WO2022130786A1 - 色変換フィルム用組成物、色変換フィルム、色変換フィルムの製造方法、バックライトユニット及び液晶表示装置 - Google Patents

色変換フィルム用組成物、色変換フィルム、色変換フィルムの製造方法、バックライトユニット及び液晶表示装置 Download PDF

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WO2022130786A1
WO2022130786A1 PCT/JP2021/039169 JP2021039169W WO2022130786A1 WO 2022130786 A1 WO2022130786 A1 WO 2022130786A1 JP 2021039169 W JP2021039169 W JP 2021039169W WO 2022130786 A1 WO2022130786 A1 WO 2022130786A1
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color conversion
conversion film
compound
composition
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French (fr)
Japanese (ja)
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健太郎 豊岡
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Fujifilm Corp
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Fujifilm Corp
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Priority to US18/335,139 priority patent/US20230340330A1/en
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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 materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
    • C09K19/404—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing boron or phosphorus
    • 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
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • 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
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F21—LIGHTING
    • F21S—NON-PORTABLE LIGHTING DEVICES; SYSTEMS THEREOF; VEHICLE LIGHTING DEVICES SPECIALLY ADAPTED FOR VEHICLE EXTERIORS
    • F21S2/00—Systems of lighting devices, not provided for in main groups F21S4/00 - F21S10/00 or F21S19/00, e.g. of modular construction
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/1336—Illuminating devices
    • 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
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/123—Ph-Ph-Ph
    • 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
    • C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
    • C09K2219/03—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used in the form of films, e.g. films after polymerisation of LC precursor
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F21—LIGHTING
    • F21Y—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES F21K, F21L, F21S and F21V, RELATING TO THE FORM OR THE KIND OF THE LIGHT SOURCES OR OF THE COLOUR OF THE LIGHT EMITTED
    • F21Y2115/00—Light-generating elements of semiconductor light sources
    • F21Y2115/10—Light-emitting diodes [LED]

Definitions

  • the present disclosure relates to a composition for a color conversion film, a color conversion film, a method for manufacturing a color conversion film, a backlight unit, and a liquid crystal display device.
  • LCD Liquid Crystal Display
  • the color conversion film of the backlight unit included in the LCD contains a light emitting material that emits green light and red light by blue light, the white light in which the blue light, green light, and red light are mixed is extracted from the color conversion film. It becomes possible.
  • Examples of the color conversion film include a support, a layer (A) containing an organic light emitting material and a binder resin, and a layer (B) having an oxygen permeability of 1.0 cc / m 2 ⁇ day ⁇ atm or less.
  • a color conversion film is known (see, for example, International Publication No. 2017/052787).
  • the composition for a color conversion film used for producing a color conversion film is required to have excellent storage stability without causing gelation or the like during storage. Further, the color conversion film produced by using the composition for the color conversion film is required to have excellent light resistance. For the above reasons, it is desired to develop a composition for a color conversion film which can produce a color conversion film having excellent light resistance and has excellent storage stability.
  • the present disclosure has been made based on the above findings, and the problem to be solved is a composition for a color conversion film, which can produce a color conversion film having excellent light resistance and excellent storage stability, and a color conversion. It is an object of the present invention to provide a film, a method for manufacturing a color conversion film, a backlight unit, and a liquid crystal display device.
  • the excitation light combines at least two organic light-emitting materials that emit longer waves than the excitation light and have different emission peak wavelengths from each other, a photopolymerizable compound, and a protective group desorbed by heat.
  • a composition for a color conversion film comprising at least one of compounds having a crosslinkable group.
  • composition for a color conversion film according to ⁇ 1> wherein the photopolymerizable compound contains a radically polymerizable compound.
  • ⁇ 5> The first organic light emitting material exhibiting light emission observed in a region where the peak wavelength is 500 nm or more and less than 580 nm due to the excitation light having a wavelength of 400 nm or more and less than 500 nm, and the excitation light having a wavelength of 400 nm or more and less than 500 nm.
  • the composition for a color conversion film according to one.
  • X represents CR 7 or N.
  • R 1 to R 9 are independently hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, respectively.
  • the adjacent groups of R 1 to R 9 may be selected from the above to form a fused ring.
  • a color conversion film comprising a color conversion layer containing at least one of a polymer of a compound having a bonded crosslinkable group.
  • a method for producing a color conversion film which comprises forming a color conversion layer by curing a composition for a color conversion film containing at least one of compounds having a crosslinkable group to which a group is bonded.
  • a liquid crystal display device including the backlight unit and the liquid crystal cell unit according to ⁇ 9>.
  • a color conversion film having excellent light resistance can be produced, and a composition for a color conversion film having excellent storage stability, a color conversion film, a method for producing a color conversion film, a backlight unit and a liquid crystal display device. Can be provided.
  • FIG. 1 is a schematic cross-sectional view showing an embodiment of a color conversion film.
  • FIG. 2 is a schematic configuration sectional view showing an embodiment of the backlight unit of the present disclosure.
  • FIG. 3 is a schematic configuration sectional view showing an embodiment of the liquid crystal display device of the present disclosure.
  • the numerical range indicated by using "-" includes the numerical values before and after "-" as the minimum value and the maximum value, respectively.
  • the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of the numerical range described in another stepwise description. ..
  • the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
  • each component may contain a plurality of applicable substances. When a plurality of substances corresponding to each component are present in the composition, the content or content of each component is the total content or content of the plurality of substances present in the composition unless otherwise specified. Means quantity.
  • (meth) acrylic is a term used in a concept that includes both acrylic and methacrylic.
  • (meth) acrylic acid is a term used in a concept that includes both acrylic acid and methacrylic acid.
  • (meth) acrylate is a term used in a concept that includes both acrylate and methacrylate.
  • (meth) acryloyl is a term used in a concept that includes both acryloyl and methacryloyl.
  • (meth) acryloxy is a term used in a concept that includes both acryloxy and methacryloxy.
  • the "photopolymerizable compound” means a compound that polymerizes by irradiation with active light
  • the "photopolymerizable compound” means a polymerized photopolymerizable compound.
  • the term “layer” includes not only the case where the layer is formed in the entire region when observing the region where the layer is present, but also the case where the layer is formed only in a part of the region. Is done.
  • the "light emitting material” refers to a material that emits light having a wavelength different from that of the light when irradiated with light.
  • excitation light refers to light that excites an organic light emitting material to emit light.
  • the peak wavelength of light emission exhibited by the organic light emitting material is measured as follows. First, the peak wavelength of the organic light emitting material contained in the composition for a color conversion film can be confirmed by adding the composition for a color conversion film to a solvent to prepare a solution and measuring the emission spectrum of the solution. As the solvent, toluene, dichloromethane, tetrahydrofuran and the like can be used, and toluene is preferable.
  • the peak wavelength of light emission exhibited by the organic light emitting material contained in the color conversion layer included in the color conversion film is measured as follows.
  • a color conversion film is placed on a planar light emitting device capable of emitting excitation light having a wavelength of 400 nm or more and less than 500 nm so that the support is on the light emitting device side, and a prism sheet is placed on the color conversion film.
  • a current is passed through the planar light emitting device and the excitation light is applied to the color conversion film, white light including blue light, green light and red light is observed.
  • CS-1000 is used to obtain the emission spectrum of the white light, and from the emission spectrum, the emission observed in the region where the peak wavelength is 500 nm or more and less than 580 nm and the emission observed in the region where the peak wavelength is 580 nm or more and 750 nm or less. Check the light emission.
  • the thickness of each layer can be controlled by adjusting the coating amount of the coating liquid and the liquid solid content concentration (% by mass) so as to obtain a desired thickness. Also.
  • the thickness can be determined from a cross-sectional image of a color conversion film obtained by scanning electron microscopy (SEM) or transmission electron microscopy (TEM).
  • SEM scanning electron microscopy
  • TEM transmission electron microscopy
  • composition for color conversion film The composition for a color conversion film of the present disclosure emits a longer wave than the excitation light by the excitation light, and at least two kinds of organic light emitting materials having different peak wavelengths of emission from each other, and a photopolymerizable compound and heat are used to remove the composition. Includes at least one of the compounds having a crosslinkable group to which a protective group to be released is attached.
  • the above composition for a color conversion film can produce a color conversion film having excellent storage stability and excellent light resistance.
  • the composition for a color conversion film of the present disclosure contains at least one of a photopolymerizable compound and a photopolymerizable compound and a compound having a crosslinkable group to which a protective group desorbed by heat is bonded. It is presumed that the color conversion layer formed by curing the composition for a color conversion film on the support has a crosslinked structure of the photopolymerizable compound and has excellent light resistance. Further, the composition for a color conversion film of the present disclosure is presumed to have excellent storage stability because the cross-linking reaction does not proceed at room temperature in a shielding environment.
  • compositions for color conversion films of the present disclosure include at least two organic light emitting materials having different peak wavelengths of light emission.
  • the organic light emitting material is a first organic light emitting material exhibiting light emission observed in a region having a peak wavelength of 500 nm or more and less than 580 nm by excitation light having a wavelength of 400 nm or more and less than 500 nm, and an excitation having a wavelength of 400 nm or more and less than 500 nm.
  • a second organic light emitting material exhibiting light emission observed in a region having a peak wavelength of 580 nm or more and 750 nm or less by at least one of light and light emission of the first organic light emitting material is included.
  • the content of the first organic light emitting material is preferably 40 parts by mass to 80 parts by mass with respect to 100 parts by mass of the total amount of the organic light emitting material contained in the composition for a color conversion film. , 50 parts by mass to 75 parts by mass, more preferably.
  • the content of the second organic light emitting material is preferably 20 parts by mass to 60 parts by mass with respect to 100 parts by mass of the total amount of the organic light emitting material contained in the composition for a color conversion film. , 25 parts by mass to 50 parts by mass, more preferably.
  • Examples of the organic light emitting material include compounds having a condensed aryl ring and derivatives thereof.
  • Examples of the fused aryl ring include naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthalene, triphenylene, perylene, fluoranthene, fluorene and indene.
  • Examples of the organic light emitting material include compounds having a heteroaryl ring, derivatives thereof, borane compounds and the like.
  • heteroaryl ring examples include furan, pyrrole, thiophene, silol, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazolepyridine, phenanthroline, pyridine, pyrazine, etc. Examples thereof include naphthylidine, quinoxaline and pyrolopyridine.
  • Examples of the organic light emitting material include stilbene compounds, aromatic acetylene compounds, tetraphenylbutadiene compounds, aldazine compounds, pyrromethene compounds, and diketopyrrole [3,4-c] pyrrole compounds.
  • Examples of the stilbene compound include 1,4-dystylylbenzene, 4,4'-bis (2- (4-diphenylaminophenyl) ethenyl) biphenyl and 4,4'-bis (N- (stilbene-4-yl)-). N-Phenylamino) stilbene and the like can be mentioned.
  • organic light-emitting material examples include coumarin compounds such as coumarin 6, coumarin 7, and coumarin 153, azole compounds such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and metal complexes thereof, and indocyanine green.
  • coumarin compounds such as coumarin 6, coumarin 7, and coumarin 153
  • azole compounds such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and metal complexes thereof, and indocyanine green.
  • cyanine-based compounds examples include cyanine-based compounds, xanthene-based compounds such as fluorescein, eosin and rhodamine, and thioxanthene-based compounds.
  • organic light emitting material examples include polyphenylene compounds, naphthalimide compounds, phthalocyanine compounds and their metal complexes, porphyrin compounds and their metal complexes, oxazine compounds such as Nile Red and Nile Blue, helisene compounds, and N, N'.
  • aromatic amine compounds such as -diphenyl-N, N'-di (3-methylphenyl) -4,4'-diphenyl-1,1'-diamine.
  • organic light emitting material examples include organic metal complex compounds such as iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os), and renium (Re). Can be mentioned. However, in the present disclosure, the organic light emitting material is not limited to those described above.
  • the organic light emitting material may be a fluorescent light emitting material or a phosphorescent light emitting material, but a fluorescent light emitting material is preferable in order to achieve excellent color purity.
  • a compound having a condensed aryl ring or a derivative thereof is preferable because it is excellent in thermal stability and photostability.
  • 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 trifluoride complex is also preferable because it has a small half-value width and can emit light with high efficiency.
  • the first organic light emitting material includes a coumarin compound such as coumarin 6, coumarin 7 and coumarin 153; a cyanine compound such as indocyanine green; a fluorescein compound such as fluorescein, fluorescein isothiocyanate and carboxyfluorescein diacetate; and a phthalocyanine such as phthalocyanine green.
  • a coumarin compound such as coumarin 6, coumarin 7 and coumarin 153
  • a cyanine compound such as indocyanine green
  • a fluorescein compound such as fluorescein, fluorescein isothiocyanate and carboxyfluorescein diacetate
  • a phthalocyanine such as phthalocyanine green.
  • Perylene compounds such as diisobutyl-4,10-dicyanoperylene-3,9-dicarboxylate; pyromethene compounds; stilben compounds; oxazine compounds; naphthalimide compounds; pyrazine compounds; benzoimidazole compounds; benzoxazole compounds; benzothiazole compounds Imidazole pyridine compounds; azole compounds; compounds having a condensed aryl ring such as fluorescein; derivatives thereof: aromatic amine compounds; and organic metal complex compounds are preferable.
  • the first organic light emitting material is not particularly limited to these.
  • Examples of the second organic light emitting material include cyanine compounds such as 4-dicyanomethylene-2-methyl-6- (p-dimethylaminostyryl) -4H-pyran; Rhodamine B, Rhodamine 6G, Rhodamine 101 and Sulfolodamine 101.
  • cyanine compounds such as 4-dicyanomethylene-2-methyl-6- (p-dimethylaminostyryl) -4H-pyran; Rhodamine B, Rhodamine 6G, Rhodamine 101 and Sulfolodamine 101.
  • Rhodamine compounds Pyridine compounds such as 1-ethyl-2- (4- (p-dimethylaminophenyl) -1,3-butadienyl) -pyridinium-parklorate; N, N'-bis (2,6-diisopropylphenyl) Perylene compounds such as -1,6,7,12-tetraphenoxyperylene-3,4: 9,10-bisdicarboimide; porphyrin compounds; pyromethene compounds; oxazine compounds; pyrazine compounds; Compounds having a fused aryl ring of the above; derivatives thereof; as well as organic metal complex compounds and the like are mentioned as suitable ones.
  • the second organic light emitting material is not particularly limited to these.
  • the pyrromethene compound is preferable because it gives an excellent emission quantum yield and has good durability.
  • the pyrromethene compound for example, the compound represented by the above general formula (1) is preferable because it exhibits excellent light emission with excellent color purity.
  • at least one of the first organic light emitting material and the second organic light emitting material is preferably a pyrromethene compound.
  • the pyrromethene compound for example, the compound represented by the general formula (1) described later is preferable because it exhibits light emission with excellent color purity.
  • the organic light emitting material is preferably a compound represented by the following general formula (1). Even when the organic light emitting material is represented by the following general formula (1), the composition for a color conversion film may contain an organic light emitting material other than the organic light emitting material represented by the general formula (1). can.
  • R 1 to R 9 are independently hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, respectively.
  • the adjacent groups of R 1 to R 9 may be selected from the above to form a fused ring.
  • the hydrogen atom may be a deuterium atom. This also applies to the compounds described below or their partial structures.
  • a substituted or unsubstituted aryl group having 6 to 40 carbon atoms has all carbon atoms of 6 to 40 including the carbon number contained in the substituent substituted with the aryl group. It is an aryl group. The same applies to other substituents that specify the number of carbon atoms.
  • the substituents in the case of substitution include 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 and an alkylthio group.
  • Aryl ether group, aryl thioether group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, nitro group, silyl group, siroxanyl group, boryl A group and a phosphine oxide group are preferable, and a specific substituent which is preferable in the description of each substituent is preferable. Further, these substituents may be further substituted with the above-mentioned substituents.
  • the alkyl group is 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. It indicates a group, which may or may not have a substituent.
  • the additional substituent when substituted is not particularly limited, and examples thereof include an alkyl group, a halogen, an aryl group, a heteroaryl group, and the like, and this point is also common to the following description.
  • the number of carbon atoms of the alkyl group is not particularly limited, but is preferably in the range of 1 or more and 20 or less, and more preferably 1 or more and 8 or less in terms of availability and cost.
  • the cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group and an adamantyl group, which may or may not have a substituent. May be good.
  • the number of carbon atoms in the alkyl group moiety is not particularly limited, but is preferably in the range of 3 or more and 20 or less.
  • the heterocyclic group refers to an aliphatic ring having an atom other than carbon such as a pyran ring, a piperidine ring and a cyclic amide in the ring, which may or may not have a substituent. good.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.
  • the alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group and a butazienyl 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 an unsaturated alicyclic hydrocarbon group containing a double bond such as, for example, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, etc., even if it has a substituent. You do not have to have it.
  • the alkynyl group refers to 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 a functional group to which an aliphatic hydrocarbon group is bonded via an ether bond such as a methoxy group, an ethoxy group and a propoxy group, and the aliphatic hydrocarbon group has a substituent. You do not have to have.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.
  • the alkylthio group is a group in which the oxygen atom of the ether bond of the alkoxy group is replaced with a sulfur atom.
  • the hydrocarbon group of the alkylthio group may or may not have a substituent.
  • the number of carbon atoms of the alkylthio group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.
  • the aryl ether group indicates a functional group to which an aromatic hydrocarbon group is bonded via an ether bond, for example, a phenoxy group, and the aromatic hydrocarbon group has or does not have a substituent. May be good.
  • the number of carbon atoms of the aryl ether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.
  • the arylthio ether group is one in which the oxygen atom of the ether bond of the aryl ether group is replaced 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.
  • the aryl group is, for example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthrasenyl group, a benzophenanthril group, a benzoanthrase.
  • Aromatic hydrocarbon groups such as an Nyl group, a chrysenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a benzofluoranthenyl group, a dibenzoanthrasenyl group, a peryleneyl group and a helisenyl group are shown.
  • a phenyl group a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, an anthrasenyl group, a pyrenyl group, a fluoranthenyl group or a triphenylenyl group is preferable.
  • the aryl group may or may not have a substituent.
  • the number of carbon atoms 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 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, an anthracenyl group, and preferably a phenyl group or a biphenyl.
  • Groups, turphenyl groups and naphthyl groups are more preferred. More preferably, it is a phenyl group, a biphenyl group, a terphenyl group, and a phenyl group is particularly preferable.
  • 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 anthrasenyl group, preferably a phenyl group, a biphenyl group or a ter.
  • a phenyl group or a naphthyl group is more preferable. Particularly preferred is a phenyl group.
  • the heteroaryl group is, for example, a pyridyl group, a furanyl group, a thienyl group, a quinolinyl group, an isoquinolinyl group, a pyrazinyl group, a pyrimidyl group, a pyridadinyl group, a triazinyl group, a naphthyldinyl group, a cinnolinyl group, a phthalazinyl group, a quinoxalinyl group, a quinazolinyl group, and the like.
  • Non-carbon atoms such as a group, a dihydroindenocarbazolyl group, a benzoquinolinyl group, an acridinyl group, a dibenzoacrydinyl group, a benzoimidazolyl group, an imidazole pyridyl group, a benzoxazolyl group, a benzothiazolyl group and a phenanthrolinyl group.
  • the naphthyldinyl group is any of 1,5-naphthyldinyl group, 1,6-naphthyldinyl group, 1,7-naphthyldinyl group, 1,8-naphthyldinyl group, 2,6-naphthyldinyl group and 2,7-naphthyldinyl group.
  • the heteroaryl group may or may not have a substituent.
  • the number of carbon atoms of the heteroaryl group is not particularly limited, but is preferably in the range of 2 or more and 40 or less, and more preferably 2 or more and 30 or less.
  • the heteroaryl group is a pyridyl group, a furanyl group, a thienyl group, a quinolinyl group, a pyrimidyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, A dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzoimidazolyl group, an imidazole pyridyl group, a benzoxazolyl group, a benzothiazolyl group or a phenanthrolinyl group is preferable, and a pyridyl group, a furanyl group, a thienyl group or a quinolinyl group is more preferable. .. Particularly preferred is a pyridyl group, a furanyl group, a thienyl group or a quinolinyl
  • the heteroaryl group is a pyridyl group, a furanyl group, a thienyl group, a quinolinyl group, a pyrimidyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofura.
  • Nyl group dibenzothienyl group, carbazolyl group, benzoimidazolyl group, imidazole pyridyl group, benzoxazolyl group, benzothiazolyl group or phenanthrolinyl group are preferable, and pyridyl group, furanyl group, thienyl group or quinolinyl group is more preferable. Particularly preferred is a pyridyl group.
  • Halogen refers to an atom selected from fluorine, chlorine, bromine and iodine.
  • the carbonyl group, the carboxyl group, the oxycarbonyl group and the carbamoyl group may or may not have a substituent.
  • substituents include an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group and the like, and these substituents may be further substituted.
  • the amino group is a substituted or unsubstituted amino group.
  • substituents in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group and the like.
  • aryl group and the heteroaryl group a phenyl group, a naphthyl group, a pyridyl group or a quinolinyl group is preferable. These substituents may be further substituted.
  • the number of carbon atoms is not particularly limited, but is preferably 2 or more and 50 or less, more preferably 6 or more and 40 or less, and particularly preferably 6 or more and 30 or less.
  • the silyl group is, 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, or a tri.
  • Indicates an arylsilyl group such as a phenylsilyl group and a trinaphthylsilyl group.
  • Substituents on silicon may be further substituted.
  • the number of carbon atoms of the silyl group is not particularly limited, but is preferably in the range of 1 or more and 30 or less.
  • the siroxanyl group means, for example, a silicon compound group via an ether bond such as a trimethylsyloxanyl 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 the above, an aryl group or an aryl ether group is preferable.
  • the fused ring and the aliphatic ring formed between the adjacent substituents are conjugated or non-conjugated by any adjacent two substituents (for example, R 1 and R 2 of the general formula (1)) bonded to each other. It means to form a circular skeleton of.
  • Examples of the constituent elements of such a fused ring and an aliphatic ring include carbon, nitrogen, oxygen, sulfur, phosphorus and silicon. Further, the condensed ring and the aliphatic ring may be fused with yet another ring.
  • the compound represented by the general formula (1) exhibits an excellent emission quantum yield and has a small half-value width of the emission spectrum, so that both efficient color conversion and excellent color purity can be achieved. can. Furthermore, the compound represented by the general formula (1) has various properties such as luminous efficiency, color purity, thermal stability, photostability and dispersibility by introducing an appropriate substituent at an appropriate position. And physical properties can be adjusted.
  • R 1 , R 3 , R 4 and R 6 is a substituted or unsubstituted alkyl group, substituted or absent, as compared to the case where R 1 , R 3 , R 4 and R 6 all represent hydrogen atoms. It exhibits better thermal and photostability when it represents a group selected from the group containing substituted aryl groups and substituted or unsubstituted heteroaryl groups.
  • the alkyl group includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and the like.
  • Alkyl groups having 1 to 6 carbon atoms such as sec-butyl group, tert-butyl group, pentyl group or hexyl group are preferable.
  • a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group or a tert-butyl group is preferable from the viewpoint of excellent thermal stability.
  • the tert-butyl group having a high sterically bulk is more preferable 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, and more preferably.
  • the heteroaryl group is preferably a pyridyl group, a quinolinyl group or a thienyl group, and more preferably a pyridyl group.
  • the heteroaryl group represents a quinolinyl group. Particularly preferably, it represents a pyridyl group.
  • R 1 , R 3 , R 4 and R 6 all independently represent substituted or unsubstituted alkyl groups, they are preferable because they have good solubility in a binder resin or a solvent.
  • the alkyl group a methyl group is preferable from the viewpoint of easy synthesis and easy availability of raw materials.
  • R 1 , R 3 , R 4 and R 6 all independently represent substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups, they exhibit better thermal stability and photostability. Therefore, it is preferable. In this case, it is more preferable that R 1 , R 3 , R 4 and R 6 all independently represent substituted or unsubstituted aryl groups.
  • R 1 , R 3 , R 4 and R 6 all independently represent substituted or unsubstituted aryl groups, for example, R 1 ⁇ R 4 , R 3 ⁇ R 6 , R 1 ⁇ R 3 Alternatively, it is preferable to introduce a plurality of types of substituents such as R 4 ⁇ R 6 and the like.
  • " ⁇ " indicates that it is a base of a different structure.
  • R 1 ⁇ R 4 indicates that R 1 and R 4 are based on different structures.
  • R 1 ⁇ R 3 or R 4 ⁇ R 6 it is preferable because the luminous efficiency and the color purity can be improved in a well-balanced manner.
  • one or more aryl groups that affect the color purity are introduced into the pyrrole rings on both sides, and the aryls that affect the luminous efficiency at other positions. Since the group can be introduced, both of these properties can be improved.
  • an aryl group substituted with an electron donating group is preferable.
  • An electron-donating group is an atomic group that donates an electron to an atomic group substituted by an inductive effect or a resonance effect in organic electron theory.
  • Examples of the electron-donating group include those having a negative value as the substituent constant ( ⁇ p (para)) of Hammett's law.
  • the Substituent constant ( ⁇ p (para)) of Hammett's rule can be quoted from the 5th revised edition of the Basics of Chemistry (II-380).
  • the electron donating group examples include an alkyl group (methyl group ⁇ p: ⁇ 0.17), an alkoxy group (methoxy group ⁇ p: ⁇ 0.27) and an amino group ( ⁇ NH 2 ⁇ p: ⁇ ). 0.66) and the like can be mentioned.
  • 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 or a methoxy group is more preferable.
  • a tert-butyl group or a methoxy group is particularly preferable, and when these are used as the above-mentioned electron donating groups, in the compound represented by the general formula (1), quenching due to aggregation of molecules is prevented. be able to.
  • the substitution position of the substituent is not particularly limited, but since 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 necessary to suppress the twist of the bond. It is preferable to combine it with a position or a para position.
  • an aryl group having a bulky substituent such as a tert-butyl group, an adamantyl group, or a methoxy group is preferable.
  • R 1 , R 3 , R 4 and R 6 each independently represent a substituted or unsubstituted aryl group
  • R 1 , R 3 , R 4 and R 6 are independently substituted or unsubstituted, respectively. It preferably represents a phenyl group.
  • R 1 , R 3 , R 4 and R 6 are selected from the following Ar-1 to Ar-6, respectively.
  • preferred combinations of R 1 , R 3 , R 4 and R 6 include, but are not limited to, the combinations shown in Table 1-1 to Table 1-11.
  • the black circle means a joint with the main skeleton.
  • R 2 and R 5 are preferably any of a hydrogen atom, an alkyl group, a carbonyl group, an oxycarbonyl group and an aryl group.
  • a hydrogen atom or an alkyl group is preferable from the viewpoint of thermal stability, and a hydrogen atom is more preferable from the viewpoint of easily obtaining a narrow full width at half maximum in the emission spectrum.
  • 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.
  • R 8 and R 9 represent a fluorine or a fluorine-containing aryl group because they are stable to excitation light and a better emission quantum yield can be obtained.
  • R 8 and R 9 are fluorine because of the ease of synthesis.
  • 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.
  • X is CR 7 from the viewpoint of light stability.
  • the substituent R 7 has a great influence on the durability of the compound represented by the general formula (1), that is, the decrease in the emission intensity of this compound with time.
  • R 7 is a hydrogen atom
  • the reactivity of this portion is high, so that this portion easily reacts with water and oxygen in the air. This may cause decomposition of the compound represented by the general formula (1).
  • R 7 represents a substituent having a large degree of freedom of movement of the molecular chain such as an alkyl group, the reactivity is lowered, but the compounds aggregate with time in the color conversion film, resulting in the aggregation.
  • R7 is preferably a group that is rigid, has a small degree of freedom of motion, and does not easily cause aggregation, and specifically, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. It is preferably either.
  • X is CR 7 and R 7 represents a substituted or unsubstituted aryl group.
  • R 7 represents a substituted or unsubstituted aryl group.
  • aryl group a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group or an anthrasenyl group is preferable from the viewpoint of not impairing the emission wavelength.
  • R7 and the pyrromethene skeleton are used. It is preferable to moderately suppress the twist of the carbon-carbon bond with.
  • R7 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 is preferable, and the substituted or unsubstituted naphthyl group is preferable.
  • a phenyl group a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. Particularly preferably, it represents a substituted or unsubstituted phenyl group.
  • R 7 preferably represents a moderately bulky substituent.
  • R 7 has a certain bulk height, it is possible to prevent molecular aggregation, and as a result, the luminous efficiency and durability of the compound represented by the general formula (1) are further improved.
  • a more preferable example of the bulky substituent is the structure of R 7 represented by the following general formula (2).
  • r is a hydrogen atom, 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 aryl ether group or an aryl.
  • aryl group From thioether group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, nitro group, silyl group, siroxanyl group, boryl group and phosphine oxide group Selected from the group of k is an integer of 1 to 3. When k is 2 or more, r may be the same or different.
  • r preferably represents a substituted or unsubstituted aryl group.
  • aryl groups a phenyl group or a naphthyl group is particularly preferable.
  • k in the general formula (2) is preferably 1 or 2, and more preferably 2 from the viewpoint of further preventing molecular aggregation. 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 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, and a methyl group, an ethyl group, etc. More preferably, a tert-butyl group or a methoxy group. From the viewpoint of dispersibility, a tert-butyl group or a methoxy group is particularly preferable. The fact that r represents a tert-butyl group or a methoxy group is also effective from the viewpoint of preventing quenching due to aggregation of molecules.
  • At least one of R 1 to R 7 represents an electron-withdrawing group.
  • at least one of R 1 to R 6 represents an electron-withdrawing group
  • R 7 represents an electron-withdrawing group
  • it represents an electron-withdrawing group
  • R 7 represents an electron-withdrawing group.
  • An electron-withdrawing group is also called an electron-accepting group, and is an atomic group that attracts electrons from an atomic group substituted by an inductive effect or a resonance effect in organic electron theory.
  • Examples of the electron-withdrawing group include those having a positive value as the substituent constant ( ⁇ p (para)) of Hammett's law.
  • the Substituent constant ( ⁇ p (para)) of Hammett's rule can be quoted from the 5th revised edition of the Basics of Chemistry (II-380).
  • the phenyl group also takes a positive value as described above, in the present disclosure, the phenyl group is not included in the electron-withdrawing group.
  • electron-withdrawing groups examples include -F ( ⁇ p: +0.06), -Cl ( ⁇ p: +0.23), -Br ( ⁇ p: +0.23), -I ( ⁇ p: +0.18), and so on.
  • -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: +0.69 when R 12 is a methyl group
  • ⁇ NO 2 ⁇ p: +0.81
  • R 12 is independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, substituted or absent. It represents a substituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms. Specific examples of each of these groups include the same examples as described above.
  • Preferred electron-withdrawing groups from the viewpoint of degradability include fluorine, a fluorine-containing aryl group, a fluorine-containing heteroaryl group, a fluorine-containing alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, a substituted or no substituent.
  • Examples include substituted amide groups, substituted or unsubstituted sulfonyl groups and cyano groups.
  • More preferred electron-withdrawing groups include a fluorine-containing alkyl group, a fluorine-containing aryl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group and a cyano group. According to the above-mentioned electron-withdrawing group, concentration quenching can be prevented and the emission quantum yield can be improved. Particularly preferred electron-withdrawing groups are substituted or unsubstituted ester groups.
  • R 1 , R 3 , R 4 and R 6 are all independently substituted or unsubstituted, respectively.
  • X is CR 7 and R 7 represents a group represented by the general formula (2).
  • R 7 represents a group represented by the general formula (2) in which r is contained as a substituted or unsubstituted phenyl group.
  • the compound represented by the general formula (1) can be synthesized, for example, by the methods described in JP-A-8-509471 and JP-A-2000-208262. That is, the desired pyrromethene-based metal complex can be obtained by reacting the pyrromethene compound and the metal salt in the presence of a base.
  • the pyrromethene-boron trifluoride complex refer to J.I. Org. Chem. , Vol. 64, No. 21, pp. 7813-7819 (1999), Angew. Chem. , Int. Ed. Engl. , Vol. 36, pp.
  • the compound represented by the general formula (1) can be synthesized with reference to the method described in 1333-1335 (1997) and the like.
  • the compound represented by the following general formula (3) and the compound represented by the general formula (4) are heated in 1,2-dichloroethane in the presence of phosphorus oxychloride, and then the following general formula (5) is used.
  • a method of reacting the represented compound in 1,2-dichloroethane in the presence of triethylamine to obtain the compound represented by the general formula (1) can be mentioned.
  • R 1 to R 9 are the same as the above description.
  • J represents a halogen.
  • a method of forming a carbon-carbon bond by a coupling reaction between a halogenated compound and a boronic acid or a boronic acid esterified compound can be mentioned, but is limited to this. It's not something.
  • a method of forming a carbon-nitrogen bond by a coupling reaction between a halogenated compound and an amine or carbazole compound under a metal catalyst such as palladium can be mentioned. However, it is not limited to this.
  • the composition for a color conversion film may appropriately contain other compounds in addition to the compound represented by the general formula (1), if necessary.
  • the composition for a color conversion film may contain an assist dopant such as rubrene in order to further increase the energy transfer efficiency from the excitation light to the compound represented by the general formula (1).
  • a desired organic light emitting material for example, an organic light emitting material such as a coumarin dye or a rhodamine dye may be added. can.
  • known light emitting materials such as inorganic phosphors, fluorescent pigments, fluorescent dyes and quantum dots can be added in combination.
  • organic light emitting material other than the compound represented by the general formula (1), but the present disclosure is not particularly limited thereto.
  • composition for a color conversion film may contain two or more kinds of organic light emitting materials.
  • the content of the organic light emitting material with respect to 100 parts by mass of the total solid content contained in the composition for the color conversion film is preferably 0.005 part by mass to 1 part by mass, preferably 0.007. It is more preferably parts by mass to 0.7 parts by mass, and even more preferably 0.01 parts by mass to 0.5 parts by mass.
  • the photopolymerizable compound is not particularly limited, and conventionally known compounds can be appropriately selected and used. Further, the composition for a color conversion film of the present disclosure may contain two or more kinds of photopolymerizable compounds.
  • the photopolymerizable compound preferably contains a radically polymerizable compound or a cationically polymerizable compound.
  • the photopolymerizable compound may include a radically polymerizable compound and a cationically polymerizable compound.
  • the sum of the contents of the radically polymerizable compound and the cationically polymerizable compound with respect to the total amount of 100 parts by mass of the photopolymerizable compound contained in the composition for a color conversion film is preferably 50 parts by mass or more, preferably 60 parts by mass or more. Is more preferable, and 70 parts by mass or more is further preferable.
  • the content of the radically polymerizable compound and the cationically polymerizable compound is preferably 100 parts by mass or less with respect to 100 parts by mass of the total amount of the photopolymerizable compound contained in the composition for a color conversion film.
  • radically polymerizable compound As the radically polymerizable compound, conventionally known compounds can be appropriately selected and used. Examples of the radically polymerizable compound include a compound having an ethylenically unsaturated double bond, a compound having a conjugated diene moiety, a compound having a maleimide moiety, and a thiol compound that is cured by a thiol-ene reaction.
  • Examples of the compound having a conjugated diene moiety include compounds in which a substituent is introduced into butadiene or isoprene to make it non-volatile, polyacetylene and its derivatives, polyphenylacetylene and the like.
  • Examples of the compound having a maleimide moiety include a polymer compound having a maleimide group in the side chain, a compound having two or more maleimide groups in the molecule, and a compound having a (meth) acryloyl group and a maleimide group in the molecule. Can be done.
  • Thiol compounds cured by the thiol-ene reaction include pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakis (3-mercaptobutyrate) and 1,3,5-tris (3-mercaptobutyloxyethyl) -1, Examples thereof include compounds having an aliphatic thiol group such as 3,5-triazine-2,4,6- (1H, 3H, 5H) -trione.
  • a compound having an ethylenically unsaturated double bond is preferable, and it is more preferable to contain a compound having an acryloyl group in the molecule.
  • phenoxyhexaethylene glycol mono (meth) acrylate which is a (meth) acrylate of a compound having polyethylene glycol added to a phenyl group, or an average of 2 mol of propylene oxide was added.
  • Examples thereof include 4-normal Nonylphenoxypentaethylene glycol monopropylene glycol (meth) acrylate, which is a (meth) acrylate of a compound obtained by adding polyethylene glycol to which an average of 5 mol of ethylene oxide is added to nonylphenol. Also mentioned is 4-normalmalnonylphenoxyoctaethylene glycol (meth) acrylate (M-114, manufactured by Toagosei Co., Ltd.), which is an acrylate of a compound obtained by adding polyethylene glycol to which an average of 8 mol of ethylene oxide is added to nonylphenol.
  • M-114 manufactured by Toagosei Co., Ltd.
  • Examples of the compound having an ethylenically unsaturated double bond include a compound having (meth) acryloyl groups at both ends of the alkylene oxide chain, and an alkylene oxide chain in which an ethylene oxide chain and a propylene oxide chain are bonded at random or in a block.
  • Compounds having (meth) acryloyl groups at both ends can be mentioned.
  • Examples of the above compounds include tetraethylene glycol di (meth) acrylate, pentaethylene glycol di (meth) acrylate, hexaethylene glycol di (meth) acrylate, heptaethylene glycol di (meth) acrylate, and octaethylene glycol di (meth) acrylate. Examples thereof include nonaethylene glycol di (meth) acrylate, decaethylene glycol di (meth) acrylate, and compounds having (meth) acryloyl groups at both ends of a 12 mol ethylene oxide chain.
  • a compound obtained by modifying bisphenol A with alkylene oxide and having (meth) acryloyl groups at both ends can be preferably used.
  • alkylene oxide denaturation include ethylene oxide denaturation, propylene oxide denaturation, butylene oxide denaturation, pentylene oxide denaturation and hexylene oxide denaturation.
  • a compound which is modified with ethylene oxide to bisphenol A and has (meth) acryloyl groups at both ends is preferable.
  • Examples of the above compounds include 2,2-bis (4-((meth) acryloxidiethoxy) phenyl) propane (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., NK ester BPE-200) and 2,2-bis (4).
  • a compound having more than two (meth) acryloyl groups in one molecule has 3 mol or more of groups to which an alkylene oxide group can be added in the molecule as a central skeleton, to which ethylene oxide groups, propylene oxide and butylene are added. It is obtained by (meth) acrylate-forming an alcohol obtained by adding an alkylene oxide group such as an oxide.
  • Examples of the compound that can form a central skeleton include glycerin, trimethylolpropane, pentaerythritol, dipentaerythritol, and isocyanurate ring.
  • Examples of the compound include EO (ethylene oxide) 3 mol modified triacrylate of trimethylolpropane, EO 6 mol modified triacrylate of trimethylolpropane, EO9 mol modified triacrylate of trimethylolpropane, and EO12 mol modified triacrylate of trimethylolpropane.
  • Examples of the above compounds include EO3 molar modified triacrylate of glycerin (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., A-GLY-3E) and EO9 molar modified triacrylate of glycerin (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., A-GLY-9E).
  • EO6 mol PO propylene oxide 6 mol modified triacrylate of glycerin (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., A-GLY-0606PE) and EO9 mol PO 9 mol modified triacrylate of glycerin (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., A) -GLY-0909PE) and the like can be mentioned.
  • Examples of the above-mentioned compound include 4-EO-modified tetraacrylate of pentaerythritol (SR-494, manufactured by Sartmer Japan Co., Ltd.) and 35EO-modified tetraacrylate of pentaerythritol (NK ester ATM-35E, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.). Can be done.
  • SR-494 4-EO-modified tetraacrylate of pentaerythritol
  • NK ester ATM-35E manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
  • 1,6-hexanediol di (meth) acrylate 1,4-cyclohexanediol di (meth) acrylate, 2-di (p-hydroxyphenyl) propandi (meth) acrylate, 2,2-bis [(4-4-bis).
  • cationically polymerizable compound examples include episulfide compounds, oxetane compounds, vinyl ether compounds, epoxy compounds, styrene compounds and diene compounds.
  • the episulfide compound any known compound can be used without particular limitation, and a polyfunctional compound having two or more episulfide groups in one molecule is preferable.
  • the polyfunctional episulfide compound include 2,2-bis (4- (2,3-epiopropoxy) phenyl) propane, bis (4- (2,3-epiopropoxy) phenyl) methane, and bis (3).
  • oxetane compound a known compound having an oxetane group can be used without particular limitation.
  • examples of the oxetane compound include a compound having a monofunctional oxetane group, a compound having a bifunctional oxetane group, and a compound having a trifunctional or higher oxetane group.
  • Examples of the compound having a monofunctional oxetane group include (3-ethyloxetane-3-yl) methyl acrylate, (3-ethyloxetane-3-yl) methylmethacrylate, and 3-ethyl-3-hydroxymethyloxetane, 3. -Ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- (phenoxymethyl) oxetane, 3-ethyl-3- (2-methacryloxymethyl) oxetane and 3-ethyl-3- ⁇ [[ 3- (Triethoxysilyl) propoxy] methyl ⁇ oxetane and the like can be mentioned.
  • Compounds having a bifunctional oxetane group include 4,4'-bis [(3-ethyl-3-oxetanyl) methoxymethyl] biphenyl and 1,4-bis [(3-ethyl-3-oxetanyl) methoxymethyl] benzene.
  • Compounds having a trifunctional or higher oxetane group include pentaerythritol tris (3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis (3-ethyl-3-oxetanylmethyl) ether, and dipentaerythritol hexa (3-ethyl).
  • any known compound can be used without particular limitation, but a compound having 3 to 35 carbon atoms is preferable, and examples thereof include the following monofunctional or polyfunctional vinyl ethers.
  • the above-mentioned "monofunctional vinyl ether” means a vinyl ether compound having one vinyl group
  • "polyfunctional vinyl ether” means a vinyl ether compound having two or more vinyl groups.
  • Examples of the monofunctional vinyl ether include methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, n-butyl vinyl ether, t-butyl vinyl ether, 2-ethylhexyl vinyl ether, n-nonyl vinyl ether, lauryl vinyl ether, cyclohexyl vinyl ether, cyclohexylmethyl vinyl ether and 4-methyl.
  • polyfunctional vinyl ether examples include ethylene glycol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, polyethylene glycol divinyl ether, propylene glycol divinyl ether, butylene glycol divinyl ether, hexanediol divinyl ether, and bisphenol A alkylene oxide divinyl ether.
  • Divinyl ethers such as bisphenol F alkylene oxide divinyl ether; trimethylol ethane trivinyl ether, trimethylol propane trivinyl ether, ditrimethylol propane tetravinyl ether, glycerin trivinyl ether, pentaerythritol tetravinyl ether, dipentaerythritol pentavinyl ether, dipentaerythritol hexavinyl ether.
  • EO-added trimethylol propanetrivinyl ether PO-added trimethylol propanetrivinyl ether, EO-added ditrimethylol propanetetravinyl ether, PO-added ditrimethylolpropane tetravinyl ether, EO-added pentaerythritol tetravinyl ether, PO-added pentaerythritol tetravinyl ether, EO-added di Examples thereof include pentaerythritol hexavinyl ether and PO-added dipentaerythritol hexavinyl ether.
  • the epoxy compound a known compound having an epoxy group can be used without particular limitation.
  • the epoxy compound include phenol novolac type epoxy resin, cresol novolac type epoxy resin, trishydroxyphenylmethane type epoxy resin, dicyclopentadienephenol type epoxy resin, bisphenol-A type epoxy resin, bisphenol-F type epoxy resin, and biphenol.
  • examples thereof include a type epoxy resin, a bisphenol-A novolak type epoxy resin, a naphthalene skeleton-containing epoxy resin, an alicyclic epoxy resin, and a heterocyclic epoxy resin.
  • the sum of the contents of the photopolymerizable compound with respect to 100 parts by mass of the total solid content contained in the composition for a color conversion film is preferably 30 parts by mass or more, preferably 50 parts by mass or more. More preferably, it is more preferably 70 parts by mass or more. Further, the sum of the contents of the photopolymerizable compound with respect to 100 parts by mass of the total solid content contained in the composition for a color conversion film is preferably 95 parts by mass or less.
  • a compound having a crosslinkable group to which a protecting group desorbed by heat is bonded has a crosslinkable group to which a protective group is bonded, and the protective group is desorbed by heating to carry out polymerization crosslinking by the crosslinkable group.
  • Blocked isocyanate can be obtained by reacting isocyanate with a blocking agent.
  • the isocyanate include 1,6-hexane diisocyanate, 4,4'-diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, xylylene diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, and the like.
  • 4,4'-Diisocyanate hydroxide isophorone diisocyanate, 1,5-naphthalenedi isocyanate, 4,4'-diphenyldiisocyanate, 1,3-bis (isocyanatemethyl) cyclohexane, phenylene 1,4-diisocyanate, phenylene 2,6- Examples thereof include diisocyanate, 1,3,6-hexamethylene triisocyanate and hexamethylene diisocyanate.
  • the blocking agent examples include alcohols, phenols, ⁇ -force prolactams, oximes, active methylenes, mercaptans, amines, imides, acid amides, imidazoles, ureas, carbamates, and imines. And compounds such as sulfites.
  • blocked isocyanates include Duranate (registered trademark) SBN-70D, TPA-B80E, TPA-B80X, 17B-60PX, MF-B60X, E402-B80T, ME20-B80S, MF-K60X manufactured by Asahi Kasei Corporation. Examples include K6000.
  • the content of the compound with respect to 100 parts by mass of the total solid content contained in the composition for a color conversion film is preferably 8 parts by mass or more, and more preferably 10 parts by mass or more. , 13 parts by mass or more is more preferable. Further, the content of the compound with respect to 100 parts by mass of the total solid content contained in the composition for a color conversion film is preferably 30 parts by mass or less.
  • the composition for a color conversion film of the present disclosure may contain one or more photopolymerization initiators.
  • a photopolymerization initiator include a photoradical polymerization initiator and a photocationic polymerization initiator.
  • Photoradical polymerization initiator examples include quinones, aromatic ketones, acetophenones, acylphosphine oxides, benzoins, benzoin ethers, dialkyl ketals, thioxanthons, dialkylaminobenzoic acid esters, and oxime esters. Classes, acridines, hexaarylbiimidazoles, pyrazoline compounds, N-aryl amino acids and ester compounds thereof, halogen compounds and the like.
  • quinones examples include 2-ethylanthraquinone, octaethylanthraquinone, 1,2-benzanthraquinone, 2,3-benzanthraquinone, 2-phenylanthraquinone, 2,3-diphenylanthraquinone, 1-chloroanthraquinone and 2-chloro.
  • aromatic ketones examples include compounds such as benzophenone, Michler's ketone [4,4'-bis (dimethylamino) benzophenone], 4,4'-bis (diethylamino) benzophenone and 4-methoxy-4'-dimethylaminobenzophenone. Can be mentioned.
  • acetophenones examples include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1-one, 1- (4). -Dodecylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, 2-benzyl- Compounds such as 2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 and 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propanone-1 can be mentioned.
  • Examples of commercially available products include Irgacure (registered trademark) 907, Irgacure (registered trademark) 369 and Irgacure (registered trademark) 379 manufactured by BASF Japan Limited.
  • acylphosphine oxides examples include 2,4,6-trimethylbenzyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phosphine oxide and bis (2,6-dimethoxybenzoyl) -2. , 4,4-trimethyl-Pentylphosphonoxide and the like.
  • examples of commercially available products include Lucillin TPO manufactured by BASF Co., Ltd., Irga Cure (registered trademark) 819 manufactured by BASF Co., Ltd., and the like.
  • benzoins and benzoin ethers include compounds such as benzoin, benzoin ethyl ether, benzoin phenyl ether, methyl benzoin and ethyl benzoin.
  • dialkyl ketals examples include compounds such as benzyl dimethyl ketal and benzyl diethyl ketal.
  • thioxanthones examples include compounds such as 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone and 2-chlorthioxanthone.
  • dialkylaminobenzoic acid esters examples include compounds such as ethyl dimethylaminobenzoate, ethyl diethylaminobenzoate, ethyl-p-dimethylaminobenzoate and 2-ethylhexyl-4- (dimethylamino) benzoate.
  • oxime esters examples include compounds such as 1-phenyl-1,2-propanedione-2-O-benzoyloxime and 1-phenyl-1,2-propanedione-2- (O-ethoxycarbonyl) oxime. Can be mentioned.
  • examples of commercially available products include CGI-325 manufactured by BASF Japan Ltd., Irgacure (registered trademark) OXE01, and Irgacure (registered trademark) OXE02.
  • the photocationic polymerization initiator is not particularly limited, and conventionally known compounds can be used.
  • the cation moiety is aromatic sulfonium, aromatic iodonium, aromatic diazonium, aromatic ammonium, thioxanthonium, (2,4-cyclopentadiene-1-yl) [(1-1-yl).
  • Aromatic sulfonium salt, aromatic iodonium salt, aromatic diazonium salt, aromatic ammonium salt, thioxane examples thereof include tonium salts and (2,4-cyclopentadiene-1-yl) [(1-methylethyl) benzene] -iron salts.
  • the photocationic polymerization initiator one kind may be used alone, or two or more kinds may be mixed at an arbitrary ratio as required.
  • aromatic sulfonium salt examples include bis [4- (diphenylsulfonio) phenyl] sulfide bishexafluorophosphate, bis [4- (diphenylsulfonio) phenyl] sulfide bishexafluoroantimonate, and bis [4- (diphenyl).
  • aromatic iodonium salt (a2) examples include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis (pentafluorophenyl) borate, and bis (dodecylphenyl) iodonium hexafluorophosphate.
  • aromatic diazonium salt examples include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate and phenyldiazonium tetrakis (pentafluorophenyl) borate.
  • aromatic ammonium salt examples include 1-benzyl-2-cyanopyridinium hexafluorophosphate, 1-benzyl-2-cyanopyridinium hexafluoroantimonate, 1-benzyl-2-cyanopyridinium tetrafluoroborate and 1-benzyl-.
  • thioxanthonium salt for example, S-biphenyl2-isopropylthioxanthonium hexafluorophosphate or the like can be used.
  • photocationic polymerization initiator examples include CPI-100P, CPI-200K and CPI-101A (all manufactured by San-Apro Co., Ltd.), Cyracure photocuring initiator UVI-6990, Cyracure photocuring initiator UVI-6992 and Cyracure Hikari.
  • Curing initiator UVI-6976 (above, manufactured by Dow Chemical Japan Co., Ltd.), Adekaoptomer SP-150, Adekaoptomer SP-152, Adekaoptomer SP-170 and Adekaoptomer SP-172 (above, Asahi Denka) (Manufactured by Kogyo Co., Ltd.), CI-5102 and CI-2855 (all manufactured by Nippon Soda Co., Ltd.), Sun Aid SI-60L, Sun Aid SI-80L, Sun Aid SI-100L, Sun Aid SI-110L, Sun Aid SI-180L, Sun Aid SI -110, Sun Aid SI-145, Sun Aid SI-150, Sun Aid SI-160 and Sun Aid SI-180 (above, manufactured by Sanshin Chemical Industry Co., Ltd.), Esacure 1064 and Esacure 1187 (above, manufactured by Lamberti), Omnicat 432, Omnicat 440, Omnicat 445, Omnicat 550, Omnicat 650 and Omnicat BL-550 (manu
  • the content of the photopolymerization initiator in the composition for a color conversion film is preferably 0.001 part by mass to 10 parts by mass, preferably 0.01 part by mass with respect to 100 parts by mass of the solid content contained in the composition for a color conversion film. Up to 5 parts by mass is more preferable.
  • the composition for a color conversion film of the present disclosure may contain a surfactant.
  • the surfactant include the surfactants described in paragraph [0017] of Japanese Patent No. 4502784 and paragraphs [0060] to [0071] of JP-A-2009-237362.
  • a fluorine-based surfactant a nonionic surfactant or a silicone-based surfactant is preferable.
  • fluorine-based surfactants include, for example, Megafuck (registered trademark) F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143. , F-144, F-437, F-475, F-477, F-479, F-482, F-482, F-511, F-552, F-554, F-555-A, F-556 , F-557, F-558, F-559, F-560, F-561, F-565, F-563, F-568, F-575, F-780, EXP, MFS-330, MFS-578.
  • Megafuck registered trademark
  • Fluorent (registered trademark) 710FL, 710FM, 610FM, 601AD, 601ADH2, 602A, 215M, 245F, 251, 212M, 250, 209F, 222F, 208G, 710LA, 710FS, 730LM, 650AC. , 681 and 683 all manufactured by NEOS Co., Ltd. and the like.
  • the fluorine-based surfactant has a molecular structure having a functional group containing a fluorine atom, and when heat is applied, the portion of the functional group containing the fluorine atom is cut off and the fluorine atom volatilizes (meth).
  • Acrylic compounds can also be suitably used.
  • DIC Corporation's Megafuck (registered trademark) DS series The Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)
  • Megafuck® DS-21 Megafuck® DS-21.
  • the fluorine-based surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound. Further, as the fluorine-based surfactant, a block polymer can also be used.
  • the fluorine-based surfactant contains 2 or more (preferably 5 or more) a structural unit derived from a (meth) acrylate compound having a fluorine atom and an alkyleneoxy group (preferably ethyleneoxy group or propyleneoxy group).
  • a fluorine-containing polymer compound containing a structural unit derived from the (meth) acrylate compound having the substance can also be preferably used.
  • a fluorine-based surfactant a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in the side chain can also be used. Specific examples thereof include Megafuck (registered trademark) RS-101, RS-102, RS-718K and RS-72-K (all manufactured by DIC Corporation).
  • PFOA perfluorooctanoic acid
  • PFOS perfluorooctanesulfonic acid
  • Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, their ethoxylates and their propoxylates (eg, glycerol propoxylates, glycerol ethoxylates, etc.), polyoxyethylene lauryl ethers, polyoxyethylene stearyls. Examples thereof include ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, and sorbitan fatty acid ester.
  • Examples of commercially available products include Pluronic (registered trademark) L10, L31, L61, L62, 10R5, 17R2 and 25R2 (all manufactured by BASF Corporation), Tetronic (registered trademark) 304, 701, 704, 901, 904 and 150R1 (above, manufactured by BASF Co., Ltd.), Solspers 20000 (above, manufactured by Nippon Lubrizol Co., Ltd.), NCW-101, NCW-1001 and NCW-1002 (above, manufactured by Fujifilm Wako Junyaku Co., Ltd.), Pionin D- 6112, D-6112-W and D-6315 (above, manufactured by Takemoto Oil & Fat Co., Ltd.), Orfin (registered trademark) E1010, and Surfinol (registered trademark) 104, 400 and 440 (above, Nissin Chemical Industry Co., Ltd.) Made) and the like.
  • silicone-based surfactant examples include a linear polymer having a siloxane bond and a modified siloxane polymer in which an organic group is introduced into a side chain or a terminal.
  • silicone-based surfactant examples include DOWSIL (registered trademark) 8032 ADDITIVE, Torre Silicone DC3PA, Torre Silicone SH7PA, Torre Silicone DC11PA, Torre Silicone SH21PA, Torre Silicone SH28PA, Torre Silicone SH29PA, Torre Silicone SH30PA, Torre Silicone SH8400.
  • DOWSIL registered trademark 8032 ADDITIVE
  • Torre Silicone DC3PA Torre Silicone SH7PA
  • Torre Silicone DC11PA Torre Silicone SH21PA
  • Torre Silicone SH28PA Torre Silicone SH29PA
  • Torre Silicone SH30PA Torre Silicone SH8400.
  • the surfactant may be used alone or in combination of two or more.
  • the content of the surfactant is 0.01 part by mass to 3 parts by mass with respect to 100 parts by mass of the solid content contained in the composition for the color conversion film. It is preferable that 0.02 part by mass to 1 part by mass is more preferable, and 0.05 part by mass to 0.80 part by mass is further preferable.
  • the composition for a color conversion film may contain one or more binder resins other than the photopolymerizable compound.
  • the binder resin is not particularly limited, and is, for example, an epoxy resin, a silicone resin (including an organopolysiloxane cured product (crosslinked product) such as silicone rubber and silicone gel), a polyester resin, a (meth) acrylic resin, and vinyl. Examples thereof include resins, polyamide resins, polyimide resins, polycarbonate resins, cellulose resins, polyolefin resins, urea resins, melamine resins, phenol resins, polyvinyl alcohol resins, polyvinyl butyral resins and fluororesins.
  • the composition for a color conversion film may contain an additive other than the above-mentioned organic light emitting material, polymerization initiator and binder resin.
  • the additive include viscosity modifiers, antioxidants, heat stabilizers, plasticizers, leveling agents, antistatic agents, cross-linking agents, curing agents, silane coupling agents, inorganic particles, organic particles and the like. ..
  • the composition for a color conversion film may contain one kind or two or more kinds of organic solvents.
  • the type of the organic solvent is not particularly limited, and conventionally known ones can be used.
  • the amount of the organic solvent contained in the composition for a color conversion film is not particularly limited, but from the viewpoints of dispersibility of the organic light emitting material and the like, ease of coating the coating liquid on the support, and ease of drying.
  • the content of the organic solvent with respect to 100 parts by mass of the total solid content contained in the composition for a color conversion film is preferably 50 parts by mass to 500 parts by mass.
  • the color conversion film 10 of the present disclosure includes a support 20 and a color conversion layer 30.
  • the color conversion film of the present disclosure may include two or more color conversion layers.
  • the color conversion film of the present disclosure may be provided with a protective layer on the color conversion layer (not shown).
  • the support is not particularly limited, and a conventionally known support can be used.
  • the support include resin films, glass, ceramics, paper, metal plates, foils and the like.
  • the resin material contained in the resin film include polyester such as polyethylene terephthalate (PET), cellulose resin such as cellulose acetate, polyolefin resin such as polyethylene and polypropylene, polyamide resin, polyimide resin, polystyrene resin, polycarbonate resin, and vinyl resin. , Silicone resin, fluororesin, thermosetting resin, photopolymerizable resin and the like.
  • the resin film may be surface-treated, and for example, a resin film treated with a chemical mat may be used as a support. By using a resin film that has been subjected to a chemical matte treatment, the support can be imparted with a function as a light diffusion layer.
  • the resin film a polyester film is preferable, and a polyethylene terephthalate film is particularly preferable.
  • the polyester film is preferably a biaxially stretched film.
  • the thickness of the polyester film is preferably 20 ⁇ m to 250 ⁇ m.
  • Examples of commercially available polyester films include Lumirer (registered trademark) # 38-U48, Lumirer (registered trademark) # 50-U48, Lumirer (registered trademark) # 75-U48, and Lumirer (registered trademark) # 50-U40.
  • Lumirer registered trademark # 75-U40 (above, manufactured by Toray Co., Ltd.), Cosmoshine (registered trademark) A4100 (thickness 50 ⁇ m, 75 ⁇ m, 100 ⁇ m, 125 ⁇ m, 188 ⁇ m), Cosmoshine (registered trademark) A4300 (thickness 38 ⁇ m) , 50 ⁇ m, 75 ⁇ m, 100 ⁇ m, 125 ⁇ m, 188 ⁇ m, 250 ⁇ m) and Cosmo Shine (registered trademark) A8300 (thickness 100 ⁇ m) (all manufactured by Toyo Spinning Co., Ltd.) and the like.
  • the support may be manufactured by a conventionally known method, or a commercially available one may be used.
  • Examples of the resin film subjected to the above-mentioned chemical mat treatment include Chemical Mat 125PW manufactured by Kimoto Co., Ltd.
  • Examples of the chemical mat treatment include treating the surface of the film with a chemical to form an uneven structure.
  • the thickness of the support is not particularly limited, but is preferably 20 ⁇ m or more, and more preferably 30 ⁇ m or more, from the viewpoint of the strength of the color conversion film and the retention of the color conversion layer. Further, from the viewpoint of miniaturization of the backlight unit and the like, the thickness of the support is preferably 1000 ⁇ m or less.
  • the color conversion layer contains at least two kinds of organic light emitting materials that emit light longer than the excitation light due to the excitation light and have different peak wavelengths of light emission from each other.
  • the organic light emitting material is a first organic light emitting material exhibiting light emission observed in a region having a peak wavelength of 500 nm or more and less than 580 nm by excitation light having a wavelength of 400 nm or more and less than 500 nm, and an excitation having a wavelength of 400 nm or more and less than 500 nm.
  • a second organic light emitting material exhibiting light emission observed in a region having a peak wavelength of 580 nm or more and 750 nm or less by at least one of light and light emission of the first organic light emitting material is included. Since the organic light emitting material, the first organic light emitting material, and the second organic light emitting material have been described above, the description thereof will be omitted here.
  • the content of the organic light emitting material with respect to 100 parts by mass of the total solid content contained in the color conversion layer is preferably 0.005 part by mass to 1 part by mass, preferably 0.007 part by mass to It is more preferably 0.7 parts by mass, and even more preferably 0.01 parts by mass to 0.5 parts by mass.
  • the numerical range of the content is that of each layer.
  • the color conversion layer contains at least one of a polymer of a photopolymerizable compound and a polymer of a compound having a crosslinkable group to which a protective group desorbed by heat is bonded (hereinafter, also referred to as a specific polymer).
  • the photopolymerizable compound is a compound obtained by polymerizing the above-mentioned photopolymerizable compound
  • the specific polymer is a compound obtained by polymerizing a compound having a crosslinkable group to which the above-mentioned desorbing protective group is bonded. Then, the description is omitted.
  • the sum of the contents of the photopolymerized compound with respect to 100 parts by mass of the total solid content contained in the composition for a color conversion film is preferably 30 parts by mass or more, preferably 50 parts by mass or more. Is more preferable, and it is further preferable that the amount is 70 parts by mass or more.
  • the sum of the content of the photopolymerized compound with respect to 100 parts by mass of the total solid content contained in the composition for a color conversion film is preferably 95 parts by mass or less.
  • the content of the specific polymer with respect to 100 parts by mass of the total solid content contained in the composition for a color conversion film is preferably 8 parts by mass or more, and more preferably 10 parts by mass or more. It is preferably 13 parts by mass or more, and more preferably 13 parts by mass or more. Further, the content of the specific polymer with respect to 100 parts by mass of the total solid content contained in the composition for a color conversion film is preferably 30 parts by mass or less.
  • the color conversion layer may contain one or more photopolymerization initiators. Since the photopolymerization initiator has been described above, the description thereof is omitted here.
  • the content of the photopolymerization initiator in the color conversion layer is preferably 0.001 part by mass to 10 parts by mass, and 0.01 part by mass to 5 parts by mass with respect to 100 parts by mass of the solid content contained in the composition for a color conversion film.
  • the unit is more preferable.
  • the numerical range of the content is that of each layer.
  • the color conversion layer may contain the above binder resin, additives and the like.
  • the thickness of the color conversion layer is preferably 1 ⁇ m or more, more preferably 5 ⁇ m or more, and further preferably 10 ⁇ m or more. Further, from the viewpoint of miniaturization of the backlight unit and the like, the thickness of the first color conversion layer is preferably 50 ⁇ m or less. When the color conversion layer has a multi-layer structure, the numerical range of the thickness is for each layer.
  • the color conversion film may have a protective layer on the color conversion layer.
  • the thickness of the protective layer is preferably 20 ⁇ m or more, more preferably 30 ⁇ m or more, from the viewpoint of the strength of the color conversion film. Further, from the viewpoint of miniaturization of the backlight unit and the like, the thickness of the protective layer is preferably 1000 ⁇ m or less.
  • the color conversion film may form other layers on the support, the color conversion layer or the protective layer.
  • examples of other layers include an oxygen barrier layer, a water vapor barrier layer, an antireflection layer, an antistatic layer, and an antifouling layer.
  • the method for producing a color conversion film of the present disclosure at least two kinds of organic light emitting materials, which emit light longer than the excitation light by the excitation light and whose emission peak wavelengths are different from each other, are photopolymerized on the support. It comprises forming a color conversion layer by curing a composition for a color conversion film containing at least one of a sex compound and a compound having a crosslinkable group to which a protective group desorbed by heat is bonded.
  • the composition for a color conversion film the above-mentioned composition can be used, and the details thereof will be omitted here.
  • the formation of the color conversion layer is performed by curing the composition for a color conversion film on the support.
  • Curing of the composition for a color conversion film can be performed, for example, by applying the composition for a color conversion film on a support, drying it, and then irradiating it with an active ray such as an ultraviolet ray or an electron beam.
  • the method for applying the composition for a color conversion film is not particularly limited, and a conventionally known method can be used.
  • the coating method include a curtain coating method, a dip coating method, a spin coating method, a printing coating method, a spray coating method, a slot coating method, a roll coating method, a slide coating method, a blade coating method, a gravure coating method and a wire bar method. And so on.
  • the drying method is not particularly limited, and can be performed by a conventionally known method such as using warm air.
  • the drying temperature is preferably changed as appropriate according to the composition of the coating liquid for forming the first color conversion layer, but is preferably 50 ° C to 200 ° C, preferably 70 ° C to 150 ° C.
  • the light source for light irradiation a conventionally known light source can be used, and for example, an air-cooled metal halide lamp can be used.
  • the output density is not particularly limited, but is preferably 30 W / cm to 100 W / cm.
  • the irradiation amount is not particularly limited, but is preferably 300 mJ / cm 2 to 2000 mJ / cm 2 .
  • the method for producing a color conversion film may include forming a protective layer on the color conversion layer.
  • the protective layer can be formed by heating and pressure-bonding the resin film or the like onto the color conversion layer.
  • the protective layer can be formed by applying a coating liquid containing a resin material on the color conversion layer and drying it.
  • another layer may be formed on a layer such as a color conversion layer. Since the specific examples of the other layers have been described above, the description thereof will be omitted here.
  • the backlight unit of the present disclosure includes a light source and the above-mentioned color conversion film. It is preferable that the surface on which the support is provided is arranged so as to face the light source side.
  • FIG. 2 is a schematic configuration sectional view showing an embodiment of the backlight unit, and the backlight unit will be described below with reference to FIG. 2.
  • the backlight unit 2 guides the light source 1A that emits excitation light (blue light LB ) having a wavelength of 400 nm or more and less than 500 nm and the excitation light emitted from the light source 1A to guide and emit.
  • a planar light source 1C provided with a light plate 1B, a color conversion film 1D provided on the planar light source 1C, and a retroreflective member 2B arranged to face the planar light source 1C with the color conversion film 1D interposed therebetween.
  • a reflector 2A arranged to face the color conversion film 1D with the planar light source 1C interposed therebetween is provided.
  • the two types of organic light emitting materials contained in the color conversion layer are observed in the region where the peak wavelength is 500 nm or more and less than 580 nm (green light LG ) and the peak, respectively. It emits light (red light LR ) observed in the region where the wavelength is 580 nm or more and 750 nm or less. Excitation light that has passed through the color conversion film (blue light LB ), light that is observed in the region where the peak wavelength is 500 nm or more and less than 580 nm (green light LG ), and light that is observed in the region where the peak wavelength is 580 nm or more and 750 nm or less.
  • White light L W is emitted from the surface of the retroreflective member 2B by the light (red light LR).
  • the blue light LB, the green light LG , and the red light LR emitted from the color conversion film 1D are incident on the retroreflective member 2B, and the incident light is reflected by the retroreflective member 2B. It repeatedly reflects off the plate 2A and passes through the color conversion film 1D a plurality of times. As a result, in the color conversion film 1D, a sufficient amount of excitation light (blue light LB) is absorbed by the specific organic light emitting material B that emits red light LR and the organic light emitting material that emits green light LG , which is necessary. Amount of fluorescence (green light LG and red light LR ) is emitted, and white light RW is emitted from the retroreflective member 2B as the sum of blue light LB , green light LG and red light LR .
  • the half-value range of each emission intensity of blue light, green light, and red light emitted by the backlight unit is preferably 80 nm or less, and preferably 50 nm or less. It is more preferably 40 nm or less, still more preferably 30 nm or less. Further, it is particularly preferable that the half width of the emission intensity of blue light is 25 nm or less.
  • the light source 1A a light emitting diode, a laser light source, or the like can be used.
  • the planar light source 1C may be a light source (edge light type light source) including a light source 1A and a light guide plate 1B that guides and emits primary light emitted from the light source 1A.
  • the light source 1A may be arranged side by side in a plane parallel to the color conversion film 1D, and may be a light source (direct type light source) provided with a diffuser plate instead of the light guide plate 1B.
  • a direct type light source may be used as the light guide plate.
  • the light guide plate a known one can be used without any limitation. In this embodiment, the case where a planar light source is used as the light source has been described as an example, but a light source other than the planar light source can also be used as the light source.
  • the reflector is not particularly limited, and a known one can be used.
  • the reflectors described in Japanese Patent Nos. 34166302, 3363565, 4091978, and 34486626 can be used. The contents of these publications are incorporated herein by reference.
  • the retroreflective member is composed of a known diffusion plate, diffusion sheet, prism sheet (for example, BEF series manufactured by Sumitomo 3M Ltd.) or reflective polarizing film (for example, DBEF series manufactured by Sumitomo 3M Ltd.) or the like. You may.
  • the configuration of the retroreflective member is described in the respective publications such as Japanese Patent No. 3416302, Japanese Patent No. 3363565, Japanese Patent No. 4091978 and Japanese Patent No. 34486626, and the contents of these publications are referred to in the present specification. Incorporated by.
  • the liquid crystal display device of the present disclosure includes the backlight unit and a liquid crystal cell unit.
  • FIG. 3 shows a schematic configuration sectional view showing an embodiment of the liquid crystal display device of the present disclosure.
  • the liquid crystal display device 4 includes a backlight unit 2 shown in FIG. 2 and a liquid crystal cell unit 3 arranged to face the retroreflective member 2B side of the backlight unit 2.
  • the liquid crystal cell unit 3 has a configuration in which the liquid crystal cell 31 is sandwiched between the polarizing plate 32 and the polarizing plate 33.
  • the polarizing plate 32 and the polarizing plate 33 have a configuration in which both main surfaces of the polarizing element 322 and the polarizing element 332 are protected by the polarizing plate protective films 321, 323, 331, and 333, respectively.
  • the liquid crystal cell and the polarizing plate constituting the liquid crystal display device are not particularly limited, and those manufactured by a known method or commercially available products can be used. Further, a known intermediate layer such as an adhesive layer may be provided between the layers.
  • the drive mode of the liquid crystal cell is not particularly limited, and is twisted nematic (TN), super twisted nematic (STN), vertical alignment (VA), imprint switching (IPS) or optical compensate bend cell (OCB).
  • TN twisted nematic
  • STN super twisted nematic
  • VA vertical alignment
  • IPS imprint switching
  • OBC optical compensate bend cell
  • Various modes such as, etc. can be used.
  • the configuration of the liquid crystal display device in the VA mode the configuration shown in FIG. 2 of Japanese Patent Application Laid-Open No. 2008-262161 can be mentioned as an example.
  • the specific configuration of the liquid crystal display device is not particularly limited, and a known configuration can be adopted.
  • the liquid crystal display device may include a functional layer such as an optical compensation member or an adhesive layer that performs optical compensation. Further, the liquid crystal display device may include a color filter substrate, a thin layer transistor substrate, a lens film, a diffusion sheet, a hard coat layer, an antireflection layer, a low reflection layer, an antiglare layer and the like. Further, the liquid crystal display device may include a backscattering layer, a primer layer, an antistatic layer, an undercoat layer, and the like.
  • the polarizing plate on the backlight unit side may be provided with a retardation film as a polarizing plate protective film on the liquid crystal cell side.
  • a retardation film a known retardation film such as a cellulose acylate film can be used.
  • -Radical polymerizable compound a Tricyclodecanedimethanol diacrylate, manufactured by Shin Nakamura Chemical Industry Co., Ltd., A-DCP -Radical polymerizable compound b: Dipentaerythritol polyacrylate, manufactured by Shin Nakamura Chemical Industry Co., Ltd., A-DPH -Radical polymerizable compound c: 1,9-nonanediol diacrylate, manufactured by Shin Nakamura Chemical Industry Co., Ltd., A-NOD-N Cationic polymerizable compound: 1,4-bis ⁇ [(3-ethyl-3-oxetanyl) methoxy] methyl ⁇ benzene, di [1-ethyl (3-oxetanyl)] methyl ether, manufactured by Toagosei Co., Ltd., Aron oxetane (Registered trademark) OXT-221 -Blocked isocyanate: manufactured by As
  • the composition for a color conversion film prepared as described above was applied onto glass, and then the solvent was volatilized to obtain a solid composition.
  • the spectrum of light emission exhibited by irradiating the solid composition with excitation light having a wavelength of 460 nm was obtained using a spectral fluorometer (F-2500 type spectrofluorometer manufactured by Hitachi, Ltd.).
  • peak wavelengths were confirmed in each of the region of 500 nm or more and less than 580 nm and the region of 580 nm or more and 750 nm or less.
  • Example 1 As a support, a polyethylene terephthalate (PET) film (thickness 50 ⁇ m, manufactured by Toray Industries, Inc., Lumirror (registered trademark) U48) was prepared.
  • the composition A-1 for a color conversion film was applied to one surface of the PET film using a slot die coater, and dried at 100 ° C. for 2 minutes. After drying, it was cured by irradiating it with ultraviolet rays using an air-cooled metal halide lamp (manufactured by Eye Graphics Co., Ltd.) under a nitrogen purge environment, and a color conversion layer having a thickness of 10 ⁇ m after drying was formed on the support. .. In the ultraviolet irradiation, the irradiation amount was set to 500 mJ / cm 2 .
  • a chemical mat-treated film manufactured by Kimoto Co., Ltd., chemical mat 125PW having a thickness of 138 ⁇ m was heated and pressure-bonded onto the color conversion layer as a protective layer to produce a color conversion film.
  • Example 2 to 5 and Comparative Examples 1 to 2 A color conversion film composition was produced in the same manner as in Example 1 except that the color conversion film composition A-1 was changed to the color conversion film composition shown in Table 24.
  • Example 5 and Comparative Example 2 the above-mentioned composition for a color conversion film was dried at 130 ° C. for 5 minutes, and was not irradiated with ultraviolet rays. Further, in Comparative Example 1, no ultraviolet irradiation was performed.
  • the color conversion film obtained in Example 1 was placed on a planar light emitting device equipped with a blue LED element having a emission peak wavelength of 447 nm so that the support surface was in contact with the support surface, and a prism sheet was placed on the color conversion film.
  • a current of 30 mA was passed through the planar light emitting device, the blue LED element was turned on, and light having a peak emission wavelength of 447 nm was irradiated from the support side, white light including blue light, green light and red light was observed.
  • An emission spectrum of the above white light was obtained using a spectroscopic emission luminance meter (CS-1000, manufactured by Konica Minolta Co., Ltd.).
  • the peak wavelength of green light was 500 nm or more and less than 580 nm.
  • the peak wavelength of red light was 580 nm or more and 750 nm or less.
  • the peak wavelength of the other examples was measured, it was confirmed that the peak wavelength of green light was 500 nm or more and less than 580 nm, and the peak wavelength of red light was 580 nm or more and 750 nm or less.
  • a cut-out color conversion film was placed on the blue light source, and the color conversion film was continuously irradiated with blue light having a wavelength of 447 nm.
  • the brightness of the light was measured every 10 hours in the same manner as described above, and the time for which the brightness decreased by 2% (hereinafter referred to as the brightness decrease time) was determined and evaluated based on the following evaluation criteria.
  • the evaluation results are shown in Table 24.
  • C The brightness reduction time was less than 30 hours.
  • composition for a color conversion film of the present disclosure can produce a color conversion film having excellent storage stability and excellent light resistance.

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PCT/JP2021/039169 2020-12-18 2021-10-22 色変換フィルム用組成物、色変換フィルム、色変換フィルムの製造方法、バックライトユニット及び液晶表示装置 Ceased WO2022130786A1 (ja)

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