WO2017099055A1 - 封止用組成物 - Google Patents
封止用組成物 Download PDFInfo
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- WO2017099055A1 WO2017099055A1 PCT/JP2016/086168 JP2016086168W WO2017099055A1 WO 2017099055 A1 WO2017099055 A1 WO 2017099055A1 JP 2016086168 W JP2016086168 W JP 2016086168W WO 2017099055 A1 WO2017099055 A1 WO 2017099055A1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- 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
Definitions
- This invention relates to the composition for sealing which can seal without damaging an organic EL element and can prevent deterioration by a water
- An organic electroluminescence (sometimes referred to as “organic EL” in this specification) element has a structure in which a light-emitting layer is sandwiched between a pair of counter electrodes. Electrons are injected from one electrode and the other Holes are injected from the electrode. Light emission occurs when the injected electrons and holes recombine in the light emitting layer.
- organic EL elements There are two types of light extraction methods for organic EL elements, a top emission type and a bottom emission type, and the top emission type is preferable because it has a high aperture ratio and is excellent in light extraction efficiency.
- An organic EL device including an organic EL element is expected as a full-color flat panel display or as an alternative to an LED due to high impact resistance and high visibility and a variety of emission colors.
- organic EL elements are more susceptible to moisture than other electronic components, and moisture that penetrates into the organic EL elements can cause electrode oxidation or organic modification, resulting in a significant decrease in light emission characteristics.
- Met As a method for solving this problem, a method of sealing (or covering) the periphery of the organic EL element with a resin having excellent moisture resistance is known.
- the organic EL element formed on the substrate is filled with a sealing composition having a property of being cured by UV irradiation, and then sealed by curing the sealing composition.
- the above method (1) has a problem that the light emission characteristics are deteriorated by directly exposing the organic EL element to UV.
- a color filter is disposed on top of the organic EL element in order to form an organic EL device having high contrast, since the UV is blocked by the color filter, the sealing composition may be insufficiently cured. Was a problem.
- the organic EL device can be prevented from being deteriorated in light emission characteristics by being directly exposed to UV, but since the curing of the sealing composition proceeds rapidly by UV irradiation, When the laminating operation is delayed, it becomes difficult to perform the laminating operation, and the yield decreases.
- Patent Document 1 discloses that a sealing composition containing an epoxy compound, a polymerization initiator, and a crown ether or a polyether as a curing retarder proceeds after UV irradiation even if UV is blocked. Therefore, it is described that when the composition is used in the above method (2), it can be sealed while suppressing deterioration of the organic EL element due to UV.
- crown ethers and polyethers are decomposed by cations to generate outgas, and the organic EL element deteriorates due to the outgas.
- an object of the present invention is a composition used as a dam material when sealing an organic EL element by a dam and fill method, and the organic EL element is efficiently and low-exposed without directly exposing the organic EL element to UV.
- An object of the present invention is to provide an organic EL device sealing composition capable of protecting an organic EL device by forming a dam having an outgassing property and a moisture proof property.
- the present inventor is selected from N-glycidyl compounds, N-vinyl compounds, and N-allyl compounds that are weakly basic to cations generated from the photocationic polymerization initiator.
- At least one compound traps cations generated from the photocationic polymerization initiator by UV irradiation, suppresses the progress of cationic polymerization, and heats It has a function of releasing a cation upon treatment to promote cationic polymerization, the N-glycidyl compound or the like does not cause outgassing, and a sealing composition containing the N-glycidyl compound or the like By adjusting the timing of UV irradiation and heat treatment, the pot life can be controlled freely.
- the composition is irradiated with UV, and then bonded to the organic EL element, followed by heat treatment, so that the organic EL element is not directly exposed to UV and is sealed without difficulty in bonding. It was found that the organic EL element can be sealed with a cured product having low outgassing and moisture resistance.
- the present invention has been completed based on these findings.
- this invention is a composition used as a dam material when sealing an organic electroluminescent element by the dam and fill method, Comprising: The following component (A), component (B), component (C), component The composition for organic electroluminescent element sealing containing (D) is provided.
- the component (C) is represented by the following formula (c-1):
- R a is a group obtained by removing t hydrogen atoms from a structural formula of a hydrocarbon, a structural formula of a heterocyclic ring, or a structural formula in which a hydrocarbon and a heterocyclic ring are bonded via a single bond.
- R b represents a hydrogen atom, or a group selected from a hydrocarbon group, a heterocyclic group, and a group in which these are bonded via a single bond
- R c represents a glycidyl group, a vinyl group, and an allyl group.
- At least one group selected from: s represents 1 or 2, t represents an integer of 1 or more, and when t is 2 or more, the groups in two or more square brackets are the same. Or may be different) And / or the following formula (c-2) (In formula (c-2), ring Z represents a heterocyclic ring containing a nitrogen atom, R c represents at least one group selected from a glycidyl group, a vinyl group, and an allyl group. U represents one or more. Represents an integer. When u is 2 or more, two or more nitrogen atoms contained in ring Z may be directly bonded or may be bonded via other atoms)
- the said composition for organic electroluminescent element sealing which is a compound represented by these is provided.
- the present invention also provides the above-mentioned composition for sealing an organic electroluminescent element, containing 0.05 to 3 parts by weight of the component (C) with respect to 1 part by weight of the component (B).
- the present invention further provides the above-mentioned composition for sealing an organic electroluminescent device, further comprising the following component (E).
- component (E) Compound having one or more glycidyl ether groups in one molecule (excluding compounds corresponding to component (A) and component (C))
- the present invention also provides the composition for sealing an organic electroluminescent element, wherein the component (D) is an inorganic filler having an average particle diameter of 0.001 to 30 ⁇ m.
- the present invention also provides the composition for sealing an organic electroluminescent element, wherein the component (D) is a flat inorganic filler.
- the present invention also provides a method for producing an organic electroluminescent device having an organic electroluminescent element sealing step including the following items 1 to 3.
- 1 Apply the above-mentioned composition for sealing an organic electroluminescence element on a lid to form a dam 2: Apply light to the dam 3: Apply an organic electroluminescence element to the lid having the dam after light irradiation Laminate the installed substrates and apply heat treatment
- the present invention also provides an organic electroluminescence device having a configuration in which a dam made of a cured product of the composition for sealing an organic electroluminescence element is disposed so as to surround the periphery of the organic electroluminescence element.
- a composition used as a dam material when an organic electroluminescence element is sealed by a dam and fill method includes the following components (A), (B), (C), and (D) A composition for encapsulating an organic electroluminescence device.
- Component (A) a cationic curable compound having two or more groups in one molecule selected from alicyclic epoxy group, oxetane ring-containing group, episulfide group, and vinyl ether group (component (C Excluding compounds that fall under)
- Component (C) At least one compound selected from N-glycidyl compounds, N-vinyl compounds, and N-allyl compounds (excluding N-glycidyl isocyanurate)
- Component (A) is (3,4,3 ', 4'-diepoxy) bicyclohexyl, bis (3,4-epoxycyclohexylmethyl) ether, 1,2-epoxy -1,2-bis (3,4-epoxycyclohexane-1-yl) ethane, 2,2-bis (3,4-epoxycyclohexane-1-yl) propane
- the compound represented by the formula (c-1) is 4,4′-methylenebis (N, N-diglycidylaniline), N, N, N ′, N′-tetraglycidyl-1,3-benzenedi (Methanamine), N, N, N ′, N′-tetraglycidyl-1,3-cyclohexanedi (methanamine), and at least one compound selected from N, N-bisglycidyl-4-glycidyloxyaniline
- the composition for organic electroluminescent element sealing as described in [6].
- the compound represented by the formula (c-2) is 1,3,4,6-tetraglycidylglycoluril and / or 1,3,4,6-tetraallylglycoluril, [6]
- the composition for organic electroluminescent element sealing of description [9] The organic electroluminescent element sealing according to any one of [1] to [8], which contains 0.05 to 3 parts by weight of the component (C) with respect to 1 part by weight of the component (B) Composition.
- composition for sealing an organic electroluminescent element according to any one of [1] to [9], further comprising the following component (E): Component (E): Compound having one or more glycidyl ether groups in one molecule (excluding compounds corresponding to component (A) and component (C)) [11]
- the component (E) is at least one compound selected from an aliphatic glycidyl ether epoxy compound, an aromatic glycidyl ether epoxy compound, and an alicyclic glycidyl ether epoxy compound.
- the component (E) is an aromatic glycidyl ether-based epoxy compound having one or more glycidyl ether groups in one molecule and having no ester bond or polyether structure.
- Composition for sealing an organic electroluminescence element [13] The content of the component (E) is 10 to 90% by weight of the total amount (100% by weight) of the curable compound contained in the composition for sealing an organic electroluminescent element, [10] to [12] The composition for organic electroluminescent element sealing as described in any one. [14] The total content of the component (A) and the component (E) is 70% by weight or more of the total amount (100% by weight) of the curable compound contained in the composition for sealing an organic electroluminescent element.
- composition for sealing an organic electroluminescent element according to any one of [13] to [13].
- the total content of the alicyclic epoxy compound represented by the formula (a) and the aromatic glycidyl ether-based epoxy compound is 100% by weight of the total amount of the curable compound contained in the composition for sealing an organic electroluminescent element (100% by weight).
- the composition for sealing an organic electroluminescent element according to any one of [10] to [14], which is 70% by weight or more of [16] The composition for sealing an organic electroluminescent element according to any one of [1] to [15], wherein the component (D) is an inorganic filler having an average particle diameter of 0.001 to 30 ⁇ m.
- composition for sealing an organic electroluminescent element according to any one of [1] to [16], wherein the component (D) is a flat inorganic filler.
- the content of component (D) is 30 to 70 parts by weight with respect to 100 parts by weight of the curable compound contained in the composition for sealing an organic electroluminescent element
- a method for producing an organic electroluminescent device comprising an organic electroluminescent element sealing step comprising the following items 1 to 3.
- 1 On the lid, the organic electroluminescent element sealing composition according to any one of [1] to [19] is applied to form a dam 2: The dam is irradiated with light 3: Light irradiation [21]
- the organic electroluminescent device which has the structure which has arrange
- the composition for sealing an organic EL device of the present invention has the above-described configuration, even if UV is applied to a dam formed by applying this on a lid, the progress of curing is suppressed until heat treatment is performed. Even if the bonding operation with the substrate provided with the organic EL element is delayed, the adhesion is not lost and the bonding is not difficult. And hardening can be advanced by performing heat processing after bonding, and it can seal, without exposing an organic EL element to UV directly. Moreover, the composition for sealing an organic EL device of the present invention can form a cured product having excellent moisture resistance and low outgassing properties, and can prevent deterioration of the organic EL device due to outgassing.
- the composition for sealing an organic EL element of the present invention can be suitably used as a dam material when sealing an organic EL element (particularly, a top emission type organic EL element) by a dam and fill method. Moreover, the organic EL device sealed by using the composition for sealing an organic EL element of the present invention as a dam material when sealing by the dam and fill method has excellent light emission characteristics and has a long life. High reliability.
- the composition for sealing an organic EL device of the present invention (hereinafter sometimes referred to as “sealing composition”) comprises the following component (A), component (B), component (C), and component (D). contains.
- Component (C) At least one compound selected from N-glycidyl compounds, N-vinyl compounds, and N-allyl compounds (excluding N-glycidyl isocyanurate)
- the alicyclic epoxy group is a group formed by bonding two adjacent carbon atoms constituting an alicyclic ring and one oxygen atom, such as a cyclohexene oxide group. Etc.
- the component (A) in the present invention is a cationic curable compound having two or more groups in one molecule selected from an alicyclic epoxy group, an oxetane ring-containing group, an episulfide group, and a vinyl ether group. And compounds corresponding to component (C) are excluded.
- alicyclic epoxy compound examples include compounds represented by the following formula (a).
- R 1 to R 18 are the same or different and are a hydrogen atom, a halogen atom, an oxygen atom, a hydrocarbon group that may contain a halogen atom, or an alkoxy that may have a substituent. Indicates a group.
- Examples of the halogen atom in R 1 to R 18 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- Examples of the hydrocarbon group in R 1 to R 18 include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group in which two or more of these are bonded through a single bond. Can do.
- Examples of the aliphatic hydrocarbon group include a C 1-20 alkyl group (preferably a C 1-10 alkyl group, particularly a methyl, ethyl, propyl, isopropyl, butyl, hexyl, octyl, isooctyl, decyl, dodecyl group).
- a C 1-4 alkyl group vinyl, allyl, methallyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl C 2-20 alkenyl group such as 5-hexenyl group (preferably C 2-10 alkenyl group, particularly preferably C 2-4 alkenyl group); C 2-20 alkynyl group such as ethynyl, propynyl group (preferably C 2-10 alkynyl group, particularly preferably C 2-4 alkynyl group).
- Examples of the alicyclic hydrocarbon group include C 3-12 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclododecyl groups; C 3-12 cycloalkenyl groups such as cyclohexenyl groups; and bicycloheptanyl. And a C 4-15 bridged cyclic hydrocarbon group such as a bicycloheptenyl group.
- aromatic hydrocarbon group examples include C 6-14 aryl groups (preferably C 6-10 aryl groups) such as phenyl and naphthyl groups.
- examples of the group in which two or more selected from the above-described aliphatic hydrocarbon group, alicyclic hydrocarbon group, and aromatic hydrocarbon group are bonded through a single bond include, for example, C such as cyclohexylmethyl group 3-12 cycloalkyl-substituted C 1-20 alkyl group; C 1-20 alkyl-substituted C 3-12 cycloalkyl group such as methylcyclohexyl group; C 7-18 aralkyl group such as benzyl group and phenethyl group (especially C 7 -10 aralkyl group); C 6-14 aryl substituted C 2-20 alkenyl group such as cinnamyl group; C 1-20 alkyl substituted C 6-14 aryl group such as tolyl group; C 2-20 alkenyl substituted such as styryl group C 6-14 aryl group and the like can be mentioned.
- C such as cyclohexylmethyl group 3-12 cycloal
- Examples of the hydrocarbon group that may contain an oxygen atom or a halogen atom in R 1 to R 18 include a group in which at least one hydrogen atom in the above-described hydrocarbon group is substituted with a group having an oxygen atom or a halogen atom, and the like Can be mentioned.
- Examples of the group having an oxygen atom include hydroxyl group; hydroperoxy group; C 1-10 alkoxy group such as methoxy, ethoxy, propoxy, isopropyloxy, butoxy, isobutyloxy group; C 2-10 such as allyloxy group.
- alkoxy group in R 1 to R 18 examples include C 1-10 alkoxy groups such as methoxy, ethoxy, propoxy, isopropyloxy, butoxy, isobutyloxy groups and the like.
- alkoxy group may have include, for example, a halogen atom, a hydroxyl group, a C 1-10 alkoxy group, a C 2-10 alkenyloxy group, a C 6-14 aryloxy group, a C 1-10 Acyloxy group, mercapto group, C 1-10 alkylthio group, C 2-10 alkenylthio group, C 6-14 arylthio group, C 7-18 aralkylthio group, carboxyl group, C 1-10 alkoxycarbonyl group, C 6- 14 aryloxycarbonyl group, C 7-18 aralkyloxycarbonyl group, amino group, mono or di C 1-10 alkylamino group, C 1-10 acylamino group, epoxy group-containing group, oxetanyl group-containing group, C 1-10 And an acyl group, an oxo group, and a group in which two or more of these are bonded through a single bond or a C 1-10 al
- X represents a single bond or a connecting group (a divalent group having one or more atoms).
- the connecting group include a divalent hydrocarbon group, an alkenylene group in which part or all of a carbon-carbon double bond is epoxidized, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide group, and Examples include a group in which a plurality of these are connected.
- Examples of the divalent hydrocarbon group include a linear or branched alkylene group having 1 to 18 carbon atoms and a divalent alicyclic hydrocarbon group.
- Examples of the linear or branched alkylene group having 1 to 18 carbon atoms include a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, and a trimethylene group.
- divalent alicyclic hydrocarbon group examples include 1,2-cyclopentylene group, 1,3-cyclopentylene group, cyclopentylidene group, 1,2-cyclohexylene group, 1,3-cyclopentylene group, Examples thereof include cycloalkylene groups (including cycloalkylidene groups) such as cyclohexylene group, 1,4-cyclohexylene group, and cyclohexylidene group.
- alkenylene group in the alkenylene group in which part or all of the carbon-carbon double bond is epoxidized include, for example, vinylene group, propenylene group, 1-butenylene group And straight or branched alkenylene groups having 2 to 8 carbon atoms such as 2-butenylene group, butadienylene group, pentenylene group, hexenylene group, heptenylene group, octenylene group, and the like.
- the epoxidized alkenylene group is preferably an alkenylene group in which all of the carbon-carbon double bonds are epoxidized, more preferably 2 to 4 carbon atoms in which all of the carbon-carbon double bonds are epoxidized. Alkenylene group.
- the connecting group in X is particularly preferably a connecting group containing an oxygen atom, specifically, —CO—, —O—CO—O—, —COO—, —O—, —CONH—; And a group in which one or more of these groups are linked to one or more of the above divalent hydrocarbon groups.
- Representative examples of the alicyclic epoxy compound represented by the above formula (a) include, for example, (3,4,3 ′, 4′-diepoxy) bicyclohexyl, bis (3,4-epoxycyclohexylmethyl) Ether, 1,2-epoxy-1,2-bis (3,4-epoxycyclohexane-1-yl) ethane, 2,2-bis (3,4-epoxycyclohexane-1-yl) propane, 1,2- Examples thereof include bis (3,4-epoxycyclohexane-1-yl) ethane and compounds represented by the following formulas (1) to (10).
- L in the following formula (5) is an alkylene group having 1 to 8 carbon atoms, and a linear or branched alkylene group having 1 to 3 carbon atoms is particularly preferable.
- N 1 to n 8 in the following formulas (5), (7), (9), and (10) are the same or different and represent an integer of 1 to 30.
- alicyclic epoxy compounds from the viewpoint of obtaining a cured product having excellent curability, heat resistance (high glass transition temperature), and low shrinkage or low linear expansion, (3,4,3) It is preferred to use ', 4'-diepoxy) bicyclohexyl and / or bis (3,4-epoxycyclohexylmethyl) ether. From the viewpoint of obtaining a cured product excellent in moisture resistance, (3,4,3 ', 4'-diepoxy) bicyclohexyl is preferred.
- Examples of the compound having two or more oxetane ring-containing groups in one molecule include 1,4-bis [(3-ethyl-3-oxetanylmethoxy) methyl] benzene, bis ⁇ [1-ethyl (3-oxetanyl).
- Examples of the compound having two or more episulfide groups in one molecule include 1,3-bis ( ⁇ -epithiopropylthio) cyclohexane, 1,3-bis ( ⁇ -epithiopropylthiomethyl) cyclohexane, bis [4- ( ⁇ -epithiopropylthio) cyclohexyl] methane, 2,2-bis [4- ( ⁇ -epithiopropylthio) cyclohexyl] propane, bis [4- ( ⁇ -epithiopropylthio) cyclohexyl] sulfide Episulfide having an alicyclic ring such as 2,5-bis ( ⁇ -epithiopropylthio) -1,4-dithiane, 2,5-bis ( ⁇ -epithiopropylthioethylthiomethyl) -1,4-dithiane, etc.
- Examples of the compound having two or more vinyl ether groups in one molecule include cyclic ether type vinyl ether compounds such as isosorbide divinyl ether and oxynorbornene divinyl ether (cyclic ether groups such as oxirane ring, oxetane ring and oxolane ring.
- a vinyl ether compound such as hydroquinone divinyl ether; a vinyl ether compound having a chain hydrocarbon group such as 1,4-butanediol divinyl ether; a chain ether type vinyl ether compound such as triethylene glycol divinyl ether; Examples thereof include vinyl ether compounds having a cyclic hydrocarbon group such as divinyl ether and cyclohexane dimethanol divinyl ether.
- Component (A) can be used alone or in combination of two or more.
- the content (blending amount) of the component (A) in the total amount (100 wt%) of the curable compound contained in the sealing composition of the present invention is, for example, about 15 to 50 wt%, preferably 20 to 40 wt%. is there.
- the component (A) is contained in the above range, the progress of the curing can be suppressed while the curing delay is desired, and it is preferable in that it is quickly cured after the heat treatment.
- content of a component (A) is less than the said range, even if it heat-processes, there exists a tendency for sufficient hardening rate to become difficult to obtain.
- the content of the component (A) exceeds the above range, a sufficient curing delay effect tends to be difficult to obtain.
- Component (B) in the present invention is a photocationic polymerization initiator that generates a cationic species upon irradiation with light and initiates the curing reaction of the cationically curable compound.
- the cationic photopolymerization initiator is composed of a cation moiety that absorbs light and an anion moiety that is a source of acid generation.
- Examples of the cationic photopolymerization initiator in the present invention include diazonium salt compounds, iodonium salt compounds, sulfonium salt compounds, phosphonium salt compounds, selenium salt compounds, oxonium salt compounds, ammonium salt compounds, bromine salts. And the like, and the like.
- the use of a sulfonium salt compound is preferable in that a cured product having excellent curability can be formed.
- Examples of the cation part of the sulfonium salt compound include arylsulfonium ions (particularly, triarylsulfonium ions) such as triphenylsulfonium ion, diphenyl [4- (phenylthio) phenyl] sulfonium ion, and tri-p-tolylsulfonium ion. Can be mentioned.
- Y represents a phenyl group or a biphenylyl group.
- Phf represents at least one hydrogen atom
- k is an integer of 0 to 3
- Rf an alkyl group in which 80% or more of hydrogen atoms are replaced by fluorine atoms, n is an integer of 1 to 5
- Examples of the photocationic polymerization initiator in the present invention include 4- (4-biphenylylthio) phenyl-4-biphenylylphenylsulfonium tetrakis (pentafluorophenyl) borate, diphenyl [4- (phenylthio) phenyl] sulfonium tetrakis ( Pentafluorophenyl) borate, diphenyl [4- (phenylthio) phenyl] sulfonium hexafluorophosphate, 4- (4-biphenylylthio) phenyl-4-biphenylylphenylsulfonium tris (pentafluoroethyl) trifluorophosphate, 4- ( Phenylthio) phenyldiphenylsulfonium phenyltris (pentafluorophenyl) borate, [4- (4-biphenylyl
- the amount of component (B) used is a cationic curable compound contained in the sealing composition of the present invention (if two or more types are contained, the total amount) 100
- the amount is, for example, about 0.05 to 4 parts by weight, preferably 0.2 to 3 parts by weight, particularly preferably 0.5 to 3 parts by weight with respect to parts by weight.
- the sealing composition of the present invention contains at least one compound selected from N-glycidyl compounds, N-vinyl compounds, and N-allyl compounds as the component (C).
- N-glycidyl compounds and the like are weakly basic with respect to cations generated from the photocationic polymerization initiator, and therefore have the effect of trapping cations generated from the photocationic polymerization initiator when irradiated with light. Until the heat treatment is performed later, the effect of suppressing the progress of curing or the effect of delaying curing is exhibited. That is, in the present invention, N-glycidyl compounds and the like are curing retarders.
- N-glycidyl compounds and the like can be used singly or in combination of two or more.
- the N-glycidyl compound or the like in the present invention is a compound having a structure in which at least one group selected from a glycidyl group, a vinyl group, and an allyl group is bonded to a nitrogen atom in a nitrogen atom-containing compound.
- the compound represented by (c-1) and the compound represented by the following formula (c-2) are included.
- R a is a group obtained by removing t hydrogen atoms from a structural formula of a hydrocarbon, a structural formula of a heterocyclic ring, or a structural formula in which a hydrocarbon and a heterocyclic ring are bonded through a single bond.
- R b is selected from a hydrogen atom, or a hydrocarbon group, a heterocyclic group, and a group in which these (two or more groups selected from a hydrocarbon group and a heterocyclic group) are bonded via a single bond.
- R c represents at least one group selected from a glycidyl group, a vinyl group, and an allyl group.
- s represents 1 or 2
- t represents an integer of 1 or more. When t is 2 or more, the groups in two or more square brackets may be the same or different.
- the ring Z represents a heterocyclic ring containing a nitrogen atom
- R c represents at least one group selected from a glycidyl group, a vinyl group, and an allyl group.
- u represents an integer of 1 or more, and when u is 2 or more, two or more nitrogen atoms contained in the ring Z may be directly bonded, and bonded via other atoms (for example, carbon atoms). You may do it.
- R a represents a group obtained by removing t hydrogen atoms from a structural formula of a hydrocarbon, a structural formula of a heterocyclic ring, or a structural formula in which a hydrocarbon and a heterocyclic ring are bonded via a single bond.
- the hydrocarbon includes an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, and a compound in which these are bonded through a single bond.
- C 1-20 aliphatic hydrocarbon is preferable.
- the alicyclic hydrocarbon is preferably a C 3-20 alicyclic hydrocarbon.
- aromatic hydrocarbon C 6-14 (particularly C 6-10 ) aromatic hydrocarbon is preferable.
- the heterocycle includes an aromatic heterocycle and a non-aromatic heterocycle.
- a heterocyclic ring a 3- to 10-membered ring (preferably a 4- to 6-membered ring) having a carbon atom and at least one hetero atom (for example, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as atoms constituting the ring. Ring) and condensed rings thereof.
- a heterocycle containing an oxygen atom as a heteroatom eg, furan ring, morpholine ring, etc.
- a heterocycle containing a sulfur atom as a heteroatom eg, thiophene ring, thiazole ring, etc.
- a nitrogen atom as a heteroatom eg, pyrrole ring, pyrrolidine ring, pyrazole ring, imidazole ring, triazole ring, isocyanuric ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, piperidine ring, piperazine ring, etc., indole ring, indoline ring, Quinoline ring, acridine ring, naphthyridine ring, quinazoline ring, purine ring, etc.).
- the hydrocarbons and heterocycles include various substituents [halogen atom, oxo group, hydroxyl group, substituted oxy group (for example, C 1-4 alkoxy group, C 6-10 aryloxy group, C 7-16 aralkyloxy group].
- C 1-4 acyloxy group, etc. carboxyl group, substituted oxycarbonyl group (eg, C 1-4 alkoxycarbonyl group, C 6-10 aryloxycarbonyl group, C 7-16 aralkyloxycarbonyl group, etc.), substituted Or an unsubstituted carbamoyl group (for example, carbamoyl, C 1-4 alkyl-substituted carbamoyl, C 6-10 aryl-substituted carbamoyl group), cyano group, nitro group, sulfo group, glycidyl ether group, etc.] may be bonded.
- an aromatic or non-aromatic heterocyclic ring may be condensed with an alicyclic hydrocarbon ring or an aromatic hydrocarbon ring.
- R a examples include aliphatic hydrocarbons, aromatic hydrocarbons, and t-valent group having 5 to 20 carbon atoms containing at least one ring selected from a heterocyclic ring.
- the hydrocarbon group for R b in the above formula includes an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group in which two or more of these are bonded through a single bond. .
- Cycloalkyl group particularly preferably about C 5-8
- cycloalkenyl group about C 3-20 (preferably C 3-15 , particularly preferably C 5-8 ) such as cyclopentenyl group, cyclohexenyl group, etc.
- a bridged cyclic hydrocarbon group such as a norbornyl group.
- the aromatic hydrocarbon group is preferably a C 6-14 (particularly C 6-10 ) aromatic hydrocarbon group, and examples thereof include a phenyl group.
- the heterocyclic group for R b in the above formula is a group obtained by removing one hydrogen atom from the structural formula of the heterocyclic ring, and examples of the heterocyclic ring include the same examples as the heterocyclic ring for R a . .
- substituents may be bonded to the above-described hydrocarbon group or heterocyclic group in the same manner as the hydrocarbon or heterocyclic ring in Ra .
- an aromatic or non-aromatic heterocyclic ring may be condensed with a ring of an alicyclic hydrocarbon group or an aromatic hydrocarbon group.
- S represents 1 or 2, and is preferably 2.
- T is an integer of 1 or more, for example, 1 to 4.
- the product of s and t (s ⁇ t) is, for example, an integer of 1 or more, and preferably 2-4.
- the ring Z is a heterocyclic ring containing a nitrogen atom, and includes, for example, a 5- to 10-membered ring (preferably a 6- to 8-membered ring) such as a pyrrolidine ring, a piperidine ring, a piperazine ring, a morpholine ring, an imidazole ring, and a glycoluril ring. Can be mentioned.
- U is an integer of 1 or more, for example, 1 to 4.
- the N-glycidyl compound can be produced, for example, by reacting a nitrogen atom-containing compound with epichlorohydrin.
- a compound represented by the following formula (c-1-1) can be produced by reacting a nitrogen atom-containing compound represented by the following formula (c-1 ′) with epichlorohydrin.
- the compound represented by -2-1) can be produced by reacting a nitrogen atom-containing compound represented by the following formula (c-2 ') with epichlorohydrin.
- R a , R b , s, and t are the same as described above.
- the rings Z and u are the same as described above.
- Examples of the nitrogen atom-containing compound represented by the formula (c-1 ′) include chain aliphatic amine compounds such as diethylamine, diethylenetriamine, triethylenetetramine, and tetraethylenepentamine; 4,4′-methylenebis (2- Cyclic aliphatic amine compounds such as methylcyclohexylamine), mensendiamine, isophoronediamine, 4,4′-methylenebis (cyclohexylamine), 1,3-bisaminomethylcyclohexane; m-xylenediamine, 2,4,6- Examples thereof include aromatic amine compounds such as tris (dimethylaminomethyl) phenol, m-phenylenediamine, diaminodiphenylmethane, and diaminodiphenylsulfone.
- chain aliphatic amine compounds such as diethylamine, diethylenetriamine, triethylenetetramine, and tetraethylenepentamine
- Examples of the nitrogen atom-containing compound represented by the above formula (c-2 ′) include nitrogen-containing heterocyclic compounds such as piperidine, pyrrolidine, morpholine, piperazine, N-aminoethylpiperazine, pyrrole, imidazole and glycoluril. be able to.
- N-vinyl compounds and N-allyl compounds can also be produced by a method according to the above-mentioned production method of N-glycidyl compounds.
- vinyl chloride is used instead of epichlorohydrin
- allyl chloride is used except that allyl chloride is used instead of epichlorohydrin.
- a method similar to the manufacturing method can be employed.
- Examples of the compound represented by the formula (c-1) include 4,4′-methylenebis (N, N-diglycidylaniline), N, N, N ′, N′-tetraglycidyl-1,3-benzenedi (Methanamine), N, N, N ′, N′-tetraglycidyl-1,3-cyclohexanedi (methanamine), N, N-bisglycidyl-4-glycidyloxyaniline and the like.
- a commercial product such as a trade name “TETRAD-X” (manufactured by Mitsubishi Gas Chemical Co., Inc.) can be used.
- Examples of the compound represented by the formula (c-2) include 1,3,4,6-tetraglycidyl glycoluril, 1,3,4,6-tetraallylglycoluril, 1,3-diallyl-4, Examples thereof include 6-diglycidyl glycoluril.
- commercially available products such as trade names “TG-G”, “TA-G”, “DAG-G” (manufactured by Shikoku Kasei Kogyo Co., Ltd.) can be used.
- the amount of component (C) used is, for example, 0.05 parts by weight with respect to 1 part by weight of component (B) contained in the sealing composition of the present invention (the total amount when containing two or more).
- the upper limit is preferably 2.5 parts by weight, particularly preferably 2.0 parts by weight, and most preferably 1.5 parts by weight.
- the lower limit is preferably 0.1 parts by weight, particularly preferably 0.2 parts by weight, and most preferably 0.3 parts by weight. It is preferable that the component (C) is contained in the above range in order to obtain a sufficient curing delay effect.
- content of a component (C) is less than the said range, there exists a tendency for sufficient hardening delay effect to become difficult to be acquired.
- the content of the component (C) exceeds the above range, a sufficient curing rate tends to be difficult to obtain even if heat treatment is performed, and curing failure may occur.
- composition for sealing of this invention contains an inorganic filler as a component (D). Therefore, a cured product having excellent moisture resistance can be obtained.
- inorganic filler examples include inorganic oxides such as silica, alumina, zinc oxide, and magnesium oxide; carbonates such as calcium carbonate and magnesium carbonate; silicic acids such as calcium silicate, glass beads, talc, clay, and mica. Examples include salts.
- silicates such as talc and mica because they have excellent linearity with respect to the coating pressure during dispensing.
- the average particle size (by laser diffraction / scattering method (microtrack method)) of the inorganic fine particles is, for example, 0.001 to 30 ⁇ m, preferably 0.1 to 10 ⁇ m.
- the shape of the inorganic filler is not particularly limited, but for example, spherical (true spherical, substantially spherical, elliptical spherical, etc.), polyhedral, rod-like (cylindrical, prismatic, etc.), flat plate, flakes, An indefinite shape can be mentioned. Especially, it is preferable to use a flat inorganic filler at the point which can provide the more superior moisture-proof property.
- the content of the inorganic filler is, for example, about 30 to 70 parts by weight, preferably 40 to 60 parts by weight, particularly preferably 45 to 60 parts by weight with respect to 100 parts by weight of the curable compound contained in the sealing composition. Part.
- a cured product having excellent moisture resistance can be obtained. If the content of the inorganic filler exceeds the above range, the viscosity becomes too high and the coating property tends to decrease. On the other hand, if the content of the inorganic filler is below the above range, the moisture resistance may be insufficient.
- the sealing composition of the present invention may contain one or more other components as necessary in addition to the above components.
- the other components include curable compounds other than the component (A), conductive materials, polymerization inhibitors, silane coupling agents, antioxidants, light stabilizers, plasticizers, leveling agents, and antifoaming agents. , Solvents, ultraviolet absorbers, ion adsorbents, pigments, phosphors, release agents and the like.
- the sealing composition of the present invention may contain one or more curable compounds other than the component (A) (excluding compounds contained in the component (C)) as the component (E). .
- Examples of the curable compound other than the component (A) include a cationic curable compound such as a compound having an epoxy group, a compound having a vinyl group, and a compound having an allyl group.
- Examples of the compound having an epoxy group include a compound having one alicyclic epoxy group in one molecule, a compound in which an epoxy group is directly bonded to the alicyclic ring by a single bond, a glycidyl ether epoxy compound, and a glycidyl ester type. Epoxy compounds and the like are included.
- Examples of the compound having one alicyclic epoxy group per molecule include 1,2: 8,9-diepoxy limonene and 1,2-epoxy-4-vinylcyclohexane.
- Examples of the compound in which an epoxy group is directly bonded to the alicyclic ring by a single bond include, for example, 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol ( Trade name "EHPE3150", manufactured by Daicel Corporation).
- glycidyl ether-based epoxy compound examples include aliphatic glycidyl ether-based epoxy obtained by reacting epichlorohydrin with an aliphatic polyhydric alcohol such as 1,6-hexanediol-diglycidyl ether or trimethylolpropane-triglycidyl ether.
- Bisphenol A type epoxy compound Bisphenol F type epoxy compound, bisphenol E type epoxy compound, o-phenylphenol glycidyl ether, biphenol type epoxy compound, phenol novolac type epoxy compound, cresol novolac type epoxy compound, cresol novolak type of bisphenol A Aromatic glycidyl ether type epoxy such as epoxy compound, naphthalene type epoxy compound, trisphenol methane type epoxy compound
- Aromatic glycidyl ether type epoxy such as epoxy compound, naphthalene type epoxy compound, trisphenol methane type epoxy compound
- An alicyclic glycidyl ether epoxy compound obtained by hydrogenating an epoxy resin can be used.
- “YL-983U” Mitsubishi Chemical Co., Ltd.
- “R1710” Printec Co., Ltd.
- “SY-OPG” Sakamoto Pharmaceutical Co., Ltd.
- Commercial products such as these can be used.
- Examples of the compound having a vinyl group include styrene compounds such as styrene, p-methylstyrene, ethylstyrene, propylstyrene, isopropylstyrene, and p-tert-butylstyrene; N-vinylcarbazole, N-vinylpyrrolidone, and the like. Examples thereof include nitrogen vinyl compounds.
- Examples of the compound having an allyl group include allyl (meth) acrylate, diallyl maleate, triallyl cyanurate, diallyl phthalate, and the like.
- a compound having an epoxy group (preferably a compound having at least one glycidyl ether group in one molecule, particularly preferably an aromatic glycidyl ether-based epoxy compound) is preferable in that the curing rate at room temperature is slow.
- an aromatic glycidyl ether-based epoxy compound having at least one glycidyl ether group in one molecule and having no ester bond or polyether structure) suppresses the generation of outgas. , which is preferable in that the effect of further stabilizing the curing retardation is obtained.
- the encapsulating composition of the present invention comprises, as component (E), a compound having an epoxy group (preferably a compound having one or more glycidyl ether groups in one molecule, particularly preferably an aromatic glycidyl ether epoxy compound). And most preferably an aromatic glycidyl ether type epoxy compound having at least one glycidyl ether group in one molecule and having no ester bond or polyether structure (corresponding to component (A) and component (C)) 1 type or 2 types or more are preferable.
- an epoxy group preferably a compound having one or more glycidyl ether groups in one molecule, particularly preferably an aromatic glycidyl ether epoxy compound.
- an aromatic glycidyl ether type epoxy compound having at least one glycidyl ether group in one molecule and having no ester bond or polyether structure (corresponding to component (A) and component (C)) 1 type or 2 types or more are preferable.
- the content of the component (E) in the total amount (100% by weight) of the curable compound contained in the sealing composition of the present invention is, for example, about 10 to 90% by weight, and the upper limit is preferably 85% by weight, particularly Preferably it is 80% by weight, most preferably 75% by weight.
- the lower limit is preferably 20% by weight, particularly preferably 30% by weight, most preferably 50% by weight, particularly preferably 60% by weight. It is preferable that the component (E) is contained in the above range in terms of stabilizing the curing retardation.
- the total content of the component (A) and the component (E) in the total amount (100% by weight) of the curable compound contained in the sealing composition of the present invention is, for example, 70% by weight or more, preferably 80% by weight. % Or more, particularly preferably 90% by weight or more.
- the upper limit is 100% by weight.
- the alicyclic epoxy compound (particularly, (3,4,3 ′, 4′-diepoxy) bicyclohexyl) and glycidyl ether in the total amount (100% by weight) of the curable compound contained in the sealing composition of the present invention.
- the total content of compounds having at least one group in one molecule is, for example, 70% by weight or more, preferably 80% by weight or more, particularly preferably 90% by weight or more. It is.
- the upper limit is 100% by weight.
- the sealing composition of the present invention contains component (A), component (B), component (C), component (D), and other components (for example, component (E)) as needed. It can be produced by uniformly mixing using a generally known mixing device such as a revolving stirring deaerator, a homogenizer, a planetary mixer, a three-roll mill, a bead mill and the like. Each component may be mixed simultaneously or sequentially.
- a generally known mixing device such as a revolving stirring deaerator, a homogenizer, a planetary mixer, a three-roll mill, a bead mill and the like. Each component may be mixed simultaneously or sequentially.
- the viscosity (25 ° C., shear rate: 20 (1 / s)) before light irradiation of the sealing composition of the present invention is, for example, about 10,000 to 2,000,000 mPa ⁇ s, preferably 20,000 to 1,500,000 mPa ⁇ s. s, particularly preferably 20,000 to 1,000,000 mPa ⁇ s, most preferably 50,000 to 800,000 mPa ⁇ s, particularly preferably 100,000 to 200,000 mPa ⁇ s.
- the sealing composition of the present invention is cured by light irradiation and then heat treatment.
- the light irradiation is preferably performed by irradiating light of 500 mJ / cm 2 or more with a mercury lamp or the like.
- the heat treatment is performed by heating in an oven or the like at 40 to 200 ° C. (particularly preferably 60 to 180 ° C., most preferably 80 to 150 ° C.) for 10 to 200 minutes (particularly preferably 30 to 120 minutes). Is preferred.
- the sealing composition of the present invention contains the component (C) having a cation trapping action, cations generated from the cationic polymerization initiator are trapped in the component (C) even when light irradiation is performed. After irradiation, the progress of cationic polymerization is suppressed until heat treatment is performed. Then, by performing heat treatment after the light irradiation, cations trapped in the component (C) are released, and cationic polymerization of the cationic curable compound proceeds to complete the curing. That is, the progress of the curing can be arbitrarily controlled by adjusting the timing for performing the heat treatment.
- the viscosity (25 ° C., shear rate: 20 (1 / s)) immediately after the sealing composition of the present invention is irradiated with ultraviolet rays (irradiation amount: 2000 mJ / cm 2 ) with a 200 W / cm mercury lamp is, for example, 10,000.
- the viscosity (25 ° C., shear rate: 20 (1 / s)) for 30 minutes after irradiation with ultraviolet rays (irradiation amount: 2000 mJ / cm 2 ) with a 200 W / cm mercury lamp is applied to the sealing composition of the present invention. It is about 10,000 to 10 million mPa ⁇ s, preferably 50,000 to 7 million mPa ⁇ s, particularly preferably 100,000 to 5 million mPa ⁇ s.
- the degree of increase in viscosity from immediately after irradiation of the sealing composition of the present invention with a 200 W / cm mercury lamp (irradiation amount: 2000 mJ / cm 2 ) to 30 minutes after irradiation is, for example, 8 times or less (for example, 1 to 8). Times), preferably 3 times or less, particularly preferably 2 times or less, and most preferably 1.5 times or less.
- the cured product obtained by curing by the above method has low water vapor permeability (that is, excellent moisture resistance), and the moisture permeability of the cured product (thickness: 100 ⁇ m) is, for example, 150 g / m 2 ⁇ day ⁇ atm. or less, preferably 100g / m 2 ⁇ day ⁇ atm or less, particularly preferably not more than 80g / m 2 ⁇ day ⁇ atm , most preferably 50g / m 2 ⁇ day ⁇ atm or less, especially preferably 20g / m 2 ⁇ day ⁇ less than atm.
- the moisture permeation amount is a value obtained by measuring the moisture permeation amount of a cured product adjusted to a thickness of 100 ⁇ m in accordance with JIS L 1099 and JIS Z 0208 under the conditions of 60 ° C. and 90% RH.
- the amount of outgas derived from the curing retarder of the cured product (60 mg) obtained by curing by the above method is about 90 ppm or less (preferably 70 ppm or less, particularly preferably 50 ppm or less), and exhibits low outgassing properties.
- the outgas amount can be measured by the head space GC / MS.
- the composition for sealing of the present invention has a retarding property and can arbitrarily adjust the curing start time. Therefore, the organic EL element is exposed to UV light by irradiating the sealing composition, and then being bonded to the organic EL element and then heating, without causing the organic EL element to be exposed to UV and without causing the bonding to be difficult. It can be sealed. Moreover, the composition for sealing of this invention forms the hardened
- the organic EL device of the present invention is a device provided with an organic EL element, in which the organic EL element is sealed using the sealing composition of the present invention, and the sealing composition of the present invention.
- the dam made of the cured product is arranged so as to surround the periphery of the organic EL element.
- the sealing composition of the present invention is used, the organic EL element (especially, top emission type organic EL element) is prevented from being deteriorated by light irradiation through the organic EL element sealing step including the following 1-3.
- an organic EL device that can be sealed and has a long life and high reliability can be manufactured.
- the light irradiation and the heat treatment method are as described above. 1: Applying the sealing composition of the present invention on a lid to form a dam 2: Applying light to the dam 3: Applying a substrate having an organic EL element to the lid having the dam after light irradiation Paste and heat treatment
- a step of filling a dam formed in 1 with a fill material after 1 in the organic EL element sealing step and before being attached to 2 is provided.
- the curable composition containing the component (B) and the component (C) in the present invention as the fill material, and in particular, the component (A), the component (B), and the component (C) in the present invention.
- component (E) preferably contains components (A), (B), (C), (E) in the same proportion as the sealing composition of the present invention).
- the viscosity (25 ° C., shear rate: 20 (1 / s)) is, for example, about 10 to 10000 mPa ⁇ s, preferably 20 to 3000 mPa ⁇ s, particularly preferably 30 to 2500 mPa ⁇ s, and most preferably 30 to 1000 mPa ⁇ s.
- Using the composition which is s has the same curing delay effect as the sealing composition (dam material) of the present invention, and can seal the organic EL device without directly exposing it to UV. This is preferable.
- the organic EL device manufacturing method of the present invention preferably includes an organic EL element sealing step including the following 1 to 4 (see FIG. 1).
- a moisture-proof substrate for example, a glass substrate such as soda glass or alkali-free glass; a metal substrate such as stainless steel or aluminum; a polyethylene trifluoride, a poly Polyfluorinated ethylene polymers such as ethylene trifluoride chloride (PCTFE), polyvinylidene fluoride (PVDF), copolymers of PCTFE and PVDF, copolymers of PVDF and polyfluoroethylene chloride, polyimide, polycarbonate, di Examples thereof include cycloolefin resins such as cyclopentadiene, polyesters such as polyethylene terephthalate, and resin base materials such as polyethylene and polystyrene.
- the substrate may be formed of the same base material or may be formed of different base materials, but the lid is different from the substrate in that no organic EL element is provided on the surface.
- the organic EL element includes an anode / light emitting layer / negative electrode laminate. If necessary, a passivation film such as a SiN film may be provided.
- the method for forming the dam by linearly applying the sealing composition of the present invention on the lid is not particularly limited, and can be performed using, for example, a dispenser.
- the height of the dam or the thickness of the sealing material layer is not particularly limited as long as the purpose of protecting the element from moisture and the like can be achieved.
- the method for filling the fill material into the dam is not particularly limited, and can be performed using, for example, a dispenser.
- the organic EL element is not directly exposed to UV because the substrate on which the organic EL element is installed is bonded. Deterioration of the organic EL element due to UV can be prevented.
- the cured product of the sealing composition of the present invention has both low outgassing properties and moisture resistance, and the organic EL device of the present invention is surrounded by an outer rim of the organic EL element by the dam made of the cured product. Therefore, the organic EL element can be prevented from being deteriorated by moisture or outgas, and excellent light emission characteristics can be maintained over a long period of time.
- the organic EL device obtained by the above method has no deterioration caused by exposure of the organic EL element to UV at the time of sealing, and is protected by a cured product having both low outgassing properties and moisture resistance. Long life and high reliability.
- the viscosity is a viscosity at 25 ° C. and a shear rate of 20 (1 / s) measured using a rheometer (trade name “Physica MCR301”, manufactured by Anton Paar).
- Example 1 In accordance with the prescription (unit: parts by weight) described in the table, each component is put into a rotating / revolving mixer (trade name “Awatori Nertaro ARE-310”, manufactured by Shinky Co., Ltd.) and stirred to seal the composition. A product (1) was obtained.
- the obtained sealing composition (1) is applied onto a glass substrate to form a coating film (1) (thickness: 100 ⁇ m) and irradiated with ultraviolet rays with a mercury lamp (irradiation amount: 1600 mJ / cm 2 ). did.
- the viscosity was measured before UV irradiation, immediately after UV irradiation, and 30 minutes after UV irradiation, and the degree of increase in viscosity was calculated from the following equation immediately after UV irradiation and after 30 minutes after UV irradiation.
- Viscosity increase viscosity for 30 minutes after UV irradiation / viscosity immediately after UV irradiation Thereafter, the coating film (1) after UV irradiation was heated at 100 ° C. for 1 hour to obtain a cured product (1) (post-cure ).
- the outgas amount and water vapor permeability were evaluated by the following method.
- Example 2 to 4 and Comparative Examples 1 to 3 A sealing composition was obtained in the same manner as in Example 1 except that the formulation was changed as described in the table, a coating film was obtained, and a cured product was obtained. About the obtained hardened
- ⁇ Outgas amount> The amount of outgas derived from the curing retarder of the cured product (unit: ppm) was determined by placing 60 mg of the cured product in a vial, leaving it under UV irradiation (2000 mJ / cm 2 ) at 100 ° C. for 1 hour, The amount of outgas in the bottle was measured.
- a calibration curve was prepared using a toluene standard solution [toluene as a standard substance: 100 ppm, solvent: hexane (60 mg)].
- a trade name “HP-6890N” manufactured by Hewlett-Packard
- DB-624 trade name (manufactured by Agilent) was used as the column.
- the moisture resistance of the cured product is such that the moisture permeability (g / m 2 ⁇ day ⁇ atm) of the cured product (thickness: 100 ⁇ m) is 60 ° C. and 90% according to JIS L 1099 and JIS Z 0208 (cup method). Measurement was performed under RH conditions.
- (Cation curable compound) (A) -1: (3,4,3 ′, 4′-diepoxy) bicyclohexyl (photocation polymerization initiator) (B) -1: 4- (4-biphenylylthio) phenyl-4-biphenylylphenylsulfonium tetrakis (pentafluorophenyl) borate (curing retarder) (C) -1: 1,3,4,6-tetraglycidylglycoluril, trade name “TG-G”, manufactured by Shikoku Chemicals Co., Ltd.
- (C) -2 1,3,4,6-tetraallyl Glycoluril, trade name “TA-G”, manufactured by Shikoku Kasei Kogyo Co., Ltd.
- (C) -3 N, N, N ′, N′-tetraglycidyl-1,3-benzenedi (methanamine), trade name “TETRAD -X ", Mitsubishi Gas Chemical Co., Ltd.
- (C) -4 Crown ether, trade name” 18-Crown-6 ", Nippon Soda Co., Ltd.
- (C) -5 Bisphenol A bis (triethylene glycol glycidyl) Ether) Ether, trade name “Rikaresin BEO-60E”, manufactured by Shin Nippon Rika Co., Ltd.
- (C) -6 1,3,5-tris (4,5-epoxypentyl) -1,3,5-triazine- 2,4,6-trione, trade name “TEPIC-VL”, manufactured by Nissan Chemical Industries, Ltd.
- (Inorganic filler) (D) -1: Talc, average particle size 1.5 ⁇ m, tabular grains, trade name “FG-15”, manufactured by Nippon Talc Co., Ltd.
- E) -1 Liquid bisphenol F diglycidyl ether, trade name “YL-983U”, manufactured by Mitsubishi Chemical Corporation
- E) -2 o-phenylphenol glycidyl ether, trade name “SY-OPG”, Sakamoto Yakuhin Made by Kogyo Co., Ltd.
- the composition for sealing an organic EL element of the present invention can suppress the progress of curing until the heat treatment is performed even if the dam formed by applying on the lid is irradiated with UV, for example, the organic EL element Even if the laminating work with the substrate provided with is delayed, the adhesiveness is lost and the laminating is not difficult. And hardening can be advanced by performing heat processing after bonding, and it can seal, without exposing an organic EL element to UV directly.
- the composition for sealing an organic EL device of the present invention can form a cured product having excellent moisture resistance and low outgassing properties, and can prevent deterioration of the organic EL device due to outgassing. Therefore, the composition for sealing an organic EL element of the present invention can be suitably used as a dam material when sealing an organic EL element (particularly, a top emission type organic EL element) by a dam and fill method. .
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Abstract
Description
成分(A):脂環エポキシ基、オキセタン環含有基、エピスルフィド基、及びビニルエーテル基から選択される1種又は2種以上の基を1分子中に2個以上有するカチオン硬化性化合物(成分(C)に該当する化合物を除く)
成分(B):光カチオン重合開始剤
成分(C):N-グリシジル化合物、N-ビニル化合物、及びN-アリル化合物から選択される少なくとも1種の化合物(N-グリシジルイソシアヌレートを除く)
成分(D):無機充填剤
で表される化合物及び/又は、下記式(c-2)
で表される化合物である前記の有機エレクトロルミネッセンス素子封止用組成物を提供する。
成分(E):グリシジルエーテル基を1分子中に1個以上有する化合物(成分(A)、及び成分(C)に該当する化合物を除く)
1:リッド上に、前記の有機エレクトロルミネッセンス素子封止用組成物を塗布してダムを形成する
2:ダムに光照射を施す
3:光照射後のダムを有するリッドに、有機エレクトロルミネッセンス素子を設置した基板を貼り合わせて加熱処理を施す
[1] ダムアンドフィル工法により有機エレクトロルミネッセンス素子を封止する際に、ダム材として使用する組成物であって、下記成分(A)、成分(B)、成分(C)、成分(D)を含有する有機エレクトロルミネッセンス素子封止用組成物。
成分(A):脂環エポキシ基、オキセタン環含有基、エピスルフィド基、及びビニルエーテル基から選択される1種又は2種以上の基を1分子中に2個以上有するカチオン硬化性化合物(成分(C)に該当する化合物を除く)
成分(B):光カチオン重合開始剤
成分(C):N-グリシジル化合物、N-ビニル化合物、及びN-アリル化合物から選択される少なくとも1種の化合物(N-グリシジルイソシアヌレートを除く)
成分(D):無機充填剤
[2] 成分(A)が、(3,4,3’,4’-ジエポキシ)ビシクロヘキシル、ビス(3,4-エポキシシクロヘキシルメチル)エーテル、1,2-エポキシ-1,2-ビス(3,4-エポキシシクロヘキサン-1-イル)エタン、2,2-ビス(3,4-エポキシシクロヘキサン-1-イル)プロパン、1,2-ビス(3,4-エポキシシクロヘキサン-1-イル)エタン、及び式(1)~(10)で表される化合物から選択される少なくとも1種の化合物である、[1]に記載の有機エレクトロルミネッセンス素子封止用組成物。
[3] 成分(A)が、(3,4,3’,4’-ジエポキシ)ビシクロヘキシル及び/又はビス(3,4-エポキシシクロヘキシルメチル)エーテルである、[1]に記載の有機エレクトロルミネッセンス素子封止用組成物。
[4] 成分(A)の含有量が、有機エレクトロルミネッセンス素子封止用組成物に含まれる硬化性化合物全量(100重量%)の15~50重量%である、[1]~[3]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[5] 成分(B)の含有量が、有機エレクトロルミネッセンス素子封止用組成物に含まれる硬化性化合物100重量部に対して0.05~4重量部である、[1]~[4]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[6] 成分(C)が、式(c-1)で表される化合物及び/又は、式(c-2)で表される化合物である、[1]~[5]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[7] 式(c-1)で表される化合物が、4,4’-メチレンビス(N,N-ジグリシジルアニリン)、N,N,N’,N’-テトラグリシジル-1,3-ベンゼンジ(メタンアミン)、N,N,N’,N’-テトラグリシジル-1,3-シクロヘキサンジ(メタンアミン)、及びN,N-ビスグリシジル-4-グリシジルオキシアニリンから選択される少なくとも1種の化合物である、[6]に記載の有機エレクトロルミネッセンス素子封止用組成物。
[8] 式(c-2)で表される化合物が、1,3,4,6-テトラグリシジルグリコールウリル及び/又は1,3,4,6-テトラアリルグリコールウリルである、[6]に記載の有機エレクトロルミネッセンス素子封止用組成物。
[9] 成分(B)1重量部に対して、成分(C)を0.05~3重量部含有する、[1]~[8]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[10] さらに、下記成分(E)を含有する、[1]~[9]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
成分(E):グリシジルエーテル基を1分子中に1個以上有する化合物(成分(A)、及び成分(C)に該当する化合物を除く)
[11] 成分(E)が、脂肪族グリシジルエーテル系エポキシ化合物、芳香族グリシジルエーテル系エポキシ化合物、及び脂環式グリシジルエーテル系エポキシ化合物から選択される少なくとも1種の化合物である、[10]に記載の有機エレクトロルミネッセンス素子封止用組成物。
[12] 成分(E)が、グリシジルエーテル基を1分子中に1個以上有し、且つエステル結合やポリエーテル構造を有さない芳香族グリシジルエーテル系エポキシ化合物である、[10]に記載の有機エレクトロルミネッセンス素子封止用組成物。
[13] 成分(E)の含有量が、有機エレクトロルミネッセンス素子封止用組成物に含まれる硬化性化合物全量(100重量%)の10~90重量%である、[10]~[12]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[14] 成分(A)と成分(E)の合計含有量が、有機エレクトロルミネッセンス素子封止用組成物に含まれる硬化性化合物全量(100重量%)の70重量%以上である、[10]~[13]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[15] 式(a)で表される脂環式エポキシ化合物と芳香族グリシジルエーテル系エポキシ化合物の合計含有量が、有機エレクトロルミネッセンス素子封止用組成物に含まれる硬化性化合物全量(100重量%)の70重量%以上である、[10]~[14]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[16] 成分(D)が、平均粒子径が0.001~30μmの無機充填剤である、[1]~[15]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[17] 成分(D)が平板状の無機充填剤である、[1]~[16]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[18] 成分(D)の含有量が、有機エレクトロルミネッセンス素子封止用組成物に含まれる硬化性化合物100重量部に対して30~70重量部である、[1]~[17]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[19] 粘度(25℃、せん断速度:20(1/s))が1万~200万mPa・sである、[1]~[18]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物。
[20] 下記1~3を含む有機エレクトロルミネッセンス素子封止工程を有する有機エレクトロルミネッセンスデバイスの製造方法。
1:リッド上に、[1]~[19]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物を塗布してダムを形成する
2:ダムに光照射を施す
3:光照射後のダムを有するリッドに、有機エレクトロルミネッセンス素子を設置した基板を貼り合わせて加熱処理を施す
[21] [1]~[19]の何れか1つに記載の有機エレクトロルミネッセンス素子封止用組成物の硬化物からなるダムを、有機エレクトロルミネッセンス素子の周辺を取り囲むように配置した構成を有する有機エレクトロルミネッセンスデバイス。
[22] 有機エレクトロルミネッセンス素子封止用組成物の硬化物の透湿量が150g/m2・day・atm以下である、[21]に記載の有機エレクトロルミネッセンスデバイス。
[23] 有機エレクトロルミネッセンス素子封止用組成物の硬化物のアウトガス量が90ppm以下である、[21]又は[22]に記載の有機エレクトロルミネッセンスデバイス。
そのため、本発明の有機EL素子封止用組成物は、有機EL素子(特に、トップ・エミッション型有機EL素子)をダムアンドフィル工法により封止する際のダム材として好適に使用することができる。
また、本発明の有機EL素子封止用組成物をダムアンドフィル工法により封止する際のダム材として使用して封止された有機ELデバイスは、優れた発光特性を有し、長寿命で信頼性が高い。
本発明の有機EL素子封止用組成物(以後、「封止用組成物」と称する場合がある)は、下記成分(A)、成分(B)、成分(C)、成分(D)を含有する。
成分(A):脂環エポキシ基、オキセタン環含有基、エピスルフィド基、及びビニルエーテル基から選択される1種又は2種以上の基を1分子中に2個以上有するカチオン硬化性化合物(成分(C)に該当する化合物を除く)
成分(B):光カチオン重合開始剤
成分(C):N-グリシジル化合物、N-ビニル化合物、及びN-アリル化合物から選択される少なくとも1種の化合物(N-グリシジルイソシアヌレートを除く)
成分(D):無機充填剤
本発明における成分(A)は、脂環エポキシ基、オキセタン環含有基、エピスルフィド基、及びビニルエーテル基から選択される1種又は2種以上の基を1分子中に2個以上有するカチオン硬化性化合物であり、成分(C)に該当する化合物は除かれる。
本発明における成分(B)は光の照射によってカチオン種を発生してカチオン硬化性化合物の硬化反応を開始させる光カチオン重合開始剤である。光カチオン重合開始剤は、光を吸収するカチオン部と酸の発生源となるアニオン部からなる。
本発明の封止用組成物は、成分(C)としてN-グリシジル化合物、N-ビニル化合物、及びN-アリル化合物から選択される少なくとも1種の化合物を含有する。N-グリシジル化合物等は光カチオン重合開始剤から発生するカチオンに対して弱塩基性を示すため、光照射を施すことにより光カチオン重合開始剤から発生するカチオンをトラップする作用を有し、光照射後に加熱処理を施すまでは硬化の進行を抑制する効果、若しくは、硬化遅延効果を発揮する。すなわち、本発明において、N-グリシジル化合物等は硬化遅延剤である。また、光照射後に加熱処理を施すとトラップしたカチオンを放出し、封止用組成物の硬化を進行させる。そのため、加熱処理を施すタイミングを調整することにより硬化の開始時期をコントロールすることができ、貼り合わせ作業の遅滞により貼り合わせが困難となる事態が発生することを防止することができる。N-グリシジル化合物等は、1種を単独で、又は2種以上を組み合わせて使用することができる。
本発明の封止用組成物は、成分(D)として無機充填材を含有する。そのため、優れた防湿性を有する硬化物が得られる。
本発明の封止用組成物は上記成分以外にも、必要に応じて他の成分を1種又は2種以上含有していても良い。前記他の成分としては、例えば、上記成分(A)以外の硬化性化合物、導電性材料、重合禁止剤、シランカップリング剤、酸化防止剤、光安定剤、可塑剤、レベリング剤、消泡剤、溶剤、紫外線吸収剤、イオン吸着体、顔料、蛍光体、離型剤等を挙げることができる。
本発明の封止用組成物は、成分(E)として、上記成分(A)以外の硬化性化合物(成分(C)に含まれる化合物も除く)を1種又は2種以上含んでいてもよい。
本発明の有機ELデバイスは、有機EL素子を備えたデバイスであって前記有機EL素子を本発明の封止用組成物を使用して封止したものであり、本発明の封止用組成物の硬化物からなるダムを、前記有機EL素子の周辺を取り囲むように配置した構成を有する。
1:リッド上に、本発明の封止用組成物を塗布してダムを形成する
2:ダムに光照射を施す
3:光照射後のダムを有するリッドに、有機EL素子を設置した基板を貼り合わせて加熱処理を施す
1:リッド(1)上に、本発明の封止用組成物を塗布してダム(2)を形成する
2:ダム(2)内に前記フィル材(4)を充填して封止材層(5)を形成する
3:封止剤層(5)に光照射を施す
4:光照射後の封止剤層(5)を有するリッド(1)に、有機EL素子(6、7、8)を設置した基板(9)を貼り合わせて加熱処理を施す
表に記載の処方(単位:重量部)に従って各成分を自転・公転ミキサー(商品名「あわとり練太郎 ARE-310」、(株)シンキー製)内に投入し、撹拌して封止用組成物(1)を得た。
粘度上昇度=紫外線照射後30分の間の粘度/紫外線照射直後の粘度
その後、紫外線照射後の塗膜(1)を100℃で1時間加熱して硬化物(1)を得た(ポストキュア)。
得られた硬化物(1)について、下記方法によりアウトガス量及び水蒸気透過性を評価した。
表に記載の通りに処方を変更した以外は実施例1と同様にして封止用組成物を得、塗膜を得、硬化物を得た。
得られた硬化物について、下記方法によりアウトガス量及び水蒸気透過性を評価した。
硬化物の硬化遅延剤由来のアウトガス量(単位:ppm)は、バイヤル瓶に硬化物60mgを入れ、UV照射(2000mJ/cm2)して100℃の条件下で1時間静置した後、バイヤル瓶中のアウトガス量を測定した。尚、トルエン標準液[標準物質としてのトルエン:100ppm、溶媒:ヘキサン(60mg)]を用いて検量線を作成した。また、測定機器としては、商品名「HP-6890N」(ヒューレット・パッカード社製)を使用し、カラムは商品名「DB-624」(アジレント社製)を使用した。
硬化物の防湿性は、硬化物(厚み:100μm)の透湿量(g/m2・day・atm)を、JIS L 1099及びJIS Z 0208(カップ法)に準じて、60℃、90%RH条件下で測定して評価した。
(カチオン硬化性化合物)
(A)-1:(3,4,3’,4’-ジエポキシ)ビシクロヘキシル
(光カチオン重合開始剤)
(B)-1:4-(4-ビフェニリルチオ)フェニル-4-ビフェニリルフェニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレート
(硬化遅延剤)
(C)-1:1,3,4,6-テトラグリシジルグリコールウリル、商品名「TG-G」、四国化成工業(株)製
(C)-2:1,3,4,6-テトラアリルグリコールウリル、商品名「TA-G」、四国化成工業(株)製
(C)-3:N,N,N’,N’-テトラグリシジル-1,3-ベンゼンジ(メタンアミン)、商品名「TETRAD-X」、三菱ガス化学(株)製
(C)-4:クラウンエーテル、商品名「18-クラウン-6」、日本曹達(株)製
(C)-5:ビスフェノールAビス(トリエチレングリコールグリシジルエーテル)エーテル、商品名「リカレジンBEO-60E」、新日本理化(株)製
(C)-6:1,3,5-トリス(4,5-エポキシペンチル)-1,3,5-トリアジン-2,4,6-トリオン、商品名「TEPIC-VL」、日産化学工業(株)製
(無機充填材)
(D)-1:タルク、平均粒子径1.5μm、平板状粒子、商品名「FG-15」、日本タルク(株)製
(D)-2:マイカ、平均粒子径3.4~5.5μm、平板状粒子、商品名「MK-100」、コープケミカル(株)製
(他のカチオン硬化性化合物)
(E)-1:液状ビスフェノールFジグリシジルエーテル、商品名「YL-983U」、三菱化学(株)製
(E)-2:o-フェニルフェノールグリシジルエーテル、商品名「SY-OPG」、阪本薬品工業(株)製
そのため、本発明の有機EL素子封止用組成物は、有機EL素子(特に、トップ・エミッション型有機EL素子)をダムアンドフィル工法により封止する際のダム材として好適に使用することができる。
2 ダム
3 ディスペンサー
4 フィル材
5 封止剤層
6 陰極
7 発光層
8 陽極
9 基板
Claims (8)
- ダムアンドフィル工法により有機エレクトロルミネッセンス素子を封止する際に、ダム材として使用する組成物であって、下記成分(A)、成分(B)、成分(C)、成分(D)を含有する有機エレクトロルミネッセンス素子封止用組成物。
成分(A):脂環エポキシ基、オキセタン環含有基、エピスルフィド基、及びビニルエーテル基から選択される1種又は2種以上の基を1分子中に2個以上有するカチオン硬化性化合物(成分(C)に該当する化合物を除く)
成分(B):光カチオン重合開始剤
成分(C):N-グリシジル化合物、N-ビニル化合物、及びN-アリル化合物から選択される少なくとも1種の化合物(N-グリシジルイソシアヌレートを除く)
成分(D):無機充填剤 - 成分(C)が、下記式(c-1)
で表される化合物及び/又は、下記式(c-2)
で表される化合物である請求項1に記載の有機エレクトロルミネッセンス素子封止用組成物。 - 成分(B)1重量部に対して、成分(C)を0.05~3重量部含有する請求項1又は2に記載の有機エレクトロルミネッセンス素子封止用組成物。
- さらに、下記成分(E)を含有する請求項1~3の何れか1項に記載の有機エレクトロルミネッセンス素子封止用組成物。
成分(E):グリシジルエーテル基を1分子中に1個以上有する化合物(成分(A)、及び成分(C)に該当する化合物を除く) - 成分(D)が、平均粒子径が0.001~30μmの無機充填剤である請求項1~4の何れか1項に記載の有機エレクトロルミネッセンス素子封止用組成物。
- 成分(D)が平板状の無機充填剤である請求項1~5の何れか1項に記載の有機エレクトロルミネッセンス素子封止用組成物。
- 下記1~3を含む有機エレクトロルミネッセンス素子封止工程を有する有機エレクトロルミネッセンスデバイスの製造方法。
1:リッド上に、請求項1~6の何れか1項に記載の有機エレクトロルミネッセンス素子封止用組成物を塗布してダムを形成する
2:ダムに光照射を施す
3:光照射後のダムを有するリッドに、有機エレクトロルミネッセンス素子を設置した基板を貼り合わせて加熱処理を施す - 請求項1~6の何れか1項に記載の有機エレクトロルミネッセンス素子封止用組成物の硬化物からなるダムを、有機エレクトロルミネッセンス素子の周辺を取り囲むように配置した構成を有する有機エレクトロルミネッセンスデバイス。
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JP2017555066A JPWO2017099055A1 (ja) | 2015-12-08 | 2016-12-06 | 封止用組成物 |
KR1020187019062A KR20180089496A (ko) | 2015-12-08 | 2016-12-06 | 밀봉용 조성물 |
CN201680069787.4A CN108293282A (zh) | 2015-12-08 | 2016-12-06 | 密封用组合物 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107884972A (zh) * | 2017-09-16 | 2018-04-06 | 合肥惠科金扬科技有限公司 | 一种液晶面板制程干燥剂涂布机的冷却组件 |
JP2019031602A (ja) * | 2017-08-07 | 2019-02-28 | 恒夫 萩原 | 光学的立体造形用樹脂組成物 |
WO2021010226A1 (ja) * | 2019-07-17 | 2021-01-21 | 積水化学工業株式会社 | 有機el表示素子用封止剤 |
WO2022270536A1 (ja) * | 2021-06-24 | 2022-12-29 | 株式会社Adeka | エポキシ樹脂組成物 |
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KR102541648B1 (ko) * | 2020-06-03 | 2023-06-08 | 삼성에스디아이 주식회사 | 유기발광소자 봉지용 조성물 및 이로부터 제조된 유기층을 포함하는 유기발광소자 표시장치 |
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2016
- 2016-12-06 CN CN201680069787.4A patent/CN108293282A/zh active Pending
- 2016-12-06 JP JP2017555066A patent/JPWO2017099055A1/ja active Pending
- 2016-12-06 WO PCT/JP2016/086168 patent/WO2017099055A1/ja active Application Filing
- 2016-12-06 KR KR1020187019062A patent/KR20180089496A/ko unknown
- 2016-12-07 TW TW105140407A patent/TW201730271A/zh unknown
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JP2001139933A (ja) * | 1999-08-12 | 2001-05-22 | Mitsui Chemicals Inc | シール剤用光硬化型樹脂組成物およびシール方法 |
JP2013157204A (ja) * | 2012-01-30 | 2013-08-15 | Sekisui Chem Co Ltd | 有機エレクトロルミネッセンス表示素子用封止剤 |
JP2014105286A (ja) * | 2012-11-28 | 2014-06-09 | Nippon Kayaku Co Ltd | 樹脂組成物及びその硬化物(2) |
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JP2019031602A (ja) * | 2017-08-07 | 2019-02-28 | 恒夫 萩原 | 光学的立体造形用樹脂組成物 |
CN107884972A (zh) * | 2017-09-16 | 2018-04-06 | 合肥惠科金扬科技有限公司 | 一种液晶面板制程干燥剂涂布机的冷却组件 |
WO2021010226A1 (ja) * | 2019-07-17 | 2021-01-21 | 積水化学工業株式会社 | 有機el表示素子用封止剤 |
WO2022270536A1 (ja) * | 2021-06-24 | 2022-12-29 | 株式会社Adeka | エポキシ樹脂組成物 |
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KR20180089496A (ko) | 2018-08-08 |
TW201730271A (zh) | 2017-09-01 |
CN108293282A (zh) | 2018-07-17 |
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