WO2018110529A1 - Composition de matériau d'encapsulation pour élément d'affichage, et élément d'affichage mettant en œuvre celui-ci - Google Patents

Composition de matériau d'encapsulation pour élément d'affichage, et élément d'affichage mettant en œuvre celui-ci Download PDF

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WO2018110529A1
WO2018110529A1 PCT/JP2017/044504 JP2017044504W WO2018110529A1 WO 2018110529 A1 WO2018110529 A1 WO 2018110529A1 JP 2017044504 W JP2017044504 W JP 2017044504W WO 2018110529 A1 WO2018110529 A1 WO 2018110529A1
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oco
carbon atoms
general formula
coo
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PCT/JP2017/044504
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Japanese (ja)
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浩一 延藤
桑名　康弘
伊佐 西山
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Dic株式会社
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Priority to JP2018556675A priority Critical patent/JP6551618B2/ja
Publication of WO2018110529A1 publication Critical patent/WO2018110529A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • 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
    • G02F1/1339—Gaskets; Spacers; Sealing of cells
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H05B33/04—Sealing arrangements, e.g. against humidity
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • C09K19/38—Polymers
    • 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
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/87—Passivation; Containers; Encapsulations
    • H10K59/873—Encapsulations

Definitions

  • the present invention relates to a sealing material composition for a display element containing a filler and a polymerizable liquid crystal compound, which is used as a sealing agent for liquid crystal display elements, organic light emitting display elements, and the like, and a sealing agent and a base material using the composition
  • the present invention relates to a sealing protective agent, a liquid crystal display element, and an organic light emitting display element.
  • a display element such as a liquid crystal display element or an organic light emitting display element
  • Organic light-emitting substances such as liquid crystal materials, organic light-emitting diodes, and quantum dots used in these display elements are easily affected by moisture and oxygen, and glass sheets and metal sheets are used to ensure stable operation over a long period of time. It has been used as a sealing material.
  • the sealing material cannot cope with weight reduction and flexibility, and sealing materials using various polymer materials are being studied.
  • the problem to be solved by the present invention is to provide a sealing material composition for a display element having high gas barrier property and water vapor barrier property, and at the same time, a sealing agent for display element and substrate sealing using the composition It is providing the liquid crystal display element using the protective agent, the said sealing agent, and / or base-material sealing protective agent, an organic light emitting display element, and a quantum dot display element.
  • the present invention has been conducted by paying attention to using a polymerizable liquid crystal compound and a filler, and as a result, has come to provide the present invention.
  • this invention provides the sealing material composition for display elements containing at least 1 or more types of fillers and 1 type, or 2 or more types of polymerizable liquid crystal compounds. Moreover, the sealing agent using the composition of this invention, a base-material sealing protective agent, and the display element using the said sealing agent and / or base-material sealing protective agent are also provided.
  • a sealing protective layer having high gas barrier properties and water vapor barrier properties can be formed. is there.
  • the “liquid crystal” of the polymerizable liquid crystal compound is a compound of only one kind of the polymerizable liquid crystal compound to be used. It is intended to exhibit liquid crystallinity when it is intended to show or when mixed with other liquid crystal compounds to form a mixture.
  • the sealing material composition for display elements can be polymerized (formed into a film) by performing a polymerization treatment by irradiation with light such as ultraviolet rays, heating, or a combination thereof.
  • the sealing material composition for display elements of the present invention is characterized by containing at least one filler. By using a filler together with one or more polymerizable liquid crystal compounds, the sealing composition for a display element of the present invention can have high gas barrier properties and high water vapor barrier properties.
  • an organic filler or an inorganic filler can be used according to the shape to be used.
  • the shape of the inorganic filler is preferably a powdery filler.
  • the maximum particle size of the powdery filler used in the present invention is preferably 0.01 ⁇ m or more and 50 ⁇ m or less, more preferably 0.01 ⁇ m or more and 40 ⁇ m or less, further preferably 0.01 ⁇ m or more and 35 ⁇ m or less, and 0.01 ⁇ m or more and 30 ⁇ m or less. Is particularly preferred.
  • the average particle diameter is preferably 0.002 ⁇ m or more and 20 ⁇ m or less, more preferably 0.002 ⁇ m or more and 15 ⁇ m or less, further preferably 0.002 ⁇ m or more and 12 ⁇ m or less, and particularly preferably 0.002 ⁇ m or more and 10 ⁇ m or less.
  • the average particle diameter is less than 0.002 ⁇ m or exceeds 50 ⁇ m, it does not have a great influence on the improvement of the gas barrier performance and the water vapor barrier performance, so it is preferable to use a powdery filler in the above range.
  • examples of the powdery filler include lamellar plate-like or scale-like, spherical or indeterminate, rod-like needle-like or fiber-like. These may be used alone or in combination of two or more. Since the shape of the filler is excellent in gas barrier properties and high water vapor barrier properties, a layered inorganic filler, a spherical or amorphous filler, or a rod-like organic filler is preferably used.
  • the total content of the filler in the display element sealing material composition is 3 parts by mass to 40 parts by mass with respect to 100 parts by mass of the total content of the polymerizable liquid crystal compound used in the display element sealing material composition. It is preferably 3 to 30 parts by mass, more preferably 3 to 25 parts by mass.
  • the plate-like or scale-like fillers forming the layer form include talc, graphite, plate-like calcium carbonate, plate-like alumina, and silicates such as bentonite group clay minerals, smectite group clay minerals and mica group clay minerals. At least one selected can be preferably used.
  • the clay mineral include synthetic smectite, hectorite, beidellite, saponite, montmorillonite, vermiculite, stevensite, mica, synthetic mica, sodium tetrasilicon mica, and the like.
  • the clay mineral may be a modified clay mineral modified with a silylating agent so as to have a water vapor barrier property.
  • a known silylating agent such as methyltrimethoxysilane can be used as the silylating agent, but the silylating agent used is preferably 30% by weight or less based on the total amount of clay and silylating agent.
  • the average thickness of the layered filler is preferably less than 0.5 ⁇ m, more preferably less than 0.2 ⁇ m, still more preferably less than 0.1 ⁇ m, and particularly preferably less than 0.05 ⁇ m.
  • the average particle diameter (particle width) of the layered filler is preferably 0.01 ⁇ m or more and 10 ⁇ m or less, more preferably 0.02 ⁇ m or more and 5 ⁇ m or less, and still more preferably, as observed by an electron microscope.
  • the aspect ratio of the layered filler is in the range of 100 to 2500, more preferably in the range of 200 to 2000, and still more preferably in the range of 250 to 1500, particularly when the particle diameter is microscopically observed.
  • the range of 300 to 1000 is preferable.
  • the layered filler is preferably used in an amount of 3 to 40 parts by weight, preferably 3 to 30 parts by weight, based on 100 parts by weight of the total content of the polymerizable liquid crystal compounds used in the sealing material composition for display elements. More preferably, 3 parts by mass to 25 parts by mass is used.
  • Spherical or amorphous shapes include calcium carbonate, powdered silica, powdered metal powder, alumina, boehmite, hydrotalcite, magnesium hydroxide, magnesium oxide, zinc oxide, aluminum silicate, calcium silicate, aluminum hydroxide, carbon black , Titanium oxide, barium titanate and the like.
  • aluminum silicate, alumina, powder silica, and zinc oxide are preferably used from the viewpoints of transparency and gas barrier properties, and alumina and powder silica are more preferably used.
  • the average particle size of the fine powder filler is such that the primary particle size by electron microscope observation is preferably 0.5 ⁇ m or more and 30 ⁇ m or less, more preferably 0.5 ⁇ m or more and 20 ⁇ m or less, and further preferably 0.5 ⁇ m or more. It is 15 ⁇ m or less, and particularly preferably 0.5 ⁇ m or more and 10 ⁇ m or less.
  • the powder filler is used in an amount of 5 to 35 parts by mass with respect to 100 parts by mass of the total content of the polymerizable liquid crystal compound used in the sealing material composition for display elements. It is preferable to use 8 to 35 parts by mass, and it is particularly preferable to use 10 to 30 parts by mass.
  • the needle-like or fibrous fillers that form fine rods, glass fiber, carbon fiber (carbon nanofiller), boron fiber, zonolite, wollastonite, apatalite, calcium carbonate whisker, aluminum borate whisker as inorganic materials Zinc oxide whisker, potassium titanate whisker and the like, and examples of the organic material include aramid fiber and liquid crystal polyester fiber.
  • wollastonite and zinc oxide whiskers are preferably used from the viewpoint of impact strength, heat resistance, and gas barrier properties, and wollastonite is more preferably used.
  • the average particle diameter of the rod-shaped filler is preferably 1 ⁇ m or more and 30 ⁇ m or less, more preferably 1 ⁇ m or more and 20 ⁇ m or less, and more preferably 1 ⁇ m or more and 20 ⁇ m or less. Preferably they are 1 micrometer or more and 15 micrometers or less, Most preferably, they are 1 micrometer or more and 10 micrometers or less.
  • the average particle diameter by electron microscope observation is preferably 1 ⁇ m or more and 20 ⁇ m or less, more preferably 1 ⁇ m or more and 15 ⁇ m or less, further preferably 1 ⁇ m or more and 12 ⁇ m or less, and particularly preferably 1 ⁇ m or more and 10 ⁇ m or less. It is.
  • the rod-shaped filler is preferably used in an amount of 5 to 30 parts by mass, preferably 5 to 25 parts by mass, with respect to 100 parts by mass of the total content of the polymerizable liquid crystal compounds used in the display element sealing material composition. More preferably, 10 to 20 parts by mass is used.
  • the polymerizable liquid crystal compound used in the present invention is not particularly limited as long as it is a compound that exhibits liquid crystallinity alone or in a composition with another compound and has at least one polymerizable functional group. Conventional ones can be used.
  • a rod-like polymerizable liquid crystal compound having a polymerizable functional group such as a vinyl group, an acrylic group or a (meth) acryl group, or a maleimide as described in JP-A Nos. 2004-2373 and 2004-99446
  • a rod-like polymerizable liquid crystal compound having a group examples thereof include a rod-like polymerizable liquid crystal compound having a group.
  • a rod-like liquid crystal compound having a polymerizable group is preferable because it can easily produce a liquid crystal having a temperature range around room temperature.
  • the polymerizable liquid crystal compound is preferably a compound represented by the following general formula (II).
  • P 21 represents a polymerizable functional group
  • Sp 21 represents an alkylene group having 1 to 18 carbon atoms (the hydrogen atom in the alkylene group is a group having one or more halogen atoms, a CN group, or a polymerizable functional group). may be substituted, each of the one CH 2 group or nonadjacent two or more CH 2 groups existing in the alkylene group independently of one another by, -O -, - COO -, - OCO Or may be replaced by-or -OCO-O-).
  • X 21 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S.
  • one —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —CO—, —COO—. , —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH ⁇ CH—COO—, —CH ⁇ CH— OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —CH ⁇ CH—, —CF ⁇ CF— or —C ⁇ C— may be substituted, or R 21 may have the general formula (II-a)
  • P 22 represents a polymerizable functional group
  • Sp 22 represents the same as defined in Sp 21
  • X 22 represents that defined in X 21.
  • P 22 -Sp 22 and Sp 22 -X 22 do not include —O—O—, —O—NH—, —S—S— and —O—S— groups).
  • Q22 represents 0 or 1.
  • the mesogenic group represented by the above MG has the general formula (II-b)
  • B1, B2 and B3 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2, 5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2, 6-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3,4 Tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group, 9,10-d
  • P 23 represents a polymerizable functional group
  • Sp 23 represents the same as defined in Sp 21 above
  • X 23 represents —O—, —COO—, —OCO—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, or
  • a single bond is represented
  • q23 represents 0 or 1
  • q24 represents 0 or 1.
  • Z1 and Z2 are each independently —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH ⁇ CH—.
  • Sp 21 represents an alkylene group having 1 to 18 carbon atoms, and the hydrogen atom in the alkylene group may be substituted with a group having a polymerizable functional group.
  • examples of a group preferable as the group having a polymerizable functional group include a group represented by the general formula (II-c).
  • P 21 , P 22 and P 23 are each independently represented by the following formula (P-2-1): It preferably represents a substituent selected from a polymerizable group represented by the formula (P-2-20).
  • B1, B2 and B3 may each independently have the above-mentioned substituents, 1,4-phenylene group, 1,4-cyclohexylene group, 2,6 -Preferably represents a naphthylene group.
  • Sp 21 , Sp 22 and Sp 23 are each independently from the viewpoint of enhancing storage stability. preferably represents an 1-14 alkylene group, two or more CH 2 groups not one CH 2 group or adjacent existing in the alkylene group independently of one another each, -O -, - COO It may be replaced by-or -OCO-. Further, Sp 21 , Sp 22 and Sp 23 each independently preferably represent an alkylene group having 1 to 12 carbon atoms, and are not adjacent to one CH 2 group present in the alkylene group. Two or more CH 2 groups may be replaced by —O—.
  • X 21 , X 22, and X 23 are each independently —O—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —O—CO—O—, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO —CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, — It preferably represents OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH ⁇ CH—, —C ⁇ C— or a single bond, —O—, —COO—, —OCO
  • Z1 and Z2 are each independently —COO—, —OCO—, —CH 2 O—, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2. It preferably represents COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, —C ⁇ N—, —N ⁇ C—, or a single bond.
  • r1 preferably represents 0 or 1.
  • r1 preferably represents 0 or 1.
  • the compound represented by the following general formula (II-1) is preferable as the monofunctional polymerizable liquid crystal compound having one polymerizable functional group in the molecule.
  • R 211 represents a hydrogen atom, a halogen atom, a cyano group, one —CH 2 —, or two or more non-adjacent —CH 2 —, each independently —O—.
  • B11, B21 and B31 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran- 2,5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene- 2,6-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3 4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group,
  • the hydrogen atom in the alkyl group may be substituted with one or more phenyl groups, each of two or more CH 2 groups not one CH 2 group or adjacent present in this group Independently of each other, —O—, —COO—, —OCO Or may be replaced by —OCO—O—), an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, or the number of carbon atoms May have an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, and / or an alkenoyl group having 2 to 8 carbon atoms,
  • Z11 and Z21 are each independently —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH
  • P 211 is the above-described formula (P-2-1), (P-2-2), (P-2-7), (P— 2-12) and (P-2-13) are preferable, and formulas (P-2-1), (P-2-2), and (P-2-7) are more preferable.
  • Sp 211 is preferably each independently an alkylene group having 1 to 14 carbon atoms from the viewpoint of enhancing storage stability, and is present in the alkylene group.
  • Two CH 2 groups or two or more non-adjacent CH 2 groups may be each independently replaced by —O—, —COO— or —OCO—.
  • Sp 211 are each independently more preferably an alkylene group having 1 to 12 carbon atoms, not one CH 2 group or adjacent existing in the alkylene group two or more CH 2 The group may be replaced by -O-.
  • X 211 each independently represents —O—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —O—CO.
  • R 211 represents a hydrogen atom, a halogen atom, a cyano group, one —CH 2 —, or two or more non-adjacent —CH 2 —, each independently —O —, —CO—, —COO—, —OCO—, —O—CO—O—, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH
  • R 211 represents a hydrogen atom, a halogen atom, a cyano group, one —CH 2 —, or two or more non-adjacent —CH 2 —, each independently —O—, —CO—, —COO.
  • one or more hydrogen atoms of the alkyl group or alkenyl group may be substituted with a halogen atom or a cyano group, and when a plurality of substituents are substituted, they may be the same or different. Also good.
  • B11, B21 and B31 each independently may have the above-mentioned substituents such as 1,4-phenylene group, 1,4-cyclohexylene group, 2 , 6-naphthylene group, and Z11 and Z21 are each independently —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH ⁇ CH It is preferable to represent —, —C ⁇ C—, —C ⁇ N—, —N ⁇ C—, or a single bond, and r11 preferably represents 0 or 1.
  • Examples of the general formula (II-1) include compounds represented by the following general formulas (II-1-1) to (II-1-4), but are not limited to the following general formulas is not.
  • P 211 , Sp 211 , X 211 , and q 211 are the same as defined in the general formula (II-1).
  • B111, B112, B113, B21, and B31 are the same as the definitions of B11 to B31 in the general formula (II-1-b).
  • preferred groups also represent the same as defined for B11 to B31, and may be the same or different.
  • Z111, Z112, Z113, and Z21 represent the same definitions as Z11 to Z21 in the general formula (II-1-b).
  • R 211 represents a hydrogen atom, a halogen atom, a cyano group, one —CH 2 —, or two or more non-adjacent — CH 2 — is independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO.
  • the compounds represented by the general formulas (II-1-1) to (II-1-4) are represented by the following formulas (II-1-1-1) to (II-1-1-26).
  • the compounds represented are exemplified, but not limited thereto.
  • R c represents a hydrogen atom or a methyl group
  • m represents an integer of 0 to 18, n represents 0 or 1
  • R 211 represents the above general formulas (II-1-1) to (II- 1-4) is the same as defined above, except that R 211 represents a hydrogen atom, a halogen atom, a cyano group, one —CH 2 — is —O—, —CO—, —COO—, —OCO—, It preferably represents a linear alkyl group having 1 to 6 carbon atoms or a linear alkenyl group having 1 to 6 carbon atoms, which may be substituted by
  • the cyclic group includes one or more F, Cl, CF 3 , OCF 3 , CN groups, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and 1 to 8 alkanoyl groups, alkanoyloxy groups having 1 to 8 carbon atoms, alkoxycarbon
  • the compounds represented by the general formulas (II-1-1-1) to (II-1-1-26) are more specifically represented by the following general formulas (II-1-2-1) to The compound represented by (II-1-2-37) can be exemplified, but is not limited thereto.
  • the total content of the polymerizable liquid crystal compound is preferably 0 to 90% by mass, and preferably 0 to 85% by mass, based on the total amount of the polymerizable liquid crystal compound used in the sealing material composition for display elements. More preferably, the content is particularly preferably 0 to 80% by mass.
  • the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, and when emphasizing the hardness of the coating film, the upper limit Is preferably 80% by mass or less, and more preferably 70% by mass or less.
  • the compound represented by the following general formula (II-2) is preferable as the bifunctional polymerizable liquid crystal compound having two polymerizable functional groups in the molecule.
  • P 221 , X 211 , q 221 , X 222 , q 222 , and P 222 are P 21 , X 21 , q 21 , X 22 , q 22 in the general formula (II) or the general formula (II-a), respectively.
  • Sp 221 and Sp 222 each independently represent an alkylene group having 1 to 18 carbon atoms (the hydrogen atom in the alkylene group is one or more halogen atoms, or CN It may be substituted by a group, two or more of CH 2 groups, independently of one another each of the present in the radical is not one CH 2 group or adjacent, -O -, - COO -, - OCO -Or -OCO-O- may be substituted).
  • MG 2 represents a mesogenic group, and the mesogenic group includes the general formula (II-2-b)
  • B11, B21 and B31 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran- 2,5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene- 2,6-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3 4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group,
  • the hydrogen atom in the alkyl group may be substituted with one or more phenyl groups, each of two or more CH 2 groups not one CH 2 group or adjacent present in this group Independently of each other, —O—, —COO—, —OCO Or may be replaced by —OCO—O—), an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, or the number of carbon atoms May have an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, and / or an alkenoyl group having 2 to 8 carbon atoms,
  • Z11 and Z21 are each independently —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH
  • P 221 and P 222 are each independently from the above formulas (P-2-1), (P-2-2), (P— 2-7), (P-2-12), and (P-2-13) are preferable, and formulas (P-2-1) and (P-2-2) are more preferable.
  • Sp 221 and Sp 222 are preferably each independently an alkylene group having 1 to 14 carbon atoms from the viewpoint of enhancing storage stability.
  • One CH 2 group present or two or more non-adjacent CH 2 groups may each be independently replaced by —O—, —COO— or —OCO—.
  • each of Sp 221 and Sp 222 preferably independently represents an alkylene group having 1 to 12 carbon atoms, and one CH 2 group present in the alkylene group or two or more not adjacent to each other The CH 2 group may be replaced by —O—.
  • X 221 and X 222 each independently represent —O—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, — O—CO—O—, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO -CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 -OCO -, - COO-CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 - It preferably represents OCO—, —CH ⁇ CH—, —C ⁇ C— or a single bond, more preferably —O—, —COO—, —OCO— or a single bond (provided that P 221 —
  • B11, B21 and B31 each independently may have the above-described substituents such as 1,4-phenylene group, 1,4-cyclohexylene group, 2 , 6-naphthylene group, and Z11 and Z21 are each independently —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH ⁇ CH It is preferable to represent —, —C ⁇ C—, —C ⁇ N—, —N ⁇ C—, or a single bond, and r11 preferably represents 0 or 1.
  • Examples of the general formula (II-2) include compounds represented by the following general formulas (II-2-1) to (II-2-4), but are not limited to the following general formulas is not.
  • P 221 , Sp 221 , X 221 , q 221 , X 222 , Sp 222 , q 222 , and P 222 are respectively the above general formulas.
  • B111, B112, B113, B21, and B31 are the same as the definitions of B11 to B31 in the general formula (II-2-b).
  • Z111, Z112, Z113, and Z21 represent the same definitions as Z11 to Z21 in the general formula (II-2-b).
  • Preferred groups also represent the same definitions as Z11 to Z21, and may be the same or different.
  • the compounds represented by the general formulas (II-2-1) to (II-2-4) include the following general formulas (II-2-1-1) to (II-2-1-25): ) Is exemplified, but not limited thereto.
  • R d and R e each independently represent a hydrogen atom or a methyl group
  • the cyclic group includes one or more F, Cl, CF 3 , OCF 3 , CN groups, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and 1 to 8 alkanoyl groups, alkanoyloxy groups having 1 to 8 carbon atoms, alkoxycarbonyl groups having 1 to 8 carbon atoms, alkenyl groups having 2 to 8 carbon atoms, alkenyloxy groups having 2 to 8 carbon atoms, carbon atoms It may have an alkenoyl group having 2 to 8 carbon atoms and an alkenoyloxy group having 2 to 8 carbon atoms.
  • M1, m2, m3, and m4 each independently represent an integer of 0 to 8, and n1, n2, n3, and n4 each independently represent 0 or 1.
  • the compounds represented by the general formulas (II-2-1-1) to (II-2-1-21) are more specifically represented by the following general formulas (II-2-2-1) to The compound represented by (II-2-2-35) can be exemplified, but is not limited thereto.
  • the polymerizable liquid crystal compound having two polymerizable functional groups can be used singly or in combination of two or more, preferably 1 to 5 types, more preferably 2 to 5 types.
  • the total content of the conductive liquid crystal compound is preferably 10 to 100% by mass, more preferably 15 to 85% by mass, based on the total amount of the polymerizable liquid crystal compound used for the sealing material composition for display elements. A content of 20 to 80% by mass is particularly preferable.
  • the lower limit is preferably 30% by mass or more, more preferably 50% by mass or more, and when importance is attached to the orientation of the film, the upper limit is 85% by mass. % Or less, and more preferably 80% by mass or less.
  • the polyfunctional polymerizable liquid crystal compound having three or more polymerizable functional groups it is preferable to use a compound having three polymerizable functional groups.
  • the compounds represented by the general formula (II) the following general formulas (II-3-1) to (II) are used as polyfunctional polymerizable liquid crystal compounds having three or four polymerizable functional groups in the molecule. Illustrative are compounds represented by II-3-2).
  • P 231 , X 231 , q231, X 232 , q232, P 232 , P 233 , X 233 , q234, q233, X 234 , Q236, q235, P 234 , X 235 , q238, q237, and P 235 are P 21 , X 21 in the general formula (II), general formula (II-a), and general formula (II-c), respectively.
  • Sp 231 , Sp 232 , Sp 233 , Sp 234 and Sp 235 are each independently an alkylene having 1 to 18 carbon atoms.
  • a hydrogen atom in the alkylene group may be substituted by one or more halogen atoms or a CN group, one CH 2 group present in the group or two or more non-adjacent Each independently of the CH 2 group may be replaced by —O—, —COO—, —OCO— or —OCO—O—.
  • j3 represents 0 or 1
  • MG 3 represents a mesogenic group, and the mesogenic group includes the general formula (II-3-b)
  • B11, B21 and B31 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran- 2,5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene- 2,6-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3 4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group,
  • the hydrogen atom in the alkyl group may be substituted with one or more phenyl groups, each of two or more CH 2 groups not one CH 2 group or adjacent present in this group Independently of each other, —O—, —COO—, —OCO Or may be replaced by —OCO—O—), an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, or the number of carbon atoms May have an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, and / or an alkenoyl group having 2 to 8 carbon atoms,
  • Z11 and Z21 are each independently —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH
  • Sp 231 , Sp 232 , Sp 233 , Sp 234 and Sp 235 are each independently from the viewpoint of enhancing storage stability.
  • , preferably represents an alkylene group having 1 to 14 carbon atoms, and each of the two or more CH 2 groups not one CH 2 group or adjacent existing in the alkylene group independently of one another, -O It may be replaced by-, -COO- or -OCO-.
  • Sp 231 , Sp 232 , Sp 233 , Sp 234 and Sp 235 each independently preferably represent an alkylene group having 1 to 12 carbon atoms, and one CH 2 present in the alkylene group. A group or two or more non-adjacent CH 2 groups may be replaced by —O—.
  • B11, B21 and B31 each independently may have the above-described substituents such as 1,4-phenylene group, 1,4-cyclohexylene group, 2 , 6-naphthylene group, and Z11 and Z21 are each independently —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH ⁇ CH It is preferable to represent —, —C ⁇ C—, —C ⁇ N—, —N ⁇ C—, or a single bond, and r11 preferably represents 0 or 1.
  • Examples of the compounds represented by the above general formula (II-3-1) to general formula (II-3-2) include the following general formulas (II-3-3-1) to (II-3-3-1-10) ), But is not limited to the following general formula.
  • P 231 to P 235 , Sp 231 to Sp 235 , X 231 to X 235 , q231 to q238, and MG 3 are Each represents the same definition as in general formula (II-3-1) to general formula (II-3-2).
  • B111, B112, B113, B21, and B31 are respectively B11 of the general formula (II-3-b), It represents the same as the definition of B21 and B31, and preferred groups also represent the same as the definitions of B11 to B31, and may be the same or different.
  • Z111, Z112, Z113, and Z21 are the same as Z11 and Z21 in the general formula (II-3-b), respectively. It represents the same as the definition, and preferred groups also represent the same as the definitions of Z11 to Z21, and may be the same or different.
  • Examples of the compounds represented by the general formulas (II-3-3-1) to (II-3-3-10) include the following formulas (II-3-3-3-1) to (II-3): Although the compound represented by -3-3-3) is exemplified, the compound is not limited thereto.
  • R f , R g, and R h each independently represent a hydrogen atom or a methyl group
  • R i , R j, and R k are each independently a hydrogen atom, a halogen atom, or a carbon number of 1 to 6
  • m4 to m9 each independently represents an integer of 0 to 18, and n4 to n9 each independently represents 0 or 1.
  • the polyfunctional polymerizable liquid crystal compound having three or more polymerizable functional groups can be used alone or in combination of two or more.
  • the total content of the polyfunctional polymerizable liquid crystal compound having 3 or more polymerizable functional groups in the molecule is 0 to 80% by mass of the total amount of the polymerizable liquid crystal compound used in the sealing material composition for display elements.
  • the content is preferably 0 to 60% by mass, more preferably 0 to 40% by mass.
  • the lower limit is preferably 10% by mass or more, more preferably 20% by mass or more, and particularly preferably 30% by mass or more
  • the upper limit is preferably 50% by mass or less, more preferably 35% by mass or less, and particularly preferably 20% by mass or less.
  • the sealing material composition for display elements of the present invention it is preferable to use a mixture of a plurality of the polymerizable liquid crystal compounds.
  • the curability of the resulting film is improved. It is preferable to use at least one monofunctional polymerizable liquid crystal compound and at least one bifunctional polymerizable liquid crystal compound in combination.
  • the compound when it is desired to further improve curability when the sealing material composition for display elements of the present invention is used as a film, the compound has three or more ring structures as a bifunctional polymerizable liquid crystal compound.
  • a compound selected from (II-2-2) to (II-2-4) is preferably used as a mixture of polymerizable liquid crystal compounds.
  • the total amount of the monofunctional polymerizable liquid crystal compound and the bifunctional polymerizable liquid crystal compound is 70% by mass to 100% by mass of the total amount of the polymerizable liquid crystal compound used for the sealing material composition for display elements. It is particularly preferable that the content be 80% by mass to 100% by mass.
  • a compound containing a mesogenic group having no polymerizable group may be added to the sealing material composition for a display element of the present invention, and an ordinary liquid crystal device such as STN (Super Twisted Nematic) is used. Examples thereof include compounds used for liquid crystals, TN (twisted nematic) liquid crystals, TFT (thin film transistor) liquid crystals, and the like.
  • the compound containing a mesogenic group having no polymerizable functional group is preferably a compound represented by the following general formula (5).
  • the mesogenic group or mesogenic supporting group represented by MG3 has the general formula (5-b)
  • A1 d , A2 d and A3 d are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group Pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3,4-tetrahydronaphthalene-2 , 6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group, 9,10-d
  • -O -, - S may, independently each two or more CH 2 groups not one CH 2 group or adjacent present in this group to each other, in a manner that oxygen atoms are not directly bonded to each other, -O -, - S May be replaced by —, —NH—, —N (CH 3 ) —, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS— or —C ⁇ C—. . ).
  • Ra and Rb each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, or a cyano group.
  • an alkyl group of ⁇ 6 or an alkoxy group of 1 to 6 carbon atoms all may be unsubstituted or substituted by one or more halogen atoms.
  • the total content of the compound having a mesogen group is preferably 0 parts by mass or more and 20 parts by mass or less with respect to 100 parts by mass of the total content of the polymerizable liquid crystal compound used for the sealing material composition for display elements. In this case, it is preferably 1 part by mass or more, preferably 2 parts by mass or more, preferably 5 parts by mass or more, and preferably 15 parts by mass or less, and 10 parts by mass or less. Preferably there is. (Other ingredients) (Chiral compound)
  • the sealing material composition for display elements in the present invention contains a polymerizable chiral compound that may exhibit liquid crystallinity other than the polymerizable compound represented by the general formula (II) or may be non-liquid crystalline. You can also
  • the polymerizable chiral compound used in the present invention preferably has one or more polymerizable functional groups.
  • examples of such compounds include JP-A-11-193287, JP-A-2001-158788, JP-T 2006-52669, JP-A-2007-269639, JP-A-2007-269640, 2009.
  • -84178 which contains chiral saccharides such as isosorbide, isomannite, glucoside, etc., and a rigid group such as 1,4-phenylene group and 1,4-cyclohexylene group, and a vinyl group
  • a polymerizable chiral compound having a polymerizable functional group such as an acryloyl group, a (meth) acryloyl group, or a maleimide group, a polymerizable chiral compound comprising a terpenoid derivative as described in JP-A-8-239666, NATURE VOL35, pages 467-469 (November 30, 1995) Issue), NATURE VOL392, pages 476-479 (issued on April 2, 1998), or the like, or a polymerizable chiral compound comprising a mesogenic group and a spacer having a chiral moiety, or JP-T-2004-504285.
  • a polymerizable chiral compound containing a binaphthyl group as described in JP-A-2007-248945 is preferable for the sealing material composition for display elements of the present invention.
  • the compounding amount of the polymerizable chiral compound needs to be appropriately adjusted depending on the helical induction force of the compound, but it is preferably 0 to 25% by mass, preferably 0 to 20% by mass in the polymerizable liquid crystal composition. More preferably, the content is particularly preferably 0 to 15% by mass.
  • Examples of the general formula of the polymerizable chiral compound include general formulas (3-1) to (3-4), but are not limited to the following general formula.
  • Sp 3a and Sp 3b each independently represent an alkylene group having 0 to 18 carbon atoms, and the alkylene group is a carbon atom having one or more halogen atoms, a CN group, or a polymerizable functional group.
  • alkyl group having 1 to 8 may be substituted by an alkyl group having 1 to 8, two or more of CH 2 groups, independently of one another each of the present in the radical is not one CH 2 group or adjacent, each other oxygen atom -O-, -S-, -NH-, -N (CH 3 )-, -CO-, -COO-, -OCO-, -OCOO-, -SCO-, -COS- Or it may be replaced by -C ⁇ C- A1, A2, A3, A4 and A5 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, , 3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2
  • R 3a and R 3b are represented by the general formula (3-a)
  • P 3a represents a polymerizable functional group, and Sp 3a represents the same meaning as Sp 1 ).
  • P 3a preferably represents a substituent selected from the polymerizable groups represented by the following formulas (P-1) to (P-20).
  • the formula (P-1) or the formulas (P-2), (P-7), (P-12), and (P-13) are preferable from the viewpoint of increasing the polymerizability.
  • Formulas (P-1), (P-7), and (P-12) are more preferable.
  • polymerizable chiral compound examples include compounds represented by the following general formulas (3-5) to (3-26), but are not limited to the following compounds.
  • m, n, k, and l each independently represent an integer of 1 to 18, and R 1 to R 4 each independently represents a hydrogen atom, carbon An alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group, and a cyano group; When these groups are alkyl groups having 1 to 6 carbon atoms or alkoxy groups having 1 to 6 carbon atoms, all of them may be unsubstituted or substituted by one or more halogen atoms. .
  • a polymerizable discotic liquid crystal compound exhibiting liquid crystallinity can also be used as the polymerizable liquid crystal compound.
  • the sealing material composition for display elements of this invention can also contain a non-liquid crystalline polymerizable discotic compound.
  • the polymerizable discotic compound used in the present invention preferably has one or more polymerizable functional groups.
  • examples of such compounds include polymerizable compounds described in, for example, JP-A-7-281028, JP-A-7-287120, JP-A-7-333431, and JP-A-8-27284. Is mentioned.
  • Examples of the polymerizable discotic liquid crystal compound exhibiting liquid crystallinity as the polymerizable liquid crystal compound include compounds represented by the following general formula (III).
  • each R 7 independently represents a substituent represented by the general formula (III-a).
  • R 9 and R 10 each independently represent a hydrogen atom, a halogen atom or a methyl group
  • R 8 represents an alkoxy group having 1 to 20 carbon atoms
  • the hydrogen atom in the alkoxy group is generally May be substituted by a substituent represented by the formula (III-b), the general formula (III-c), or the general formula (III-d), and at least R 8 present in the general formula (III)
  • One is substituted by a substituent represented by general formula (III-b), general formula (III-c), or general formula (III-d).
  • R 81 , R 82 , R 83 , R 84 , R 85 , R 86 , R 87 , R 88 and R 89 are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 5 carbon atoms.
  • N1 represents 0 or 1
  • At least one of R 8 present in the general formula (III) is substituted with a substituent represented by the general formula (III-b), the general formula (III-c), or the general formula (III-d).
  • all R 8 present in the general formula (III) is independently represented by the general formula (III-b), the general formula (III-c), or the general formula (III-d). It is preferably substituted by the substituent represented.
  • the substituent represented by the general formula (III-a) is specifically preferably a substituent represented by the general formula (III-e).
  • n2 represents an integer of 1 to 18
  • Preferred examples of the compound represented by the general formula (III) include compounds represented by the following general formula (III-1) and general formula (III-2).
  • n an integer of 1 to 18
  • the polymerizable liquid crystal compound one or more polymerizable discotic liquid crystal compounds exhibiting liquid crystallinity can be used.
  • polymerizable liquid crystal compound only a polymerizable discotic liquid crystal compound can be used, or a polymerizable rod-like liquid crystal compound and a polymerizable discotic liquid crystal compound can be used in combination.
  • the total content of the polymerizable discotic liquid crystal compound exhibiting liquid crystallinity is the polymerizability used in the sealing material composition for display elements.
  • the total amount of the liquid crystal compound is preferably 5 to 95% by mass, more preferably 10 to 90% by mass, and particularly preferably 20 to 80% by mass.
  • Examples of general formulas of other polymerizable discotic compounds include general formulas (4-1) to (4-3), but are not limited to the following general formulas.
  • Sp 4 represents an alkylene group having 0 to 18 carbon atoms, and the alkylene group is substituted with one or more halogen atoms, CN group, or an alkyl group having 1 to 8 carbon atoms having a polymerizable functional group.
  • Z 4a represents —CO—, —CH 2 CH 2 —, —CH 2 O—, —CH ⁇ CH—, —CH ⁇ CHCOO—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, — COCH 2 CH 2 — represents an alkyl group which may have a halogen atom having 2 to 10 carbon atoms or a single bond
  • R 4 represents a hydrogen atom, a halogen atom, a cyano group, or an alkyl group having 1 to 18 carbon atoms, and the alkyl group may be substituted with one or more halogen atoms or CN.
  • One CH 2 group present or two or more non-adjacent CH 2 groups are each independently of each other in a form in which oxygen atoms are not directly bonded to each other, —O—, —S—, —NH—, May be replaced by —N (CH 3 ) —, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS— or —C ⁇ C—, Or R 4 represents the general formula (4-a)
  • P 4a represents a polymerizable functional group
  • Sp 3a represents the same meaning as Sp 1
  • P 4a preferably represents a substituent selected from the polymerizable groups represented by the following formulas (P-1) to (P-20).
  • the formula (P-1) or the formulas (P-2), (P-7), (P-12), and (P-13) are preferable from the viewpoint of increasing the polymerizability.
  • Formulas (P-1), (P-7), and (P-12) are more preferable.
  • polymerizable discotic compound examples include compounds (4-4) to (4-6), but are not limited to the following compounds.
  • n represents an integer of 1 to 18.
  • a compound having a polymerizable group but not a liquid crystal compound can be added.
  • Such a compound can be used without particular limitation as long as it is generally recognized as a polymerizable monomer or polymerizable oligomer in this technical field.
  • it is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and particularly preferably 15 parts by mass or less, with respect to 100 parts by mass of the total content of polymerizable compounds contained in the polymerizable composition. preferable.
  • organic solvent You may add an organic solvent to the sealing material composition for display elements in this invention.
  • the organic solvent in which a polymeric liquid crystal compound shows favorable solubility is preferable, and it is preferable that it is an organic solvent which can be dried at the temperature of 100 degrees C or less.
  • solvents examples include aromatic hydrocarbons such as toluene, xylene, cumene, and mesitylene, ester solvents such as methyl acetate, ethyl acetate, propyl acetate, and butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclohexane, and the like.
  • Ketone solvents such as pentanone, ether solvents such as tetrahydrofuran, 1,2-dimethoxyethane and anisole, amide solvents such as N, N-dimethylformamide and N-methyl-2-pyrrolidone, propylene glycol monomethyl ether acetate , Diethylene glycol monomethyl ether acetate, ⁇ -butyrolactone, chlorobenzene and the like.
  • amide solvents such as N, N-dimethylformamide and N-methyl-2-pyrrolidone
  • propylene glycol monomethyl ether acetate Diethylene glycol monomethyl ether acetate, ⁇ -butyrolactone, chlorobenzene and the like.
  • amide solvents such as N, N-dimethylformamide and N-methyl-2-pyrrolidone
  • propylene glycol monomethyl ether acetate Diethylene glycol monomethyl ether acetate, ⁇ -butyrolactone, chlorobenzene and the like.
  • the sealing material composition for display elements used in the present invention can be applied to the substrate as a solution using an organic solvent, and the ratio of the organic solvent used for the sealing material composition for display elements was applied.
  • the total amount of the organic solvent contained in the sealing material composition for display elements is preferably 0 to 90% by mass, and preferably 0 to 85% by mass. Is more preferable, and 0 to 80% by mass is particularly preferable.
  • the filler used in the present invention is dispersed in the organic solvent to obtain a dispersion, and then the dispersion A polymerizable liquid crystal compound or the like used in the present invention may be dissolved therein to form a composition.
  • the polymerizable liquid crystal compound used in the present invention is first dissolved to obtain a polymerizable liquid crystal composition.
  • a composition in which the filler used in the present invention is dispersed in the polymerizable liquid crystal composition may be used.
  • the dispersion in which the filler used in the present invention is dispersed and the polymerizable liquid crystal compound used in the present invention are dissolved.
  • Each of the prepared polymerizable liquid crystal compositions may be prepared and then mixed to form a sealing material composition for a display element.
  • the heating temperature at the time of heating and stirring may be appropriately adjusted in consideration of the solubility of the composition to be used in the organic solvent, but is preferably 15 ° C. to 110 ° C., more preferably 15 ° C. to 105 ° C. from the viewpoint of productivity. 15 to 100 ° C. is more preferable, and 20 to 90 ° C. is particularly preferable.
  • a dispersion stirrer having a stirring blade such as a wet bead mill, a disper, a propeller, or a turbine blade, a paint shaker, a planetary stirring device, a shaker, a shaker, or a rotary evaporator can be used as the dispersion stirrer.
  • a stirring blade such as a wet bead mill, a disper, a propeller, or a turbine blade, a paint shaker, a planetary stirring device, a shaker, a shaker, or a rotary evaporator
  • an ultrasonic irradiation apparatus can be used.
  • wet bead mills and dispersers are preferably used when preparing a dispersion in which a filler is dispersed in an organic solvent, and stirring blades are used when preparing a solution in which a polymerizable liquid crystal compound is dissolved in an organic solvent. It is preferable to use a disperser, a planetary stirrer and a shaker.
  • the number of rotations of stirring when adding the solvent is preferably adjusted appropriately depending on the stirring device used, but the number of rotations of stirring is preferably 10 rpm to 1000 rpm in order to obtain a uniform sealing material composition solution for display elements. 50 rpm to 800 rpm is more preferable, and 100 rpm to 600 rpm is particularly preferable.
  • the sealing material composition for display elements of the present invention may contain the chiral compound and the following components as other components, but the chiral compound and the components described below are organic solvents, packing
  • the material and / or the polymerizable liquid crystal compound can be appropriately used when dispersed or dissolved in the composition.
  • Polymerization inhibitor It is preferable to add a polymerization inhibitor to the sealing material composition for display elements in the present invention.
  • the polymerization inhibitor include phenol compounds, quinone compounds, amine compounds, thioether compounds, nitroso compounds, and the like.
  • phenolic compounds include p-methoxyphenol, cresol, t-butylcatechol, 3.5-di-t-butyl-4-hydroxytoluene, 2.2'-methylenebis (4-methyl-6-t-butylphenol) 2.2′-methylenebis (4-ethyl-6-tert-butylphenol), 4.4′-thiobis (3-methyl-6-tert-butylphenol), 4-methoxy-1-naphthol, 4,4′- Dialkoxy-2,2′-bi-1-naphthol, and the like.
  • quinone compounds include hydroquinone, methylhydroquinone (MEHQ), tert-butylhydroquinone, p-benzoquinone, methyl-p-benzoquinone, tert-butyl-p-benzoquinone, 2,5-diphenylbenzoquinone, 2-hydroxy-1, Examples include 4-naphthoquinone, 1,4-naphthoquinone, 2,3-dichloro-1,4-naphthoquinone, anthraquinone, and diphenoquinone.
  • MEHQ methylhydroquinone
  • p-benzoquinone methyl-p-benzoquinone
  • 2,5-diphenylbenzoquinone 2-hydroxy-1
  • Examples include 4-naphthoquinone, 1,4-naphthoquinone, 2,3-dichloro-1,4-naphthoquinone, anthraquinone
  • amine compounds include p-phenylenediamine, 4-aminodiphenylamine, N.I. N'-diphenyl-p-phenylenediamine, Ni-propyl-N'-phenyl-p-phenylenediamine, N- (1.3-dimethylbutyl) -N'-phenyl-p-phenylenediamine, N.I. N′-di-2-naphthyl-p-phenylenediamine, diphenylamine, N-phenyl- ⁇ -naphthylamine, 4.4′-dicumyl-diphenylamine, 4.4′-dioctyl-diphenylamine and the like.
  • thioether compounds include phenothiazine and distearyl thiodipropionate.
  • nitroso compounds include N-nitrosodiphenylamine, N-nitrosophenylnaphthylamine, N-nitrosodinaphthylamine, p-nitrosophenol, nitrosobenzene, p-nitrosodiphenylamine, ⁇ -nitroso- ⁇ -naphthol, and the like, N, N-dimethyl p-nitrosoaniline, p-nitrosodiphenylamine, p-nitronedimethylamine, p-nitrone-N, N-diethylamine, N-nitrosoethanolamine, N-nitrosodi-n-butylamine, N-nitroso-Nn-butyl- 4-butanolamine, N-nitroso-diisopropanolamine, N-nitroso-N-ethyl-4-butanolamine, 5-nitroso-8-hydroxyquinoline, N-nitrosomorpholine, N-nitros
  • the addition amount of the polymerization inhibitor is preferably 0.01 to 1.0 part by mass with respect to 100 parts by mass of the total content of the polymerizable liquid crystal compound used in the sealing material composition for display elements, and 0.05 to More preferably, it is 0.5 parts by mass.
  • Antioxidant In order to improve the stability of the sealing material composition for display elements in the present invention, it is preferable to add an antioxidant or the like. Examples of such compounds include hydroquinone derivatives, nitrosamine polymerization inhibitors, hindered phenol antioxidants, and more specifically, tert-butyl hydroquinone, methyl hydroquinone, manufactured by Wako Pure Chemical Industries, Ltd.
  • IRGANOX1010 “IRGANOX1035”, “IRGANOX1076”, “IRGANOX1098”, “IRGANOX1135”, “IRGANOX1330”, “IRGANOX1425”, “IRGANOX1520”, “IRGANOX1726”, BASF Corporation “IRGANOX245”, “IRGANOX259”, “IRGANOX3114”, “IRGANOX3790”, “IRGANOX5057”, “IRGANOX565” And so on.
  • the addition amount of the antioxidant is preferably 0.01 to 2.0 parts by mass with respect to 100 parts by mass of the total content of the polymerizable liquid crystal compounds used in the sealing material composition for display elements, and 0.05 to More preferably, it is 1.0 part by mass.
  • the sealing material composition for display elements in this invention contains a photoinitiator. It is preferable to contain at least one photopolymerization initiator.
  • the amount is preferably 0.1 to 10 parts by weight, particularly preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the total content of the polymerizable liquid crystal compounds used in the sealing material composition for display elements of the photopolymerization initiator. These can be used alone or in combination of two or more, and a sensitizer or the like may be added.
  • Thermal polymerization initiator A thermal polymerization initiator may be used in combination with the photopolymerization initiator in the sealing material composition for display elements in the present invention. Specifically, “V-40” and “VF-096” manufactured by Wako Pure Chemical Industries, Ltd., “Perhexyl D” and “Perhexyl I” of Nippon Oil & Fats Co., Ltd. (currently Nippon Oil Co., Ltd.) Etc.
  • the amount of the thermal polymerization initiator used is preferably 0.1 to 10 parts by mass, and 0.5 to 5 parts by mass with respect to 100 parts by mass of the total content of the polymerizable liquid crystal compounds used in the sealing material composition for display elements. Particularly preferred. These can be used alone or in combination of two or more.
  • the sealing material composition for display elements in the present invention further contains at least one surfactant in a range that does not impair the effects of the present invention in order to reduce film thickness unevenness in the case of an optical anisotropic body. May be.
  • Surfactants that can be included include alkyl carboxylates, alkyl phosphates, alkyl sulfonates, fluoroalkyl carboxylates, fluoroalkyl phosphates, fluoroalkyl sulfonates, polyoxyethylene derivatives, fluoro Examples thereof include alkylethylene oxide derivatives, polyethylene glycol derivatives, alkylammonium salts, fluoroalkylammonium salts and the like, and fluorine-containing surfactants are particularly preferable.
  • the addition amount of the surfactant is preferably 0.01 to 2 parts by mass with respect to 100 parts by mass of the total content of the polymerizable liquid crystal compounds used in the sealing material composition for display elements, and 0.05 to 0 More preferably, it is 5 parts by mass.
  • the tilt angle at the air interface can be effectively reduced.
  • the sealing material composition for display elements in the present invention is represented by the following general formula (7), which has the effect of effectively reducing the tilt angle of the air interface when it is used as a film without impairing the effects of the present invention. And a compound having a repeating unit having a weight average molecular weight of 100 or more.
  • each of R 11 , R 12 , R 13 and R 14 independently represents a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and one or more hydrogen atoms in the hydrocarbon group It may be substituted with a halogen atom.
  • Examples of suitable compounds represented by the general formula (7) include polyethylene, polypropylene, polyisobutylene, paraffin, liquid paraffin, chlorinated polypropylene, chlorinated paraffin, and chlorinated liquid paraffin.
  • the addition amount of the compound represented by the general formula (7) is 0.01 to 1 part by mass with respect to 100 parts by mass of the total content of the polymerizable liquid crystal compounds used in the sealing material composition for display elements. Preferably, the amount is 0.05 to 0.5 parts by mass.
  • additives such as polymerizable compounds having no liquid crystallinity, thixotropic agents, dispersants, chain transfer agents and the like are not impaired in the properties of the sealing material composition for display elements of the present invention. Can be added.
  • the content is preferably 0.01 to 1 part by mass, and 0.05 to 0.5 part by mass with respect to 100 parts by mass of the total content of the polymerizable liquid crystal compound used in the sealing material composition for display elements. It is more preferable that (Method for producing sealing material composition for display element)
  • the sealing material composition for display elements of the present invention can be produced by mixing at least one or more fillers and two or more polymerizable liquid crystal compounds.
  • a sealing material composition for a display element in which a polymerizable liquid crystal compound is brought into a liquid crystal state and a filler is dispersed can be obtained by stirring or ultrasonic irradiation.
  • a stirring method a planetary stirring apparatus, a shaker, a laboratory mixer, a stirring propeller, a shaker, a rotary evaporator, or the like can be used.
  • the temperature during the production may rise, but the heating from the outside is arbitrary, and the heating is performed even when heated. It is not necessary.
  • the temperature during production is preferably 15 ° C. or higher and 70 ° C. or lower, more preferably 20 ° C. or higher and 50 ° C. or lower, and particularly preferably 25 ° C. or higher and 45 ° C. or lower.
  • the composition consisting of 2 or more types of polymeric liquid crystal compounds to be used maintains liquid crystallinity at room temperature.
  • the filler used in the present invention is first dispersed in the organic solvent to obtain a dispersion, and then the present invention is applied.
  • a polymerizable liquid crystal compound to be used may be dissolved to form a composition.
  • the polymerizable liquid crystal compound used in the present invention is first dissolved to obtain a polymerizable liquid crystal composition.
  • a composition in which the filler used in the present invention is dispersed may be used.
  • the dispersion in which the filler used in the present invention is dispersed and the polymerizable liquid crystal compound used in the present invention are dissolved.
  • the prepared polymerizable liquid crystal composition may be prepared and mixed to form a sealing material composition for a display element.
  • heating from the outside during production is optional, and it may be heated or not heated.
  • the temperature during production is preferably 15 ° C. or higher and 70 ° C. or lower, more preferably 20 ° C. or higher and 50 ° C. or lower, and particularly preferably 25 ° C. or higher and 45 ° C. or lower.
  • the sealing material composition for a display element of the present invention can also be produced by adding and stirring a filler to a liquid state product obtained by heating and melting one or more polymerizable liquid crystal compounds. In this case, heating is required to melt the polymerizable compound, but the heating temperature is preferably set to a temperature of ⁇ 10 ° C. from the temperature at which all the polymerizable compounds used melt.
  • the sealing material composition for display elements of the present invention is used as a base material sealing protective agent or a sealing agent for display elements.
  • Examples of the display element include a liquid crystal display element using a liquid crystal material, an organic light emitting display element using an organic light emitting diode, a quantum dot display element using a quantum dot, etc., and sealing a substrate and a substrate of each display element It can be suitably used as a protective agent or a sealing agent for the frame portion of each display element.
  • the display element of the present invention is a laminate in which a base material layer, a base material sealing protective layer using the display element sealing material composition of the present invention, and other layers such as an inorganic layer are laminated as necessary. It is preferable that (Inorganic layer) In the present invention, an inorganic layer may be laminated on the substrate in order to develop higher gas barrier properties and water vapor barrier properties.
  • the inorganic layer is an oxide of at least one metal selected from the group consisting of Al, Si, Zn, Sn, Ti, Cr, Ni, and In, a nitride of the metal, or an oxynitride of the metal. Preferably there is.
  • the inorganic layer is more preferably formed of an oxide or a double oxide of Al, Si, Zn, Sn, Ti, Cr, Ni, and In.
  • the inorganic layer may be provided only on one side of the substrate, or may be provided on both sides of the substrate.
  • the content of Si in the double oxide is not particularly limited, but is preferably 20 parts by mass to 80 parts by mass, and more preferably 30 parts by mass to 70 parts by mass.
  • Si content is within the above range, a barrier film having higher transparency and excellent gas barrier performance can be provided.
  • the weight ratio of Zn to the total amount of Zn and Sn (Zn / Zn + Sn) in the double oxide is preferably 0.3 to 0.99, more preferably 0.5 to 0.9. preferable. When it exists in the said range, gas barrier property can be improved further.
  • the film thickness of the inorganic layer is not particularly limited, but is preferably 30 nm to 3000 nm, and more preferably 50 nm to 1000 nm. When the film thickness is in the above range, the gas barrier performance can be further enhanced.
  • the refractive index of the inorganic layer is not particularly limited, but is preferably 1.9 or less, and more preferably 1.8 or less. Since the refractive index of a plastic film such as polyethylene naphthalate or polyethylene terephthalate used as the substrate is about 1.6 to 1.75, the refractive index of the inorganic layer can be reduced to 1.9 or less. The reflection of light at the interface between the inorganic layer and the inorganic layer can be further suppressed. That is, the transparency of the barrier layer is further enhanced. (Base material)
  • the sealing material composition for display elements of the present invention is used as a base material sealing protective agent for display elements, but the base material used for the display elements is usually used for liquid crystal devices, displays, optical components and optical films.
  • a base material that has heat resistance that can withstand heating as needed during drying after application of the sealing material composition for display elements of the present invention.
  • a base material include organic materials such as a glass base material, a metal base material, a ceramic base material, and a plastic base material, but the sealing material composition for a display element of the present invention having excellent gas barrier properties and water vapor barrier properties.
  • the product is particularly effective in improving gas barrier properties and water vapor barrier properties when the following organic material base is used.
  • the substrate is an organic material
  • examples thereof include cellulose derivatives, polyolefins, polyesters, polycarbonates, polyacrylates (acrylic resins), polyarylate, polyethersulfone, polyimide, polyphenylene sulfide, polyphenylene ether, nylon, and polystyrene.
  • plastic base materials such as polyester, polystyrene, polyacrylate, polyolefin, cellulose derivative, polyarylate, and polycarbonate are preferable, and base materials such as polyacrylate, polyolefin, and cellulose derivative are more preferable, and COP (cycloolefin polymer) is used as the polyolefin.
  • TAC triacetyl cellulose
  • PMMA polymethyl methacrylate
  • these substrates may be subjected to surface treatment.
  • the surface treatment include ozone treatment, plasma treatment, corona treatment, silane coupling treatment, and the like.
  • an organic thin film, an inorganic oxide thin film, a metal thin film, etc. are provided on the surface of the substrate by a method such as vapor deposition, or in order to add optical added value.
  • the material may be a pickup lens, a rod lens, an optical disk, a retardation film, a light diffusion film, a color filter, or the like.
  • a pickup lens, a retardation film, a light diffusion film, and a color filter that have higher added value are preferable.
  • Substrate orientation treatment In addition, the substrate is usually subjected to an orientation treatment so that the display element sealing material composition is oriented when the display element sealing material composition of the present invention is applied and dried, or the orientation is applied.
  • a film may be provided. Examples of the alignment treatment include stretching treatment, rubbing treatment, polarized ultraviolet visible light irradiation treatment, ion beam treatment, and the like. When the alignment film is used, a known and conventional alignment film is used.
  • Such alignment films include polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyether sulfone, epoxy resin, epoxy acrylate resin, acrylic resin, coumarin compound, chalcone.
  • the compound include compounds, cinnamate compounds, fulgide compounds, anthraquinone compounds, azo compounds, and arylethene compounds.
  • the compound subjected to the alignment treatment by rubbing is preferably an alignment treatment or a compound in which crystallization of the material is promoted by inserting a heating step after the alignment treatment.
  • the substrate and the alignment-treated film using an alignment film may be collectively referred to as a substrate.
  • the sealing material composition for display elements of the present invention is used as a sealant for display elements. Specifically, it is used as a layer for sealing the side surface of the barrier layer covering the layer containing a light-emitting organic compound.
  • sealing material composition for display element As a method for applying the sealing material composition for display elements of the present invention to a substrate, a substrate or a material to be sealed, an applicator method, bar coating method, spin coating method, roll coating method, direct gravure coating method, reverse gravure coating Known and commonly used methods such as a method, a flexo coating method, an ink jet method, a die coating method, a cap coating method, a dip coating method, a slit coating method, and a discharge method using a dispenser can be performed.
  • the dispenser method and the like can be used without using an organic solvent. However, when an organic solvent is used, the organic solvent is required for volatilization after the display element sealing material composition is applied to the substrate. Dry accordingly.
  • the liquid crystal compound in the sealing material composition for display elements of the present invention is horizontal with respect to the substrate after volatilizing the organic solvent.
  • the alignment, vertical alignment, hybrid alignment, or cholesteric alignment is performed by irradiation with light such as ultraviolet rays or heating.
  • irradiation with ultraviolet light specifically, irradiation with ultraviolet light of 390 nm or less is preferable, and irradiation with light having a wavelength of 250 to 370 nm is most preferable.
  • the sealing material composition for a display element causes decomposition or the like due to ultraviolet light of 390 nm or less, it may be preferable to perform polymerization treatment with ultraviolet light of 390 nm or more.
  • This light is preferably diffused light and unpolarized light.
  • Examples of the method for polymerizing the sealing material composition for a display device of the present invention include a method of irradiating active energy rays and a thermal polymerization method. However, it does not require heating and is active because the reaction proceeds at room temperature. A method of irradiating energy rays is preferable, and among them, a method of irradiating light such as ultraviolet rays is preferable because the operation is simple.
  • the temperature at the time of irradiation is set to 40 ° C. or less as much as possible in order to avoid the induction of thermal polymerization of the sealing material composition for display elements, so that the sealing material composition for display elements of the present invention can maintain the liquid crystal phase. It is preferable to do.
  • the liquid crystal composition usually has a liquid crystal phase within a range from the C (solid phase) -N (nematic) transition temperature (hereinafter abbreviated as the CN transition temperature) to the NI transition temperature in the temperature rising process. Indicates.
  • the temperature lowering process since the thermodynamically non-equilibrium state is obtained, there is a case where the liquid crystal state is not solidified even at a temperature below the CN transition temperature.
  • the liquid crystal composition in a supercooled state is also included in the state in which the liquid crystal phase is retained.
  • irradiation with ultraviolet light of 390 nm or less is preferable, and irradiation with light having a wavelength of 250 to 370 nm is most preferable.
  • the sealing material composition for a display element causes decomposition or the like due to ultraviolet light of 390 nm or less, it may be preferable to perform polymerization treatment with ultraviolet light of 390 nm or more. This light is preferably diffused light and unpolarized light. Ultraviolet irradiation intensity in the range of 0.05kW / m 2 ⁇ 10kW / m 2 is preferred.
  • the range of 0.2 kW / m 2 to 2 kW / m 2 is preferable.
  • the ultraviolet intensity is less than 0.05 kW / m 2 , it takes a lot of time to complete the polymerization.
  • the strength exceeds 2 kW / m 2 , liquid crystal molecules in the sealing material composition for display elements tend to be photodecomposed, and a large amount of polymerization heat is generated, resulting in an increase in temperature during the polymerization.
  • the order parameter of the liquid crystal changes, and there is a possibility that the retardation of the film after polymerization is distorted.
  • the orientation state of the unpolymerized part is changed by applying an electric field, a magnetic field or temperature, and then the unpolymerized part is polymerized.
  • An optical anisotropic body having a plurality of regions having orientation directions can also be obtained.
  • the orientation is regulated by applying an electric field, a magnetic field, or temperature to the display element sealing material composition in an unpolymerized state in advance.
  • a film having a plurality of regions having different orientation directions can also be obtained by polymerizing by irradiating light from above the mask while maintaining.
  • the sealing material composition for display elements of the present invention can be suitably used as a sealing agent for liquid crystal display elements and organic light emitting display elements. Specifically, it can be suitably used as a sealing agent for display elements such as liquid crystal displays, organic EL displays, inorganic EL displays, quantum dot displays, and quantum rod displays.
  • the coating amount of the sealing material composition for display elements is not limited, but it is usually preferable that the layer thickness of the sealing agent after drying is 50 ⁇ m to 200 ⁇ m on the sealing material. 50 ⁇ m to 150 ⁇ m is more preferable, and 50 ⁇ m to 120 ⁇ m is particularly preferable.
  • the sealing material composition for a display element of the present invention can be suitably used as a substrate sealing protective agent used for a display element. Specifically, it can be used for display elements such as an organic EL display, an inorganic EL display, a quantum dot display, and a quantum rod display, and can be suitably used as a base material sealing protective layer when used on a base material. .
  • the layer thickness of the base material sealing protective agent after drying is usually 40 ⁇ m to 80 ⁇ m on the base material. It is preferably 40 ⁇ m to 70 ⁇ m, more preferably 40 ⁇ m to 60 ⁇ m.
  • Polymeric liquid crystal compositions (U-2) to (U-15) were obtained under the same conditions as in the preparation. (Adjustment of polymerizable liquid crystal composition (U-16)) 45 parts of the compound represented by formula (B-1), 45 parts of the compound represented by formula (B-2), 10 parts of the compound represented by formula (C-1), p-methoxyphenol (MEHQ) 0 .1 part was heated and stirred at 100 ° C.
  • Irgacure 907 (Irg.907: manufactured by BASF Japan Ltd.), Irgacure TPO (TPO: BASF) 3 parts of Japan Co., Ltd.) and 0.2 part of MegaFuck F-554 (F-554: manufactured by DIC Corporation) were added and further stirred to obtain a solution (U-16).
  • Tables 1 to 3 show specific compositions of the polymerizable liquid crystal compositions (U-1) to (U-17) of the present invention.
  • phase transition temperatures of the polymerizable liquid crystal compositions (U-2) to (U-13) are the same as those of (U-1), and the phase transition temperatures of (U-14) to (U-15) are After raising the temperature to 190 ° C., the measurement was performed under the same conditions as (U-1).
  • phase transition temperature of the polymerizable liquid crystal compositions (U-16) and (U-17) is the same as (U-1), which is obtained by thinly spreading the polymerizable liquid crystal composition on a glass substrate with a spatula. It was observed and measured after drying and heating up under conditions.
  • phase transition temperatures of the polymerizable liquid crystal compositions (U-1) to (U-17) are shown in Table 4 below.
  • P (water vapor transmission rate) ⁇ P (laminate) ⁇ P (PET base material) ⁇ / ⁇ P (PET base material) ⁇ P (laminate) ⁇ : Formula (1) (In formula (1), P represents the water vapor transmission rate of each layer.) (Flexibility evaluation) Using a mandrel type bending tester having a curvature radius of 6 mm, the bending property of the sealing material laminate (1) was evaluated (JIS SK5600-5-1), and no defects such as cracks were generated. The flexibility was evaluated as follows according to the occurrence of cracks.
  • sealing material laminate (16) in which a sealing material layer was laminated on PET.
  • Preparation of sealing material laminate (17) A sealing material laminate (17) was obtained under the same conditions as in the production of the sealing material laminate (16) except that the sealing material composition (16) was changed to the sealing material composition (17).
  • Comparative Example 1 By adding 82.5 g of toluene to 75 g of the polymerizable liquid crystal composition (U-4) and stirring at room temperature, a comparative sealing material composition (C1) was obtained.
  • a sealing material composition for comparison using a wire bar on a PET film having a thickness of 12 microns rubbed with a nylon cloth (water vapor transmission rate at 40 ° C. and 90% RH of 50 g / m 2 ⁇ day (100 ⁇ m conversion)).
  • (C1) was applied, and after solvent drying at 80 ° C., UV irradiation was performed at 500 mJ / cm 2 using a conveyor-type high-pressure mercury lamp, and a comparative laminate in which a sealing material layer was laminated on PET ( C1) was obtained.
  • the water vapor transmission rate was measured by a 40 ° C. 90% RH cup method (JIS Z0208-1976).
  • the water vapor permeability of the sealing material layer calculated from the above formula (1) was 104 g / m 2 ⁇ day (100 ⁇ m conversion).
  • the bending property of the comparative laminate was evaluated using a mandrel type bending tester having a curvature radius of 6 mm (JIS SK5600-5-1), and no defects such as cracks were generated.
  • Example 18 (Lamination of inorganic film)
  • the film forming chamber was evacuated by a vacuum pump and the pressure was reduced to 5.0 ⁇ 10 ⁇ 4 Pa. Thereafter, sputtering was performed under the conditions shown in the following film formation condition A to form a SiZnSnO film having a thickness of 150 nm as an inorganic film on the laminate (1) to obtain a vapor deposition laminate (18).
  • Example 19 Flexibility evaluation of the obtained vapor-deposited laminate (18) was performed in the same manner as in Example 1. (Examples 19 to 22) Except for changing the sealing material laminate (1) to the sealing material laminate (2), (8), (10) and (14), respectively, under the same conditions as the production of the vapor deposition laminate (1), Vapor deposited laminates (19) to (22) were obtained.
  • Example 23 Al is attached to the second cathode, and sputtering is performed under the conditions shown in the following film formation condition B to form an Al 2 O 3 film having a thickness of 150 nm as an inorganic film on the sealing material stack (1). 23) was obtained.
  • the water vapor transmission rate measurement and the flexibility evaluation of the obtained vapor-deposited laminate (23) were carried out in the same manner as in Example 18.
  • Comparative Example 2 A comparative vapor deposition laminate (C2) was obtained in the same manner as in Example 18 except that the sealing material layer (1) was changed to a PET film having a thickness of 12 microns.
  • sealing material composition (18) 100 g of dispersion B was added to 90 g of the polymerizable liquid crystal composition (U-18), stirred at room temperature, and then degassed with a solvent in a planetary mixer to thereby uniformly disperse the filler b (18) Got.
  • a sealing material composition (18) is applied on a PET substrate film having a thickness of 50 ⁇ m rubbed with a nylon cloth using an applicator, and UV irradiation is performed at 500 mJ / cm 2 using a conveyor type high-pressure mercury lamp. Then, a cured product of the sealing material composition (18) was obtained.
  • the cured product was peeled off from the PET substrate to obtain a sealing sheet (18) having a thickness of 50 ⁇ m.
  • the water vapor transmission rate was measured by the 40 ° C. 90% RH cup method (JIS Z0208-1976), and it was 15.2 g / m 2 ⁇ day (100 ⁇ m conversion).
  • the sealing material layer using the sealing material composition of the present invention containing a filler in the polymerizable liquid crystal composition has excellent barrier properties and imparts flexibility to the inorganic vapor deposition layer. It became clear that it was excellent also as a vapor deposition anchor layer which can be performed.

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Abstract

L'invention fournit une composition de matériau d'encapsulation pour élément d'affichage qui possède des propriétés de barrière au gaz élevées et des propriétés de barrière de vapeur d'eau. En outre, l'invention fournit un agent de scellement pour élément d'affichage mettant en œuvre cette composition, un agent d'encapsulation et protection de matériau de base, un élément d'affichage à cristaux liquides mettant en œuvre cet agent de scellement et/ou agent d'encapsulation et protection de matériau de base, un élément d'affichage luminescent organique, et un élément d'affichage à points quantiques. Plus précisément, l'invention fournit une composition de matériau d'encapsulation pour élément d'affichage qui comprend au moins une sorte de matériau de charge, et une ou plusieurs sortes de composé cristaux liquides polymérisable. Enfin, l'invention fournit un agent de scellement mettant en œuvre cette composition, un agent d'encapsulation et protection de matériau de base, et un élément d'affichage mettant en œuvre cet agent de scellement et/ou cet agent d'encapsulation et protection de matériau de base.
PCT/JP2017/044504 2016-12-16 2017-12-12 Composition de matériau d'encapsulation pour élément d'affichage, et élément d'affichage mettant en œuvre celui-ci WO2018110529A1 (fr)

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US11697666B2 (en) 2021-04-16 2023-07-11 Gilead Sciences, Inc. Methods of preparing carbanucleosides using amides
US11767337B2 (en) 2020-02-18 2023-09-26 Gilead Sciences, Inc. Antiviral compounds
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JPWO2018003515A1 (ja) * 2016-06-28 2018-12-20 Dic株式会社 重合性液晶組成物
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US12030903B2 (en) 2021-02-17 2024-07-09 Gilead Sciences, Inc. Antiviral compounds
US11697666B2 (en) 2021-04-16 2023-07-11 Gilead Sciences, Inc. Methods of preparing carbanucleosides using amides

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