WO2022130447A1 - Feuille d'étanchéité - Google Patents

Feuille d'étanchéité Download PDF

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Publication number
WO2022130447A1
WO2022130447A1 PCT/JP2020/046517 JP2020046517W WO2022130447A1 WO 2022130447 A1 WO2022130447 A1 WO 2022130447A1 JP 2020046517 W JP2020046517 W JP 2020046517W WO 2022130447 A1 WO2022130447 A1 WO 2022130447A1
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WO
WIPO (PCT)
Prior art keywords
ether group
cyclic ether
sealing sheet
sealing
layer
Prior art date
Application number
PCT/JP2020/046517
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English (en)
Japanese (ja)
Inventor
健太 西嶋
Original Assignee
リンテック株式会社
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by リンテック株式会社 filed Critical リンテック株式会社
Priority to KR1020237007757A priority Critical patent/KR20230119106A/ko
Priority to PCT/JP2020/046517 priority patent/WO2022130447A1/fr
Priority to CN202080107868.5A priority patent/CN116724680A/zh
Publication of WO2022130447A1 publication Critical patent/WO2022130447A1/fr

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Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/842—Containers
    • H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations

Definitions

  • the present invention relates to a sealing sheet having a curable sealing agent layer.
  • organic EL elements have been attracting attention as light emitting elements capable of high-luminance light emission by low-voltage direct current drive.
  • the organic EL element has a problem that the light emission characteristics such as the light emission brightness, the light emission efficiency, and the light emission uniformity tend to deteriorate with the passage of time. It is considered that oxygen, moisture, etc. infiltrate into the organic EL element and deteriorate the electrode and the organic layer as a cause of the problem of deterioration of the light emitting characteristics. Therefore, the organic EL element is sealed by using a sealing material. However, it has been done to prevent the infiltration of oxygen and water.
  • Patent Document 1 contains a resin component and a curing agent, and the resin component contains a biphenyl skeleton-containing epoxy resin having a weight average molecular weight within a specific range and an alicyclic skeleton having a weight average molecular weight within a specific range.
  • Described is an image display device encapsulant characterized by containing an epoxy resin and a styrene-based oligomer having a weight average molecular weight within a specific range.
  • the image display device encapsulant has a relatively low dielectric constant because it contains a biphenyl skeleton-containing resin and a styrene-based oligomer, and the image display device encapsulant is used as an encapsulant in a touch panel. It is also described that the touch panel is less likely to malfunction due to the sealing material.
  • the curable sheet-shaped adhesive has been suitably used as a material for forming a sealing material (hereinafter, "sheet-shaped adhesive for forming a sealing material” is referred to as “sealing”. Sometimes referred to as “stopping agent layer”).
  • sheet-shaped adhesive for forming a sealing material is referred to as "sealing”.
  • stopping agent layer Sometimes referred to as "stopping agent layer”.
  • a sealing agent layer that gives a cured product having low dielectric properties is useful as a material for forming a sealing material used for a touch panel or the like.
  • the present invention has a sealing sheet (that is, a sealing sheet having a sealing agent layer which is a cured product having low dielectric properties and excellent transparency), which is more suitable as a material for forming a sealing material used for a touch panel or the like. ) Is intended to be provided.
  • the present inventors have diligently studied a curable encapsulant layer in order to solve the above problems.
  • the cured product of the adhesive layer containing the phenoxy resin having a glass transition temperature (Tg) of 90 ° C. or higher and the compound having an alicyclic skeleton and a cyclic ether group has low dielectric properties and is transparent. We have found that it is excellent in properties and have completed the present invention.
  • sealing sheets [1] to [7] are provided.
  • a sealing sheet having a curable sealing agent layer which satisfies the following requirements (I), (II), and (III).
  • a sealing sheet having a sealing agent layer which has low dielectric properties and becomes a cured product having excellent transparency.
  • the sealing sheet of the present invention is a sealing sheet having a curable sealing agent layer, and is characterized by satisfying the following requirements (I), (II), and (III). be.
  • the "sealing agent layer” means "sheet-like adhesive for forming a sealing material".
  • the cured product of the encapsulant layer is used as an encapsulant.
  • the encapsulant layer is a layer that exhibits non-fluidity at room temperature.
  • the encapsulant layer may be strip-shaped or elongated (strip-shaped).
  • the encapsulant layer contains a phenoxy resin having a glass transition temperature (Tg) of 90 ° C. or higher (hereinafter, may be referred to as “phenoxy resin (A)”).
  • the phenoxy resin is a polymer whose main chain is a double addition structure of an aromatic diol and an aromatic diglycidyl ether.
  • the phenoxy resin generally corresponds to a high molecular weight epoxy resin and has a degree of polymerization of about 100 or more.
  • the phenoxy resin (A) is important in that it fully exhibits the characteristics of a compound having an alicyclic skeleton and a cyclic ether group (hereinafter, may be referred to as "cyclic ether group-containing compound (B)").
  • cyclic ether group-containing compound (B) is a encapsulant. It is preferable that it is contained in a large amount in the layer. However, the encapsulant layer containing a large amount of the cyclic ether group-containing compound (B) may have a reduced shape retention before curing.
  • the sealing agent layer of the sealing sheet of the present invention contains the phenoxy resin (A), even if it contains a large amount of the cyclic ether group-containing compound (B), it is not cured yet.
  • the shape can be kept constant for a long period of time.
  • the glass transition temperature (Tg) of the phenoxy resin (A) is 90 ° C. or higher, preferably 95 to 150 ° C., and more preferably 100 to 150 ° C.
  • the glass transition temperature (Tg) of the phenoxy resin (A) can be measured using a differential scanning calorimeter.
  • the weight average molecular weight (Mw) of the phenoxy resin (A) is usually 10,000 to 200,000, preferably 20,000 to 100,000, and more preferably 30,000 to 80,000. If the weight average molecular weight (Mw) of the phenoxy resin (A) is too small, it tends to be difficult for the encapsulant layer to maintain a constant shape. If the weight average molecular weight (Mw) of the phenoxy resin (A) is too large, the encapsulant layer tends to be inferior in handleability.
  • the weight average molecular weight (Mw) of the phenoxy resin (A) can be determined as a standard polystyrene-equivalent value by performing gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.
  • the epoxy equivalent of the phenoxy resin (A) is preferably 5,000 g / eq or more, more preferably 6,500 g / eq or more.
  • the epoxy equivalent can be measured according to JIS K7236.
  • phenoxy resin (A) examples include bisphenol A type phenoxy resin, bisphenol F type phenoxy resin, bisphenol S type phenoxy resin, bisphenol A type and bisphenol F type copolymer type phenoxy resin, bisphenol E type phenoxy resin, and naphthalene type phenoxy resin. , Novolak type phenoxy resin, biphenyl type phenoxy resin, cyclopentadiene type phenoxy resin and the like.
  • the phenoxy resin (A) can be used alone or in combination of two or more.
  • the phenoxy resin (A) can be obtained by a method of reacting a bifunctional phenol with epihalohydrin up to a high molecular weight, or a method of subjecting a bifunctional epoxy resin and a bifunctional phenol to a double addition reaction.
  • a bifunctional epoxy resin and a bifunctional phenol can be obtained by reacting bifunctional phenols and epihalohydrin in the presence of an alkali metal hydroxide in an inert solvent at a temperature of 40 to 120 ° C.
  • the bifunctional epoxy resin and the bifunctional phenols are mixed with an amide solvent or an ether solvent having a boiling point of 120 ° C. or higher in the presence of a catalyst such as an alkali metal compound, an organic phosphorus compound or a cyclic amine compound.
  • It can also be obtained by performing a double addition reaction by heating to 50 to 200 ° C. in an organic solvent such as a ketone solvent, a lactone solvent, or an alcohol solvent with a reaction solid content concentration
  • the bifunctional phenols are not particularly limited as long as they are compounds having two phenolic hydroxyl groups.
  • monocyclic bifunctional phenols such as hydroquinone, 2-bromohydroquinone, resorcinol, catechol; bisphenols such as bisphenol A, bisphenol F, bisphenol AD, bisphenol S; dihydroxybiphenyls such as 4,4'-dihydroxybiphenyl; Dihydroxyphenyl ethers such as bis (4-hydroxyphenyl) ethers; and the aromatic rings of these phenolic skeletons include linear alkyl groups, branched alkyl groups, aryl groups, methylol groups, allyl groups, cyclic aliphatic groups, halogens.
  • epihalohydrin examples include epichlorohydrin, epibromhydrin, epiiodohydrin and the like.
  • a commercially available product can also be used as the phenoxy resin (A).
  • Commercially available products include YX7200 (glass transition temperature: 150 ° C.), YX6954 (bisphenol acetophenone skeleton-containing phenoxy resin, glass transition temperature: 130 ° C.), jER1256 (glass transition temperature: 98 ° C.) (all manufactured by Mitsubishi Chemical Corporation); And so on.
  • the content of the phenoxy resin (A) is preferably 30 to 55% by mass, more preferably 35 to 50% by mass, based on the entire encapsulant layer.
  • the content of the phenoxy resin (A) is within the above range, the shape retention of the sealant layer is improved, and the sealant has low dielectric properties and is a cured product having excellent transparency. It becomes easier to obtain a layer.
  • "having a low dielectric property” means satisfying the requirement (III).
  • the encapsulant layer contains one or more compounds having an alicyclic skeleton and a cyclic ether group [cyclic ether group-containing compound (B)].
  • the alicyclic skeleton and the compound having a cyclic ether group refer to a compound having an alicyclic skeleton in the molecule and further having at least one, preferably two or more cyclic ether groups in the molecule.
  • the phenoxy resin (A) is not included in the alicyclic skeleton and the compound having a cyclic ether group.
  • the molecular weight of the cyclic ether group-containing compound (B) is usually 100 to 5,000, preferably 200 to 3,000.
  • the cyclic ether equivalent of the cyclic ether group-containing compound (B) is preferably 50 g / eq or more and 1000 g / eq or less, and more preferably 100 g / eq or more and 800 g / eq or less.
  • the cyclic ether group examples include an oxylan group (epoxy group), an oxetane group (oxetanyl group), a tetrahydrofuryl group, a tetrahydropyranyl group and the like.
  • the oxylan group is preferable as the cyclic ether group.
  • the oxylan group includes a group having an oxylan structure such as a glycidyl group, a glycidyl ether group, and an epoxycyclohexyl group.
  • the cyclic ether group-containing compound (B) can be obtained by epoxidizing a polyglycidyl etherified product of a polyhydric alcohol having at least one alicyclic structure, or a cyclohexene or cyclopentene ring-containing compound with an oxidizing agent.
  • Cycloalkene oxide compounds such as cyclohexene oxide and cyclopentene oxide-containing compounds can be mentioned.
  • Typical compounds of the cyclic ether group-containing compound (B) include hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, and 3,4-epoxy-1-methyl.
  • Cyclohexyl-3,4-epoxy-1-methylhexanecarboxylate 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexyl Methyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, bis (3,4-epoxycyclohexylmethyl) Adipate, 3,4-epoxy-6-methylcyclohexanecarboxylate, methylenebis (3,4-epoxycyclohexane), propane-2,2-diyl-bis (3,4-epoxycyclohexane), 2,2-bis (3) , 4-Epoxycyclohexyl) Propane, Dicyclopentadienediepoxyside, E
  • a commercially available product can also be used as the cyclic ether group-containing compound (B).
  • Commercially available products include seroxide 2021P, seroxide 2081, seroxide 2000, seroxide 3000 (above, manufactured by Daicel); Epolite 4000 (manufactured by Kyoeisha Kagaku); YX8000, YX8034 (above, manufactured by Mitsubishi Chemical); ADEKA REGIN EP-4088S, ADEKA REGIN EP-4088L, ADEKA REGIN EP-4080E (all manufactured by ADEKA); and the like.
  • the cyclic ether group-containing compound (B) can be used alone or in combination of two or more.
  • the content of the cyclic ether group-containing compound (B) is preferably 45% by mass or more, more preferably 55 to 70% by mass, based on the entire encapsulant layer.
  • the content of the cyclic ether group-containing compound (B) is 50% by mass or more with respect to the entire encapsulant layer, a cured product of the encapsulant layer having a lower dielectric constant and more excellent transparency can be obtained. It will be easier to obtain.
  • At least one of the cyclic ether group-containing compound (B) is preferably a compound that is liquid at 25 ° C.
  • "Liquid at 25 ° C” means having fluidity at 25 ° C.
  • the cyclic ether group-containing compound (B) preferably has a viscosity measured at 25 ° C. and 1.0 rpm using an E-type viscometer at 2 to 10000 mPa ⁇ s.
  • the content thereof is preferably 55% by mass or more, more preferably 55% by mass or more, based on the entire encapsulant layer. , 55-70% by mass.
  • At least one of the cyclic ether group-containing compound (B) is preferably a compound having a glycidyl ether group as the cyclic ether group. Since the glycidyl ether group is not so reactive as the epoxycyclohexyl group or the like, it is easy to obtain a sealing sheet having better storage stability by using the cyclic ether group-containing compound (B) having a glycidyl ether group. Become.
  • the content thereof is preferably 55% by mass or more, more preferably 55% by mass or more, based on the entire encapsulant layer. , 55-70% by mass.
  • the relative permittivity of the cured product of the sealant layer at 23 ° C. and a frequency of 100 kHz (hereinafter, this relative permittivity may be referred to as “relative permittivity ( ⁇ )”) is 3.5 or less.
  • a cured product having a relative permittivity ( ⁇ ) of 3.5 or less as a sealing material in an electronic device equipped with a touch sensor such as a touch panel, malfunction of the electronic device caused by the sealing material can be suppressed. Can be done.
  • the relative permittivity ( ⁇ ) is preferably 3.48 or less, more preferably 3.47 or less. There is no particular lower limit for the relative permittivity ( ⁇ ), but it is usually 2.00 or more.
  • the sample for measuring the relative permittivity ( ⁇ ) is not particularly limited as long as the sealant layer is sufficiently cured.
  • a cured product obtained under curing conditions of 110 ° C. for 1 hour can be used as a measurement sample for the relative permittivity ( ⁇ ).
  • the relative permittivity ( ⁇ ) can be measured according to the method described in Examples.
  • the cured product of the sealant layer containing a large amount of the cyclic ether group-containing compound (B) tends to have a small relative permittivity ( ⁇ ). Therefore, the encapsulant layer satisfying the requirement (III) can be efficiently formed by adjusting the content of the cyclic ether group-containing compound (B).
  • the encapsulant layer may contain a curing agent.
  • a curing agent By using a curing agent, it is possible to obtain a sealing agent layer in which the curing reaction proceeds more efficiently.
  • the curing agent is not particularly limited as long as it initiates the curing reaction of at least the cyclic ether group-containing compound (B). Since the curing reaction can be completed in a relatively short time, a curing agent that starts the curing reaction by heating is preferably used. Examples of the curing agent that initiates the curing reaction by heating include a thermal cationic polymerization initiator and other thermally reactive curing agents.
  • the thermal cationic polymerization initiator is a compound capable of generating a cationic species that initiates polymerization by heating.
  • Examples of the thermal cationic polymerization initiator include sulnifoum salt, quaternary ammonium salt, phosphonium salt, diazonium salt, iodonium salt and the like.
  • sulfonium salt examples include triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluoroalcinate, tris (4-methoxyphenyl) sulfonium hexafluoroalcinate, and diphenyl (4-phenylthiophenyl) sulfonium. Hexafluoroalcinate and the like can be mentioned.
  • a commercially available product can also be used as the sulfonium salt.
  • Commercially available products include Adeca Opton SP-150, Adeka Opton SP-170, Adeka Opton CP-66, Adeka Opton CP-77 (above, manufactured by Asahi Denka Co., Ltd.), Sun Aid SI-60L, Sun Aid SI-80L, Sun Aid SI-100L, Sun Aid SI.
  • Examples of the quaternary ammonium salt include tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium hydrogen sulfate, tetraethylammonium tetrafluoroborate, tetraethylammonium p-toluenesulfonate, N, N-dimethyl-N-.
  • Benzylanilinium hexafluoroantimonate N, N-dimethyl-N-benzylanilinium tetrafluoroborate, N, N-dimethyl-N-benzylpyridinium hexafluoroantimonate, N, N-diethyl-N-benzyltrifluoromethanesulfonate , N, N-dimethyl-N- (4-methoxybenzyl) pyridinium hexafluoroantimonate, N, N-diethyl-N- (4-methoxybenzyl) toluidinium hexafluoroantimonate and the like.
  • Examples of the phosphonium salt include ethyltriphenylphosphonium hexafluoroantimonate and tetrabutylphosphonium hexafluoroantimonate.
  • diazonium salt examples include AMERICURE (manufactured by American Can) and ULTRASET (manufactured by Asahi Denka Co., Ltd.).
  • iodonium salt examples include diphenyliodonium hexafluoroalcinate, bis (4-chlorophenyl) iodonium hexafluoroalcinate, bis (4-bromophenyl) iodonium hexafluoroalcinate, and phenyl (4-methoxyphenyl) iodonium hexafluoroalcinate. Can be mentioned.
  • UV-9310C manufactured by Toshiba Silicone
  • Photoinitiator 2074 manufactured by Rhone-Poulenc
  • UVE series products manufactured by General Electric
  • FC series products Mine Sota Mining and Manufacturing
  • heat-reactive curing agent other than the thermal cationic polymerization initiator examples include amine compounds such as benzylmethylamine and 2,4,6-trisdimethylaminomethylphenol; 2-methylimidazole, 3-ethyl-4-methylimidazole, 2 -Idazole compounds such as heptadecylimidazole; Lewis acids such as boron trifluoride / monoethylamine complex, boron trifluoride / piperazine complex; and the like.
  • the curing agent may be used alone or in combination of two or more.
  • the content of the curing agent is not particularly limited, but is preferably 0.1 to 15 parts by mass, more preferably 1 to 10 parts by mass, and further preferably 1 with respect to 100 parts by mass of the cyclic ether group-containing compound (B). ⁇ 5 parts by mass.
  • the encapsulant layer may contain a silane coupling agent.
  • a silane coupling agent By using a silane coupling agent, it becomes easy to obtain a sealing agent layer having better moist heat durability.
  • silane coupling agent a known silane coupling agent can be used. Of these, an organosilicon compound having at least one alkoxysilyl group in the molecule is preferable.
  • the silane coupling agent include 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltri.
  • the content of the silane coupling agent is preferably 0.01 to 5% by mass, more preferably 0.05 to 1% by mass in the entire encapsulant layer. Is.
  • the encapsulant layer may contain other components as long as it does not interfere with the effects of the present invention.
  • other components include additives such as ultraviolet absorbers, antistatic agents, light stabilizers, antioxidants, resin stabilizers, fillers, pigments, bulking agents, and softeners. These can be used alone or in combination of two or more. When the encapsulant layer contains these additives, the content thereof can be appropriately determined according to the purpose.
  • the thickness of the encapsulant layer is usually 1 to 50 ⁇ m, preferably 1 to 25 ⁇ m, and more preferably 5 to 25 ⁇ m.
  • the encapsulant layer having a thickness within the above range is suitably used as a material for forming the encapsulant.
  • the thickness of the encapsulant layer can be measured according to JIS K 7130 (1999) using a known thickness gauge.
  • the method for forming the encapsulant layer is not particularly limited.
  • the cast method can be used to form the encapsulant layer.
  • a sealant composition containing the components constituting the sealant layer is prepared, and the obtained sealant composition is used as a base by a known method.
  • a sealant layer can be formed by applying a coating to the peeled layer surface of the material or the peeling film and drying the obtained coating film.
  • the encapsulant composition may contain a solvent.
  • a solvent aromatic hydrocarbon solvents such as benzene and toluene; ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone; n-pentane, n-hexane and n- An aliphatic hydrocarbon solvent such as heptane; an alicyclic hydrocarbon solvent such as cyclopentane, cyclohexane, and methylcyclohexane; and the like can be mentioned. These solvents may be used alone or in combination of two or more. The content of the solvent can be appropriately determined in consideration of coatability and the like.
  • Examples of the method for applying the encapsulant composition include a spin coating method, a spray coating method, a bar coating method, a knife coating method, a roll coating method, a blade coating method, a die coating method, and a gravure coating method.
  • Examples of the method for drying the coating film include conventionally known drying methods such as hot air drying, hot roll drying, and infrared irradiation.
  • the conditions for drying the coating film are, for example, 80 to 150 ° C. for 30 seconds to 5 minutes.
  • the encapsulant layer has thermosetting property
  • by heating the encapsulant layer at least the cyclic ether group of the cyclic ether group-containing compound (B) reacts, and the encapsulant layer is cured.
  • the conditions for thermosetting the sealant layer are not particularly limited.
  • the heating temperature is usually 80 to 200 ° C, preferably 90 to 150 ° C.
  • the heating time is usually 30 minutes to 12 hours, preferably 1 to 6 hours.
  • the dielectric loss tangent of the cured product of the sealant layer at 23 ° C. and a frequency of 100 kHz (hereinafter, this dielectric loss tangent may be referred to as “dielectric loss tangent ( ⁇ )”) is preferably 0.05 or less. It is more preferably 0.045 or less, still more preferably 0.040 or less. There is no particular lower limit for the dielectric loss tangent ( ⁇ ), but it is usually 0.0001 or more. When the dielectric loss tangent ( ⁇ ) is 0.05 or less, it is possible to suppress heat generation and signal attenuation. The dielectric loss tangent ( ⁇ ) can be measured according to the method described in the examples. Since the sealing agent layer of the sealing sheet of the present invention contains the cyclic ether group-containing compound (B), the cured product tends to have a low dielectric loss tangent.
  • the total light transmittance of the cured product of the sealant layer is preferably 90% or more, more preferably 91% or more. There is no particular upper limit to the total light transmittance, but it is usually 100% or less.
  • a cured product having a total light transmittance of 90% or more as a sealing material in a display device such as a touch panel, an electronic device having better visibility can be obtained.
  • Total light transmittance can be measured according to the method described in Examples. Since the sealing agent layer of the sealing sheet of the present invention contains the cyclic ether group-containing compound (B), the cured product tends to have a high total light transmittance.
  • the haze value of the cured product of the sealant layer is preferably 1% or less, more preferably 0.9% or less, and particularly preferably 0.4% or less. There is no particular lower limit for the haze value, but it is usually 0% or more.
  • a cured product having a haze value of 1% or less as a sealing material in a display device such as a touch panel, an electronic device having better visibility can be obtained.
  • the haze value can be measured according to the method described in the examples. Since the sealing agent layer of the sealing sheet of the present invention contains the cyclic ether group-containing compound (B), the cured product tends to have a low haze value.
  • the CIE 1976 L * a * b * b * value in the color space of the cured product of the encapsulant layer is preferably -1 or more and +1 or less.
  • a cured product having a b * value within the above range as a sealing material in a display device such as a touch panel, an electronic device having better visibility can be obtained.
  • the b * value can be measured according to the method described in the examples. Since the sealing agent layer of the sealing sheet of the present invention contains the cyclic ether group-containing compound (B), the b * value tends to be close to 0.
  • the sealing sheet of the present invention has the above-mentioned sealing agent layer.
  • the sealing sheet of the present invention may have a base material, a release film, a functional film and the like in addition to the sealing agent layer.
  • a resin film can usually be used as the base material.
  • the resin components of the resin film include polyimide, polyamide, polyamideimide, polyphenylene ether, polyether ketone, polyether ether ketone, polyolefin, polyester, polycarbonate, polysulfone, polyether sulfone, polyphenylene sulfide, polyarylate, acrylic resin, and cyclo. Examples thereof include olefin polymers, aromatic polymers, polyurethane polymers, liquid crystal polymer films and the like.
  • the thickness of the base material is not particularly limited, but is preferably 10 to 500 ⁇ m, more preferably 10 to 300 ⁇ m, and even more preferably 15 to 200 ⁇ m.
  • the release film functions as a support in the manufacturing process of the sealing sheet and also functions as a protective sheet for the sealing agent layer until the sealing sheet is used.
  • the release film is usually peeled off.
  • a conventionally known one can be used.
  • a base material for a release film having a release layer that has been peeled with a release agent can be mentioned.
  • the base material for the release film paper base materials such as glassin paper, coated paper, and high-quality paper; laminated paper obtained by laminating a thermoplastic resin such as polyethylene on these paper base materials; polyethylene terephthalate resin, polybutylene terephthalate resin, etc.
  • Plastic films such as polyethylene naphthalate resin, polypropylene resin, and polyethylene resin; and the like.
  • the release agent examples include rubber-based elastomers such as silicone-based resins, olefin-based resins, isoprene-based resins, and butadiene-based resins, long-chain alkyl-based resins, alkyd-based resins, and fluorine-based resins.
  • the thickness of the release film is not particularly limited, but is usually about 20 to 250 ⁇ m.
  • the sealing sheet of the present invention may have two release films, one on each side of the sealant layer, or only on one side of the sealant layer. It may have a release film.
  • the functional film examples include a conductive film, a gas barrier film, an antireflection film, a retardation film, a viewing angle improving film, a brightness improving film and the like.
  • examples of the gas barrier film include a film having a film of a metal or an inorganic compound.
  • the thickness of the functional film is not particularly limited, but is usually 5 to 200 ⁇ m, preferably 10 to 100 ⁇ m.
  • the sealing agent layer of the sealing sheet of the present invention is suitably used as a material for forming a sealing material for an electronic device.
  • the sealant layer of the sealing sheet of the present invention gives a cured product having low dielectric properties. Since this characteristic is utilized, the electronic device preferably provided with a touch sensor such as a touch panel. Further, the sealing agent layer of the sealing sheet of the present invention gives a cured product having excellent transparency. Since this characteristic is utilized, an electronic device that is required to have light transmission is preferable as the electronic device.
  • Examples of the electronic device required to have light transmission include an organic EL display, an organic EL element such as an organic EL lighting; a liquid crystal element such as a liquid crystal display; an electronic paper element; a solar cell element; a light emitting diode; and the like.
  • the method of sealing the electronic device using the sealing sheet of the present invention is not particularly limited.
  • the electronic device can be sealed by attaching the sealant layer of the sealing sheet of the present invention to the target electronic device and then curing the sealant layer by the above method.
  • Phenoxy resin (A1) (manufactured by Mitsubishi Chemical Corporation, trade name: YX6954BH30, glass transition temperature (Tg): 130 ° C., epoxy equivalent: 10,000 to 16,000 g / eq)
  • Phenoxy resin (A2) (manufactured by Mitsubishi Chemical Corporation, trade name: 1256B40, glass transition temperature (Tg): 98 ° C., epoxy equivalent: 6,700 to 8,000 g / eq)
  • Phenoxy resin (A3) (manufactured by Mitsubishi Chemical Corporation, trade name: YX8100BH30, glass transition temperature (Tg): 150 ° C.)
  • Methyl ethyl ketone contains 100 parts by mass of phenoxy resin (A1), 150 parts by mass of compound (B1) having a cyclic ether group, 3.3 parts by mass of thermal cationic polymerization initiator (C1), and 0.2 parts by mass of silane coupling agent (D1).
  • A1 phenoxy resin
  • B1 compound having a cyclic ether group
  • C1 thermal cationic polymerization initiator
  • D1 silane coupling agent
  • Examples 2 to 3 Comparative Examples 1 and 2
  • a sealing sheet was obtained in the same manner as in Example 1 except that the type and amount of each component constituting the sealing agent layer were changed to those shown in Table 1.
  • Total light transmittance One release film of the sealing sheet obtained in Examples or Comparative Examples was peeled off and removed to expose the sealing agent layer.
  • the exposed sealant layer was bonded to non-alkali glass at 23 ° C. using a laminator to obtain a laminated body.
  • the obtained laminate was heated at 110 ° C. for 1 hour to cure the encapsulant layer, and then another release film was peeled off to obtain a measurement sample.
  • the total light transmittance (%) of the obtained measurement sample was measured using a haze meter (NDH-2000, manufactured by Nippon Denshoku Kogyo Co., Ltd.) in accordance with JIS K7361: 1997.
  • the sealing agent layer of the sealing sheet obtained in Examples 1 to 3 contains a large amount of a compound having an alicyclic skeleton and a cyclic ether group [cyclic ether group-containing compound (B)], the cured product thereof is , Has low dielectric properties and is excellent in transparency.
  • the cured product of the sealing agent layer of the sealing sheet obtained in Comparative Examples 1 and 2 using the compound having an aromatic skeleton and the cyclic ether group instead of the cyclic ether group-containing compound (B) is dielectric. The rate is high.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Epoxy Resins (AREA)
  • Laminated Bodies (AREA)

Abstract

La présente invention concerne une feuille d'étanchéité qui a une couche d'étanchéité durcissable. La feuille d'étanchéité est caractérisée en ce qu'elle satisfait les conditions (I), (II) et (III). Condition (I) : La couche d'agent d'étanchéité contient une résine phénoxy qui a une température de transition vitreuse (Tg) d'au moins 90 °C. Condition (II) : La couche d'agent d'étanchéité contient un ou plusieurs types de composé qui a un squelette alicyclique et un groupe éther cyclique. Condition (III) : Le produit de durcissement de la couche d'agent d'étanchéité a une constante diélectrique inférieure ou égale à 3,5 à 23 °C et une fréquence de 100 kHz. La présente invention concerne ainsi une feuille d'étanchéité qui a une couche d'agent d'étanchéité qui forme un produit durci qui a de faibles caractéristiques diélectriques et une excellente transparence.
PCT/JP2020/046517 2020-12-14 2020-12-14 Feuille d'étanchéité WO2022130447A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018235824A1 (fr) * 2017-06-23 2018-12-27 三井化学株式会社 Matériau d'étanchéité pour dispositif d'affichage d'image et feuille d'étanchéité pour dispositif d'affichage d'image
WO2019065455A1 (fr) * 2017-09-29 2019-04-04 三井化学株式会社 Matériau d'étanchéité pour dispositif d'affichage d'images et feuille d'étanchéité pour dispositif d'affichage d'images

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018235824A1 (fr) * 2017-06-23 2018-12-27 三井化学株式会社 Matériau d'étanchéité pour dispositif d'affichage d'image et feuille d'étanchéité pour dispositif d'affichage d'image
WO2019065455A1 (fr) * 2017-09-29 2019-04-04 三井化学株式会社 Matériau d'étanchéité pour dispositif d'affichage d'images et feuille d'étanchéité pour dispositif d'affichage d'images

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