JP7197609B2 - 封止剤、硬化体、有機エレクトロルミネッセンス表示装置、及び装置の製造方法 - Google Patents
封止剤、硬化体、有機エレクトロルミネッセンス表示装置、及び装置の製造方法 Download PDFInfo
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- JP7197609B2 JP7197609B2 JP2020566489A JP2020566489A JP7197609B2 JP 7197609 B2 JP7197609 B2 JP 7197609B2 JP 2020566489 A JP2020566489 A JP 2020566489A JP 2020566489 A JP2020566489 A JP 2020566489A JP 7197609 B2 JP7197609 B2 JP 7197609B2
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- polymerizable monomer
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- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 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
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- MGACORKJUSACCA-UHFFFAOYSA-N trinaphthalen-1-ylsulfanium Chemical compound C1=CC=C2C([S+](C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MGACORKJUSACCA-UHFFFAOYSA-N 0.000 description 1
- HKDYXDHJQBAOAC-UHFFFAOYSA-N trinaphthalen-2-ylsulfanium Chemical compound C1=CC=CC2=CC([S+](C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 HKDYXDHJQBAOAC-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- AXYQQAVHPAUFQX-UHFFFAOYSA-N tris(2-methylphenyl)sulfanium Chemical compound CC1=CC=CC=C1[S+](C=1C(=CC=CC=1)C)C1=CC=CC=C1C AXYQQAVHPAUFQX-UHFFFAOYSA-N 0.000 description 1
- MAOCPIDAEMTJLK-UHFFFAOYSA-N tris(4-fluorophenyl)sulfanium Chemical compound C1=CC(F)=CC=C1[S+](C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 MAOCPIDAEMTJLK-UHFFFAOYSA-N 0.000 description 1
- XUWXFPUSCUUNPR-UHFFFAOYSA-O tris(4-hydroxyphenyl)sulfanium Chemical compound C1=CC(O)=CC=C1[S+](C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 XUWXFPUSCUUNPR-UHFFFAOYSA-O 0.000 description 1
- WUKMCKCDYKBLBG-UHFFFAOYSA-N tris(4-methoxyphenyl)sulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WUKMCKCDYKBLBG-UHFFFAOYSA-N 0.000 description 1
- QKFJVDSYTSWPII-UHFFFAOYSA-N tris(4-methylphenyl)sulfanium Chemical compound C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 QKFJVDSYTSWPII-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920001567 vinyl ester resin Chemical group 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—Acrylamide; Methacrylamide
-
- 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
- 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
- C08G59/22—Di-epoxy compounds
-
- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Sealing Material Composition (AREA)
- Polyethers (AREA)
- Polymerisation Methods In General (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
<1>重合性モノマーと重合開始剤とを含有し、23℃雰囲気下における比重が1.3以上であり、硬化体の23℃雰囲気下における比重が1.3~3.0である、封止剤。
<2>硬化体の60℃雰囲気下における比重が1.3~3.0である、<1>に記載の封止剤。
<3>硬化体のガラス転移温度が60℃以上である<1>又は<2>に記載の封止剤。
<4>硬化体の架橋密度が1.0×10-3mol/cm3以上である<1>~<3>のいずれかに記載の封止剤。
<5>重合性モノマーが、原子番号9以上の元素を有する重合性モノマー(X)を含有する<1>~<4>のいずれかに記載の封止剤。
<6>重合性モノマー(X)が、ハロゲン族元素を有する<5>に記載の封止剤。
<7>重合性モノマー(X)が、フッ素元素及び臭素元素からなる群より選択される少なくとも一種を有する<5>又は<6>に記載の封止剤。
<8>重合性モノマー(X)に含まれるハロゲン族元素の含有量が、重合性モノマーの総元素量に対して、10~50質量%ある<7>に記載の封止剤。
<9>重合性モノマーが、重合性官能基を2個以上有する架橋性モノマー(Y)を含有する<1>~<8>のいずれか一項に記載の封止剤。
<10>重合開始剤が、光重合開始剤である<1>~<9>のいずれかに記載の封止剤。
<11>重合性モノマーが、芳香環を有するモノマーを含有する<1>~<10>のいずれかに記載の封止剤。
<12>重合性モノマーが、カチオン重合性官能基及びラジカル重合性官能基からなる群より選択される少なくとも一種を有する<1>~<11>のいずれかに記載の封止剤。
<13>重合性モノマーが、グリシジルエーテル化合物、脂環式エポキシ化合物、ビニルエーテル化合物及びオキセタン化合物からなる群より選択される少なくとも1種を含有する<12>に記載の封止剤。
<14>重合開始剤が、オニウム塩を含有する<13>に記載の封止剤。
<15>重合性モノマーが、(メタ)アクリレート及び(メタ)アクリルアミドからなる群より選択される少なくとも1種を含有する<12>に記載の封止剤。
<16>重合開始剤が、光ラジカル重合開始剤を含有する<15>に記載の封止剤。
<17>重合性モノマー100質量部中、原子番号9以上の元素を有する重合性モノマー(X)の含有量が、40~90質量部である<1>~<16>のいずれかに記載の封止剤。
<18>重合性モノマーの100質量部中、重合性官能基を2個以上有する架橋性モノマー(Y)の含有量が、5~60質量部である<1>~<17>のいずれかに記載の封止剤。
<19>重合性モノマーの100質量部に対して、重合開始剤の含有量が、0.01~5質量部である<1>~<18>のいずれかに記載の封止剤。
<20>硬化体の、JIS Z0208に準拠して、温度60℃、相対湿度90%の条件下で測定される、100μm厚での透湿度が40g/m2以下である<1>~<19>のいずれかに記載の封止剤。
<21>硬化体の、厚さ10μm当たりの360nm以上800nm以下の紫外-可視光線領域の光透過率が、95%以上である<1>~<20>のいずれかに記載の封止剤。
<22>有機エレクトロルミネッセンス素子用封止剤である、<1>~<21>のいずれかに記載の封止剤。
<23>第一の部材と第二の部材とを含む装置の製造方法であって、第一の部材に、<1>~<22>のいずれかに記載の封止剤を付着させる付着工程と、付着させた封止剤に光を照射する照射工程と、光照射された封止剤を介して、第一の部材と第二の部材とを貼り合わせる貼合工程と、を備える、装置の製造方法。
<24>第一の部材が有機エレクトロルミネッセンス素子であり、第二の部材が基板であり、装置が有機エレクトロルミネッセンス表示装置である、<23>に記載の装置の製造方法。
<25>第一の部材が基板であり、第二の部材が有機エレクトロルミネッセンス素子であり、装置が有機エレクトロルミネッセンス表示装置である、<23>に記載の装置の製造方法。
<26><1>~<22>のいずれかに記載の封止剤の硬化体。
<27>有機エレクトロルミネッセンス素子と、<26>に記載の硬化体と、を含む、有機エレクトロルミネッセンス表示装置。
<28>無機膜と有機膜とが積層した積層体を含み、有機膜が<26>に記載の硬化体を含む、有機エレクトロルミネッセンス表示装置。
<29>無機膜と有機膜とが積層した積層体を含み、有機エレクトロルミネッセンス素子に直接積層した有機膜が、<26>に記載の硬化体を含む、有機エレクトロルミネッセンス表示装置。
<30>フッ素元素及び臭素元素からなる群より選択される少なくとも一種を有する重合性モノマー(X)と、重合開始剤と、を含有する組成物。
・溶媒(移動相):THF
・脱気装置:ERMA社製ERC-3310
・ポンプ:日本分光社製PU-980
・流速:1.0ml/min
・オートサンプラ:東ソー社製AS-8020
・カラムオーブン:日立製作所製L-5030
・設定温度:40℃
・カラム構成:東ソー社製TSKguardcolumnMP(×L)6.0mmID×4.0cm 2本、及び東ソー社製TSK-GELMULTIPORE HXL-M 7.8mmID×30.0cm 2本、計4本
・検出器:RI 日立製作所製L-3350
・データ処理:SIC480データステーション
これらの中では、ビスフェノール構造を有する芳香族エポキシ化合物が好ましい。ビスフェノール構造を有する芳香族エポキシ化合物の中では、下記式(A2-1)で表される化合物が好ましい。
[(Rf)bPF6-b]- (B-1-3)
ベンゾフェノン及びその誘導体;
ベンジル及びその誘導体;
アントラキノン及びその誘導体;
ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインプロピルエーテル、ベンゾインイソブチルエーテル、ベンジルジメチルケタール等のベンゾイン型光重合開始剤;
ジエトキシアセトフェノン、4-tert-ブチルトリクロロアセトフェノン等のアセトフェノン型光重合開始剤;
2-ジメチルアミノエチルベンゾエート;
p-ジメチルアミノエチルベンゾエート;
ジフェニルジスルフィド;
チオキサントン及びその誘導体;
カンファーキノン、7,7-ジメチル-2,3-ジオキソビシクロ[2.2.1]ヘプタン-1-カルボン酸、7,7-ジメチル-2,3-ジオキソビシクロ[2.2.1]ヘプタン-1-カルボキシ-2-ブロモエチルエステル、7,7-ジメチル-2,3-ジオキソビシクロ[2.2.1]ヘプタン-1-カルボキシ-2-メチルエステル、7,7-ジメチル-2,3-ジオキソビシクロ[2.2.1]ヘプタン-1-カルボン酸クロライド等のカンファーキノン型光重合開始剤;
2-メチル-1-[4-(メチルチオ)フェニル]-2-モルフォリノプロパン-1-オン、2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン-1等のα-アミノアルキルフェノン型光重合開始剤;
ベンゾイルジフェニルホスフィンオキサイド、2,4,6-トリメチルベンゾイル-ジフェニル-ホスフィンオキサイド、ベンゾイルジエトキシホスフィンオキサイド、2,4,6-トリメチルベンゾイルジメトキシフェニルホスフィンオキサイド、2,4,6-トリメチルベンゾイルジエトキシフェニルホスフィンオキサイド、ビス(2,4,6―トリメチルベンゾイル)-フェニルホスフィンオキサイド等のアシルホスフィンオキサイド型光重合開始剤;
2-ヒドロキシ-2-メチル-1-フェニルプロパン-1-オン、2-ヒドロキシ-2-メチル-1-〔4-(2-ヒドロキシエトキシ)フェニル〕プロパン-1-オン、1-ヒドロキシシクロヘキシルフェニルケトン、2-ヒドロキシ-2-メチル-1-〔4-(1-メチルビニル)フェニル〕プロパン-1-オン等のα-ヒドロキシアルキルフェノン型光重合開始剤;
フェニル-グリオキシリックアシッド-メチルエステル;
オキシ-フェニル-アセチックアシッド2-[2-オキソ-2-フェニル-アセトキシ-エトキシ]-エチルエステル;
オキシ-フェニル-アセチックアシッド2-[2-ヒドロキシ-エトキシ]-エチルエステル;
等が挙げられる。
架橋密度(ρ)=G’Tg+40/3φRT
有機エレクトロルミネッセンス表示装置は、無機膜と有機膜とが積層した積層体を含んでもよい。有機膜は、本実施形態に係る組成物の硬化体を含んでもよい。有機エレクトロルミネッセンス表示装置において、有機エレクトロルミネッセンス素子に直接積層した有機膜は、本実施形態に係る組成物の硬化体を含んでもよい。
(X-1)ジブロモフェニルグリシジルエーテル(日本化薬社製「BR-250」、臭素元素の含有量51質量%)
(X-2)臭素化クレジルグリシジルエーテル(日本化薬社製「BROC」、臭素元素の含有量50質量%)
(X-3)TBBPAエポキシ樹脂(テトラブロモビスフェノールAのジグリシジルエーテル、DIC社「エピクロン152」、臭素元素の含有量48質量%)
(X-4)臭素化フェノールノボラック型エポキシ樹脂(日本化薬社製「BREN-105」、臭素元素の含有量36質量%)
(X’-1)フェニルグリシジルエーテル(阪本薬品工業社「PEG」)
(X-5)ペンタフルオロフェニルアクリレート(東京化成工業社製「ペンタフルオロフェニルアクリレート」)
(X-6)アクリル酸2,4,6-トリブロモフェニル(東京化成工業社製「トリブロモフェニルアクリレート」)
(X’-2)フェニルアクリレート(東京化成工業社製「フェニルアクリレート」)
(X’-3)イソボルニルアクリレート(共栄社化学社製「ライトアクリレートIB-XA」)
(X’-4)イソボルニルメタクリレート(共栄社化学社製「ライトエステル IB-X」)
(Y-1)3’,4’-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート(ダイセル化学社製「セロキサイド2021P」)
(Y-2)ビスフェノールA型エポキシ樹脂(三菱化学社製「jER828」、分子量360~390)
(Y-3)ジ(1-エチル-(3-オキセタニル))メチルエーテル(東亞合成社製「アロンオキセタンOXT-221」)
(Y-4)シクロヘキサンジメタノールジビニルエーテル(日本カーバイド社製「CHDVE」)
(Y-5)1,6-ヘキサンジオールジメタクリレート(新中村化学社製「HD-N」)
(Y-6)トリシクロデカンジメタノールジメタクリレート(新中村化学社製「DCP」)
・トリアリールスルホニウム塩ヘキサフルオロアンチモネート(ADEKA社製「アデカオプトマーSP-170」、アニオン種はヘキサフルオロアンチモネート)
・トリアリールスルホニウム塩(ジフェニル4-チオフェノキシフェニルスルホニウムトリス(ペンタフルオロエチル)トリフルオロホスフェート、サンアプロ社製「CPI-200K」、アニオン種はリン化合物)
・2,4,6-トリメチルベンゾイル-ジフェニル-ホスフィンオキサイド(BASFジャパン社製「TPO」)
・1-ヒドロキシシクロヘキシルフェニルケトン、BASFジャパン社製「I-184」)
9,10-ジブトキシアントラセン(川崎化成工業社製「ANTHRACURE UVS-1331」)
γ-グリシドキシプロピルトリメトキシシラン(信越シリコーン社製「KBM-403」)
微粒子タルク、粒子径(d50):4.5μm(松村産業社製「#5000PJ」)
カチオン重合性官能基を有する重合性モノマーについて試験した。表1~2に示す種類の原材料を、表1~2に示す組成割合で混合し、実験例の組成物を調製し、封止剤とした。組成割合の単位は質量部である。
実験例の組成物について、下記の各測定を行った。その結果を表1~2に示した。
ラジカル重合性官能基を有する重合性モノマーについて試験した。表3に示す種類の原材料を、表3に示す組成割合で混合し、実験例の組成物を調製し、封止剤とした。組成割合の単位は質量部である。
実験例の組成物について、下記の各測定を行った。その結果を表3に示した。
組成物の粘度(せん断粘度)はE型粘度計(1°34’×R24のコーンローター)を用い、温度25℃、回転数10rpmの条件下で測定した。
重合性モノマーの比重は、ハーバート形比重瓶を用い、JIS K0061に倣い、測定を行った。
〔組成物の比重〕
組成物の比重は、ハーバート形比重瓶を用い、JIS K0061に倣い、測定を行った。
組成物の硬化性及び接着性の評価に際し、下記光照射条件により、組成物を硬化させた。無電極放電メタルハライドランプ搭載UV硬化装置(フュージョン社製)により、365nmの波長の積算光量4,000mJ/cm2の条件にて、組成物を光硬化させた後、80℃のオーブン中で、30分間の後加熱処理を実施し、硬化体を得た。
厚さ1mmのシート状の硬化体を前記光硬化条件にて作製し、JIS K7112 B法に準拠し、硬化体の比重を測定した。浸せき液として、温度は23℃の水を使用した。
厚さ1mmのシート状の硬化体を前記光硬化条件にて作製し、JIS K7112 B法に準拠し、硬化体の比重を測定した。浸せき液として、温度は60℃の水を使用した。
厚さ0.1mmのシート状の硬化体を前記光硬化条件にて作製し、厚み100μmの硬化体を幅5mm×長さ25mmに切り出し、試験片とした。この試験片について、温度範囲-50℃~200℃、昇温速度2℃/min、引っ張りモードの条件で、動的粘弾性測定を行った。上記動的粘弾性測定で測定されたtanδ(損失正接)のピークトップの温度を硬化体のガラス転移温度(Tg)とした。
厚さ0.1mmのシート状の硬化体を前記光硬化条件にて作製し、厚み100μmの硬化体を幅5mm×長さ25mmに切り出し、試験片とした。この試験片について、温度範囲-50~200℃、昇温速度2℃/min、引っ張りモードの条件で、動的粘弾性測定を行った。架橋密度は、Tg+40℃の温度をT(K)、T(K)における貯蔵弾性率(G’)をG’Tg+40、気体定数をR、フロント係数をφ(=1)として、以下の式で算出した。
架橋密度(ρ)=G’Tg+40/3φRT
組成物を用い、硬化体の厚みが10μmとなるように、2枚のガラス板(大きさ:40mm×20mm)で貼り合せた。前記光硬化条件にて組成物を硬化したものを試験片とした。分光光度計(日本分光株式会社)を用いて、波長400nmの光透過率を測定した。
厚さ0.1mmのシート状の硬化体を前記光硬化条件にて作製し、JIS Z0208「防湿包装材料の透湿度試験方法(カップ法)」に準じ、吸湿剤として塩化カルシウム(無水)を用い、雰囲気温度60℃、相対湿度90%の条件で測定した。透湿度は120g/(m2・24hr)以下が好ましい。
ホウ珪酸ガラス試験片(縦25mm×横25mm×厚2.0mm、テンパックス(登録商標)ガラス)を2枚用い、接着面積0.5cm2、接着厚み80μmで、上記の光硬化条件にて組成物を硬化させた。硬化後、組成物で接合した試験片を用い、引張剪断接着強さ(単位:MPA)を、温度23℃、相対湿度50%の環境下で、引張速度10mm/分で測定した。
〔有機EL素子基板の作製〕
ITO電極付きガラス基板をアセトン、イソプロパノールそれぞれを用いて洗浄した。その後、真空蒸着法にて以下の化合物を薄膜となるように順次蒸着し、陽極/正孔注入層/正孔輸送層/発光層/電子注入層/陰極からなる有機EL素子基板を得た。各層の構成は以下の通りである。
・陽極 ITO、陽極の膜厚250nm
・正孔注入層 銅フタロシアニン 厚さ30nm
・正孔輸送層 N,N’-ジフェニル-N,N’-ジナフチルベンジジン(α-NPD) 厚さ20nm
・発光層 トリス(8-ヒドロキシキノリナト)アルミニウム(金属錯体系材料)、発光層の膜厚1000Å
・電子注入層 フッ化リチウム 厚さ1nm
・陰極 アルミニウム、陽極の膜厚250nm
実験例で得られた封止剤を、窒素雰囲気下にて塗工装置にてガラスに塗布し、有機EL素子基板と貼り合わせ、接着厚み10μmで前記光硬化条件にて、この封止剤を硬化させ、有機EL素子を作製した。有機EL素子基板の陽極側を、封止剤を介してガラスに貼り合わせた。
〔初期〕
作製した直後の有機EL素子に、6Vの電圧を印加し、有機EL素子の発光状態を目視と顕微鏡で観察し、ダークスポットの直径を測定した。
作製した直後の有機EL素子を、85℃、相対湿度85質量%の条件下にて1000時間暴露した後、6Vの電圧を印加し、有機EL素子の発光状態を目視と顕微鏡で観察し、ダークスポットの直径を測定した。
本実施形態は、電子デバイスの封止、有機EL素子の封止等に用いられる。
本実施形態によれば、透明性を損なわずに防湿性に優れ、かつ、ガラス基板等との接着性に優れ、凹凸浸透性に優れた封止剤を形成できる、低透湿性樹脂組成物が得られる。
本発明に係る実施形態によれば、有機EL素子用封止剤や有機EL表示装置が得られる。
Claims (25)
- 重合性モノマーと重合開始剤とを含有し、
23℃雰囲気下における比重が1.3以上であり、
硬化体の23℃雰囲気下における比重が1.3~3.0であり、
前記重合性モノマーが、(メタ)アクリレート及び(メタ)アクリルアミドからなる群より選択される少なくとも1種を含有する、封止剤。 - 前記硬化体の60℃雰囲気下における比重が1.3~3.0である、請求項1に記載の封止剤。
- 前記硬化体のガラス転移温度が60℃以上である請求項1又は2に記載の封止剤。
- 前記硬化体の架橋密度が1.0×10-3mol/cm3以上である請求項1~3のいずれか一項に記載の封止剤。
- 前記重合性モノマーが、原子番号9以上の元素を有する重合性モノマー(X)を含有する請求項1~4のいずれか一項に記載の封止剤。
- 前記重合性モノマー(X)が、ハロゲン族元素を有する請求項5に記載の封止剤。
- 前記重合性モノマー(X)が、フッ素元素及び臭素元素からなる群より選択される少なくとも一種を有する請求項5又は6に記載の封止剤。
- 前記重合性モノマー(X)に含まれるハロゲン族元素の含有量が、前記重合性モノマーの総元素量に対して、10~50質量%ある請求項7に記載の封止剤。
- 前記重合性モノマーが、重合性官能基を2個以上有する架橋性モノマー(Y)を含有する請求項1~8のいずれか一項に記載の封止剤。
- 前記重合開始剤が、光重合開始剤である請求項1~9のいずれか一項に記載の封止剤。
- 前記重合性モノマーが、芳香環を有するモノマーを含有する請求項1~10のいずれか一項に記載の封止剤。
- 前記重合開始剤が、光ラジカル重合開始剤である請求項1~11のいずれか一項に記載の封止剤。
- 前記重合性モノマー100質量部中、原子番号9以上の元素を有する重合性モノマー(X)の含有量が、40~90質量部である請求項1~12のいずれか一項に記載の封止剤。
- 前記重合性モノマーの100質量部中、重合性官能基を2個以上有する架橋性モノマー(Y)の含有量が、5~60質量部である請求項1~13のいずれか一項に記載の封止剤。
- 前記重合性モノマーの100質量部に対して、前記重合開始剤の含有量が、0.01~5質量部である請求項1~14のいずれか一項に記載の封止剤。
- 前記硬化体の、JIS Z0208に準拠して、温度60℃、相対湿度90%の条件下で測定される、100μm厚での透湿度が40g/m2以下である請求項1~15のいずれか一項に記載の封止剤。
- 前記硬化体の、厚さ10μm当たりの360nm以上800nm以下の紫外-可視光線領域の光透過率が、95%以上である請求項1~16のいずれか一項に記載の封止剤。
- 有機エレクトロルミネッセンス素子用封止剤である、請求項1~17のいずれか一項に記載の封止剤。
- 第一の部材と第二の部材とを含む装置の製造方法であって、
前記第一の部材に、請求項1~18のいずれか一項に記載の封止剤を付着させる付着工程と、
付着させた前記封止剤に光を照射する照射工程と、
光照射された前記封止剤を介して、前記第一の部材と前記第二の部材とを貼り合わせる貼合工程と、
を備える、装置の製造方法。 - 前記第一の部材が有機エレクトロルミネッセンス素子であり、
前記第二の部材が基板であり、
前記装置が有機エレクトロルミネッセンス表示装置である、
請求項19に記載の装置の製造方法。 - 前記第一の部材が基板であり、
前記第二の部材が有機エレクトロルミネッセンス素子であり、
前記装置が有機エレクトロルミネッセンス表示装置である、
請求項19に記載の装置の製造方法。 - 請求項1~18のいずれか一項に記載の封止剤の硬化体。
- 有機エレクトロルミネッセンス素子と、請求項22に記載の硬化体と、を含む、有機エレクトロルミネッセンス表示装置。
- 無機膜と有機膜とが積層した積層体を含み、
前記有機膜が請求項22に記載の硬化体を含む、有機エレクトロルミネッセンス表示装置。 - 無機膜と有機膜とが積層した積層体を含み、
有機エレクトロルミネッセンス素子に直接積層した有機膜が、請求項22に記載の硬化体を含む、有機エレクトロルミネッセンス表示装置。
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