JP6053810B2 - 有機電子装置封止用光硬化型粘接着フィルム、有機電子装置及びその封止方法 - Google Patents
有機電子装置封止用光硬化型粘接着フィルム、有機電子装置及びその封止方法 Download PDFInfo
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- JP6053810B2 JP6053810B2 JP2014542251A JP2014542251A JP6053810B2 JP 6053810 B2 JP6053810 B2 JP 6053810B2 JP 2014542251 A JP2014542251 A JP 2014542251A JP 2014542251 A JP2014542251 A JP 2014542251A JP 6053810 B2 JP6053810 B2 JP 6053810B2
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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 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001669 calcium Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
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- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
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- 150000002118 epoxides Chemical group 0.000 description 1
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- VIBDJEWPNNCFQO-UHFFFAOYSA-N ethane-1,1,2-triol Chemical compound OCC(O)O VIBDJEWPNNCFQO-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
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- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000005647 linker group Chemical group 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
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- JKJJSJJGBZXUQV-UHFFFAOYSA-N methyl 2-methylidenebutanoate Chemical compound CCC(=C)C(=O)OC JKJJSJJGBZXUQV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 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
- WYOXPIKARMAQFM-UHFFFAOYSA-N n,n,n',n'-tetrakis(oxiran-2-ylmethyl)ethane-1,2-diamine Chemical compound C1OC1CN(CC1OC1)CCN(CC1OC1)CC1CO1 WYOXPIKARMAQFM-UHFFFAOYSA-N 0.000 description 1
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- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
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- 230000035515 penetration Effects 0.000 description 1
- AOLPZAHRYHXPLR-UHFFFAOYSA-I pentafluoroniobium Chemical compound F[Nb](F)(F)(F)F AOLPZAHRYHXPLR-UHFFFAOYSA-I 0.000 description 1
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- 229920000307 polymer substrate Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
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- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
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- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
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- UOMUPDCRXJLVGR-UHFFFAOYSA-N propane-1,2,2-triol Chemical compound CC(O)(O)CO UOMUPDCRXJLVGR-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000003748 selenium group Chemical class *[Se]* 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 description 1
- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- HDUMBHAAKGUHAR-UHFFFAOYSA-J titanium(4+);disulfate Chemical compound [Ti+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O HDUMBHAAKGUHAR-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
- 229950001353 tretamine Drugs 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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
- H10K50/844—Encapsulations
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
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- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
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- 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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- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
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- C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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- C09J133/12—Homopolymers or copolymers of methyl methacrylate
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- C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
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- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
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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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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2170/00—Compositions for adhesives
- C08G2170/40—Compositions for pressure-sensitive adhesives
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
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- C09J2433/00—Presence of (meth)acrylic polymer
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Description
ブチルアクリレート15重量部、メチルエチルアクリレート40重量部、イソボニルアクリレート20重量部、メチルアクリレート15重量部及びヒドロキシエチルアクリレート10重量部の粘着剤を重合して、ガラス転移温度が、約−20℃であり、重量平均分子量が、50万のアクリル系重合体を製造した。
イソシアネート架橋剤を除外させてコーティング溶液を製造したことの以外の全ての過程は、前記実施例1と同一に実行した。
前記エポキシ樹脂でYD−128(KUKDO化学製)5重量部を使用したことの以外は、実施例1と同一に実行した。
前記実施例1で使用したアクリル系重合体のみを使用し、イソシアネート系架橋剤、トリメチルーロプロパンタイプのエポキシ樹脂及びトリアリールするホニウム塩タイプの陽イオン光重合開始剤を使用しないことの以外は、実施例1と同一に実行した。
前記実施例1で使用したトリメテロールプロパンタイプのエポキシ樹脂(SR−TMP、SAKAMOTO社製)40重量部を使用したことの以外は、実施例1と同一に実行した。
実施例1及び比較例1〜比較例4の接着フィルムの粘接着層の光照射の前後の粘度をARESで測定して、下記表1に示した。
前記実施例1及び比較例1〜比較例4で製造された粘接着フィルムを熱硬化してMOCON社のPERMATRAN−W Model 3/61を利用して、37.8℃、100%RHの条件で、面積1cm2に対する水分透過度を測定して、表2に示した。
前記実施例1及び比較例1〜比較例4で製造された粘接着フィルムをヘイズメーターHR−100(MURAKAMI COLOR RESEARCH LABORATORY製)を利用して透過率とヘイズを測定して、表2に示した。
前記実施例1及び比較例1〜比較例4で製造された粘接着フィルムを25mm×100mmのサイズで切断してガラスにラミネーティングした後、硬化させたフィルムを180゜で剥離する時の剥離力(peel strength)を測定した。引く速度は、300mm/minであり、各サンプル当たり2回ずつ測定した平均を求めて、下記表2に示した。
前記実施例1で製造された粘接着フィルムから離型PETフィルムを除去した後、1次でインキャップ用ガラス(上板)に合着し、残りの離型PETフィルムも除去した後、光照射の前に、真空合着器を利用して100mTorr未満の真空度で、70℃の熱と約2kgfの圧力を加えて上板とOLEDが形成された下板を合着した後、10J/cm2のUVを照射したことの以外は、実施例1と同一に実施した。
実施例1及び比較例5で製造された有機電子装置の有機発光素子の色座標を対比した結果、実施例1対比比較例5の有機発光素子の色座標が、5%以上変更されたことを確認することができた。また、実施例1対比高温高湿での寿命が、10%以上減少することを確認することができた。
前記コーティング溶液に水分吸着剤で金属酸化物(BaO)をアクリル系重合体100 重量部に対して、10重量部を追加で使用したことの以外の全ての過程は、前記実施例1と同一に実施した。
Claims (21)
- 上部に有機発光素子が形成されている基板と、前記基板上で前記有機発光素子の全面を封止する粘接着フィルムを含む有機電子装置であって、
前記粘接着フィルムは、常温で半固相であって、
架橋性官能基を側鎖に含み、且つアルキル(メタ)アクリレート及び架橋性官能基を有する共重合性単量体を重合された形態で含むアクリル系重合体、
アクリル系重合体100重量部に対して1重量部〜30重量部の量のエポキシ樹脂、架橋性官能基と反応できる架橋剤、及び
陽イオン光重合開始剤
を含む光硬化型粘接着剤組成物の光硬化物を含む粘接着層を含み、
前記粘接着層は、光照射の前には、105〜107Pa・sの粘度を有し、光照射の後には、106〜108Pa・s未満で粘度が上昇する
ことを特徴とする有機電子装置。 - 前記粘接着フィルムの光硬化及び熱硬化後の水分透過度が、150g/m2・day未満であることを特徴とする請求項1に記載の有機電子装置。
- 前記粘接着フィルムの粘接着層は、光照射の後に熱硬化が完了された状態で光硬化型粘接着剤組成物の未反応物を100ppm未満で含むことを特徴とする請求項1に記載の有機電子装置。
- 前記アクリル系重合体は、ガラス転移温度が、−60℃〜−10℃であり、重量平均分子量が、5万〜200万であることを特徴とする請求項1に記載の有機電子装置。
- 前記架橋性官能基は、グリシジル基、イソシアネート基、ヒドロキシ基、カルボキシル基、アミド基、エポキシド基、環状エーテル基、スルフィド基、アセタール基及びラクトン基から選択される一つ以上であることを特徴とする請求項1に記載の有機電子装置。
- 前記エポキシ樹脂は、多官能エポキシ樹脂、ビスフェノール系エポキシ樹脂、ノボラック型エポキシ樹脂、ナフタレン型エポキシ樹脂、トリスフェノールメタン型エポキシ樹脂、グリシジルアミン型エポキシ樹脂及び脂環族エポキシ樹脂からなる群より選択された1種以上であることを特徴とする請求項1に記載の有機電子装置。
- 前記陽イオン光重合開始剤は、芳香族ジアゾニウム塩、芳香族ヨードアルミニウム塩、芳香族スルホニウム塩または鉄−アレン錯体であることを特徴とする請求項1に記載の有機電子装置。
- 前記光硬化型粘接着剤組成物は、前記陽イオン光重合開始剤をアクリル系重合体100重量部に対して、0.01重量部〜10重量部で含むことを特徴とする請求項1に記載の有機電子装置。
- 前記架橋剤は、イソシアネート系化合物、エポキシ系化合物、アジリジン系化合物または金属キレート系化合物であることを特徴とする請求項1に記載の有機電子装置。
- 前記光硬化型粘接着剤組成物は、前記架橋剤をアクリル系重合体100重量部に対して、0.01重量部〜10重量部で含むことを特徴とする請求項1に記載の有機電子装置。
- 前記光硬化型粘接着剤組成物は、水分吸着剤をさらに含むことを特徴とする請求項1に記載の有機電子装置。
- 前記水分吸着剤は、アルミナ、金属酸化物、有機金属酸化物、金属塩または五酸化リンであることを特徴とする請求項11に記載の有機電子装置。
- 前記水分吸着剤は、 P2O5、Li2O、Na2O、BaO、CaO、MgO、Li2SO4、Na2SO4、CaSO4、MgSO4、CoSO4、Ga2(SO4)3、Ti(SO4)2、NiSO4、CaCl2、MgCl2、SrCl2、YCl3、CuCl2、CsF、TaF5、NbF5、LiBr、CaBr2、CeBr3、SeBr4、VBr3、MgBr2、BaI2、MgI2、Ba(ClO4)2及びMg(ClO4)2からなる群より選択される一つ以上であることを特徴とする請求項12に記載の有機電子装置。
- 前記光硬化型粘接着剤組成物は、フィラーをさらに含むことを特徴とする請求項1に記載の有機電子装置。
- 前記フィラーは、クレイ、タルク、シリカ、硫酸バリウム、水酸化アルミニウム、炭酸カルシウム、炭酸マグネシウム、ゼオライト、ジルコニア、チタニアまたはモンモリルロナイトからなる群より選択される一つ以上であることを特徴とする請求項14に記載の有機電子装置。
- 前記粘接着フィルム及び有機発光素子の間に前記有機発光素子を封止している保護層さらに含むことを特徴とする請求項1に記載の有機電子装置。
- アクリル系重合体、エポキシ樹脂及び陽イオン光重合開始剤を含む粘接着層を含む光硬化型粘接着フィルムを上板に合着し、粘接着層の全面に光を照射して光硬化させる段階と、
上部に有機発光素子が形成された下板に前記光硬化された粘接着層を前記有機発光素子の全面を覆うように合着する段階と、を含む
ことを特徴とする、請求項1に規定される有機電子装置の製造方法。 - 下板と粘接着層を合着した後、低温で熱硬化させる段階をさらに実行することを特徴とする請求項17に記載の有機電子装置の製造方法。
- 前記低温で熱硬化させる段階は、40℃〜80℃の温度で30分〜3時間の間実行することを特徴とする請求項18に記載の有機電子装置の製造方法。
- アクリル系重合体、エポキシ樹脂及び陽イオン光重合開始剤を含む
ことを特徴とする、請求項1に規定される有機電子装置の封止用光硬化型粘接着剤組成物。 - 請求項20に記載の組成物を含むフィルム上の成形物であって、光照射の前には、105〜107Pa・sの粘度を有し、光照射の後には、106〜108Pa・s未満で粘度が上昇することを特徴とする有機電子装置封止用光硬化型粘接着フィルム。
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