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WO2019025392A1 - Récupération de rendement quantique - Google Patents

Récupération de rendement quantique Download PDF

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Publication number
WO2019025392A1
WO2019025392A1 PCT/EP2018/070644 EP2018070644W WO2019025392A1 WO 2019025392 A1 WO2019025392 A1 WO 2019025392A1 EP 2018070644 W EP2018070644 W EP 2018070644W WO 2019025392 A1 WO2019025392 A1 WO 2019025392A1
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Prior art keywords
optical medium
process according
optical
quantum yield
obtainable
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English (en)
Inventor
Arjan Meijer
Christian MATUSCHEK
Itai Lieberman
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Merck Patent GmbH
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Merck Patent GmbH
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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
    • C09K11/01—Recovery of luminescent materials
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies

Definitions

  • the present invention relates to a process for quantum yield recovery of
  • the present invention further relates to an optical medium obtained or obtainable by the process for quantum yield recovery and to the use of such an optical medium in an optical device.
  • Semiconducting nanocrystals such as quantum dots, quantum rods, etc. are of great interest as color converter materials in optical devices such as light emitting diodes (LEDs) and liquid crystal displays (LCDs) due to their
  • VUV Vacuum Ultra-Violet
  • Luminescent nanocrystals undergo (oxidative) damage when exposed to oxygen, moisture, temperature and/or high intensity light resulting in a significant loss or drop of their quantum yield (QY).
  • QY quantum yield
  • the quantum yield of the encapsulated nanocrystals still degrades after a certain period of time, in particular due to the exposure to high temperature and/or high light intensity condition. Moreover, during the manufacturing process of an optical medium, exposure to these quantum yield degrading conditions very often cannot be avoided.
  • an optical medium in particular an optical medium applicable in optical devices, which comprises a nanosized fluorescent material encapsulated in an organic material and which does not attain its initial or usual quantum yield (anymore) is highly desirable.
  • Such a process would make it possible to prolong the lifetime of an optical medium and, thus, also the lifetime of an electronic devices applying such an optical medium.
  • the present inventors have surprisingly found that the quantum yield of an optical medium comprising a light luminescent part which comprises at least one nanosized fluorescent material and an organic material, the quantum yield of which has dropped due to exposure to high temperature and/or high light intensity condition, can be recovered by treating said optical medium simultaneously with heat and moisture.
  • an object of the present invention to provide a practical method capable of recovering the quantum yield of an optical medium, which comprises a light luminescent part comprising at least one nanosized fluorescent material and an organic material, easily and effectively.
  • optical medium in particular an optical medium applicable in optical devices, the quantum yield of which has been recovered using said process.
  • the present invention provides a process for quantum yield recovery of an optical medium, said process comprising at least the steps of: a) providing an optical medium comprising a light luminescent part that comprises at least one nanosized fluorescent material and an organic material; and b) heat treating and simultaneously moisture treating the optical medium by heating the optical medium in a humid environment.
  • the invention further relates to a composition
  • the invention relates to a formulation comprising at least the optical medium in the form of a capsule (200) obtained or obtainable by the process of the invention and at least one solvent.
  • the invention further relates to an optical device comprising at least the optical medium obtained or obtainable by the process of the invention.
  • Fig. 1 shows a cross sectional view of an optical medium having a film-like structure that can be treated by the process of the invention.
  • Fig. 2 shows a cross sectional view of an optical medium in the form of a light luminescent capsule that can be treated by the process of the invention.
  • Fig. 3 shows a cross sectional view of one embodiment of an optical device (300).
  • Fig. 4 shows the QY measurement results of the optical films obtained from Examples 1 to 6.
  • Fig. 5 shows the QY measurement results of the optical film obtained from Example 7.
  • Fig.6 shows the QY measurement results of the capsules-containing optical film obtained from Example 10.
  • a process for quantum yield recovery of an optical medium comprises at least the steps of: a) providing an optical medium comprising at least a light luminescent part that comprises at least one nanosized fluorescent material and an organic material; and b) heat treating and simultaneously moisture treating the optical medium by heating the optical medium in a humid environment.
  • quantum yield recovery is understood to mean that the quantum yield of an optical medium, which for any of the above- explained reasons has dropped to or is at a value lower than an initial or
  • QY usually has a QY of 70 to 75% (typical value of quantum rods in solution), has dropped for example due to exposure to high temperature and/or high light intensity condition to below 60%, or even below 40%, the QY can be recovered back to values of 70 to 75% or even more by subjecting said optical medium to the heat and moisture treatment of the present invention
  • the process of the invention is not limited by any QY values of the optical medium to be treated before or after the heat and moisture treatment. This means, within the framework of the present invention it does not matter which initial QY value the optical medium to be treated
  • the process of the invention is not limited in any way by the time Q period the optical medium to be treated has already been used. This
  • an optical medium having a reduced QY can be subjected to the process of the invention for QY recovery no matter whether it has already been in use for some time or whether it has just been prepared.
  • the optical medium of the present invention is characterized in that it comprises a light luminescent part which comprises at least one nanosized fluorescent material and an organic material.
  • the optical medium can be in the form of or processed in the form of a sheet or film, a lens or a capsule.
  • the optical medium can be an optical sheet or film, a filter or a lens, for example a color filter, color conversion sheet or remote phosphor tape.
  • sheet includes "layer” and "film” like structures.
  • light luminescent part is used herein to indicate that part of an optical medium that comprises the semiconductor light emitting nanocrystals, preferably said semiconductor light emitting nanocrystals are semiconductor fluorescent materials.
  • the nanosized fluorescent material is not specifically limited. A wide variety of publically known nanosized light emitting materials can be used as desired. It is also possible to use a mixture of more than one nanosized light emitting materials.
  • nanosized means the size in between 1 nm and 999 nm.
  • the type of shape of the nanosized light emitting material is not particularly limited.
  • spherical shaped, elongated shaped, star shaped, polyhedron shaped, banana shaped, star shaped, pyramidal shaped, tetrapod shaped, tetrahedron shaped, platelet shaped, cone shaped, and irregular shaped semiconducting nanocrystals can be used.
  • the term "a nanosized fluorescent material” is understood to mean that the light emitting material which size of the overall diameter is in the range from 1 nm to 999 nm.
  • the length of the overall structures of the fluorescent material is in the range from 1 nm to 999 nm.
  • the nanosized fluorescent material is selected from the group 10 consisting of nanosized inorganic phosphor materials, quantum sized materials such as quantum dots and or quantum rods, and a combination of any of these, and quantum sized materials are especially preferred.
  • the term “quantum sized” means the size of the
  • quantum sized materials such as quantum dot materials and quantum rod materials, can emit tunable, sharp and vivid colored light due to "quantum confinement"
  • the nanosized fluorescent material according to the present invention is more preferably a quantum sized material comprising ll-VI, III- 25 V, or IV-VI semiconductors, or a combination of any of these.
  • the semiconductor nanocrystal may be selected from InP, CdS, CdSe, CdTe, ZnS, ZnSe, ZnSeS, ZnTe, ZnO, InPZnS, InPZn, ⁇ n Cu 2 (ZnSn)S .
  • a nanosized fluorescent material also encompasses such materials having a core/shell structure.
  • core/shell structure means the structure having a core part and at least one shell part covering said core.
  • said core/shell structure can be core/one shell layer structure, core/double shells structure or core/multishell structure, wherein core/multishell structures stand for the stacked shell layers consisting of three or more shell layers and wherein each stacked shell layers of double shells and/or multishell can be made from the same or different materials.
  • the size of the overall structures of the quantum sized material is from 1 nm to 100 nm, more preferably, it is from 1 nm to 30 nm, even more preferably, it is from 5 nm to 15 nm.
  • Cds, CdSe, CdTe, ZnS, ZnSe, ZnSeS, ZnTe, ZnO, GaAs, GaP, GaAs, GaSb, HgS, HgSe, HgSe, HgTe, InAs, InP, InPZnS, InPZn, InSb, AIAs, AIP, AlSb, Cu 2 S, Cu 2 Se, CulnS2, CulnSe 2 , Cu 2 (ZnSn)S , Cu 2 (lnGa)S 4 , TiO 2 alloys and combination of any of these may be preferably used as a core of the nanosized light emitting material (120).
  • the shell of the nanosized light emitting material may preferably be selected from the group consisting of ll-VI, lll-V, or IV-VI semiconductors.
  • InP/ZnSe/ZnS, InPZn/ZnS, InPZn/ZnSe/ZnS dots or rods, ZnSe/CdS, ZnSe/ZnS or combination of any of these, can be used preferably.
  • for green emission use CdSe/CdS, CdSeS/CdZnS,
  • InP/ZnSe/ZnS, InPZn/ZnS, InPZn/ZnSe/ZnS, ZnSe/CdS, ZnSe/ZnS or combination of any of these can be used preferably.
  • blue emission use such as ZnSe, ZnS, ZnSe/ZnS, or combination of any of these, can be used preferably.
  • quantum dots publically available quantum dots, for examples, CdSeS/ZnS alloyed quantum dots product number 753793, 753777, 753785, 753807, 753750, 753742, 753769, 753866, InP/ZnS quantum dots product number 776769, 776750, 776793, 776777, 776785, PbS core-type quantum dots product number 747017, 747025, 747076, 747084, or CdSe/ZnS alloyed quantum dots product number 754226, 5 748021 , 694592, 694657, 694649, 694630, 694622 from Sigma-Aldrich, can be used preferably as desired.
  • quantum rod materials have been described, for example, in 10 WO 2010/095140 A1 .
  • the surface of the nanosized fluorescent material may be covered or coated with one or more kinds of ⁇ surface ligands.
  • the surface ligands in common use include phosphines and phosphine oxides such as Tnoctylphosphine oxide (TOPO), Tnoctylphosphine (TOP), and Tributylphosphine (TBP); phosphonic acids such as
  • DDPA Dodecylphosphonic acid
  • TDPA Tridecylphosphonic acid
  • ODPA Octadecylphosphonic acid
  • HPA Hexylphosphonic acid
  • amines such as Dedecyl amine (DDA), Tetradecyl amine (TDA),
  • HDA Hexadecyl amine
  • ODA Octadecyl amine
  • thiols such as
  • the quantum yield of an optical medium can be recovered after the quantum yield has dropped, for example because of temperature quenching, by exposing the optical medium simultaneously to a heat and moisture treatment.
  • the heat treating is preferably carried out at a temperature in the range from about 20°C to about 95°C.
  • the higher the temperature is set during the heat treatment the faster the recovering process of the optical medium progresses.
  • the temperature may not be set too high, as high temperatures may damage the optical medium depending on the materials of which it consists, thereby resulting in a performance decrease.
  • the heat treating is carried out at temperatures in the range from 70°C to 90°C, more preferably in the range from 80°C to 88°C. Most preferably, the temperature is set at 85°C.
  • the moisture treating is preferably carried out in a humid environment having a humidity in the range from 35% relative humidity (hereinafter "%-rh") to 95%-rh.
  • the humid environment has a humidity from 70%-rh to 90%-rh, more preferably from 80%-rh to 88%-rh, even more preferably it is from 83%-rh to 87%-rh Most preferably, the humidity is set at 85%-rh.
  • the quantum yield recovery process of the present invention if the heat and moisture treating is carried out at lower temperatures and humidity, for example at ambient conditions (about 23°C/50%-rh), the recovery progress is very slow, but full recovery performance can still be achieved. However, best results concerning recovery time and recovery performance were obtained if the heat and moisture treatment were carried out simultaneously at 85°C and 85%-rh.
  • any apparatus or device capable of providing the desired heat and moisture conditions can be used.
  • the optical medium to be treated is placed in a climate chamber or oven set to hold the desired temperature and humidity over a desired time period.
  • the heat and moisture treating is performed for 10 min or more, preferably from 20 min to 10 days, more preferably from 25 min to 5 days, and most preferably from 30 min to 2 days. It is particularly preferred that the heat and moisture treating is performed at 85°C and 85%-rh for 24 hours.
  • the recovery duration time strongly depends on the conditions set during heat and moisture treatment. In general, however, at certain fixed recovery conditions (i.e., fixed temperature and humidity), the recovery performance increases the longer the heat and moisture treating is performed. After a certain treatment time, however, no further increase in recovery performance is observed (i.e. a function "QY" versus
  • the optical medium (100) comprises a light luminescent part that comprises at least 0 one nanosized fluorescent material (1 10) (for example, red and/or green) and an organic material, which is a matrix material (120) encapsulating the nanocrystals (1 10).
  • a barrier layer (130) can be placed over the light luminescent part.
  • the optical medium (100) preferably has a layered or film-like structure, such as an optical film, and the
  • semiconducting crystals (1 10) are incorporated into the matrix material (120) in order to protect the nanocrystals (1 10) from external influences, ⁇ as mentioned before.
  • the nanosized fluorescent material (1 10) is not specifically limited. A wide variety of publically known nanosized light emitting materials as presented 5 before can be used as desired.
  • the matrix material according to this embodiment of the optical medium (120) is selected from polysilazanes, water soluble polymers and
  • the matrix material (120) is selected from polysilazanes such as organo-polysilazanes, water soluble polymers such as substituted or unsubstituted polyvinyl alcohols and combinations of any of these.
  • organo-polysilazane means a polysilazane comprising at least one of organic substituent in a repeating unit of said polysilazane.
  • polyvinyl alcohol unsubstituted
  • cation-substituted polyvinyl alcohols anion-substituted polyvinyl alcohols
  • acryl-substituted polyvinyl alcohols acetoacetyl substituted polyvinyl alcohols (such as GohsefimerTM Z from Nippon Gohsei ), vinyl acetates (such as ExcevalTM from Kuraray, 10 Nichigo G-PolymerTM from Nippon Gohsei), silanol substituted polyvinyl alcohols (such as R-1 130 series from Kuraray), or a combination of any of these can be used.
  • acetoacetyl substituted polyvinyl alcohols such as GohsefimerTM Z from Nippon Gohsei
  • vinyl acetates such as ExcevalTM from Kuraray, 10 Nichigo G-PolymerTM from Nippon Gohsei
  • polyvinyl alcohols acryl-substituted polyvinyl alcohols are described, for example, in JPS61 -10483 A, JPH01 -206088 A, JPS61 -237681 A, JPS63- 307979 A, JPH07-285265 A, JPH07-009758 A, and JPH08-025795 A.
  • organo-polysilazanes are used as the matrix material (120) according to this embodiment of the optical medium, which have a repeating unit represented by following general formula (I):
  • R 1 , R 2 and R 3 are, independently of each other, identically or differently selected from a hydrogen atom, an alkyl group, an alkenyl 2Q group, a cycloalkyl group, an aryl group, an alkoxy group, an amino group, a silyl group, an alkylsilyl group or an alkylamino group, and at least one of Ri, R2, R3 is a hydrogen atom, with the proviso that at least one of Ri, R2, R3 is not a hydrogen atom.
  • the at least one of R 1 , R 2 and R 3 which is not a hydrogen atom can be substituted by one or more of halogen atoms, alkyl groups, alkoxy groups, amino groups, silyl groups, and / or alkyl silyl groups.
  • halogen atoms alkyl groups, alkoxy groups, amino groups, silyl groups, and / or alkyl silyl groups.
  • dialkyl amino group alkyl amino alkyl group, alkyl silyl group, dialkyl silyl group, alkoxy silyl group, dialkoxy silyl group, trialkoxy silyl group can be used.
  • an alkyl aryl group is suitable.
  • said alkyl group, or said alkenyl group can be straight chain or branched chain, with preferably being of straight ⁇ chain.
  • aryl denotes an aromatic carbon group or a group derived there from.
  • Aryl groups may be monocyclic or polycydic, i.e. they may contain one ring (such as, for example, phenyl) or two or more rings, which may also be fused (such as, for example, naphthyl) or covalently bonded (such as, for example, biphenyl), or contain a combination of fused and bonded rings.
  • 25 Heteroaryl groups contain one or more heteroatoms, preferably selected from O, N, S and Se.
  • aryl groups having 6 2Q to 25 carbon atoms, which optionally contain fused rings and are optionally substituted.
  • Preferred aryl groups are, for example, phenyl, biphenyl, terphenyl,
  • R3 of the chemical formula (I) is a hydrogen atom.
  • organod polysilazane comprises repeating units of formulae (I) and (II),
  • R 4 and R 5 are at each occurrence, dependency or independently of each other, an alkyl group, an alkenyl group, a cydoalkyi group, an aryl group, an alkylsilyl group, an alkylamino group, or an alkoxygroup; in addition one or two of Ri, R2, and Rs can be hydrogen; wherein the formula (II) R 4 and R 5 are at each occurrence, dependency or independently of each other, an alkyl group, an alkenyl group, a cydoalkyi group, an aryl group, an alkylsilyl group, an alkylamino group, an alkoxygroup, or a combination of these; with the proviso that one of R 4 , and Rs can be hydrogen, and 0 ⁇ x+y ⁇ 1 .
  • the matrix material (120) comprises an organo- polysilazane selected from one or more members of the group consisting of organo-polysilazanes represented by following chemical formula (III) and organo-polysilazanes represented by following chemical formula (IV),
  • an alkyl group having 1 to 10 carbon atoms independently of each other, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cycloalkyi group having 3 to 10 carbon atoms, or an aryl group having 3 to 10 carbon atoms;
  • R 12 is an alkenyl group having 2 to 10 carbon atoms;
  • the matrix material (120) can further comprise perhydropolysilazane.
  • perhydropolysilazane to organopolysilazane is in the range from 0:100 to 90:10 by weight. Preferably, it is in the range from 0:100 to 40:60 by weight. More preferably, from 0:100 to 30:70 by weight.
  • organo-polysilazanes and perhydropolysilazane are described, for example, in WO 2015/007778 A1 , JP 2015-1 15369 A and JP 2014-77082 A.
  • the average molecular weight M w of the polysilazanes is not particularly limited according to this embodiment of an optical medium. Preferably, it is in the range from 1 ,000 to 20,000; with being more preferably in the range from 1 ,000 to 10,000.
  • the matrix material (120) can further comprises one or more of transparent polymers.
  • the transparent polymer publically known transparent polymers which are suitable for optical mediums such as optical devices can be used, in particular to adjust the optical transparency of the matrix material (120) in a specified visible light wavelength, and the refractive index of the matrix material (120), and to control the oxygen absorption and/or moisture absorption of the matrix material (120) in a suitable range.
  • transparent means within this embodiment of an optical medium at least around 60 % of incident light transmit at the thickness used in an optical medium and at a wavelength or a range of wavelength used during operation of an optical medium. Preferably, it is over 70 %, more preferably, over 75%, the most preferably, it is over 80 %.
  • the term "polymer” means a material having a repeating unit and having the weight average molecular weight (Mw) 1000 or more.
  • the weight average molecular weight (Mw) of the transparent polymer is in the range from 1 ,000 to 250,000. More preferably it is from 5,000 to 200,000 with more preferably being from 10,000 to 150,000.
  • the transparent polymer is preferably selected from one or more members of the group consisting of poly (meth)acrylates, polystyrene methyl (meth)acrylates, polystyrene, polyvinyl acetate, and polydivinylbenzene from the view point of better optical transparency, lower oxide absorption and high resistivity in high humidity condition.
  • the optical medium further comprises a barrier layer (130) placed over the light luminescent part.
  • polysilazanes in particular perhydropolysilazane (hereafter "PHPS") may be used to prepare the barrier layer (130).
  • PHPS perhydropolysilazane
  • perhydropolzsilazanes may realize wet fabrication process instead of vapor deposition process and can reduce fabrication damage of nanosized fluorescent material in the process, and a barrier layer made from PHPS has less defects in the layer.
  • the barrier layer (130) is a layer obtained from PHPS.
  • the barrier layer (130) may comprise a gradient structure comprised of an outermost part and subsequent part in the layer, wherein the outermost part consists of silicon nitride.
  • the gradient may be a hydrogen content.
  • the outermost part of the gradient structure to the matrix material (120) may comprise a higher amount of hydrogen than the opposite side of the gradient structure to the barrier layer (130).
  • the barrier layer fabricated by using PHPS solution may have lower refractive index than the refractive index of a barrier layer fabricated by any vapor deposition method (such as CVD), and may lead to a better refractive index matching to the matrix materials of the present invention.
  • the barrier layer (130) may have a refractive index in the range from 1 .38 to 1 .85, preferably in the range from 1 .45 to 1 .60. More preferably, the barrier layer (130) is fabricated from PHPS and has the refractive index in the range from 1 .38 to 1 .85, preferably in the range from 1 .45 to 1 .60.
  • VUV vacuum ultraviolet
  • vacuum ultraviolet means an ultraviolet light having a peak wavelength in the region from 190 nm to 80nm.
  • the optical medium (100) can be prepared, and thus be provided for the quantum yield recovery method of the invention, by any method known to a person of ordinary skill in the art. Without being limited thereto, the optical medium (100) may for example be prepared by a method
  • the optical film (100) prepared by the above-described method which can be subjected to the QY recovery method of the invention, can have a thickness that ranges between 0.5 ⁇ to up to 1 mm, without being limited thereto. Typically, it has a thickness that ranges between 10 m to up to several 100 mm.
  • the thickness of the barrier layer (130) can be in the range from 0.1 ⁇ to 1 .0 ⁇ .
  • the optical medium (100) is in the form of a capsule (200) comprising an inner core (210) and a shell encapsulating the inner core (210), in which the inner core (210) comprises the light luminescent part comprising the at least one nanosized fluorescent material (220) and the organic material (230) and the shell comprises a polymer layer (240).
  • the semiconductor nanocrystals (220) are encapsulated within capsules in order to protect the nanocrystals from external influences, as mentioned before.
  • the inner core (210) comprises the at least one nanosized fluorescent material (220) and the organic material (230).
  • the core (210) can further comprises one or more organic solvents to adjust refractive index value of the inner core (210) to the polymer layer (240) comprised in the shell and to increase out coupling efficiency of the light luminescent capsule (200).
  • the inner core (210) essentially consists of a plurality of nanosized light emitting materials (220) and an organic material (230).
  • the nanosized fluorescent material (220) is not specifically limited. A wide variety of publically known nanosized light emitting materials as presented before can be used as desired.
  • the organic material (230) according to this embodiment is preferably selected from Cs to C 4 2 alkanes, Cs to C 4 2 alkenes, Cs to C 4 2 alcohols and combinations of any of these. Still more preferably, the organic material according is selected from Cs to C 4 2 alkanes and Cs to C 4 2 alkenes, and combinations of any of these.
  • Cs to C 4 2 alkanes mean saturated hydrocarbons having only single covalent bonds between their carbons and include straight- chain alkanes having a chain length of 5 to 42 carbon atoms, i.e. linear alkanes wherein the carbon atoms of the backbone are joined in a snakelike structure, as well as branched alkanes, wherein the carbon backbone splits off in one or more directions, overall having 5 to 42 carbon atoms.
  • Cs to C 4 2 alkenes mean unsaturated hydrocarbons that contain at least one carbon-carbon double bond and include straight- chain alkenes having a chain length of 5 to 42 carbon atoms and branched alkenes overall having 5 to 42 carbon atoms.
  • Cs to C 4 2 alcohols include Cs to C 4 2 alkanes wherein at least one hydrogen atom of the carbon backbone is substituted by a hydroxyl group.
  • the Cs to C 4 2 alkanes, Cs to C 4 2 alkenes and Cs to C 4 2 alcohols are of the straight-chain type.
  • the Cs to C 4 2 alkanes and Cs to C 4 2 alkenes may be unsubstituted, mono- or polysubstituted by halogen or CN.
  • said Cs to C 4 2 alkanes and Cs to C 4 2 alkenes are unsubstituted.
  • Non-limiting examples of compounds particularly suitable as organic material (230) according to this embodiment of the optical medium are nonan, decan, undecan, dodecan, tridecan, tetradecan, pentadecan, hexadecan, heptadecan, octadecan, nonadecan, eicosan, heneicosan, docosan, tricosan, tetracosan, pentacosan, hexacosan, heptacosan, octacosan, nonacosan, triacontan, hentriacontan, dotriacontan,
  • the organic material (230) according to this embodiment of the optical medium is selected from one or more of C6 to C30 alkanes and C6 to C30 alkenes. Even more preferably, the organic material (230) is selected from one or more of C16 to C30 alkanes and C16 to C30 alkenes.
  • the organic material (230) is selected from one or more members of the group consisting of octadecane, tetracosane, octacosan, octadecene.
  • the ratio of the nanosized light emitting material (220) and the organic material (230) in the inner core (210) according to this embodiment of the optical medium is in the range from 0.1 :100 to 100:1 .
  • the ratio of the nanosized light emitting material (220) and the organic material (230) in the inner core (210) is in the range from 1 :30 to 100:1 , more preferably in the range from 1 :10 to 99:1 .
  • the optical medium comprises a shell encapsulating the inner core (210) in order to protect the semiconductor nanocrystals (220) from external influences, as mentioned before.
  • the polymer layer (240) comprised in the shell preferably comprises a transparent polymer selected from one or more of the group consisting of poly(meth)acrylates, polystyrene methyl (meth)acrylates, polystyrene, polyvinyl acetate, and polydivinylbenzene.
  • the term "transparent" means at least around 60% of incident light transmit at the thickness used in an optical medium and at a wavelength or a range of wavelength used during operation of an optical medium. Preferably, it is over 70%, more preferably, over 75%, and most preferably, over 80%.
  • the term "polymer” means a material having a repeating unit and having a weight average molecular weight (Mw) of 1000 or more.
  • the weight average molecular weight (Mw) of the transparent polymer is in the range from 1 ,000 to 250,000, more preferably in the range from 5,000 to 200,000 and most preferably in the range from 10,000 to 150,000.
  • the polymer layer (240) is a transparent polymer selected from one or more of the group consisting of poly (meth)acrylates, polystyrene methyl (meth)acrylates, polystyrene, polyvinyl acetate, and polydivinylbenzene. Still more preferably, the polymer layer (240) comprises a transparent polymer selected from one or more members of the group consisting of polydivinylbenzene, poly methyl (meth)acrylates, and polystyrene methyl (meth)acrylates.
  • the polymer layer (240) is a transparent polymer selected from one or more members of the group consisting of
  • polydivinylbenzene poly methyl (meth)acrylates
  • polystyrene methyl (meth)acrylates polystyrene methyl (meth)acrylates
  • the polymer layer (240) may be at least partly covered with a ligand and/or a protection layer (250).
  • the surface ligands include phosphines and phosphine oxides such as Trioctylphosphine oxide (TOPO), Trioctylphosphine (TOP), and
  • Tributylphosphine TBP
  • phosphonic acids such as Dodecylphosphonic acid (DDPA), Tridecylphosphonic acid (TDPA), Octadecylphosphonic acid (ODPA), and Hexylphosphonic acid (HPA)
  • amines such as Dedecyl amine (DDA), Tetradecyl amine (TDA), Hexadecyl amine (HDA), and Octadecyl amine (ODA)
  • thiols such as hexadecane thiol and hexane thiol mercapto carboxylic acids such as mercapto propionic acid and
  • any type of optically transparent material can be used.
  • Preferred examples are polymers selected from polyvinyl alcohols, polyethyl imides, polydivinylbenzene, polymethyl
  • the protection layer (250) itself may additionally be coated with one or more of the above-described surface ligands.
  • the light luminescent capsules (200) can be prepared, and thus be provided for the method of the invention, by any method known to a person of ordinary skill in the art. Without being limited thereto, capsules (200) may be prepared for example by a method comprising at least the following steps (a), (b) and (c):
  • composition comprising at least the nanosized light emitting material (220), the organic material (230), a precursor for the polymer layer (240), a polymerization initiator, a polar solvent, and a polymer solved in said polar solvent, such as polyvinyl alcohol,
  • step (b) stirring the composition obtained in step (a) at a temperature in the range from the melting point of the organic material (230) to 99°C,
  • any type of polar solvent can be used singly or in mixture.
  • the polar solvent can be selected from the group consisting of purified / deionized water; ethylene glycol monoalkyl ethers, such as, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether; diethylene glycol dialkyi ethers, such as, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether; ethylene glycol alkyl ether acetates, such as, methyl cellosolve acetate and ethyl cellosolve acetate; propylene glycol alkyl ether a
  • any polymerization initiator generating an acid, base or radical when being exposed to radiation or heat can be used.
  • Non-limiting examples of the photo radical-generator include azo
  • heat acid-generator examples include p- toluene sulfonates, benzenesulfonates, p-dodecyl benzenesulfonates, 1 ,4- naphthalenedisulfonat.es.
  • heat radical-generators examples include
  • the photo base-generator include multi-substituted amide compounds having amide groups, lactams, imide compounds, and compounds having those structures. Examples of
  • the heat base-generator include: imidazole derivatives, such as, N-(2- nitrobenzyloxycarbonyl)imidazole, N-(3-nitrobenzyloxycarbonyl)imidazole, N-(4-nitrobenzyloxycarbonyl)imidazole, N-(5-methyl-2-nitro- benzyloxycarbonyl)imidazole, and N-(4-chloro-2-nitrobenzyloxycarbonyl)-
  • imidazole derivatives such as, N-(2- nitrobenzyloxycarbonyl)imidazole, N-(3-nitrobenzyloxycarbonyl)imidazole, N-(4-nitrobenzyloxycarbonyl)imidazole, N-(5-methyl-2-nitro- benzyloxycarbonyl)imidazole, and N-(4-chloro-2-nitrobenzyloxycarbonyl)-
  • untrasonification such as ultrasonic probe (from Hielscher UP200Ht) is used in step (b) to control average particle size and ensure smaller particle size and a better size distribution of particles at the same time.
  • Microcapsulation methods that can be used for preparing the above- described light luminescent capsules have been described in, for example, A. Chaiyasat et. al., eXPRESS polymer Letters Vol.6, No.1 , (2012) 70-77.
  • the size of the capsules prepared according to the above-described method typically ranges from 50 nm to 20 ⁇ , without being limited thereto.
  • the total thickness of the shell is usually between 1/4 and 1/10 of the total capsule diameter.
  • the process of the invention enables recovery or even enhancement of the quantum yield of an optical medium, the QY of which has dropped compared to a certain initial QY value, by treating said optical medium simultaneously with heat and moisture.
  • a further aspect of the present invention therefore relates to optical medium obtained or obtainable by the process for quantum yield recovery according to the invention.
  • an optical medium obtained or obtainable by the process for quantum yield recovery according to the invention in an optical device, in particular as an optical film or filter, such as a color filter, color conversion sheet or remote phosphor tape, or a lens.
  • the optical medium in the form of light luminescent capsules (200) can be provided in a composition that comprises said capsules (200) and a matrix material, into which said capsules are incorporated.
  • the light luminescent capsules (200) can be provided in a formulation that comprises at least said capsules and at least one solvent.
  • the present invention also relates to a composition
  • a composition comprising at least an optical medium in the form of a capsule (200) obtained or obtainable by the process for quantum yield recovery according to the present invention and a matrix material.
  • any type of transparent polymers known to the skilled person can be used.
  • Preferred examples are methyl-acrylate, methyl-methacrylate, ethyl- acrylate, ethyl-methacrylate, butyl-acrylate, butyl-methacrylate, 2- ethylhexyl-acrylate, 2-ethylhexyl-methacrylate; substituted alkyl- (meth)acrylates, for examples, hydroxyl-group, epoxy group, or halogen substituted alkyl-(meth)acrylates; cyclopentenyl(meth)acrylate, tetra-hydro furfuryl-(meth)acrylate, benzyl (meth)acrylate, polyethylene-glycol di- (meth)acrylates, polysiloxanes, polysilazanes, polystyrenes, polyvinyl acetate, polydivinylbenzene, or a combination of any of these.
  • the matrix material has a weight average molecular weight in the range from 5,000 to 50,000, more preferably from 10,000 to 30,000.
  • the present invention also relates to a formulation comprising at least an optical medium in the form of a capsule (200) obtained or obtainable by the process for quantum yield recovery according to the present invention and at least one solvent.
  • the type of solvent for use in the formulation is not particularly limited.
  • the solvent is selected from the group consisting of purified water; ethylene glycol monoalkyl ethers, such as, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether; diethylene glycol
  • dialkyl ethers such as, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, propylene glycol methyl ether and diethylene glycol dibutyl ether; ethylene glycol alkyl ether acetates, such as, methyl cellosolve acetate and ethyl cellosolve acetate;
  • propylene glycol alkyl ether acetates such as, propylene glycol
  • PMEA monomethyl ether acetate
  • PMEA propylene glycol monoethyl ether acetate
  • propylene glycol monopropyl ether acetate ketones, such as, methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone
  • alcohols such as, ethanol, propanol, butanol
  • esters such as, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate and ethyl lactate
  • cyclic asters such as, ⁇ -butyrolactone
  • chlorinated hydrocarbons such as chloroform, dichloromethane, chlorobenzene, dichlorobenzene. 25 Those solvents are used singly or in combination of two or more, and the amount thereof depends on the coating method and the thickness of the coating.
  • propylene glycol alkyl ether acetates such as, propylene glycol monomethyl ether acetate (hereafter "PGMEA"), propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, purified water or alcohols can be used.
  • PGMEA propylene glycol monomethyl ether acetate
  • propylene glycol monoethyl ether acetate propylene glycol monopropyl ether acetate
  • purified water or alcohols can be used.
  • the amount of the solvent in the composition can be freely controlled according to the method of coating the composition.
  • the formulation if the formulation is to be spray-coated, it can contain the solvent in an amount of 90 wt.% or more.
  • the content of the solvent is normally 60 wt.% or more, preferably 70 wt.% or more.
  • composition as well as the formulation containing light luminescent capsules (200) can also directly be subjected to the heat and moisture treating for quantum yield recovery according to the process of this invention.
  • the present invention also envisions a process for optical medium quantum yield recovery, wherein the optical medium in the form of capsule (200) is provided in a composition comprising at least said capsules (200) and a matrix material.
  • the present invention envisions a process for optical medium quantum yield recovery, wherein the optical medium in the form of a capsule (200) is provided in a formulation comprising said capsules (200) and a solvent.
  • the present invention relates to an optical device comprising at least an optical medium obtained or obtainable by the process for quantum yield recovery according to the invention, or a composition comprising an optical medium in the form of a capsule obtained or obtainable by the process of the invention and a matrix material, as described above.
  • the optical device comprises at least the optical medium or the composition treated by the process of the invention in a layered or film like structure, such as an optical sheet or film, color conversion sheet or remote phosphor tape.
  • the optical device in accordance with the present invention is preferably selected from a liquid crystal display, an Organic Light Emitting Diode (OLED), a backlight unit for display, a Light Emitting Diode (LED), a Micro Electro Mechanical Systems (MEMS), an electro wetting display, or an electrophoretic display, a lighting device, and/or a solar cell.
  • OLED Organic Light Emitting Diode
  • LED Light Emitting Diode
  • MEMS Micro Electro Mechanical Systems
  • electro wetting display or an electrophoretic display
  • lighting device and/or a solar cell.
  • Fig. 3 shows an exemplary optical device (300) in accordance with the present invention, including a film like structured optical medium (100), at 0 least one nanosized fluorescent material (1 10) (for example, red and/or green), a matrix material (120), a barrier layer (130), and light source (310).
  • the optical device can further include a substrate (320).
  • the optical device (300) comprises an optical film comprising light luminescent capsules (200), which film is prepared using a composition or formulation as described above, then, in Fig. 3, the nanosized fluorescent material (1 10) represents the light luminescent capsules (200).
  • the type of light source (310) in the optical device (300) is not particularly limited.
  • a light emitting diode (LED), a cold cathode fluorescent lamp (CCFL), an electroluminescent device (EL), an organic light emitting device (OLED) or a combination of any of these, can be
  • the optical device (300) can include a substrate (320).
  • a substrate 320
  • transparent substrates are used, which can be flexible, semi-rigid Q or rigid.
  • Publically known transparent substrate suitable for optical devices can be used as desired.
  • transparent substrates are selected from a transparent polymer substrate, glass substrate, thin glass substrate
  • the optical device comprising the layered or film-like structured optical medium (100) according to the first embodiment of the optical medium or the light luminescent capsules (200) according to the second embodiment of the optical medium, for example in an optical film or sheet, is directly
  • semiconductor means a material which has electrical conductivity to a degree between that of a conductor (such as copper) and that of an insulator (such as glass) at room temperature.
  • inorganic means any material not containing carbon atoms or any compound that containing carbon atoms ionically bound to other atoms such as carbon monoxide, carbon dioxide, carbonates, cyanides, cyanates, carbides, and thiocyanates.
  • emission means the emission of electromagnetic waves by electron transitions in atoms and molecules.
  • a 3 cm by 3 cm glass substrate is cleaned by a tissue containing isopropanol, and additionally the substrate is cleaned by spincoating for 30 second at 1000 rpm with isopropanol.
  • organo-polysilazane solution (25 wt.% of the organo-polysilazane in toluene) including 1 wt.% of Luperox ® 531 M80 is mixed with 1 g of quantum sized material solution (3 wt.% of the quantum sized materials in toluene).
  • the organo-polysilazane has the repeating unit represented by the chemical formula of [Si(CH 3 ) 2 -NH] - [SiH(CH 3 )-NH].
  • the obtained solution is spin coated onto the cleaned glass substrate at 1000 rpm for 30 seconds, followed by drying at 130°C for 5 minutes. Then, the coated and dried glass substrate is put into a climate chamber and cured at 85°C / 85 %-rh for 16 hours.
  • the dried and cured sample is cleaned again with isopropanol by spincoating at 2500 rpm for 30 seconds.
  • PHPS perhydropolysilazane
  • VUV vacuum ultraviolet
  • the finally obtained film has a PHPS barrier layer of around 0.3 ⁇ thickness coated on the organo-polysilazane/Q-rod layer. All processes are carried out under nitrogen atmosphere. And except for the VUV light irradiation, all processes are carried out under filtered yellow light condition.
  • Example 2 Preparation of an optical medium (100) - Organo- polysilazane+Q-rod/PHPS optical film
  • Example 2 The optical film of Example 2 is prepared in the same manner as described in Example 1 , except that the coated glass substrate is dried at
  • the finally obtained film has a PHPS barrier layer of around 0.3 ⁇ thickness coated on the organo-polysilazane/Q-rod layer.
  • Example 3 Preparation of an optical medium (100) - Organo- polysilazane+Q-rod/PHPS optical film
  • Example 3 The optical film of Example 3 is prepared in the same manner as described in Example 1 , except that 0.2 g of PHPS solution (20 wt.-% of PHPS in dibutylether) is added into the solution containing 1 g of organo- polysilazane (25 wt.-% of the organo-polysilazane in toluene) and 1 wt.-% of Luperox ® 531 M80.
  • the finally obtained film has a PHPS barrier layer of around 0.3 ⁇ thickness coated on the organo-polysilazane/Q-rod layer.
  • Example 4 Preparation of an optical medium (100) - Organo- polysilazane+Q-rod/PHPS optical film
  • the optical film of Example 4 is prepared in the same manner as described in Example 3, except that the coated glass substrate is dried at 130°C for 5 minutes and then cured at 85°C / 85 %-rh for 1 hour.
  • the finally obtained film has a PHPS barrier layer of around 0.3 ⁇ thickness coated on the organo-polysilazane/Q-rod layer.
  • Example 5 Preparation of an optical medium (100) - Organo- polysilazane+Q-rod/PHPS optical film
  • the optical film of Example 5 is prepared in the same manner as described in Example 2, except that the solution containing 1 g of organo- polysilazane (25 wt.-% of the organo-polysilazane in toluene) does not include any Luperox® 531 M80.
  • the finally obtained film has a PHPS barrier layer of around 0.3 ⁇ thickness coated on the organo-polysilazane/Q-rod layer.
  • Example 6 Preparation of an optical medium (100) - Organo- polysilazane+Q-rod/PHPS optical film
  • the optical film of Example 6 is prepared in the same manner as described in Example 1 , except that the solution containing 1 g of organo- polysilazane (25 wt.-% of the organo-polysilazane in toluene) does not include any Luperox® 531 M80. Moreover, after the PHPS drying process the PHPS layer is not exposed to VUV light, but placed under 85°C / 85%-rh in a clinnate chamber for 16 hours to perform curing.
  • the finally obtained film has a PHPS barrier layer of around 0.3 ⁇ thickness coated on the organo-polysilazane/Q-rod layer.
  • Example 7 Preparation of an optical medium (100) - Organo- polysilazane+Q-rod optical film
  • An optical film is prepared in the same manner as described in Example 1 except of coating the PHPS barrier layer onto the cured organo- polysilazane layer.
  • the absolute quantum yield (QY) of each optical film obtained from Examples 1 to 7 is measured directly after curing by VUV light.
  • Quantum Yield (QY) values are measured directly by using an absolute photoluminescence QY spectrometer (Hamamatsu model: Quantaurus C1 1347)
  • each optical film obtained from Examples 1 to 7 is placed in a climate chamber set to 85°C and 85%-rh in air.
  • Fig. 4 shows the normalized quantum yield of the optical films obtained from Examples 1 to 6, each of which comprises a PHPS barrier layer, as function of time.
  • the QY of the quantum rods has dropped significantly to below 60%, even below 40% (quantum rods in solution usually have a QY of 70% to 75%).
  • Treating the quantum rods-containing optical films at 85°C / 85%-rh for 1 day recovers the QY back to values of 60% to more than 80%.
  • Fig. 5 shows the normalized quantum yield of the optical film obtained from Example 7, which does not comprise a PHPS barrier layer, as function of time.
  • the QY of the quantum rods has dropped significantly to 58% (quantum rods in solution usually have a QY of around 70% to 75%).
  • Treating the quantum rods-containing optical film at 85°C / 85%-rh for 1 day recovers the QY to 70%. After 5 days of heat and moisture treating, the QY even increases to 73%.
  • Each optical film obtained from Examples 1 to 7 is placed in an oven at ambient conditions (about 23°C/50%-rh).
  • Example 9 Preparation of an optical medium (200) in form of a capsule 0.27g of polyvinyl alcohol (Mowiol ® 8 - 88, Mw: 67,000; from Sigma Aldrich, hereafter "PVA”) is dissolved in 30.0 ml of deionized water. Then, 1 .5 g of divinyl benzene (hereafter “DVB”) is mixed with 225 mg of quantum sized materials (from Merck, hereafter “QM”) in octadecane solution (15 wt.-% of quantum sized material in octadecane) and 0.16 g of benzoylperoxide (hereafter "BPO").
  • PVA polyvinyl alcohol
  • DVB divinyl benzene
  • QM quantum sized materials
  • BPO benzoylperoxide
  • the obtained DVB/octadecane//BPO/QM solution is mixed with the PVA/water solution and emulsified with T18 digital ULTRA-TURRAX ® at 5000 rpm for 5 min. All steps above are conducted at 40°C to prevent octadecane from solidifying. Afterwards, the obtained emulsion is transferred to a glass flask and polymerized at 70°C for 24 hours under argon atmosphere.
  • the capsules-containing optical film obtained from Example 10 is stored at 85°C for 7 days.
  • the absolute quantum yield (QY) of the optical film is measured directly after this temperature treating.
  • the absolute QY value is measured directly by using an absolute photoluminescence QY spectrometer (Hamamatsu model: Quantaurus C1 1347). Then, the optical film obtained from Example 10 is placed in a climate chamber set to 85°C and 85%-rh in air.
  • Fig. 6 shows the normalized quantum yield of the capsules-containing optical film obtained from Example 10 as function of time.
  • the QY of the light luminescent capsules comprised in the optical film drops from 68% to 1 1 % after storing at 85°C because of temperature quenching.
  • the QY recovers back to up to 55% after 1 day (day 8) and even to 64% after 5 days (day 14).

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Abstract

La présente invention concerne un procédé de récupération de rendement quantique d'un support optique.
PCT/EP2018/070644 2017-08-03 2018-07-31 Récupération de rendement quantique Ceased WO2019025392A1 (fr)

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