WO2020050144A1 - Matériau de conversion de couleur, élément de conversion de couleur, unité de source de lumière, dispositif d'affichage, dispositif d'éclairage, substrat de conversion de couleur et encre - Google Patents

Matériau de conversion de couleur, élément de conversion de couleur, unité de source de lumière, dispositif d'affichage, dispositif d'éclairage, substrat de conversion de couleur et encre Download PDF

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WO2020050144A1
WO2020050144A1 PCT/JP2019/034006 JP2019034006W WO2020050144A1 WO 2020050144 A1 WO2020050144 A1 WO 2020050144A1 JP 2019034006 W JP2019034006 W JP 2019034006W WO 2020050144 A1 WO2020050144 A1 WO 2020050144A1
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color conversion
particulate
light
conversion material
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PCT/JP2019/034006
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Japanese (ja)
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裕健 境野
泰宜 市橋
祐一 辻
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東レ株式会社
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Priority to CN201980055522.2A priority Critical patent/CN112639542B/zh
Priority to JP2019549015A priority patent/JP7380216B2/ja
Priority to KR1020217004840A priority patent/KR20210055677A/ko
Publication of WO2020050144A1 publication Critical patent/WO2020050144A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/55—Boron-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • 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
    • C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
    • 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
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F21—LIGHTING
    • F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
    • F21V9/00—Elements for modifying spectral properties, polarisation or intensity of the light emitted, e.g. filters
    • F21V9/30—Elements containing photoluminescent material distinct from or spaced from the light source
    • F21V9/38—Combination of two or more photoluminescent elements of different materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/206—Filters comprising particles embedded in a solid matrix
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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

Definitions

  • the present invention relates to a color conversion material, a color conversion member, a light source unit, a display, a lighting device, a color conversion substrate, and ink.
  • the application of the multi-color conversion technology based on the color conversion method to liquid crystal displays, organic EL displays, lighting devices, and the like has been actively studied.
  • the color conversion is to convert light emitted from a light emitter to light having a longer wavelength, for example, to convert blue light to green or red light.
  • the composition having the color conversion function (hereinafter, referred to as “color conversion composition”) is formed into a sheet and combined with, for example, a blue light source to extract three primary colors of blue, green, and red from the blue light source, ie, white light. Can be taken out.
  • a white light source combining such a blue light source and a sheet having a color conversion function (hereinafter, referred to as a “color conversion sheet”) is used as a backlight unit, and this backlight unit, a liquid crystal driving portion, and a color filter are combined.
  • a full-color display can be manufactured.
  • if there is no liquid crystal driving portion it can be used as it is as a white light source, and can be applied as a white light source such as LED lighting.
  • One of the problems with liquid crystal displays that use the color conversion method is to improve color reproducibility.
  • To improve the color reproducibility it is effective to narrow the half width of each of the blue, green, and red emission spectra of the backlight unit and increase the color purity of each of the blue, green, and red colors.
  • a technique using quantum dots made of inorganic semiconductor fine particles as a component of a color conversion composition has been proposed (for example, see Patent Document 1).
  • a technique has been proposed in which an organic light emitting material is used as a component of a color conversion composition instead of a quantum dot.
  • examples of techniques using an organic light emitting material as a component of a color conversion composition include those using a coumarin derivative (for example, see Patent Document 2), those using a rhodamine derivative (for example, see Patent Document 3), and pyromethene derivatives. (For example, see Patent Document 4).
  • a technique of adding a light stabilizer to prevent deterioration of an organic light emitting material and improve durability has been disclosed (for example, see Patent Document 5).
  • JP 2012-22028 A JP 2007-273440 A JP 2001-164245 A JP 2011-241160 A International Publication No. 2011/149028
  • the technology using quantum dots described in Document 1 certainly has narrow half-widths of green and red emission spectra, and improves color reproducibility.
  • the quantum dots were weak to heat, moisture and oxygen in the air, and had insufficient durability.
  • problems such as containing cadmium.
  • high definition such as 4K and 8K, high dynamic range (HDR), and high contrast by local dimming
  • the illuminance required for a backlight unit of a liquid crystal display is increasing, and the backlight unit by driving heat is used. Has become hot.
  • existing techniques such as the light stabilizer described in Patent Document 5 have an effect of improving durability, but are insufficient as techniques for improving durability at high temperatures.
  • a color conversion material using an organic light emitting material has a problem that durability is significantly deteriorated at a high temperature, and the existing technology has not been able to sufficiently solve this problem.
  • the problem to be solved by the present invention is to achieve both improved color reproducibility and durability in a color conversion material used for a liquid crystal display or LED lighting. It is to make them compatible.
  • an object of the present invention is to provide a color conversion material and a color conversion member having improved durability at high temperatures.
  • the present invention is a particulate color conversion material having a matrix resin and at least one luminescent material, wherein the luminescent material is represented by a general formula (1).
  • a particulate color conversion material containing X is CR 7 or N.
  • R 1 to R 9 may be the same or different and each may be hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, or an aryl group.
  • the color conversion material and the color conversion member using the same according to the present invention have both high color purity and durability, so that both color reproducibility and durability can be achieved.
  • FIG. 2 is a schematic sectional view illustrating an example of the color conversion member of the present invention.
  • FIG. 2 is a schematic sectional view illustrating an example of the color conversion member of the present invention.
  • FIG. 2 is a schematic sectional view illustrating an example of the color conversion member of the present invention.
  • 9 is an emission spectrum in Example 2 of the present invention.
  • the particulate color conversion material according to the embodiment of the present invention contains at least one kind of luminescent material.
  • the light-emitting material in the present invention refers to a material that emits light having a different wavelength from the light when the light is irradiated.
  • the organic light emitting material is an organic light emitting material.
  • the light-emitting material is a material exhibiting high emission quantum yield and high emission characteristics.
  • known light-emitting materials such as inorganic phosphors, fluorescent pigments, fluorescent dyes, and quantum dots are used as the light-emitting materials.
  • an organic luminescent material is preferable from the viewpoint of uniformity of dispersion, reduction of the amount of use, and reduction of environmental load.
  • organic light emitting material examples include the following.
  • a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluoranthene, fluorene, or indene, or a derivative thereof may be mentioned as a suitable organic light emitting material.
  • Suitable organic light-emitting materials include compounds having a heteroaryl ring such as pyrrolopyridine, derivatives thereof, and borane derivatives.
  • Suitable organic light-emitting materials include stilbene derivatives such as amino) stilbene, aromatic acetylene derivatives, tetraphenylbutadiene derivatives, aldazine derivatives, pyromethene derivatives, and diketopyrrolo [3,4-c] pyrrole derivatives.
  • coumarin derivatives such as coumarin 6, coumarin 7, coumarin 153
  • azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole and metal complexes thereof
  • cyanine compounds such as indocyanine green, fluorescein, Xanthene-based compounds such as eosin and rhodamine, thioxanthene-based compounds, and the like are mentioned as suitable organic light-emitting materials.
  • Suitable organic light emitting materials include aromatic amine derivatives such as -di (3-methylphenyl) -4,4'-diphenyl-1,1'-diamine.
  • organic metal complex compounds such as iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os), and rhenium (Re) are suitable for organic light emission.
  • Ir iridium
  • Ru ruthenium
  • Rh rhodium
  • Pd palladium
  • Pt platinum
  • Os osmium
  • Re rhenium
  • Re rhenium
  • the organic light emitting material in the present invention is not limited to those described above.
  • a compound having a coordination bond is preferable from the viewpoint of solubility and diversity of molecular structure.
  • a boron-containing compound such as a boron fluoride complex is also preferable in that the half width is small and light emission with high efficiency is possible.
  • a pyrromethene derivative can be suitably used because it gives a high fluorescence quantum yield and has good durability. More preferably, it is a compound represented by the general formula (1).
  • the particulate color conversion material according to the embodiment of the present invention preferably contains at least a compound represented by the general formula (1) as a light emitting material.
  • R 1 to R 9 may be the same or different and each may be hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, or an aryl group.
  • Ether arylthioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, ester, carbamoyl, amino, nitro, silyl, siloxanyl, boryl, sulfo Group, a phosphine oxide group, and a condensed ring and an aliphatic ring formed between adjacent groups.
  • hydrogen may be deuterium.
  • a substituted or unsubstituted aryl group having 6 to 40 carbon atoms has 6 to 40 carbon atoms including the number of carbon atoms contained in the substituent substituted with the aryl group.
  • An aryl group The same applies to other substituents defining the number of carbon atoms.
  • Aryl ether, aryl thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, ester, carbamoyl, amino, nitro, silyl, siloxanyl, boryl , A sulfo group, and a phosphine oxide group are preferable, and specific substituents which are preferable in the description of each substituent are preferable. Further, these substituents may be further substituted by the above-mentioned substituents.
  • the alkyl group means, for example, a saturated aliphatic hydrocarbon such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group and a tert-butyl group.
  • a saturated aliphatic hydrocarbon such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group and a tert-butyl group.
  • the number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 20 and more preferably 1 to 8 from the viewpoint of availability and cost.
  • the cycloalkyl group refers to, for example, a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, which may or may not have a substituent.
  • the number of carbon atoms in the alkyl group portion is not particularly limited, but is preferably in the range of 3 or more and 20 or less.
  • the heterocyclic group refers to, for example, an aliphatic ring having atoms other than carbon in the ring, such as a pyran ring, a piperidine ring, and a cyclic amide, which may or may not have a substituent. Good.
  • the carbon number of the heterocyclic group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.
  • alkenyl group refers to, for example, an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group, or a butadienyl group, which may or may not have a substituent. .
  • the carbon number of the alkenyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.
  • the cycloalkenyl group refers to, for example, an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, and a cyclohexenyl group, which may have a substituent. It is not necessary to have.
  • Alkynyl group means, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, which may or may not have a substituent.
  • the number of carbon atoms of the alkynyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.
  • the alkoxy group refers to, for example, a functional group in which an aliphatic hydrocarbon group is bonded via an ether bond such as a methoxy group, an ethoxy group, and a propoxy group.
  • the aliphatic hydrocarbon group has a substituent. May not be included.
  • the carbon number of the alkoxy group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.
  • An alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
  • the hydrocarbon group of the alkylthio group may or may not have a substituent.
  • the carbon number of the alkylthio group is not particularly limited, but is preferably in the range of 1 to 20.
  • An aryl ether group refers to, for example, a functional group in which an aromatic hydrocarbon group is bonded via an ether bond, such as a phenoxy group, and the aromatic hydrocarbon group may or may not have a substituent. Is also good.
  • the carbon number of the aryl ether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.
  • the arylthioether group is a group in which an oxygen atom of an ether bond of the arylether group is substituted with a sulfur atom.
  • the aromatic hydrocarbon group in the arylthioether group may or may not have a substituent.
  • the number of carbon atoms of the arylthioether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.
  • a phenyl group a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, an anthracenyl group, a pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are preferred.
  • the aryl group may or may not have a substituent.
  • the carbon number of the aryl group is not particularly limited, but is preferably in the range of 6 or more and 40 or less, and more preferably in the range of 6 or more and 30 or less.
  • the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group or an anthracenyl group, and a phenyl group, a biphenyl group Groups, terphenyl groups and naphthyl groups are more preferred. More preferred are phenyl, biphenyl and terphenyl, with phenyl being particularly preferred.
  • the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, or an anthracenyl group, and a phenyl group, a biphenyl group, A phenyl group and a naphthyl group are more preferred. Particularly preferred is a phenyl group.
  • Heteroaryl group for example, pyridyl group, furanyl group, thienyl group, quinolinyl group, isoquinolinyl group, pyrazinyl group, pyrimidyl group, pyridazinyl group, triazinyl group, naphthyridinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, Benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, carbolinyl, indolocarbazolyl, benzofurcarbazolyl, benzothienocarbazolyl Group, dihydroindenocarbazolyl group, benzoquinolinyl group, acridinyl group, dibenzoacridinyl group, benzimidazolyl group, imid
  • Atoms other than carbon shows a cyclic aromatic group having a single or a plurality of rings.
  • naphthyridinyl means any of 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 1,8-naphthyridinyl, 2,6-naphthyridinyl, and 2,7-naphthyridinyl.
  • the heteroaryl group may or may not have a substituent. Although the carbon number of the heteroaryl group is not particularly limited, it is preferably in the range of 2 or more and 40 or less, more preferably 2 or more and 30 or less.
  • R 1 to R 9 are a substituted or unsubstituted heteroaryl group
  • examples of the heteroaryl group include pyridyl, furanyl, thienyl, quinolinyl, pyrimidyl, triazinyl, benzofuranyl, benzothienyl, and indolyl.
  • Group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, benzimidazolyl group, imidazopyridyl group, benzoxazolyl group, benzothiazolyl group, phenanthrolinyl group is preferred, and pyridyl group, furanyl group, thienyl group, quinolinyl group is preferred. More preferred. Particularly preferred is a pyridyl group.
  • heteroaryl group examples include pyridyl, furanyl, thienyl, quinolinyl, pyrimidyl, triazinyl, benzofuranyl, benzothienyl, indolyl, and dibenzoyl.
  • a furanyl group, a dibenzothienyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, and a phenanthrolinyl group are preferred, and a pyridyl group, a furanyl group, a thienyl group, and a quinolinyl group are more preferred. Particularly preferred is a pyridyl group.
  • Halogen indicates an atom selected from fluorine, chlorine, bromine and iodine.
  • the ester group is, for example, a functional group in which an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group and the like are bonded via an ester bond, and the substituent may be further substituted.
  • the carbon number of the ester group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.
  • a methyl ester group such as a methoxycarbonyl group, an ethyl ester group such as an ethoxycarbonyl group, a propyl ester group such as a propoxycarbonyl group, a butyl ester group such as a butoxycarbonyl group, and an isopropyl group such as an isopropoxymethoxycarbonyl group.
  • Examples include an ester group, a hexyl ester group such as a hexyloxycarbonyl group, and a phenyl ester group such as a phenoxycarbonyl group.
  • the carbonyl group, carboxyl group, ester group, and carbamoyl group may or may not have a substituent.
  • Amino group is a substituted or unsubstituted amino group.
  • substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, and a branched alkyl group.
  • aryl group and the heteroaryl group a phenyl group, a naphthyl group, a pyridyl group, and a quinolinyl group are preferable. These substituents may be further substituted.
  • the carbon number is not particularly limited, but is preferably in the range of 2 to 50, more preferably 6 to 40, and particularly preferably 6 to 30.
  • the silyl group includes, for example, an alkylsilyl group such as a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a propyldimethylsilyl group, a vinyldimethylsilyl group, a phenyldimethylsilyl group, a tert-butyldiphenylsilyl group, And an arylsilyl group such as a phenylsilyl group and a trinaphthylsilyl group. Substituents on silicon may be further substituted.
  • the carbon number of the silyl group is not particularly limited, but is preferably in the range of 1 to 30.
  • the siloxanyl group indicates, for example, a silicon compound group via an ether bond such as a trimethylsiloxanyl group. Substituents on silicon may be further substituted.
  • the boryl group is a substituted or unsubstituted boryl group. Examples of the substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, an aryl ether group, an alkoxy group, and a hydroxyl group. Among them, an aryl group and an aryl ether group are preferable.
  • the sulfo group is a substituted or unsubstituted sulfo group.
  • substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, an aryl ether group, and an alkoxy group.
  • a linear alkyl group and an aryl group are preferable.
  • R 10 R 11 is selected from the same group as R 1 to R 9 .
  • a condensed ring and an aliphatic ring formed between adjacent substituents are conjugated or non-conjugated when any two adjacent substituents (for example, R 1 and R 2 in the general formula (1)) are bonded to each other.
  • Such a constitutive element of the condensed ring and the aliphatic ring may include an element selected from nitrogen, oxygen, sulfur, phosphorus, and silicon, in addition to carbon. Further, these condensed ring and aliphatic ring may be further condensed with another ring.
  • the compound represented by the general formula (1) exhibits a high emission quantum yield and has a small half width of the emission spectrum, so that both efficient color conversion and high color purity can be achieved. Furthermore, the compound represented by the general formula (1) has various characteristics such as luminous efficiency, color purity, thermal stability, light stability and dispersibility by introducing an appropriate substituent at an appropriate position. And physical properties can be adjusted. For example, compared to the case where all of R 1 , R 3 , R 4 and R 6 are hydrogen, at least one of R 1 , R 3 , R 4 and R 6 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkyl group. An aryl group or a substituted or unsubstituted heteroaryl group shows better thermal stability and light stability.
  • the alkyl group includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,
  • An alkyl group having 1 to 6 carbon atoms such as a sec-butyl group, a tert-butyl group, a pentyl group and a hexyl group is preferred.
  • a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group are preferable from the viewpoint of excellent thermal stability.
  • a sterically bulky tert-butyl group is more preferred as the alkyl group.
  • a methyl group is also preferably used as the alkyl group.
  • the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, more preferably, A phenyl group and a biphenyl group. Particularly preferred is a phenyl group.
  • the heteroaryl group is preferably a pyridyl group, a quinolinyl group or a thienyl group, more preferably a pyridyl group.
  • Quinolinyl group Particularly preferred is a pyridyl group.
  • R 1 , R 3 , R 4 and R 6 are all the same or different and are each a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, better thermal stability and It is preferable because it shows light stability.
  • all of R 1 , R 3 , R 4 and R 6 may be the same or different, and are more preferably a substituted or unsubstituted aryl group.
  • R 1 , R 3 , R 4 and R 6 may be the same or different, and in the case of a substituted or unsubstituted aryl group, for example, R 1 ⁇ R 4 , R 3 ⁇ R 6 , R It is preferable to introduce a plurality of types of substituents such as 1 ⁇ R 3 or R 4 ⁇ R 6 .
  • “ ⁇ ” indicates a group having a different structure.
  • R 1 ⁇ R 4 indicates that R 1 and R 4 are groups having different structures.
  • an aryl group substituted with an electron donating group is preferable.
  • the electron donating group is an atomic group that provides an electron to a substituted atomic group due to an induction effect or a resonance effect in organic electron theory.
  • Examples of the electron donating group include those having a negative value as a substituent constant ( ⁇ p (para)) according to the Hammett rule.
  • the substituent constant ( ⁇ p (para)) of the Hammett's rule can be quoted from Chemical Handbook Basic Edition, Revised 5th Edition (page II-380).
  • electron donating groups for example, an alkyl group (.sigma.p methyl group: -0.17) and alkoxy groups (.sigma.p methoxy groups: -0.27), .sigma.p amino group (-NH 2: - 0.66).
  • an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms is preferable, and a methyl group, an ethyl group, a tert-butyl group, and a methoxy group are more preferable. From the viewpoint of dispersibility, a tert-butyl group and a methoxy group are particularly preferred.
  • the substitution position of the substituent is not particularly limited, it is necessary to suppress the twist of the bond in order to enhance the photostability of the compound represented by the general formula (1). It is preferred to attach to the position or para.
  • an aryl group that mainly affects luminous efficiency an aryl group having a bulky substituent such as a tert-butyl group, an adamantyl group, and a methoxy group is preferable.
  • X it is preferable from the viewpoint of light stability is C-R 7.
  • the substituent R 7 has a great effect on the durability of the compound represented by the general formula (1), that is, the decrease over time in the emission intensity of the compound.
  • R 7 is hydrogen
  • the reactivity of this site is high, and this site easily reacts with moisture or oxygen in the air. This causes decomposition of the compound represented by the general formula (1).
  • R 7 is a substituent having a large degree of freedom of movement of a molecular chain such as an alkyl group, the reactivity certainly decreases, but the compounds aggregate over time in the color conversion material, As a result, the emission intensity is reduced due to concentration quenching.
  • R 7 is preferably a group that is rigid, has a small degree of freedom of movement, and hardly causes aggregation.
  • R 7 is preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Preferably, it is either one.
  • R 7 is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group, and is preferably a substituted or unsubstituted naphthyl group.
  • R 7 is preferably a suitably bulky substituent.
  • R 7 is, it is possible to prevent aggregation of the molecules to have some bulkiness, as a result, emission efficiency and durability of the compound represented by the general formula (1) is further improved.
  • a more preferable example of such a bulky substituent includes a structure of R 7 represented by the following general formula (2).
  • r is hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an arylether group, or an arylthioether.
  • aryl group aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, boryl group, sulfo group, phosphine oxide group Selected from the group consisting of k is an integer of 1 to 3. When k is 2 or more, r may be the same or different.
  • r is preferably a substituted or unsubstituted aryl group.
  • aryl groups particularly preferred are a phenyl group and a naphthyl group.
  • k in the general formula (2) is preferably 1 or 2, and more preferably 2 from the viewpoint of further preventing aggregation of molecules. Further, when k is 2 or more, it is preferable that at least one of r is substituted with an alkyl group.
  • the alkyl group in this case, a methyl group, an ethyl group, and a tert-butyl group are particularly preferable examples from the viewpoint of thermal stability.
  • r is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group or a halogen.
  • a methyl group, an ethyl group, a tert-butyl group and a methoxy group are more preferred.
  • a tert-butyl group and a methoxy group are particularly preferred.
  • R 1 to R 7 is an electron withdrawing group.
  • R 1 to R 6 is an electron withdrawing group
  • R 7 is an electron withdrawing group
  • An electron-withdrawing group is also called an electron-accepting group, and is an atomic group that attracts electrons from a substituted atomic group due to an induction effect or a resonance effect in organic electron theory.
  • Examples of the electron withdrawing group include those having a positive value as a substituent constant ( ⁇ p (para)) according to the Hammett rule.
  • the substituent constant ( ⁇ p (para)) of the Hammett's rule can be quoted from Chemical Handbook Basic Edition, Revised 5th Edition (page II-380).
  • the phenyl group may have a positive value as described above, the electron-withdrawing group does not include the phenyl group in the present invention.
  • electron withdrawing groups include, for example, -F ( ⁇ p: +0.06), -Cl ( ⁇ p: +0.23), -Br ( ⁇ p: +0.23), -I ( ⁇ p: +0.18), —CO 2 R 12 ( ⁇ p: +0.45 when R 12 is an ethyl group), —CONH 2 ( ⁇ p: +0.38), —COR 12 ( ⁇ p: +0.49 when R 12 is a methyl group), ⁇ CF 3 ( ⁇ p: +0.50), - SO 2 R 12 ( ⁇ p: when R 12 is a methyl group +0.69), - NO 2 ( ⁇ p : +0.81) , and the like.
  • R 12 is each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atom atoms, a substituted or unsubstituted heterocyclic group.
  • Preferred electron withdrawing groups include fluorine, a fluorinated aryl group, a fluorinated heteroaryl group, a fluorinated alkyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, Examples thereof include a substituted or unsubstituted sulfonyl group or a cyano group. This is because they are hardly chemically decomposed.
  • More preferred electron withdrawing groups include fluorinated alkyl groups, substituted or unsubstituted carbonyl groups, substituted or unsubstituted ester groups, and cyano groups. This is because these lead to the effect of preventing concentration quenching and improving the emission quantum yield. Particularly preferred electron withdrawing groups are substituted or unsubstituted ester groups.
  • R 2 and R 5 are preferably hydrogen, an alkyl group, or an aryl group from the viewpoint of thermal stability, and more preferably hydrogen from the viewpoint that a narrow half-value width is easily obtained in an emission spectrum.
  • At least one of R 2 and R 5 may be the same or different, and is preferably an electron-withdrawing group.
  • at least one of R 2 and R 5 may be the same or different, and a substituted or unsubstituted ester group can improve durability without reducing color purity.
  • both R 2 and R 5 may be the same or different, and it is particularly preferable that they are substituted or unsubstituted ester groups from the viewpoint of improving durability.
  • R 8 and R 9 are preferably an alkyl group, an aryl group, a heteroaryl group, fluorine, a fluorine-containing alkyl group, a fluorine-containing heteroaryl group or a fluorine-containing aryl group, and a cyano group.
  • R 8 and R 9 are more preferably fluorine, a fluorine-containing aryl group, or a cyano group because they are stable to excitation light and can obtain a higher fluorescence quantum yield.
  • the fluorine-containing aryl group is an aryl group containing fluorine, and examples thereof include a fluorophenyl group, a trifluoromethylphenyl group, and a pentafluorophenyl group.
  • the fluorine-containing heteroaryl group is a fluorine-containing heteroaryl group, and examples thereof include a fluoropyridyl group, a trifluoromethylpyridyl group, and a trifluoropyridyl group.
  • the fluorine-containing alkyl group is an alkyl group containing fluorine, and examples thereof include a trifluoromethyl group and a pentafluoroethyl group.
  • the stability of the compound represented by the general formula (1) to oxygen is further improved, and as a result, the durability of the compound can be further improved.
  • it is a cyano group.
  • it is preferable that at least one of R 8 and R 9 is a cyano group, because the electron density on the boron atom is further reduced.
  • R 8 and R 9 are also preferably fluorine from the viewpoint of obtaining a high fluorescence quantum yield and the ease of synthesis.
  • R 1 , R 3 , R 4 and R 6 may be the same or different, and the above-mentioned Ar-1 To Ar-6, wherein X is CR 7 and R 7 is a group represented by the general formula (2).
  • R 7 is more preferably a group represented by the general formula (2) in which r is contained as a tert-butyl group or a methoxy group, and represented by a general formula (2) in which r is contained as a methoxy group. It is particularly preferred that the group is
  • R 1 , R 3 , R 4 and R 6 may be the same or different, and may be substituted or unsubstituted.
  • An alkyl group, and R 2 and R 5 may be the same or different, each being a substituted or unsubstituted ester group, X is C—R 7 , and R 7 is a general formula
  • R 7 is particularly preferably a group represented by the general formula (2) in which r is contained as a substituted or unsubstituted phenyl group.
  • R 1 , R 3 , R 4 and R 6 may be the same or different, and the above-mentioned Ar-1 To R-6, and R 2 and R 5 may be the same or different, each being a substituted or unsubstituted ester group, X is CR 7 , and R 7 is Examples thereof include a group represented by the general formula (2).
  • R 7 is more preferably a group represented by the general formula (2) in which r is contained as a tert-butyl group or a methoxy group, and represented by a general formula (2) in which r is contained as a methoxy group. It is particularly preferred that the group is
  • the compound represented by the general formula (1) can be synthesized, for example, by the method described in Japanese Patent Application Laid-Open No. Hei 8-509471 or JP-A-2000-208262. That is, by reacting a pyromethene compound with a metal salt in the presence of a base, the intended pyrromethene-based metal complex can be obtained.
  • a method of generating a carbon-carbon bond by using a coupling reaction between a halogenated derivative and a boronic acid or a boronic esterified derivative may be mentioned.
  • the present invention is not limited to this.
  • an amino group or a carbazolyl group for example, a method of generating a carbon-nitrogen bond by using a coupling reaction between a halogenated derivative and an amine or a carbazole derivative under a metal catalyst such as palladium.
  • the present invention is not limited to this.
  • organic light-emitting materials other than the compound represented by the general formula (1) are shown below, but the present invention is not particularly limited thereto.
  • the particulate color conversion material according to the embodiment of the present invention includes a light-emitting material exhibiting light emission observed in a region having a peak wavelength of 500 nm or more and less than 580 nm (hereinafter, referred to as “first light-emitting material”).
  • first light-emitting material a light-emitting material exhibiting light emission observed in a region having a peak wavelength of 500 nm or more and less than 580 nm
  • green light emission light emission observed in a region having a peak wavelength of 500 nm or more and less than 580 nm
  • the particulate color conversion material according to the embodiment of the present invention may include a light-emitting material which emits light whose peak wavelength is observed in a range of 580 nm to 750 nm (hereinafter, referred to as “second light-emitting material”).
  • second light-emitting material a light-emitting material which emits light whose peak wavelength is observed in a range of 580 nm to 750 nm
  • the emission observed in the region where the peak wavelength is 580 nm or more and 750 nm or less is referred to as “red emission”.
  • excitation light having a wavelength of 400 nm or more and 500 nm or less is preferable because the excitation energy is relatively small.
  • either the first light emitting material and / or the second light emitting material may be included, or both may be included. Further, only one kind of the first light emitting material may be used alone, or a plurality of kinds of the first light emitting materials may be used in combination. Similarly, only one kind of the second light emitting material may be used alone, or a plurality of kinds of second light emitting materials may be used in combination.
  • the particulate color conversion material according to the embodiment of the present invention includes a first light emitting material emitting green light and a second light emitting material emitting red light, and uses a blue LED having a sharp emission peak as blue light.
  • a sharp emission spectrum is shown in each of the blue, green, and red colors, and white light with good color purity can be obtained.
  • colors can be more vivid and a larger color gamut can be efficiently created.
  • the emission characteristics particularly in the green and red regions, are improved. A light source can be obtained.
  • Examples of the first light emitting material include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153, cyanine derivatives such as indocyanine green, fluorescein derivatives such as fluorescein, fluorescein isothiocyanate, carboxyfluorescein diacetate, and phthalocyanine derivatives such as phthalocyanine green.
  • coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153
  • cyanine derivatives such as indocyanine green
  • fluorescein derivatives such as fluorescein, fluorescein isothiocyanate, carboxyfluorescein diacetate
  • phthalocyanine derivatives such as phthalocyanine green.
  • Perylene derivatives such as diisobutyl-4,10-dicyanoperylene-3,9-dicarboxylate, as well as pyromethene derivatives, stilbene derivatives, oxazine derivatives, naphthalimide derivatives, pyrazine derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives , Imidazopyridine derivatives, azole derivatives, compounds having fused aryl rings such as anthracene and derivatives thereof, aromatic amine derivatives, organic Metal complex compounds, and the like as preferred.
  • the first light emitting material is not particularly limited to these.
  • the pyrromethene derivative is a particularly suitable compound because it gives a high emission quantum yield and has good durability.
  • a compound represented by the general formula (1) is preferable because it emits light with high color purity.
  • Examples of the second light emitting material include cyanine derivatives such as 4-dicyanomethylene-2-methyl-6- (p-dimethylaminostyryl) -4H-pyran, and rhodamine derivatives such as rhodamine B, rhodamine 6G, rhodamine 101, and sulfolhodamine 101.
  • cyanine derivatives such as 4-dicyanomethylene-2-methyl-6- (p-dimethylaminostyryl) -4H-pyran
  • rhodamine derivatives such as rhodamine B, rhodamine 6G, rhodamine 101, and sulfolhodamine 101.
  • Pyridine derivatives such as N, N-N'-bis (2,6-diisopropylphenyl) -1, 1-ethyl-2- (4- (p-dimethylaminophenyl) -1,3-butadienyl) -pyridinium-perchlorate
  • Derivatives such as, 6,7,12-tetraphenoxyperylene-3,4,9,10-bisdicarboximide, porphyrin derivatives, pyromethene derivatives, oxazine derivatives, pyrazine derivatives, naphthacene and dibenzodiindenoperylene, etc. Having a condensed aryl ring, derivatives thereof, and organometallic complexes Compounds and the like as preferred.
  • the second light emitting material is not particularly limited to these.
  • the pyrromethene derivative is a particularly suitable compound because it gives a high emission quantum yield and has good durability.
  • a compound represented by the general formula (1) is preferable because it emits light with high color purity.
  • the content of the luminescent material in the particulate color conversion material according to the embodiment of the present invention is the molar extinction coefficient of the compound, the emission quantum yield and the absorption intensity at the excitation wavelength, and the size of the color conversion material or color conversion member to be produced
  • the amount is 1.0 ⁇ 10 ⁇ 4 parts by mass to 30 parts by mass with respect to 100 parts by mass of the matrix resin, though it depends on the thickness, transmittance and the like.
  • the amount is more preferably 1.0 ⁇ 10 ⁇ 3 parts by mass to 10 parts by mass, and particularly preferably 5.0 ⁇ 10 ⁇ 3 parts by mass to 5 parts by mass.
  • a material having excellent moldability, transparency, heat resistance, and the like is suitably used as the matrix resin.
  • the matrix resin include, for example, a photocurable resist material having a reactive vinyl group such as an acrylic acid type, a methacrylic acid type, a polyvinyl cinnamate type, a ring rubber type, an epoxy resin, a silicone resin (silicone rubber, silicone Organopolysiloxane cured products such as gels (including crosslinked products), urea resins, fluorine resins, polycarbonate resins, acrylic resins, urethane resins, melamine resins, polyvinyl resins, polyamide resins, phenol resins, polyvinyl alcohol resins, polyvinyl butyral resins And polyester resins such as cellulose resins, aliphatic ester resins and aromatic ester resins, aliphatic polyolefin resins such as
  • an acrylic resin a copolymer resin containing an acrylate or methacrylate portion, a polyester resin, a cycloolefin resin, or an epoxy resin is used. Is preferred.
  • the glass transition temperature (Tg) of the matrix resin is not particularly limited, but is preferably from 30 ° C to 180 ° C.
  • Tg is 30 ° C. or higher, the molecular motion of the matrix resin due to the heat due to the incident light from the light source or the driving heat of the device is suppressed, and the change in the dispersion state of the light emitting material is suppressed, thereby preventing the deterioration of the durability. Can be.
  • Tg is 180 ° C. or lower, flexibility when formed into a sheet or the like can be ensured.
  • the Tg of the matrix resin is more preferably from 50 ° C to 170 ° C, further preferably from 70 ° C to 160 ° C, and particularly preferably from 90 ° C to 150 ° C.
  • the molecular weight of the matrix resin is not particularly limited depending on the type of the resin, but is preferably 3,000 to 1500,000. When the molecular weight is smaller than 3000, the resin becomes brittle, and the flexibility when molded becomes low. Further, when the molecular weight is larger than 1500000, there are problems that the viscosity at the time of molding becomes excessively large and the chemical stability of the resin itself is reduced.
  • the molecular weight of the matrix resin is more preferably 5,000 to 1,200,000, still more preferably 7,000 to 1,000,000, and particularly preferably 10,000 to 800,000.
  • the particulate color conversion material according to the embodiment of the present invention is, besides the light emitting material and the matrix resin, an antioxidant, a processing and heat stabilizer, a light resistance stabilizer such as an ultraviolet absorber, a plasticizer, and an epoxy compound. And the like. Curing agents such as amine, acid anhydride and imidazole, inorganic particles such as silica particles and silicone fine particles, and additives such as silane coupling agents can be contained.
  • antioxidants examples include, but are not particularly limited to, phenolic antioxidants.
  • the antioxidants may be used alone or in combination of two or more.
  • processing and heat stabilizers include, but are not particularly limited to, phosphorus-based stabilizers.
  • the stabilizers may be used alone or in combination.
  • the light resistance stabilizer include, for example, benzotriazoles, but are not particularly limited thereto. Further, the light resistance stabilizer may be used alone or in combination of two or more.
  • these additives do not inhibit light from a light source or light emission of a light-emitting material, it is preferable that these additives have a small absorption coefficient in the visible region.
  • the molar extinction coefficient ⁇ of these additives is preferably 200 or less, more preferably 100 or less, over the entire wavelength range of 400 nm to 800 nm. It is more preferably at most 80, particularly preferably at most 50.
  • the content of these additives depends on the molar extinction coefficient of the compound, the emission quantum yield and the absorption intensity at the excitation wavelength, and the color conversion material or color conversion to be produced. Although it depends on the size, thickness and transmittance of the member, it is preferably at least 1.0 ⁇ 10 ⁇ 3 parts by mass, more preferably at least 1.0 ⁇ 10 ⁇ 2 parts by mass, per 100 parts by mass of the matrix resin. More preferably, the content is more preferably 1.0 ⁇ 10 -1 part by mass or more. Further, the content of these additives is preferably 30 parts by mass or less, more preferably 15 parts by mass or less, and more preferably 10 parts by mass or less, based on 100 parts by mass of the matrix resin. More preferred.
  • the particulate color conversion material according to the embodiment of the present invention contains the compound represented by the general formula (1), it emits light with extremely high color purity. In addition, since it can be handled as a powder, it is easy to mix and use a plurality of types of particulate color conversion materials and finely adjust the wavelength conversion characteristics. For example, when white light is obtained by performing color conversion on a part of blue light, a green conversion material containing a light emitting material emitting green light and a red conversion material containing a light emitting material emitting red light are prepared. The white balance and color temperature of white light can be easily adjusted by adjusting the amount of mixing. Further, by controlling the particle diameter and shape of the color conversion material, the refractive index of the matrix resin, and the like, the color conversion characteristics can be adjusted, and functions other than the color conversion function can be provided. For example, a light scattering function can be exhibited.
  • each particle is individually independent, when highly active species such as radical species are generated by light irradiation at a high temperature condition, the high active species is entirely And the accelerated deterioration of the entire color conversion member can be suppressed.
  • the particulate color conversion material according to the embodiment of the present invention preferably has an average particle size of 0.010 ⁇ m or more and 100 ⁇ m or less, more preferably 0.010 ⁇ m or more and 30 ⁇ m or less, and 0.010 ⁇ m or more and 10 ⁇ m or less. Is more preferable.
  • the average particle size is obtained by observing the particle size distribution by microscopic observation or laser diffraction scattering method, but it is basically measured by microscopic observation. However, when the measurement result by the laser diffraction scattering method has a particle size of 1 ⁇ m or less, the particle size by the laser diffraction scattering method is adopted. In the case of microscopic observation, although not particularly limited, it can be obtained by measuring the particle size of about 100 isolated particles and calculating the average value.
  • the method for producing the particulate color conversion material according to the embodiment of the present invention is not particularly limited as long as the particulate color conversion material can be formed into particles containing a light emitting material and a matrix resin.
  • an interfacial polymerization method, a W / O-based in-liquid drying method, a Stover method, and a spray drying method, an in situ polymerization method, a phase separation method from an aqueous solution, a phase separation method from an organic solvent, a melting dispersion cooling method, and an airborne method It can be produced by a suspension coating method.
  • the particulate color conversion material according to the embodiment of the present invention may be used by itself. Further, from the viewpoint of further improving the applicability to the optical member, it is preferable to use a support containing a particulate color conversion material.
  • the support containing the particulate color conversion material according to the embodiment of the present invention can be used as a color conversion member.
  • the material of the support is not particularly limited, and known metals, resins, glass, ceramics, papers, and the like can be used. From the viewpoint of transparency and workability, the support is preferably made of resin. When the support is made of a resin, it is more preferable that the particulate color conversion material is dispersed in the support.
  • the term “dispersion” means that other substances are scattered in one phase, and the distribution may be uneven or uniform. However, when it is described that the particulate color conversion material is dispersed, a mode in which the particulate color conversion material is completely dissolved in the dispersion medium to form one uniform phase is excluded.
  • the support is made of a resin
  • the difference between the matrix resin of the particulate color conversion material and the resin forming the support has an SP value of 0.5 (cal / cm 3 ). It is preferably 0.5 or more.
  • the difference in SP value is 0.5 (cal / cm 3 ) 0.5 or more, the particulate color conversion material can be dispersed in the support without being dissolved.
  • the luminescent material is eluted also into the support, and the half width is reduced.
  • the difference between the SP values is more preferably 1.0 (cal / cm 3 ) 0.5 or more, still more preferably 1.5 (cal / cm 3 ) 0.5 or more, and 2.0 (cal / cm 3 ) 0.5 or more.
  • (Cal / cm 3 ) is particularly preferably 0.5 or more. If the difference in SP value is too large, the particles aggregate and cause quenching. Therefore, the upper limit is more preferably 4.0 (cal / cm 3 ) 0.5 or less, and more preferably 3.0 (cal / cm 3 ). cm 3 ) 0.5 or less, more preferably 2.5 (cal / cm 3 ) 0.5 or less.
  • the SP value of the matrix resin of the particulate color conversion material is preferably larger than the SP value of the resin forming the support.
  • Both the light emitting material emitting green light and the light emitting material emitting red light are preferably compounds represented by the general formula (1), since white light with high color reproducibility can be obtained. That is, as a preferred embodiment of the present invention, a first particulate color conversion material comprising a compound represented by the general formula (1) exhibiting light emission observed in a region having a peak wavelength of 500 nm or more and less than 580 nm and a first matrix resin is provided.
  • a second particulate color conversion material comprising a compound represented by the general formula (1) exhibiting light emission having a peak wavelength of 580 nm or more and 750 nm or less, a second matrix resin, and a support containing them. Color conversion member.
  • a plurality of types of supports containing a particulate color conversion material are combined.
  • a support containing a particulate color conversion material emitting green light and a support containing a particulate color conversion material emitting red light can be used.
  • the method of combining a plurality of supports depends on the shape of the supports, and examples thereof include a method of arranging them on the same plane and a method of stacking.
  • the SP value which is a solubility parameter of the matrix resin
  • the emission peak wavelength of the organic light emitting material shifts to a longer wavelength side as compared with the matrix resin having a small SP value. Therefore, by dispersing the organic light emitting material in the matrix resin having the optimum SP value, it is possible to optimize the emission peak wavelength of the organic light emitting material.
  • the SP value of the first matrix resin is SP 1 (cal / cm 3 ) 0.5 and the SP value of the second matrix resin is SP 2 (cal / cm 3 ) 0.5
  • SP 1 ⁇ SP 2 there is.
  • the difference between the emission peak wavelengths of the green light and the red light in the first particulate color conversion material and the second particulate color conversion material is smaller than the case where the organic light emitting material is dispersed in the same matrix resin. As a result, the color gamut is expanded.
  • SP 2 ⁇ 10.0 it is preferable that SP 2 ⁇ 10.0.
  • the emission peak wavelength of red light in the second particulate color conversion material is further increased, and as a result, deep red light can be emitted from the second particulate color conversion material.
  • SP 2 ⁇ 10.2 is more preferable
  • SP 2 ⁇ 10.4 is more preferable
  • SP 2 ⁇ 10.6 is particularly preferable.
  • SP 1 ⁇ 10.0 when SP 1 ⁇ 10.0, the emission peak wavelength of green light in the first particulate color conversion material is prevented from becoming longer, and as a result, the first particulate color conversion material and the second particulate color are converted. This is preferable because the difference in emission peak wavelength between green light and red light in the conversion material increases. From the viewpoint of increasing the effect, SP 1 ⁇ 9.8 is more preferable, SP 1 ⁇ 9.7 is more preferable, and SP 1 ⁇ 9.6 is particularly preferable.
  • SP 1 is not particularly limited, a matrix resin satisfying SP 1 ⁇ 7.0 can be suitably used because the organic light emitting material has good dispersibility. From the viewpoint of increasing the effect, SP 1 ⁇ 7.4 is more preferable, SP 1 ⁇ 7.8 is more preferable, and SP 1 ⁇ 8.0 is particularly preferable.
  • the dissolution parameter (SP value) is generally used, Poly. Eng. Sci. , Vol. 14, No. 2, pp. 147-154 (1974) and the like, and are values calculated from the types and ratios of the monomers constituting the resin using the Fedors estimation method.
  • the same method can be used to calculate a mixture of a plurality of types of resins.
  • the SP value of polymethyl methacrylate is 9.9 (cal / cm 3 ) 0.5
  • the SP value of polyethylene terephthalate (PET) is 11.6 (cal / cm 3 ) 0.5
  • a bisphenol A epoxy resin Can be calculated as 10.9 (cal / cm 3 ) 0.5 .
  • Table 1 shows typical SP values of the resins.
  • the first matrix resin and the second matrix resin can be used in any combination, for example, from the resins shown in Table 1.
  • the support that can be used in the present invention includes, in addition to the particulate color conversion material and the light-emitting material, a light-resistant dye such as a light-absorbing dye, a light-absorbing pigment, an antioxidant, a processing and heat stabilizer, and an ultraviolet absorber.
  • a light-resistant dye such as a light-absorbing dye, a light-absorbing pigment, an antioxidant, a processing and heat stabilizer, and an ultraviolet absorber.
  • An additive such as a coupling agent can be contained.
  • the color conversion substrate according to the embodiment of the present invention has a configuration including at least the particulate color conversion material or the color conversion member of the present invention.
  • the color conversion substrate has a plurality of color conversion layers on a transparent substrate.
  • the color conversion layer preferably includes a red conversion layer and a green conversion layer.
  • the red conversion layer is formed of a phosphor material that absorbs at least blue light and emits red light.
  • the green color conversion layer is formed of a phosphor material that absorbs at least blue light and emits green light.
  • a partition may be formed, and the color conversion layer is preferably disposed between the partition (recess).
  • the particle size of 100 isolated particles was measured using ECLIPSE L200N (manufactured by Nikon Corporation), and the average value was calculated. The average particle size was 14 ⁇ m. The particle size was measured by selecting a portion having the largest diameter.
  • ECLIPSE L200N manufactured by Nikon Corporation
  • the particle size was measured by selecting a portion having the largest diameter.
  • 300 parts by mass of cyclohexane as a solvent was mixed with 100 parts by mass of this resin. did.
  • the mixture was stirred and defoamed at 300 rpm for 30 minutes using a planetary stirring and defoaming apparatus “Mazerustar KK-400” (manufactured by Kurabo Industries) to obtain a resin solution for a support.
  • Examples 2 and 3 A color conversion member was prepared and evaluated in the same manner as in Example 1 except that the matrix resin and the support resin shown in Table 2 were used. Table 2 shows the results.
  • Comparative Example 2 The color conversion composition prepared in Example 1 was applied on a slide glass plate using a bar coater, heated at 100 ° C. for 20 minutes, and dried to prepare a color conversion member.

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Abstract

La présente invention aborde le problème de réalisation d'un bon équilibre entre l'amélioration de la reproductibilité des couleurs et la durabilité, en particulier un bon équilibre entre une émission de lumière ayant une pureté de couleur élevée et une durabilité par rapport à une composition de conversion de couleur qui est utilisée pour des dispositifs d'affichage à cristaux liquides ou des dispositifs d'éclairage à DEL, et par rapport à un matériau de conversion de couleur qui est utilisé pour des dispositifs d'affichage à cristaux liquides ou des dispositifs d'éclairage à DEL. La présente invention porte sur un matériau de conversion de couleur particulaire qui contient une résine de matrice et au moins un matériau électroluminescent, et qui est configuré de telle sorte que le matériau électroluminescent contienne un composé représenté par la formule générale (1).
PCT/JP2019/034006 2018-09-06 2019-08-29 Matériau de conversion de couleur, élément de conversion de couleur, unité de source de lumière, dispositif d'affichage, dispositif d'éclairage, substrat de conversion de couleur et encre WO2020050144A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201980055522.2A CN112639542B (zh) 2018-09-06 2019-08-29 颜色转换材料、颜色转换部件、光源单元、显示器、照明装置、颜色转换基板及油墨
JP2019549015A JP7380216B2 (ja) 2018-09-06 2019-08-29 色変換部材、光源ユニット、ディスプレイ、照明装置、色変換基板およびインク
KR1020217004840A KR20210055677A (ko) 2018-09-06 2019-08-29 색변환 재료, 색변환 부재, 광원 유닛, 디스플레이, 조명 장치, 색변환 기판 및 잉크

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JP2018-166657 2018-09-06
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