WO2013118509A1 - 有機el素子用の面封止剤、これを用いた有機elデバイス、及びその製造方法 - Google Patents
有機el素子用の面封止剤、これを用いた有機elデバイス、及びその製造方法 Download PDFInfo
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- WO2013118509A1 WO2013118509A1 PCT/JP2013/000685 JP2013000685W WO2013118509A1 WO 2013118509 A1 WO2013118509 A1 WO 2013118509A1 JP 2013000685 W JP2013000685 W JP 2013000685W WO 2013118509 A1 WO2013118509 A1 WO 2013118509A1
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- Prior art keywords
- group
- organic
- carbon atoms
- sealing agent
- general formula
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- 238000007789 sealing Methods 0.000 title claims abstract description 151
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 116
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- 239000003822 epoxy resin Substances 0.000 claims abstract description 87
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 30
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 239000000758 substrate Substances 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 239000000565 sealant Substances 0.000 claims description 44
- 238000001723 curing Methods 0.000 claims description 42
- 238000002161 passivation Methods 0.000 claims description 30
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000000524 functional group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 238000013007 heat curing Methods 0.000 claims description 6
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 3
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
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- 230000000694 effects Effects 0.000 description 14
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- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- 150000001412 amines Chemical class 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- YIMHRDBSVCPJOV-UHFFFAOYSA-N n'-(2-ethoxyphenyl)-n-(2-ethylphenyl)oxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C(=O)NC1=CC=CC=C1CC YIMHRDBSVCPJOV-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- LKTCWOYIQVKYIV-UHFFFAOYSA-N n-butyl-4-chloro-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)-1,3,5-triazin-2-amine Chemical compound N=1C=NC(Cl)=NC=1N(CCCC)C1CC(C)(C)N(C)C(C)(C)C1 LKTCWOYIQVKYIV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 150000002978 peroxides Chemical class 0.000 description 1
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- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
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- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
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- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-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
- JBYYGVMOBTYNOM-UHFFFAOYSA-N trimethoxy-[3-(4-methylpiperazin-1-yl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCN1CCN(C)CC1 JBYYGVMOBTYNOM-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/842—Containers
- H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- C08G59/40—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 curing agents 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
- 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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
-
- 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
-
- 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
-
- 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
- H10K59/873—Encapsulations
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/16—Applications used for films
- C08L2203/162—Applications used for films sealable films
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
Definitions
- the present invention relates to a surface sealant for an organic EL element, an organic EL device using the same, and a method for producing the same.
- the organic EL element is an organic semiconductor device, and is expected as a liquid crystal backlight or a self-luminous thin flat display device.
- organic EL elements are extremely susceptible to deterioration when exposed to moisture and oxygen. That is, the interface between the metal electrode and the organic EL layer is peeled off due to the influence of moisture, the metal is oxidized to increase resistance, or the organic matter itself is altered by moisture. Thereby, there exists a fault that an organic EL element stops light emission, or a brightness
- quaternary ammonium salts are known as, for example, catalysts for isocyanuration reactions, cationic surfactants, and the like (see, for example, Patent Documents 2 and 3).
- the organic EL element when used as a portable electronic device or a lighting device, it is exposed to sunlight for a long time, and therefore, weather resistance is required.
- the cured product of the surface sealant of the organic EL element changes color, the light extraction efficiency of the top emission type organic EL element decreases.
- the design of the organic EL element deteriorates.
- the back emission type organic EL element even in the back emission type organic EL element, there is a problem that the design property is deteriorated when the cured product of the surface sealing agent is discolored.
- the above-mentioned surface sealant of Patent Document 1 is excellent in low-temperature curability and has high transparency of the cured film.
- a composition that is easily cured at a low temperature has a problem that a curing reaction is likely to occur during storage or transportation, and storage stability is poor.
- the present invention has been made in view of the above problems, and provides a surface sealing agent that is curable at a low temperature but has excellent storage stability and weather resistance.
- a surface sealing agent for an organic EL device comprising 0.1 to 10 parts by weight of the curing accelerator (B) with respect to 100 parts by weight of a stopper.
- R 1 , R 2 and R 3 are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, and 6 to 6 carbon atoms which may have a substituent.
- 10 represents an aryl group having 7 to 20 carbon atoms which may have a substituent
- Ar represents an aryl group having 6 to 10 carbon atoms which may have a substituent.
- R 4 , R 5 and R 6 are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, and 6 to 6 carbon atoms which may have a substituent.
- R 10 represents an aryl group having 7 to 20 carbon atoms which may have a substituent
- Ra, Rb and Rc each independently represents a hydrogen group or an alkyl group having 1 to 10 carbon atoms, Represents an alkoxy group of 1 to 10, F, Cl, Br, I, NO 2 , CN, or a group represented by the following general formula (3).
- R 7 , R 8 and R 9 each independently represents a hydrogen group or a hydrocarbon group having 1 to 10 carbon atoms.
- the substituent bonded to Ar in the general formula (1) is an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, F, Cl, Br, I, NO 2 , CN
- the surface sealing agent according to [1] which is a functional group selected from the group consisting of groups represented by the following general formula (4).
- R 10 , R 11 and R 12 each independently represents a hydrogen group or a hydrocarbon group having 1 to 10 carbon atoms.
- the substituent bonded to Ar in the general formula (1) is an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a group represented by the general formula (4).
- the substituents of R 1 , R 2 and R 3 in the general formula (1) and the substituents of R 4 , R 5 and R 6 in the general formula (2) each independently have a carbon number.
- R 13 , R 14 and R 15 each independently represents a hydrogen group or a hydrocarbon group having 1 to 10 carbon atoms.
- the counter anion of the salt (B1) or the salt (B2) is [CF 3 SO 3 ] ⁇ , [C 4 F 9 SO 3 ] ⁇ , [PF 6 ] ⁇ , [AsF 6 ] ⁇ , [ Ph 4 B] ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , [OC (O) R 16 ] ⁇ (R 16 represents an alkyl group having 1 to 10 carbon atoms), [SbF 6 ] ⁇ , [B (C 6 F 5 ) 4 ] ⁇ , [B (C 6 H 4 CF 3 ) 4 ] ⁇ , [(C 6 F 5 ) 2 BF 2 ] ⁇ , [C 6 F 5 BF 3 ] ⁇ , and [B (C 6 H 3 F 2) 4] - is selected from the group consisting of, Menfutomezai according to any one of [1] to [4].
- the surface sealing agent according to any one of [1] to [5
- the second of the present invention relates to the following organic EL device and method for producing the same.
- An organic EL panel comprising the organic EL device according to [8].
- the surface sealing agent of the present invention contains a curing accelerator made of an ammonium salt having a specific structure and can be sufficiently cured at a low temperature. Therefore, the organic EL element can be sealed without damaging it. Moreover, the hardened
- FIG. 1A and FIG. 1B are schematic cross-sectional views of a surface-sealing type organic EL device. It is a figure which shows an example of the manufacturing process of a surface sealing type organic EL device. It is a figure which shows the other example of the manufacturing process of a surface sealing type organic EL device.
- the surface sealing agent of the present invention includes an epoxy resin (A) and a curing accelerator (B) composed of a salt of a specific quaternary ammonium ion; A silane coupling agent (C) or the like may be included.
- the epoxy resin (A) contained in the surface sealing agent of this invention should just be an epoxy resin which has two or more epoxy groups in 1 molecule, and molecular weight etc. are not specifically limited. An epoxy resin having no molecular weight distribution or an epoxy resin having a molecular weight distribution can be used.
- epoxy resins having two epoxy groups in one molecule include hydroquinone diglycidyl ether, resorcin diglycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, cyclohexanediol diglycidyl ether, cyclohexanedimethanol diglycidyl ether, dicyclopentadienediol diglycidyl ether, 1,6-naphthalenediol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F di Examples include glycidyl ether, hydrogenated bisphenol A diglycidyl ether, and hydrogenated bisphenol F diglycidyl ether.
- Examples of the compound having 3 or more epoxy groups in one molecule include trimethylolpropane triglycidyl ether, pentaerythritol tetraglycidyl ether, phenol novolac type epoxy, cresol novolac type epoxy and the like.
- the epoxy resin may contain a polymer or oligomer having an epoxy group.
- the polymer or oligomer having an epoxy group is not particularly limited, and may be a polymer such as a vinyl monomer having an epoxy group.
- Examples of the vinyl monomer having an epoxy group include (meth) acrylate monomers such as glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, and methyl glycidyl (meth) acrylate.
- the epoxy resin (A) may be a copolymer or copolymer oligomer of a vinyl monomer having an epoxy group and another vinyl monomer.
- examples of other vinyl monomers include (meth) acrylates.
- the ester groups of (meth) acrylates are methyl, ethyl, isopropyl, normal butyl, isobutyl, tertiary butyl, 2-ethylhexyl, cyclohexyl, benzyl, isobornyl, lauryl, myristyl. And so on. That is, a non-functional alkyl ester is preferable regardless of a linear structure or a branched structure.
- the epoxy resin may be a copolymer of a vinyl monomer having an epoxy group and styrene, ⁇ -methylstyrene, vinyl acetate or the like.
- Preferred specific examples of the epoxy resin (A) contained in the surface sealing agent of the present invention include tetrafunctional naphthalene type epoxy resin (Aa), triphenylmethane type epoxy resin (Ab), and dicyclopentadiene type.
- R a1 each independently represents a hydrogen atom or a methyl group
- R a2 each independently represents a hydrogen atom or a methyl group
- R a3 each independently represents an alkyl group having 1 to 5 carbon atoms
- Each of R a4 independently represents an alkyl group having 1 to 5 carbon atoms
- n represents each independently an integer of 0 to 3
- m independently represents an integer of 1 to 3
- p represents each independently an integer of 0 to 4
- q represents each independently an integer of 0 to 4)
- the heat resistance of the cured products of these surface sealants is likely to be improved.
- the surface sealing agent containing these epoxy resins tends to improve translucency and adhesiveness.
- the viscosity of the surface sealant containing these epoxy resins can be easily adjusted to a desired range (for example, a viscosity measured at 25 ° C. and 1.0 rpm with an E-type viscometer is 200 to 10,000 mPa ⁇ s). Therefore, the surface sealing agent of the present invention is easy to form a film by screen printing or the like.
- the epoxy resin (A) may contain one or both of a high molecular weight phenol type epoxy resin (A-1) and a low molecular weight phenol type epoxy resin (A-2).
- the epoxy resin (A) contains a high molecular weight phenol type epoxy resin (A-1) or a low molecular weight phenol type epoxy resin (A-2)
- the surface sealant can be formed into a sheet. .
- the high molecular weight phenol type epoxy resin (A-1) is preferably a polymer or oligomer having a phenol resin and epichlorohydrin as monomer components, and more preferably an oligomer having these as monomer components.
- the monomer component of the high molecular weight phenol type epoxy resin (A-1) may contain only a phenol resin and epichlorohydrin, and a part of the monomer component includes compounds other than the phenol resin and epichlorohydrin. (Comonomer component) may be included.
- the weight average molecular weight (Mw) of the resulting high molecular weight phenol type epoxy resin (A-1) tends to fall within a desired range.
- the monomer component of the high molecular weight phenol type epoxy resin (A-1) is appropriately selected, the smoothness of the coating film surface of the surface sealing agent is increased.
- the weight average molecular weight (Mw) of the high molecular weight phenol type epoxy resin (A-1) is preferably 3 ⁇ 10 3 to 2 ⁇ 10 4 , more preferably 3 ⁇ 10 3 to 7 ⁇ 10 3 .
- the “weight average molecular weight (Mw)” is measured by gel permeation chromatography (GPC) using polystyrene as a standard substance.
- the weight average molecular weight (Mw) of the high molecular weight phenol type epoxy resin (A-1) is in the above numerical range, a cured film having high adhesion and low moisture permeability can be obtained.
- the surface sealing agent containing the high molecular weight phenol type epoxy resin (A-1) whose weight average molecular weight (Mw) is in the above numerical range is easy to apply and easily form a film.
- the epoxy equivalent of the high molecular weight phenol type epoxy resin (A-1) is preferably 500 to 10,000 g / eq.
- the low molecular weight phenol type epoxy resin (A-2) is a phenol type epoxy resin having a weight average molecular weight of preferably 200 to 800; more preferably a phenol type epoxy resin having a weight average molecular weight of 300 to 700. is there.
- the “weight average molecular weight (Mw)” is measured by gel permeation chromatography (GPC) using polystyrene as a standard substance.
- the low molecular weight phenol type epoxy resin (A-2) may be an oligomer having, for example, bisphenol and epichlorohydrin as monomer components.
- oligomeric phenol derivatives containing a phenol derivative and epichlorohydrin as monomer components include bisphenol, hydrogenated bisphenol, phenol novolac, cresol novolac, and the like.
- the repeating structural unit contained in the low molecular weight phenol type epoxy resin (A-2) may be the same as or different from the repeating structural unit contained in the high molecular weight bisphenol type epoxy resin (A-1).
- Examples of the low molecular weight bisphenol type epoxy resin (A-2) include a compound represented by the general formula (X), and preferred examples include a compound represented by the general formula (X ′). .
- X represents a single bond, a methylene group, an isopropylidene group, —S—, or —SO 2 —; each R 1 independently represents an alkyl group having 1 to 5 carbon atoms. P represents an integer of 0-4.
- the epoxy equivalent of the low molecular weight phenol type epoxy resin (A-2) is preferably 100 to 800 g / eq.
- the fluidity of the surface sealant is enhanced, and the adhesion of the surface sealant to the organic EL element is enhanced.
- the ratio of the high molecular weight phenolic epoxy resin (A-1) and the low molecular weight phenolic epoxy resin (A-2) contained in the sheet-like surface sealing agent is not particularly limited, and the desired viscosity is realized. It is preferable to adjust the composition so that it is possible. If the content of the high molecular weight phenol type epoxy resin (A-1) is too large, the moisture permeability of the cured film (seal member) becomes high. Moreover, the shape following property at the time of bonding to an organic EL element becomes low, and a gap is easily formed between the cured film and the organic EL element. On the other hand, when the content of the high molecular weight phenol type epoxy resin (A-1) is too small, the adhesive strength of the cured film is lowered.
- the epoxy resin (A) is preferably contained in the surface sealing agent in an amount of 70 to 99.9% by weight, more preferably 80 to 99.9% by weight, still more preferably 90 to 99.9% by weight.
- the epoxy resin (A) is included in the above range, the strength of the cured film of the surface sealing agent is increased, and the organic EL element can be protected from moisture, oxygen, and the like.
- the curing accelerator (B) contained in the surface sealing agent of the present invention comprises a salt (B1 or B2) containing a specific quaternary ammonium ion.
- the salt (B1) includes a quaternary ammonium ion represented by the following general formula (1).
- R 1 , R 2 and R 3 are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, and 6 to 10 carbon atoms which may have a substituent. Or an aryl group having 7 to 20 carbon atoms which may have a substituent.
- R 1 , R 2 , and R 3 are preferably each independently a methyl group, a phenyl group, or a benzyl group.
- the type of the substituent for R 1 , R 2 , and R 3 in the general formula (1) is not particularly limited, but an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, F, Cl, It is preferably a functional group selected from the group consisting of Br, I, NO 2 , CN, and a group represented by the following general formula (5).
- R 13 , R 14 , and R 15 are each independently a hydrogen group, or It represents a hydrocarbon group having 1 to 10 carbon atoms, and it is preferred that all of R 13 , R 14 and R 15 are hydrocarbon groups. When all of R 13 , R 14 and R 15 are hydrocarbon groups, the storage stability of the surface sealant is increased.
- the hydrocarbon group may be a linear, branched or cyclic aliphatic group, or may be aromatic.
- Ar represents an aryl group having 6 to 10 carbon atoms which may have a substituent.
- Ar is preferably an aromatic hydrocarbon group, and may be, for example, a phenyl group or a naphthyl group.
- the type of the substituent bonded to Ar in the general formula (1) is not particularly limited, but from the viewpoint of the stability of the compound, the alkyl group having 1 to 10 carbon atoms, the alkoxy group having 1 to 10 carbon atoms, It is preferably a functional group selected from the group consisting of F, Cl, Br, I, NO 2 , CN, and a group represented by the following general formula (4).
- R 10 , R 11 , and R 12 are each independently a hydrogen group or a carbon number of 1 to 10 Represents a hydrocarbon group. It is particularly preferable that all of R 10 , R 11 and R 12 are hydrocarbon groups. When all of R 10 , R 11 , and R 12 are hydrocarbon groups, the storage stability of the surface sealant is increased.
- the hydrocarbon group may be a linear, branched or cyclic aliphatic group, or may be aromatic.
- the bonding position of the substituent bonded to Ar in the general formula (1) and the number of substituents bonded to Ar are not particularly limited. It selects suitably according to the reactivity with respect to an epoxy resin (A), etc.
- the substituent bonded to Ar is an electron-attracting group; that is, when the substituent bonded to Ar is F, Cl, Br, I, NO 2 , or CN, the general formula (1
- the substituent is preferably bonded to the meta position or the para position with respect to the bonding position between Ar and the methylene group. When an electron withdrawing group is bonded to this position, the curing reaction of the epoxy resin (A) is easily promoted.
- the number of electron-withdrawing groups bonded to Ar is preferably 2 or less.
- the substituent bonded to Ar is an electron donating group; that is, when the substituent bonded to Ar is an alkyl group, an alkoxy group, or a group represented by the above general formula (5)
- the substituent is preferably bonded to the para position with respect to the bonding position between Ar and the methylene group in the general formula (1).
- an electron donating group is bonded to this position, the curing reaction of the epoxy resin (A) is easily promoted.
- the substituent bonded to Ar is an electron-withdrawing group, the curing reaction of the epoxy resin (A) is more easily promoted when the substituent is an electron-donating group.
- Preferred examples of the quaternary ammonium ion represented by the general formula (1) include the following ions.
- the salt (B1) includes a quaternary ammonium ion represented by the general formula (1) and a counter anion.
- counter anions include [CF 3 SO 3 ] ⁇ , [C 4 F 9 SO 3 ] ⁇ , [PF 6 ] ⁇ , [AsF 6 ] ⁇ , [Ph 4 B] ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , [OC (O) R 16 ] ⁇ (R 16 represents an alkyl group having 1 to 10 carbon atoms), [SbF 6 ] ⁇ , [B (C 6 F 5 ) 4 ] ⁇ , [B (C 6 H 4 CF 3 ) 4 ] ⁇ , [(C 6 F 5 ) 2 BF 2 ] ⁇ , [C 6 F 5 BF 3 ] ⁇ , or [B (C 6 H 3 F 2 ) 4 ] ⁇ .
- an anion having a small logarithm (pKa) of the reciprocal of the acid dissociation constant is preferable.
- the salt (B2) includes a quaternary ammonium ion represented by the following general formula (2).
- R 4 , R 5 and R 6 are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, and 6 to 6 carbon atoms which may have a substituent.
- 10 represents an aryl group having 7 to 20 carbon atoms which may have a substituent.
- a methyl group, a phenyl group, and a benzyl group are particularly preferable.
- the type of the substituent of R 4 , R 5 , R 6 in the general formula (2) is not particularly limited, and may be the same as the substituent of R 1 , R 2 , R 3 in the general formula (1). .
- Ra, Rb, and Rc are each independently a hydrogen group or an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, F, Cl, Br, I, NO 2 , CN, or a group represented by the following general formula (3).
- R 7 , R 8 , and R 9 are each independently a hydrogen group, or a carbon number of 1 to 10 Represents a hydrocarbon group. All of R 7 , R 8 and R 9 are preferably hydrocarbon groups. When all of R 7 , R 8 , and R 9 are hydrocarbon groups, the storage stability of the surface sealant is increased.
- the hydrocarbon group may be a linear, branched or cyclic aliphatic group, or may be aromatic.
- the salt (B2) includes a quaternary ammonium ion represented by the general formula (2) and a counter anion.
- the counter anion may be the same as the counter anion contained in the salt (B1).
- the content of the curing accelerator (B) is 0.1 to 10 parts by weight, preferably 0.1 to 5 parts by weight, more preferably 0.1 to 100 parts by weight of the surface sealing agent. ⁇ 3 parts by mass.
- the addition amount of the curing accelerator (B) is too small, the epoxy resin (A) cannot be cured sufficiently.
- the amount of the curing accelerator (B) is excessive, the amount of unreacted curing accelerator (B) increases. Thereby, the moisture permeability of the cured product of the surface sealing agent of the present invention may increase, which may cause deterioration of the organic EL element.
- a hardening accelerator (B) may be comprised only with 1 type of compound, and may be a combination of 2 or more types of compounds.
- the ratio of the amount of ammonium ions in the curing accelerator (B) to the amount of epoxy groups contained in the surface sealing agent is preferably 0.5 to 10%, more preferably 0.5 to 1%.
- the curing accelerator (B) quaternary ammonium ions contained in the salt (B1) or the salt (B2) react as shown in the following reaction mechanism examples; the curing accelerator (B) cures the epoxy resin. It is inferred to promote.
- the reaction mechanism of the quaternary ammonium ion contained in the salt (B1) will be described as an example, but it is presumed that the quaternary ammonium ion contained in the salt (B2) reacts similarly.
- the methylene group is adjacent to the aryl group having a ⁇ bond.
- the transfer reaction (intermediate (b) to (e)) tends to proceed at a certain temperature or higher.
- the proton at the benzyl position of the ammonium ion (a) is eliminated, and the intermediate ion (b) is easily transferred.
- the transfer reaction does not proceed easily at low temperatures, the surface sealant has a high storage stability.
- the aromatic compound derived from the curing accelerator is added to the end of the epoxy resin, and the epoxy resin is colored. is there.
- the functional group derived from the curing accelerator is added to the terminal of the epoxy resin, the main skeleton of the epoxy resin around the functional group is easily cut by the plasma irradiation. That is, the plasma resistance of the cured epoxy resin is reduced.
- the quaternary ammonium ion (a) is difficult to add to the end of the epoxy resin. Therefore, the epoxy resin is difficult to be colored, and the main skeleton of the epoxy resin is not easily cut even by plasma irradiation.
- the reactivity of the quaternary ammonium ion (a) can be adjusted by the substituent of the aryl group adjacent to the methylene group.
- the substituent of the aryl group is an electron donating group, the reaction easily proceeds from the intermediate (b) to the final product (e), and the reactivity of the quaternary ammonium ion (a) is increased.
- the surface sealing agent of the present invention may contain a coupling agent (C) such as a silane coupling agent, a titanium coupling agent, a zirconium coupling agent, and an aluminum coupling agent.
- the surface sealant containing the coupling agent (C) has high adhesion to the substrate of the organic EL device.
- silane coupling agent (C) examples include 1) a silane coupling agent having an epoxy group, 2) a silane coupling agent having a functional group capable of reacting with an epoxy group, and 3) other silane coupling agents. included.
- the silane coupling agent (C) is preferably a silane coupling agent that reacts with the epoxy resin (A) in the surface sealing agent. When the silane coupling agent (C) reacts with the epoxy resin (A), the low molecular weight component does not remain in the cured film.
- the silane coupling agent that reacts with the epoxy resin (A) is preferably 1) a silane coupling agent having an epoxy group, or 2) a silane coupling agent having a functional group capable of reacting with an epoxy group. Reacting with an epoxy group means an addition reaction with an epoxy group.
- a silane coupling agent having an epoxy group is a silane coupling agent having an epoxy group such as a glycidyl group; examples thereof include ⁇ -glycidoxypropyltrimethoxysilane, ⁇ - (3,4- Epoxycyclohexyl) ethyltrimethoxysilane and the like.
- Functional groups capable of reacting with epoxy groups include amino groups such as primary amino groups and secondary amino groups; carboxyl groups and the like, and groups that can be converted into functional groups capable of reacting with epoxy groups (for example, Methacryloyl group, isocyanate group, etc.).
- Examples of such a silane coupling agent having a functional group capable of reacting with an epoxy group include N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3- Aminopropylmethyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N- ( 1,3-dimethyl-butylidene) propylamine, N-phenyl-3-aminopropyltrimethoxysilane or 3- (4-methylpiperazino) propyltrimethoxysilane, trimethoxysilylbenzoic acid, ⁇ -methacryloxypropyltrimethoxysilane, And ⁇ -isocyanato
- silane coupling agents examples include vinyltriacetoxysilane and vinyltrimethoxysilane.
- One kind of these silane coupling agents may be contained in the surface sealing agent, or two or more kinds thereof may be contained.
- the molecular weight of the silane coupling agent (C) contained in the surface sealing agent is preferably 80 to 800. When the molecular weight of the silane coupling agent (C) exceeds 800, the adhesion may be lowered.
- the content of the silane coupling agent (C) in the surface sealing agent is preferably 0.05 to 30 parts by mass, and 0.1 to 20 parts by mass with respect to 100 parts by mass of the surface sealing agent. More preferred is 0.3 to 10 parts by mass.
- the surface sealant of the present invention may contain other optional component (D) as long as the effects of the present invention are not impaired.
- other optional component (D) include a resin component, a filler, a modifier, an antioxidant, a stabilizer, an acid anhydride, and the like.
- resin components include polyamide, polyamideimide, polyurethane, polybutadiene, polychloroprene, polyether, polyester, styrene-butadiene-styrene block copolymer, petroleum resin, xylene resin, ketone resin, cellulose resin, fluorine-based oligomer, Silicon-based oligomers, polysulfide-based oligomers and the like are included.
- the surface sealant may contain only one kind of these resin components or two or more kinds.
- filler examples include glass beads, styrene polymer particles, methacrylate polymer particles, ethylene polymer particles, propylene polymer particles, and the like.
- surface sealing agent only one kind of filler may be contained, or two or more kinds may be contained.
- modifiers include polymerization initiation aids, anti-aging agents, leveling agents, wettability improvers, surfactants, plasticizers, and the like.
- the surface sealing agent may contain only one of these modifiers, or two or more of them.
- stabilizers include ultraviolet absorbers, preservatives, antibacterial agents and the like.
- the surface sealing agent may contain only one kind of these stabilizers or two or more kinds.
- Antioxidants refer to those that deactivate radicals generated by plasma irradiation or sunlight irradiation (Hindered Amine Light Stabilizer, HALS) and those that decompose peroxides. When the surface sealant contains an antioxidant, discoloration of the cured product of the surface sealant is suppressed.
- hindered amines include bis (2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis (1,2,2,6,6-pentamethylpiperidin-4-yl) sebacate .
- phenolic antioxidants include monophenols such as 2,6-di-t-butyl-p-cresol and 2,6-di-t-butyl-4-ethylphenol, 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 2,2′-methylenebis (4-ethyl-6-tert-butylphenol), 4,4′-thiobis (3-methyl-6-tert-butylphenol), 4, Bisphenols such as 4′-butylidenebis (3-methyl-6-tert-butylphenol), 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, 1,3,5 -Polymeric phenols such as trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxybenzyl) benzene are included.
- monophenols such as 2,6-di-t-butyl-p-cresol and 2,6-di-t-butyl-4-ethy
- an antioxidant selected from phosphites and a colorant selected from oxaphosphaphenanthrene oxides are preferably used.
- the phosphites include trioctyl phosphite, dioctyl monodecyl phosphite, didecyl monooctyl phosphite and the like.
- oxaphosphaphenanthrene oxides include 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and the like.
- the antioxidant is Tinuvin 123 (bis (1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebacic acid) in terms of imparting resistance to ultraviolet rays to the cured product of the surface sealing agent.
- Tinuvin 765 (mixture of bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacic acid and methyl 1,2,2,6,6-pentamethyl-4-piperidyl sebacic acid), Hostavin PR25 ( Dimethyl 4-methoxybenzyl Idenemalonate), Tinuvin 312 or Hostavin vsu (ethanediamide N- (2-ethoxyphenyl) -N '-(2-ethylphenyl)), CHIMASSORB 119 FL (N, N'-bis (3-aminopropyl) ) Ethylenedia -2,4-bis [N-butyl-N- (1,2,2,6,6-pentamethyl-4-piperidyl) amino] -6-chloro-1,3,5-triazine condensate) Preferably there is.
- the surface sealant of the present invention may contain a solvent (E).
- the solvent (E) can be various organic solvents. Examples include aromatic solvents such as toluene and xylene; ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; ethers, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol monoalkyl ether, ethylene glycol dialkyl ether, Ethers such as propylene glycol or dialkyl ether; aprotic polar solvents such as N-methylpyrrolidone, dimethylimidazolidinone and dimethylformaldehyde; esters such as ethyl acetate and butyl acetate are included.
- a ketone solvent a solvent having a keto group
- the moisture content of the surface sealing agent of this invention is 0.1 mass% or less, and it is more preferable that it is 0.06 mass% or less.
- Organic EL elements are easily degraded by moisture. Therefore, it is preferable to reduce the water content of the surface sealing agent as much as possible.
- the moisture content of the surface sealant is obtained by weighing about 0.1 g of a sample sample, heating to 150 ° C. with a Karl Fischer moisture meter, and measuring the amount of water generated at that time (solid vaporization method). .
- the reaction activity expression temperature of the surface sealing agent of the present invention is appropriately adjusted depending on the heat resistance temperature of the element to be surface-sealed, but is preferably 70 to 150 ° C., more preferably 80 to 110 ° C. 90 to 100 ° C. is more preferable.
- the reaction activity expression temperature is closely related to the curing temperature of the surface sealing agent. If the reaction activity expression temperature is 150 ° C. or lower, the surface sealing agent can be heated and cured at 150 ° C. or lower, and there is little possibility of affecting the organic EL element during surface sealing with the surface sealing agent. On the other hand, if the reaction activity expression temperature is 70 ° C. or higher, the curing reaction of the epoxy resin (A) hardly occurs during storage or transportation, and the storage stability is improved.
- the reaction activity expression temperature is a value at the rise of an exothermic peak measured by differential scanning calorimetry (DSC).
- the reaction activation temperature is adjusted by the type of the epoxy resin (A) and the type of the curing accelerator (B), and particularly depends greatly on the structure of the quaternary ammonium ion contained in the curing accelerator (B).
- the surface sealant When the surface sealant is liquid, the surface sealant preferably has a viscosity (value measured at 25 ° C. and 1.0 rpm with an E-type viscometer) of 200 to 10000 mPa ⁇ s.
- a viscosity value measured at 25 ° C. and 1.0 rpm with an E-type viscometer
- the coating property for example, screen printing property
- the viscosity of the surface sealant is measured with an E-type viscometer (RC-500 manufactured by Toki Sangyo).
- the surface sealant of the present invention is produced by an arbitrary method as long as the effects of the present invention are not impaired. For example, 1) manufactured through a step of preparing an epoxy resin (A), a curing accelerator (B), and other optional components, and 2) a step of mixing each component at 30 ° C. or lower in an inert gas environment. Is done. Examples of the mixing method of each component include a method of charging each component in a flask and stirring, and a method of kneading with three rolls.
- a liquid surface sealing agent may be applied to a release substrate, the coating film dried, and then peeled off.
- the surface sealing agent can be applied by a method such as screen printing or dispenser application.
- the surface sealing agent of the present invention may be liquid or solid (sheet-like).
- the method of surface sealing the organic EL element with a liquid surface sealing agent may be a method of applying the surface sealing agent on the organic EL element by screen printing or dispenser application and curing the same.
- the method of surface-sealing an organic EL element with a sheet-like sealant may be a method of laminating and curing the surface sealant on the organic EL element.
- the cured product of the surface sealing agent of the present invention preferably has a high visible light permeability. It is preferable that the light transmittance in a wavelength region of 380 nm (visible / ultraviolet light) of a cured film obtained by curing a surface sealing agent having a thickness of 10 ⁇ m at 100 ° C. for 30 minutes is 80% or more. More preferably, it is 90% or more, More preferably, it is 95% or more. When the light transmittance is 80% or more, light emitted from the organic EL element can be efficiently extracted through the cured product of the surface sealing agent. However, when the surface sealing agent of the present invention is used in a back emission type organic EL device, the transparency of the cured product is not particularly limited.
- the organic EL device of the present invention is located between the organic EL element disposed on the display substrate, the counter substrate paired with the display substrate, the display substrate and the counter substrate, and covers the organic EL element.
- a sealing member (which seals the surface).
- the organic EL device 20 of this embodiment includes 1) an organic EL element 24 disposed on the display substrate 22, and 2) a seal that is in contact with the organic EL element 24 and covers (is surface-sealed) the organic EL element 24.
- the sealing member 28-1 is a cured product of the above-described surface sealing agent.
- a display substrate 22, an organic EL element 24, and a counter substrate 26 are laminated in this order.
- a surface sealing layer 28 is disposed between the display substrate 22 and the counter substrate 26, and the surface sealing layer 28 covers (is surface-sealed) at least the main surface of the organic EL element 24.
- the surface sealing layer 28 includes a sealing member 28-1 made of a cured product of the surface sealing agent of the present invention, and a passivation film 28 that covers the sealing member 28-1. -2 and further a second sealing material 28-3 covering the passivation film 28-2.
- the display substrate 22 and the counter substrate 26 are usually glass substrates or resin films, and at least one of the display substrate 22 and the counter substrate 26 is a transparent glass substrate or a transparent resin film.
- transparent resin films include aromatic polyester resins such as polyethylene terephthalate.
- the organic EL element 24 When the organic EL element 24 is a top emission type, the organic EL element 24 includes a pixel electrode layer 30 (made of aluminum or silver), an organic EL layer 32, and a counter electrode layer 34 (ITO) from the display substrate 22 side. And IZO).
- the pixel electrode layer 30, the organic EL layer 32, and the counter electrode layer 34 may be formed by vacuum deposition, sputtering, or the like.
- the surface sealing layer 28 includes a sealing member 28-1 made of a cured product of the surface sealing agent of the present invention, a passivation film 28-2, and a sealing material 28-3.
- the seal member 28-1 is preferably in contact with the organic EL element 24.
- the thickness of the sealing member 28-1 is preferably 0.1 to 20 ⁇ m.
- the passivation film 28-2 constituting the surface sealing layer 28 can be an inorganic compound film formed in a plasma environment, for example. Forming a film in a plasma environment refers to film formation by a plasma CVD method, for example.
- the material of the passivation film 28-2 is preferably a transparent inorganic compound, and examples thereof include silicon nitride, silicon oxide, SiONF, and SiON, but are not particularly limited.
- the thickness of the passivation film 28-2 is preferably 0.1 to 5 ⁇ m.
- the passivation film 28-2 may cover the entire surface of the seal member 28-1, or may cover only a part thereof.
- the passivation film 28-2 is not in direct contact with the organic EL element 24, and the passivation film 28-1 is laminated on the seal member 28-1. If an attempt is made to form the passivation film 28-2 in direct contact with the organic EL element 24, the edge of the organic EL element 24 is acute and the coverage by the passivation film 28 may be reduced. On the other hand, when the surface of the organic EL element 24 is sealed with the seal member 28-1, and then the passivation film 28-2 is formed on the seal member 28-1, the passivation film 28-2 is formed. The film surface can be smoothed and the coverage is improved.
- the seal member 28-1 made of a cured product of the surface sealing agent of the present invention has high plasma resistance. Therefore, even when the sealing member 28-1 is irradiated with plasma, high transparency is maintained.
- the sealing material 28-3 constituting the surface sealing layer 28 may be the same material as the sealing member 28-1 (cured product of the surface sealing agent of the present invention) or a different material.
- the moisture content of the sealing material 28-3 may be higher than the moisture content of the sealing member 28-1. This is because the sealing material 28-3 is not in direct contact with the organic EL element 24.
- the light transmittance of the sealing material 28-3 is the seal It needs to be high like the member 28-1.
- the seal member 28-1 and the passivation film 28-2 are disposed so as to be in contact with each other; Another layer (not shown) that covers a part of the seal member 28-1 may be included between the passivation film 28-2 and the passivation film 28-2. Even in such a configuration, when a passivation film is formed on another layer, the seal member 28-1 not covered with the other layer is irradiated with plasma. As described above, the seal member 28-1 made of a cured product of the surface sealing agent of the present invention has high plasma resistance. Therefore, even when the seal member 28-1 is irradiated with plasma, high transparency is maintained.
- the organic EL device 20 ′ of this embodiment includes 1) an organic EL element 24 disposed on the display substrate 22, and 2) is in contact with the organic EL element 24 and covers the organic EL element 24 (surface sealing).
- the sealing member 28-1 is a cured product of the above-described surface sealing agent.
- a display substrate 22, an organic EL element 24, and a counter substrate 26 are laminated in this order.
- a seal member 28-1 is disposed between the display substrate 22 and the counter substrate 26, and the seal member 28-1 covers the periphery of the organic EL element 24 (surface-sealing).
- Other constituent members of the organic EL device 20 ′ shown in FIG. 1B are the same as the constituent members of the organic EL device 20 shown in FIG.
- the organic EL device of the present invention can be produced by an arbitrary method as long as the effects of the present invention are not impaired, but 1) a step of preparing an organic EL element disposed on a substrate, and 2) an organic EL element, When the step of covering with a surface sealing agent and 3) the step of heat curing the surface sealing agent are included, the effect of the surface sealing agent of the present invention is particularly effectively exhibited. Moreover, you may have the process of forming a passivation film on the hardened
- the surface sealant of the present invention can be cured at a relatively low curing temperature.
- the heat curing temperature may be a temperature at which the curing accelerator (B) in the surface sealing agent is activated, preferably 70 to 150 ° C., more preferably 80 to 110 ° C., further preferably 90 to 100. ° C. If it is less than 70 degreeC, a hardening accelerator (B) cannot fully be activated and hardening of an epoxy resin (A) may become inadequate. Moreover, when it exceeds 150 degreeC, there exists a possibility of affecting an organic EL element at the time of heat-hardening.
- the heat curing can be performed by a known method such as heating with an oven or a hot plate.
- the heating time is preferably 30 to 120 minutes, more preferably 30 to 90 minutes, and further preferably 30 to 60 minutes.
- FIG. 2 schematically shows an example of the manufacturing process of the organic EL device of the present invention.
- a display substrate 22 on which an organic EL element 24 is stacked is prepared (FIG. 2A).
- the organic EL element 24 includes a pixel electrode layer 30, an organic EL layer 32, and a counter electrode layer 34, but may further include other functional layers.
- the laminated body which formed the passivation film on the sheet-like surface sealing agent of this invention is prepared.
- the passivation film (transparent inorganic compound layer) 28-2 can be formed by any method such as a plasma CVD method.
- This laminated body is laminated on the organic EL element 24 laminated on the display substrate 22 (so as to cover the counter electrode layer 34). Lamination is performed so that the organic EL element 24 and the surface sealing agent face each other. Thereafter, the surface sealant is cured to form the seal member 28-1 (FIG. 2B).
- the passivation film 28-2 is covered with a resin layer (FIG. 2C), and the counter substrate 26 is overlaid.
- the resin layer is cured to form a sealing material 28-3.
- the substrate 26 is attached (FIG. 2D). In this way, the organic EL device 20 of the present invention is obtained.
- FIG. 3 schematically shows another example of the manufacturing process of the organic EL device of the present invention.
- the display substrate 22 on which the organic EL element 24 is stacked is prepared (FIG. 3A).
- the organic EL element 24 includes a pixel electrode layer 30, an organic EL layer 32, and a counter electrode layer 34, but may further include other functional layers.
- the sheet-like liquid surface sealing agent 28-1 ′ of the present invention is applied onto the organic EL element 24, or the sheet-like surface sealing agent 28-1 ′ is laminated on the display substrate 22. Lamination is performed on the element 24 (FIG. 3B).
- the counter substrate 26 is overlaid, and in this state, the surface sealing agent is cured to form the seal member 28-1, and the counter substrate 26 is bonded together (FIG. 3C). In this way, the organic EL device 20 'of the present invention is obtained.
- Example 1 In a flask substituted with nitrogen, 100 parts by weight of an epoxy resin, 2 parts by weight of a quaternary ammonium salt (1), and 4 parts by weight of a silane coupling agent were stirred and mixed at 50 ° C. to obtain a surface sealing agent.
- an epoxy resin 100 parts by weight of an epoxy resin
- 2 parts by weight of a quaternary ammonium salt (1) 2 parts by weight of a quaternary ammonium salt (1)
- 4 parts by weight of a silane coupling agent were stirred and mixed at 50 ° C. to obtain a surface sealing agent.
- Examples 2 to 4 and Comparative Examples 1 to 5 A surface sealing agent was obtained in the same manner as in Example 1 except that an epoxy resin, an acid anhydride, a curing accelerator, and a silane coupling agent were added at a composition ratio shown in Table 1.
- the light transmittance (background data) in the wavelength region (visible / ultraviolet light) of 190 nm to 800 nm of the alkali-free glass plate was measured.
- a surface sealant was screen-printed on the same alkali-free glass plate with a film thickness of 20 ⁇ m, and this was thermally cured at 100 ° C. for 30 minutes.
- the light transmittance in the wavelength region (visible / ultraviolet light) of 190 nm to 800 nm of the cured product was measured. Thereafter, the background data was subtracted from the light transmittance data of the cured product, and the light transmittance of the cured product of the surface sealing agent was calculated.
- the evaluation was performed with a light transmittance of 380 nm.
- reaction activity expression temperature On the hot plate set to a reaction activity temperature of 45 ° C., a plurality of surface sealants were thermocompression bonded to form a sheet having a thickness of 250 to 300 ⁇ m. With respect to this sheet, the rising temperature of the exothermic peak was measured with a Haake rheometer (RS150 type) at a measurement frequency of 1 Hz, a heating rate of 4 ° C./minute, and a measurement temperature range of 40 to 150 ° C. The reaction activity expression temperature was used.
- RS150 type Haake rheometer
- the surface sealing agent was printed on a glass substrate (7 cm ⁇ 7 cm ⁇ 0.7 mm thickness) previously cleaned by ozone treatment with a screen printer (Screen Printer Model 2200, manufactured by MITANI). Printing was performed so that the dry surface sealing agent had a thickness of 5 cm ⁇ 5 cm ⁇ 3 ⁇ m.
- the glass substrate on which the surface sealing agent was printed was heated on a hot plate heated to 150 ° C. for 30 minutes to cure the surface sealing agent.
- the haze value (%) of the cured product of the surface sealant was measured with a haze meter (manufactured by Tokyo Denki, model name TC-H3DPK). Then, the cured product of the surface sealant is placed in a plasma processing apparatus (model name PDC210, parallel plate type, manufactured by Yamato Kagaku) together with the glass substrate, and plasma processing is performed for 20 minutes under conditions of an oxygen flow rate of 20 mL / min and an RF output of 500 W. did.
- the haze value (%) of the cured product of the surface sealant after the plasma treatment was measured with a haze meter (manufactured by Tokyo Denka, model name TC-H3DPK).
- the amount of increase in haze value after plasma treatment ((haze value after treatment / haze value before treatment) ⁇ 100-100) relative to the haze value before plasma irradiation is calculated, and the plasma resistance is determined by the amount of change (%). evaluated. The smaller the value, the higher the resistance to plasma. The amount of change is shown in Table 1.
- the surface sealant is applicable to a method of manufacturing an organic EL element including a step of plasma irradiation. Furthermore, the weather resistance of the surface sealing agent of the organic EL element can be accelerated and evaluated by the plasma treatment.
- the surface sealing agent was sealed between two NaCl crystal plates (2 cm square, thickness 5 mm) so that the distance between the NaCl crystal plates was 15 ⁇ m.
- the infrared transmission spectrum of this sample was measured with an FT-IR measuring apparatus. Then, it heat-processed for 30 minutes at 150 degreeC, and the infrared transmission spectrum was similarly measured with the FT-IR measuring apparatus.
- the height of the absorption peak near 910 cm ⁇ 1
- the reverse symmetric ring stretching of the epoxy group is the height of the absorption peak (near 1600 cm ⁇ 1 ) derived from the intra-CC stretching of the benzene ring. Divided by and normalized.
- the epoxy conversion rate ⁇ (x1 ⁇ x2) / x1 ⁇ ⁇ 100 (%) was calculated by setting the standard value of the epoxy group peak before heat treatment to x1 and the standard value of the epoxy group peak after heat treatment to x2.
- the curability of the surface sealant was evaluated based on the epoxy conversion rate. The higher the epoxy conversion rate, the higher the curability.
- the epoxy conversion is shown in Table 1.
- the surface sealing agents of Examples 1 to 4 including a curing accelerator made of a quaternary ammonium salt have a reaction activity expression temperature of 90 ° C. to 140 ° C. and a relatively low temperature, and are sufficiently cured within this temperature range. It was possible. Moreover, since the epoxy conversion rates of the surface sealing agents of Examples 1 and 2 both exceed 90%, it can be said that the curability of these surface sealing agents is good.
- the cured products of the surface sealants of Examples 1 to 4 containing a curing accelerator made of a quaternary ammonium salt all had a light transmittance of 90% or more at 380 nm, and had high translucency.
- cured material of the surface sealing agent of Example 1 and Example 2 had little haze deterioration also by plasma irradiation, and was excellent also in weather resistance and plasma resistance.
- the organic EL device including the organic EL element whose surface is sealed with the cured product layer of the surface sealing agent of the present invention has high transparency of the cured product layer. Moreover, since the surface sealing agent of this invention can be hardened
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Abstract
Description
[1]1分子内に2個以上のエポキシ基を有するエポキシ樹脂(A)と、下記一般式(1)で表される4級アンモニウムイオンの塩(B1)及び下記一般式(2)で表される4級アンモニウムイオンの塩(B2)からなる群から選ばれる少なくとも一種類の化合物からなる硬化促進剤(B)と、を含む有機EL素子用の面封止剤であって、前記面封止剤100重量部に対し前記硬化促進剤(B)を0.1~10重量部含む、有機EL素子用の面封止剤。
[4]前記一般式(1)のR1、R2、R3の置換基、及び前記一般式(2)のR4、R5、R6の置換基が、それぞれ独立に、炭素数が1~10のアルキル基、炭素数が1~10のアルコキシ基、F、Cl、Br、I、NO2、CN、及び下記一般式(5)で表される基からなる群から選ばれる官能基である、[1]~[3]のいずれかに記載の面封止剤。
[6]さらにシランカップリング剤(C)を含む、[1]~[5]のいずれかに記載の面封止剤。
[7]前述の[1]~[6]のいずれかに記載の面封止剤の硬化物。
[8]有機EL素子が配置された表示基板、前記表示基板と対になる対向基板、及び前記表示基板と前記対向基板との間に在り、前記有機EL素子を封止するシール部材、を含む有機ELデバイスであって、前記シール部材は[7]に記載の硬化物である、有機ELデバイス。
[9]前記[8]に記載の有機ELデバイスを備えた、有機ELパネル。
[10]有機EL素子が配置された表示基板を準備する工程と、前記有機EL素子を前記[1]~[6]のいずれかに記載の面封止剤で覆う工程と、前記面封止剤を加熱硬化する工程と、を含む有機ELデバイスの製造方法。
[12]有機EL素子と、前記有機EL素子と接し、かつ前記有機EL素子を面封止する、[1]~[6]のいずれかに記載の面封止剤の硬化物からなる硬化物層と、前記硬化物層と接するパッシベーション膜と、を含む有機ELデバイス。
本発明の面封止剤には、エポキシ樹脂(A)と、特定の4級アンモニウムイオンの塩からなる硬化促進剤(B)とが含まれ;さらに、シランカップリング剤(C)などが含まれてもよい。
本発明の面封止剤に含まれるエポキシ樹脂(A)は、1分子内に2個以上のエポキシ基を有するエポキシ樹脂であればよく、分子量などは特に限定されず、分子量分布がないエポキシ樹脂も、分子量分布があるエポキシ樹脂も用いることができる。
本発明の面封止剤に含まれる硬化促進剤(B)は、特定の4級アンモニウムイオンを含む塩(B1またはB2)からなる。
本発明の面封止剤には、シランカップリング剤、チタン系カップリング剤、ジルコニウム系カップリング剤、アルミニウム系カップリング剤などのカップリング剤(C)が含まれてもよい。カップリング剤(C)が含まれる面封止剤は、有機ELデバイスの基板等との密着性が高い。
本発明の面封止剤には、本発明の効果を損なわない範囲で、その他の任意成分(D)が含まれてもよい。その他の任意成分(D)の例には、樹脂成分、充填剤、改質剤、酸化防止剤、安定剤、酸無水物等が含まれる。
本発明の面封止剤には、溶剤(E)が含まれてもよい。溶剤(E)が含まれると、各成分が均一に分散または溶解される。溶剤(E)は、各種有機溶剤であり得る。その例には、トルエン、キシレン等の芳香族溶媒;アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン系溶媒;エーテル、ジブチルエーテル、テトラヒドロフラン、ジオキサン、エチレングリコ-ルモノアルキルエーテル、エチレングリコ-ルジアルキルエーテル、プロピレングリコールまたはジアルキルエーテル等のエーテル類;N-メチルピロリドン、ジメチルイミダゾリジノン、ジメチルフォルムアルデヒド等の非プロトン性極性溶媒;酢酸エチル、酢酸ブチル等のエステル類等が含まれる。特に、高分子量のエポキシ樹脂(A)を溶解し易い点から、メチルエチルケトン等のケトン系溶媒(ケト基を有する溶媒)がより好ましい。
本発明の面封止剤の含水率は、0.1質量%以下であることが好ましく、0.06質量%以下であることがより好ましい。有機EL素子は水分により劣化しやすい。したがって、面封止剤の含水率をできるだけ低減することが好ましい。面封止剤の含水率は、試料サンプルを約0.1g計量し、カールフィッシャー水分計にて150℃に加熱し、その際に発生する水分量を測定することで求められる(固体気化法)。
本発明の有機ELデバイスは、表示基板上に配置された有機EL素子と、表示基板と対になる対向基板と、表示基板と対向基板との間に在り、有機EL素子を覆う(面封止する)シール部材とを含む。
以下に、実施例及び比較例の面封止剤に添加した原材料を下記に示す。
<エポキシ樹脂>
・ビスフェノールF型エポキシ樹脂:分子量338(YL-983U、ジャパンエポキシレジン社製)
・3官能エポキシ樹脂:分子量592(VG-3101L、プリンテック社製)
・下記式で表す4級アンモニウム塩(1)(King Industry社製)
・1-ベンジル-2-メチルイミダゾール(キュアゾール 1B2MZ、四国化成製)
・2-エチル-4-メチルイミダゾール(キュアゾール 2E4MZ、四国化成製)
・メチルヘキサヒドロ無水フタル酸とヘキサヒドロ無水フタル酸との混合物(リカシッドMH-700、新日本理化製)
<シランカップリング剤>
・3-グリシドキシプロピルトリメトキシシラン(信越化学(株)製 KBM403、1分子当たりのアルコキシ基数:3、分子量:236.3)
窒素で置換したフラスコで、エポキシ樹脂100重量部と、2重量部の4級アンモニウム塩(1)と、4重量部のシランカップリング剤とを、50℃で攪拌混合して、面封止剤を得た。
エポキシ樹脂、酸無水物、硬化促進剤、及びシランカップリング剤を、表1に示す組成比で添加した以外は、実施例1と同様に面封止剤を得た。
E型粘度計(東機産業製 RC-500)にて、25℃、1.0rpmで面封止剤の粘度を測定した。測定は、調製直後のサンプル、25℃で24時間保存後のサンプル、25℃で48時間保存後のサンプルについて行った。測定結果を表1に示す。
無アルカリガラス板の190nm~800nmの波長領域(可視・紫外光)の光線透過率(バックグラウンドデータ)を測定した。同じ無アルカリガラス板に膜厚20μmで、面封止剤をスクリーン印刷し、これを100℃で30分熱硬化させた。硬化物の190nm~800nmの波長領域(可視・紫外光)の光線透過率を測定した。その後、硬化物の光線透過率データから、バックグラウンドデータを減算し、面封止剤の硬化物の光線透過率を算出した。評価は380nmの光線透過率で行った。
反応活性発現温度は、45℃に設定したホットプレート上で、面封止剤を複数層熱圧着し、膜厚250~300μmのシートとした。このシートについて、Haake社製レオメーター(RS150型)で、測定周波数:1Hz、昇温速度:4℃/分、測定温度範囲:40~150℃で発熱ピークの立ち上がり温度を測定し、前記温度を反応活性発現温度とした。
面封止剤を、予めオゾン処理によって洗浄したガラス基板(7cm×7cm×0.7mm厚)に、スクリーン印刷機(Screen Printer Model 2200、MITANI製)で印刷した。印刷は、乾燥状態の面封止剤が5cm×5cm×3μm厚となるように行った。面封止剤を印刷したガラス基板を、150℃に加熱したホットプレート上で30分間加熱して、面封止剤硬化させた。
面封止剤を、2枚のNaCl結晶板(2センチ角、厚み5mm)の間に封入し、NaCl結晶板同士の間隔が15μmとなるようにした。このサンプルの赤外線透過スペクトルを、FT-IR測定装置で測定した。その後、150℃で30分熱処理し、同様に赤外線透過スペクトルを、FT-IR測定装置で測定した。それぞれの測定スペクトルにおける、エポキシ基の逆対称環伸縮に由来する吸収ピーク(910cm-1付近)高さを、ベンゼン環の環内C-C伸縮に由来する吸収ピーク(1600cm-1付近)高さで除して規格化した。
22 表示基板
24 有機EL素子
26 対向基板
28 面封止層
28-1 シール部材
28-2 パッシベーション膜
28-3 封止材
28-1’ 面封止剤
30 画素電極層
32 有機EL層
34 対向電極層
Claims (12)
- 1分子内に2個以上のエポキシ基を有するエポキシ樹脂(A)と、
下記一般式(1)で表される4級アンモニウムイオンの塩(B1)及び下記一般式(2)で表される4級アンモニウムイオンの塩(B2)からなる群から選ばれる少なくとも一種類の化合物からなる硬化促進剤(B)と、を含む有機EL素子用の面封止剤であって、
前記面封止剤100重量部に対し前記硬化促進剤(B)を0.1~10重量部含む、有機EL素子用の面封止剤。
R1、R2、R3はそれぞれ独立に、置換基を有してもよい炭素数1~10のアルキル基、置換基を有してもよい炭素数6~10のアリール基、または置換基を有してもよい炭素数7~20のアラルキル基を表し、
Arは置換基を有してもよい炭素数6~10のアリール基を表す。)
R4、R5、R6はそれぞれ独立に、置換基を有してもよい炭素数1~10のアルキル基、置換基を有してもよい炭素数6~10のアリール基、または置換基を有してもよい炭素数7~20のアラルキル基を表し、
Ra、Rb、Rcはそれぞれ独立に、水素基または炭素数が1~10のアルキル基、炭素数が1~10のアルコキシ基、F、Cl、Br、I、NO2、CN、または下記一般式(3)で表される基を表す。)
- 前記一般式(1)のArに結合する置換基が、炭素数が1~10のアルキル基、炭素数が1~10のアルコキシ基、及び前記一般式(4)で表される基からなる群から選ばれる官能基である、請求項2に記載の面封止剤。
- 前記塩(B1)または前記塩(B2)の対アニオンが、[CF3SO3]-、[C4F9SO3]-、[PF6]-、[AsF6]-、[Ph4B]-、Cl-、Br-、I-、[OC(O)R16]-(R16は炭素数1~10のアルキル基を表す)、[SbF6]-、[B(C6F5)4]-、[B(C6H4CF3)4]-、[(C6F5)2BF2]-、[C6F5BF3]-、及び[B(C6H3F2)4]-からなる群から選ばれる、請求項1に記載の面封止剤。
- さらにシランカップリング剤(C)を含む、請求項1に記載の面封止剤。
- 請求項1に記載の面封止剤の硬化物。
- 有機EL素子が配置された表示基板、
前記表示基板と対になる対向基板、
及び前記表示基板と前記対向基板との間に在り、前記有機EL素子を封止するシール部材、を含む有機ELデバイスであって、
前記シール部材は請求項7に記載の硬化物である、有機ELデバイス。 - 請求項8に記載の有機ELデバイスを備えた、有機ELパネル。
- 有機EL素子が配置された表示基板を準備する工程と、
前記有機EL素子を請求項1に記載の面封止剤で覆う工程と、
前記面封止剤を加熱硬化する工程と、を含む有機ELデバイスの製造方法。 - 前記面封止剤の硬化物上に、パッシベーション膜を成膜する工程をさらに有する、請求項10に記載の有機ELデバイスの製造方法。
- 有機EL素子と、
前記有機EL素子と接し、かつ前記有機EL素子を面封止する、請求項1に記載の面封止剤の硬化物からなる硬化物層と、
前記硬化物層と接するパッシベーション膜と、を含む有機ELデバイス。
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JP2017186521A (ja) * | 2016-03-31 | 2017-10-12 | 三井化学株式会社 | 熱硬化性組成物、これを含む封止剤、有機el素子用枠封止剤、及び有機el素子用面封止剤、並びにその硬化物 |
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KR101682781B1 (ko) | 2016-12-05 |
US20140367670A1 (en) | 2014-12-18 |
KR20140119077A (ko) | 2014-10-08 |
TWI622603B (zh) | 2018-05-01 |
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