇ m and 200 ⁇ m.
  • Embodiment 19 The color conversion film of embodiment 15, wherein the color conversion film absorbs light in about 400 nm to about 480 nm wavelength range and emits light in the 500 nm to about 560.
  • Embodiment 20 A method for preparing the color conversion film as in embodiments 15, 16, 17, 18, or 19, the method comprising: dissolving the photoluminescent complex as in embodiments 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 21 A backlight unit comprising the color conversion film as in embodiments 15, 16, 17, 18, or 19.
  • Embodiment 22 A display device including the back-light unit of embodiment 21.
  • Example 1.1 Comparative example 1 (CE-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 was synthesis as described in Wakamiya, Atsushi et al. Chemistry Letters, 37(10), 1094-1095; 2008
  • Example 2 Synthesis of Photoluminescent Complexes (PLC) Synthesis of PLC-1
  • 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 RL-naphthalimide derivative PLC-3.5 as a yellow/ yellow brown solid.363.0 mg, 80% yield.
  • 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, 8.180g (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 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-5.3 A mixture of compound PLC-5.2 (100 mg, 0.165 mmol), (3,5- bis(trifluoromethyl)phenyl)boronic acid (170mg, 0.66 mmol), Pd(dppf)Cl2 (20mg, 0.027mmol) and potassium carbonate (138mg, 1 mmol) in THF/water (5 mL/0.5 mL) was degassed then heated at 80 °C for 2hrs. After cooled to room temperature, the precipitate was collected by filtration, washed with acetone, then dried in vacuum oven at 90 oC for 2hr. A yellow solid was obtained (142mg, in 94% yield).
  • 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.
  • To this flask was added CuSO 4 .5H 2 O (27.4 mmol, 6.842 g) and water (80 mL). About 15 minutes before the diazo solution was done, began heating the copper solution to 130 °C. The diazo solution was transferred to the dropping funnel when the solution reached 130 °C and began adding the diazo solution dropwise with high- speed stirring over a period of ⁇ 30 minutes.
  • PLC-10.4 was synthesized from PLC-10.3 (1.525 mmol, 525 mg), 4-(4-aminophenyl)butanoic acid (3.05 mmol, 546 mg), and DMAP (0.111 mmol, 14 mg) in a manner similar to PLC-1.
  • the crude reaction mixture was diluted with acetone (25 mL) and water (50 mL).
  • the resulting precipitate was filtered off, washing with 1:1 acetone:water.
  • the resulting solid was dried in a vacuum oven at ⁇ 110 °C. Gives a yellow solid, 738 mg (96% yield).
  • MS (APCI): calculated for C32H +H) 506; found: 506.
  • Compound PLC-10 Compound 10 was synthesized from PLC-1.1 (0.050 mmol, 25.6 mg), PLC-10.4 (0.075 mmol, 37.9 mg), DMAP.pTsOH salt (0.100 mmol, 29.4 mg), and EDC.HCl (0.075 mmol, 14.4 mg) in a manner similar to Compound 2.
  • the crude reaction mixture was diluted with hexanes (20 mL) and loaded onto ⁇ 15 g flash silica gel in a loader.
  • PLC-11.1 (7.0 g, 16.50 mmol, 1eq) was suspended in 2-MeTHF (150ml), added 4- (trifluoromethyl)benzeneboronic acid (5.648 g, 29.7 mmol, 1.8 eq), K 2 CO 3 (4.65 g, 33 mmol, 2eq), H2O (15 ml) Pd(dppf)Cl2 ⁇ DCM ( 269.5 mg, 0.33 mmol, 0.02eq).
  • Vac- Fill Argon cycle 3 times the resulting mixture was stirred & heated at 95 °C under Argon atmosphere 12 hours, the mixture was cooled to room temperature, added stirred with 1N HCl (20 ml) for 15 minutes then holding at room temperature 1 hours.
  • PLC-11.2 (73.4 mg, 0.15 mmol, 3eq) was suspended in DCM anhydrous (10.0 ml), added PLC- 12.1 (39.93 mg, 0.05 mmol, 1 eq), DMAP-pTSA (58.8 mg, 0.2 mmol, 4 eq), EDC.HCl (47.92 mg, 0.25 mmol, 5 eq), stirred at room temperature, under Argon atmosphere, 5 hours, diluted with DCM (150 ml), filtered, washed solid with 50 ml DCM, collected the filtrate, loaded onto 80 g SiO 2 column, eluting with Hex-DCM (1/1) , DCM only then 0.5% EA in DCM then washed with MeOH, gained 80 mg, yield 77%.
  • PLC-13.2 (71.62 mg, 0.15 mmol, 1.5eq) was suspended in DCM anhydrous (10.0 ml), added PLC- 12.1 (63.65 mg, 0.100 mmol, 1 eq), DMAP-pTSA (58.8 mg, 0.2 mmol, 2eq), EDC.HCl (57.5 mg, 0.3 mmol, 3 eq), stirred at room temperature, under Argon atmosphere, 5 hours, diluted with DCM (150 ml), filtered, washed the solid with 50 ml DCM, collected the filtrate, loaded onto 80 g SiO2 column, eluting with Hex-DCM (1/1), DCM only then 0.5% EA in DCM.
  • reaction mixture was stirred under argon atmosphere at room temperature for 5 minutes, then the heat block was set at 50 ° C and the reaction mixture was stirred for 6 hours at 50 °C, then room temperature over the weekend.
  • the reaction mixture was diluted with water ( ⁇ 200 mL), then extracted with ethyl ether (3 X 100 mL). The combined ether layers were washed with saturated aq. NaHCO 3 solution (50 mL), brine (50 mL), dried over MgSO 4 , filtered and evaporated to dryness in vacuo. Gives a light yellow oil (4.166 g, 114% yield). NMR indicates it is a mixture of the desired product and the starting bromo-glycol, ⁇ 57% product estimated).
  • the flask was fitted with a finned condenser/gas adapter, stopper and flow control valve. The system was flushed with argon. To the flask was added 6-bromo-1H,3H-benzo[de]isochromene-1,3- dione (60.0 mmol, 16.626 g) and 4-bromo-2-nitrophenol (120.0 mmol, 26.160g), followed by anhydrous NMP (250 mL). To the flask was added NaOH (30.0 mmol, 1200 mg) and copper (powder) (30.0 mmol, 1907 mg), followed by anhydrous NMP (250 mL).
  • the flask was stirred under argon atmosphere and the heat block was set to 170 °C and the reaction stirred at this temperature for 6 hours, then at room temperature overnight.
  • the room temperature reaction was quenched with aq. 1N HCl (60 mL).
  • the reaction mixture was transferred to a 2L Erlenmeyer flask and diluted to ⁇ 1100 mL total volume with water with vigorous stirring.
  • the slurry was stirred for one hour at room temperature, then the precipitate was filtered off, washing with water.
  • the crude product was dried by suction for about 10 minutes, then suspended in methanol ( ⁇ 350 mL) and stirred at room temperature for 45 minutes.
  • a 1L 3N 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 adapter, stopper and flow control valve.
  • the system was flushed with argon.
  • PLC-17.2 26.37 mmol, 10.923 g
  • SnCl 2 .2H 2 O 105.5 mmol, 23.799 g
  • HCl 4.0N, 263.7 mmol, 65.9 mL
  • 2MeTHF 185 mL
  • the reaction mixture was stirred under argon and the heat block was set to 90 °C.
  • the reaction mixture was stirred at 90 °C for 30 minutes, then cooled to room temperature.
  • the crude product was filtered off, washing with water.
  • the crude precipitate was boiled in methanol ( ⁇ 100 mL), then cooled to 0 °C (ice-water bath) and filtered off, washing with methanol. Then the crude product was heated to ⁇ 95 °C in toluene ( ⁇ 75 mL), then cooled to 0 °C (ice-water bath), then allowed to stand overnight and come to room temperature.
  • the precipitate was filtered off, washing with a small amount of toluene.
  • the crude product was dried by suction, then in a vacuum oven at ⁇ 110 °C. Gives a yellowish solid, 5.538 g (73% yield).
  • the flask was fitted with a finned condenser/gas adapter and flow control valve. The system was flushed with argon. To the flask was added PLC-17.4 (0.702 mmol, 250mg), 2-(4- aminophenyl)acetic acid (1.754 mmol, 265 mg), and DMAP (0.0512 mmol, 6.3 mg), followed by anhydrous DMF (10 mL). The reaction mixture was stirred under argon and the heat block set to 170 °C. The reaction mixture was stirred at 170 °C for 9 hours, then at room temperature. The crude reaction mixture was diluted with 75 mL of water.
  • PLC-18.2 was synthesized from PLC-18.1 (2.531 mmol, 1.038 g), (4- (trifluoromethyl)phenyl)boronic acid (5.062 mmol, 961 mg), K 2 CO 3 (6.960 mmol, 962 mg), and Pd(dppf)Cl2 (0.177 mmol, 130 mg) in THF/DMF/H 2 O (60 mL/12 mL/6 mL) at 80 °C for 30 minutes in a manner similar to PLC-17.6. The crude product was precipitated by adding water (100 mL), then filtering off the resulting solid, washing with water.
  • a 100 mL 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 adapter, stopper and flow control valve.
  • PLC-18.3 0.607 mmol, 300 mg
  • 4-hydroxy-2,6-dimethylbenzaldehyde 1.336 mmol, 201 mg
  • K 2 CO 3 1.215 mmol, 168 mg
  • the crude reaction mixture was diluted with water ( ⁇ 100 mL) and the precipitate filtered off, washing with water.
  • the crude product was dissolved in DCM and evaporated to dryness.
  • the crude product was re-dissolved in DCM and evaporated onto flash silica gel ( ⁇ 20 g).
  • PLC-20.2 (1.13 g, 2.5 mmol, 1eq) was suspended in DMF (10 ml), H 2 O (5 ml), added 4- trifluoromethyl) benzene boronic acid (0.949 g, 5.0 mmol, 2 eq), K 2 CO 3 (0.691 g, 5.0 mmol, 2eq), Pd(dppf)Cl2 ⁇ DCM (40.8 mg, 0.05 mmol, 0.02eq). The mixture was degassed by Vac-Fill Argon cycle 3 times, stirred & heated at 90 oC 5 hours. The reaction mixture was cooled to room temperature, water was added. The resulting mixture was hold at room temperature 12 hours.
  • Step 1 In a 50 ml vial was equipped with: septum cap, magnetic stirring bar; a mixture of compound benzyl 2,4-dimethyl-1H -pyrrole-3-carboxylate (68.55 mg, 0.41 mmol, 2.05eq), PLC-20.5 (129.93 mg, 0.2 mmol, 1 eq in 1,2-dichloroethane (DCE) anhydrous (4 ml) was bubbling with Argon and stirred at room temperature 15 minutes, 1 ml mixture of 50 ml DCE + 5 drop TFA was added in one portion. The resulting mixture was then stirred at 68 oC under Argon atmosphere for 24 hrs. LCMS shown only 50% starting materials were consumed.
  • DCE 1,2-dichloroethane
  • Step 2 The above mixture was cooled to RT, 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (0.148 g, 0.625 mmol) was added in one portion. The resulting mixture was stirred at room temperature 1/2 hour. TLC and LCMS shown starting materials were converted completely.
  • Step 3 The above mixture was cooled to 0 oC then stirred with triethylamine (0.25 ml, 3.48 mmol) for 15 minutes.
  • DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
  • Compound PLC-21.3 A mixture of PLC-21.2 (1.6 g, 3.2 mmol) and 48% aqueous HBr (30.0 ml) heated to refluxed by heating block at 130 oC for 3 days with stirring. The same volume of 48% aq HBr was added for 2 more times in the next 2 days, total amount was 90 ml. After cooling to room temperature, the mixture was poured to ice water, the solid was filtered, washed with water, dried in vacuo-oven to obtain 82% desired compound containing with unreacted SM. Gained 1.7 g greenish yellow solid, yield 96%. Product was used next step without further purification.
  • Step 1 In a 50 ml vial was equipped with: septum cap, magnetic stirring bar; a mixture of compound benzyl 2,4-dimethyl-1H -pyrrole-3-carboxylate (68.55 mg, 0.41 mmol, 2.05eq), PLC-21.4 (124.32 mg, 0.2 mmol, 1 eq in 1,2-dichloroethane (DCE) anhydrous (4 ml) was bubbling with Argon and stirred at room temperature 15 minutes, 1 ml mixture of 50 ml DCE + 5 drop TFA was added in one portion. The resulting mixture was then stirred at 68 oC under Argon atmosphere for 24 hrs LCMS shown only 50% starting materials were consumed.
  • DCE 1,2-dichloroethane
  • Step 2 The above mixture was cooled to room temperature, 2,3-Dichloro-5,6-dicyano-1,4- benzoquinone (DDQ) (0.148 g, 0.625 mmol) was added in one portion. The resulting mixture was stirred at room temperature 1/2 hour. TLC and LCMS shown starting materials were converted completely.
  • Step 3 The above mixture was cooled to 0 oC then stirred with triethylamine (0.25 ml, 3.48 mmol) for 15 minutes.
  • DDQ 2,3-Dichloro-5,6-dicyano-1,4- benzoquinone
  • Compound PLC-22 A mixture of compound PLC-22.1 (50 mg, 0.082 mmol), compound PLC1.1 (58.5 mg, 0.10 mmol), K2CO3 (20.7 mg, 0.15 mmol) in anhydrous DMF, was sonicated for 3 minuntes, then heated at 75 oC for 5 hours under argon atmosphere. The resulted mixture was diluted with 100 mL DCM, washed with 0.1N HCl aqueous solution (50 mL x 2), dried over MgSO 4 , concentrated to 50 mL then loaded on silica gel, and purified by flash chromatography using eluents of DCM/EA (0% ⁇ 5% EA).
  • Step 2 The above mixture was cooled to RT, 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (0.113 g, 0.498 mmol, 3eq) was added in one portion. The resulting mixture was stirred at room temperature 1/2 hour. TLC and LCMS shown starting materials were converted completely.
  • Step 3 The above mixture was cooled to 0 oC then stirred with triethylamine (0.462 ml, 3.48 mmol. 3.32 mmol, 20 eq) for 15 minutes. BF3 etherate (1.224 mL, 9.96mmol, 60 eq) was added dropwise.
  • DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
  • the resulting reaction mixture was sonicated at room temperature under Argon atmosphere for 10 minutes; then stirred at 60 oC for 45 minutes then stirred at RT 16 hrs. After quenching with EtOH (2 ml), the reaction mixture was concentrated by rotavapor. The residue was washed with hot water, the crude product was chromatographed by column of silica gel (80 g), eluting with DCM only (1CV) then DCM/ EtOAc (98:2) and then washed with EtOH to afford the pure title product (1643-006) as orange yellow solid (105 mg, 60 % total yield base on 1643-005 aldehyde SM).
  • Step 2 The above mixture was cooled to RT, 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (79.45 mg, 0.35 mmol) was added in one portion. The resulting mixture was stirred at room temperature 1/2 hour. TLC and LCMS shown starting materials were converted completely.
  • Step 3 The above mixture was cooled to 0 oC then stirred with triethylamine (0.125 ml, 1.74 mmol) for 15 minutes. BF3 etherate (0.71 mL, 2.76 mmol) was added dropwise.
  • DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
  • BF3•OEt2 (0.16 mL, 1.3 mmol) and Et3N (0.12 mL, 0.9 mmol) were added at room temperature. The reaction mixture was heated up to 60 oC and has been kept at this temperature for 1 hour. More BF3•OEt2 (0.16 mL, 1.3 mmol) and Et3N (0.12 mL, 0.9 mmol) were added at room temperature. The reaction mixture was heated up to 60 oC and has been kept at this temperature for 3 hours.
  • reaction mixture was cooled to room temperature and treated with water (175 mL) and 1N HCl (44 mL). The reaction was further diluted with water (325 mL) to give a sticky precipitate. The reaction mixture was decanted from the sticky precipitate, washing with water. The crude product was evaporated to dryness in vacuo, then dissolved in DCM and evaporated onto ⁇ 65g flash silica gel. Purified by flash chromatography on silica gel (330g, solid load, equilibrate 100% hexanes, eluting 100% (2 CV) ⁇ 100% DCM (20 CV)). Fractions containing product were collected and evaporated to dryness in vacuo.
  • Compound PLC-29.2 (6-(2-amino-4-(trifluoromethyl)phenoxy)-1H,3H-benzo[de]isochromene-1,3- dione)
  • Compound PLC-29.2 was synthesized from Compound PLC-29.1 (3.47 mmol, 1.400 g), (13.88 mmol, 3131 mg), 4N HCl (34.7 mmol, 8.7 mL) in 2MeTHF (30 mL) in a manner similar to the methods described above. After the usual workup, the product was sufficiently pure to use in the next step. Gives 877 mg (68% yield).
  • Compound PLC-29.3 (9-(trifluoromethyl)-1H,3H-isochromeno[6,5,4-mna]xanthene-1,3-dione)
  • Compound PLC-29.3 was synthesized from Compound PLC-29.2 (2.344 mmol, 875 mg), NaNO 2 (17.58 mmol, 1.213 g), con. HCl (11.72 mmol, 12.1N, 0.969 mL), and CuSO 4 .5H 2 O (16.06 mmol, 4.009g). The crude product was evaporated onto ⁇ 30g flash silica gel in vacuo.
  • Compound PLC-29.4 (2-(4-(1,3-dioxo-9-(trifluoromethyl)-1H-xantheno[2,1,9-def]isoquinolin-2(3H)- yl)phenyl)acetic acid)
  • Compound PLC-29.4 was synthesized from Compound PLC-29.3 (0.702 mmol, 250 mg), 2-(4- aminophenyl)acetic acid (1.754 g, 265 mg), and DMAP (0.0521 mmol, 6.3 mg) in DMF (10 mL) in a manner similar to the methods described above. After workup and trituration, the compound was dried in a vacuum oven at ⁇ 140 ° C. Gives 366 mg (107% yield).
  • Compound PLC-29 Diethyl 10-(4-(2-(4-(1,3-dioxo-9-(trifluoromethyl)-1H-xantheno[2,1,9- def]isoquinolin-2(3H)-yl)phenyl)acetoxy)-2,6-dimethylphenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H- 4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2,8-dicarboxylate
  • Compound PLC-29 was synthesized from Compound PLC-1.1 (0.050 mmol, 25.6 mg), Compound PLC- 29.4 (0.075 mmol, 37 mg), DMAP.pTsOH salt (0.100 mmol, 29.4 mg), and EDC.HCl (0.150 mmol, 28.8 mg) in a manner similar to the methods described above.
  • the crude product was diluted with hexanes and loaded onto ⁇ 30g flash silica gel in a solid loader. Purified by flash chromatography on silica gel (80g, solid load, no equilibration, eluting 100% hexanes/0.5% EtOAc modifier (2 CV) ⁇ 100% DCM/0.5% EtOAc modifier (10 CV) ⁇ 100% DCM/1% EtOAc modifier (20 CV) ⁇ 100% DCM/2% EtOAc modifier (20 CV) ⁇ 100% DCM/4% EtOAc modifier (20 CV)). Fractions containing product were evaporated to dryness in vacuo. Gives an orange solid, 46 mg (94% yield).
  • Compound PLC-32.4 4-((6-(1,3-dioxo-9-(4-(trifluoromethyl)phenyl)-1H-xantheno[2,1,9- def]isoquinolin-2(3H)-yl)hexyl)oxy)-2,6-dimethylbenzaldehyde
  • Compound PLC-32.4 was synthesized from Compound PCL-32.3 (0.200 mmol, 119 mg), 4-hydroxy-2,6- dimethylbenzaldehyde (0.300 mmol, 45 mg), and K 2 CO 3 (0.260 mmol, 36 mg) in dry DMF (10 mL). The reaction mixture was sonicated for 15 minutes, then stirred in a heating block at 65 ° C for 7 hours.
  • the crude reaction mixture was diluted with hexanes ( ⁇ 25%), then loaded onto ⁇ 5g silica gel in a loader. Purified by flash chromatography on silica gel (80g, solid load, equilibrate 70% DCM/hexanes, eluting 70% (2 CV) ⁇ 100% DCM/hexanes (5 CV) ⁇ isocratic 100% DCM/hexanes (5 CV) ⁇ 0% EtOAc/DCM (0 CV) ⁇ isocratic 0% EtOAc/DCM (5 CV) ⁇ 10% EtOAc/DCM (20 CV)). Fractions containing product were evaporated to dryness in vacuo. Gives an orange solid, 26 mg (18% yield).
  • Compound PLC-33.2 Bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl) 5,5-difluoro-10-(4-hydroxy-2,6- dimethylphenyl)-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2,8- dicarboxylate
  • Compound PLC-33.2 was synthesized from Compound PLC-33.1 (3.588 mmol, 1024 mg), 4-hydroxy- 2,6-dimethylbenzaldehyde (1.750 mmol, 263 mg), and pTsOH.H 2 O (0.175 mmol, 33 mg), then DDQ (2.975 mmol, 675 mg) and 2X Et3N (14.00 mmol, 1.95 mL) and BF3.OEt2 (14.00 mmol, 2.59 mL) in dry DCE (50 mL) at room temperature,
  • Compound PLC-35.2 Bis(2,2,2-trifluoroethyl) 5,5-difluoro-10-(4-hydroxy-2,6-dimethylphenyl)-1,3,7,9- tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2,8-dicarboxylate
  • Compound PLC-35.2 was synthesized from Compound PLC-35.1 (1.575 mmol, 348 mg), 4-hydroxy-2,6- dimethylbenzaldehyde (0.750 mmol, 113 mg), ), and pTsOH.H 2 O (0.300 mmol, 57 mg), then DDQ (1.275 mmol, 289 mg) and 2X Et 3 N (6.00 mmol, 0.84 mL) and BF 3 .OEt 2 (9.00 mmol, 1.10 mL) in dry DCE (20 mL) at 60 ° C, then 50 °
  • Compound PLC-36.1 tert-butyl 4-(2-(3-hydroxypropyl)-1,3-dioxo-2,3-dihydro-1H-xantheno[2,1,9- def]isoquinolin-9-yl)benzoate
  • Compound PLC-36.1 was synthesized from Compound 27.1 (1.30 mmol, 552 mg), (4-(tert- butoxycarbonyl)phenyl)boronic acid (2.60 mmol, 577 mg), K 2 CO 3 (3.575 mmol, 494 mg), and Pd(dppf)Cl 2 (0.0910 mmol, 67 mg) in THF (30 mL)/DMF (6 mL)/water (3 mL) at 80 ° C similar to Compound 32.2.
  • Compound PLC-37.2 Bis(2-ethylhexyl) 5,5-difluoro-10-(4-hydroxy-2,6-dimethylphenyl)-1,3,7,9- tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2,8-dicarboxylate
  • Compound PLC-37.2 was synthesized from Compound PLC-37.1 (4.20 mmol, 1056 mg), 4-hydroxy- 2,6-dimethylbenzaldehyde (2.00 mmol,300 mg), and TFA (0.200 mL), then DDQ (3.40 mmol, 772 mg) and 2X Et3N (16.00 mmol, 2.20 mL) and BF 3 .OEt 2 (24.00 mmol, 3.0 mL) in dry DCE (20 mL) at room temperature, then 50 ° C in a manner similar to Compound 32.
  • Compound PLC-38.3 4-(3-(9-(4-butylphenyl)-1,3-dioxo-1H-xantheno[2,1,9-def]isoquinolin-2(3H)- yl)propoxy)-2,6-dimethylbenzaldehyde
  • Compound 46.3 was synthesized from Compound PLC-38.2 (0.119 mmol, 75 mg), ), 4-hydroxy-2,6- dimethylbenzaldehyde (0.356 mmol, 53 mg), and K 2 CO 3 (0.332 mmol, 46 mg) in dry DMF (10 mL). The reaction mixture was sonicated for 15 minutes, then stirred in a heating block at 65 ° C for 7 hours.
  • Compound PLC-39.2 4-(3-(9-(tert-butyl)-1,3-dioxo-1H-xantheno[2,1,9-def]isoquinolin-2(3H)- yl)propoxy)-2,6-dimethylbenzaldehyde
  • Compound PLC-39.2 was synthesized from Compound 39.1 (0.601 mmol, 279 mg), 4-hydroxy-2,6- dimethylbenzaldehyde (1.802 mmol, 270 mg), and K 2 CO 3 (1.682 mmol, 232 mg) in dry DMF (15 mL). The reaction mixture was sonicated for 15 minutes, then stirred in a heating block at 65 ° C for 7 hours.
  • Compound PLC-40.2 9-(tert-butyl)-2-(2-hydroxyethyl)-1H-xantheno[2,1,9-def]isoquinoline-1,3(2H)- dione
  • Compound PLC-40.2 was synthesized from Compound PLC-40.1 (6.863 mmol, 2.776 g), NaNO 2 (51.475 mmol, 3.552 g), con HCl (34.317 mmol, 2.83 mL), and CuSO 4 .5H 2 O (46.67 mmol, 11.653 g) in a manner similar to the methods described above.
  • the crude product was ⁇ 10% acetate ester. It was cleaved with K 2 CO 3 in the same manner as Compound 52.2.
  • Compound PLC-40.3 2-(2-bromoethyl)-9-(tert-butyl)-1H-xantheno[2,1,9-def]isoquinoline-1,3(2H)- dione
  • Compound PLC-40.3 was synthesized from Compound PLC-40.2 (1.884 mmol, 730 mg), perbromomethane (2.826 mmol, 937 mg), and PPh3 (2.826 mmol, 741 mg) in dry DCM (80 mL) in a manner similar to Compound 50.3. The crude reaction mixture was loaded onto ⁇ 30g of silica gel in a loader.
  • Compound PLC4.4 4-(2-(9-(tert-butyl)-1,3-dioxo-1H-xantheno[2,1,9-def]isoquinolin-2(3H)- yl)ethoxy)-2,6-dimethylbenzaldehyde
  • Compound PLC-40.4 was synthesized from Compound PLC-40.3 (0.450 mmol, 203 mg), 4-hydroxy-2,6- dimethylbenzaldehyde (1.350 mmol, 203 mg), and K 2 CO 3 (1.260 mmol, 174 mg) in dry DMF (10 mL) in a manner similar to the methods described above. The crude product was filtered off, washed with water, dissolved in DCM, and evaporated to dryness.
  • 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(methylmethacrylate)
  • cyclopentanone 99.9% pure
  • the PMMA/lumiphore solution was then spin coated onto a prepared glass substrate at 1000 RPM for 20 s and then 500 RPM for 5 s.
  • the resulting wet coating had a thickness of about 10 ⁇ m.
  • the samples were covered with aluminum foil before spin coating to protect them from exposure to light.
  • Three samples each were prepared in this manner for each for Emission/FWHM and quantum yield.
  • the spin coated samples were baked in a vacuum oven at 80 °C for 3 hours to evaporate the remaining solvent.
  • the 1-inch X 1-inch sample was inserted into a Shimadzu, UV-3600 UV-VIS- NIR spectrophotometer (Shimadzu Instruments, Inc., Columbia, MD, USA). All device operations were performed inside a nitrogen-filled glove-box.
  • the resulting absorption/emission spectrum for PCL-1 is shown in FIGs.1 and 2, while the resulting absorption/emission spectrum for PCL-2 is shown in FIG. 3.
  • the fluorescence spectrum of a 1-inch X 1-inch film sample prepared as described above was determined using a Fluorolog spectrofluorometer (Horiba Scientific, Edison, NJ, USA) with the excitation wavelength set at the respective maximum absorbance wavelength. The maximum emission and FWHM are shown in Table 1.
  • the quantum yield of a 1-inch X 1-inch sample prepared as described above were determined using a Quantarus-QY spectrophotometer (Hamamatsu Inc., Campbell CA, USA) was excited at the respective maximum absorbance wavelength. The results are reported in Table 1.
  • the results of the film characterization (absorbance peak wavelength, FWHM, and quantum yield) are shown in Table 1 below. Table 1

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Abstract

La présente invention concerne un nouveau complexe photoluminescent comprenant une fraction BODIPY liée de manière covalente à une fraction d'absorption de lumière bleue, et un film de conversion de couleur, une unité de rétroéclairage l'utilisant.
PCT/US2022/017373 2021-02-22 2022-02-22 Composés émissifs cycliques contenant du bore et film de conversion de couleur le contenant WO2022178450A1 (fr)

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JP2023545963A JP2024511260A (ja) 2021-02-22 2022-02-22 含ホウ素環式放出性化合物及びそれを含む色変換フィルム
KR1020237022623A KR20230147045A (ko) 2021-02-22 2022-02-22 보론 함유 환상 발광성 화합물 및 이것을 포함하는색변환 필름

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WO2024081802A1 (fr) * 2022-10-14 2024-04-18 Nitto Denko Corporation Film de conversion de longueur d'onde et dispositif d'affichage le comprenant
WO2024119026A1 (fr) 2022-12-02 2024-06-06 Nitto Denko Corporation Composés émissifs cycliques contenant du bore et film de conversion de couleur le contenant
WO2024137915A1 (fr) * 2022-12-21 2024-06-27 Nitto Denko Corporation Composés émissifs cycliques contenant du bore et film de conversion de couleur les contenant

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WO2024119026A1 (fr) 2022-12-02 2024-06-06 Nitto Denko Corporation Composés émissifs cycliques contenant du bore et film de conversion de couleur le contenant
WO2024137915A1 (fr) * 2022-12-21 2024-06-27 Nitto Denko Corporation Composés émissifs cycliques contenant du bore et film de conversion de couleur les contenant

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