JP2009221181A - 縮合環芳香族化合物及びこれを用いた有機発光素子 - Google Patents
縮合環芳香族化合物及びこれを用いた有機発光素子 Download PDFInfo
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Abstract
Description
一般式[1]で示される縮合芳香族化合物は、例えば、下記の合成ルート1に示すように、ジブロモクリセン誘導体とボロン酸の誘導体を原料に合成することができるが、これに限定されるものではない。
また、一般式[2]で示される縮合芳香族化合物は、例えば、下記の合成ルート2に示すように、ジブロモクリセン誘導体を原料に合成することもできる。
1.発光層内での電子・ホールの輸送。
2.ホストの励起子生成。
3.ホスト分子間の励起エネルギー伝達。
4.ホストからゲストへの励起エネルギー移動。
300mlのナスフラスコに以下に示す試薬、溶媒を仕込んだ。
化合物1−1:5.0g(13.0mmol)
アセト酢酸エチル:6.74g(51.8mmol)
リン酸三カリウム:16.5g(77.7mmol)
酢酸パラジウム(II):116mg(0.52mmol)
2−(ジターシャルブチルフォスフィノ)−2’−メチルビフェニル:324mg(1.04mmol)
トルエン:100ml
エタノール:15ml
ナスフラスコに以下に示す試薬、溶媒等を仕込んだ。
化合物1−2:3.76g(89.6mmol)
ジオキサン:30ml
水酸化リチウム・一水和物:3.76g(89.6mmol)
ナスフラスコに以下に示す試薬、溶媒等を仕込んだ。
化合物1−3:2.87g(6.36mmol)
塩化チオニル:50ml
ジメチルホルムアミド:300μl
ナスフラスコに以下に示す試薬、溶媒等を仕込んだ。
化合物1−5:1.2g(3.89mmol)
ベンゼンセレン酸無水物:4.4g(8.56mmol)
クロロベンゼン:60ml
ナスフラスコに以下に示す試薬、溶媒を仕込んだ。
化合物1−6:37mg(0.0046mmol)
化合物1−7:40mg(0.0092mmol)
エタノール:2ml
トルエン:0.4ml
6N−水酸化カリウム:300μl
ナスフラスコに以下に示す試薬、溶媒を仕込んだ。
化合物1−8:55mg(0.0485mmol)
ベンゼンジアゾニウム−2−カルボキシレートハイドロクロリド:500mg(0.27mmol)
プロピレンオキシド:0.5ml
ジクロロエタン:5ml
MALDI−TOF−MAS(マトリックス支援イオン化−飛行時間型質量分析)によりM+が1229.79であることを確認し、例示化合物H−6を同定した。
NMR測定によりこの化合物の構造を確認した。
溶液状態における例示化合物H−6の発光スペクトルを測定した。発光スペクトルの測定にあたり、予め分光光度計U−3010(日立分光製)を使用して、例示化合物H−6のトルエン溶液(1×10-5mol/l)の吸収スペクトルを測定した。吸収スペクトルを測定した後、分光蛍光光度計F−4500(日立分光製)を使用して、例示化合物H−6のトルエン溶液(1×10-5mol/l)の発光スペクトル(PLスペクトル)を測定した。このとき、吸収スペクトル測定の結果から励起波長を351nmとした。測定の結果、図6に示すPLスペクトルが得られた。図6に示すPLスペクトルより、例示化合物H−6の最大発光波長の第1ピーク、第2ピークはそれぞれ469nm、502nmであり良好な青色発光を示すことがわかった。
ナスフラスコに以下に示す試薬、溶媒を仕込んだ。
化合物1−6:0.76g(2.26mmol)
化合物1−9:0.8g(3.80mmol)
エタノール:18ml
トルエン:2ml
6N−水酸化カリウム:800ml
ナスフラスコに以下に示す試薬、溶媒を仕込んだ。
化合物1−10:76mg(0.111mmol)
ベンゼンジアゾニウム−2−カルボキシレートハイドロクロリド:82mg(0.444mmol)
プロピレンオキシド:0.2ml
ジクロロエタン:4ml
MALDI−TOF−MAS(マトリックス支援イオン化−飛行時間型質量分析)によりM+が780.04であることを確認し、例示化合物H−1を同定した。
NMR測定によりこの化合物の構造を確認した。
1H−NMR(CDCl3,400MHz) σ(ppm):7.81(t,6H,J=2.8Hz),7.73−7.65(m,18H),7.60−7.58(m,4H),7.43−7.38(m,6H),7.54(d,2H,J=6.8Hz),1.42(s,36H),1.40(s,36H)
本実施例では、図3で示される有機発光素子を作製した。まずガラス基板(基板1)上に膜厚100nmで酸化錫インジウム(ITO)(陽極2)をパターニングしてITO電極付きガラス基板を作製した。次に、このITO電極付きガラス基板上に、有機化合物からなる層と陰極を抵抗加熱による真空蒸着で連続製膜した。具体的には、まずホール輸送層5として、下記に示す化合物2を膜厚20nmで製膜した。次に発光層3として、ホストである下記に示される化合物3とゲストである例示化合物H−1を、化合物3に対して例示化合物H−1の含有量が1重量%となるように共蒸着した。このとき発光層3の膜厚は30nmとした。次に電子輸送層として、下記に示す化合物4を膜厚30nmで製膜した。次にKFを膜厚1nmで製膜し、最後にAlを膜厚100nmで製膜した。ここでKF及びAlは、陰極4として機能する。
2 陽極
3 発光層
4 陰極
5 ホール輸送層
6 電子輸送層
7 ホール注入層
8 ホール/エキシトンブロッキング層
10,20,30,40,50 有機発光素子
Claims (4)
- 陽極と陰極と、
該陽極と該陰極との間に挟持される有機化合物層と、から構成され、
該陽極及び該陰極のいずれかが透明か半透明であり、
該有機化合物層に請求項1又は2に記載の縮合環芳香族化合物が少なくとも一種類含まれることを特徴とする、有機発光素子。 - 前記縮合環芳香族化合物が含まれる層が発光層であることを特徴とする、請求項3に記載の有機発光素子。
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JP2011231086A (ja) * | 2010-04-30 | 2011-11-17 | Canon Inc | 新規有機化合物およびそれを有する有機発光素子 |
JPWO2010018842A1 (ja) * | 2008-08-12 | 2012-01-26 | 出光興産株式会社 | ベンゾフルオランテン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
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- 2008-03-27 US US12/301,434 patent/US7919197B2/en active Active
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- 2008-03-27 RU RU2009140295/04A patent/RU2422425C1/ru not_active IP Right Cessation
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US8940413B2 (en) | 2009-04-23 | 2015-01-27 | Canon Kabushiki Kaisha | Organic compound having acenaphtho[1,2-k]benzo[e]acephenanthrene derivative, light-emitting device, and image display apparatus |
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JP2012246258A (ja) * | 2011-05-30 | 2012-12-13 | Canon Inc | 縮合多環化合物及びこれを用いた有機発光素子 |
Also Published As
Publication number | Publication date |
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KR20090122919A (ko) | 2009-12-01 |
EP2132157A4 (en) | 2012-08-08 |
RU2422425C1 (ru) | 2011-06-27 |
EP2132157B1 (en) | 2017-02-01 |
EP2132157A1 (en) | 2009-12-16 |
BRPI0806570A2 (pt) | 2014-05-06 |
WO2008120806A1 (en) | 2008-10-09 |
JP5252960B2 (ja) | 2013-07-31 |
US20090184630A1 (en) | 2009-07-23 |
RU2009140295A (ru) | 2011-05-10 |
US20110140595A1 (en) | 2011-06-16 |
US7919197B2 (en) | 2011-04-05 |
KR101143789B1 (ko) | 2012-05-11 |
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