JP5074423B2 - 接着性封入用組成物フィルム及び有機エレクトロルミネッセンスデバイス - Google Patents
接着性封入用組成物フィルム及び有機エレクトロルミネッセンスデバイス Download PDFInfo
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- JP5074423B2 JP5074423B2 JP2008551473A JP2008551473A JP5074423B2 JP 5074423 B2 JP5074423 B2 JP 5074423B2 JP 2008551473 A JP2008551473 A JP 2008551473A JP 2008551473 A JP2008551473 A JP 2008551473A JP 5074423 B2 JP5074423 B2 JP 5074423B2
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
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- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
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- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
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- 239000010451 perlite Substances 0.000 description 1
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- MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 description 1
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- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 239000008117 stearic acid Substances 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
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- 150000003505 terpenes Chemical class 0.000 description 1
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- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
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- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C09J123/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
- C09J123/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefines
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- C09J7/00—Adhesives in the form of films or foils
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- C09J7/00—Adhesives in the form of films or foils
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- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
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- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
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- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
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- C09J2423/00—Presence of polyolefin
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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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
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- Electroluminescent Light Sources (AREA)
- Sealing Material Composition (AREA)
- Laminated Bodies (AREA)
- Adhesive Tapes (AREA)
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Description
本出願は2006年1月24日に出願された日本特許出願番号2006−15334の優先権を主張し、かかる出願の開示はその全体を参照することにより本明細書に組み込まれる。
電子機器で使用される、接着性能を有する封入用(encapsulating)組成物又は封止用(sealing)組成物が開示される。より詳細には、有機エレクトロルミネッセンス素子のような表示装置の封入剤として用いられる接着性封入用組成物及び封入用フィルムが開示される。
Y+X−である。Yは、アリールジアルキルスルホニウム、アルキルジアリールスルホニウム、トリアリールスルホニウム、ジアリールヨードニウム及びテトラアリールホスホニウムカチオン類であり、各アルキル基及びアリール基は置換されていても良い。XはPF6 −、SbF6 −、CF3SO3 −、(CF3SO2)2N−、(CF3SO2)3C−、(C6F5)4B−アニオン類。
−MXmYn (I)
(式中、MはBのような2価以上の金属原子、又はP=Oであり、Xは水素或いは置換された又は非置換のアルキル基、アルケニル基又はアルコキシ基であり、Yは置換された又は非置換のアルコキシ基、シロキシ基、又はカルボキシル基、或いはジケトレートであり、mは1〜3であり、nは0〜2である。
15部のポリイソブチレン樹脂(BASF社(BASF AG)のオパノール(OPANOL)B100、粘度平均分子量は1,110,000g/モル)、及び10部の水素添加石油樹脂(出光興産(Idemitsu Kosan Co., Ltd.)のIMARVP−100、軟化点:100℃)をトルエンに溶解して15重量%の樹脂溶液を調製した。得られた樹脂溶液を厚さ38μmの放出処理されたPETフィルム上にコーティングし、100℃のオーブンで20分間乾燥した。感圧性接着剤を含む得られたフィルムを、厚さ25μmの放出処理されたPET(ポリエチレンテレフタレート)フィルム上に積層し、感圧性接着シートを製造した。このようにして、50μmの厚さの感圧性接着を有する透明なフィルム(接着性封入用フィルム)を得た。得られた封入用フィルムの特性を、以下の手順にしたがって、接着性試験、水分透過性測定、及び可視光透過性によって評価した。
封入用フィルム(50mm(長さ)×20mm(幅))を1枚のアルミホイル(100mm(長さ)×20mm(幅)×0.05mm(厚さ)、住軽アルミニウムホイル社(Sumikei Aluminum-Foil Co., Ltd.)製、パーツ番号:「SA50」)の末端部に積層した。得られた積層体をガラスプレート(76mm(長さ)×26mm(幅)×1.2mm(厚さ)、松浪ガラス工業(Matsunami Glass Ind., Ltd.)製、商標名:「マイクロ−スライドグラス(Micro-Slide Glass)S−7224」)の上にさらに積層した。得られた積層体は、フィルムがアルミニウムホイルの長さに沿って90°で剥離された場合の剥離力(接着力)の測定を受けた。引張速度は100/分であった。各サンプルごとに2回ずつ測定を行い、それぞれの測定の剥離力の平均値を決定した。下記の表2に示されるように、接着力は16N/25mmであった。
上記の方法で製造した厚さ100μmの封入用フィルムを測定サンプルとして使用した。水分透過性の測定はJISZ0204に準拠したカップ法で実施した。測定条件は、60℃、相対湿度90%(一定温度一定湿度の容器を使用した)、及び測定時間は24時間であった。下記の表2に示されるように、水分透過性は11g/m2.24時間であり、低値であることが明らかとなった。
上記の方法で製造された厚さ50μmの封止用フィルムを測定サンプルとして使用した。透過性の測定は、分光分析装置、パーツ番号「U−4199」(日立(Hitachi)製)を使用して実施された。380nm〜800nmの波長領域での透過性の平均値を測定すると、下記の表2に示されるように、90%以上の高透過性を示した。これにより、光を透過させる間この封入用フィルムを使用できることが明らかになった。
接着性封入用フィルムを実施例1に記載の方法を用いて製造したが、これら実施例では下記の表1に示されるように樹脂成分を変更した(表1の値は重量%である)。これらの実施例で使用した樹脂成分の詳細は次のとおりである。
ポリマー2:ポリイソブチレン(オパノール(OPANOL)B100、BASF社(BASF AG)、Mv=4,000,000g/モル)
化合物1:水素添加C5〜C9炭化水素樹脂(IMARV P−100、出光興産(Idemitsu Kosan Co., Ltd.)、軟化点:100℃)
化合物2:水素添加C5〜C9炭化水素樹脂(IMARV P−140、出光興産(Idemitsu Kosan Co., Ltd.)、軟化点:140℃)
化合物3:水素添加脂環式炭化水素樹脂(エスコレッツ(ESCOREZ)5380、エクソン・モービル社(Exxon Mobil Co.,Ltd.)、軟化点:85℃)
化合物4:水素添加脂環式炭化水素樹脂(エスコレッツ(ESCOREZ)5300、エクソン・モービル社(Exxon Mobil Co., Ltd.)、軟化点:105℃)
化合物5:水素添加脂環式炭化水素樹脂(エスコレッツ(ESCOREZ)5340、エクソン・モービル社(Exxon Mobil Co., Ltd.)、軟化点:137℃)
化合物6:水素添加脂環式炭化水素樹脂(エスコレッツ(ESCOREZ)5400、エクソン・モービル社(Exxon Mobil Co., Ltd.)、軟化点:102℃)
化合物7:水素添加テルベン樹脂(クリアロン(CLEARON)P85、ヤスハラケミカル社(Yasuhara Chemical)、軟化点:125℃)
化合物8:水素添加テルベン樹脂(クリアロン(CLEARON)P125、ヤスハラケミカル社(Yasuhara Chemical)、軟化点:125℃)
化合物9:水素添加芳香族改質炭化水素樹脂(エスコレッツ(ESCOREZ)5600、エクソン・モービル社(Exxon Mobil Co.,Ltd.)、軟化点:102℃)
化合物10:水素添加C5〜C9炭化水素樹脂(IMARV S100、出光興産(Idemitsu Kosan Co., Ltd.)、軟化点:100℃)
化合物11:水素添加芳香族改質テルベン樹脂(クリアロン(CLEARON)K4090、ヤスハラケミカル社(Yasuhara Chemical)、軟化点:90℃)
化合物12:ポリイソブチレン(グリソパル(GLISSOPAL)V1500、BASF社(BASF AG)、Mv=2,500)
化合物13:ポリイソブチレン(テトラックス(TETRAX 3T)3T、新日本石油化学(Nippon Petrochemicals Co., Ltd.)、Mv=30,000)
封入用フィルムの特性試験
本明細書に得た封入用フィルムの特性を評価するため、接着試験、水分透過性の測定、及び可視光線透過性の測定を、実施例1に記載の手順にしたがって実施した。それらの結果を下記の表2に示す。
封入用フィルムの調製に市販のエポキシ樹脂接着剤XNR5516HV(ナガセケムテックス社(Nagase ChemteX Corp.)製)を使用した以外は実施例1に記載の手順を繰り返した。製造元のデータによると、接着剤は粘度370Paの光硬化型液状接着剤であり、吸水率は1%、硬化後のTgは100℃以上、及び曲げたときに亀裂を示す。この接着剤に充填剤を添加するので、フィルムは透明性のない白色であり、光が接着剤を通って放射される上部発光構造で使用することができない。さらに、水分透過性は16g/m2/24時間であり、実施例1〜15と比較すると弱い。また、フィルムは6,000mJ/cm2の紫外線照射で硬化するので、硬化後の温度は1時間の間80℃を維持し、素子は光又は熱によって明らかにダメージを受け、長い硬化時間により生産性が悪くなる。
この実施例では、図4に示される層構造を有する有機EL素子10が製造された。ガラス基板として、ITO(インジウム酸化スズ)フィルム2(三容真空工業社(Sanyo Vacuum Industries Co., Ltd.)製、ITOフィルム厚さ:150nm、シート抵抗:<14Ω/スクエア、ガラス厚さ:0.7mm、外形寸法:40mm×40mm)を有するガラス基板1を準備した。ITOフィルム2はフォトリソグラフィーによってパターニングし、基盤の上にITO電極パターン2を形成した。
40gのポリイソブチレン樹脂(BASF社(BASF AG)、オパノール(OPANOL)B100、Mv=400000)、50gの水素添加炭化水素樹脂(エクソン・モービル社(Exxon Mobil Co., Ltd.)、軟化点:137℃)、10gの紫外線硬化型アクリレート樹脂(新中村化学工業(Shin-Nakamura Chemical Industry, Co., Ltd.)A−DCP)、及び1gの光重合開始剤(チバ・スペシャリティー・ケミカルズ社(Ciba Specialty Chemicals, Co., Ltd.)、イルガキュア(IRGACURE)184)をトルエンに溶解し、実施例17として25重量パーセント固体の溶液を得た。この溶液を、シリコーン処理をしたPETフィルム(帝人−デュポン社(Teijin-DuPont Co., Ltd.)A31 38μm)(以下PET1と言う)にナイフコータを使用してコーティングした。次に、これを100℃で30分間乾燥し、続いて別のシリコーン処理をしたPETフィルム(帝人−デュポン社(Teijin-DuPont Co., Ltd.)A71 38μm)(以下PET2と言う)に積層した。接着層の厚さは50μmであった。実施例18〜21は表3の構成要素を用いて同様に調製した。
実施例22は、70gのポリイソブチレン(BASF社(BASF AG)、オパノール(OPANOL)B50、Mv=400,000)、及び30gの水素添加炭化水素樹脂(エスコレッツ(ESCOREZ)5340、エクソン・モービル社(Exxon Mobil Co., Ltd.)、軟化点:137℃)をトルエンに溶解して調製し、25重量%溶液を調製した。この溶液を使用して上記の実施例17〜21で説明した接着層を生成した。
P4:ポリマー3−ポリイソブチレン(オパノール(OPANOL)B50、BASF社(BASF AG)、Mv=400,000)
C14:化合物14−トリーシクロデカンジ−メタノールジアクリレート(A−DCP、新中村化学工業(Shin-Nakamura Chemical Industry, Co., Ltd.))
C15:化合物15−水素添加イソプレンジアクリレート(スパイダ(SPIDA-S)−S、大阪有機化学工業(Osaka Organic Chemical Industry, Co., Ltd.))
C16:化合物16−二酸化リモネン(アトフィナ・ケミカルズ(ATOFINA Chemicals))
C17:化合物17−水素添加脂環式炭化水素樹脂(エスコレッツ(ESCOREZ)5340、エクソン・モービル社(Exxon Mobil Co., Ltd.)、軟化点:137℃)
C18:化合物18−光ラジカル重合開始剤(イルガキュア(IRGACURE)184、チバ・スペシャリティー・ケミカルズ社(Ciba Specialty Chemicals, Co., Ltd.))
C19:化合物19−光カチオン重合開始剤(WPI113、和光純薬工業(Wako Chemical Co., Ltd.))
接着試験
上記で得た接着性フィルムの20mm×50mmの部分を切断し、PET1を除去した。次に、面(PET2で裏打ちされていない接着性フィルムの表面)を、100mm×20mmのシリカ蒸着したPETフィルム(三菱樹脂(Mitsubishi Plastics Co., Ltd.)、テクバリア(Techbarrier)H、12μm)に積層し、次にPET2を除去して76mm×26mmのガラスプレート(松浪硝子工業(Matsunami Glass Co., Ltd.)、厚さ1.2mm、S−7213)に積層した。次に、接着性フィルムをガラスプレートを通して紫外線照射(フュージョンUVシステムズジャパン社(Fusion UV systems Japan Co., Ltd.)製F300S(Hバルブ))を用いて50mJで20回硬化した。引張試験機(Tensilon machine)(東洋ボールドウィン社(Toyo Baldwin Co., Ltd.)、RTM−100)を用いて20℃で20mm/分で90°剥離試験を行なった。剥離データは90°で2回の剥離強度の平均として報告される。
上記のようにして得た100μmの接着性フィルムを紫外線照射(フュージョンUVシステムズジャパン社(Fusion UV systems Japan Co., Ltd.)製、F300S(Hバルブ))を用いて、50mJで20回硬化した。水分透過性をキャプ方式(Cap Method)を用いてJIS Z0208に準拠して測定した。温度は60℃、相対湿度は90%であった。水分透過性データの報告は2回の測定の平均である(表4)。
サンプルの透明性を分光分析装置U4100(日立(Hitachi Ltd.))で測定した。上記のように作製した厚さ50μmのフィルムを使用した。表4は、波長領域400nm〜800nmにおける平均の透明性を示している。
上で作製した接着性フィルムの25mm×25mmの部分を切断し、PET1を除去した。次に面を130mm×25mmのシリカ蒸着したPETフィルム(三菱樹脂(Mitsubishi Plastics Co., Ltd.)、テクバリア(Techbarrier)H、12μm)に積層した。上で適用したPET2を除去し、この面を76mm×26mmのガラスプレート(松浪硝子工業(Matsunami Glass Co., Ltd.)、厚さ1.2mm、S−7213)に積層した。接着性フィルムを、次にガラスプレートを通して紫外線照射(フュージョンUVシステムズジャパン社(Fusion UV systems Japan Co., Ltd.)製F300S(Hバルブ))を用いて50mJで20回硬化した。1kgの鉛のおもりをシリカ蒸着したPETフィルムの末端部につけ、25℃で24時間後の接着性フィルムの伸長を保持力として測定した。表4で報告されている保持力は3回の測定の平均である。
PP:ポリプロピレンプレート
Al:アルミホイル
Claims (3)
- 電子機器で使用する接着性封入用組成物であって、
水素添加環状オレフィン系ポリマー、及び
ポリイソブチレン樹脂、を含む接着性封入用組成物。 - 封入用フィルムであって、
請求項1記載の前記接着性封入用組成物を含む接着性フィルム、及び
前記接着性フィルムに設けられる裏材、を具備する封入用フィルム。 - 有機エレクトロルミネッセンスELデバイスであって、
一対の対向する電極、
前記電極の間に配置される少なくとも有機発光層を有する発光ユニット、及び
前記発光ユニットに、前記発光ユニットの上部に、又は前記発光ユニットの周囲に配置される、請求項1記載の前記接着性封入用組成物を含む接着性フィルム、を具備する、有機エレクトロルミネッセンスELデバイス。
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- 2007-01-23 WO PCT/US2007/001724 patent/WO2007087281A1/en active Application Filing
- 2007-01-23 CN CN2007800029900A patent/CN101370889B/zh not_active Expired - Fee Related
- 2007-01-23 JP JP2008551473A patent/JP5074423B2/ja not_active Expired - Fee Related
- 2007-01-23 EP EP07716918A patent/EP1976952A4/en not_active Withdrawn
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JP5667281B1 (ja) * | 2013-12-27 | 2015-02-12 | 古河電気工業株式会社 | 有機電界発光素子用充填材料及び有機電界発光素子の封止方法 |
JP5667282B1 (ja) * | 2013-12-27 | 2015-02-12 | 古河電気工業株式会社 | 有機電界発光素子用充填材料及び有機電界発光素子の封止方法 |
WO2015098692A1 (ja) * | 2013-12-27 | 2015-07-02 | 古河電気工業株式会社 | 有機電界発光素子用充填材料及び有機電界発光素子の封止方法 |
WO2015098691A1 (ja) * | 2013-12-27 | 2015-07-02 | 古河電気工業株式会社 | 有機電界発光素子用充填材料及び有機電界発光素子の封止方法 |
US9793511B2 (en) | 2013-12-27 | 2017-10-17 | Furukawa Electric Co., Ltd. | Filler material for organic electroluminescent element and method of sealing organic electroluminescent element |
US10084153B2 (en) | 2013-12-27 | 2018-09-25 | Furukawa Electric Co., Ltd. | Filler material for organic electroluminescent element and method of sealing organic electroluminiscent element |
Also Published As
Publication number | Publication date |
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CN101370889B (zh) | 2012-02-29 |
EP1976952A1 (en) | 2008-10-08 |
KR20080088606A (ko) | 2008-10-02 |
JP2007197517A (ja) | 2007-08-09 |
KR101422856B1 (ko) | 2014-07-24 |
US20090026934A1 (en) | 2009-01-29 |
CN101370889A (zh) | 2009-02-18 |
WO2007087281A1 (en) | 2007-08-02 |
JP2009524705A (ja) | 2009-07-02 |
EP1976952A4 (en) | 2010-01-13 |
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