JP2011190454A - 緑色発光化合物及びこれを発光材料として採用している光発光素子 - Google Patents
緑色発光化合物及びこれを発光材料として採用している光発光素子 Download PDFInfo
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Abstract
【解決手段】下式1又は式2で表される有機発光化合物とその製造方法、及びアノードとカソードに介在される発光領域として、前記式1及び式2の化合物から選択される一つ以上と、アントラセン誘導体、ベンズ[a]アントラセン誘導体、及びナフタセン誘導体から選択される一つ以上とを含むことを特徴とする有機電界EL素子に関するものである。[式1]
[式2]
【選択図】なし
Description
[化学式1]
[化学式2]
[化学式1]
[化学式2]
上記化学式1または化学式2のR1及びR2は、各々独立に2つ以上の芳香族環が縮合された縮合多環芳香族環であり、R3乃至R6は、各々独立に芳香族環であって、前記R1乃至R6の各芳香族環は、C1〜C20のアルキル基、C1〜C20のアルコキシ基、ハロゲン基、C5〜C7のシクロアルキル基がさらに置換され得る。
[化学式3]
[化学式4]
2,6−ジクロロアントラキノン1.0g(3.6mmol)とジフェニルアミン1.3g(7.7mmol)を無水トルエン50mLに溶かした後、パラジウムアセテート(Pd(OAc)2)2.4g(24.4mmol)、トリフェニルホスフィン0.2mL(1.9mmol)とナトリウムt−ブトキシド(t-BuONa)0.93g(9.7mmol)を添加して、110℃で3日間還流させた。反応終了後、蒸留水10mLを添加して30分間攪拌した。生成された固体をろ過して、アセトン及びTHFなどで洗浄した後乾燥させて、塩化メチレンで再結晶し、ビス(2,6−ジフェニルアミノ)アントラキノン1.1g(2.0mmol、収率56%)を収得した。
1H NMR(200MHz, CDCl3):δ 6.46(d, 8H), 6.65-6.75(m, 8H), 7.0(m, 8H), 7.3(m, 4H), 7.5-7.6(m, 4H), 7.65-7.8(m, 6H), 7.9(s, 2H)
MS/FAB: 764(found), 764.98(calculated)
N−フェニル−2−ナフチルアミン1.7g(7.8mmol)を利用して、製造例1と同一な方法により化合物2 0.53g(0.61mmol、収率17%)を収得した。
1H NMR(200MHz, CDCl3):δ 6.45(d, 4H), 6.6(t, 2H), 6.75-6.8(m, 8H), 7.0-7.15(m, 6H), 7.2-7.3(m, 6H), 7.45-7.6(m, 10H), 7.65-7.8(m, 6H), 7.9(s, 2H)
MS/FAB: 864(found), 865.10(calculated)
N−フェニル−1−ナフチルアミン1.7g(7.8mmol)を利用して、製造例1と同一な方法により化合物3 0.41g(0.47mmol、収率13%)を収得した。
1H NMR(200MHz, CDCl3):δ 6.45(d, 4H), 6.5(d, 2H), 6.6(t, 2H), 6.75-6.8(m, 4H), 7.0-7.05(m, 4H), 7.15-7.2(m, 4H), 7.3-7.35(m, 8H), 7.55-7.8(m, 14H), 7.9(s, 2H)
MS/FAB: 864(found), 865.10(calculated)
ジ(2−ナフチル)アミン2.1g(7.8mmol)を利用して、製造例1と同一な方法により化合物4 0.52g(0.54mmol、収率15%)を収得した。
1H NMR(200MHz, CDCl3):δ 6.75-6.8(m, 12H), 7.0-7.1(m, 4H), 7.2-7.35(m, 8H), 7.45-7.6(m, 16H), 7.65-7.8(m, 6H), 7.9(s, 2H)
MS/FAB: 964(found), 965.22(calculated)
3−メトキシフェニルアミン1.53g(7.7mmol)を利用して、製造例1と同一な方法により化合物5 1.0g(1.21mmol、収率34%)を収得した。
1H NMR(200MHz, CDCl3):δ 3.75(s, 6H), 5.95-6.05(m, 4H), 6.15(d, 2H), 6.45(d, 4H), 6.6(t, 2H), 6.75-7.05(m, 10H), 7.3(m, 4H), 7.5-7.55(m, 4H), 7.65-7.8(m, 6H), 7.9(s, 2H)
MS/FAB: 824(found), 825.03(calculated)
N−m−トリル−2−ナフチルアミン1.8g(7.7mmol)を利用して、製造例1と同一な方法により化合物6 0.61g(0.68mmol、収率19%)を収得した。
1H NMR(200MHz, CDCl3):δ 2.3(s, 6H), 6.25-6.30(t, 4H), 6.4(d, 2H), 6.75-6.9(m, 10H), 7.1(m, 2H), 7.2-7.3(m, 6H), 7.4-7.55(m, 10H), 7.65-7.8(m, 6H), 7.9(s, 2H)
MS/FAB: 892(found), 893.15(calculated)
N−m−トリル−1−ナフチルアミン1.8g(7.7mmol)を利用して、製造例1と同一な方法により化合物7 0.38g(0.43mmol、収率12%)を収得した。
1H NMR(200MHz, CDCl3):δ 2.3(s, 6H), 6.25-6.3(t, 4H), 6.4-6.5(m, 4H), 6.75-6.9(m, 6H), 7.15(t, 4H), 7.3(m, 8H), 7.5-7.8(m, 14H), 7.9(s, 2H)
MS/FAB: 892(found), 893.15(calculated)
製造例2で得られたビス(2,6−ジフェニルアミノ)アントラキノン1.16g(1.8mmol)に1−ブロモフルオランテン1.1g(3.9mmol)を利用して、製造例1と同一な方法により化合物8 0.77g(0.76mmol、収率21%)を収得した。
1H NMR(200MHz, CDCl3):δ 6.4(d, 4H), 6.6(t, 2H), 6.75-6.8(m, 8H), 7.0-7.1(m, 6H), 7.2-7.3(m, 10H), 7.45-7.6(m, 10H), 7.7-7.8(m, 4H), 7.9-7.95(m, 4H)
MS: 1012(found), 1013.27(calculated)
2,7−ジクロロアントラキノン0.5g(1.8mmol)とジフェニルアミン0.65g(3.9mmol)を利用して、製造例1と同一な方法によりビス(2,7−ジフェニル)アントラキノン0.60g(1.1mmol、収率61%)を収得した。このように得られたビス(2,7−ジフェニル)アントラキノン0.60g(1.1mmol)を利用して、製造例1と同一な方法により化合物9 0.40g(0.52mmol、収率29%)を収得した。
1H NMR(200MHz, CDCl3):δ 6.4(d, 8H), 6.6(t, 4H), 6.75-6.8(m, 4H), 7.0(m, 8H), 7.3(m, 4H), 7.5-7.55(m, 4H), 7.65-7.8(m, 6H), 7.9(s, 2H)
MS: 764(found), 764.98(calculated)
N−フェニル−2−ナフチルアミン0.85g(3.9mmol)を利用して、製造例9と同一な方法により化合物10 0.29g(0.34mmol、収率19%)を収得した。
1H NMR(200MHz, CDCl3):δ 6.4(d, 4H), 6.6(t, 2H), 6.75-6.8(m, 8H), 7.0-7.1(m, 6H), 7.2-7.3(m, 6H), 7.45-7.6(m, 10H), 7.65-7.8(m, 6H), 7.9(s, 2H)
MS: 864(found), 865.10(calculated)
ジ(2−アントリル)アミン2.8g(7.6mmol)を利用して、製造例1と同一な方法により化合物11 0.29g(0.25mmol、収率7%)を収得した。
1H NMR(200MHz, CDCl3):δ 6.75-6.8(m, 12H), 7.25-7.3(m, 12H), 7.45-7.6(m, 16H), 7.65-7.8(m, 14H), 7.9(s, 2H)
MS/FAB: 1164(found), 1165.46(calculated)
本発明の発光材料を利用した構造のOLED素子を製作した。
まず、OLED用ガラス(三星−コーニング社製)から得られた透明電極ITO薄膜(15Ω/□)を、トリクロロエチレン、アセトン、エタノール、蒸留水を順に使用して超音波洗浄を施した後、イソプロパノールに入れて保管した後使用した。
実施例1と同一な方法により正孔注入層、正孔伝達層を形成させた後、前記真空蒸着装備内の他のセルに発光ホスト材料であるtris(8-hydroxyquinoline)- aluminum(III)(Alq)を入れて、また他のセルには下記構造のクマリン 545T(C545T)をそれぞれ入れた後、二つの物質を異なる速度で蒸発させてドーピングすることにより、前記正孔伝達層上に30nm厚の発光層を蒸着した。この時のドーピング濃度は、Alq基準2〜5mol%が好ましい。
実施例1と同一な方法により正孔注入層、正孔伝達層を形成させた後、前記真空蒸着装備内の他のセルに発光ホスト材料であるDNPBAを入れて、また他のセルには化合物Gをそれぞれ入れた後、二つの物質を異なる速度で蒸発させてDNPBA基準2〜5mol%でドーピングすることにより、前記正孔伝達層上に30nm厚の発光層を蒸着した。
実施例1と比較例1で製造された本発明による有機発光化合物と従来の発光化合物を含有するOLED素子の発光効率をそれぞれ5,000cd/m2及び20,000cd/m2で測定し、表1に示した。特に、緑色発光材料の場合、高輝度領域における発光特性が非常に重要であるため、これを反映するために、20,000cd/m2程度の高輝度データを添付した。
実施例1と同一な方法により正孔注入層、正孔伝達層を形成させた後、前記真空蒸着装備内の他のセルに発光ホスト材料である化合物18(または、化合物19、または化合物23、または化合物24、または化合物25)を入れて、また他のセルには化合物1(または化合物5、または化合物13)をそれぞれ入れた後、二つの物質を異なる速度で蒸発させてドーピングすることにより、前記正孔伝達層上に30nm厚の発光層を蒸着した。この時のドーピング濃度は、発光ホスト材料基準に2〜5mol%が好ましい。
Claims (4)
- 下記の化学式1または化学式2で表される有機発光化合物。
[化学式1]
[化学式2]
(前記化学式1または化学式2のR1及びR2は各々独立に、アントリル、フルオランテニル、ピレニル、フルオレニル及びペリレニル基から選択され、R3乃至R6は各々独立に、フェニル、ナフチル、アントリル、フェナントリル、フルオレニル、フルオランテニル、ピレニル、ペリレニル、ナフタセニル及びビフェニル基から選択され、前記R1及びR2のアントリル、フルオランテニル、ピレニル、フルオレニルまたはペリレニル基、及びR3乃至R6のフェニル、ナフチル、アントリル、フェナントリル、フルオレニル、フルオランテニル、ピレニル、ペリレニル、ナフタセニルまたはビフェニル基はそれぞれ、C1〜C20のアルキル基、C1〜C20のアルコキシ基がさらに置換され得る。) - 前記化学式1または化学式2のR1乃至R2は各々独立に、2‐アントリル、2‐フルオランテニル、1‐ピレニル、2‐フルオレニル及び3‐ペリレニル基から選択されることを特徴とする、請求項1に記載の有機発光化合物。
- 前記R1及びR2のアントリル、フルオランテニル、ピレニル、フルオレニルまたはペリレニル基、及びR3乃至R6のフェニル、ナフチル、アントリル、フェナントリル、フルオレニル、フルオランテニル、ピレニル、ペリレニル、ナフタセニルまたはビフェニル基はそれぞれ、メチル、t‐ブチルまたはメトキシ基がさらに置換されることを特徴とする、請求項2に記載の有機発光化合物。
- 下記構造を有することを特徴とする、請求項3に記載の有機発光化合物。
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- 2006-08-14 US US11/990,502 patent/US20090128010A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
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KR20070021043A (ko) | 2007-02-22 |
EP1922382A1 (en) | 2008-05-21 |
EP1922382A4 (en) | 2010-08-25 |
JP4969575B2 (ja) | 2012-07-04 |
CN101243157A (zh) | 2008-08-13 |
WO2007021117A1 (en) | 2007-02-22 |
CN101243157B (zh) | 2012-09-05 |
KR100788254B1 (ko) | 2007-12-27 |
US20090128010A1 (en) | 2009-05-21 |
JP2009504730A (ja) | 2009-02-05 |
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