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WO2017222328A1 - Composition adhésive ayant une excellente fonction de blocage des rayons ultraviolets, feuille adhésive et dispositif d'affichage la comprenant - Google Patents

Composition adhésive ayant une excellente fonction de blocage des rayons ultraviolets, feuille adhésive et dispositif d'affichage la comprenant Download PDF

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Publication number
WO2017222328A1
WO2017222328A1 PCT/KR2017/006619 KR2017006619W WO2017222328A1 WO 2017222328 A1 WO2017222328 A1 WO 2017222328A1 KR 2017006619 W KR2017006619 W KR 2017006619W WO 2017222328 A1 WO2017222328 A1 WO 2017222328A1
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WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
formula
wavelength
light
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2017/006619
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English (en)
Korean (ko)
Inventor
김영일
이은미
최진연
이한별
박종진
정준호
김상현
김선정
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LMS Co Ltd
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LMS Co Ltd
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Filing date
Publication date
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Publication of WO2017222328A1 publication Critical patent/WO2017222328A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
    • G02B6/0001—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings specially adapted for lighting devices or systems
    • G02B6/0011—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings specially adapted for lighting devices or systems the light guides being planar or of plate-like form
    • G02B6/0013—Means for improving the coupling-in of light from the light source into the light guide
    • G02B6/0023—Means for improving the coupling-in of light from the light source into the light guide provided by one optical element, or plurality thereof, placed between the light guide and the light source, or around the light source
    • G02B6/0025—Diffusing sheet or layer; Prismatic sheet or layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition, a pressure-sensitive adhesive sheet and a display device including the same excellent in UV protection.
  • Such flat panel displays include display devices such as liquid crystal displays, plasma display panels, and organic light emitting devices.
  • the organic light emitting diode display has a wide viewing angle and a fast response speed, thereby enabling high quality display.
  • an organic light emitting display device having a microcavity structure may increase output efficiency by using a resonance effect of light between upper and lower electrodes, and may improve color purity of light.
  • the organic light emitting diode display includes a substrate, a transparent first electrode formed on the substrate, an organic layer formed on the first electrode, and a second electrode formed on the organic layer and having high reflectance.
  • the substrate uses a glass substrate or a plastic substrate.
  • the organic layer includes a hole injection layer, a hole transport layer, a light generating layer, a hole blocking layer, and an electron transport layer. That is, as the plurality of organic material layers are stacked between the first electrode and the second electrode, an organic light emitting display device having a multilayer structure is manufactured.
  • An object of the present invention is to provide a pressure-sensitive adhesive composition and pressure-sensitive adhesive sheet that effectively blocks the light in the ultraviolet region without inhibiting the transmittance and adhesion to the light in the visible region.
  • Another object of the present invention is to provide a display device including the adhesive composition or the adhesive sheet.
  • the present invention provides an adhesive sheet that satisfies the following conditions 1 and 2 in one embodiment.
  • Light transmittance for wavelengths up to 390 nm is 10% or less on average
  • Light transmittance for a wavelength of 405 nm is 30% or less
  • Light transmittance for 410 nm wavelength is less than 60%
  • the light transmittance over 430 nm wavelength is more than 85%.
  • the present invention is a binder resin; And it includes a light absorption dye dispersed in the binder resin, the light absorption dye provides a pressure-sensitive adhesive composition characterized in that represented by the following formula (1).
  • R 1 to R 3 are each independently represented by hydrogen, a cyano group, or the following Formula 2,
  • a 1 to a 5 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or a 6 to 18 carbon atoms.
  • R 4 is represented by the following formula (3),
  • a 6 in Formula 3 is hydrogen or an alkyl group having 1 to 18 carbon atoms.
  • At least one hydrogen of R 1 to R 4 of Formula 1 is each independently an alkenyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, having 2 to 20 carbon atoms Heteroaryl group, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms, alkoxycarbonyl group having 1 to 6 carbon atoms, halogen group, cyano group, nitro group, hydroxy group and carboxyl group Substituted or unsubstituted with one selected from:
  • the present invention provides a pressure-sensitive adhesive sheet formed of the pressure-sensitive adhesive composition described above.
  • the present invention provides a display device including a pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition described above.
  • a display panel; Polarizing film; And a light transmissive window layer wherein the polarizing film has a multilayer structure including a polarizer and includes a pressure-sensitive adhesive layer formed of the adhesive composition described above, wherein the pressure-sensitive adhesive layer may be positioned between the display panel and the polarizer. have.
  • the pressure-sensitive adhesive composition and / or pressure-sensitive adhesive sheet according to the present invention can effectively block the light in the wavelength range of 390 nm or less without lowering the light transmittance and the adhesive performance to the light in the visible light region, to various kinds of display devices Applicable
  • FIG. 1 is a schematic diagram showing a cross-sectional structure of an adhesive sheet according to an embodiment of the invention.
  • FIG. 2 is a schematic diagram showing a cross-sectional structure of an adhesive sheet according to another embodiment of the present invention.
  • 3 and 4 are each a schematic diagram showing a cross-sectional structure of the pressure-sensitive adhesive sheet with a release film according to an embodiment of the present invention.
  • 5 and 6 are schematic views showing a cross-sectional structure of a display device according to an embodiment of the present invention, respectively.
  • 7 and 8 are graphs measuring the light transmittance for each wavelength of the pressure-sensitive adhesive sheet according to the embodiment.
  • 9 and 10 are graphs measuring light transmittance for each wavelength of a sample according to Examples or Comparative Examples, respectively.
  • alkyl group means a substituent derived from a saturated hydrocarbon in a linear or branched form.
  • alkyl group for example, methyl group (ethyl group), ethyl group (ethyl group), n-propyl group (n-propyl group), isopropyl group (iso-propyl group), n-butyl group (n -butyl group, sec-butyl group, t-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group (1,1- dimethylpropyl group), 1,2-dimethylpropyl group (1,2-dimethylpropyl group), 2,2-dimethylpropyl group (2,2-dimethylpropyl group), 1-ethylpropyl group (1-ethylpropyl group), 2- 2-ethylpropyl group, n-hexyl group, 1-methyl-2-ethylpropyl group, 1-ethyl-2-methylpropyl group (1-ethyl-2-methylpropyl group (1-ethyl
  • alkyl group may have 1 to 20 carbon atoms, for example, 1 to 12 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms.
  • cycloalkyl group means a substituent derived from a monocyclic saturated hydrocarbon.
  • cycloalkyl group for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group ( cycloheptyl group), cyclooctyl group, and the like.
  • cycloalkyl group may have 3 to 20 carbon atoms, for example, 3 to 12 carbon atoms, or 3 to 6 carbon atoms.
  • aryl group means a monovalent substituent derived from an aromatic hydrocarbon.
  • the "aryl group” for example, a phenyl group (phenyl group), naphthyl group (naphthyl group), anthracenyl group (anthracenyl group), phenanthryl group naphthacenyl group (naphthacenyl group), pyrenyl group (pyrenyl group), tolyl group (tolyl group), biphenyl group (biphenyl group), terphenyl group (terphenyl group), chrycenyl group (chrycenyl group), spirobifluorenyl group (spirobifluorenyl group), fluoranthenyl group ( fluoranthenyl group, fluorenyl group, fluorenyl group, perylenyl group, indenyl group, azulenyl group, heptarenyl group, heptalenyl group, phenalenyl group And phenanthrenyl
  • the "aryl group” may have 6 to 30 carbon atoms, for example, 6 to 10 carbon atoms, 6 to 14 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.
  • heteroaryl group means "aromatic heterocycle” or “heterocyclic” derived from a monocyclic or condensed ring.
  • heteroaryl group is at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se) and silicon (Si) as a hetero atom, for example, one, two Dogs, three or four.
  • the "heteroaryl group” for example, pyrrolyl group (pyrrolyl group), pyridyl group (pyridyl group), pyridinyl group (pyridinyl group), pyridazinyl group, pyrimidinyl group (pyrimidinyl group) ), Pyrazinyl group, triazolyl group, tetrazolyl group, tetrazolyl group, benzotriazolyl group, pyrazolyl group, imidazolyl group ), Benzimidazolyl group (benzimidazolyl group), indolyl group (indolyl group), indolinyl group (indolinyl group), isoindolyl group, indolinzinyl group (indolizinyl group), purinyl group ), Inindazolyl group, quinolyl group, isoquinolinyl group, isoquinolinyl group, quinolizinyl
  • thiazolyl group (thiazolyl group), isothiazolyl group (isothiazolyl group), benzothiazolyl group (benzothiazolyl group), benzothiadiazolyl group (benzothiadiazolyl group), phenothia Phenothiazinyl group, isoxazolyl group, furazanyl group, furazanyl group, phenoxazinyl group, oxazolyl group, oxazolyl group, benzoxazolyl group, Oxadiazolyl group, pyrazoloxazolyl group, imidazothiazolyl group, thienofuranyl group, furopyrrolyl group, pyridoxazinyl group and compounds containing at least two heteroatoms such as (pyridoxazinyl group).
  • heteroaryl group may have 2 to 20 carbon atoms, for example, 4 to 19 carbon atoms, 4 to 15 carbon atoms, or 5 to 11 carbon atoms.
  • the heteroaryl group may have a ring member of 5 to 21.
  • aralkyl group means a saturated hydrocarbon substituent having a monovalent substituent derived from an aromatic hydrocarbon at the hydrogen site of the terminal hydrocarbon. That is, the “aralkyl group” refers to an alkyl group in which the chain terminal is substituted with an aryl group, and examples thereof include a benzyl group, a phenethyl group, a phenylpropyl group, and a naphthalenylmethyl group. ) And a naphthalenylethyl group.
  • adheresion refers to a case where there is adhesiveness with an adjacent substrate, and includes both cases of adhesion or adhesion depending on the degree of adhesion.
  • the present invention provides an adhesive sheet that satisfies the following conditions 1 and 2.
  • Light transmittance for wavelengths up to 390 nm is 10% or less on average
  • Light transmittance for a wavelength of 405 nm is 30% or less
  • Light transmittance for 410 nm wavelength is less than 60%
  • the light transmittance over 430 nm wavelength is over 85%.
  • the pressure sensitive adhesive sheet according to the present invention may have a structure including a light absorbing dye.
  • the pressure-sensitive adhesive sheet according to the present invention a resin matrix; And a light absorbing dye dispersed in the resin matrix.
  • the pressure-sensitive adhesive sheet may satisfy the following condition 3.
  • T 30% represents the wavelength value at the point where the light transmittance is 30% in the 390-430 nm wavelength region
  • T 50% represents the wavelength value at the point where the light transmittance is 50% in the 390-430 nm wavelength region.
  • the pressure sensitive adhesive sheet according to the present invention effectively blocks light in a wavelength region of 410 nm or less. Through this, by applying the adhesive sheet to the display device, it is possible to prevent or reduce the change in color temperature due to discoloration or color coordinate shift due to ultraviolet irradiation when exposed to sunlight.
  • the pressure-sensitive adhesive sheet may satisfy the following conditions 4 and 5.
  • Light transmittance for wavelengths up to 390 nm is 5% or less on average
  • Light transmittance for a wavelength of 405 nm is 20% or less
  • the light transmittance for the 430 nm wavelength is greater than 90%.
  • the pressure-sensitive adhesive sheet may further satisfy the following condition 6.
  • T 30% represents the wavelength value at the point where the light transmittance is 30% in the 390 to 430 nm wavelength region
  • T 50% represents the wavelength value at the point where the light transmittance is 50% in the 390 to 430 nm wavelength region.
  • the adhesive sheet according to the present invention can be seen that the slope of the light absorption spectrum is very steep in the wavelength region 390 to 430 nm through the above condition 6. Through this, it can be seen that the light in the wavelength region of less than 390 nm is effectively blocked while at the same time does not inhibit the transmission of light in the wavelength region of more than 430 nm.
  • the thickness of the adhesive sheet is not particularly limited as long as it is a range applicable to the display device, but may be in the range of 10 to 50 ⁇ m on average. Specifically, the thickness of the adhesive sheet may range from 10 to 30 ⁇ m, 20 to 50 ⁇ m, 10 to 20 ⁇ m, or 13 to 17 ⁇ m on average. By adjusting the thickness of the pressure sensitive adhesive sheet in the above range, it is possible to achieve excellent adhesive force and ultraviolet ray blocking effect without greatly increasing the volume of the apparatus.
  • the adhesive sheet which concerns on this invention includes all the cases where the adhesive composition is manufactured in the form of a film, or is apply
  • the adhesive sheet may further include a release film formed on one or both sides of the adhesive sheet. This is for ease of transport, ease of movement in each step of the process.
  • the adhesive sheet may further include an optical film.
  • the optical film includes the case of a polarizing film.
  • such an adhesive sheet can be applied to various types of display devices.
  • the adhesive sheet including the optical film includes a case where the adhesive sheet is formed on one side or both sides of the polarizing film, and / or the adhesive sheet is formed on the inner interface of the polarizing film.
  • the adhesive sheet including the optical film may satisfy the following conditions 7 and 8.
  • Light transmittance for wavelengths up to 390 nm is 5% or less on average
  • Light transmission for 405 nm wavelength is less than 20%
  • the light transmittance for the 410 nm wavelength is 30% or less.
  • the adhesive sheet containing the optical film according to the present invention can effectively block light having a wavelength of 390 nm to 410 nm.
  • the light transmittance for the 390 nm wavelength may be on average 5% or less, 3% or less, 1.5% or less, or 0.01 to 5% range.
  • the adhesive sheet including the optical film according to the present invention substantially blocks light of the wavelength close to 100%.
  • the light transmittance for the 410 nm wavelength may be in the range of 30% or less, 25% or less, 15% or less, 5% or less, or 0.01 to 20%.
  • the adhesive sheet according to the present invention may further include the particulate component described above.
  • the pressure-sensitive adhesive layer further includes a particulate component having an average refractive index of 1.3 to 2.1.
  • the polarizing film may have a laminated structure including a polarizer and a retardation film.
  • the polarizing film may include the adhesive layer or the adhesive sheet described above between the polarizer and the retardation film.
  • the polarizer may be, for example, a TAC / PVA / TAC structure.
  • the retardation film may be a structure formed of PC or COP.
  • the retardation film may be a ⁇ / 4 retardation film.
  • the pressure-sensitive adhesive sheet containing the optical film may satisfy the following condition 9.
  • T 20% represents the wavelength value at the point where the light transmittance is 20% in the wavelength region of 390 to 430 nm
  • T 5% represents the wavelength value at the point where the light transmittance is 5% in the wavelength region of 390 to 430 nm.
  • the difference between T 20% and T 5% described in Condition 9 may be 15 nm or less, 10 nm or less, 7 nm or less, or 1 to 15 nm.
  • the adhesive sheet including the optical film according to the present invention can selectively block light in the ultraviolet region by adding an appropriate amount of a specific light absorbing dye.
  • the light absorbing dye is represented by the following Chemical Formula 1-a.
  • R 1 to R 3 are each independently represented by hydrogen, a cyano group, or the following Formula 2,
  • a 1 to a 5 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or 6 carbon atoms.
  • R 4 is represented by the following formula 3-b,
  • a 6 is hydrogen or an alkyl group having 1 to 18 carbon atoms.
  • One or more hydrogen of R 1 to R 4 of Formula 1-a are each independently an alkenyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 2 to 20 carbon atoms. Heteroaryl group having 6 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, alkoxycarbonyl group having 1 to 6 carbon atoms, halogen group, cyano group, nitro group, hydroxy group and carboxyl group Substituted or unsubstituted with one selected from the group consisting of.
  • the structure of the light absorbing dye represented by Chemical Formula 1-a is the same as the following Chemical Formula 1 and will be described later in Chemical Formula 1 below.
  • the adhesive sheet including the optical film according to the present invention can minimize color temperature changes due to exposure to sunlight. Specifically, the experiment to repeat the process of exposing the pressure-sensitive adhesive sheet containing the optical film 8 hours under sunlight irradiation conditions 8 hours under sunlight blocking conditions 10 times, the color temperature before the experiment (T 0 ) And after the experiment to calculate the difference between the color temperature (T 1 ).
  • the pressure-sensitive adhesive sheet containing the optical film satisfies the following condition 10 during a color temperature change experiment.
  • T 0 represents an average color temperature value of the sample measured before the photoexposure experiment
  • T 1 represents an average color temperature value of the sample measured after the photoexposure experiment
  • the photovoltaic exposure experiment the photovoltaic After 8 hours of exposure under irradiation conditions and 8 hours of exposure under sunlight conditions, the experiment was repeated 10 times and the average color temperature measured was shown.
  • the change in color temperature according to condition 10 is 200 K or less, specifically, 15 to 180 K.
  • the color temperature change amount of the sample according to the experiment may be 180 or less, 120 K or less, 50 K or less, or 1 to 200 K.
  • the present invention provides an adhesive composition, in one embodiment, the adhesive composition is a binder resin; And a light absorbing dye dispersed in the binder resin.
  • the pressure-sensitive adhesive composition according to the present invention can be formulated in the form of the pressure-sensitive adhesive sheet described above.
  • the light absorbing dye may be represented by the following formula (1).
  • R 1 to R 3 are each independently hydrogen, cyano group or represented by the following formula (2),
  • a 1 to a 5 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or 6 to 18 carbon atoms.
  • R 4 is represented by the following formula (3),
  • a 6 is hydrogen or an alkyl group having 1 to 18 carbon atoms.
  • At least one hydrogen of R 1 to R 4 of Formula 1 is each independently an alkenyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, having 2 to 20 carbon atoms Heteroaryl group, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms, alkoxycarbonyl group having 1 to 6 carbon atoms, halogen group, cyano group, nitro group, hydroxy group and carboxyl group Substituted or unsubstituted with one selected from:
  • the compound represented by Chemical Formula 1 may be specifically, represented by the following Chemical Formula 4.
  • Ra is a formula 2-a
  • R 2 is a cyano group
  • R 3 is hydrogen
  • a 1 to a 5 each independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or 6 carbon atoms.
  • Rb is represented by the following formula 3-a,
  • a 6 in formula 3-a is hydrogen or an alkyl group having 1 to 10 carbon atoms.
  • One or more hydrogen of R 2 , R 3 , Ra and Rb of Formula 4 may be independently an alkenyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 2 carbon atoms. Heteroaryl group having 20 to 20, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms, alkoxycarbonyl group having 1 to 6 carbon atoms, halogen group, cyano group, nitro group, hydroxy group and It is unsubstituted or substituted with one selected from the group consisting of carboxyl groups.
  • R 1 to R 4 of the compound represented by Chemical Formula 1 include the following Table 1 and Table 2.
  • the adhesive composition according to the present invention based on 100 parts by weight of the binder resin, the content of the light absorbing dye dispersed in the binder resin may be 40 parts by weight or less.
  • the content of the light absorbing dye may be in the range of 5 to 35 parts by weight, 7 to 35 parts by weight, 7 to 25 parts by weight, or 9 to 23 parts by weight.
  • the light in the wavelength region of less than 410 nm can be effectively blocked without inhibiting the transmittance of light in the wavelength region of more than 430 nm.
  • the pressure-sensitive adhesive composition according to the present invention when produced in the pressure-sensitive adhesive sheet, the light having a wavelength of 390 nm or less transmittance level of 10% or less, the light of 405 nm wavelength transmittance of 30% or less, specifically, light of 410 nm wavelength While blocking to below 60%, light of 430 nm wavelength can transmit more than 85%.
  • the pressure-sensitive adhesive composition according to the present invention may further include a particulate component dispersed in the binder resin.
  • the particulate component may have an average refractive index in the range of 1.3 to 2.1, or 1.4 to 1.6.
  • the particulate component is not particularly limited as long as it has the refractive index, and may include, for example, at least one metal particle selected from the group consisting of metal oxides, metal nitrides, and metal oxynitrides; At least one organic particle selected from the group consisting of silicone and acrylic resins; And organic-inorganic particles containing the components constituting the metal particles and the components constituting the organic particles.
  • the metal particles may be any one of Zr, Al, Fe, Cu, Ti, Au, Ag, Mg and Zn, or a mixture or alloy phase of two or more thereof, and may be used to convert oxides, nitrides and / or oxynitrides of the metals.
  • the organic particles may be silicon particles or acrylic resin particles in the form of beads.
  • organic-inorganic particles containing the components constituting the metal particles and the components constituting the organic particles are not excluded.
  • the particulate component may be at least one of ZrO 2 , TiO 2 , Al 2 O 3 , MgO, and SiO 2 , and the shape of the particles may be spherical or various polygonal.
  • the particulate component may have an average particle diameter of 0.1 to 5 ⁇ m, 0.5 to 3 ⁇ m, 3 to 5 ⁇ m, or 2 to 4 ⁇ m.
  • the average particle diameter of the said particulate component considers whether refractive index value or the transmittance
  • Including the particulate component having an average particle diameter in the above range can maximize the scattering effect (Mie Scattering) effect and forward scattering, thereby reducing the light linearity of a specific wavelength can be color according to the viewing angle This color shift phenomenon that appears distorted can be reduced.
  • the refractive index difference between the particulate component and the binder resin may be 0.05 or more.
  • the refractive index difference between the particulate component and the binder resin may be in the range of 0.05 to 0.4, 0.07 to 0.3, or 0.08 to 0.15.
  • the binder resin included in the adhesive composition according to the present invention is not particularly limited as long as it is an adhesive resin, and examples thereof include acrylic resins, rubber resins, vinyl resins, silicone resins, polyester resins, polyamide resins, urethane resins, fluorine resins, Epoxy resin or the said resin can be used in mixture of 2 or more types. Among them, acrylic resins can be used in terms of weather resistance, cost, and shape freedom of the pressure-sensitive adhesive.
  • the present invention provides a display device including a pressure-sensitive adhesive layer or a pressure-sensitive adhesive sheet formed of the pressure-sensitive adhesive composition described above.
  • the display device a display panel; Polarizing film; And a structure in which light-transmitting window layers are sequentially stacked, wherein the adhesive layer or the adhesive sheet is between the display panel and the polarizing film; Inside a polarizing film; And a structure formed at any one or more positions between the polarizing film and the transparent window layer.
  • the display apparatus may include a display panel; Polarizing film; And a light-transmitting window layer sequentially stacked, and the polarizing film may have a multilayer structure including a polarizer, and the adhesive layer or the adhesive sheet may be a structure formed near a display panel based on the polarizer.
  • the polarizing film may have a multilayer structure including a polarizer and a retardation film.
  • the pressure-sensitive adhesive layer or pressure-sensitive adhesive sheet can be formed at a position close to the display panel on the basis of the polarizer, so that light in the ultraviolet region can be efficiently blocked without affecting the performance of the display device.
  • a position close to the display panel with respect to the polarizer means between the polarizer and the display panel.
  • the pressure-sensitive adhesive layer or pressure-sensitive adhesive sheet is located between the display panel and the polarizer. Specifically, when several optical layers exist between the display panel and the polarizer, the pressure-sensitive adhesive layer or the pressure-sensitive adhesive sheet may be located at any one or more of interfaces between the layers. .
  • the display device may be, for example, an OLED device.
  • OLED organic light-emitting diode
  • the display device according to the present invention can selectively block the light in the ultraviolet region, and can effectively prevent discoloration or color temperature change due to sunlight exposure.
  • the display device may be applied to various types of display devices, and may be applied to, for example, a TV, a monitor, a mobile phone, a navigation, a notebook, or a tablet PC, and specifically, may be applied to a mobile device.
  • the display device according to the present invention encompasses all cases including a pressure-sensitive adhesive layer, a pressure-sensitive adhesive sheet or a laminated structure formed of the pressure-sensitive adhesive composition described above.
  • 1 is a structure in which the light absorbing dye 12 is dispersed in the binder resin 11 in the adhesive sheet 10 according to the exemplary embodiment of the present invention.
  • 2 is a pressure-sensitive adhesive sheet 20 according to another embodiment of the present invention, in which the light absorbing dye 22 and the particulate component 23 are dispersed together in the binder resin 21.
  • FIG. 3 illustrates a laminated structure of an adhesive sheet according to an embodiment of the present invention, in which a release film 30 is laminated on one surface of the adhesive sheet 10 in which a light absorbing dye is dispersed.
  • a release film 30 is laminated on one surface of the adhesive sheet 10 in which a light absorbing dye is dispersed.
  • Figure 4 also includes a structure in which the release film (31, 32) is laminated on both sides of the adhesive sheet (10).
  • the release film 30, 31, 32 formed on one or both sides of the adhesive sheet 10 can be removed according to the process step.
  • the display apparatus 100 has a structure in which the polarizing film 120, the adhesive layer 130, and the window layer 140 are sequentially stacked on the OLED panel 110.
  • the adhesive layer 130 has a structure in which a light absorbing dye is dispersed therein, and although not separately indicated, the adhesive layer 130 may have a structure in which particulate components are dispersed together.
  • FIG. 6 is a schematic view showing a cross-sectional structure of a display apparatus 100 according to another embodiment of the present invention.
  • the display device 200 has a structure in which a first adhesive layer 221, a polarizing film, a third adhesive layer 230, and a window layer 240 are sequentially stacked on the OLED panel 210.
  • the window layer 240 may use a light transmissive plastic or glass substrate.
  • the polarizing film has a structure in which the retardation film 222, the second adhesive layer 223, and the polarizer 224 are sequentially stacked.
  • the display apparatus 200 illustrated in FIG. 4 may include a first adhesive layer 221 formed between the OLED panel 210 and the retardation film 222; A second adhesive layer 223 formed between the retardation film 222 and the polarizer 224; And a third adhesive layer 230 formed between the polarizer 224 and the window layer 240, wherein at least one of the first to third adhesive layers 221, 223, and 230 is light dispersed therein. Absorbing dyes.
  • any one of the first to third adhesive layers 221, 223, 230 may include a light absorbing dye, or both or three layers may include a light absorbing dye. Can be.
  • the light absorbing dye was dispersed in the binder resin to prepare an adhesive composition.
  • an adhesive composition was prepared while gradually increasing the content of the light absorbing dye from Example 1 to Example 4.
  • the prepared pressure-sensitive adhesive composition was applied on a transparent substrate to prepare a pressure-sensitive adhesive sheet having a thickness of 15 ⁇ m.
  • a pressure-sensitive adhesive sheet was prepared in the same manner as in Example 1 except that no light absorbing dye was added.
  • permeability with respect to the light of the 380-780 nm wavelength range was measured.
  • the measured result is shown in FIG. Referring to FIG. 7, the adhesive film according to the present invention exhibits a transmittance close to 100% at a wavelength of 440 to 660 nm, which is a light emitting wavelength region of the OLED device. Through this, it can be seen that the adhesive sheet according to the present invention substantially blocks 100% of light having a wavelength of 390 nm or less without inhibiting the light emission wavelength transmittance of the display device.
  • the transmittance of light in the wavelength region of 380 to 450 nm is as shown in FIG.
  • the results of measuring the light transmittance (unit:%) for each wavelength for each example are shown in Table 3 below.
  • the adhesive sheet according to Examples 1 to 4 blocks more than 99% of light at a wavelength of 390 nm or less, it can be seen that the light transmittance of 20% or less at a wavelength of 405 nm.
  • stacked on the adhesive sheet which concerns on the comparative example 1 between a polarizer and retardation film, and between a polarizing film and an OLED panel was produced.
  • the adhesive film according to the present invention substantially blocks 100% of light below the wavelength of 390 nm without decreasing transmittance of light in the wavelength range of 440 nm to 660 nm, which is the light emission wavelength region of the OLED device. Can be.
  • the transmittance of light in the wavelength region of 380 to 450 nm is as shown in FIG.
  • the results of measuring the light transmittance (unit:%) for each wavelength for each example are shown in Table 4 below.
  • the samples according to Examples 5 to 8 block more than 99% of light at a wavelength of 390 nm, it can be seen that the light transmittance of 10% or less at 405 nm wavelength.
  • the samples of Examples 5 to 8 are very selective and effectively block the light in the wavelength region of 410 nm or less without inhibiting the light transmittance for light in the wavelength region of 430 nm or more It can be seen.
  • Example 1 100% 0.0003 0.0005
  • Example 2 100% 0.0004 0.0005
  • Example 3 100% 0.0005 0.0006
  • Example 4 100% 0.0009 0.0012 Comparative Example 1 100% 0.0000 0.0000
  • Comparative Example 1 and Examples 1 to 4 have no substantial difference.
  • Example 7 For samples prepared in Example 7 and Comparative Example 2, the amount of change in luminance and color coordinates was measured. In the experiment, each sample was exposed to light for 8 hours while the lamp was turned on, and then the procedure was repeated 10 times for 8 hours with the lamp turned off.
  • the sample according to Comparative Example 2 was found to have a color temperature change amount of 540 (K), but the sample according to Example 7 was found to have a color temperature change amount of 160 (K). Through this, it can be seen that the sample according to the present invention has a color temperature change amount of 30% or less under the same conditions as compared with the existing sample.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)

Abstract

L'invention concerne : une composition adhésive comprenant une résine liante et un colorant absorbant la lumière dispersé dans la résine liante ; et une feuille adhésive. De plus, la lumière dans la plage de longueurs d'onde de 390 nm ou moins peut être efficacement bloquée sans détériorer la transmittance de la lumière dans le domaine du visible ni la performance d'adhérence, et l'application de l'invention à divers types de dispositifs d'affichage est possible.
PCT/KR2017/006619 2016-06-23 2017-06-23 Composition adhésive ayant une excellente fonction de blocage des rayons ultraviolets, feuille adhésive et dispositif d'affichage la comprenant Ceased WO2017222328A1 (fr)

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KR1020160078498A KR101766284B1 (ko) 2016-06-23 2016-06-23 자외선 차단 기능이 우수한 점착 조성물, 점착 시트 및 이를 포함하는 디스플레이 장치
KR10-2016-0078498 2016-06-23

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WO2020111821A1 (fr) * 2018-11-30 2020-06-04 주식회사 엘지화학 Composition de revêtement
CN111542577A (zh) * 2017-12-29 2020-08-14 株式会社Lms 包含两种以上染料的粘结组合物、粘结片及包含其的显示装置
US20210040460A1 (en) 2012-04-27 2021-02-11 Duke University Genetic correction of mutated genes
CN113474307A (zh) * 2019-02-28 2021-10-01 Ａｇｃ株式会社 带胶粘层的光学构件和发光装置
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US12215345B2 (en) 2013-03-19 2025-02-04 Duke University Compositions and methods for the induction and tuning of gene expression

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US12215345B2 (en) 2013-03-19 2025-02-04 Duke University Compositions and methods for the induction and tuning of gene expression
US11479697B2 (en) * 2017-09-01 2022-10-25 Lms Co., Ltd. Adhesive sheet having excellent ultraviolet blocking function, adhesive composition, and display device comprising same
CN111542577B (zh) * 2017-12-29 2022-03-04 株式会社Lms 包含两种以上染料的粘结组合物、粘结片及包含其的显示装置
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WO2020111821A1 (fr) * 2018-11-30 2020-06-04 주식회사 엘지화학 Composition de revêtement
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CN113474307A (zh) * 2019-02-28 2021-10-01 Ａｇｃ株式会社 带胶粘层的光学构件和发光装置

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