JPWO2016132640A1 - 有機発光素子用インク組成物及び有機発光素子 - Google Patents
有機発光素子用インク組成物及び有機発光素子 Download PDFInfo
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- JPWO2016132640A1 JPWO2016132640A1 JP2017500297A JP2017500297A JPWO2016132640A1 JP WO2016132640 A1 JPWO2016132640 A1 JP WO2016132640A1 JP 2017500297 A JP2017500297 A JP 2017500297A JP 2017500297 A JP2017500297 A JP 2017500297A JP WO2016132640 A1 JPWO2016132640 A1 JP WO2016132640A1
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- Prior art keywords
- light emitting
- organic light
- binder resin
- emitting device
- ink composition
- Prior art date
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Abstract
Description
本形態に係る有機発光素子用インク組成物は、発光材料、スチレン系モノマーを必須成分とした上記した様な特定重合体を含むバインダー樹脂、および溶媒を含有するものである。本発明の有機発光素子用インク組成物は、発光材料を含むことから、原則として、有機発光素子の発光層の形成に使用される。
発光材料は、発光層において、正孔および電子を利用して行う発光に直接または間接に寄与する機能を有する。なお、本明細書において、「発光」には、蛍光による発光および燐光による発光を含むものとする。
ホスト材料は、通常、発光層に注入された正孔および電子を輸送する機能を有する。
ドーパント材料は、輸送された正孔および電子を再結合することにより得られるエネルギーを利用して発光する機能を有する。
本発明におけるバインダー樹脂は、多角度レーザー光散乱検出器を用いたゲル浸透クロマトグラフィから求められる重量平均絶対分子量が20万〜80万の範囲内にあり、かつ慣性半径から求められる分岐度が0.20〜0.55の範囲内にある、スチレン系モノマーを必須成分とするモノビニル化合物と、エチレン性不飽和二重結合を2以上含有する多官能ビニル化合物との多分岐共重合体を含むバインダー樹脂である。この多分岐共重合体としては、好適には後記する溶媒に可溶性のものが用いられる。
本発明の有機発光素子用インク組成物の調製には溶媒が用いられる。溶媒としては、好適には、多分岐共重合体を含有するバインダー樹脂を溶解できるものを用いる。この溶媒は、特に制限されず、公知のものが使用されうる。具体的には、芳香族系溶媒、アルカン系溶媒、エーテル系溶媒、アルコール系溶媒、エステル系溶媒、アミド系溶媒、他の溶媒等が挙げられる。
本発明の一実施形態において、有機発光素子用インク組成物の製造方法は、特に制限されないが、(1)バインダー樹脂および溶媒を含む溶液または分散液を調製し、次いで、当該溶液または分散液に発光材料を添加する方法、(2)発光材料および溶媒を含む溶液または分散液を調製し、次いで、当該溶液または分散液にバインダー樹脂を添加する方法、(3)バインダー樹脂および溶媒を含む溶液または分散液と、発光材料および溶媒を含む溶液または分散液とをそれぞれ調製し、これらの溶液または分散液を混合する方法等が挙げられる。
本発明の一形態によれば、陽極、発光層、および陰極を含む有機発光素子が提供される。なお、前記有機発光素子は、正孔注入層、正孔輸送層、電子輸送層、および電子注入層等の他の層を1以上含んでいてもよい。また、封止部材の公知のものを含んでいてもよい。以下、各構成について詳細に説明する。
陽極としては、特に制限されないが、金(Au)等の金属、ヨウ化銅(CuI)、インジウムスズ酸化物(ITO)、酸化スズ(SnO2)、酸化亜鉛(ZnO)等が用いられうる。これらの材料は、単独で用いても、2種以上を組み合わせて用いてもよい。
正孔注入層は、有機発光素子において任意の構成要素であり、陽極から正孔を取り入れる機能を有する。通常、陽極から取り入れた正孔は、正孔輸送層または発光層に輸送される。
正孔輸送層は、有機発光素子において任意の構成要素であり、正孔を効率に輸送する機能を有する。また、正孔輸送層は、正孔の輸送を防止する機能を有しうる。正孔輸送層は、通常、陽極または正孔注入層から正孔を取り入れ、発光層に正孔を輸送する。
発光層は、発光層に注入された正孔および電子の再結合により生じるエネルギーを利用して発光を生じさせる機能を有する。
電子輸送層は、有機発光素子において任意の構成要素であり、電子を効率に輸送する機能を有する。また、電子輸送層は、電子の輸送を防止する機能を有しうる。電子輸送層は、通常、陰極または電子注入層から電子を取り入れ、発光層に電子を輸送する。
電子注入層は、有機発光素子において任意の構成要素であり、陰極から電子を取り入れる機能を有する。通常、陰極から取り入れた電子は、電子輸送層または発光層に輸送される。
陰極としては、特に制限されないが、リチウム、ナトリウム、マグネシウム、アルミニウム、ナトリウム−カリウム合金、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、希土類金属等が挙げられる。これらの材料は、単独で用いても、2種以上を組み合わせて用いてもよい。
エチレン性不飽和二重結合を2以上含有する高分子量多官能ビニル化合物の調製例
攪拌機、温度計、滴下ロート及びコンデンサーを備えた2リットルフラスコに、室温下、エトキシ化ペンタエリスリトール(5モル−エチレンオキシド付加ペンタエリスリトール)50.5g、BF3ジエチルエーテル溶液(50%)1gを加え、110℃に加熱した。これに3−エチル−3−(ヒドロキシメチル)オキセタン450gを、反応による発熱を制御しつつ、25分間でゆっくり加えた。発熱が収まったところで、反応混合物をさらに120℃で3時間撹拌し、その後、室温に冷却した。得られた多分岐ポリエーテルポリオールの重量平均分子量は3,000、水酸基価は530であった(分岐剤1)。
エチレン性不飽和二重結合を2以上含有する高分子量多官能ビニル化合物の調製例
7%酸素導入管、温度計、コンデンサーを備えたディーンスタークデカンター、および攪拌機を備えた反応容器に、多分岐ポリエステルポリオール「Boltorn H20」10g、ジブチル錫オキシド1.25g、官能基としてイソプロペニル基を有するメチルメタクリレート100g、およびヒドロキノン0.05gを加え、混合溶液中に3ml/分の速度で7%酸素を吹き込みながら、撹拌下に加熱した。デカンターへの留出液量が1時間あたり15〜20gになるように加熱量を調節し、1時間ごとにデカンター内の留出液を取り出し、これに相当する量のメチルメタクリレートを加えながら6時間反応させた。
反応終了後、メチルメタクリレートを減圧下で留去し、残っているヒドロキシ基をキャッピングするために無水酢酸10g、スルファミン酸2gを加えて室温下、10時間撹拌した。濾過でスルファミン酸を除去し、減圧下で無水酢酸および酢酸を留去した後に、残留物を酢酸エチル70gに溶解し、ヒドロキノンを除去する為に5%水酸化ナトリウム水溶液20gで4回洗浄した。さらに7%硫酸水溶液20gで2回、水20gで2回洗浄した。得られた有機層にメトキノン0.0045gを加え、減圧下、7%酸素を導入しながら溶媒を留去し、イソプロペニル基およびアセチル基を有する多分岐ポリエステル12gを得た。得られた多分岐ポリエステルの質量平均分子量は2860、数平均分子量は3770であり、多分岐ポリエステルポリオールへのイソプロペニル基およびアセチル基導入率は、それぞれ55%および40%であった(エチレン性不飽和二重結合を2以上含有する高分子量多官能ビニル化合物2)。
スチレンモノマー 90部、上記調製例1で得られた高分子量多官能ビニル化合物1をスチレンモノマーに対して700ppm、トルエン10部からなる混合溶液を調製し、更に、有機過酸化物としてt−ブチルパーオキシベンゾエートをスチレンモノマーに対して200ppm加え、110〜160℃にて段階的に昇温させながら、未反応スチレンモノマーが実質的に検出されなくなるまで溶液重合させ、多分岐共重合体を含むバインダー樹脂1を得た。
上記調製例1で得られた高分子量多官能ビニル化合物1を、同量の調製例2で得られた高分子量多官能ビニル化合物2に代え、スチレンモノマーに対して500ppmにした以外は、上記合成例1と同様にして多分岐共重合体を含むバインダー樹脂2を得た。
スチレンモノマー 85部、アクリル酸ブチル5部、上記調製例1で得られた高分子量多官能ビニル化合物1をモノマー比(スチレンモノマーとアクリル酸ブチル合計量に対して)300ppm、トルエン10部からなる混合溶液に代えた以外は、上記合成例1と同様にして多分岐共重合体を含むバインダー樹脂3を得た。
スチレンモノマー 90部、トルエン10部からなる混合溶液、過酸化物を無添加に代えた以外は上記合成例1と同様にして直鎖共重合体を含むバインダー樹脂4を得た。
上記各合成例及び比較合成例の各バインダー樹脂不揮発分につき、GPC−MALS測定を、Shodex HPLC、検出器Wyatt Technology DAWN EOS、Shodex RI−101、カラムShodex KF−806L×2、溶媒THF、流量1.0ml/minの条件にて行った。また、GPC−MALLSの測定の解析は、Wyatt社の解析ソフトASTRAにより行い、各バインダー樹脂について重量平均絶対分子量を求めた他、GPC−MALLSから求められる該バインダー樹脂の分子量を横軸(X軸)、慣性半径を縦軸(Y軸)とした両対数グラフにおける分子量25万〜1000万の領域での傾き(当該分子量範囲で得られた直線状の部分のみの測定値を元に、前記ソフトにて自動計算される近似直線の傾き)から分岐度を求めた。
[実施例1]
0.01gのトリス[2−(p−トリル)ピリジン]イリジウム(Ir(mppy)3)(Lumtec社製)と、0.09gの9,9’−(p−tert−ブチルフェニル)−1,3−ビスカルバゾールH−1(DIC株式会社製)とを、9gのテトラリンに混合して加熱溶解させた。得られた溶液を室温まで冷却し、合成例1で調製したバインダー樹脂1不揮発分を0.03g添加した。次いで、全重量が10gとなるようにテトラリンをさらに添加して、十分に撹拌した。最後に、0.45μmフィルターであるマイショリディスク(東ソー株式会社製)を用いて異物を除去し、有機発光素子用IJインク組成物1を製造した。
合成例1で調製したバインダー樹脂1不揮発分を、同量の合成例2で調製したバインダー樹脂2不揮発分とした以外は、実施例1と同様にして有機発光素子用IJインク組成物2を製造した。
合成例1で調製したバインダー樹脂1不揮発分を、同量の合成例3で調製したバインダー樹脂3不揮発分とした以外は、実施例1と同様にして有機発光素子用IJインク組成物3を製造した。
合成例1で調製したバインダー樹脂1不揮発分を、同量の比較合成例で調製したバインダー樹脂不揮発分とした以外は、実施例1と同様にして有機発光素子用IJインク組成物4を製造した。
上記実施例1〜3および比較例1で製造した各有機発光素子用IJインク組成物について各種評価を行った。
上記で調製した各有機発光素子用IJインク組成物を、ピエゾ方式ノズルをヘッドに有するインクジェットプリンター(プリンタヘッドは、Nova PH 256/80 AAA Print head)により、被印刷基材としてガラス基板上に吐出を行い、下記評価基準にて、安定的に吐出可能であるか否か確認した。
○:シングルドロップかつサテライトありである
△:ダブルドロップかつサテライトなしである
×:ダブルドロップかつサテライトありである
インジウムスズ酸化物(ITO)基板上に、0.1μLの有機発光素子用IJインク組成物を滴下し、25℃、1Torrで減圧乾燥した。得られた有機薄膜の凸部および凹部の差(凹凸差)を、光干渉表面形状計測装置(株式会社菱化システム製)を用いて測定し、以下の基準に従って評価した。なお、前記凸部とは有機薄膜表面のうち水平面を基準として最も高いものを意味し、前記凹部とは有機薄膜表面のうち水平面を基準として最も低いものを意味する。
○:凹凸差が50nm超100nm以下である
△:凹凸差が100nm超150nm以下である
×:凹凸差が150超である
有機発光素子に対し、外部電源に接続して10mAの電流を流し、有機発光素子からの発光をBM−9(株式会社トプコン製)にて測光した。この際、電流値から10mA/cm2のときの発光効率を算出し、以下の基準に従って評価した。
○:発光効率が20cd/A以上25cd/A未満
△:発光効率が20cd/A未満
Claims (7)
- 発光材料と、多角度レーザー光散乱検出器を用いたゲル浸透クロマトグラフィから求められる重量平均絶対分子量が20万〜80万の範囲内にあり、かつ慣性半径から求められる分岐度が0.20〜0.55の範囲内にある、スチレン系モノマーを必須成分とするモノビニル化合物と、エチレン性不飽和二重結合を2以上含有する多官能ビニル化合物との多分岐共重合体を含むバインダー樹脂と、溶媒とを含有することを特徴とする有機発光素子用インク組成物。
- エチレン性不飽和二重結合を2以上含有する多官能ビニル化合物が、重量平均分子量1000〜15000の、エチレン性不飽和二重結合を2以上含有する多官能ビニル化合物である請求項1記載の有機発光素子用インク組成物。
- バインダー樹脂が、更に、スチレン系モノマーを必須成分とするモノビニル化合物の直鎖共重合体を含有する請求項1記載の有機発光素子用インク組成物。
- バインダー樹脂が、質量基準で、スチレン系モノマーを必須成分とするモノビニル化合物100部当たり、エチレン性不飽和二重結合を2以上含有する多官能ビニル化合物0.01〜1部を用いて重合してなる、スチレン系モノマーを必須成分とするモノビニル化合物と、エチレン性不飽和二重結合を2以上含有する多官能ビニル化合物との多分岐共重合体と、スチレン系モノマーを必須成分とするモノビニル化合物の直鎖共重合体とを含有するバインダー樹脂である請求項1記載の有機発光素子用インク組成物。
- 前記発光材料が、芳香環構造を含有する低分子発光材料である請求項1記載の有機発光素子用インク組成物。
- 陽極、発光層、及び陰極を含み、前記発光層が、
発光材料と、多角度レーザー光散乱検出器を用いたゲル浸透クロマトグラフィから求められる重量平均絶対分子量が20万〜80万の範囲内にあり、かつ慣性半径から求められる分岐度が0.20〜0.55の範囲内にある、スチレン系モノマーを必須成分とするモノビニル化合物と、エチレン性不飽和二重結合を2以上含有する多官能ビニル化合物との多分岐共重合体とを含むバインダー樹脂を含有してなる有機発光素子。 - 質量換算で、発光材料100部当たり前記バインダー樹脂不揮発分10〜1000部を含有してなる請求項6記載の有機発光素子。
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