WO2016003156A1 - Composition durcissable - Google Patents

Composition durcissable Download PDF

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Publication number
WO2016003156A1
WO2016003156A1 PCT/KR2015/006699 KR2015006699W WO2016003156A1 WO 2016003156 A1 WO2016003156 A1 WO 2016003156A1 KR 2015006699 W KR2015006699 W KR 2015006699W WO 2016003156 A1 WO2016003156 A1 WO 2016003156A1
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WIPO (PCT)
Prior art keywords
meth
curable composition
acrylate
oligomer
curing
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PCT/KR2015/006699
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English (en)
Korean (ko)
Inventor
우동현
양세우
이명한
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LG Chem Ltd
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LG Chem Ltd
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Priority to US15/106,997 priority Critical patent/US10221340B2/en
Priority to CN201580005947.4A priority patent/CN105934450B/zh
Priority claimed from KR1020150093073A external-priority patent/KR101703431B1/ko
Publication of WO2016003156A1 publication Critical patent/WO2016003156A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers

Definitions

  • the present application relates to a curable composition, a cured body and the use of the curable composition and the cured body.
  • the display device may include a touch panel 302 mounted on the display panel 301.
  • an air gap 304 may be formed between the display panel and the touch panel by interposing a spacer 303 between the display panel and the touch panel.
  • light scattering occurs due to the air gap existing between the display panel and the touch panel, and the contrast decreases due to the air gap, and the presence of the air gap hinders the thinning of the panel.
  • Patent Document 1 Japanese Patent Laid-Open No. 2005-55641
  • OCR Optically Clear Resin
  • the physical properties required for such OCR include optical properties, shrinkage, dielectric constant, crosslinking degree, adhesive properties, and the like.
  • to show excellent adhesion properties proper correlation between the properties of OCR is required.
  • research on each property has been actively conducted.
  • the results of researches on the parameters formulating the correlation between properties are insignificant. to be.
  • the present application provides a curable composition, a cured body and the use of the curable composition and the cured body.
  • the present application relates to a curable composition.
  • Applicants have found that by adjusting the correlation between dielectric constant, gel fraction, shrinkage and storage modulus, it is possible to provide a curable composition that can be suitably used in physical properties suitable for optical applications, such as so-called OCR (Optically Clear Resin). It confirmed and completed this invention.
  • OCR Optically Clear Resin
  • the correlation may be satisfied by adjusting the content ratio and the components included in the curable composition as described below.
  • the curable composition satisfies the above correlation, a cured product having low dielectric constant and excellent adhesive properties can be produced.
  • Exemplary curable compositions can satisfy, for example, the relationship of the following formula (1).
  • A is the dielectric constant at 1 MHz after curing of the composition
  • B is the gel fraction after curing of the composition (%)
  • C is the shrinkage after curing of the composition (%)
  • D is the storage modulus after curing of the composition (Pa).
  • the dielectric constant (A) is, for example, using a cured product of the composition, after preparing a standard specimen of a copper plate / hard body / copper plate laminated structure having a size of 2 cm x 2 cm (width x length)
  • the dielectric constant can be calculated using the Agilent 4294A Precision Impedance Analyzer device, and by measuring the value for the dielectric constant of the specimen under vacuum.
  • the gel fraction (B) is, for example, cut the cured body of the composition to a size of 2.5 mm in diameter and 1 mm in thickness to prepare a circular sample, which is then immersed in an excess of ethyl acetate (Ethyl acetate) After standing for 24 hours, the uncured portion was melted and filtered using a strainer, and the separated insoluble fraction was dried in an oven at about 150 ° C. for about 30 minutes to 1 hour, and then measured based on the measured mass change before and after drying. It can be calculated as
  • the shrinkage ratio (C) is, for example, after cutting the cured product of the composition to a size of 2.5 mm in diameter and 1 mm in thickness to prepare a circular sample, and after measuring the specific gravity before and after curing, It can be calculated from the rate of change of the specific gravity later.
  • the storage modulus (D) is, for example, after cutting the cured body of the composition to a size of 8 mm in diameter and 1 mm in thickness to prepare a circular sample, and then using an Advanced Rheometrics Expansion System (ARES) device Can be measured at 1 Hz frequency in sweep mode.
  • RATS Advanced Rheometrics Expansion System
  • the value calculated by the formula 1 may be 30 or more. More specifically, the value calculated by Equation 1 may be 35 or more, 40 or more, 45 or more, 50 or more, 55, or more 60 or more or 65 or more. Such curable compositions can exhibit good adhesion properties while exhibiting low dielectric constant.
  • the upper limit of the value calculated by Equation 1 is not particularly limited and may be appropriately set according to the intended use. For example, 200 or less, 190 or less, 180 or less, 170 or less, 160 or less, 150 or less, 145 Or less than 140 or 135 or less.
  • Exemplary curable compositions may exhibit low dielectric constant after curing.
  • the dielectric constant at 1 MHz after curing of the curable composition may be 3.5 or less, 3.4 or less, 3.3 or less, 3.2 or less, 3.1 or less, 3.0 or less, 2.9 or less, 2.8 or less, 2.7 or less, 2.6 or less, or 2.5 or less.
  • Such a curable composition may be usefully used for adhesion of an optical member that senses a position by sensing an electrical signal such as, for example, a touch panel.
  • the lower limit of the dielectric constant is not particularly limited and may be appropriately set according to the intended use.
  • the dielectric constant is 2.0 or more, 2.1 or more, 2.2 or more, 2.3 or more, 2.4 or more at 1 MHz after curing of the curable composition. Or 2.5 or more.
  • fills the said range can be obtained by including a rubber component mentioned later in a curable composition suitably, for example.
  • Exemplary curable compositions may exhibit a gel fraction suitable for adhesion to the optical member after curing.
  • the gel fraction after curing of the curable composition may be, for example, at least 30%, at least 30.5%, at least 31%, at least 31.5%, or at least 32.5%.
  • the upper limit of the gel fraction may be, for example, 80% or less, 79.5% or less, 79% or less, 78.5% or less, 78% or less, 77.5% or less, 77% or less, 76.5% or less, or 76% or less. Since such a curable composition can exhibit excellent adhesive properties, it can be usefully used for bonding an optical member such as, for example, a touch panel and a display panel.
  • fills the said range can be obtained by including a rubber component mentioned later in a curable composition suitably, for example.
  • Exemplary curable compositions may also exhibit low shrinkage after curing.
  • the curable composition may have a shrinkage after curing of 3.0% or less, 2.95% or less, 2.90% or less, 2.85% or less, 2.80% or less, 2.75% or less, 2.70% or less, or 2.65% or less.
  • Such a curable composition can prevent dimensional changes, warpage, etc. of the adherend due to stress upon curing shrinkage of the resin composition, and thus can be usefully used for bonding an optical member such as a touch panel and a display panel.
  • the lower limit of the shrinkage rate after curing is not particularly limited and may be appropriately set according to the intended use.
  • fills the said range can be obtained by including a rubber component mentioned later in a curable composition suitably, for example.
  • Exemplary curable compositions may also exhibit a storage modulus suitable for adhesion of the optical member.
  • the storage modulus after curing of the curable composition is 20,000 Pa or less, 19,000 Pa or less, 18,000 Pa, or less, 17,0000 Pa or less, 16,000 Pa or less, 15,000 Pa or less, 14,000 Pa or less, 13,000 Pa or less, 12,000 Pa or less, It may be 11,000 Pa or less, 10,000 Pa or less, 9,500 Pa or less, 9,000 Pa or less, 8,500 Pa or less, 8,000 Pa or less, 7,500 Pa or less, 7,000 Pa or less, 6,500 Pa or less, or 6,000 Pa or less.
  • the lower limit of the storage modulus after curing of the curable composition is not particularly limited and may be appropriately set according to the intended use. For example, 1 Pa or more, 100 Pa or more, 500 Pa or more, 1000 Pa or more, 2,000 Pa or more, 2,100 It may be at least Pa, at least 2,200 Pa, at least 2,300 Pa, at least 2,400 Pa, at least 2,500 Pa, or at least 2,600 Pa.
  • a storage modulus that satisfies this range can be achieved, for example, by lowering the crosslinking density or gel fraction to lower the storage modulus. For this purpose, for example, by adding a rubber component to the curable composition or by applying an appropriate amount of monomer. Can be used to control the reactivity of the oligomer.
  • Exemplary curable compositions may also exhibit good adhesion or adhesion.
  • the curable composition has a peel force of 0.3 N / m or more, 0.34 N / m, 0.36 N / m or more, for example, at a room temperature after curing at a peel angle of 180 ° and a peel rate of 300 mm / min. , 0.38 N / m or more, 0.40 N / m or more, or 0.42 N / m or more.
  • Excellent peeling force after curing of such a curable composition can be achieved by using a curable composition that satisfies the correlation of the formula (1).
  • the upper limit of the peeling force is not particularly limited and may be appropriately set according to the intended use.
  • Exemplary curable compositions can also produce a cured product excellent in light transmittance.
  • the curable composition includes, for example, at least 80%, at least 82%, at least 84%, at least 86%, at least 88%, at least 90%, at least 92%, at least 94%, at least 96% of the visible light region after curing, At least 98% or at least 99%. Since such a curable composition is excellent in light transmittance, it can be usefully used for bonding between optical members of a display device.
  • Exemplary curable compositions can include active energy ray curable oligomers.
  • cure by irradiation of an active energy ray, for example, UV can be selected and used,
  • a (meth) acrylate oligomer can be selected and used.
  • the term (meth) acrylate oligomer may refer to an oligomer having at least one (meth) acryloyl group in a molecule. From the viewpoint of curability, an oligomer having at least two (meth) acryloyl groups in the molecule can be suitably used.
  • an oligomer having 2 to 6, 2 to 4 or 2 (meth) acryloyl groups in the molecule may be used, but is not limited thereto.
  • the main chain skeleton of the oligomers for example, oligomers having a (meth) acryloyl group, is not particularly limited. It may be at least one selected from a polydiene skeleton having no functional group, a hydrogenated product of polydiene, polyester, dibutylene glycol, polycarbonate and polyether.
  • polydiene refers to a polymer prepared by using a monomer having two carbon-carbon double bonds.
  • polyisoprene polybutadiene, styrene-butadiene, a copolymer of ethylene and propylene (EPM ) Or terpolymers (EPDM) of ethylene, propylene and nonconjugated dienes, and the like.
  • EPM ethylene and propylene
  • EPDM terpolymers
  • an active energy ray-curable oligomer having a polybutadiene skeleton having a hydroxyl group may be used, but is not limited thereto .
  • Examples of the (meth) acrylate oligomer include urethane-based (meth) acrylate oligomers, polyester-based (meth) acrylate oligomers, polyether-based (meth) acrylate oligomers, epoxy-based (meth) acrylate oligomers, One or more types selected from the group consisting of diene polymer-based (meth) acrylate oligomers and oligomers having a main chain of hydrogenated products of diene polymer-based (meth) acrylates can be selected and used.
  • the urethane-based (meth) acrylate oligomer may mean, for example, a (meth) acrylate oligomer having a urethane bond in the molecule.
  • the urethane-based (meth) acrylate oligomer can be obtained by, for example, esterifying a polyurethane oligomer obtained by the reaction of polybutadienediol, polyether polyol, polyester polyol, polycarbonate diol and the like with polyisocyanate with (meth) acrylic acid.
  • Polybutadiene-modified urethane type (meth) acrylate obtained by (meth) acryl modification of polybutadiene is also contained in a urethane type (meth) acrylate oligomer.
  • Hydrogenated polybutadiene modified urethane type (meth) acrylate obtained by (meth) acryl modification of the hydrogenated polybutadiene is also contained in a urethane type (meth) acrylate oligomer.
  • urethane type (meth) acrylate oligomer 1,2-polybutadiene modified urethane type (meth) acrylate oligomer, polyester urethane type (meth) acrylate oligomer, dibutylene glycol urethane type (meth) acrylate oligomer, polycarbonate urethane type (meth ) Acrylic oligomer, a polyether urethane type (meth) acrylate oligomer, etc. are mentioned.
  • the polyester-based (meth) acrylate oligomer may be obtained by esterifying hydroxyl groups of a polyester oligomer having hydroxyl groups at both terminals obtained by condensation of polyhydric carboxylic acid with a polyhydric alcohol, or with (meth) acrylic acid.
  • the terminal hydroxyl group of the oligomer obtained by adding an alkylene oxide can be obtained by esterifying with (meth) acrylic acid.
  • a polyether (meth) acrylate oligomer can be obtained by esterifying the hydroxyl group of a polyether polyol, for example with (meth) acrylic acid.
  • An epoxy-type (meth) acrylate oligomer can be obtained by reacting and esterifying (meth) acrylic acid with the oxirane ring of a bisphenol-type epoxy resin or a novolak-type epoxy resin of comparatively low molecular weight, for example.
  • denatured this epoxy type (meth) acrylate oligomer partially by dibasic carboxylic anhydride can also be used.
  • the oligomer which has a skeleton of the hydrogenated substance of diene polymer type (meth) acrylate can be obtained by esterifying the hydroxyl group of hydrogenated polybutadiene or hydrogenated polyisoprene which has hydroxyl groups at both terminals, for example (meth) acrylic acid.
  • the oligomer which has such a (meth) acryloyl group can be used individually by 1 type, or can be used in combination of 2 or more type.
  • a urethane type (meth) acrylate oligomer can be selected and used from a viewpoint of sclerosis
  • a bifunctional urethane type (meth) acrylate oligomer can be selected and used.
  • a bifunctional urethane type (meth) acrylate oligomer can mean that two (meth) acryloyl groups are contained in 1 molecule of a urethane type (meth) acrylate oligomer.
  • a bifunctional urethane type (meth) acrylate oligomer can be obtained by esterifying a polyurethane oligomer with (meth) acrylic acid.
  • Polyurethane oligomer can be obtained by reaction of polyisocyanate with polyether polyol, polyester polyol, polycarbonate diol, etc. which have two hydroxyl groups in a molecule
  • polyether polyol having two hydroxyl groups examples include polyethylene glycol, polypropylene glycol, polytetramethylene glycol (polybutylene glycol), polyhexamethylene glycol, 1,3-butylene glycol, 1,4-butylene glycol Neopentylglycol, cyclohexanedimethanol, 2,2-bis (4-hydroxycyclohexyl) propane, bisphenol A, or the like, or a compound in which ethylene oxide or propylene oxide is added.
  • the polyester polyol which has two hydroxyl groups can be obtained, for example by making an alcohol component and an acid component react.
  • Polyester polyols having two hydroxyl groups are, for example, polyethylene glycol, polypropylene glycol, polytetramethylene glycol (polybutylene glycol), 1,3-butylene glycol, 1,4-butylene glycol, 1,6- ⁇ -caprolactone or a compound in which ethylene oxide or propylene oxide is added to hexanediol, neopentyl glycol, 1,4-cyclohexanedimethanol, 2,2-bis (4-hydroxycyclohexyl) propane, bisphenol A, or the like
  • the added compound may be used as an alcohol component, dibasic acids such as adipic acid, sebacic acid, azelaic acid, and dodecanedicarboxylic acid, and anhydrides thereof as an acid component, and the alcohol component and the acid component may be reacted with each other.
  • the weight average molecular weight or the number average molecular weight of the urethane-based (meth) acrylate oligomer may be, for example, in the range of 500 to 100000 or 1000 to 50000 in view of handling properties. This value is not particularly limited, and may be, for example, 500, 1000, 2000, 3000, 4000, 5000, 7000, 10000, 20000, 30000, 40000, 50000 or 100000.
  • This average molecular weight is the value of standard polystyrene conversion measured by the gel permeation chromatography (GPC) method.
  • the amount of the active energy ray-curable oligomer is, in terms of producing a curable composition that satisfies the relationship of the formula 1, in the curable composition, for example, 10% by weight, 11% by weight, 12% by weight, 13 May be included in an amount of at least 20% by weight, at least 14% by weight, or at least 15% by weight, and at most 20% by weight, 19% by weight, 18% by weight, 17% by weight, 16% by weight or 15% by weight. Can be.
  • the curable composition may further include a photopolymerization initiator.
  • a photoinitiator as long as it can start superposition
  • an ultraviolet-ray polymerization initiator, a visible light polymerization initiator, etc. can be used.
  • the ultraviolet polymerization initiator for example, benzoin, benzophenone, acetophenone and the like can be used.
  • the visible light polymerization initiator for example, acyl phosphine oxide, thioxanthone, metallocene and quinone.
  • ⁇ -aminoalkylphenone series and the like can be used as a photopolymerization initiator.
  • Exemplary curable compositions may further include a rubber component.
  • the rubber component may comprise polydiene.
  • a compound having a polyisoprene skeleton or a polybutadiene skeleton, a styrene-butadiene skeleton, a copolymer of ethylene and propylene (EPM) or a terpolymer of ethylene, propylene, and nonconjugated diene (EPDM) May be used, but is not limited thereto.
  • the rubber component may have a functional group such as a hydroxyl group or a carboxyl group at the terminal.
  • a functional group such as a hydroxyl group or a carboxyl group
  • polydiene having a functional group such as a hydroxyl group or a carboxyl group
  • a polybutadiene rubber having a hydroxyl group may be used, but is not limited thereto.
  • the weight average molecular weight of the rubber component may be appropriately selected within a range that does not impair the purpose of the present application, for example, in the range of about 1,000 to about 10,000, about 1,000 to about 5,000 or about 2,000 to 3,000 May be, but is not limited thereto.
  • the content of the rubber component in the curable composition may be included, for example, at least 50 wt%, at least 52 wt%, at least 54 wt%, at least 56 wt%, at least 58 wt% or at least 60 wt%, and at most 70 wt%. , Up to 68 wt%, up to 66 wt%, up to 64 wt%, up to 62 wt% or up to 60 wt%.
  • the curable composition includes the rubber component in the above ratio, it is advantageous to provide a curable composition that satisfies the condition of Formula 1.
  • Exemplary curable compositions may further comprise monomers in addition to the oligomers for the purpose of regulating and diluting active energy curable oligomers, for example, (meth) acrylate oligomers.
  • the content of such monomers may be included in the curable composition, for example, at least 10 weight percent, at least 12 weight percent, at least 14 weight percent, at least 16 weight percent, at least 18 weight percent, or at least 20 weight percent, and at least 30 weight percent. Or less, 28 wt% or less, 26 wt% or less, 24 wt% or less, 22 wt% or less, or 20 wt% or less.
  • a (meth) acrylate monomer can be used, for example, and polyfunctional (meth), such as monofunctional (meth) acrylate and bifunctional, trifunctional, tetrafunctional, 5-functional, and 6 functional, etc. ) Acrylate, etc. can be used variously, For example, monofunctional (meth) acrylate or bifunctional (meth) acrylate can be selected and used.
  • polyfunctional (meth) such as monofunctional (meth) acrylate and bifunctional, trifunctional, tetrafunctional, 5-functional, and 6 functional, etc.
  • Acrylate, etc. can be used variously,
  • monofunctional (meth) acrylate or bifunctional (meth) acrylate can be selected and used.
  • (meth) acrylate for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, stearyl (meth) acrylate, tetrahydrofurfuryl (meth) Acrylate, caprolactone modified tetrahydrofurfuryl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, phenyl ( Meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxytetraethylene glycol (meth) acrylate, phenoxy polyethylene glycol (meth) acrylate, nonylphenoxyethyl ( Meta) acrylate, nonylphenoxytetraethylene
  • polyfunctional (meth) acrylate di (meth) acrylated isocyanurate, tri (meth) acrylated isocyanurate, 1,3-dibutylene glycol di (meth) acrylate, 1,4-butanedioldi ( Meta) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, EO (ethylene oxide) modified bisphenol A di (meth) acrylate, diethylene glycol di (Meth) acrylate, ECH (epichlorohydrin) modified hexahydrophthalic acid di (meth) acrylate, neopentyl glycol di (meth) acrylate, EO modified neopentyl glycol di (meth) acrylate, caprolactone modified hydroxide Oxypibaric acid ester neopentylglycol di (meth) acrylate, ste
  • the curable composition may further include a known silane coupling agent in order to improve the adhesion to the adherend, for example, the adhesion to glass.
  • curable composition may further contain well-known paraffins in order to accelerate hardening of the part which contact
  • the curable composition may further include a known antioxidant including a polymerization inhibitor for the purpose of maintaining storage stability.
  • the curable compositions may further include known additives such as elastomers, plasticizers, fillers, colorants, or crystals, depending on the intended use.
  • exemplary cured bodies may satisfy the relationship of Equation 1 below.
  • Equation 1 A is the dielectric constant at 1 MHz of the cured product, B is the gel fraction (%) of the cured product, C is the shrinkage percentage (%) of the cured product, and D is the storage modulus (Pa) of the cured product.
  • Exemplary cured bodies may include, for example, the curable composition in a cured state.
  • the "cured state” means that the components contained in the composition undergo a crosslinking reaction, a polymerization reaction, or the like. This may mean a case where the state is converted into a hard state.
  • Specific information on the dielectric constant, gel fraction, shrinkage and storage modulus in Equation 1 of the cured body may be equally applicable to the dielectric constant, gel fraction, shrinkage and storage modulus described in the item of the curable composition.
  • Exemplary cured bodies can be prepared by curing the curable composition.
  • the curing method is not particularly limited, and a method of maintaining the composition at an appropriate temperature or irradiating an appropriate active energy ray such that the polymerization reaction may proceed so that the crosslinking reaction of the active energy ray curable oligomer described in the section of the curable composition may proceed. It can be hardened through the process. If the maintenance at the appropriate temperature and the irradiation of the active energy ray is required at the same time, the process can be carried out sequentially or simultaneously.
  • the irradiation of the active energy ray may be performed using, for example, a high-pressure mercury lamp, an electrodeless lamp, a xenon lamp, or the like, and the conditions such as the wavelength and the amount of light of the active energy ray to be irradiated may be the active energy.
  • the crosslinking or polymerization of the precurable oligomer may be selected within a range that can be appropriately made.
  • This application also relates to the use of the curable composition or cured product. Since the curable composition or the cured product exhibits low dielectric constant and excellent adhesive properties, it may be usefully used for bonding various optical members of the display device.
  • the curable composition or cured body can be used to bond the indicator and the optically functional material.
  • a display body may be, for example, a display element such as an LCD (Liquid Crystal Display), an EL (Electroluminescence) display device, an EL illumination, an electronic paper or a plasma display, to which a polarizing plate for glass is attached.
  • an acrylic plate for example, a hard coating or an antireflective coating may be applied to one or both surfaces
  • a PC for example, to improve visibility or to prevent cracking of a display element from external impact
  • a transparent plastic plate such as a polycarbonate (PET) plate, a polyethylene terephthalate (PET) plate, and a polyethylene naphthalate (PEN) plate, tempered glass (for example, a shatterproof film may be attached), or a touch panel input sensor.
  • PET polycarbonate
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • tempered glass for example, a shatterproof film may be attached
  • a touch panel input sensor for example, a touch panel input sensor.
  • the curable composition or cured product may also be usefully used for bonding a transparent substrate and a transparent plate on which a transparent electrode is formed, for example, in a capacitive touch panel.
  • the material of the transparent substrate may be, for example, PC, polymethyl methacrylate (PMMA), a composite of PC and PMMA, cyclo-olefin copolymer (COC), cyclo-olefin polymer (COP).
  • the material of the transparent plate may be, for example, glass, PC, PMMA, composite COC or COP of PC and PMMA.
  • cured material can also be usefully used for the use for bonding a touch panel and the sheet
  • the sheet may be, for example, an icon sheet, a protective sheet, a makeup sheet, or the like, and the material of the sheet may be, for example, PET, PC, COC, or COP.
  • the plate include a decorative plate or a protective plate, and the material of the plate may be, for example, PET glass, PC, PMMA, a composite of PC and PMMA, COC, or COP.
  • the material of the touch panel bonded to the sheet or plate may be, for example, glass, PET, PC, PMMA, a composite of PC and PMMA, COC, or COP.
  • the curable composition or the cured product may also be usefully used, for example, for direct bonding of a touch panel and a display panel of a display device.
  • FIG. 1 exemplarily illustrates a display device including a display panel 101 and a touch panel 102, and the display panel 101 and the touch panel 102 are bonded by the curable composition or the cured body 103. .
  • the curable composition or the cured product may also be usefully used for filling a space spaced between the optical functional material spaced by a spacer and a display panel, for example, in a display device.
  • 2 exemplarily shows a display device in which the optical functional material is a touch panel.
  • the display device may include a display panel 201, a touch panel 202, and a spacer 203 spaced apart from the display panel. In this case, the display panel and the touch panel may be disposed.
  • This spaced space, a so-called air gap space may have a structure in which the curable composition or the cured body 204 is filled.
  • the curable composition or cured product When the curable composition or cured product is applied to the display device, other components constituting the device or a method of constituting the device are not particularly limited, and any known in the art may be used as long as the curable composition or cured product is used. Both materials and methods may be employed.
  • Exemplary curable compositions of the present application can produce a cured product exhibiting low dielectric constant and excellent adhesive properties, and thus are useful for bonding various optical functional members of a display device, for example, bonding a touch panel and a display panel. Can be used.
  • FIG. 1 and 2 are schematic views of an exemplary display device of the present application.
  • FIG. 3 is a schematic diagram of a display device related to the background art.
  • the cured product prepared in Examples and Comparative Examples was cut to a size of 2.5 mm in diameter and 1 mm in thickness to prepare a circular sample, which was then immersed in an excess of ethyl acetate and left for 24 hours to leave uncured portion. After dissolving and filtering using a strainer, the separated insoluble fraction was dried in an oven at about 150 ° C. for about 30 minutes to 1 hour to calculate a gel fraction based on the measured mass change before and after drying.
  • a standard specimen of a copper / hardened body / copper laminated structure having a size of 2 cm ⁇ 2 cm (width ⁇ length) was fabricated, and then the Agilent 4294A Precision Impedance Analyzer was used. The dielectric constant was measured and the dielectric constant was measured by calculating the value for the dielectric constant of the specimen in vacuum.
  • a polyurethane acrylate comprising a polybutadiene rubber having a hydroxyl group and having a weight average molecular weight of 15,000 (hereinafter oligomer A) 18 g and a polybutadiene rubber having a hydroxyl group and having a weight average molecular weight of 10,000 (
  • 2 g of oligomer B) 60 g of polybutadiene rubber (hereinafter referred to as rubber A) having a hydroxyl group as a rubber component and having a weight average molecular weight of 2,000, 20 parts by weight of isobonyl acrylate as a monomer, and 1 g of Darocur TPO as a photopolymerization initiator Mixing produced a curable composition.
  • the cured body After applying the prepared curable composition to about 0.2 mm on a glass substrate, the cured body having a predetermined size according to the measurement sample by irradiating UV of about 365 nm to 400 nm long wavelength using an LED or a metal-halide lamp Prepared.
  • a cured product was prepared in the same manner as in Example 1, except that the composition of the curable composition in Example 1 was adjusted as shown in Table 1 below.
  • Example Oligomer Rubber Monomer Other A B C A B IBOA S.C Initiator One 18 2 - 60 - 20 - One 2 16 4 - 60 - 20 - One 3 14 6 - 60 - 20 - One 4 18 - 2 60 - 20 - One 5 16 - 4 60 - 20 - One 6 14 - 6 60 - 20 - One 7 20 - - - 60 20 0.5 One 8 20 - - 60 - 20 0.5 One 9 22 - - - 60 18 0.5 One 10 20 - - - 60 20 0.25 One 11 20 - - - 60 20 One One 12 20 - - - 60 20 2 One Content Unit (g)-Oligomer A: Polyurethane acrylate containing polybutadiene rubber having hydroxyl group (weight average molecular weight: 15,000)-Oligomer B: Polyurethane acrylate containing polybutadiene rubber having hydroxyl group (weight average molecular weight : 10,000)-oli
  • a cured product was prepared in the same manner as in Example 1 except that the composition of the curable composition in Example 1 was adjusted as shown in Table 2 below.
  • Examples 1 to 12 having a value of Equation 1 or more exhibited a low dielectric constant, and at the same time, it was confirmed that the peeling force was remarkably superior to Comparative Examples 1 to 3 having a value of Equation 1 less than 30.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition durcissable, un corps durci, et des utilisations de la composition durcissable et du corps durci. Une composition durcissable indicative peut produire un corps durci qui présente une faible constante diélectrique et présente d'excellentes caractéristiques adhésives, et peut donc être favorablement utilisée dans le collage de divers éléments optiques fonctionnels d'un dispositif d'affichage, par exemple, le collage direct d'un panneau tactile et d'un panneau d'affichage.
PCT/KR2015/006699 2014-06-30 2015-06-30 Composition durcissable Ceased WO2016003156A1 (fr)

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US15/106,997 US10221340B2 (en) 2014-06-30 2015-06-30 Curable composition
CN201580005947.4A CN105934450B (zh) 2014-06-30 2015-06-30 可固化组合物

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KR10-2014-0081022 2014-06-30
KR20140081020 2014-06-30
KR20140081022 2014-06-30
KR10-2014-0081020 2014-06-30
KR10-2015-0093073 2015-06-30
KR1020150093073A KR101703431B1 (ko) 2014-06-30 2015-06-30 경화성 조성물

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004125868A (ja) * 2002-09-30 2004-04-22 Hitachi Chem Co Ltd 液晶表示装置用シート及びそれを用いた液晶表示装置の製造方法
JP2011190421A (ja) * 2010-03-17 2011-09-29 Hitachi Kasei Polymer Co Ltd 活性エネルギー線硬化型接着剤組成物
KR20120094869A (ko) * 2011-02-17 2012-08-27 닛토덴코 가부시키가이샤 광학용 감압 점착 시트
KR20130063937A (ko) * 2011-12-07 2013-06-17 제일모직주식회사 광경화형 점착제 조성물 및 이를 포함하는 디스플레이 장치
KR101284998B1 (ko) * 2006-10-31 2013-07-10 히타치가세이가부시끼가이샤 광학용 수지 조성물 및 그것을 이용한 광학용 수지 재료, 화상표시용 장치를 위한 광학 필터, 및 화상표시용 장치

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004125868A (ja) * 2002-09-30 2004-04-22 Hitachi Chem Co Ltd 液晶表示装置用シート及びそれを用いた液晶表示装置の製造方法
KR101284998B1 (ko) * 2006-10-31 2013-07-10 히타치가세이가부시끼가이샤 광학용 수지 조성물 및 그것을 이용한 광학용 수지 재료, 화상표시용 장치를 위한 광학 필터, 및 화상표시용 장치
JP2011190421A (ja) * 2010-03-17 2011-09-29 Hitachi Kasei Polymer Co Ltd 活性エネルギー線硬化型接着剤組成物
KR20120094869A (ko) * 2011-02-17 2012-08-27 닛토덴코 가부시키가이샤 광학용 감압 점착 시트
KR20130063937A (ko) * 2011-12-07 2013-06-17 제일모직주식회사 광경화형 점착제 조성물 및 이를 포함하는 디스플레이 장치

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