WO2014083850A1 - 樹脂組成物及びその硬化物(1) - Google Patents
樹脂組成物及びその硬化物(1) Download PDFInfo
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- WO2014083850A1 WO2014083850A1 PCT/JP2013/006982 JP2013006982W WO2014083850A1 WO 2014083850 A1 WO2014083850 A1 WO 2014083850A1 JP 2013006982 W JP2013006982 W JP 2013006982W WO 2014083850 A1 WO2014083850 A1 WO 2014083850A1
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- Prior art keywords
- compound
- skeleton
- resin composition
- group
- cyclic compound
- Prior art date
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 74
- 239000004305 biphenyl Substances 0.000 claims abstract description 53
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
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- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 28
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims abstract description 27
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- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims abstract description 7
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- 230000035699 permeability Effects 0.000 claims description 24
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 22
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- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
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- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 5
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 20
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 11
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- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 10
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- 229920006122 polyamide resin Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical class CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- KZZLKYUZEIFEIC-UHFFFAOYSA-O sulfanium bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound [C-](S(=O)(=O)C(F)(F)F)(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[SH3+] KZZLKYUZEIFEIC-UHFFFAOYSA-O 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- NNENFOSYDBTCBO-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC NNENFOSYDBTCBO-UHFFFAOYSA-M 0.000 description 1
- QEXITCCVENILJI-UHFFFAOYSA-M tributyl(phenyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)C1=CC=CC=C1 QEXITCCVENILJI-UHFFFAOYSA-M 0.000 description 1
- GLSQMJPVEVGXMZ-UHFFFAOYSA-N tributyl-(2,5-dihydroxyphenyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)C1=CC(O)=CC=C1O GLSQMJPVEVGXMZ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- ULNJZOIDTANZKR-UHFFFAOYSA-N tris[4-(4-acetylphenyl)sulfanylphenyl]sulfanium Chemical compound C1=CC(C(=O)C)=CC=C1SC1=CC=C([S+](C=2C=CC(SC=3C=CC(=CC=3)C(C)=O)=CC=2)C=2C=CC(SC=3C=CC(=CC=3)C(C)=O)=CC=2)C=C1 ULNJZOIDTANZKR-UHFFFAOYSA-N 0.000 description 1
- SOLUNJPVPZJLOM-UHFFFAOYSA-N trizinc;distiborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-][Sb]([O-])([O-])=O.[O-][Sb]([O-])([O-])=O SOLUNJPVPZJLOM-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/87—Passivation; Containers; Encapsulations
- H10K59/871—Self-supporting sealing arrangements
- H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants
Definitions
- low moisture permeability materials are important materials in various industries. Particularly in the vicinity of electric and electronic displays, it is an indispensable material for maintaining quality, and a higher performance low moisture permeability material is desired.
- thin displays called flat panel displays (FPD), in particular, plasma displays (PDP) and liquid crystal displays (LCD) have been put on the market and are widely used.
- organic EL displays OLEDs are expected as next-generation self-luminous thin film displays, and some commercial products have already been put into practical use.
- An organic EL element of an organic EL display has a structure in which an element body composed of a thin film laminate including a light emitting layer sandwiched between a cathode and an anode is formed on a glass substrate on which a driving circuit such as a TFT is formed.
- a layer such as a light emitting layer or an electrode of the element portion is easily deteriorated by moisture or oxygen, and the deterioration of brightness, life, and discoloration occurs due to the deterioration. Therefore, the organic EL element is sealed so as to block moisture or impurities from entering from the outside.
- a higher-performance sealing material is desired, and various sealing techniques have been studied.
- Patent Document 1 As a typical sealing method of an organic EL element, a method of fixing a metal or glass sealing cap in which a desiccant is inserted in advance to a substrate of an organic EL element using a sealing adhesive has been studied.
- Patent Document 1 an adhesive is applied to the outer peripheral portion of the substrate of the organic EL element, a sealing cap is placed thereon, and then the adhesive is solidified to fix the substrate and the sealing cap. It is sealed.
- sealing with a glass sealing cap is the mainstream.
- a glass sealing cap is produced by processing a digging for inserting a desiccant into a flat glass substrate, and thus tends to be expensive.
- the sealing with the sealing cap cannot extract light from the sealing cap side.
- the light emitted from the light source is extracted from the substrate side of the element, and is limited to the bottom emission type element.
- a bottom emission type element there are problems of a decrease in aperture ratio due to the drive circuit portion formed on the substrate and a decrease in extraction efficiency due to light being partially blocked by the drive circuit portion. Therefore, development of a sealing method applicable to a top emission type element that extracts light from the opposite side of the substrate of the organic EL element is desired.
- the thin film sealing method is a method in which a thin film made of an inorganic or organic material is laminated on an organic EL element to form a passivation film (Patent Document 2).
- Patent Document 2 In order to impart sufficient moisture resistance to the device by this method, it is necessary to sequentially stack a number of thin films on the device. Therefore, in the thin film sealing method, the film forming process is long and expensive, and the initial investment tends to be high due to the introduction of a large vacuum system required for film formation.
- the solid sealing method is a method in which a passivation film is provided so as to cover the entire element portion of the organic EL element, and a sealing transparent substrate is provided thereon via a sealing material.
- a passivation film is formed by vapor deposition or sputtering of an inorganic material, and it is often an incomplete film having pinholes or a film having low mechanical strength. Therefore, in the solid sealing method, after providing a passivation film on the element, a sealing transparent substrate such as a glass substrate is provided through a sealing adhesive to improve sealing reliability.
- a technique for enhancing the reliability of sealing by filling the air gap with heat or photo-curing resin has been studied. Such a solid sealing method is attracting attention as a method capable of sealing a top emission type element simply and at low cost.
- a heat or photo-curing resin as a sealing adhesive or a surface sealing adhesive. This is very important because it can significantly affect the productivity of the sealing operation. For example, if the water vapor permeability of the sealing adhesive is not sufficiently low, it may enter the element portion from the pinhole of the passivation film and cause deterioration of the element. Further, if the curing reaction of the sealing material is slow, the curing process takes time, and the productivity of the sealing work may be reduced.
- the sealing adhesive used for these has high transmittance in the visible light region, light resistance that can withstand light emission, stable moldability, low curing shrinkage for suppressing residual stress, and light emitting elements in moisture. For example, a low water vapor transmission rate for protecting from water is required.
- a sealing adhesive that can be suitably used in the solid sealing method is desired.
- Patent No. 4876609 JP 2012-059553 A Patent No. 4655172 JP 2001-81182 A JP 2011-225773 A Japanese Patent No. 4850231
- An object of the present invention is to provide a sealing material for an organic EL device, particularly a resin composition suitable for surface sealing, and excellent in visible light transmittance, light resistance and curability, high Tg, curing shrinkage rate, water vapor transmission rate. It provides a cured product having a low viscosity.
- the present invention relates to the inventions described in (1) to (25) below.
- (1) At least selected from the group consisting of a skeleton represented by formula (AA) in the following (i), a skeleton represented by formula (AB) in the following (ii), an anthracene skeleton, and a phenanthrene skeleton
- the resin composition for surface sealing of the organic EL element whose viscosity measured at 25 degreeC is 1300 mPa * s or less
- (I) Formula (AA) (In the above formula, X represents a direct bond, a sulfur atom or a dimethylmethylene group, R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and m represents an integer of 1 to
- a skeleton represented by (Ii) Formula (AB) (In the above formula, R 2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n represents an integer of 1 to 4)
- the ring in the cyclic compound (B) is an aromatic ring, an aliphatic ring or a hetero ring.
- the cyclic compound is the aromatic compound (A And (b) in the case of an aliphatic ring, the cyclic compound includes an alicyclic hydrocarbon skeleton or cycloalkylene skeleton having a bridge structure, and , A cyclic compound having an oxetanyl group or an epoxy group, or an alicyclic epoxy resin.
- the aromatic compound (A) is the following (A-1) A-1: Phenyl, biphenyl, anthracene, phenanthrene, bisphenol A, bisphenol F and bisphenol S, The resin composition according to (1), wherein the resin composition has a skeleton selected from the group described in 1. (3) The resin composition according to the above (1) or (2), wherein the aromatic compound (A) is a compound having a skeleton selected from the group consisting of phenyl, biphenyl and bisphenol A as an aromatic skeleton. .
- the cyclic compound (B) is the following (B-1), B-1: Aromatic ring, the above aliphatic ring and hetero ring, The resin composition according to any one of (1) to (3), wherein the resin composition has a ring selected from the group described in (1).
- the cycloalkylene skeleton is represented by the following formula (BA) (In the above formula, Y represents a direct bond, a sulfur atom or a methylene group, R 3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and t represents an integer of 1 to 4)
- BA formula
- Y represents a direct bond, a sulfur atom or a methylene group
- R 3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
- t represents an integer of 1 to 4
- the cyclic compound (B) is the following (B-2) B-2: Phenyl, biphenyl, naphthalene, binaphthalene, anthracene, phenanthrene, bisphenol A, bisphenol F and bisphenol S,
- the resin composition according to (7) which has a skeleton selected from the group described in
- the cyclic compound (B) is the following (B-3), B-3: Isobornyl, adamantane, cyclopentane, cyclohexane, hydrogenated bisphenol A, hydrogenated bisphenol F and hydrogenated bisphenol S,
- the cyclic compound (B) is the following (B-4), B-4: Morpholine, tetrahydrofuran, oxane, dioxane, triazine, carbazole, pyrrolidine and piperidine, The resin composition according to any one of (1) to (4), wherein the resin composition has a skeleton selected from the group described in (1).
- the cationic photopolymerization initiator is the following (C-1), C-1: sulfonium salt, iodonium salt, phosphonium salt, ammonium salt, and antimonate,
- thermosetting agent is the following (C-2), C-2: Amine compound, acid anhydride compound, amide compound, phenol compound, carboxylic acid compound, imidazole compound, isocyanuric acid adduct, metal compound, sulfonium salt, ammonium salt, antimonate, phosphonium Salt, microcapsule type curing agent,
- An organic EL display whose surface is sealed with a cured product obtained by curing the resin composition according to any one of (1) to (22).
- a film for sealing a surface of an organic EL display having a barrier performance obtained by applying and curing the resin composition according to any one of (1) to (22) above on a substrate.
- the resin composition of the present invention has a low viscosity, and its cured product is excellent in visible light transmittance and light resistance, has a high Tg, and has a low curing shrinkage and water vapor permeability. It is suitable for sealing materials, particularly surface sealing.
- aromatic compound (A) contained in the resin composition of the present invention examples include oxetane compounds and epoxy compounds exemplified below.
- the aromatic compound (A) contained in the resin composition of the present invention includes a skeleton represented by the formula (AA), a skeleton represented by the formula (AB), an anthracene skeleton, and a phenanthrene skeleton. It may be an aromatic compound (A) having at least one skeleton selected from the group consisting of, and further an oxetanyl group or an epoxy group.
- the anthracene skeleton or phenanthrene skeleton may or may not have a substituent. Examples of the substituent in the case of having an alkyl group, an alkoxy group or an alkenyl group include those having 1 to 4 carbon atoms.
- the aromatic compound (A) is represented by the following formula (AA) (In the above formula, X represents a direct bond, a sulfur atom or a dimethylmethylene group, R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and m represents an integer of 1 to 4). Or a skeleton represented by the following formula (AB) (In the above formula, R 2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n represents an integer of 1 to 4, except for the skeleton contained in the above formula (AA)).
- an aromatic compound having a skeleton selected from the group consisting of an anthracene skeleton and a phenanthrene skeleton, and an oxetanyl group or an epoxy group By combining the aromatic compound (A) (hereinafter also referred to as “component (A)”) and the above cyclic compound (B) (hereinafter also referred to as “component (B)”), an extremely excellent moisture resistance effect can be obtained. it can. This is because the skeleton serves as a sufficient barrier against moisture and prevents moisture permeation.
- X is preferably a direct bond or a dimethylmethylene group, and a direct bond (biphenyl skeleton) is particularly preferable.
- the (AA) skeleton, (AB) skeleton, anthracene skeleton or phenatrene skeleton and the oxetanyl group or epoxy group are preferably connected directly or via a hydrocarbon group.
- the hydrocarbon group includes an alkylene group having 1 to 10 carbon atoms or an alkylene group having 1 to 10 carbon atoms having an ether bond.
- the ether bond may be in the alkylene group or at either end of the alkylene group.
- an alkylene group having 1 to 4 carbon atoms (more preferably an alkylene group having 1 to 3 carbon atoms), an alkylene group having 1 to 4 carbon atoms-oxygen atom-an alkylene group having 1 to 4 carbon atoms (more preferably, a carbon number)
- An alkylene group having 2 to 10 carbon atoms (more preferably an alkylene group having 2 to 6 carbon atoms) containing an ether bond between carbon atoms, such as 1 to 3 alkylene-oxygen atom-alkylene group having 1 to 3 carbon atoms, or A C 1-4 alkylene group having an ether bond such as an oxymethyl group at the terminal of the alkylene group (-oxy-C 1-4 alkyl group, more preferably -oxy-C 1-4 alkyl group) ).
- the ether group is usually bonded to the aromatic ring, and the alkyl group is bonded to the oxetane ring or the epoxy
- the oxetane compound illustrated below can be mentioned, for example.
- epoxy compounds having a phenyl skeleton such as styrene oxide and phenyl glycidyl ether, biphenyl glycidyl ether, biphenyl diglycidyl ether, p-tert-butylphenyl glycidyl ether, 3,3 ′ , 5,5′-tetramethyl-4,4′-bis (glycidyloxy) -1,1′-biphenyl, epoxy compounds having a biphenyl skeleton such as phenyl aralkyl type epoxy compounds, biphenyl aralkyl type epoxy compounds, phenol novolac type Epoxy compounds, novolak epoxy compounds such as cresol novolac epoxy compounds, bisphenol A epoxy compounds such as bisphenol A diglycidyl ether or brominated bisphenol A diglycidyl ether Epoxy having a fluorene skeleton (preferably bisphenylfluorene skeleton)
- examples of the biphenyl aralkyl epoxy compound include those of the following formula (A-Aa).
- Formula (A-Aa) (In the above formula, G represents a glycidyl group, and p represents an integer of 1 to 50.)
- Examples of the compound of the above formula (A-Aa) include commercially available o-phenylphenol glycidyl ether (manufactured by Sanko Co., Ltd.).
- the skeleton of the component (A) include the following (A-1) A-1: phenyl, biphenyl, naphthalene, binaphthalene, anthracene, phenanthrene, bisphenol A, bisphenol F and bisphenol S, And a skeleton selected from the group described in the above.
- A-1 phenyl, biphenyl, naphthalene, binaphthalene, anthracene, phenanthrene, bisphenol A, bisphenol F and bisphenol S
- a skeleton selected from the group described in the above a skeleton selected from the group described in the above.
- a phenyl skeleton excluding the skeleton of the formula (AA), the same shall apply hereinafter
- a biphenyl skeleton, a bisphenol A skeleton, or a bisphenol S skeleton is preferable.
- a biphenyl skeleton and a bisphenol A skeleton having low viscosity and moisture permeability and excellent light transmittance.
- a biphenyl skeleton is more preferable.
- the component (A) which has one oxetanyl group or an epoxy group is preferable, More preferably, an aromatic compound (A) whose skeleton further has said preferable skeleton or a more preferable skeleton. It is. More preferred are biphenyl skeleton-containing monoepoxy compounds or monooxetanyl compounds.
- the component (A) may have either an oxetanyl group or an epoxy group, but an epoxy group is more preferable.
- More preferable aromatic compounds (A) having an epoxy group include a biphenyl skeleton-containing monoepoxy compound, a phenyl skeleton-containing monoepoxy compound such as phenylphenol glycidyl ether (more preferably o-phenylphenol glycidyl ether) or limonene oxide. Can be mentioned.
- the content of the component (A) of the present invention is 20 to 80 parts by weight, preferably 30 to 70 parts by weight, based on 100 parts by weight of the total amount of the component (A) + component (B) which is a reactive compound. is there.
- the functional group equivalent of component (A) is preferably 10 to 500 g / eq, more preferably 50 to 250 g / eq.
- Examples of the cyclic compound (B) contained in the resin composition of the present invention include an oxetane compound or an epoxy compound having an aromatic ring having a specific skeleton, an oxetane compound or an epoxy compound having an aliphatic ring having a specific skeleton, and a heterocyclic ring. Examples thereof include oxetane compounds and epoxy compounds. Examples of the ring in the cyclic compound (B) include the following (B-1), B-1: Aromatic ring, aliphatic ring and hetero ring, And a ring selected from the group described in.
- the cyclic compound (B) when an oxetane compound or an epoxy compound having an aromatic ring is selected as the cyclic compound (B), a compound having a structure different from the structure of the compound selected as the aromatic compound (A) is used. Moreover, as a cyclic compound (B), the cyclic compound (B) which has multiple (at least 2) oxetanyl group or an epoxy group normally is preferable.
- Examples of the oxetane compound or epoxy compound having an aromatic ring that can be used as the cyclic compound (B) include the same compounds as those exemplified as the aromatic compound (A). When used in combination with the aromatic compound (A), as described above, it is important to use a compound having a structure different from that of the compound used as the aromatic compound (A) as the cyclic compound (B).
- aromatic ring skeleton in the cyclic compound (B) having an aromatic ring include the following (B-2) B-2: Phenyl, biphenyl, naphthalene, binaphthalene, anthracene, phenanthrene, bisphenol A, bisphenol F and bisphenol S, And a skeleton selected from the group described in the above.
- a preferred skeleton is a skeleton selected from the group consisting of phenyl, biphenyl, naphthalene, binaphthalene, and bisphenol A. Specific compounds are listed below.
- Examples of the oxetane compound having an aromatic ring that can be used as the cyclic compound (B) include the same compounds as those described above for the component (A), and specific examples thereof include the following compounds. be able to.
- Examples of the epoxy compound having an aromatic ring that can be used as the cyclic compound (B) include the following compounds.
- epoxy compounds having a phenyl skeleton such as styrene oxide and phenyl glycidyl ether, biphenyl glycidyl ether, biphenyl diglycidyl ether, p-tert-butylphenyl glycidyl ether, 3,3 ′, 5,5′-tetramethyl-4, Epoxy compounds having a biphenyl skeleton such as 4′-bis (glycidyloxy) -1,1′-biphenyl, biphenyl aralkyl type epoxy compounds, phenol novolac type epoxy compounds, novolak type epoxy compounds such as cresol novolac type epoxy compounds, bisphenol A Biglycol A type epoxy compounds such as diglycidyl ether, brominated bisphenol A diglycidyl ether, bisphenol S diglycidyl ether, brominated bisphenol
- an aromatic ring having a structure different from the compound selected as the component (A) among the compounds, and A compound having an oxetanyl group or an epoxy group is used.
- the oxetane compound or epoxy compound having two different kinds of aromatic rings is contained in the resin composition of the present invention.
- a compound having an aromatic ring is selected as the cyclic compound (B)
- preferred examples of the skeleton including the aromatic ring include a phenyl skeleton, a biphenyl skeleton, a bisphenol A skeleton, a bisphenol F skeleton, a bisphenol S skeleton, and a naphthalene skeleton.
- a biphenyl skeleton, a bisphenol A skeleton or a naphthalene skeleton having low viscosity and moisture permeability and excellent light transmittance.
- More preferred is a biphenyl skeleton or a bisphenol A skeleton, and most preferred is a bisphenol A skeleton.
- the viscosity of these compounds is preferably 1500 mPa ⁇ s or less.
- Examples of the preferable cyclic compound (B) having an aromatic ring include the cyclic compound (B) having the above-mentioned preferable skeleton, and the more preferable skeleton, the more preferable skeleton, and the most preferable skeleton having the most preferable skeleton are: Each of these is a more preferable cyclic compound (B), a further preferable cyclic compound (B), and a most preferable cyclic compound (B).
- any of an oxetanyl group and an epoxy group may be used, but an epoxy group is usually preferable.
- the cyclic compound (B) an epoxy compound having a biphenyl skeleton or a bisphenol A skeleton is preferable, and a compound having a plurality of epoxy groups is particularly preferable.
- the content of the component (B) of the present invention is 20 to 80 parts by weight, preferably 30 to 70 parts by weight with respect to 100 parts by weight as the total of the component (A) + component (B) as the reactive compound. It is.
- the functional group equivalent of the component (B) is preferably 10 to 1000 g / eq, more preferably 50 to 500 g / eq.
- a different compound is used for a component (A) and a component (B) from the point of low moisture permeability.
- a compound having a high electron density is considered to be effective in reducing moisture permeability, but not only the electron density but also the balance with the cross-linking density between the compounds is important. Therefore, in order to reduce the moisture permeability, for example, a compound containing a phenyl skeleton, biphenyl skeleton, or bisphenol A skeleton and having one polymerizable group (oxetanyl group or epoxy group) is used as the component (A).
- a compound having a biphenyl skeleton or a bisphenol A skeleton and having one oxetanyl group or epoxy group (preferably a compound having one epoxy group) is used as the component (A).
- a compound having a phenyl skeleton, a biphenyl skeleton, or a bisphenol A skeleton as a component (B) and having a plurality of (at least two) oxetanyl groups or epoxy groups (preferably epoxy groups) or a cyclohexane skeleton-containing epoxy compound examples include the use of (for example, limonene oxide, 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexene carboxylate and hydrogenated bisphenol diglycidyl ether compound).
- hydrogenated bisphenol diglycidyl ether compound hydrogenated bisphenol A, F, or S diglycidyl ether is mentioned.
- the compounds used as these component (A) and component (B) each preferably have a viscosity of 1300 mPa ⁇ s or less, more preferably 800 mPa ⁇ s or less, and even more preferably 500 mPa ⁇ s or less.
- the cyclic compound (B) having an aliphatic ring in the cyclic compound (B) will be described in detail below.
- a cyclic compound having an aliphatic ring a cyclic compound having an alicyclic hydrocarbon skeleton having a bridge structure or a cycloalkylene skeleton, and an oxetanyl group or an epoxy group, or Use cyclic epoxy resin.
- the alicyclic hydrocarbon skeleton or cycloalkylene skeleton having a bridged structure in the above (cycloalkylene skeleton having no bridged structure) may or may not have a substituent.
- examples of the substituent include an alkyl group, an alkenyl group, and an alkoxy group, and these groups preferably have 1 to 4 carbon atoms, and more preferably have 1 to 3 carbon atoms.
- the aliphatic ring skeleton in the above cyclic compound (B) having an aliphatic ring is an alicyclic hydrocarbon skeleton having a bridge structure (preferably an alicyclic hydrocarbon having a bridge structure having 7 to 10 carbon atoms).
- Skeleton and a cycloalkylene skeleton not containing a bridge structure (preferably a cycloalkylene skeleton having 4 to 7 carbon atoms, more preferably a cycloalkylene skeleton having 5 or 6 carbon atoms, and still more preferably a cyclohexyl skeleton).
- a bridge structure preferably a cycloalkylene skeleton having 4 to 7 carbon atoms, more preferably a cycloalkylene skeleton having 5 or 6 carbon atoms, and still more preferably a cyclohexyl skeleton.
- the cyclohexylene skeleton is bonded to each other through a direct bond or a linking group, and the following formula (BA) (In the above formula, Y represents a direct bond, a sulfur atom or a methylene group, R 3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and t represents an integer of 1 to 4).
- the aliphatic ring skeleton in the cyclic compound (B) is preferably a cycloalkylene skeleton having 4 to 7 carbon atoms having no bridging structure, more preferably a cycloalkylene skeleton having 5 or 6 carbon atoms, Most preferred is a divalent cyclohexylene skeleton.
- the cyclohexylene skeleton may form a skeleton represented by the above formula (BA).
- Examples of preferable aliphatic ring skeleton in the cyclic compound (B) include the group described in B-3 below: B-3: Isobornyl, adamantane, cyclopentane, cyclohexane, hydrogenated bisphenol A, hydrogenated bisphenol F and hydrogenated bisphenol S, And, more preferably, cyclopentane, cyclohexane, hydrogenated bisphenol A, hydrogenated bisphenol F, and hydrogenated bisphenol S can be mentioned.
- the cycloalkylene skeletons not containing a crosslinked structure the cyclohexylene skeleton is most preferable.
- a cyclohexane skeleton that does not form the skeleton represented by the formula (BA) may be preferable, or a skeleton represented by the formula (BA) may be preferably formed. It can be appropriately selected and used.
- Examples of the cyclic compound (B) having an aliphatic ring used in the present invention include a cyclic compound or an alicyclic epoxy resin having the above aliphatic ring skeleton and an oxetanyl group or an epoxy group.
- a cyclic compound or an alicyclic epoxy resin having the above aliphatic ring skeleton and an oxetanyl group or an epoxy group By combining the cyclic compound (B) with the aromatic compound (A), an extremely excellent moisture resistance effect can be obtained. This is because the skeleton serves as a sufficient barrier against moisture and prevents moisture permeation.
- Preferred in the above formula (BA) skeleton is that Y has a direct bond or a methylene group, and a direct bond is particularly preferred.
- alicyclic hydrocarbon skeleton having a bridge structure examples include an adamantane skeleton, a dicyclopentadiene skeleton, and an isobornyl skeleton. In some cases, an adamantane skeleton or an isobornyl skeleton is preferable.
- Specific examples of the cycloalkylene skeleton include a cyclopentane skeleton, a cyclohexane skeleton, a cycloheptane skeleton, and the like. As described above, these two are The above formula (BA) skeleton may be formed by bonding through a direct bond or a linking group.
- the alicyclic hydrocarbon skeleton having the bridge structure, the cycloalkylene skeleton (including the (BA) skeleton), the oxetanyl group or the epoxy group may be directly or by a hydrocarbon group (which may include an ether bond). It is preferable that it is connected. As a specific connection, an oxetanyl group or an epoxy group is bonded to a hydrocarbon group, and the hydrocarbon group is connected to the aliphatic ring directly or through an ether bond.
- Examples of the hydrocarbon group when linked by a hydrocarbon group include an alkyl group having 1 to 10 carbon atoms or an alkyl group having 1 to 10 carbon atoms having an ether bond.
- the hydrocarbon group containing an ether bond as a preferred linking group is an alkylene group having 1 to 4 carbon atoms-oxygen atom-an alkylene group having 1 to 4 carbon atoms (more preferably an alkylene group having 1 to 3 carbon atoms-oxygen atom- An alkylene group having 2 to 10 carbon atoms (more preferably an alkylene group having 2 to 6 carbon atoms) containing an ether bond such as an alkylene group having 1 to 3 carbon atoms) or an ether bond such as an -oxymethyl group.
- Examples include an alkylene group having 1 to 4 carbon atoms (-oxy-alkyl group having 1 to 4 carbon atoms) (more preferably -oxy-alkyl group having 1 to 3 carbon atoms) at the end of the alkylene group.
- the alkylene group has an ether bond at the terminal, the ether group is usually bonded to an aliphatic ring, and the alkyl group is bonded to an oxetane ring or an epoxy ring.
- the epoxy group may be directly formed in the aliphatic ring like alicyclic epoxy resin.
- Examples of such an epoxy compound having an aliphatic ring include limonene oxide, an alicyclic epoxy resin described in formula (b-1a), formula (b-1b) and formula (b-1c) described later, and hydrogenated bisphenol.
- Bisphenol F type epoxy compounds such as A epoxy compound, hydrogenated bisphenol F diglycidyl ether, brominated hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol S diglycidyl ether, bisphenol S such as brominated hydrogenated bisphenol S diglycidyl ether
- Type epoxy compounds epoxy compounds having a tricyclodecane skeleton such as diepoxy tricyclodecane, tricyclodecane diglycidyl ether, and epoxy compounds having an adamantane skeleton such as adamantane glycidyl ether.
- N is an average value and represents a positive number from 1 to 5.
- the compound having an aliphatic ring in the cyclic compound (B) is preferably an alicyclic epoxy resin or a cyclic compound (B) having a skeleton selected from the group consisting of an isobornyl skeleton, an adamantane skeleton and a hydrogenated bisphenol A skeleton.
- Particularly preferred is an alicyclic epoxy resin or a cyclic compound (B) having an adamantane skeleton because it is colorless and excellent in reactivity and has a high glass transition point.
- the content of the cyclic compound (B) having an aliphatic ring of the present invention is 20 to 80 parts by mass with respect to 100 parts by mass of the total amount of the component (A) + component (B) as the reactive compound, preferably 30 to 70 parts by mass.
- the functional group equivalent of the cyclic compound (B) is preferably 10 to 1000 g / eq, more preferably 50 to 500 g / eq.
- heterocyclic ring examples include morpholine skeleton, tetrahydrofuran skeleton, oxane skeleton, dioxane skeleton, triazine skeleton, carbazole skeleton, pyrrolidine skeleton, and piperidine skeleton. These may have a substituent or may not have a substituent, and when having a substituent, examples of the substituent include an alkyl group, an alkoxy group, and an alkenyl group. Usually it has about 1 to 4 carbon atoms.
- the heterocyclic skeleton and the oxetanyl group or epoxy group may be directly bonded or linked by a divalent hydrocarbon group, but are usually linked by a divalent hydrocarbon group. Yes.
- the hydrocarbon group in the case of being connected by a hydrocarbon group include an alkylene group having 1 to 10 carbon atoms or an alkylene group having 1 to 10 carbon atoms having an ether bond.
- Examples of the oxetane compound having a heterocycle include a reaction product of isocyanuric acid (CIC acid) and oxetane alcohol.
- Examples of the epoxy compound having a heterocyclic ring include epoxy compounds such as a compound having an isocyanurate skeleton such as 1,3,5-triglycidyl isocyanurate and a compound having a dioxane glycol skeleton such as dioxane glycol diglycidyl ether.
- the component (B) having a heterocyclic ring a compound having an isocyanurate skeleton is preferable, and a reaction product of CIC acid and oxetane alcohol, 1,3,5-triglycidyl isocyanurate is particularly preferable.
- the content of the component (B) having a heterocycle is 20 to 80 parts by weight, preferably 30 to 70 parts by weight, based on 100 parts by weight of the total amount of the component (A) + component (B) as the reactive compound. It is.
- the functional group equivalent of the component (B) is preferably 10 to 500 g / eq, more preferably 50 to 250 g / eq.
- This invention is the curable resin composition containing the said component (A) and the said component (B), and demonstrates a suitable combination as a combination of these components below.
- the component (A) or the component (B) has a weight average molecular weight of 2000 or less, more preferably 1000 or less, and particularly preferably 500 or less to obtain a curable resin composition. It is preferable.
- a low molecular weight component for either component (A) or component (B), it has a low viscosity and is easy to spread after coating and has excellent composition for producing OLEDs. This is because things can be obtained.
- thermosetting it is also preferable that one of the component (A) and the component (B) is an oxetane compound. It is because the resin composition excellent in sclerosis
- the viscosity of the resin composition is usually 1500 mPa ⁇ s or less, preferably 1300 mPa ⁇ s or less, more preferably 1200 mPa ⁇ s or less. It is preferable that when the component (A) and the component (B) are mixed, the viscosity is not more than the above.
- the component (A) contains a biphenyl skeleton and a monofunctional aromatic compound having one oxetanyl group or epoxy group, preferably a biphenyl skeleton-containing epoxy compound having one epoxy group (preferably a biphenyl skeleton). Containing monoglycidyl ether), more preferably o-phenylphenol glycidyl ether, and a polyfunctional cyclic compound (B) having at least two oxetanyl groups or epoxy groups as component (B) is preferred.
- the polyfunctional cyclic compound (B) is aromatic in consideration of the viscosity of the resin composition, low water vapor permeability of the cured product, low cure shrinkage, high Tg of the cured product, and the like.
- a cyclic compound (B) having a ring or a non-bridged aliphatic ring is preferred.
- the polyfunctional cyclic compound (B) has a viscosity of 1400 mPa ⁇ s or less, preferably 1350 mPa ⁇ s or less, and a skeleton represented by the above formula (AA) as an aromatic ring skeleton, or
- a cyclic compound (B) having a cycloalkane skeleton having 5 to 7 carbon atoms and having no crosslinking is preferred.
- the viscosity is 1400 mPa ⁇ s or less, preferably 1350 mPa ⁇ s or less, and has a skeleton represented by the above formula (AA) as an aromatic ring skeleton, and has at least two epoxy groups.
- An epoxy compound or an alicyclic epoxy resin having at least two epoxy groups more preferably a polyglycidyl ether compound having a viscosity of 1350 mPa ⁇ s or less and having a biphenyl skeleton or a bisphenol A skeleton, and 3, 4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexenecarboxylate.
- an oxetane compound or an epoxy compound having a condensed ring structure such as fluorene or carbazole can also be used as the cyclic compound (B).
- the alicyclic epoxy resin as the component (B) is preferable from the viewpoint of good workability because of its low viscosity and excellent curing speed.
- alicyclic epoxy compounds a bifunctional alicyclic epoxy is preferable, and 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexenecarboxylate is particularly preferable.
- the oxetane compound or epoxy compound which has condensed ring structures, such as fluorene and carbazole other than a component (A) and a component (B), can also be used as needed, and can provide rigidity to a coating film. .
- These oxetane compounds or epoxy compounds may be used alone or in combination of two or more.
- the curing agent (C) contained in the resin composition of the present invention is reactive with the component (A) and / or (B).
- a compound that causes a curing reaction by energy rays such as light or heat can be used.
- any of them can be used, but usually a curing agent (C) that causes a curing reaction with energy rays is preferable.
- the curing agent (C) that causes a curing reaction with energy rays such as light can be used without limitation as long as it is a compound that generates a cation by receiving ultraviolet rays (wavelength of about 200 to 400 nm), for example, a cationic polymerization initiator, particularly light.
- a cationic polymerization initiator include sulfonium salts, iodonium salts, phosphonium salts, ammonium salts, and antimonates.
- sulfonium salt examples include triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrakis (pentafluorophenyl) borate, 4,4′-bis [diphenylsulfonio] diphenyl sulfide-bishexafluorophosphate, 4,4′-bis [di ( ⁇ -hydroxyethoxy) phenylsulfonio] diphenyl sulfide-bishexafluoroantimonate, 7- [di (p-toluyl) sulfonio] -2-isopropylthioxanthone hexafluorophosphate, 7- [ Di (p-toluyl) sulfonio] -2-isopropylthioxanthone hexafluoroantimonate
- Examples of the iodonium salt include diphenyliodonium tetrakis (pentafluorophenyl) borate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, di (4-nonylphenyl) iodonium hexafluorophosphate, (triccumyl) iodonium tetrakis (pentafluorophenyl) Examples include borate.
- Examples of the phosphonium salt include tri-n-butyl (2,5-dihydroxyphenyl) phosphonium bromide, hexadecyltributylphosphonium chloride, and the like.
- ammonium salts include benzyltrimethylammonium chloride, phenyltributylammonium chloride, and benzyltrimethylammonium bromide.
- Antimonates include triphenylsulfonium hexafluoroantimonate, p- (phenylthio) phenyldiphenylsulfonium hexafluoroantimonate, 4-chlorophenyldiphenylsulfonium hexafluoroantimonate, bis [4- (diphenylsulfonio) phenyl]. Examples thereof include sulfide bishexafluoroantimonate and diallyl iodonium hexafluoroantimonate.
- the curing agent (C) photo cationic polymerization initiator
- iodonium salts and sulfonium salts are preferable, and among them, they are highly sensitive and easily available from the market.
- diphenyl [4- (phenylthio) phenyl] sulfonium trifluorotrispentafluoro which does not contain antimony element
- ethyl phosphate tris [4- (4-acetylphenylsulfanyl) phenyl] sulfonium tris [(trifluoromethyl) sulfonyl] methanide is used.
- the content of the photocationic polymerization initiator of the present invention is 0.05 to 5 parts by mass, preferably 0.1 to 3 parts by mass with respect to 100 parts by mass as a total of component (A) + component (B). is there.
- a photocationic polymerization initiator may be used independently and may be used in mixture of multiple types.
- thermosetting agent examples include amine compounds, acid anhydride compounds, amide compounds, phenol compounds, carboxylic acid compounds, and the like.
- specific examples of the curing agent that can be used include diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylsulfone, isophoronediamine, dicyandiamide, polyamide resin synthesized from linolenic acid and ethylenediamine, phthalic anhydride, trimellitic anhydride Acid, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl nadic anhydride, nadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, butanetetracarboxylic anhydride, Bicyclo [2,2,1] heptane-2,3-dicarboxylic acid
- an acid anhydride having excellent transparency after curing for sealing in a sealing material particularly an organic EL
- methyltetrahydrophthalic anhydride, methyl nadic anhydride, anhydrous nadic anhydride are often used.
- Acid hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, butanetetracarboxylic anhydride, bicyclo [2,2,1] heptane-2,3-dicarboxylic anhydride, methylbicyclo [2,2,1] heptane
- An acid anhydride having an alicyclic skeleton such as -2,3-dicarboxylic acid anhydride and cyclohexane-1,3,4-tricarboxylic acid-3,4-anhydride is preferable.
- these acid anhydrides having an alicyclic skeleton commercially available products can be used.
- the H-TMA series from Mitsubishi Gas Chemical Co., Ltd.
- the curing agent that can be used in combination is not particularly limited as long as it is liquid and has a low viscosity.
- curing agents include methyl nadic anhydride and nadic anhydride.
- examples of the curing agent include HNA-100 contained (manufactured by Shin Nippon Rika Co., Ltd.) and Rikacid MH700 (manufactured by Shin Nippon Rika Co., Ltd.) containing hexahydrophthalic anhydride and methylhexahydrophthalic anhydride.
- a solid or semi-solid cyclohexane-1,3,4-tricarboxylic acid-3,4-anhydride and a curing agent having a low viscosity in advance or at room temperature or warming (as heating conditions) In order to prevent volatilization of the curing agent, it is preferably 150 ° C. or lower, more preferably 120 ° C.) until mixing becomes uniform until the workability is improved.
- the use ratio of cyclohexane-1,3,4-tricarboxylic acid-3,4-anhydride in the total curing agent is 20 to 90 mass. %, More preferably in the range of 30 to 80% by mass or less. When the mixing ratio exceeds 90% by weight, workability as a curing agent is extremely inferior. On the other hand, when the amount is less than 20% by mass, the improvement effect may be reduced in terms of the depression of the sealing material.
- the compounding ratio of the system using the thermosetting agent of the present invention is determined by the functional group equivalent contained in the epoxy compound or oxetane compound and the equivalent of the carboxyl group of the carboxylic acid curing agent.
- the carboxyl group is 0.2 to 5 equivalents, more preferably 0.5 to 2 equivalents with respect to 1 equivalent of the functional group. If it exceeds this range, the curing reaction does not proceed sufficiently, and excess functional groups and carboxyl groups remain, so that the toughness and heat resistance of the cured product cannot be fully exhibited.
- a curing catalyst can be used in combination with a curing agent, or a curing catalyst can be used alone without using a curing agent.
- the curing accelerator that can be used include 2-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenyl-4-methylimidazole, and 1-benzyl-2-phenylimidazole.
- curing accelerator which of these curing accelerators is used is appropriately selected depending on characteristics required for the obtained transparent resin composition, such as transparency, curing speed, and working conditions.
- a thermal cationic initiator is preferred, and a phosphonium salt thermal cationic initiator is particularly preferred.
- the curing accelerator is usually used in the range of 0.001 to 15 parts by mass, preferably 0.01 to 5 parts by mass, relative to 100 parts by mass of the total amount of component (A) + component (B).
- a redox reaction using a cleavage type photopolymerization initiator used in a radical polymerization system is also effective.
- the reactivity of an iodonium salt having a low level of LUMO minimum empty orbit: a measure of the ease of the occurrence of an electron transfer reaction
- Any photopolymerization initiator may be used as long as it is a cleavage type photopolymerization initiator, and examples thereof include 2-hydroxy-2-methyl-phenylpropan-1-one and 1-hydroxycyclohexyl-phenylketone.
- the curing agent used in the present invention it is preferable to cure at 100 ° C. or less, and a thermal cationic polymerization initiator is suitably used in consideration of the reaction rate and the thermal history of the constituent members. It is also preferable to use a cationic photopolymerization initiator that does not require heat energy.
- Fine particles can be used in combination with the resin composition of the present invention as necessary.
- the fine particles include organic fine particles and inorganic fine particles.
- the fine particles can be used singly or in combination of plural kinds in consideration of required light transmittance, hardness, scratch resistance, curing shrinkage rate, and refractive index.
- Organic fine particles that can be used in the present invention include polystyrene resin beads, acrylic resin beads, urethane resin beads, organic resin beads such as polycarbonate resin beads, porous polystyrene resin beads, porous acrylic resin beads, porous Porous organic polymer beads such as urethane resin beads and porous polycarbonate resin beads, resin powder of benzoguanamine-formalin condensate, resin powder of benzoguanamine-melamine-formalin condensate, resin powder of urea-formalin condensate, aspartic acid ester derivative Powder, zinc stearate powder, stearamide powder, epoxy resin powder, polyethylene powder, etc., such as crosslinked polymethyl methacrylate resin beads and crosslinked polymethyl methacrylate / styrene. Resin beads and the like are preferable. These organic fine particles can be easily obtained as a commercial product, and can also be prepared with reference to known literature.
- inorganic fine particles examples include conductive metal oxides, transparent metal oxides, and other inorganic fillers.
- Examples of the conductive metal oxide that can be used in the present invention include zinc antimonate, tin oxide-doped indium oxide (ITO), antimony-doped tin oxide (ATO), antimony pentoxide, tin oxide, aluminum-doped zinc oxide, and gallium. Examples include doped zinc oxide and fluorine-doped tin oxide.
- Examples of the transparent metal oxide that can be used in the present invention include silica, titanium oxide, zirconium oxide, cerium oxide, zinc oxide, iron oxide, titanium oxide / zirconium oxide / tin oxide / antimony pentoxide composite, zirconium oxide / Examples thereof include a tin oxide / antimony pentoxide composite and a titanium oxide / zirconium oxide / tin oxide composite.
- inorganic fillers that can be used in the present invention include calcium oxide, calcium chloride, zeolite, silica gel and the like.
- the fine particles that can be used in the present invention are preferably fine particles having excellent hardness and scratch resistance and a high refractive index. Titanium oxide, zirconium oxide, cerium oxide, zinc oxide, iron oxide, titanium oxide / zirconium oxide / tin oxide / Monium pentoxide composite, zirconium oxide / tin oxide / antimony pentoxide composite, and titanium oxide / zirconium oxide / tin oxide composite are preferably used.
- the primary particle diameter of the fine particles is preferably 100 nm or less. The blending ratio of these is 1 to 30 parts by mass, preferably 5 to 20 parts by mass with respect to 100 parts by mass of the total amount of component (A) + component (B).
- a fine particle dispersant a polycarboxylic acid dispersant, a silane coupling agent, a titanate coupling agent, a silicone dispersant such as a modified silicone oil, or an organic copolymer dispersant may be used in combination. Is possible. When blending these, the blending ratio is about 0.001 to 30% by mass, preferably about 0.05 to 5% by mass, with respect to the total mass of the resin composition of the present invention.
- the primary particle size means the smallest particle size of the particles when the aggregation is broken. That is, in the case of elliptical fine particles, the minor axis is the primary particle diameter.
- the primary particle size can be measured by a dynamic light scattering method, observation with an electron microscope, or the like. Specifically, using a JSM-7700F field emission scanning electron microscope manufactured by JEOL Ltd., the primary particle size can be measured under an acceleration voltage of 30 kV.
- fine particles can be used by dispersing in a solvent.
- inorganic fine particles are readily available as commercial products in a form dispersed in water or an organic solvent.
- organic solvents used include aromatic hydrocarbon solvents such as toluene, xylene, ethylbenzene, and tetramethylbenzene, hexane, and octane.
- Aliphatic hydrocarbon solvents such as decane, and mixtures thereof such as petroleum ether, white gasoline, solvent naphtha, etc.
- ester solvents include alkyl acetates such as ethyl acetate, propyl acetate and butyl acetate, and ⁇ -butyrolactone Cyclic esters such as ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether monoacetate, diethylene glycol monoethyl ether monoacetate, triethylene glycol monoethyl ether monoacetate, diethylene glycol monoacetate (Mono or poly) alkylene glycol monoalkyl ether monoacetates such as tilether monoacetate, propylene glycol monomethyl ether monoacetate, butylene glycol monomethyl ether monoacetate, polycarboxylic acids such as dialkyl glutarate, dialkyl succinate, dialkyl adipate Alkyl esters, etc., ether solvents include alkyl ethers such as diethyl ether and ethyl butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethy
- the resin composition of the present invention uses a reactive compound in addition to the component (A) and the component (B) in consideration of the viscosity, refractive index, adhesion and the like of the resin composition of the present invention to be obtained. May be.
- Specific examples include (meth) acrylates.
- the (meth) acrylates include monofunctional (meth) acrylates, difunctional (meth) acrylates, and polymers having three or more (meth) acryloyl groups in the molecule.
- Functional (meth) acrylate, polyester (meth) acrylate, epoxy (meth) acrylate, and the like can be used.
- Examples of monofunctional (meth) acrylates include isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, and cyclohexyl (meth) acrylate.
- (Meth) acrylate having a heterocyclic ring such as alicyclic (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, morpholine (meth) acrylate, benzyl (meth) acrylate, Ethoxy-modified cresol (meth) acrylate, propoxy-modified cresol (meth) acrylate, neopentyl glycol benzoate (meth) acrylate, o-phenylphenol (meth) acrylate O-phenylphenol monoethoxy (meth) acrylate, o-phenylphenol polyethoxy (meth) acrylate, p-phenylphenol (meth) acrylate, p-phenylphenol monoethoxy (meth) acrylate, p-phenylphenol polyethoxy (Meth) acrylate, o-
- the (meth) acrylate monomer having two functional groups includes (meth) acrylate having a heterocycle such as hydropivalaldehyde-modified trimethylolpropane di (meth) acrylate, (poly) ethoxy-modified bisphenol A di (meth) acrylate , (Poly) propoxy modified bisphenol A di (meth) acrylate, (poly) ethoxy modified bisphenol F di (meth) acrylate, (poly) propoxy modified bisphenol F di (meth) acrylate, (poly) ethoxy modified bisphenol S di (meta) ) Acrylate, (poly) propoxy-modified bisphenol S di (meth) acrylate, hexahydrophthalic acid di (meth) acrylate, bisphenoxy (poly) ethoxyfluorene and other (meth) acrylates, bif Nyldimethanol di (meth) acrylate and other heterocyclic (meth) acryl
- polyfunctional (meth) acrylate monomer examples include polyfunctional (meth) acrylate having an isocyanurate ring such as tris (acryloxyethyl) isocyanurate, (poly) caprolactone-modified tris (acryloxyethyl) isocyanurate, pentaerythritol tri ( (Meth) acrylate, pentaerythritol tetra (meth) acrylate, (poly) ethoxy modified pentaerythritol tetra (meth) acrylate, (poly) propoxy modified pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, (poly) Caprolactone-modified dipentaerythritol penta (meth) acrylate, (poly) ethoxy-modified dipentaerythritol penta (meth) acryl
- urethane (meth) acrylate examples include diol compounds (for example, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,4-butanediol, neopentyl glycol, 1,6- Hexanediol, 1,8-octanediol, 1,9-nonanediol, 2-methyl-1,8-octanediol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentane Diol, 2-butyl-2-ethyl-1,3-propanediol, cyclohexane-1,4-dimethanol, polyethylene glycol, polypropylene glycol, bisphenol A polyethoxydiol, bisphenol A polypropoxydio Or a reaction product of these diol compounds with a dibasic acid or
- Polyester diol and organic polyisocyanate for example, chain saturated hydrocarbon isocyanate such as tetramethylene diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, isophorone diisocyanate
- chain saturated hydrocarbon isocyanate such as tetramethylene diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, isophorone diisocyanate
- Norbornane diisocyanate dicyclohexylmethane diisocyanate, methylenebis (4-cyclohexylisocyanate), hydrogenated diphenylmethane diisocyanate, hydrogenated xylene diisocyanate
- Cyclic saturated hydrocarbon isocyanates such as hydrogenated toluen
- polyester (meth) acrylate examples include a polyester diol which is a reaction product of a diol compound and a dibasic acid or an anhydride thereof, and a reaction product of (meth) acrylic acid.
- (meth) acrylate that can be used for the resin composition of the present invention, a material having a low curing shrinkage rate is suitably used.
- (meth) acrylate having a ring structure is preferable, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, Cyclohexyl (meth) acrylate, p-cumylphenol (poly) ethoxy (meth) acrylate, naphthol (poly) ethoxy (meth) acrylate, naphthol (poly) propoxy (meth) acrylate, phenylphenol (poly) ethoxy (meth) acrylate , Phenylphenol (poly) propoxy (meth) acrylate, benzyl (meth) acrylate, tricyclodecan
- phenylphenol (poly) ethoxy (meth) acrylate Particularly preferred are phenylphenol (poly) ethoxy (meth) acrylate, tricyclodecane dimethanol (meth) acrylate, hydropivalaldehyde-modified trimethylolpropane di (meth) acrylate having a high Tg of the cured product and a low cure shrinkage rate.
- Biphenyldimethanol di (meth) acrylate in the resin composition of this invention, (meth) acrylate which is another component may be used independently, and multiple types may be mixed and used for it.
- the amount of (meth) acrylate is 10 to 200 parts by weight, preferably 50 to 150 parts by weight, with 100 parts by weight of component (A) + component (B). It is.
- benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isobutyl ether; acetophenone, 2,2-diethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone 1,1-dichloroacetophenone, 2-hydroxy-2-methyl-phenylpropan-1-one, diethoxyacetophenone, 1-hydroxycyclohexyl-phenylketone, 2-methyl-1- [4- (methylthio) phenyl]- Acetophenones such as 2-morpholinopropan-1-one and oligo [2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propanone]; 2-ethylanthraquinone, 2-ter
- acetophenones Preferred are acetophenones, and more preferred are 2-hydroxy-2-methyl-phenylpropan-1-one and 1-hydroxycyclohexyl-phenyl ketone.
- the radical polymerization initiator it is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the (meth) acrylate component. More preferably, it is 1 to 5 parts by mass.
- a photoinitiator may be used independently and may be used in mixture of multiple types.
- each component of the resin composition of the present invention is determined in consideration of a desired refractive index, durability, viscosity, adhesion, and the like.
- component (A) + component (B) is 100 parts by mass
- the content of component (A) is 20 to 80 parts by mass, preferably 30 to 70 parts by mass.
- the content of the component (B) is 20 to 80 parts by mass, preferably 30 to 70 parts by mass.
- the content of component (C) is 0.05 to 5 parts by mass, preferably 0.1 to 3 parts by mass in the case of a thermal cation initiator.
- the total amount of component (A) + component (B) is preferably about 50 to 99% by mass, more preferably 70 to 99% by mass, based on the total amount of the resin composition of the present invention.
- the amount is preferably 80 to 99% by mass, and in some cases, 90 to 99% by mass, and further 95 to 99% by mass may be used.
- the balance is the above component (C) and optional additive components.
- the resin composition of the present invention includes a mold release agent, an antifoaming agent, a leveling agent, a light stabilizer, an antioxidant, a polymerization inhibitor, and a plasticizer in order to improve convenience during handling. Further, an antistatic agent or the like can be used in combination depending on the situation.
- a plasticizer is used to obtain durability and flexibility.
- the material used is selected depending on the desired viscosity, durability, transparency, flexibility and the like.
- olefinic polymers such as polyethylene and polypropylene, dimethyl phthalate, diethyl phthalate, dibutyl phthalate, bis (2-ethylhexyl) phthalate, diisodecyl phthalate, butyl benzyl phthalate, diisononyl phthalate, dicyclohexyl phthalate, ethyl phthalyl ethyl glycolate Phthalates such as butyl phthalyl butyl glycolate, trimellitic esters such as tris (2-ethylhexyl) trimellitate, dibutyl adipate, diisobutyl adipate, bis (2-ethylhexyl) adipate, diisononyl adipate, diisode
- a coupling agent may be added for the purpose of improving the adhesive strength.
- silane coupling agents include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltri Methoxysilane, N-phenyl- ⁇ -aminopropyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) 3-aminopropyltrimethoxysilane, 3-amino Propyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, vinyltrimethoxysilane, N- (2- (vinyl)
- silane coupling agents are preferred, and aminosilane coupling agents or epoxysilane coupling agents are more preferred.
- a coupling agent By using a coupling agent, it is possible to obtain a sealing material that is excellent in moisture resistance reliability and has little decrease in adhesive strength after moisture absorption.
- the content of such a coupling agent is about 0.05 to 3 parts by mass with respect to 100 parts by mass of the reactive resin composition.
- polymers such as acrylic polymer, polyester elastomer, urethane polymer and nitrile rubber can be added as necessary.
- a weight average molecular weight is 10,000 g / mol from a compatible point.
- An organometallic compound such as alkylaluminum can also be added to reduce the water vapor permeability.
- a solvent can also be added, what does not add a solvent is preferable.
- the weight average molecular weight of each component is preferably 10,000 g / mol or less, and more preferably 5,000 g / mol or less. Since the component having a large weight average molecular weight does not dissolve, the prepared resin composition becomes a turbid liquid. This is incompatible because it is essential that the resin composition used in the display is uniformly transparent. Further, excellent characteristics are also required for the transmittance, and specifically, the light transmittance at each wavelength in the wavelength range of 380 to 780 nm is preferably 90% or more. The light transmittance can be measured with a measuring instrument such as a spectrophotometer U-3900H manufactured by Hitachi High-Technologies Corporation.
- the resin composition of the present invention can be prepared by mixing and dissolving each component according to a conventional method.
- each component can be charged into a round bottom flask equipped with a stirrer and a thermometer and stirred at 40 to 80 ° C. for 0.5 to 6 hours.
- the viscosity of the resin composition of the present invention needs to be a viscosity suitable for workability in processability when producing a display or the like, particularly a viscosity suitable for surface sealing in an organic EL device.
- An organic EL element is usually surrounded by a dam material, and a metal electrode, an organic carrier transport layer, an organic EL light emitting layer, an ITO electrode, and a passivation film are laminated on a substrate such as glass in this order from the substrate side.
- the passivation film is filled with a fill material (surface sealing resin composition), and the top is further sealed with a sealing substrate such as glass.
- the fill material fills the space between the metal electrode side substrate and the sealing substrate on the opposite side and protects the organic light emitting layer from external moisture and the like, and is usually a curable resin.
- a sealing substrate such as glass is usually placed, and then the resin composition is cured to seal the organic light emitting layer.
- the resin composition used as the fill material is a surface sealing resin composition. Therefore, the resin composition preferably has a low viscosity so that the gap between the substrates can be completely sealed.
- the viscosity is preferably 1.5 Pa ⁇ s (1500 mPa ⁇ s) or less at 25 ° C., more preferably 1300 mPa, as measured using an E-type viscometer (TV-200: manufactured by Toki Sangyo Co., Ltd.).
- ⁇ S or less more preferably 700 mPa ⁇ s or less, and particularly preferably 400 mPa ⁇ s or less.
- a resin composition containing a curing agent that causes a curing reaction with energy rays can be easily cured with energy rays.
- energy rays include electromagnetic waves such as ultraviolet rays, visible rays, infrared rays, X-rays, gamma rays and laser rays, particle rays such as alpha rays, beta rays and electron rays.
- ultraviolet rays, laser beams, visible rays, or electron beams are preferred in the present invention.
- the cured product of the present invention can be obtained by irradiating the resin composition of the present invention with the energy beam.
- the liquid refractive index of the resin composition of the present invention is usually 1.45 to 1.70, preferably 1.50 to 1.65.
- the refractive index can be measured with an Abbe refractometer (model number: DR-M2, manufactured by Atago Co., Ltd.).
- the resin composition of the present invention preferably has a smaller shrinkage ratio (curing shrinkage ratio) at the time of curing, preferably 5% or less, more preferably 4% or less, and still more preferably 3.5. % Or less.
- the cured product of the resin composition of the present invention has a water vapor transmission rate of 50 g / m 2 ⁇ 24 h (measured at 60 ° C. and 90% humidity, the same shall apply hereinafter) in order to protect the organic light emitting layer from external moisture and the like.
- it is preferably 35 g / m 2 ⁇ 24 h or less, more preferably 30 g / m 2 ⁇ 24 h or less, and still more preferably less than 30 g / m 2 ⁇ 24 h.
- the glass transition temperature of the cured product is preferably higher to some extent.
- the Tg is preferably 40 ° C. or higher, more preferably 45 ° C. or higher, and most preferably 50 ° C. or higher.
- the aromatic compound (A) is at least one skeleton selected from the group consisting of the skeleton represented by the formula (AA), the skeleton represented by the formula (AB), an anthracene skeleton, and a phenanthrene skeleton.
- an aromatic compound (A) having an oxetanyl group or an epoxy group
- the cyclic compound (B) is a group described in the following B-2 or a group B-2 described in the following B-3: phenyl, biphenyl, naphthalene, binaphthalene, anthracene, phenanthrene, bisphenol A, bisphenol F, and bisphenol S.
- B-3 Isobornyl, adamantane, cyclopentane, cyclohexane, hydrogenated bisphenol A, hydrogenated bisphenol F and hydrogenated bisphenol S, A cyclic compound having at least one skeleton selected from the above, an oxetanyl group or an epoxy group, or an alicyclic epoxy resin, Aromatic compound (A), cyclic compound (B) (however, in the case of a skeleton selected from the group described in B-2, the compound used as aromatic compound (A) is a different compound) and curing agent The resin composition for surface sealing of the organic EL element containing (C). ii.
- any one of the aromatic compound (A) and the cyclic compound (B) contains a compound having at least one oxetanyl group or epoxy group.
- iii The resin composition according to the above i or ii, wherein the aromatic compound (A) is an aromatic compound (A) having a skeleton selected from the group consisting of phenyl, biphenyl and bisphenol A as an aromatic skeleton.
- iv The resin composition according to any one of the above i to iii, wherein the aromatic compound (A) includes an aromatic compound (A) having one oxetanyl group or epoxy group.
- the aromatic compound (A) includes an aromatic compound (A) having one epoxy group.
- the cyclic compound (B) (A) a skeleton selected from the group consisting of phenyl, biphenyl, naphthalene, binaphthalene and bisphenol A, or (B) a skeleton B-3 selected from the group described in (B-3) below: isobornyl, adamantane, cyclopentane, cyclohexane, hydrogenated bisphenol A, hydrogenated bisphenol F, and hydrogenated bisphenol S;
- the cyclic compound (B) is a cyclic compound (B) having a skeleton selected from the group consisting of phenyl, biphenyl, bisphenol A, cyclopentane, cyclohexane and hydrogenated bisphenol A.
- xi The resin composition according to any one of i to x above, wherein the cyclic compound (B) has a viscosity of 1500 mPa ⁇ s or less.
- xii The resin composition according to the above xi, containing bisphenol A diglycidyl ether having a viscosity of 1500 mPa ⁇ s or less as the cyclic compound (B).
- xiii The resin composition according to any one of i to xii above, which contains an alicyclic epoxy resin as the cyclic compound (B).
- xiv The resin composition according to any one of i to xiii above, wherein the viscosity of the resin composition is 1500 mPa ⁇ s or less.
- xv The resin composition according to xiv, wherein the viscosity of the resin composition is preferably 1300 mPa ⁇ s or less.
- xvi The resin composition according to any one of the above i to xv, wherein the cured product has a thickness of 100 ⁇ m, and the cured product has a water vapor permeability of 35 g / m 2 ⁇ 24 hr or less measured at 60 ° C. and a relative humidity of 90%. object.
- xvii The resin composition according to any one of i to xii above, wherein the viscosity of the resin composition is 1500 mPa ⁇ s or less.
- xv The resin composition according to xiv, wherein the viscosity of the resin composition is preferably 1300 mP
- xviii The resin composition according to any one of the above i to xvii, which has a curing shrinkage rate of 4% or less.
- xix The resin composition according to any one of the above i to xvii, wherein the liquid refractive index of the resin composition is 1.54 to 1.7.
- xx The resin composition according to any one of the above i to xix, wherein the glass transition point (Tg) of the cured product of the resin composition is 45 ° C. or higher.
- xxii. The resin composition according to any one of i to xxi above, wherein the ratio of aromatic compound (A): cyclic compound (B) is from 3: 7 to 7: 3.
- xxiii. The resin composition according to any one of the above i to xxi, wherein the ratio of the aromatic compound (A): the cyclic compound (B) is 3.5: 6.5 to 6.5: 3.5.
- xxiv The resin composition according to any one of i to xxi above, wherein the curing agent (C) is a photocationic polymerization initiator.
- Photocationic polymerization initiators are (tricumyl) iodonium tetrakis (pentafluorophenyl) borate, diphenyl [4- (phenylthio) phenyl] sulfonium trifluorotrispentafluoroethyl phosphate and tris [4- (4-acetylphenylsulfanyl) phenyl]
- the resin composition as described in xxiv above which is a compound selected from the group consisting of sulfonium tris [(trifluoromethyl) sulfonyl] methanide.
- the aromatic compound (A) is o-phenylphenol glycidyl ether
- the cyclic compound (B) has a viscosity of 1500 mPa ⁇ s or less, bisphenol A diglycidyl ether, xylylene bisoxetane, 3,3 ′, 5,5 ′ -Tetramethyl-4,4'-bis (glycidyloxy) -1,1'-biphenyl, biphenylaralkyl polyglycidyl ether, 3,4-epoxycyclohexenylmethyl-3 ', 4'-epoxycyclohexene carboxylate, water
- the resin composition according to any one of i to xxv above, which is a compound selected from the group consisting of bisphenol A diglycidyl ether and limonene oxide.
- the cyclic compound (B) is composed of bisphenol A diglycidyl ether, 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexene carboxylate, and hydrogenated bisphenol A diglycidyl ether having a viscosity of 1500 mPa ⁇ s or less.
- the organic EL device solid sealing method includes a step of forming a passivation film on an organic EL device formed on a substrate, a surface sealing resin composition is applied on the passivation film, and sealing is performed. And a step of curing the surface sealing resin composition, wherein the curable resin composition according to the present invention is used as the sealing resin composition. .
- the organic EL element to be sealed includes a substrate, a lower electrode, an organic EL layer including at least a light emitting layer, and an element unit body including an upper electrode.
- the substrate is a flat substrate made of an electrically insulating material such as a glass substrate, a transparent organic material made of cycloolefin, polycarbonate, polymethyl methacrylate, or the like, or an organic / inorganic hybrid transparent substrate made of the transparent organic material made of high-rigidity glass fiber or the like.
- a simple substrate is used.
- the following are mentioned as a typical structure of an element part main body.
- a lower electrode made of an Al—Li alloy or the like is deposited on one side of a substrate by resistance heating vapor deposition.
- an organic EL layer an electron transport layer composed of an oxadiazole derivative or a triazole derivative, a light emitting layer, TPD (N, N′-diphenyl-N, N′-bis (3- methylphenyl) -1,1-biphenyl-. 4, 4′-diaminine) and the like, and an upper electrode (anode) can be sequentially laminated by a thin film forming method such as a resistance heating vapor deposition method or an ion beam sputtering method.
- the layer structure or material of the organic EL element is not particularly limited as long as it functions as a display element.
- the solid sealing method according to the present invention can be applied to any structure of organic EL elements.
- the passivation film is formed so as to cover the organic EL element.
- the passivation film can be formed by a method such as vapor deposition or sputtering of an inorganic material such as silicon nitride or silicon oxide.
- the passivation film is provided to prevent moisture, ionic impurities, and the like from entering the organic EL element.
- the thickness of the passivation film is preferably in the range of 10 nm to 100 ⁇ m, and more preferably in the range of 100 nm to 10 ⁇ m.
- the passivation film may be laminated for the purpose of improving reliability.
- Passivation films are generally incomplete films with pinholes or films with low mechanical strength, although depending on the deposition method. Therefore, in the solid sealing method, the reliability of sealing is improved by further applying an adhesive on the passivation film, press-bonding using a transparent substrate for sealing, and curing the adhesive.
- the ultraviolet curable resin compositions of the examples and comparative examples and the cured products thereof were obtained with the compositions as shown in the following examples and comparative examples.
- the evaluation method and evaluation criteria for the resin composition and the cured film were as follows.
- Viscosity was measured at 25 ° C. using an E-type viscometer (TV-200: manufactured by Toki Sangyo Co., Ltd.).
- Liquid refractive index The refractive index (25 ° C.) of the blended resin composition was measured with an Abbe refractometer (DR-M2: manufactured by Atago Co., Ltd.).
- Tg Glass transition point: Tg point of cured energy ray or thermosetting resin layer at viscoelasticity measurement system EXSTAR DMS-6000 (manufactured by SII Nanotechnology Co., Ltd.), tensile mode, frequency 1 Hz It was measured.
- Curing shrinkage rate Resin composition by applying an energy ray or thermosetting resin layer on a substrate and irradiating 3000 mJ / cm 2 with a high-pressure mercury lamp (80 W / cm, ozone-less) or heating at 100 ° C. for 1 hour in a dryer.
- the product was cured to produce a cured product for film specific gravity measurement. This was measured based on JIS K7112 B method, and the specific gravity (DS) of the cured product was measured. Further, the specific gravity (DL) of the resin composition was measured at 23 ⁇ 2 ° C., and the cure shrinkage rate was calculated by the following formula. A measurement result is shown by the average value of four measurement results.
- Curing shrinkage (%) (DS ⁇ DL) / DS ⁇ 100 (6)
- Workability A seal pattern was applied on a clean glass substrate using a dispenser (SHOTMASTER: manufactured by Musashi Engineering Co., Ltd.) with a thickness of 5 ⁇ m KAYATORON Z-5536.
- the resin compositions of Examples and Comparative Examples were dropped into the seal pattern frame using a dispenser in the same manner as the seal pattern.
- another clean glass substrate was bonded to the resin composition-dropped substrate in a vacuum using a bonding apparatus. Thereafter, the film was opened to the atmosphere, a gap was formed, UV irradiation (integrated light quantity: 3000 mJ / cm 2 ) was cured, and the sample was put in an oven at 120 ° C.
- Evaluation criteria The dropping liquid spreads quickly in the cell, and the resin composition is uniformly filled in the cell without any gaps. ⁇ : Spreading of the dropping liquid into the cell is slightly slow, but the resin composition is uniformly filled in the cell without any gaps. X: The dropping liquid does not spread sufficiently in the cell, a gap is formed in the cell, and the resin composition is not uniformly filled.
- OPP-G Sanko Co., Ltd. o-phenylphenol glycidyl ether
- OXT-121 Toagosei Co., Ltd.
- xylylene bisoxetane jER-828 Mitsubishi Chemical Corporation bisphenol A diglycidyl ether
- EP-4088S ADEKA Corporation di Cyclopentadiene dimethanol diglycidyl ether YX-4000H: 3,3 ′, 5,5′-tetramethyl-4,4′-bis (glycidyloxy) -1,1′-biphenyl KAYARAD NC-3000H manufactured by Mitsubishi Chemical Corporation : Nippon Kayaku Co., Ltd.
- biphenylaralkyl polyglycidyl ether SEJ-01R Nippon Kayaku Co., Ltd. 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexene carboxylate GSID 26-1: BASF Japan Ltd.
- the resin composition of the present invention having a specific composition has a high Tg, a low curing shrinkage, and a low water vapor permeability. Therefore, it is suitable, for example, as a coating material for barrier films and various sealing materials, particularly as a surface sealing material for organic EL elements.
- the resin composition of the present invention and its cured product are excellent in visible light transmittance and light resistance, have a high Tg, and have a low curing shrinkage and water vapor permeability. Suitable for fastening materials.
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Abstract
Description
近年、ディスプレイはフラットパネルディスプレイ(FPD)と称される薄型のディスプレイ、特にプラズマディスプレイ(PDP)、液晶ディスプレイ(LCD)が市場投入され広く普及している。また、次世代の自発光型薄膜ディスプレイとして有機ELディスプレイ(OLED)が期待されており、一部製商品では既に実用化されている。有機ELディスプレイの有機EL素子は、TFT等の駆動回路が形成されたガラス等の基板上に、陰極および陽極によって挟持された発光層を含む薄膜積層体からなる素子部本体が形成された構造を有している。素子部の発光層または電極といった層は、水分または酸素により劣化し易く、劣化によって輝度やライフの低下、変色が発生する。その為、有機EL素子は、外部からの水分または不純物の浸入を遮断するように封止されている。高品質で高信頼性の有機EL素子の実現に向けて、より高性能な封止材料が望まれており、従来から種々封止技術が検討されている。
(1)下記(i)の式(A-A)で表される骨格、下記(ii)の式(A-B)で表される骨格、アントラセン骨格及びフェナントレン骨格からなる群から選択される少なくとも一つの骨格と、更に、オキセタニル基またはエポキシ基とを有する芳香族化合物(A)、及び、オキセタニル基またはエポキシ基を有し、下記(iii)の条件を満たす環状化合物(B)を含有し、且つ、25℃で測定した粘度が1300mPa・s以下である有機EL素子の面封止用の樹脂組成物、
(i)式(A-A)
(上記式中、Xは直接結合、硫黄原子またはジメチルメチレン基を、R1は水素原子または炭素数1~4のアルキル基を表し、mは1~4の整数を示す。)、
で表される骨格、
(ii)式(A-B)
(上記式中、R2は水素原子または炭素数1~4のアルキル基を表し、nは1~4の整数を示す)
で表される骨格、
(iii)該環状化合物(B)の条件:
該環状化合物(B)における環は、芳香族環、脂肪族環またはヘテロ環であり、これらの中で環が、(a)芳香族環の場合、該環状化合物は、前記芳香族化合物(A)として使用される化合物とは異なる構造を有する化合物であり、また、(b)脂肪族環の場合、該環状化合物は、橋架け構造を有する脂環式炭化水素骨格又はシクロアルキレン骨格と、及び、オキセタニル基またはエポキシ基とを有する環状化合物、又は、脂環式エポキシ樹脂である。
A-1:フェニル、ビフェニル、アントラセン、フェナントレン、ビスフェノールA、ビスフェノールF及びビスフェノールS、
に記載の群から選択される骨格を有する上記(1)に記載の樹脂組成物。
(3)芳香族化合物(A)が、芳香族骨格として、フェニル、ビフェニル及びビスフェノールAからなる群から選択される骨格を有する化合物である上記(1)または上記(2)に記載の樹脂組成物。
B-1:芳香族環、上記脂肪族環及びヘテロ環、
に記載の群から選択される環を有する上記(1)乃至上記(3)の何れか一項に記載の樹脂組成物。
(上記式中、Yは直接結合、硫黄原子またはメチレン基を、R3は水素原子または炭素数1~4のアルキル基を表し、tは1~4の整数を示す)
で表される骨格を形成している上記(1に記載の樹脂組成物。
(6) 環状化合物(B)が脂環式エポキシ樹脂である上記(1)に記載の樹脂組成物。
(8)環状化合物(B)が下記(B-2)
B-2:フェニル、ビフェニル、ナフタレン、ビナフタレン、アントラセン、フェナントレン、ビスフェノールA、ビスフェノールF及びビスフェノールS、
に記載の群から選択される骨格を有する上記(7)に記載の樹脂組成物、
(10)環状化合物(B)が下記(B-3)、
B-3:イソボルニル、アダマンタン、シクロペンタン、シクロヘキサン、水添ビスフェノールA、水添ビスフェノールF及び水添ビスフェノールS、
に記載の群から選択される骨格を有する上記(1)乃至上記(4)の何れか一項に記載の樹脂組成物。
(12)環状化合物(B)が下記(B-4)、
B-4:モルホリン、テトラヒドロフラン、オキサン、ジオキサン、トリアジン、カルバゾール、ピロリジン及びピペリジン、
に記載の群から選択される骨格を有する上記(1)乃至上記(4)の何れか一項に記載の樹脂組成物。
(16)前記光カチオン重合開始剤が下記(C-1)、
C-1:スルホニウム塩、ヨードニウム塩、ホスホニウム塩、アンモニウム塩、及びアンチモン酸塩、
に記載の群から選択される少なくとも一つである上記(15)に記載の樹脂組成物。
(18)前記熱硬化剤が下記(C-2)、
C-2:アミン系化合物、酸無水物系化合物、アミド系化合物、フェノール系化合物、カルボン酸系化合物、イミダゾール系化合物、イソシアヌル酸付加物、金属化合物、スルホニウム塩、アンモニウム塩、アンチモン酸塩、ホスホニウム塩、マイクロカプセル型硬化剤、
に記載の群から選択される上記(17)に記載の樹脂組成物。
(20)芳香族化合物(A)と環状化合物(B)の総量を100質量部に対して、環状化合物(B)を20~80質量部含有する上記(1)乃至上記(19)の何れか一項に記載の樹脂組成物。
(21)芳香族化合物(A)と環状化合物(B)の総量を100質量部とした場合に硬化剤(C)を0.1~5質量部含有する上記(1)乃至上記(20)の何れか一項に記載の樹脂組成物。
(24)上記(1)乃至上記(22)の何れか一項に記載の樹脂組成物を基材上に塗布、硬化させてなるバリア性能を有する有機ELディスプレイの面封止用のフィルム。
尚、本発明においてアントラセン骨格又はフェナントレン骨格は置換基を有していても、有していなくてもよい。有している場合の置換基としてはアルキル基、アルコキシ基またはアルケニル基を挙げることができ、これらの基は、何れも炭素数1~4が好ましい。
本発明においては、芳香族化合物(A)として、下記式(A-A)
(上記式中、Xは直接結合、硫黄原子またはジメチルメチレン基を、R1は水素原子または炭素数1~4のアルキル基を表し、mは1~4の整数を示す。)
で表される骨格、または下記式(A-B)
(上記式中、R2は水素原子または炭素数1~4のアルキル基を表し、nは1~4の整数を示す。但し、上記式(A-A)に含まれる骨格を除く。)
で表される骨格、アントラセン骨格及びフェナントレン骨格からなる群から選択される骨格と、オキセタニル基またはエポキシ基とを有する芳香族化合物、を使用する。
該芳香族化合物(A)(以下成分(A)ともいう)と前記の環状化合物(B)(以下成分(B)ともいう)とを組み合わせることで、極めて優れた耐湿性の効果を得ることができる。上記の骨格が水分に対して十分なバリアとなり、透湿を防ぐためである。
上記式(A-A)骨格において好ましいものは、Xが直接結合ないしジメチルメチレン基を有するものであり、直接結合のもの(ビフェニル骨格)が特に好ましい。
上記骨格に、オキセタニル基またはエポキシ基が炭化水素基により連結されている場合、該炭化水素基としては、炭素数1~10のアルキレン基または、エーテル結合を有する炭素数1~10のアルキレン基が挙げられる。エーテル結合は、該アルキレン基の中であっても、該アルキレン基のいずれかの末端にあっても良い。好ましくは、炭素数1~4のアルキレン基(より好ましくは炭素数1~3のアルキキレン基)、炭素数1~4のアルキレン-酸素原子-炭素数1~4のアルキレン基(より好ましくは炭素数1~3のアルキキレン-酸素原子-炭素数1~3のアルキレン基)等のエーテル結合を炭素原子間に含む炭素数2~10のアルキレン基(より好ましくは2~6のアルキレン基)、または、-オキシメチル基などのエーテル結合をアルキレン基の末端に有する炭素数1-4のアルキレン基(-オキシ-炭素数1-4のアルキル基、より好ましくは-オキシ-炭素数1-4のアルキル基)である。エーテル結合を末端に有する場合、通常、エーテル基が芳香環に結合し、アルキル基がオキセタン環またはエポキシ環に結合する。
例えば、1,4-ビス{[(3-エチル-3-オキセタニル)メトキシ]メチル}ベンゼン、3-エチル-3-フェノキシメチルオキセタン、キシリレンビスオキセタン、1,4-ビス[(3-エチルオキセタン-3-イル)メトキシ]ベンゼン、1,3-ビス[(3-エチルオキセタン-3-イル)メトキシ]ベンゼン、1,2-ビス[(3-エチルオキセタン-3-イル)メトキシ]ベンゼン、4,4’-ビス[(3-エチルオキセタン-3-イル)メトキシ]ビフェニル、2,2’-ビス[(3-エチル-3-オキセタニル)メトキシ]ビフェニル、3,3’,5,5’-テトラメチル[4,4’-ビス(3-エチルオキセタン-3-イル)メトキシ]ビフェニル、2,7-ビス[(3-エチルオキセタン-3-イル)メトキシ]ナフタレン、4,4’-ビス[(1-エチル-3-オキセタニル)メチル]チオジベンゼンチオエーテル酸等のオキセタン化合物を挙げることができる。
ここで、ビフェニルアラルキルエポキシ化合物の例としては、下記式(A-Aa)のものが挙げられる。
式(A-Aa)
(上記式中、Gはグリシジル基を、pは1~50の整数を表す。)
上記式(A-Aa)の化合物としては、市販のo-フェニルフェノールグリシジルエーテル(三光株式会社製)等を挙げることができる。
A-1:フェニル、ビフェニル、ナフタレン、ビナフタレン、アントラセン、フェナントレン、ビスフェノールA、ビスフェノールF及びビスフェノールS、
に記載の群から選択される骨格を挙げることができる。
本発明の樹脂組成物では、前記成分(A)の上記の骨格の中でもフェニル骨格(式(A-A)の骨格を除く、以下同じ)、ビフェニル骨格、ビスフェノールA骨格又はビスフェノールS骨格が好ましい。より好ましくは、粘度、透湿度が低く、光線透過率に優れるビフェニル骨格、ビスフェノールA骨格である。上記の中でも、ビフェニル骨格が更に好ましい。
また、前記成分(A)としては、オキセタニル基又はエポキシ基を1つ有する成分(A)が好ましく、より好ましくは、更に、骨格が上記の好ましい骨格又はより好ましい骨格を有する芳香族化合物(A)である。更に好ましくは、ビフェニル骨格含有モノエポキシ化合物又はモノオキセタニル化合物である。
前記成分(A)としては、オキセタニル基又はエポキシ基の何れかを有すればよいが、エポキシ基がより好ましい。
エポキシ基を有する更に好ましい芳香族化合物(A)としては、ビフェニル骨格含有モノエポキシ化合物、フェニル骨格含有モノエポキシ化合物、例えば、フェニルフェノールグリシジルエーテル(より好ましくはo-フェニルフェノールグリシジルエーテル)又はリモネンオキサイドを挙げることができる。
本発明の成分(A)の含有量は反応性化合物である成分(A)+成分(B)の総量100質量部に対して、20~80質量部であり、好ましくは30~70質量部である。また、低透湿度を達成する為には成分(A)の官能基当量が10~500g/eqが好ましく、50~250g/eqがさらに好ましい。
環状化合物(B)における環としては、下記(B-1)、
B-1:芳香環、脂肪族環及びヘテロ環、
に記載の群から選ばれる環を挙げることができる。
ここで、環状化合物(B)として芳香環を有するオキセタン化合物またはエポキシ化合物を選択する場合は、芳香族化合物(A)として選択した化合物の構造とは異なる構造を有する化合物を用いるものとする。
また、環状化合物(B)としては、通常、オキセタニル基又はエポキシ基を複数(少なくとも2個)有する環状化合物(B)が好ましい。
芳香環を有する環状化合物(B)における具体的な芳香環骨格としては、下記(B-2)
B-2:フェニル、ビフェニル、ナフタレン、ビナフタレン、アントラセン、フェナントレン、ビスフェノールA、ビスフェノールF及びビスフェノールS、
に記載の群から選択される骨格を挙げることができる。これらの中で好ましい骨格としては、フェニル、ビフェニル、ナフタレン、ビナフタレン、及びビスフェノールAからなる群から選択される骨格である。
以下具体的な化合物について列挙する。
例えば、1,4-ビス{[(3-エチル-3-オキセタニル)メトキシ]メチル}ベンゼン、3-エチル-3-フェノキシメチルオキセタン、キシリレンビスオキセタン、1,4-ビス[(3-エチルオキセタン-3-イル)メトキシ]ベンゼン、1,3-ビス[(3-エチルオキセタン-3-イル)メトキシ]ベンゼン、1,2-ビス[(3-エチルオキセタン-3-イル)メトキシ]ベンゼン、4,4’-ビス[(3-エチルオキセタン-3-イル)メトキシ]ビフェニル、2,2’-ビス[(3-エチル-3-オキセタニル)メトキシ]ビフェニル、3,3’,5,5’-テトラメチル[4,4’-ビス(3-エチルオキセタン-3-イル)メトキシ]ビフェニル、2,7-ビス[(3-エチルオキセタン-3-イル)メトキシ]ナフタレン、4,4’-ビス[(1-エチル-3-オキセタニル)メチル]チオジベンゼンチオエーテル酸等が挙げられる。
例えば、スチレンオキサイド、フェニルグリシジルエーテル等のフェニル骨格を有するエポキシ化合物、ビフェニルグリシジルエーテル、ビフェニルジグリシジルエーテル、p-tert-ブチルフェニルグリシジルエーテル、3,3’,5,5’-テトラメチル-4,4’-ビス(グリシジルオキシ)-1,1’-ビフェニル、ビフェニルアラルキル型エポキシ化合物等のビフェニル骨格を有するエポキシ化合物、フェノールノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物等のノボラック型エポキシ化合物、ビスフェノールAジグリシジルエーテル、臭素化ビスフェノールAジグリシジルエーテル等のビスフェノールA型エポキシ化合物、ビスフェノールSジグリシジルエーテル、臭素化ビスフェノールSジグリシジルエーテル等のビスフェノールS型エポキシ化合物、ビスフェニルフルオレンジグリシジルエーテル、ビスフェニルフルオレンエタノールジグリシジルエーテル等のフルオレン骨格を有するエポキシ化合物、グリシジルオキシナフタレン、1,6-ビス(2,3-エポキシプロパン-1-イルオキシ)ナフタレン、ビナフタレングリシジルエーテル、ビナフタレンジグリシジルエーテル、ビナフトールエタノールジグリシジルエーテル等のナフタレン骨格を有するエポキシ化合物等を挙げることができる。
環状化合物(B)として芳香環を有する化合物を選択する場合、該芳香環を含む好ましい骨格としては、フェニル骨格、ビフェニル骨格、ビスフェノールA骨格、ビスフェノールF骨格、ビスフェノールS骨格又はナフタレン骨格等を挙げることができる。より好ましくは、粘度、透湿度が低く、光線透過率に優れるビフェニル骨格、ビスフェノールA骨格又はナフタレン骨格である。更に好ましくは、ビフェニル骨格又はビスフェノールA骨格であり、最も好ましくはビスフェノールA骨格である。これらの化合物の粘度は1500mPa・s以下が好ましい。
本発明の成分(B)の含有量は、反応性化合物である成分(A)+成分(B)の総量100質量部に対して、20~80質量部であり、好ましくは30~70質量部である。低透湿度を達成する為に好ましい成分(B)の官能基当量は、10~1000g/eqであり、より好ましく、50~500g/eqである。
また、低透湿性の点から成分(A)と成分(B)は異なる化合物を使用する。これは、透湿度を低下させるのには電子密度の高い化合物が有効だと考えられるが、電子密度だけではなく化合物間の架橋密度とのバランスも重要だからである。その為、透湿度を低下させる為には、例えば成分(A)として、フェニル骨格、ビフェニル骨格、又はビスフェノールA骨格を含有し、重合性基(オキセタニル基又はエポキシ基)を一つ有する化合物を使用し、成分(B)として、フェニル骨格、ビフェニル骨格、ビスフェノールA骨格、又はナフタレン骨格を含有し重合性基(オキセタニル基又はエポキシ基)を複数(二つ乃至三つ以上)有する化合物を、それぞれ前記した好ましい含有量で使用する態様である。より好ましい組み合わせの一例としては、成分(A)として、ビフェニル骨格、又はビスフェノールA骨格を有し、かつ、オキセタニル基又はエポキシ基を一つ有する化合物(好ましくはエポキシ基を一つ有する化合物)を使用し、成分(B)として、フェニル骨格、ビフェニル骨格、又はビスフェノールA骨格を有し、かつ、オキセタニル基又はエポキシ基(好ましくはエポキシ基)を複数(少なくとも2つ)有する化合物又はシクロヘキサン骨格含有エポキシ化合物(例えばリモネンオキサイド、3,4-エポキシシクロヘキセニルメチル-3’,4’-エポキシシクロヘキセンカルボキシレート及び水添ビスフェノールジグリシジルエーテル化合物等)を使用する態様を挙げることができる。なお、水添ビスフェノールジグリシジルエーテル化合物としては、水添ビスフェノールA、F又はSジグリシジルエーテルが挙げられる。これらの成分(A)及び成分(B)として使用される化合物は何れも粘度が1300mPa・s以下が好ましく、より好ましくは800mPa・s以下、更に好ましくは500mPa・s以下である。
本発明においては脂肪族環を有する環状化合物(B)として、橋架け構造を有する脂環式炭化水素骨格、又はシクロアルキレン骨格と、及び、オキセタニル基またはエポキシ基とを有する環状化合物、又は、脂環式エポキシ樹脂を使用する。
上記における橋架け構造を有する脂環式炭化水素骨格又はシクロアルキレン骨格(橋架け構造を有しないシクロアルキレン骨格)は置換基を有していても、有していなくてもよい。置換基を有している場合の置換基はアルキル基、アルケニル基またはアルコキシ基を挙げることができ、これらの基は、炭素数1~4が好ましく、炭素数1~3が更に好ましい。
上記の脂肪族環を有する環状化合物(B)における脂肪族環骨格としては、橋架け構造を有する脂環式炭化水素骨格(好ましくは炭素数7~10の橋架け構造を有する脂環式炭化水素骨格)及び橋架け構造を含まないシクロアルキレン骨格(好ましくは炭素数4~7のシクロアルキレン骨格、より好ましくは炭素数5又は6のシクロアルキレン骨格、更に好ましくはシクロヘキシル骨格)を挙げることができる。なお、シクロアルキレン骨格の中で、シクロヘキシレン骨格は直接結合又は連結基を介して2つのシクロヘキシレン骨格が結合して、下記式(B-A)
(上記式中、Yは直接結合、硫黄原子またはメチレン基を、R3は水素原子または炭素数1~4のアルキル基を表し、tは1~4の整数を示す。)
で表される骨格であっても良い。
該環状化合物(B)における脂肪族環骨格としては、場合により、橋架け構造を有しない炭素数4~7のシクロアルキレン骨格が好ましく、より好ましくは炭素数5又は6のシクロアルキレン骨格であり、最も好ましくは2価のシクロヘキシレン骨格である。なお、シクロヘキシレン骨格は、上記の式(B-A)で表される骨格を形成していてもよい。
該環状化合物(B)における好ましい脂肪族環骨格を例示すると下記B-3に記載の群、
B-3:イソボルニル、アダマンタン、シクロペンタン、シクロヘキサン、水添ビスフェノールA、水添ビスフェノールF及び水添ビスフェノールS、
から選択される骨格を挙げることができ、更に、好ましくは、シクロペンタン、シクロヘキサン、水添ビスフェノールA、水添ビスフェノールF及び水添ビスフェノールSを挙げることが出来る。
架橋構造を含まないシクロアルキレン骨格の中では、シクロヘキシレン骨格が最も好ましい。シクロヘキヘキシレン骨格場合、式(B-A)で表される骨格を形成していないシクロヘキサン骨格が好ましい場合や式(B-A)で表される骨格を形成した方が好ましい場合があるので、適宜選択して使用することができる。
上記の環状化合物(B)を、前記の芳香族化合物(A)と組み合わせることで、極めて優れた耐湿性の効果を得ることができる。上記の骨格が水分に対して十分なバリアとなり、透湿を防ぐためである。
上記式(B-A)骨格において好ましいものは、Yが直接結合ないしメチレン基を有するものであり、直接結合のものが特に好ましい。
また、橋架け構造を有する脂環式炭化水素骨格として具体的には、アダマンタン骨格、ジシクロペンタジエン骨格、イソボルニル骨格が好適なものとして挙げられ、場合により、アダマンタン骨格又はイソボルニル骨格が好ましい。
また、シクロアルキレン骨格(橋架け構造を有しないシクロアルキレン骨格)の具体例としては、シクロペンタン骨格、シクロヘキサン骨格、シクロヘプタン骨格等が好適なものとして挙げられ、上記した様に、これらの2つが直接結合又は連結基を介して結合して上記式(B-A)骨格を形成していてもよい。
そして、具体的な連結としては、オキセタニル基またはエポキシ基が炭化水素基に結合し、該炭化水素基が、直接又はエーテル結合を介して、脂肪族環に連結される。炭化水素基によって連結されている場合の炭化水素基としては、炭素数1~10のアルキル基、又は、エーテル結合を有する炭素数1~10のアルキル基が挙げられる。好ましい連結基としての、エーテル結合を含む炭化水素基としては、炭素数1~4のアルキレン-酸素原子-炭素数1~4のアルキレン基(より好ましくは炭素数1~3のアルキキレン-酸素原子-炭素数1~3のアルキレン基)等のエーテル結合を炭素原子間に含む炭素数2~10のアルキレン基(より好ましくは2~6のアルキレン基)、又は、-オキシメチル基などのエーテル結合をアルキレン基の末端に有する炭素数1-4のアルキレン基(-オキシ-炭素数1-4のアルキル基)(より好ましくは-オキシ-炭素数1-3のアルキル基)等を挙げることができる。該アルキレン基がエーテル結合を末端に有する場合、通常、エーテル基が脂肪族環に結合し、アルキル基がオキセタン環またはエポキシ環に結合する。また、脂環式エポキシ樹脂のように脂肪族環にエポキシ基が直接形成されていてもよい。
本発明の脂肪族環を有する環状化合物(B)の含有量は反応性化合物である成分(A)+成分(B)の総量100質量部に対して、20~80質量部であり、好ましくは30~70質量部である。低透湿度を達成する為に、該環状化合物(B)の好ましい官能基当量は10~1000g/eqであり、より好ましくは50~500g/eqである。
上記ヘテロ環骨格と、オキセタニル基またはエポキシ基は、直接結合していても、また、2価の炭化水素基によって連結されていてもよいが、通常は、2価の炭化水素基によって連結されている。炭化水素基によって連結されている場合の炭化水素基としては、炭素数1~10のアルキレン基または、エーテル結合を有する炭素数1~10のアルキレン基が挙げられる。
ヘテロ環を有する成分(B)の含有量は反応性化合物である成分(A)+成分(B)の総量100質量部に対して、20~80質量部であり、好ましくは30~70質量部である。透湿度を向上させる為に好ましい該成分(B)の官能基当量は10~500g/eqであり、より好ましくは50~250g/eqである。
好ましい組み合わせとしては、上記成分(A)または上記成分(B)のいずれかが重量平均分子量2000以下、より好ましくは1000以下、特に好ましくは500以下のものを使用して硬化性樹脂組成物とすることが好ましい。このような低分子量のものを成分(A)、成分(B)のいずれか一方に使用することで、低吸湿性を確保しつつ、低粘度で塗布後に広がりやすく、OLEDの製造に優れた組成物を得ることができるためである。
また、特に熱硬化の場合、成分(A)と成分(B)のいずれか一方をオキセタン化合物とすることも好ましい。いずれか一方をオキセタン化合物とすることで、低吸湿性を確保しつつ、短時間での硬化性に優れた樹脂組成物を得ることができるためである。
さらに、成分(A)と成分(B)の好適な使用比率としては、(A)/(B)が8/2~2/8であり、7/3~3/7がより好ましい。
Tg(ガラス転移点)を向上させたい場合、芳香族系化合物であればビスフェノールA骨格、脂環式化合物であればジシクロペンタジエン骨格、イソボルニル骨格、アダマンタン骨格を導入すると良い。
特に、本発明では、樹脂組成物の粘度(25℃で測定した時の粘度:以下同じ)が通常1500mPa・s以下、好ましくは1300mPa・s以下、更に好ましくは、1200mPa・s以下であるので、成分(A)及び成分(B)を混合した時に、上記粘度以下になるようにするのが好ましい。
また、場合により、環状化合物(B)として、フルオレンやカルバゾール等の縮合環構造を有するオキセタン化合物またはエポキシ化合物も使用できる。
また、成分(A)及び成分(B)以外のフルオレンやカルバゾール等の縮合環構造を有するオキセタン化合物またはエポキシ化合物も、必要に応じて使用することができ、塗膜に剛性を付与することができる。これらオキセタン化合物またはエポキシ化合物は単独で用いてもよく、2種以上を用いてもよい。
さらに、環境及び人体への有害性、ならびに各国の規制を鑑みると、アンチモン元素を含有しない(トリクミル)ヨードニウムテトラキス(ペンタフルオロフェニル)ボレート、ジフェニル[4-(フェニルチオ)フェニル]スルホニウムトリフルオロトリスペンタフルオロエチルホスファート、トリス[4-(4-アセチルフェニルスルファニル)フェニル]スルホニウムトリス[(トリフルオロメチル)スルホニル]メタニドを使用することが最も好ましい。
本発明の光カチオン重合開始剤の含有量は成分(A)+成分(B)の総量100質量部に対して、0.05~5質量部であり、好ましくは0.1~3質量部である。なお、本発明の樹脂組成物においては、光カチオン重合開始剤は単独で用いてもよいし、複数種を混合して用いてもよい。
また、シクロヘキサン-1,3,4-トリカルボン酸-3,4-無水物を使用する場合、単独の使用では、固形または粘度が高い半固形状態のため作業性が極端に悪くなる場合がある。そのため、他の硬化剤、好ましくは脂環式骨格を有する酸無水物と併用して使用することが望ましい。この場合に併用することができる硬化剤としては液状で、粘度が低い物であれば特に限定されるものではないが、例えば市販されている硬化剤としては、無水メチルナジック酸、無水ナジック酸を含有したHNA-100(新日本理化(株)製)や、ヘキサヒドロ無水フタル酸、メチルヘキサヒドロ無水フタル酸を含有したリカシッドMH700(新日本理化(株)製)などの硬化剤が挙げられる。併用して使用する際には、あらかじめ固体または半固形状のシクロヘキサン-1,3,4-トリカルボン酸-3,4-無水物と粘度の低い硬化剤を室温または加温(加温条件としては、硬化剤の揮発を防ぐために好ましくは150℃以下、より好ましくは120℃である)条件下で均一になるまで混合することで作業性のよい状態にすることが可能である。また、取り扱い作業性と硬化後における封止材の凹みの観点から、シクロヘキサン-1,3,4-トリカルボン酸-3,4-無水物の全硬化剤中における使用比率としては、20~90質量%、より好ましくは、30~80質量%以下の範囲である。混合割合が90重量%を超えると、極端に硬化剤としての作業性に劣る。また20質量%を下回ると封止材の凹みの点で改善効果が薄くなるおそれがある。
該微粒子としては、有機微粒子、無機微粒子が挙げられる。また、微粒子は、必要とされる光線透過率、硬度、耐擦傷性、硬化収縮率、屈折率を考慮し単独、または複数種を混合して用いることができる。
通常、成分(A)+成分(B)を100質量部とした場合に、成分(A)の含有量は、20~80質量部であり、好ましくは30~70質量部である。成分(B)の含有量は20~80質量部であり、好ましくは30~70質量部である。成分(C)の含有量は熱カチオン開始剤であれば0.05~5質量部であり、好ましくは0.1~3質量部である。
本発明の樹脂組成物の総量に対して、通常、成分(A)+成分(B)の合計量は、50~99質量%程度が好ましく、より好ましくは70~99質量%であり、更に、好ましくは、80~99質量%であり、場合により、90~99質量%、更には、95~99質量%であっても良い。残部は上記の成分(C)及び任意の添加成分である。
該粘度は、好ましくは、E型粘度計(TV-200:東機産業社製)を用いて測定した粘度が25℃で1.5Pa・s(1500mPa・s)以下であり、より好ましくは1300mPa・s以下であり、更に好ましくは700mPa・s以下であり、特に好ましくは400mPa・s以下である。下限は特に無いが、通常、50mPa・s程度である。
また、本発明の樹脂組成物は、硬化時の収縮率(硬化収縮率)が、小さい方が好ましく、好ましくは5%以下であり、より好ましくは4%以下であり、更に好ましくは3.5%以下である。
また、本発明の樹脂組成物の硬化物は、有機発光層を外部の湿気などから保護するため、水蒸気透過度が50g/m2・24h(60℃で、湿度90%で測定、以下同じ)以下、好ましくは35g/m2・24h以下、より好ましくは30g/m2・24h以下、更に好ましくは30g/m2・24h未満が好ましい。
また、硬化物のガラス転位温度はある程度高い方が好ましく、本発明においては、該Tgが40℃以上が好ましく、より好ましくは45℃以上であり、最も好ましくは50℃以上である。
i.芳香族化合物(A)が、前記式(A-A)で表される骨格、前記式(A-B)で表される骨格、アントラセン骨格及びフェナントレン骨格からなる群から選択される少なくとも一つの骨格と、更に、オキセタニル基またはエポキシ基とを有する芳香族化合物(A)であり、
環状化合物(B)が、下記B-2に記載の群又は下記のB-3に記載の群
B-2:フェニル、ビフェニル、ナフタレン、ビナフタレン、アントラセン、フェナントレン、ビスフェノールA、ビスフェノールF及びビスフェノールS
B-3:イソボルニル、アダマンタン、シクロペンタン、シクロヘキサン、水添ビスフェノールA、水添ビスフェノールF及び水添ビスフェノールS、
から選択される少なくとも一つの骨格と、更に、オキセタニル基またはエポキシ基とを有する環状化合物、又は、脂環式エポキシ樹脂であり、
上記芳香族化合物(A)、環状化合物(B)(但し、B-2に記載の群から選ばれる骨格の場合、芳香族化合物(A)として使用される化合物は異なる化合物である)及び硬化剤(C)を含む有機EL素子の面封止用の樹脂組成物。
ii.芳香族化合物(A)及び環状化合物(B)の何れか一方が、少なくともオキセタニル基またはエポキシ基を一つ有する化合物を含む上記iに記載の樹脂組成物。
iii.芳香族化合物(A)が、芳香族骨格として、フェニル、ビフェニル及びビスフェノールAからなる群から選択される骨格を有する芳香族化合物(A)である上記i又はiiに記載の樹脂組成物。
iv.芳香族化合物(A)が、オキセタニル基またはエポキシ基を一つ有する芳香族化合物(A)を含む上記i~iiiの何れか一項に記載の樹脂組成物。
v.芳香族化合物(A)が、エポキシ基を一つ有する芳香族化合物(A)を含む上記i~ivの何れか一項に記載の樹脂組成物。
vii.環状化合物(B)が、
(a)フェニル、ビフェニル、ナフタレン、ビナフタレン及びビスフェノールAからなる群から選ばれる骨格、又は、
(b)下記(B-3)、に記載の群から選択される骨格
B-3:イソボルニル、アダマンタン、シクロペンタン、シクロヘキサン、水添ビスフェノールA、水添ビスフェノールF及び水添ビスフェノールS、
を有する環状化合物(B)である上記i~viの何れか一項に記載の樹脂組成物。
viii.環状化合物(B)が、フェニル、ビフェニル、ビスフェノールA、シクロペンタン、シクロヘキサン及び水添ビスフェノールAからなる群から選択される骨格を有する環状化合物(B)である上記i~viiの何れか一項に記載の樹脂組成物。
ix.環状化合物(B)が、ビフェニル、ビスフェノールA及びシクロヘキサンからなる群から選択される骨格を有する環状化合物(B)である上記viiiに記載の樹脂組成物。
x.環状化合物(B)が、少なくともオキセタニル基またはエポキシ基を少なくとも2つ有する環状化合物(B)又はリモネンオキサイドである上記i~ixの何れか一項に記載の樹脂組成物。
xi.環状化合物(B)の粘度が1500mPa・s以下である上記i~xの何れか一項に記載の樹脂組成物。
xii.環状化合物(B)として、粘度1500mPa・s以下であるビスフェノールAジグリシジルエーテルを含む上記xiに記載の樹脂組成物。
xiii.環状化合物(B)として、脂環式エポキシ樹脂を含む上記i~xiiの何れか一項に記載の樹脂組成物。
xv.上記樹脂組成物の粘度が好ましくは1300mPa・s以下である上記xivに記載の樹脂組成物。
xvi.厚さ100μmの硬化物とし、60℃で、相対湿度90%において測定した該硬化物の水蒸気透過度が35g/m2・24hr以下である上記i~xvの何れか一項に記載の樹脂組成物。
xvii.上記の硬化物の水蒸気透過度が30g/m2・24hr以下である上記xviに記載の樹脂組成物。
xviii.硬化収縮率が4%以下である上記i~xviiの何れか一項に記載の樹脂組成物。
xix.樹脂組成物の液屈折率が1.54~1.7である上記i~xviiの何れか一項に記載の樹脂組成物。
xx.樹脂組成物の硬化物のガラス転位点(Tg)が、45℃以上である上記i~xixの何れか一項に記載の樹脂組成物。
xxi.上記のガラス転移点が50℃以上である上記xxに記載の樹脂組成物。
xxii.芳香族化合物(A):環状化合物(B)の比率が3:7~7:3である上記i~xxiの何れか一項に記載の樹脂組成物。
xxiii.芳香族化合物(A):環状化合物(B)の比率が3.5:6.5~6.5:3.5である上記i~xxiの何れか一項に記載の樹脂組成物。
xxiv.硬化剤(C)が光カチオン重合開始剤である上記i~xxiの何れか一項に記載の樹脂組成物。
xxv.光カチオン重合開始剤が(トリクミル)ヨードニウムテトラキス(ペンタフルオロフェニル)ボレート、ジフェニル[4-(フェニルチオ)フェニル]スルホニウムトリフルオロトリスペンタフルオロエチルホスファート及びトリス[4-(4-アセチルフェニルスルファニル)フェニル]スルホニウムトリス[(トリフルオロメチル)スルホニル]メタニドからなる群から選択される化合物である上記xxivに記載の樹脂組成物。
xxvi.芳香族化合物(A)がo-フェニルフェノールグリシジルエーテルであり、環状化合物(B)が、粘度1500mPa・s以下であるビスフェノールAジグリシジルエーテル、キシリレンビスオキセタン、3,3’,5,5’-テトラメチル-4,4’-ビス(グリシジルオキシ)-1,1’-ビフェニル、ビフェニルアラルキル型ポリグリシジルエーテル、3,4-エポキシシクロヘキセニルメチル-3’,4’-エポキシシクロヘキセンカルボキシレート、水添ビスフェノールAジグリシジルエーテル及びリモネンオキサイドからなる群から選択される化合物である上記i乃至xxvの何れか一項に記載の樹脂組成物。
xxvii.環状化合物(B)が、粘度1500mPa・s以下であるビスフェノールAジグリシジルエーテル、3,4-エポキシシクロヘキセニルメチル-3’,4’-エポキシシクロヘキセンカルボキシレート及び水添ビスフェノールAジグリシジルエーテルからなる群から選択される化合物である上記xxviに記載の樹脂組成物。
xxviii.環状化合物(B)における脂環式エポキシ樹脂の脂肪族環が、炭素数6又は7、より好ましくはシクロヘキサン環である上記i乃至xxvの何れか一項に記載の樹脂組成物。
(1)下部電極/発光層/上部電極
(2)下部電極/電子輸送層/発光層/上部電極
(3)下部電極/発光層/正孔輸送層/上部電極
(4)下部電極/電子輸送層/発光層/正孔輸送層/上部電極
例えば、上記(4)の層構造を有する有機EL素子は、基板の片面上に、Al-Li合金等からなる下部電極(陰極)を抵抗加熱蒸着法またはスパッタ法によって形成し、次いで有機EL層として、オキサジアゾール誘導体やトリアゾール誘導体等からなる電子輸送層、発光層、TPD(N,N’-diphenyl-N,N’-bis(3-
methylphenyl)-1,1-biphenyl-. 4,4’-diamine)等からなる正孔輸送層及び上部電極(陽極)を抵抗加熱蒸着法又はイオンビームスパッタ法等の薄膜形成方法によって順次積層することによって作製することが可能である。なお、有機EL素子の層構造、又は材料は表示素子として機能するものであれば特に限定されるものではない。また、本発明による固体封止方法はいかなる構造の有機EL素子であっても適用可能である。
これを、JIS K7112 B法に準拠し、硬化物の比重(DS)を測定した。また、23±2℃で樹脂組成物の比重(DL)を測定し、次式により硬化収縮率を算出した。測定結果は4回の測定結果の平均値で示す。
硬化収縮率(%)=(DS-DL)/DS×100
(6)加工性:
清浄なガラス基板上にKAYATORON Z-5536を5μm厚みでディスペンサー(SHOTMASTER:武蔵エンジニアリング株式会社製)を使用し、シールパターンの塗布を行った。
次いで、実施例及び比較例の樹脂組成物をシールパターンと同様にディスペンサーを使用し微小滴をシールパターン枠内に滴下した。
更にもう一枚清浄なガラス基板を貼り合せ装置を用いて真空中で前記樹脂組成物滴下済み基板と貼り合せた。その後、大気開放してギャップ形成しUV照射(積算光量:3000mJ/cm2)し硬化させ、120℃オーブンに投入して1時間加熱硬化させ評価用試料を作製した。
評価基準
・・・滴下液が速やかにセル内に広がり、セル内に樹脂組成物が隙間無く均一に満たされている。
△・・・滴下液のセル内への広がりがやや遅いが、セル内に樹脂組成物が隙間無く均一に満たされている。
×・・・滴下液がセル内に充分に広がらず、セル内に隙間が生じ、樹脂組成物が均一に満たされていない。
OXT-121:東亞合成株式会社製キシリレンビスオキセタン
jER-828:三菱化学株式会社製ビスフェノールAジグリシジルエーテル
EP-4088S:株式会社ADEKA製ジシクロペンタジエンジメタノールジグリシジルエーテル
YX-4000H:三菱化学株式会社製3,3’,5,5’-テトラメチル-4,4’-ビス(グリシジルオキシ)-1,1’-ビフェニル
KAYARAD NC-3000H:日本化薬株式会社製ビフェニルアラルキル型ポリグリシジルエーテル
SEJ-01R:日本化薬株式会社製3,4-エポキシシクロヘキセニルメチル-3’,4’-エポキシシクロヘキセンカルボキシレート
GSID 26-1:BASFジャパン株式会社製(トリス[4-(4-アセチルフェニルスルファニル)フェニル]スルホニウムトリス[(トリフルオロメチル)スルホニル]メタニド
エポライト4000:共栄社化学株式会社製水添ビスフェノールAジグリシジルエーテル
リモネンオキサイド:RENESSENZ社製リモネンオキサイド
エポライト80MF:共栄社化学株式会社製グリセリンジグリシジルエーテル
エポライト100MF:共栄社化学株式会社製トリメチロールプロパントリグリシジルエーテル:
Claims (25)
- 下記(i)の式(A-A)で表される骨格、下記(ii)の式(A-B)で表される骨格、アントラセン骨格及びフェナントレン骨格からなる群から選択される少なくとも一つの骨格と、更に、オキセタニル基またはエポキシ基とを有する芳香族化合物(A)、及び、オキセタニル基またはエポキシ基を有し、下記(iii)の条件を満たす環状化合物(B)を含有し、且つ、25℃で測定した粘度が1300mPa・s以下である有機EL素子の面封止用の樹脂組成物、
(i) 式(A-A)
(上記式中、Xは直接結合、硫黄原子またはジメチルメチレン基を、R1は水素原子または炭素数1~4のアルキル基を表し、mは1~4の整数を示す。)、
で表される骨格、
(ii) 式(A-B)
(上記式中、R2は水素原子または炭素数1~4のアルキル基を表し、nは1~4の整数を示す)
で表される骨格、
(iii)該環状化合物(B)の条件:
該環状化合物(B)における環は、芳香族環、脂肪族環またはヘテロ環であり、これらの中で環が、(a)芳香族環の場合、該環状化合物は、前記芳香族化合物(A)として使用される化合物とは異なる構造を有する化合物であり、また、(b)脂肪族環の場合、該環状化合物は、橋架け構造を有する脂環式炭化水素骨格又はシクロアルキレン骨格と、及び、オキセタニル基またはエポキシ基とを有する環状化合物、又は、脂環式エポキシ樹脂である。 - 芳香族化合物(A)が下記(A-1)
A-1:フェニル、ビフェニル、アントラセン、フェナントレン、ビスフェノールA、ビスフェノールF及びビスフェノールS、
に記載の群から選択される骨格を有する請求項1に記載の樹脂組成物。 - 芳香族化合物(A)が、芳香族骨格として、フェニル、ビフェニル及びビスフェノールAからなる群から選択される骨格を有する化合物である請求項1または請求項2に記載の樹脂組成物。
- 環状化合物(B)が下記(B-1)、
B-1:芳香族環、上記脂肪族環及びヘテロ環、
に記載の群から選択される環を有する請求項1乃至請求項3の何れか一項に記載の樹脂組成物。 - 環状化合物(B)が脂環式エポキシ樹脂である請求項1に記載の樹脂組成物。
- 環状化合物(B)の環が芳香族環である請求項1乃至請求項4の何れか1項に記載の樹脂組成物。
- 環状化合物(B)が下記(B-2)
B-2:フェニル、ビフェニル、ナフタレン、ビナフタレン、アントラセン、フェナントレン、ビスフェノールA、ビスフェノールF及びビスフェノールS、
に記載の群から選択される骨格を有する請求項7に記載の樹脂組成物、 - 環状化合物(B)がフェニル、ビフェニル、ナフタレン、ビナフタレン及びビスフェノールAからなる群から選ばれる骨格を有するオキセタン化合物またはエポキシ化合物である請求項8に記載の樹脂組成物。
- 環状化合物(B)が下記(B-3)、
B-3:イソボルニル、アダマンタン、シクロペンタン、シクロヘキサン、水添ビスフェノールA、水添ビスフェノールF及び水添ビスフェノールS、
に記載の群から選択される骨格を有する請求項1乃至請求項4の何れか1項に記載の樹脂組成物。 - 環状化合物(B)がアダマンタン、シクロヘキサン及び水添ビスフェノールAからなる群から選ばれる骨格を有するオキセタン化合物またはエポキシ化合物である請求項4または請求項10に記載の樹脂組成物。
- 環状化合物(B)が下記(B-4)、
B-4:モルホリン、テトラヒドロフラン、オキサン、ジオキサン、トリアジン、カルバゾール、ピロリジン及びピペリジン、
に記載の群から選択される骨格を有する請求項1乃至請求項4に記載の樹脂組成物。 - 環状化合物(B)がオキサン、ジオキサン及びトリアジンからなる群から選ばれる骨格を有するオキセタン化合物またはエポキシ化合物である請求項4または請求項12に記載の樹脂組成物。
- さらに硬化剤(C)を含有する請求項1乃至請求項13の何れか一項に記載の樹脂組成物。
- 硬化剤(C)が光カチオン重合開始剤である請求項14に記載の樹脂組成物。
- 前記光カチオン重合開始剤が下記(C-1)、
C-1:スルホニウム塩、ヨードニウム塩、ホスホニウム塩、アンモニウム塩、及びアンチモン酸塩、
に記載の群から選択される少なくとも一つである請求項15に記載の樹脂組成物。 - 硬化剤(C)が熱硬化剤である請求項14に記載の樹脂組成物。
- 前記熱硬化剤が下記(C-2)、
C-2:アミン系化合物、酸無水物系化合物、アミド系化合物、フェノール系化合物、カルボン酸系化合物、イミダゾール系化合物、イソシアヌル酸付加物、金属化合物、スルホニウム塩、アンモニウム塩、アンチモン酸塩、ホスホニウム塩、マイクロカプセル型硬化剤、
に記載の群から選択される請求項17に記載の樹脂組成物。 - 芳香族化合物(A)と環状化合物(B)の総量100質量部に対して、芳香族化合物(A)を20~80質量部含有する請求項1乃至請求項18の何れか1項に記載の樹脂組成物。
- 芳香族化合物(A)と環状化合物(B)の総量を100質量部に対して、環状化合物(B)を20~80質量部含有する請求項1乃至請求項19の何れか1項に記載の樹脂組成物。
- 芳香族化合物(A)と環状化合物(B)の総量を100質量部とした場合に硬化剤(C)を0.1~5質量部含有する請求項1乃至請求項20の何れか1項に記載の樹脂組成物。
- 厚さ100μmの硬化物とし、60℃で、相対湿度90%において測定した該硬化物の水蒸気透過度が35g/m2・24hr以下である請求項1乃至請求項21の何れか一項に記載の樹脂組成物。
- 請求項1乃至請求項22の何れか一項に記載の樹脂組成物を硬化せしめて得られる硬化物で面封止された有機ELディスプレイ。
- 請求項1乃至請求項22の何れか一項に記載の樹脂組成物を基材上に塗布、硬化させてなるバリア性能を有する有機ELディスプレイの面封止用のフィルム。
- 請求項1乃至請求項22の何れか一項に記載の樹脂組成物の有機EL素子の面封止のための使用。
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JP6363508B2 (ja) | 2018-07-25 |
CN104813741A (zh) | 2015-07-29 |
JPWO2014083850A1 (ja) | 2017-01-05 |
TW201428025A (zh) | 2014-07-16 |
KR20150090063A (ko) | 2015-08-05 |
TWI658062B (zh) | 2019-05-01 |
CN104813741B (zh) | 2018-01-05 |
KR101999614B1 (ko) | 2019-07-12 |
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