WO2019240015A1 - 表示装置および表示装置用組成物 - Google Patents
表示装置および表示装置用組成物 Download PDFInfo
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- WO2019240015A1 WO2019240015A1 PCT/JP2019/022630 JP2019022630W WO2019240015A1 WO 2019240015 A1 WO2019240015 A1 WO 2019240015A1 JP 2019022630 W JP2019022630 W JP 2019022630W WO 2019240015 A1 WO2019240015 A1 WO 2019240015A1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing 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
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
-
- 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
- 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
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]
-
- 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
- H10K59/40—OLEDs integrated with touch screens
-
- 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
- H10K59/871—Self-supporting sealing arrangements
- H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants
-
- 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
-
- 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
- H10K59/875—Arrangements for extracting light from the devices
- H10K59/879—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
-
- 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
- H10K59/8791—Arrangements for improving contrast, e.g. preventing reflection of ambient light
Definitions
- the present invention relates to a display device and a composition for a display device.
- Patent Document 1 discloses a light-emitting element including a benzo [b] naphtho [1,2-d] furan compound having a wide band gap that gives excellent color purity as blue.
- the present invention has been made in view of the above circumstances, and provides a display device with improved blue color purity.
- a display device with improved blue color purity can be obtained by using a composition containing an indole compound represented by the following general formula [I] closer to the observation side than the light emitting element. Completed.
- the following display device and display device composition are provided.
- a light emitting element One or more layers (A) which are located on the observation side of the light emitting element and are formed of a composition containing an indole compound represented by the following general formula [I]:
- a display device comprising: (In the above general formula [I], R 1 represents a linear, branched or cyclic alkyl group, aralkyl group, substituted or unsubstituted aromatic group, or —COR 3 group, and R 2 represents a substituted or unsubstituted aromatic group.
- R 3 represents a linear, branched or cyclic alkyl group, an aralkyl group, a substituted or unsubstituted aromatic group
- X 1 to X 4 may be the same or different and each represents a hydrogen atom Represents a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a nitro group, a carboxyl group, and an ester group, and Y and Z may be the same or different
- R 4 Represents a —CO— group, an R 5 —OC ( ⁇ O) — group, an R 6 — group, or an R 7 —SO 2 — group, wherein R 4 , R 5 and R 7 are linear, branched or cyclic alkyl.
- the display device further includes at least one compound selected from a resin and a polymerizable compound.
- a display device which is an organic EL display device or a liquid crystal display device.
- the layer (A) is selected from a sealing layer, a barrier layer, a touch panel layer, a planarization layer, an overcoat layer, a color filter layer, a surface protective layer, an adhesive layer, an adhesive layer, a microlens and a polarizing plate.
- a display device comprising at least one layer.
- a composition for forming a layer (A) located on the observation side of the light emitting element in a display device including the light emitting element The composition for display apparatuses containing the indole type compound shown by the following general formula [I].
- R 1 represents a linear, branched or cyclic alkyl group, aralkyl group, substituted or unsubstituted aromatic group, or —COR 3 group
- R 2 represents a substituted or unsubstituted aromatic group.
- R 3 represents a linear, branched or cyclic alkyl group, an aralkyl group, a substituted or unsubstituted aromatic group
- X 1 to X 4 may be the same or different and each represents a hydrogen atom Represents a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a nitro group, a carboxyl group, and an ester group, and Y and Z may be the same or different
- R 4 Represents a —CO— group, an R 5 —OC ( ⁇ O) — group, an R 6 — group, or an R 7 —SO 2 — group, wherein R 4 , R 5 and R 7 are linear, branched or cyclic alkyl.
- composition for a display device comprising at least one compound selected from a resin and a polymerizable compound.
- composition for a display device In the composition for a display device according to the above [5] or [6], A composition for a display device, wherein the display device is an organic EL display device or a liquid crystal display device. [8] In the composition for a display device according to any one of the above [5] to [7], Composition for forming at least one layer selected from a sealing layer, a barrier layer, a touch panel layer, a planarizing layer, an overcoat layer, a color filter layer, a surface protective layer, a microlens and a polarizing plate in a display device A composition for a display device.
- a display device with improved blue color purity can be provided.
- FIG. 2 is a 1 H-NMR chart of an indole compound (Exemplary Compound 14) synthesized in Example 1.
- FIG. 3 is a 1 H-NMR chart of an indole compound (Exemplary Compound 15) synthesized in Example 2.
- FIG. 2 is a 1 H-NMR chart of an indole compound (Exemplary Compound 16) synthesized in Example 3.
- FIG. 2 is a 1 H-NMR chart of an indole compound synthesized in Example 4 (Exemplary Compound 12).
- FIG. 2 is a 1 H-NMR chart of an indole compound (Exemplary Compound 17) synthesized in Example 5.
- FIG. 2 is a 1 H-NMR chart of an indole compound (Exemplary Compound 41) synthesized in Example 6.
- FIG. 1 is a 1 H-NMR chart of an indole compound (Exemplary Compound 41) synthesized in Example 6.
- the display device is formed of a light emitting element and a composition (P) that is located closer to the observation side than the light emitting element and includes an indole compound (Q) represented by the following general formula [I]. And one or more layers (A).
- R 1 represents a linear, branched or cyclic alkyl group, aralkyl group, substituted or unsubstituted aromatic group, or —COR 3 group
- R 2 represents a substituted or unsubstituted aromatic group
- R 3 represents a linear, branched or cyclic alkyl group, an aralkyl group, a substituted or unsubstituted aromatic group
- X 1 to X 4 may be the same or different and each represents a hydrogen atom Represents a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a nitro group, a carboxyl group, and an ester group, and Y and Z may be the same or different
- R 4 Represents a —CO— group, an R 5 —OC ( ⁇ O) — group, an R 6 — group, or an R 7 —SO 2 — group, wherein R 4 , R 5 and R 7 are linear, branched or cyclic alkyl.
- R 6 is a linear, branched or cyclic alkyl group, a linear, branched or cyclic fluoroalkyl group, a nitro group or a substituted or unsubstituted (Y and Z do not simultaneously become R 6 -groups.
- the wavy line in the formula indicates E, Z, or a mixture thereof with respect to the double bond.
- the present inventors have intensively studied to provide a display device with improved blue color purity, and as a result, the composition (P) containing the indole compound (Q) is closer to the observation side than the light emitting element. It has been found that a display device with improved blue color purity can be obtained by using it.
- the indole compound (Q) represented by the general formula [I] an excellent shielding effect is exhibited up to a long wavelength region having a wavelength of about 420 nm. Therefore, the light from the light emitting element is provided by including one or more layers (A) which are located on the observation side of the light emitting element and formed of the composition (P) containing the indole compound (Q).
- the layer (A) containing the indole-based compound (Q) When transmitted through the layer (A), the layer (A) containing the indole-based compound (Q) can effectively cut the wavelength region of 420 nm or less, that is, the purple region, and improve the blue color purity. Can be made. In addition, since the layer (A) containing the indole compound (Q) has little absorption in the region exceeding the wavelength of 420 nm, the display device according to the present embodiment improves the blue color purity while keeping the overall luminance good. be able to.
- the display device according to the present embodiment is not particularly limited, and examples thereof include an organic EL display device, a liquid crystal display device, and a micro LED.
- the layer (A) is not particularly limited as long as the layer (A) is a layer positioned closer to the observation side than the light emitting element and can contain the indole compound (Q).
- examples thereof include a resin layer containing the compound (Q) and at least one compound (R) selected from a resin and a polymerizable compound.
- the layer (A) is classified by function, for example, a sealing layer, a barrier layer, a touch panel layer, a planarizing layer, an overcoat layer, a color filter layer, a surface protective layer, an adhesive layer, an adhesive layer, a microlens. And one or two or more layers selected from polarizing plates and the like.
- the configuration of the display device according to the present embodiment is not particularly limited as long as the layer (A) is positioned on the observation side of the light emitting element, and a known configuration can be adopted.
- an organic EL display device will be described as an example.
- a display device 100 shown in FIG. 1 is an organic EL display device, and has a barrier layer 21 (which may be the touch panel layer 21 or the surface protective layer 21), an over layer as a layer positioned on the observation side of the light emitting element 10.
- a coating layer 22 (which may be the sealing layer 22 or the barrier layer 22), a planarization layer 23 (which may be the sealing layer 23), a barrier layer 24, and the like are included.
- the indole compound (Q) is blended in one or more layers and can function as the layer (A).
- each layer includes, for example, a light emitting element 10 provided on a base material layer 50, a planarization layer 23 provided on the base material layer 50 so as to cover the light emitting element 10, and a planarization layer. 23, a barrier layer 24 provided on the surface, an overcoat layer 22 provided on the base material layer 50 so as to cover the planarizing layer 23 and the barrier layer 24, and provided on the overcoat layer 22 And a barrier layer 21.
- the specific configuration of each layer is not particularly limited, and an appropriate configuration can be employed based on generally known information.
- Such a display device 100 can be manufactured based on generally known information.
- a display device 100 shown in FIG. 2 is an organic EL display device, and a barrier layer 21 (which may be the touch panel layer 21 or the surface protective layer 21), a color, as a layer positioned on the observation side of the light emitting element 10. It has a filter layer 25, a sealing layer 26, a barrier layer 24, and the like. Among these layers, the indole compound (Q) is blended in one or more layers and can function as the layer (A).
- the display device 100 illustrated in FIG. 2 includes, for example, a light emitting element 10 provided on a base material layer 50, a barrier layer 24 provided to cover the light emitting element 10, and the light emitting element 10 and the barrier layer 24.
- the specific configuration of each layer is not particularly limited, and an appropriate configuration can be employed based on generally known information.
- Such a display device 100 can be manufactured based on generally known information.
- the indole compound (Q) according to this embodiment is a compound represented by the following general formula [I].
- R 1 represents a linear, branched or cyclic alkyl group, an aralkyl group, a substituted or unsubstituted aromatic group, or a —COR 3 group.
- the straight chain or branched alkyl group is a straight chain or branched alkyl group having 1 to 12 carbon atoms, and specifically includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group.
- the cyclic alkyl group is an optionally substituted cyclic alkyl group having 3 to 12 carbon atoms, and specifically includes a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a cyclopentanyl group.
- cyclodecanyl group 2-hydroxycyclohexyl group, 2,3-dihydroxycyclohexyl group, 2-aminocyclohexyl group, 2,3-diaminocyclohexyl group, 2-mercaptocyclohexyl group and the like.
- Examples of the aralkyl group include groups substituted with aromatic hydrocarbons or aromatic heterocycles.
- Aralkyl groups substituted by aromatic hydrocarbons include, for example, benzyl group, 2-hydroxybenzyl group, 2,4-dihydroxybenzyl group, 2,4,6-trihydroxybenzyl group, 2-aminobenzyl group, 2 , 4-Diaminobenzyl group, 2,4,6-triaminobenzyl group, 2-mercaptobenzyl group, 2,4-dimercaptobenzyl group, 2,4,6-trimercaptobenzyl group, 2,4-difluorobenzyl Group, pentafluorophenylmethyl group, 4-vinylphenylmethyl group, phenethyl group, 2-naphthylmethyl group and the like.
- Examples of the aralkyl group substituted with an aromatic heterocycle include a 2-pyridylmethyl group, a 3-thiophenylmethyl group, a 3-furylmethyl group,
- the aromatic group is an aromatic group having 6 to 30 carbon atoms, and specific examples include phenyl, naphthyl, biphenylyl, terphenylyl and the like.
- Aromatic group substituents include: hydroxyl group; amino group; cyano group; halogen atom which is fluorine, chlorine, iodine and bromine; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group Tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1,2-dimethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, n-hexyl group, etc.
- Examples thereof include an alkoxy group having 1 to 6 carbon atoms.
- R 3 in the —COR 3 group represents a linear, branched or cyclic alkyl group, an aralkyl group, or a substituted or unsubstituted aromatic group. These groups are the same as those exemplified for R 1 .
- R 1 is a linear or branched alkyl group having 1 to 12 carbon atoms, a cyclic alkyl group having 3 to 12 carbon atoms, or a substituted or non-substituted group having 6 to 30 carbon atoms.
- a substituted aromatic group is preferable, a linear or branched alkyl group having 1 to 12 carbon atoms or a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms is more preferable, and a linear or branched group having 1 to 6 carbon atoms. And a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms is more preferable.
- R 2 represents a substituted or unsubstituted aromatic group.
- the “substituted or unsubstituted aromatic group” is the same as the group exemplified for R 1 .
- R 2 a linear or branched alkyl group having 1 to 12 carbon atoms, a cyclic alkyl group having 3 to 12 carbon atoms, or a substitution having 6 to 30 carbon atoms or
- An unsubstituted aromatic group is preferable, a linear or branched alkyl group having 1 to 12 carbon atoms or a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms is more preferable, and a substituted or non-substituted aromatic group having 6 to 20 carbon atoms is more preferable.
- Substituted aromatic groups are more preferred.
- X 1 to X 4 may be the same or different and each represents a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a nitro group, a carboxyl group, or an ester group.
- halogen atom include fluorine, chlorine, iodine and bromine.
- the linear, branched or cyclic alkyl group is the same as the group exemplified for R 1 .
- the linear or branched alkoxy group is an alkoxy group having 1 to 6 carbon atoms, and specifically includes a methoxy group, an ethoxy group, a methoxy group, an i-propoxy group, an n-propoxy group, an s-butoxy group, a t- Examples include butoxy group, pentyloxy group, hexyloxy group and the like.
- the cyclic alkoxy group is a cyclic alkoxy group having 6 to 15 carbon atoms, and specific examples include a cyclopentyloxy group, a cyclohexyloxy group, a 2-methylcyclohexyloxy group, and a 2,4-dimethylcyclohexyloxy group. be able to.
- X 1 to X 4 may be the same or different, and are preferably a hydrogen atom, a halogen atom, or a linear or branched alkyl group having 1 to 12 carbon atoms.
- Y and Z may be the same or different and each represents an R 4 —CO— group, an R 5 —OC ( ⁇ O) — group, an R 6 — group, or an R 7 —SO 2 — group.
- R 4 , R 5 and R 7 represent a linear, branched or cyclic alkyl group, an aralkyl group, a linear, branched or cyclic fluoroalkyl group or a substituted or unsubstituted aromatic group.
- R 6 represents a linear, branched or cyclic alkyl group, a linear, branched or cyclic fluoroalkyl group, a nitro group, or a substituted or unsubstituted aromatic group. As described above, R 6 does not contain a cyano group. Y and Z do not combine to form a ring.
- linear, branched or cyclic alkyl group “aralkyl group” and “substituted or unsubstituted aromatic group” are the same as those exemplified for R 1 .
- the linear, branched or cyclic fluoroalkyl group is obtained by substituting one or more hydrogen atoms of the linear, branched or cyclic alkyl group exemplified by R 1 with a fluorine atom.
- Y and Z are preferably an R 4 —CO— group, an R 5 —OC ( ⁇ O) — group, an R 6 — group, or an R 7 —SO 2 — group.
- R 4 and R 5 are preferably a linear, branched or cyclic alkyl group, an aralkyl group, a linear, branched or cyclic fluoroalkyl group.
- R 6 is preferably a linear, branched or cyclic alkyl group, a linear, branched or cyclic fluoroalkyl group, or a substituted or unsubstituted aromatic group.
- R 7 is preferably a substituted or unsubstituted aromatic group.
- the indole compound of this embodiment is a compound represented by the general formula [I] (E-form or Z-form) or a mixture of the E-form and Z-form.
- the novel indole compound (Q) according to the present embodiment exhibits a shielding effect up to a long wavelength region having a wavelength of about 420 nm, and can exhibit a shielding effect in a long wavelength ultraviolet region with a very small amount.
- the indole compound (Q) according to the present embodiment is excellent in heat resistance, it can exhibit a long wavelength ultraviolet ray shielding effect for a long time, and further has excellent heat resistance and solubility in a solvent or the like. It is also excellent in production stability of a composition or a film.
- indole compound (Q) according to this embodiment are shown below, but the present invention is not limited to the following examples.
- examples of the indole compound (Q) according to this embodiment include Exemplified Compound Nos. There can be mentioned 1 to 50 compounds. These indole compounds (Q) may be E-form or Z-form, or a mixture of E-form and Z-form.
- the indole compound (Q) according to the present embodiment has the above-described novel structure, it exhibits a shielding effect up to a long wavelength region with a wavelength of about 420 nm, and a shielding effect in a long wavelength ultraviolet region with a very small amount. Can be demonstrated.
- the indole compound (Q) according to this embodiment can also be produced by a normal condensation reaction.
- a so-called Kunefener gel condensation (knevenagel) condition (a method of condensing an aldehyde derivative and a compound represented by the general formula [IV] in a solvent such as toluene or ethanol using piperidine and / or acetic acid as a catalyst) ).
- Kunefener gel condensation a so-called Kunefener gel condensation (knevenagel) condition (a method of condensing an aldehyde derivative and a compound represented by the general formula [IV] in a solvent such as toluene or ethanol using piperidine and / or acetic acid as a catalyst) ).
- the method for producing an indole compound (Q) represented by the general formula [I] of the present embodiment includes the following steps: Step 1: A Vilsmeier reagent is reacted with a compound represented by the following general formula [II] A compound represented by the following general formula [III] is prepared. Step 2: The compound represented by the general formula [III] is reacted with the compound represented by the following general formula [IV].
- R 1 , R 2 , X 1 to X 4 are as defined in the general formula [I].
- R 1 , R 2 and X 1 to X 4 have the same meaning as in general formula [I].
- X ⁇ represents a halogen ion (fluorine ion, chlorine ion, iodine ion or bromine ion).
- a Vilsmeier reagent is prepared by, for example, reacting N, N-dimethylformamide with a halogenating agent such as phosphorus oxychloride, phosphorus oxybromide, oxalyl chloride, thionyl chloride, or benzoyl chloride.
- the preparation conditions are usually that the halogenating agent is added dropwise in the presence of N, N-formamide and, if necessary, a solvent (for example, a halogenated solvent such as dichloromethane or ethylene dichloride) under cooling at a temperature of about 0 to 5 ° C. After the reaction, the mixture is stirred for 30 minutes to 1 hour at room temperature. It is also possible to use a commercially available Vismeier reagent.
- the Vilsmeier reagent When reacting the Vilsmeier reagent with the compound represented by the general formula [II], the Vilsmeier reagent may be added to the compound represented by the general formula [II] and reacted. You may make it react by adding the compound represented by general formula [II] to the Meyer (Vilsmeier) reagent.
- the reaction temperature is usually cooled (for example, 0 ° C. to 20 ° C.), the Vilsmeier reagent is brought into contact with the general formula [II], and then the reaction is performed at room temperature to about 100 ° C.
- the reaction temperature is preferably 40 ° C to 80 ° C.
- the reaction time varies depending on the reaction temperature, but is usually about 30 minutes to 1 hour at 60 ° C.
- the amount of the Vilsmeier reagent used relative to the compound represented by the general formula [II] is usually 1 to 1.5 times equivalent, preferably 1 to 1.2 times equivalent.
- the compound represented by general formula [III] can be efficiently prepared.
- the compound represented by the general formula [III] can be obtained by cooling the reaction solution to room temperature.
- the compound represented by the general formula [III] can be taken out as a crystal by cooling the reaction solution (for example, 5 ° C. to ⁇ 10 ° C.), but it can be used in the next step without taking it out as it is. Good.
- the reaction of the compound represented by the general formula [III] and the compound represented by the general formula [IV] is usually represented by the general formula [IV] in the reaction solution in which the compound represented by the general formula [III] is produced.
- a base eg, an organic base such as triethylamine, diisopropylethylamine, pyridine, dimethylaminopyridine
- the reaction is carried out at room temperature to about 120 ° C, preferably 60 to 100 ° C.
- the reaction time varies depending on the reaction temperature, but is usually about 1 to 10 hours, preferably about 1 to 5 hours.
- the compound represented by the general formula [IV] can be reacted in an amount of 1.0 to 2.0 mol, preferably 1.0 to 1.5 mol, per 1 mol of the compound represented by the general formula [III]. .
- the amount of the base used is usually 1.0 to 4.0 mol, preferably 1.0 to 3.0 mol with respect to 1 mol of the compound represented by the general formula [III].
- water is added the hydrogen halide salt of the base produced in the reaction is removed by washing with water, the organic phase is concentrated, and then crystallized with a poor solvent (for example, methanol, ethanol, isopropanol, diethyl ether, diisopropyl ether).
- Indole compounds represented by the general formula [I] can be obtained.
- the hydrogen halide salt of the base is removed by filtration, and the organic solvent is concentrated, followed by crystallization with a poor solvent. Furthermore, it can be purified by column chromatography or the like.
- the layer (A) As a method for producing the layer (A) according to this embodiment, a conventionally known method can be used, and a coating method, a casting polymerization method, an injection molding method, an extrusion molding method, an insert molding, a compression molding method, a transfer molding. Method, press molding method, etc., and can be molded into a desired shape. Since the indole compound (Q) according to the present embodiment is excellent in heat resistance and solubility in a solvent, the production stability of the layer (A) and the like is also excellent.
- the composition (P) according to the present embodiment is a composition for forming a layer (A) located on the observation side of the light emitting element in a display device including the light emitting element, and is represented by the general formula [I]. It is preferable to further include at least one compound (R) selected from a resin and a polymerizable compound, including the indole compound (Q) shown.
- the content of the indole compound (Q) in the composition (P) according to the present embodiment is not particularly limited because it is appropriately adjusted according to the type of the layer (A) to which the composition (P) is applied.
- the content of the compound (R) contained in the composition (P) is 100 parts by mass, for example, 0.0001 parts by mass to 50 parts by mass, preferably 0.001 parts by mass to 20 parts by mass, It is 0.01 mass part or more and 10 mass parts or less.
- the compound (R) according to this embodiment is not particularly limited because it is appropriately selected according to the type of the layer (A) to which the composition (P) is applied.
- the composition (P) is selected from a sealing layer, a barrier layer, a touch panel layer, a planarizing layer, an overcoat layer, a color filter layer, a surface protective layer, an adhesive layer, an adhesive layer, a microlens, a polarizing plate, and the like.
- the content of the known resin, polymerizable compound and each component can be appropriately selected from each known technology with reference to the known technology of each layer.
- polymerizable compound examples include polyiso (thio) cyanate compounds, bifunctional or higher functional hydrogen compounds, and poly (meth) acrylic acid esters.
- the polyiso (thio) cyanate compound is a compound having two or more isocyanate groups or isothiocyanate groups.
- bifunctional or higher functional hydrogen compound examples include compounds having two or more functional groups selected from a hydroxy group, a mercapto group, and an amino group, such as ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, Bifunctional or more active hydrogen compounds having a hydroxy group such as glycerin, polyglycerin, thioglycerin; trithioglycerin, pentaerythritol tetrakis (thioglycolate), trimethylolpropane (3-mercaptopropionate), pentaerythritol tetrakis ( 3-mercaptopropionate), dipentaerythritol hexa (3-mercaptopropionate), bis (2-mercaptoethyl) sulfide, 4-mercaptomethyl-3,6-dithiaoct 1,8-dithiol, 4,8-bis (mercaptomethyl) -3,6,9-trithiaunde
- poly (meth) acrylic acid esters examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di ( (Meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, 1,4-butanediol di (meta) ) Acrylate, 1,6-hexanediol di (meth) acrylate, pentaerythritol di (meth) acrylate, glycerin di (meth) acrylate, and other aliphatic di (meth) acrylates; 2,2-bis [4- (meta ) Acryloyloxy Enyl] propane, 2,2-bis [4- (meth) acryloyloxyethoxyphen
- the polyfunctional (meth) acrylate etc. which were made are mentioned.
- thermosetting resin examples of the resin contained in the composition (P) according to the present embodiment include a thermosetting resin, a thermoplastic resin, and a photocurable resin.
- thermoplastic resin is not particularly limited.
- polyolefin resin polymethacrylic resin such as polymethyl methacrylate resin
- polyacrylic resin such as polymethyl acrylate resin
- polystyrene resin polyvinyl alcohol-polyvinyl chloride copolymer.
- Polymer resin polyvinyl acetal resin, polyvinyl butyral resin, polyvinyl formal resin, polymethylpentene resin, maleic anhydride-styrene copolymer resin, polycarbonate resin, polyphenylene ether resin, polyether ether ketone resin, polyether ketone resin, etc.
- Aromatic polyetherketone polyester resin, polyamide resin, polyamideimide resin, polyimide resin, polyetherimide resin, styrene elastomer, polyolefin elastomer Polyurethane elastomer, polyester elastomer, polyamide elastomer, ionomer, aminopolyacrylamide resin, isobutylene maleic anhydride copolymer, ABS, ACS, AES, AS, ASA, MBS, ethylene-vinyl chloride copolymer, ethylene-vinyl acetate copolymer, ethylene -Vinyl acetate-vinyl chloride graft polymer, ethylene-vinyl alcohol copolymer, chlorinated polyvinyl chloride resin, chlorinated polyethylene resin, chlorinated polypropylene resin, carboxyvinyl polymer, ketone resin, amorphous copolyester resin, norbornene resin, fluorine Plastic, polytetrafluoroethylene resin
- the curable resin is not particularly limited.
- examples thereof include saturated polyester resins, resins having (meth) acryloyloxy groups, preferably epoxy resins, oxetane compounds, resins having (meth) acryloyloxy groups, phenol resins and melamine resins, more preferably epoxy resins. is there.
- These curable resins may be used alone or in combination of two or more.
- the epoxy resin examples include bisphenol type epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, and bisphenol S type epoxy resin; novolak type epoxy resins such as phenol novolak type epoxy resin and cresol novolak type epoxy resin; Nitrogen-containing cyclic epoxy resins such as glycidyl isocyanurate type and hydantoin type; naphthalene type epoxy resin; biphenyl type epoxy resin; glycidyl ether type epoxy resin; dicyclo type epoxy resin; ester type epoxy resin; triphenylmethane type epoxy resin; Examples thereof include novolak-type epoxy resins; alicyclic epoxy resins (such as Daicel's ceroxide); and their modified or hydrogenated products.
- the oxetane compound include Aron Oxetane produced by Toa Gosei.
- phenol resin for example, a phenol novolak resin, a phenol aralkyl resin, a biphenyl aralkyl resin, a dicyclopentadiene type phenol resin, a cresol novolak resin, a resole resin, or the like is used.
- Examples of the resin having a (meth) acryloyloxy group include (meth) acrylic acid esters and those having a (meth) acryloyl group in the molecule by modifying a reactive functional group.
- (meth) acrylic acid esters are preferable from the viewpoint that polymerization or crosslinking proceeds rapidly with active radicals generated by irradiation with ultraviolet rays.
- (meth) acrylic acid means acrylic acid or methacrylic acid.
- Examples of the (meth) acrylic acid ester include an ester compound obtained by reacting a compound having a hydroxyl group with (meth) acrylic acid, and an epoxy obtained by reacting (meth) acrylic acid with an epoxy compound ( Examples thereof include urethane (meth) acrylates obtained by reacting (meth) acrylates and isocyanates with (meth) acrylic acid derivatives having a hydroxyl group.
- hardening agents such as a thermosetting agent, a thermal radical initiator, and a photoinitiator
- a thermosetting agent, a thermal radical initiator, and a photopolymerization initiator are not particularly limited.
- the photopolymerization initiator include polymerization initiators (UV radical initiator, UV cation initiator) that generate radicals or ions when irradiated with light such as ultraviolet rays.
- thermoplastic resins can be used individually by 1 type, respectively, and can also be used in combination of 2 or more type.
- thermoplastic resins, thermosetting resins, or photocurable resins are well known, such as “Practical Plastics Dictionary” (Edited by Practical Plastics Dictionary Editorial Board, published by Industrial Research Co., Ltd.) It is described in the publication.
- the “resin” here may be either soft or hard, and is not particularly limited.
- additives can be added to the composition (P) according to the present embodiment as desired.
- additives include organic fillers, inorganic fillers, catalysts, ultraviolet polymerization initiators, thermal polymerization initiators, internal mold release agents, curing agents, antistatic agents, and ultraviolet absorbers other than indole compounds (Q).
- UVA-A Exemplified Compound 14
- UVA-B Exemplified Compound 15
- UVA-C Exemplified Compound 16
- UVA-D Exemplified Compound 12 [9] Ultraviolet absorber-5 (hereinafter sometimes abbreviated as UVA-E): 2- (3
- Examples 15 to 17 and Comparative Examples 3 to 8 are as follows. (Light transmittance) Using a UV-visible spectrophotometer (UV-2550: manufactured by Shimadzu Corporation), the light transmittance of the obtained cured film was measured. For the transmittance, the transmittance in a wavelength range of 300 nm to 800 nm was measured, and evaluation was performed with light transmittances of 420 nm and 470 nm. [Measurement of full width at half maximum] A blue OLED element was prepared, SiN was deposited by CVD, and each composition shown in Table 2 (only Example 15, Comparative Examples 3 and 4) was applied thereon with a thickness of 20 ⁇ m, and cured at 100 ° C. for 30 minutes.
- the emission spectrum of each test piece was measured using an LED light measuring machine (manufactured by Hioki Electric Co., Ltd.). From the emission spectrum, the full width at half maximum at the maximum absorption peak wavelength of 450 nm was measured.
- the blue OLED element was produced according to the manufacture example 1 of the patent 3037610.
- Example 1 (Production of Exemplified Compound 14) Into a 1 L three-necked flask, 40.0 g of N, N-dimethylformamide and 130 g of 1,2-dichloroethane were inserted and cooled to 5 ° C. with an ice bath. Thereafter, 76.9 g of phosphorus oxychloride was added dropwise over 35 minutes, and the mixture was further stirred at room temperature for 25 minutes to prepare a Vilesmeier reagent. This solution was cooled to 5 ° C. with an ice bath, and 103.6 g of N-methyl-2-phenylindole was added in 10 portions over 30 minutes. Thereafter, the mixture was heated to 60 ° C.
- Example 2 (Production of Exemplified Compound 15)
- 4.00 g of N, N-dimethylformamide and 13 g of 1,2-dichloroethane were inserted, and cooled to 5 ° C. with an ice bath.
- 7.69 g of phosphorus oxychloride was added dropwise over 35 minutes, and the mixture was further stirred at room temperature for 25 minutes to prepare a Vilesmeier reagent.
- the solution was cooled to 5 ° C. with an ice bath and 10.36 g of N-methyl-2-phenylindole was added in 5 portions over 10 minutes. Thereafter, the mixture was heated to 60 ° C.
- Example 3 (Production of Exemplary Compound 16)
- Example 2 instead of using 10.58 g of ethyl 4,4,4-trifluoroacetoacetate, 9.90 g of benzyl acetoacetate was used in accordance with the procedure described in Example 2 (exemplary compound) 16) was obtained as pale yellow crystals (recrystallization was performed 4 times).
- the HPLC purity of this compound was 98.7 Area%, and the yield was 27%.
- the melting point was 133 ° C.
- a 1 H-NMR chart of this compound is shown in FIG. As apparent from the 1 H-NMR chart, this compound was a mixture of E-form and Z-form.
- Example 4 (Production of Exemplified Compound 12)
- Example 2 instead of using 10.58 g of ethyl 4,4,4-trifluoroacetoacetate, the reaction was carried out according to the procedure described in Example 2 except that 5.5 g of acetylacetone was used. Purification by chromatography (eluent: chloroform) gave 4.82 g of the desired product (Exemplary Compound 12) as pale yellow crystals. The HPLC purity of this compound was 99.2 Area%, and the yield was 30%. The melting point was 153 ° C. A 1 H-NMR chart of this compound is shown in FIG.
- Example 5 (Production of Exemplified Compound 17)
- Example 2 instead of using 10.58 g of ethyl 4,4,4-trifluoroacetoacetate, 8.1 g of diethyl malonate was used according to the procedure described in Example 2 (exemplary compound) 17) was obtained as pale yellow crystals.
- the HPLC purity of this compound was 99,0 Area%, and the yield was 66%.
- the melting point was 114 ° C.
- a 1 H-NMR chart of this compound is shown in FIG.
- Example 6 (Production of Exemplified Compound 41)
- Example 2 instead of using 10.36 g of N-methyl-2-phenylindole, according to the procedure described in Example 1, except that 13.47 g of N-phenyl-2-phenylindole was used, the target product was obtained. 4.17 g of (Exemplary Compound 41) was obtained as pale yellow crystals. The compound HPLC purity was 98.7 Area%, and the yield was 18%. The melting point was 103.5 ° C. A 1 H-NMR chart of this compound is shown in FIG.
- Example 7 Manufacture of resin composition
- foreign matter was filtered through a filter, and then discharged from the die in a strand shape (discharge amount: 10 kg / hr), water cooled and solidified, and then pelletized with a rotary cutter to obtain a polycarbonate resin composition.
- the polycarbonate resin composition was dried in a clean oven at 120 ° C. for 5 hours.
- Example 8 Manufacture of resin composition
- a polyamide resin composition was obtained according to the procedure described in Example 7 except that 100 parts by mass of polyamide resin-1 was used instead of 100 parts by mass of polycarbonate resin-1.
- Example 9 Manufacture of resin composition
- a polyester resin composition was obtained according to the procedure described in Example 7, except that 100 parts by mass of polyester resin-1 was used instead of 100 parts by mass of polycarbonate resin-1.
- Example 10 Manufacture of resin composition
- a polyester resin composition was obtained according to the procedure described in Example 7 except that 100 parts by mass of polyester resin-2 was used instead of 100 parts by mass of polycarbonate resin-1.
- Example 11 Manufacture of resin composition
- Example 7 instead of using 0.030 parts by mass (300 ppm) of UVA-A, 0.007 parts by mass (70 ppm) of UVA-B was used, and the polycarbonate resin was subjected to the operation described in Example 7. A composition was obtained.
- Example 12 Manufacture of resin composition
- polycarbonate resin was prepared according to the procedure described in Example 7 except that 0.030 parts by mass (300 ppm) of UVA-C was used. A composition was obtained.
- Example 13 Manufacture of resin composition
- a polycarbonate resin was prepared according to the procedure described in Example 7. A composition was obtained.
- Example 14 Manufacture of resin composition
- a polycarbonate resin composition was prepared according to the procedure described in Example 7 except that 0.02 part by mass of processing heat stabilizer A and 0.0005 part by mass (5 ppm) of blueing agent A were further blended. Got.
- Table 1 summarizes the optical properties of the resin compositions produced in Examples 7 to 14 and Comparative Examples 1 and 2.
- the resin composition using the indole compound (Q) represented by the general formula [I] has a spectral transmittance of 420 nm which is reduced even when the amount of the UV absorber added is small.
- the resin composition using the compound of this invention shows a low YI value in the same spectral transmittance from the comparison of Example 7 and Comparative Example 2.
- the above effect can be obtained even if the type of resin is changed.
- Examples 11 to 14 when the type of the UV absorber is changed or other additives are added. It was found that the above effect can be obtained even when added.
- the display device including the layer (A) using the indole-based compound (Q) represented by the general formula [I] is positioned closer to the observation side than the light-emitting element, and the indole-based compound (Q ) Containing layer (A) can effectively cut a region having a wavelength of 420 nm or less, that is, a purple region, and can improve blue color purity.
- Example 15 The resin composition obtained by the formulation shown in Table 2 was screen-printed on a non-alkali glass plate with a film thickness of 20 ⁇ m and thermally cured at 100 ° C. for 30 minutes to obtain a cured film.
- the light transmittance of 300 nm to 800 nm of the obtained cured film and the light transmittance of 300 nm to 800 nm (background data) of the alkali-free glass plate were measured.
- the background data was subtracted from the light transmittance data to calculate the light transmittance of the cured film.
- the half value width was measured by the above-mentioned method.
- the unit of numerical values in Table 2 is parts by mass.
- Example 16 The resin composition obtained with the formulation shown in Table 2 was coated on a PET film (Purex manufactured by Teijin DuPont, 38 ⁇ m) that had been mold-released using a coating machine so that the dry thickness was about 20 ⁇ m. And dried at 40 ° C. for 2 hours under vacuum to obtain a solid sheet in a normal temperature range (about 25 ° C.). Each sheet was sandwiched between release-treated PET films (Purex manufactured by Teijin DuPont, 38 ⁇ m), and then cured at 100 ° C. for 30 minutes to prepare a cured film. The light transmittance was measured with respect to the obtained cured film. The obtained results are shown in Table 2.
- Example 17 Each component was mixed with the formulation shown in Table 2 to obtain a resin composition.
- the resin composition was diluted with xylene and prepared as a varnish for the resin composition.
- the release film was peeled from the obtained resin layer, the resin layer was attached to a measuring jig, and the light transmittance was measured.
- Comparison between Example 15 and Comparative Examples 3 to 4, Comparison between Example 16 and Comparative Examples 5 to 6, and Comparison between Example 17 and Comparative Examples 7 to 8 indicates the above general formula [I]. It was found that the resin composition using the indole compound (Q) can reduce the light transmittance at 420 nm. Further, from the results of Examples 15 to 17, it was found that the above-described effect can be obtained even if the type of resin is changed. Further, in Examples 15 to 17, the light transmittance at 420 nm is very low, and the light transmittance at 470 nm is high, so that the improvement in blue purity can be reasonably understood.
- the display device including the layer (A) using the indole-based compound (Q) represented by the general formula [I] is positioned closer to the observation side than the light-emitting element, and the indole-based compound (Q ) Containing layer (A) can effectively cut a region having a wavelength of 420 nm or less, that is, a purple region, and can improve blue color purity.
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Abstract
Description
例えば特許文献1には、青色として優れた色純度を与える広いバンドギャップを有したベンゾ[b]ナフト[1,2-d]フラン化合物を含む発光素子が開示されている。
発光素子と、
上記発光素子よりも観察側に位置し、かつ、下記一般式[I]により示されるインドール系化合物を含む組成物により形成された1層以上の層(A)と、
を備える表示装置。
[2]
上記[1]に記載の表示装置において、
上記組成物は、樹脂および重合性化合物から選択される少なくとも一種の化合物をさらに含む表示装置。
[3]
上記[1]または[2]に記載の表示装置において、
有機EL表示装置または液晶表示装置である表示装置。
[4]
上記[1]乃至[3]のいずれか一つに記載の表示装置において、
上記層(A)が、封止層、バリア性層、タッチパネル層、平坦化層、オーバーコート層、カラーフィルター層、表面保護層、接着層、粘着性層、マイクロレンズおよび偏光板から選択される少なくとも1つの層を含む表示装置。
[5]
発光素子を備える表示装置における、上記発光素子よりも観察側に位置する層(A)を形成するための組成物であって、
下記一般式[I]により示されるインドール系化合物を含む表示装置用組成物。
[6]
上記[5]に記載の表示装置用組成物において、
樹脂および重合性化合物から選択される少なくとも一種の化合物をさらに含む表示装置用組成物。
[7]
上記[5]または[6]に記載の表示装置用組成物において、
上記表示装置が有機EL表示装置または液晶表示装置である表示装置用組成物。
[8]
上記[5]乃至[7]のいずれか一つに記載の表示装置用組成物において、
表示装置における、封止層、バリア性層、タッチパネル層、平坦化層、オーバーコート層、カラーフィルター層、表面保護層、マイクロレンズおよび偏光板から選択される少なくとも1つの層を形成するための組成物である表示装置用組成物。
本実施形態に係る表示装置は、発光素子と、発光素子よりも観察側に位置し、かつ、下記一般式[I]により示されるインドール系化合物(Q)を含む組成物(P)により形成された1層以上の層(A)と、を備える。
上記一般式[I]で表わされるインドール系化合物(Q)によれば、波長420nm程度の長波長領域まで優れた遮蔽効果を示す。そのため、発光素子よりも観察側に位置し、かつ、インドール系化合物(Q)を含む組成物(P)により形成された1層以上の層(A)を備えることによって、発光素子からの光が層(A)を透過した際に、インドール系化合物(Q)を含む層(A)によって、波長420nm以下の領域、すなわち紫の領域を効果的にカットすることができ、青色の色純度を向上させることができる。
また、インドール系化合物(Q)を含む層(A)は波長420nmを超える領域の吸収は少ないため、本実施形態に係る表示装置は全体の輝度を良好に保ちながら、青色の色純度を向上させることができる。
また、層(A)を機能から分類すると、例えば、封止層、バリア性層、タッチパネル層、平坦化層、オーバーコート層、カラーフィルター層、表面保護層、接着層、粘着性層、マイクロレンズおよび偏光板等から選択される一種または二種以上の層が挙げられる。
図1に示す表示装置100は、有機EL表示装置であり、発光素子10よりも観察側に位置する層として、バリア性層21(タッチパネル層21または表面保護層21であってもよい)、オーバーコート層22(封止層22またはバリア性層22であってもよい)、平坦化層23(封止層23であってもよい)、バリア性層24等を有している。これらの層のうち、1層以上にインドール系化合物(Q)が配合され、層(A)として機能することができる。
図1に示す表示装置100は、例えば、基材層50上に設けられた発光素子10と、発光素子10を覆うように基材層50上に設けられた平坦化層23と、平坦化層23の表面に設けられたバリア性層24と、平坦化層23およびバリア性層24を覆うように基材層50上に設けられたオーバーコート層22と、オーバーコート層22上に設けられたバリア性層21と、を備えている。
各層の具体的な構成は特に限定されず、一般的に公知の情報に基づいて、適切な構成をそれぞれ採用することができる。また、このような表示装置100は、一般的に公知の情報に基づいて、製造することが可能である。
図2に示す表示装置100は、有機EL表示装置であり、発光素子10よりも観察側に位置する層として、バリア性層21(タッチパネル層21または表面保護層21であってもよい)、カラーフィルター層25、封止層26、バリア性層24等を有している。これらの層のうち、1層以上にインドール系化合物(Q)が配合され、層(A)として機能することができる。
図2に示す表示装置100は、例えば、基材層50上に設けられた発光素子10と、発光素子10を覆うように設けられたバリア性層24と、発光素子10およびバリア性層24を覆うように基材層50上に設けられた封止層26と、封止層26上に設けられたカラーフィルター層25と、カラーフィルター層25上に設けられたバリア性層21(タッチパネル層21または表面保護層21であってもよい)と、基材層50上に発光素子10を配置するための中空部分を形成するためのダム材30と、を備えている。
各層の具体的な構成は特に限定されず、一般的に公知の情報に基づいて、適切な構成をそれぞれ採用することができる。また、このような表示装置100は、一般的に公知の情報に基づいて、製造することが可能である。
本実施形態に係るインドール系化合物(Q)は、下記一般式[I]で表わされる化合物である。
本実施形態において、本発明の効果の観点から、R1として炭素数1~12の直鎖または分岐のアルキル基、炭素数3~12の環状のアルキル基あるいは炭素数6~30の置換または非置換の芳香族基が好ましく、炭素数1~12の直鎖または分岐のアルキル基あるいは炭素数6~20の置換または非置換の芳香族基がより好ましく、炭素数1~6の直鎖または分岐のアルキル基あるいは炭素数6~20の置換または非置換の芳香族基がさらに好ましい。
「置換または非置換の芳香族基」はR1において例示された基と同様である。
ハロゲン原子としては、フッ素、塩素、ヨウ素および臭素を挙げることができる。
直鎖、分岐または環状のアルキル基は、R1において例示された基と同様である。
直鎖、分岐または環状のフルオロアルキル基は、R1で例示された直鎖、分岐または環状のアルキル基の1又は2以上の水素原子をフッ素原子で置換して得られる。
本実施形態に係るインドール系化合物(Q)は、通常の縮合反応によっても製造可能である。例えば、所謂、クネーフェナーゲル縮合(knevenagel)の条件(ピペリジンおよびまたは酢酸などを触媒としてトルエン、エタノール等の溶媒中で、アルデヒド誘導体と、一般式[IV]で表される化合物を縮合する方法)によっても製造可能である。ただし、通常の縮合反応条件では収率良く化合物が得られない場合が多く、本実施形態の製造法で製造することが好ましい。
工程1:フィルスマイヤー(Vilsmeier)試薬を下記一般式[II]で表わされる化合物に反応させ、下記一般式[III]で表わされる化合物を調製する。
工程2:一般式[III]で表わされる前記化合物と、下記一般式[IV]で表される化合物と、を反応させる。
フィルスマイヤー(Vilsmeier)試薬は、例えば、N,N-ジメチルホルムアミドと、オキシ塩化リン、オキシ臭化リン、オギザリルクロライド、塩化チオニル、塩化ベンゾイルなどのハロゲン化剤を作用させることにより調製する。調製条件は、通常冷却下にN,N-ホルムアミドおよび必要に応じて溶媒(例えばジクロロメタン、エチレンジクロライドなどのハロゲン化溶媒)の存在下に、ハロゲン化剤を滴下させて温度0~5℃程度で反応させ、その後、室温にて、30分から1時間程度攪拌させて調製を行う。また、市販のフィルスマイヤー(Vismeier)試薬を使用することも可能である。
反応後、反応液を室温に冷却することにより、一般式[III]で表わされる化合物を得ることができる。一般式[III]で表される化合物は反応液を冷却(例えば5℃~―10℃)することで結晶として取り出すことも可能であるが、そのまま取り出すことなく、次の工程で使用してもよい。
次いで、工程1で得られた一般式[III]で表わされる化合物と、一般式[IV]で表される化合物とを反応させる。
反応後水を添加して、反応で生成した塩基のハロゲン化水素塩を水洗により除去し、有機相を濃縮した後、貧溶媒(例えば、メタノール、エタノール、イソプロパノール、ジエチルエーテル、ジイソプロピルエーテル)により結晶化させ、一般式[I]で表わされるインドール系化合物を得ることができる。また、場合によっては、ろ過により塩基のハロゲン化水素塩を除去し、有機溶媒を濃縮した後に貧溶媒により結晶化させることも可能である。さらには、カラムクロマトグラフィー等により精製することも可能である。
本実施形態に係るインドール系化合物(Q)は耐熱性および溶媒に対する溶解性に優れることから、層(A)等の製造安定性にも優れる。
本実施形態に係る組成物(P)は発光素子を備える表示装置における、発光素子よりも観察側に位置する層(A)を形成するための組成物であって、上記一般式[I]により示されるインドール系化合物(Q)を含み、樹脂および重合性化合物から選択される少なくとも一種の化合物(R)をさらに含むことが好ましい。
本実施形態に係る組成物(P)中のインドール系化合物(Q)の含有量は組成物(P)が適用される層(A)の種類に応じて適宜調整されるため特に限定されないが、組成物(P)に含まれる化合物(R)の含有量を100質量部としたとき、例えば0.0001質量部以上50質量部以下、好ましくは0.001質量部以上20質量部以下であり、0.01質量部以上10質量部以下である。
例えば、組成物(P)を封止層、バリア性層、タッチパネル層、平坦化層、オーバーコート層、カラーフィルター層、表面保護層、接着層、粘着性層、マイクロレンズおよび偏光板等から選択される一種または二種以上の層に適用する場合は、各層の公知技術を参照し、各公知技術から公知の樹脂や重合性化合物および各成分の含有量を適宜選択することができる。
本実施形態に係る組成物(P)に含まれる重合性化合物としては、ポリイソ(チオ)シアネート化合物、二官能以上の活性水素化合物、ポリ(メタ)アクリル酸エステル類等を挙げることができる。
本実施形態に係る組成物(P)に含まれる樹脂としては、熱硬化性樹脂、熱可塑性樹脂、光硬化性樹脂等を挙げることができる。
オキセタン化合物としては、例えば東亜合成のアロンオキセタン等が挙げられる。
上記(メタ)アクリル酸エステルとしては、例えば、(メタ)アクリル酸に水酸基を有する化合物を反応させることにより得られるエステル化合物、(メタ)アクリル酸とエポキシ化合物とを反応させることにより得られるエポキシ(メタ)アクリレート、イソシアネートに水酸基を有する(メタ)アクリル酸誘導体を反応させることにより得られるウレタン(メタ)アクリレート等が挙げられる。
このような熱硬化剤、熱ラジカル開始剤、光重合開始剤としては特に限定されない。光重合開始剤としては、例えば、紫外線等の光が照射されることでラジカル又はイオンを生成する重合開始剤(UVラジカル開始剤、UVカチオン開始剤)が挙げられる。
これらの熱可塑性樹脂、熱硬化性樹脂または光硬化性樹脂についての定義、製法については、周知であり、たとえば「実用プラスチック事典」(実用プラスチック事典 編集委員会編、株式会社産業調査会発行)等の刊行物に記載されている。なおここでいう「樹脂」とは軟質、硬質いずれであってもよく、特に制限はない。
〔1〕ポリカーボネート樹脂-1:帝人株式会社製、パンライト L-1225Z100、ビスフェノールA型ポリカーボネート
〔2〕ポリアミド樹脂-1:アルケマ社製 RILSAN CLEAR G350
〔3〕ポリエステル樹脂-1:イーストマンケイミカル社製 トライタン TX2001
〔4〕ポリエスエル樹脂-2:三菱ガス化学社製 ALTESTER S4502
〔5〕紫外線吸収剤-1(以下、UVA-Aと略記する場合がある):例示化合物14
〔6〕紫外線吸収剤-2(以下、UVA-Bと略記する場合がある):例示化合物15
〔7〕紫外線吸収剤-3(以下、UVA-Cと略記する場合がある):例示化合物16
〔8〕紫外線吸収剤-4(以下、UVA-Dと略記する場合がある):例示化合物12
〔9〕紫外線吸収剤-5(以下、UVA-Eと略記する場合がある):2-(3-tert-ブチル-5-メチル-2-ヒドロキシフェニル)-5-クロロベンゾトリアゾール
〔10〕紫外線吸収剤-6(以下、UVA-Fと略記する場合がある):オリエント化学社製 BONASORB UA-3912 化合物名:Ethyl 2-cyano-3-(1-methyl-2-phenyl-1H-indol-3-yl)acrylate
〔11〕加工熱安定剤A:テトラキス(2,4-ジ-t-ブチルフェニル)-4,4’-ビフェニレンジホスホナイト:〔Hostanox P-EPQ〕
〔12〕ブルーイング剤A:1-ヒドロキシ-4-(p-トリルアミノ)アントラセン-9,10-ジオン〔マクロレックスバイオレットB〕
〔13〕エポキシ樹脂-1:ビスフェノールF型エポキシ樹脂:三菱化学社製YL983U
〔14〕エポキシ樹脂-2:ビスフェノールF型エポキシ樹脂:三菱化学社製JER4005
〔15〕スチレン系粘着剤組成物
〔16〕4級アンモニウム塩:King industry社製
〔17〕イミダゾール:四国化成社製2E4MZ
〔18〕シランカップリング剤:信越化学工業社製KBM-403
〔19〕メチルエチルケトン
〔20〕紫外線吸収剤-7:2-(5-クロロ-2-ベンゾトリアゾリル)-6-tert-ブチル-p-クレゾール 商品名チヌビン326:BASF社製
実施例7~14および比較例1~2でおこなった評価は以下のとおりである。
〔分光透過率の測定〕
樹脂組成物を2mm厚のシートにプレス成形し、(株)島津製作所社製、分光光度計 Multispecにより紫外・可視光スペクトルを測定した。
〔Y.I.値の測定〕
2mm厚のプレスシートを用いてスガ試験機株式会社製色彩色差計Cute-iにて測定した。
〔全光線透過率・Haze〕
2mm厚のプレスシートを用いて日本電色株式会社製NDH2000にてJIS K 7136に準拠して測定した。
〔光線透過率〕
紫外可視分光光度計(UV-2550:島津製作所製)を使用して、得られた硬化フィルムの光線透過率を測定した。透過率は、波長300nm~800nmの範囲における透過率を測定し、評価は420nmと470nmの光線透過率で行った。
〔半値幅の測定〕
青色OLED素子を作製し、SiNをCVD蒸着しその上から厚さ20μmで表2の各組成物(実施例15、比較例3および4のみ)を塗布し、100℃30分硬化させて試験片とした。LED光測定機(日置電機社製)を使用して各試験片の発光スペクトルを測定した。発光スペクトルから最大吸収ピーク波長450nmの半値幅を測定した。
ここで、青色OLED素子は、特許第3037610号の製造例1に従って作製した。
(例示化合物14の製造)
1Lの三口フラスコにN,N-ジメチルホルムアミド40.0gおよび1,2-ジクロロエタン130gを挿入し、氷浴により5℃に冷却した。その後オキシ塩化リン76.9gを35分かけて滴下し、さらに室温で25分攪拌してVilesmeier試薬を調製した。この溶液を氷浴により5℃に冷却し、N-メチル-2-フィェニルインドール103.6gを30分間かけて10回に分割して添加した。その後、60℃に加熱し、40分間加熱攪拌した後、再度氷浴により冷却し反応液の温度を5℃とした。ここに1,2-ジクロロエタン260gおよびアセト酢酸エチル67.0gを添加した後、トリエチルアミン152.5gを40分間かけて滴下した。その後、80℃に加熱して20分間加熱攪拌した後、100℃で二時間加熱攪拌した。反応混合物を冷却した後、水1Lおよびクロロホルム1Lに排出して激しく混合した後、水相を分離した。されに水洗を2回行い有機相を分離した後、減圧下でクロロホルムおよび1,2-ジクロロエタンを留去した。残渣にメタノール200gを添加した後、結晶化した固体をろ別し、エタノールから2回再結晶して目的物(例示化合物14)を淡黄色結晶として61.2g得た。
この化合物のHPLC純度は99.0Area%であり、収率は35%であった。
また融点は、143℃であった。
この化合物の1H-NMRチャートを図1に示す。1H-NMRチャートから明らかなように本化合物はE体およびZ体の混合物であった。
(例示化合物15の製造)
100mlの三口フラスコにN,N-ジメチルホルムアミド4.00gおよび1,2-ジクロロエタン13gを挿入し、氷浴により5℃に冷却した。その後オキシ塩化リン7.69gを35分かけて滴下し、さらに室温で25分攪拌してVilesmeier試薬を調製した。この溶液を氷浴により5℃に冷却し、N-メチル-2-フェニルインドール10.36gを10分間かけて5回に分割して添加した。その後、60℃に加熱し、40分間加熱攪拌した後、再度氷浴により冷却し反応液の温度を5℃とした。ここに1,2-ジクロロエタン26gおよび4,4,4-トリフルオロアセト酢酸エチル10.58gを添加した後、トリエチルアミン15.25gを40分間かけて滴下した。その後、80℃に加熱して20分間加熱攪拌した後、100℃で二時間加熱攪拌した。反応混合物を冷却した後、水100mlおよびクロロホルム100mlに排出して激しく混合した後、水相を分離した。されに水洗を2回行い有機相を分離した後、減圧下でクロロホルムおよび1,2-ジクロロエタンを留去した。残渣にメタノール20gを添加した後、結晶化した固体をろ別し、エタノールから2回再結晶して目的物(例示化合物15)を淡黄色結晶として13.58g得た。
この化合物のHPLC純度は99.0Area%であり、収率は68%であった。
また融点は、135℃であった。
この化合物の1H-NMRチャートを図2に示す。1H-NMRチャートから明らかなように本化合物はE体およびZ体の混合物であった。
(例示化合物16の製造)
実施例2において、4,4,4-トリフルオロアセト酢酸エチル10.58gを使用する代わりに、アセト酢酸ベンジル9.90gを使用した以外は、実施例2に記載の操作に従い目的物(例示化合物16)を淡黄色結晶として5.45g得た(再結晶は4回実施した)。
この化合物のHPLC純度は98.7Area%であり、収率は27%であった。
また、融点は133℃であった。
この化合物の1H-NMRチャートを図3に示す。1H-NMRチャートから明らかなように本化合物はE体およびZ体の混合物であった。
(例示化合物12の製造)
実施例2において、4,4,4-トリフルオロアセト酢酸エチル10.58gを使用する代わりに、アセチルアセトン5.5gを使用した以外は、実施例2に記載の操作に従い、反応を行いシリカゲルカラムクロマトグラフィー(溶出液:クロロホルム)により精製し、目的物(例示化合物12)を淡黄色結晶として4.82g得た。
この化合物のHPLC純度は99.2Area%であり、収率は30%であった。
また、融点は153℃であった。
この化合物の1H-NMRチャートを図4に示す。
(例示化合物17の製造)
実施例2において、4,4,4-トリフルオロアセト酢酸エチル10.58gを使用する代わりに、マロン酸ジエチル8.1gを使用した以外は、実施例2に記載の操作に従い目的物(例示化合物17)を淡黄色結晶として12.4g得た。
この化合物のHPLC純度は99,0Area%であり、収率は66%であった。
また、融点は114℃であった。
この化合物の1H-NMRチャートを図5に示す。
(例示化合物41の製造)
実施例2において、N-メチル-2-フェニルインドール10.36gを使用する代わりに、N-フェニル-2-フェニルインドール13.47gを使用した以外は、実施例1に記載の操作に従い、目的物(例示化合物41)を淡黄色結晶として4.17g得た。
この化合物HPLC純度は98.7Area%であり、収率は18%であった。
また、融点は103.5℃であった。
この化合物の1H-NMRチャートを図6に示す。
(樹脂組成物の製造)
ポリカーボネート樹脂-1を100質量部およびUVA-Aを0.030質量部(300ppm)を定量フィーダーによりベント付き2軸押し出し機〔(株)東芝機械製TEM-35、シリンダー設定温度290℃〕に供給し、フィルターを通して異物をろ過した後、ダイからストランド状に排出し(吐出量:10kg/hr)、水冷、固化させた後回転式カッターでペレット化しポリカーボネート樹脂組成物を得た。その後、該ポリカーボネート樹脂組成物をクリーンオーブンにて120℃で5時間乾燥させた。
(樹脂組成物の製造)
実施例7において、ポリカーボネート樹脂-1を100質量部使用する代わりに、ポリアミド樹脂-1を100質量部使用した以外は、実施例7に記載の操作に従い、ポリアミド樹脂組成物を得た。
(樹脂組成物の製造)
実施例7において、ポリカーボネート樹脂-1を100質量部使用する代わりに、ポリエステル樹脂-1を100質量部使用した以外は、実施例7に記載の操作に従い、ポリエステル樹脂組成物を得た。
(樹脂組成物の製造)
実施例7において、ポリカーボネート樹脂-1を100質量部使用する代わりに、ポリエステル樹脂-2を100質量部使用した以外は、実施例7に記載の操作に従い、ポリエステル樹脂組成物を得た。
(樹脂組成物の製造)
実施例7において、UVA-Aを0.030質量部(300ppm)使用する代わりに、UVA-Bを0.007質量部(70ppm)使用した以外は、実施例7に記載の操作に従い、ポリカーボネート樹脂組成物を得た。
(樹脂組成物の製造)
実施例7において、UVA-Aを0.030質量部(300ppm)使用する代わりに、UVA-Cを0.030質量部(300ppm)使用した以外は、実施例7に記載の操作に従い、ポリカーボネート樹脂組成物を得た。
(樹脂組成物の製造)
実施例7において、UVA-Aを0.030質量部(300ppm)使用する代わりに、UVA-Dを0.0030質量部(300ppm)使用した以外は、実施例7に記載の操作に従い、ポリカーボネート樹脂組成物を得た。
(樹脂組成物の製造)
実施例7において、さらに加工熱安定剤Aを0.02質量部およびブルーイング剤Aを0.0005質量部(5ppm)を配合した以外は、実施例7に記載の操作に従い、ポリカーボネート樹脂組成物を得た。
(樹脂組成物の製造)
ポリカーボネート樹脂-1を100質量部およびUVA-Eを2.4質量部(24000ppm)を定量フィーダーによりベント付き2軸押し出し機〔(株)東芝機械製TEM-35、シリンダー設定温度290℃〕に供給し、フィルターを通して異物をろ過した後、ダイからストランド状に排出し(吐出量:10kg/hr)、水冷、固化させた後回転式カッターでペレット化しポリカーボネート樹脂組成物を得た。その後、該ポリカーボネート樹脂組成物をクリーンオーブンにて120℃で5時間乾燥させた。
(樹脂組成物の製造)
比較例1においてUVA-Eを2.4質量部使用する代わりに、UVA-Fを0.055質量部(550ppm)使用した以外は、比較例1に記載の操作に従い、ポリカーボネート樹脂組成物を得た。
また、実施例7と比較例2の比較より本発明の化合物を使用した樹脂組成物は同じ分光透過率において、低いYI値を示すことがわかる。
さらに、実施例7~10の結果から、樹脂の種類を変更しても上記の効果が得られ、実施例11~14の結果から、紫外線吸収剤の種類を変更した場合や他の添加剤を添加した場合でも上記の効果が得られることがわかった。
これらの結果から、上記一般式[I]により示されるインドール系化合物(Q)を使用した層(A)を備える表示装置は、発光素子よりも観察側に位置し、かつ、インドール系化合物(Q)を含む層(A)によって、波長420nm以下の領域、すなわち紫の領域を効果的にカットすることができ、青色の色純度を向上できることが理解できる。
表2に示す処方で得られた樹脂組成物を、無アルカリガラス板に膜厚20μmでスクリーン印刷し、これを100℃で30分熱硬化させ、硬化フィルムを得た。得られた硬化フィルムの300nm~800nmの光線透過率と無アルカリガラス板の300nm~800nmの光線透過率(バックグラウンドデータ)を測定した。光線透過率データから、バックグラウンドデータを減算し、硬化フィルムの光線透過率を算出した。また、上記した方法により半値幅を測定した。
ここで、表2における数値の単位は質量部である。
表2に示す処方に変更した以外は実施例15と同様にして硬化フィルムを作製し、半値幅および光線透過率をそれぞれ測定した。得られた結果を表2にそれぞれ示す。
表2に示す処方で得られた樹脂組成物を、塗工機を用いて離型処理したPETフィルム(帝人デュポン社製ピューレックス、38μm)上に、乾燥厚みが約20μmになるように塗工し、真空下40℃で2時間乾燥させて常温域(約25℃)で固形のシートを得た。各シートを、離型処理したPETフィルム(帝人デュポン社製ピューレックス、38μm)で挟んだ後、100℃で30分間熱硬化して硬化フィルムを作製した。得られた硬化フィルムに対して、光線透過率を測定した。得られた結果を表2に示す。
表2に示す処方に変更した以外は実施例16と同様にして硬化フィルムを作製し、光線透過率をそれぞれ測定した。得られた結果を表2にそれぞれ示す。
表2に示す処方で各成分を混合して樹脂組成物を得た。なお、樹脂組成物は、キシレンにより希釈され、樹脂組成物のワニスとして調製した。樹脂組成物のワニスを塗工機によりPETフィルム(離型処理したPETフィルム(商品名:ピューレックスA53、帝人デュポンフィルム社製、厚さ38μm、ベースフィルム))上に塗工した後、窒素パージオーブンにて90℃5分間乾燥させて、厚さ20μmの樹脂層を形成した。得られた樹脂層から離型フィルムを剥離して、樹脂層を測定用治具に取り付け、光線透過率を測定した。
表2に示す処方に変更した以外は実施例17と同様にして硬化フィルムを作製し、光線透過率をそれぞれ測定した。得られた結果を表2にそれぞれ示す。
さらに、実施例15~17の結果から、樹脂の種類を変更しても上記の効果が得られることがわかった。
さらに、実施例15~17では、420nmの光線透過率が非常に低く、470nmの光線透過率が高いことから青色純度の向上が合理的に理解できる。
これらの結果から、上記一般式[I]により示されるインドール系化合物(Q)を使用した層(A)を備える表示装置は、発光素子よりも観察側に位置し、かつ、インドール系化合物(Q)を含む層(A)によって、波長420nm以下の領域、すなわち紫の領域を効果的にカットすることができ、青色の色純度を向上できることが理解できる。
Claims (8)
- 発光素子と、
前記発光素子よりも観察側に位置し、かつ、下記一般式[I]により示されるインドール系化合物を含む組成物により形成された1層以上の層(A)と、
を備える表示装置。
- 請求項1に記載の表示装置において、
前記組成物は、樹脂および重合性化合物から選択される少なくとも一種の化合物をさらに含む表示装置。 - 請求項1または2に記載の表示装置において、
有機EL表示装置または液晶表示装置である表示装置。 - 請求項1乃至3のいずれか一項に記載の表示装置において、
前記層(A)が、封止層、バリア性層、タッチパネル層、平坦化層、オーバーコート層、カラーフィルター層、表面保護層、接着層、粘着性層、マイクロレンズおよび偏光板から選択される少なくとも1つの層を含む表示装置。 - 発光素子を備える表示装置における、前記発光素子よりも観察側に位置する層(A)を形成するための組成物であって、
下記一般式[I]により示されるインドール系化合物を含む表示装置用組成物。
- 請求項5に記載の表示装置用組成物において、
樹脂および重合性化合物から選択される少なくとも一種の化合物をさらに含む表示装置用組成物。 - 請求項5または6に記載の表示装置用組成物において、
前記表示装置が有機EL表示装置または液晶表示装置である表示装置用組成物。 - 請求項5乃至7のいずれか一項に記載の表示装置用組成物において、
表示装置における、封止層、バリア性層、タッチパネル層、平坦化層、オーバーコート層、カラーフィルター層、表面保護層、接着層、粘着性層、マイクロレンズおよび偏光板から選択される少なくとも1つの層を形成するための組成物である表示装置用組成物。
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CN111019579A (zh) * | 2019-12-26 | 2020-04-17 | 苏州晶台光电有限公司 | 一种热致变色封装胶及其制备方法与应用 |
WO2021132235A1 (ja) * | 2019-12-26 | 2021-07-01 | 住友化学株式会社 | 粘着剤組成物 |
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