JP2020012048A - 紫外線硬化性樹脂組成物、有機el発光装置の製造方法及び有機el発光装置 - Google Patents
紫外線硬化性樹脂組成物、有機el発光装置の製造方法及び有機el発光装置 Download PDFInfo
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- JP2020012048A JP2020012048A JP2018134470A JP2018134470A JP2020012048A JP 2020012048 A JP2020012048 A JP 2020012048A JP 2018134470 A JP2018134470 A JP 2018134470A JP 2018134470 A JP2018134470 A JP 2018134470A JP 2020012048 A JP2020012048 A JP 2020012048A
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
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- 238000004381 surface treatment Methods 0.000 description 1
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- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
まず、有機EL発光装置の構造について説明する。有機EL発光装置1は、有機EL素子4と、有機EL素子4を覆う封止材5とを備える。封止材5は、有機EL素子4に直接接触した状態で有機EL素子4を覆ってもよく、封止材5と有機EL素子4との間に何らかの層が介在した状態で有機EL素子4を覆ってもよい。なお、ELとはエレクトロルミネッセンスの略である。また、有機EL素子4は、有機発光ダイオードとも呼ばれる。
紫外線硬化性樹脂組成物(以下、組成物(X)ともいう)について説明する。
組成物(X)を用いる封止材5の作製方法及び有機EL発光装置1の製造方法について説明する。
下記表の「組成」の欄に示す成分を混合することで、実施例及び比較例の組成物を調製した。
・SR247:二官能のアクリル化合物であるネオペンチルグリコールジアクリレート、ガラス転移温度117℃、粘度6mPa・s、サートマー社製、品番SR247。
・SR268:二官能のアクリル化合物であるテトラエチレングリコールジアクリレート、ガラス転移温度23℃、粘度20mPa・s、サートマー社製、品番SR268。
・A−BPE−10:二官能のアクリル化合物であるエトキシ化ビスフェノールAジアクリレート、ガラス転移温度−12℃、粘度550mPa・s、新中村化学工業社製、品番A−BPE−10。
・SR351S:三官能のアクリル化合物であるトリメチロールプロパントリアクリレート、ガラス転移温度62℃、粘度106mPa・s、サートマー社製。
・IBXA:イソボルニルアクリレート、ガラス転移温度97℃、粘度8mPa・s、大阪有機化学社製。
・FA−513AS:ジシクロペンタニル(メタ)アクリレート、ガラス転移温度120、粘度13mPa・s、日立化成社製、品番FA−513AS。
・Irgacure184:1−ヒドロキシ−シクロヘキシル−フェニル−ケトン、BASF社製、品名Irgacure184。
・IrgacureTPO:2,4,6−トリメチルベンゾイル−ジフェニル−フォスフィンオキサイド、BASF社製、品名IrgacureTPO。
(4−1)ゼオライト粒子1
ゼオライト粒子1は、下記の方法で製造され、そのD50は60nm、そのD90は110nm、そのpHは10である。
ゼオライト粒子2は、下記の方法で製造され、そのD50は150nm、そのD90は250nm、そのpHは10である。
ゼオライト粒子3は、表面処理が施されていない粉末品である東ソー製の品番ゼオラム4A、100メッシュパス品であり、そのD50は13μm、そのD90は30μm、そのpHは10である。
・CBB3098:吸着基としてカルボキシル基を有する側鎖末端型分散剤、酸価98mgKOH/g、粘度9000mP・s、重量平均分子量3000、綜研化学製、品番CBB3098。
・SOLSPERSE41000:吸着基としてリン酸基を有する液状の両末端型分散剤、酸価50mgKOH/g、粘度1500mP・s、重量平均分子量47000、ルーブリゾール社製、品番SOLSPERSE41000。
・SOLSPERSE32000:吸着基としてアミノ基とリン酸基とを有するワックス状の櫛型分散剤、アミン価31mgKOH/g、酸価15mgKOH/g、粘度14000mP・s、重量平均分子量3900、ルーブリゾール社製、品番SOLSPERSE32000。
・SOLSPERSE36000:吸着基としてリン酸基を有するワックス状の櫛型分型剤、酸価45mgKOH/g、粘度15000mP・s、重量平均分子量4100、ルーブリゾール社製、品番SOLSPERSE36000。
・DISPERBYK−2152:吸着基として保護基で保護されたリン酸基を有する超分岐型分散剤、酸価0mgKOH/g、粘度20000mP・s、重量平均分子量20000、ビックケミー社製、品番DISPERBYK−2152。
・DISPERBYK−111:吸着基としてリン酸基を有する液状の片末端型吸着剤、酸価129mgKOH/g、粘度900mP・s。
実施例及び比較例について、次の評価試験を実施した。その結果を表に示す。
組成物の粘度を、レオメータ(アントンパール・ジャパン社製、型番DHR−2)を使用して、温度25℃、せん断速度1000s-1の条件で測定した。
組成物を塗布して塗膜を作製し、この塗膜を、パナソニック電工株式会社製のLED−UV照射器(ピーク波長365nm)を用いて、約30mW/cm2の条件で20秒間紫外線照射して光硬化させることで、厚み10μmのフィルムを作製した。このフィルムの、JIS K7361−1による全光線透過率を測定した。
組成物の硬化物を加熱した場合のアウトガスをヘッドスペース法でサンプリングしてガスクロマトグラフにより測定した。ヘッドスペース用バイアルに組成物を100mg入れ、組成物に、パナソニック電工株式会社製のLED−UV照射器(ピーク波長365nm)を用いて紫外線を積算光量1500mJ/cm2の条件で照射して組成物を硬化させた後、バイアルを封止し、80℃で30分間加熱してから、バイアル中の気相部分をガスクロマトグラフに導入して分析した。その結果、発生したガスが300ppm以下であった場合を「A」、300ppmを超え500ppm未満であった場合を「B」、500ppm以上であった場合を「C」と評価した。
組成物をインクジェットプリンター(セイコーエプソン株式会社製、形式PX−B700)のカートリッジに入れ、インクジェットプリンターにおけるノズルからカートリッジ内の組成物を吐出しうることを確認してから、ノズルから組成物を吐出させてテストパターンを連続で印刷した。その結果、組成物を1時間吐出できるとともに吐出動作が安定していた場合を「A」、組成物を1時間吐出できたが吐出動作が断続的に不安定になった場合を「B」、吐出開始から1時間経過前にノズルが詰まって組成物を吐出できなくなった場合を「C」と、評価した。
石英ガラス片(寸法76mm×52mm×1mm)の表面上に、組成物を塗布して厚み50μmの塗膜を形成し、この塗膜の上に別の石英ガラス片(寸法76mm×52mm×1mm)を重ねた。続いて、塗膜を、パナソニック電工株式会社製のLED−UV照射器(ピーク波長365nm)を用いて、約30mW/cm2の条件で20秒間紫外線照射することで、硬化させた。次に、二つの石英ガラス片の間の密着強度を、JIS K6854に基づくT字ピール試験を行うことで、評価した。
組成物を窒素雰囲気下、40℃の温度で1か月間放置した。この試験の前の組成物の粘度と、試験の後の組成物の粘度とを、レオメータ(アントンパール・ジャパン社製、型番DHR−2)を使用して、温度25℃、せん断速度1000s-1の条件で測定し、その結果から、粘度の変化率を算出した。この変化率が5%未満である場合を「A」、5%以上10%未満である場合を「B」、10%以上である場合を「C」と評価した。
Claims (11)
- アクリル化合物(A)、
光重合開始剤(B)、
平均粒径200nm以下の吸湿剤(C)、及び
一分子中に二つ以上の吸着基を有する分散剤(D)を含有する、
紫外線硬化性樹脂組成物。 - 25℃における粘度が30mPa・s以下である、
請求項1に記載の紫外線硬化性樹脂組成物。 - 前記分散剤(D)の粘度が50000mPa・s以下である、
請求項1又は2に記載の紫外線硬化性樹脂組成物。 - 前記吸湿剤(C)に対する前記分散剤(D)の量は、40質量%以下である、
請求項1から3のいずれか一項に記載の紫外線硬化性樹脂組成物。 - 前記吸着基は、酸性の官能基と塩基性の官能基とからなる群から選択される少なくとも
一種の基を含む、
請求項1から4のいずれか一項に記載の紫外線硬化性樹脂組成物。 - 硬化物の光透過率が90%以上である、
請求項1から5のいずれか一項に記載の紫外線硬化性樹脂組成物。 - 有機EL素子封止用である、
請求項1から6のいずれか一項に記載の紫外線硬化性樹脂組成物。 - インクジェット法で成形される、
請求項1から7のいずれか一項に記載の紫外線硬化性樹脂組成物。 - 有機EL素子と前記有機EL素子を覆う封止材とを備える有機EL発光装置を製造する方法であり、
請求項1から8のいずれか一項に記載の紫外線硬化性樹脂組成物をインクジェット法で成形してから、前記紫外線硬化性樹脂組成物に紫外線を照射して硬化させることで前記封止材を作製することを含む、
有機EL発光装置の製造方法。 - 前記紫外線硬化性樹脂組成物を加熱してから前記紫外線硬化性樹脂組成物をインクジェット法で成形する、
請求項9に記載の有機EL発光装置の製造方法。 - 有機EL素子と、前記有機EL素子を覆う封止材とを備え、前記封止材は、請求項1から8のいずれか一項に記載の紫外線硬化性樹脂組成物の硬化物である、
有機EL発光装置。
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