JP4674454B2 - 有機発光材料および有機電界発光素子 - Google Patents
有機発光材料および有機電界発光素子 Download PDFInfo
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- JP4674454B2 JP4674454B2 JP2004280869A JP2004280869A JP4674454B2 JP 4674454 B2 JP4674454 B2 JP 4674454B2 JP 2004280869 A JP2004280869 A JP 2004280869A JP 2004280869 A JP2004280869 A JP 2004280869A JP 4674454 B2 JP4674454 B2 JP 4674454B2
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Images
Description
上述した一般式(1)で示される本発明の有機発光材料は、有機電界発光素子の有機層に用いられるビフルオランテン化合物である。ビフルオランテン化合物は、各々のフルオランテンの結合位置において複数の異性体が存在するが、本発明の有機発光材料はその構造異性体を全て包含する。すなわち、本発明の有機発光材料は、ビフルオランテンの分子対称性を鑑みた、以下の15通りの組み合わせの置換様式の異性体を全て含む(下記表1参照)。
b)2、2’結合;一般式(1)のA4部位とA5部位での結合[構造式(2)]
c)3、3’結合;一般式(1)のA14部位とA15部位での結合[構造式(1)]
d)7、7’結合;一般式(1)のA2部位とA7部位での結合[構造式(7)]
e)8、8’結合;一般式(1)のA1部位とA8部位での結合[構造式(8)]
f)1、2’結合;一般式(1)のA3部位とA5部位での結合[構造式(5)]
g)1、3’結合;一般式(1)のA3部位とA13部位での結合[構造式(4)]
h)1、7’結合;一般式(1)のA3部位とA7部位での結合[構造式(13)]
i)1、8’結合;一般式(1)のA3部位とA8部位での結合[構造式(14)]
j)2、3’結合;一般式(1)のA4部位とA13部位での結合[構造式(3)]
k)2、7’結合;一般式(1)のA4部位とA7部位での結合[構造式(11)]
l)2、8’結合;一般式(1)のA4部位とA8部位での結合[構造式(12)]
m)3、7’結合;一般式(1)のA15部位とA7部位での結合[構造式(9)]
n)3、8’結合;一般式(1)のA15部位とA8部位での結合[構造式(10)]
o)7、8’結合;一般式(1)のA2部位とA8部位での結合[構造式(15)]
a)ハロゲン化されたフルオランテンを、マグネシウムを用いたグリニヤー反応によってカップリングさせる合成方法。
b)ハロゲン化されたフルオランテンを、銅触媒存在下でウルマン反応によってカップリングさせる方法。
c)ボロン酸、もしくはボロン酸エステル化されたフルオランテンとハロゲン化されたフルオランテンとを、パラジウムに代表される遷移金属触媒によってカップリングさせる(いわゆる鈴木カップリング反応)によって合成させる方法。
a)有機発光材料を合成した後、速やかに冷所に静置させる。その保管温度は−100℃から100℃の範囲が好ましく、より好ましくは−50℃から50℃の温度範囲で保管させる。
b)有機発光材料を合成した後、速やかに遮光性を有する容器に保管する。
c)有機発光材料を合成した後、合成した有機発光材料を窒素、二酸化炭素、アルゴンなどの不活性ガス雰囲気下で保管する。
次に、上述した有機発光材料を用いた有機電界発光素子(有機EL素子)の構成を、図1に基づいて詳細に説明する。
次のようにして、表1の構造式(2)で示した2、2’―ビフルオランテンを得た。すなわち、合成例1の合成経路および合成において、3−ブロモフルオランテン(C1)を2−ブロモフルオランテンに変更した以外は、合成例1と全く同様に操作を実施し、白色固体12.1gを得た。得られた固体を1H−NMR、13C−NMR、およびFD−MSにて測定した結果、目的物である2、2’―ビフルオランテン[表1構造式(2)]であることを確認した。
次のようにして、表1の構造式(8)で示した8、8’―ビフルオランテンを得た。すなわち、合成例1の合成経路および合成において、3−ブロモフルオランテン(C1)を8−ブロモフルオランテンに変更した以外は、合成例1と全く同様に操作を実施し、白色固体14.1gを得た。得られた固体を1H−NMR、13C−NMR、およびFD−MSにて測定した結果、目的物である8、8’―ビフルオランテン[表1構造式(8)]であることを確認した。
合成例1によって得られた3、3’―ビフルオランテン[表1の構造式(1)]を用い、以下のように有機電界発光素子(図2参照)を作製した。
図2の発光層14cの有機材料として、下記表6に記載した各構造式の化合物をした使用した以外は、実施例1と全く同様に有機電界発光素子を作製し、同様の評価を行った。尚、下記表6には、評価結果も合わせて示した。
図2の発光層14cの有機材料として、下記構造式(19)に示す3−フェニルフルオランテン(特開平10−189248号公報参照)を使用した以外は、実施例1と全く同様に有機電界発光素子を作成し同じく評価を行った。その結果を合わせて上記表6に示した。
図2の発光層14cの有機材料として、下記構造式(20)に示す3−(ナフタレン1−イル)フルオランテンを使用した以外は、実施例1と全く同様に有機電界発光素子を作成し同じく評価を行った。その結果を合わせて上記表6に示した。
図2の発光層14cとして、下記構造式(21)に示される9、10−ジ(2−ナフチル)アントラセン(ADN)を蒸着し、膜厚50nmの膜を形成した。その際、ADNには合成例2で製造された2、2’―ビフルオランテン[表1の構造式(2)]を相対膜厚比で5%ドーピングして発光層14cとした。
実施例6記載におけるADNに対する2、2’―ビフルオランテン[表1の構造式(2)]のドーピング濃度を、上記表7記載の各濃度に変更した以外は、実施例6と同様な素子構成として評価を行った。その結果を合わせて上記表7に示した。
Claims (6)
- 下記一般式(1)で示されるフルオランテンを二量化したビフルオランテン構造を有する有機電界発光素子用の有機発光材料。
- 請求項1記載の有機発光材料において、
前記一般式(1)中のA1〜A20のうちの一つ以上が、アルキル基、アルケニル基、アルコキシ基、複素環基もしくはアリール基から選ばれる置換基で置換されている有機発光材料。 - 陽極と陰極との間に有機層を狭持してなる有機電界発光素子において、
前記有機層が、下記一般式(1)で示されるフルオランテンを二量化したビフルオランテン構造を有する有機発光材料を用いて構成されている有機電界発光素子。
- 請求項3記載の有機電界発光素子において、
前記一般式(1)中のA1〜A20のうちの一つ以上が、アルキル基、アルケニル基、アルコキシ基、複素環基もしくはアリール基から選ばれる置換基で置換されている有機電界発光素子。 - 請求項3記載の有機電界発光素子において、
前記有機層が、前記一般式(1)に示される有機発光材料を用いて構成された発光層を備えている有機電界発光素子。 - 請求項5記載の有機電界発光素子において、
前記発光層に、前記一般式(1)に示される有機発光材料が20体積%以下の割合で含まれている有機電界発光素子。
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JP4618414B2 (ja) * | 2004-02-24 | 2011-01-26 | ソニー株式会社 | 有機材料および有機電界発光素子 |
WO2006095539A1 (ja) | 2005-02-21 | 2006-09-14 | Mitsubishi Chemical Corporation | 有機電界発光素子及びその製造 |
US9214636B2 (en) * | 2006-02-28 | 2015-12-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
JP4819655B2 (ja) * | 2006-04-27 | 2011-11-24 | キヤノン株式会社 | 4−アリールフルオレン化合物及びそれを用いた有機発光素子 |
JP4818159B2 (ja) | 2006-04-27 | 2011-11-16 | キヤノン株式会社 | フルオランテン誘導体およびそれを有する有機発光素子 |
JP5084208B2 (ja) * | 2006-09-15 | 2012-11-28 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び有機エレクトロルミネッセンス素子用材料 |
US8076009B2 (en) | 2007-10-26 | 2011-12-13 | Global Oled Technology, Llc. | OLED device with fluoranthene electron transport materials |
US8129039B2 (en) | 2007-10-26 | 2012-03-06 | Global Oled Technology, Llc | Phosphorescent OLED device with certain fluoranthene host |
US8420229B2 (en) | 2007-10-26 | 2013-04-16 | Global OLED Technologies LLC | OLED device with certain fluoranthene light-emitting dopants |
US8431242B2 (en) | 2007-10-26 | 2013-04-30 | Global Oled Technology, Llc. | OLED device with certain fluoranthene host |
US8088500B2 (en) | 2008-11-12 | 2012-01-03 | Global Oled Technology Llc | OLED device with fluoranthene electron injection materials |
JP2017123352A (ja) * | 2014-03-31 | 2017-07-13 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子および電子機器 |
KR20180016328A (ko) * | 2015-06-16 | 2018-02-14 | 이데미쓰 고산 가부시키가이샤 | 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자 및 전자 기기 |
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JPH10189248A (ja) * | 1996-11-07 | 1998-07-21 | Mitsui Chem Inc | 有機電界発光素子 |
JP2001244075A (ja) * | 2000-02-29 | 2001-09-07 | Mitsui Chemicals Inc | 炭化水素化合物および有機電界発光素子 |
JP2001257074A (ja) * | 2000-03-10 | 2001-09-21 | Mitsui Chemicals Inc | 炭化水素化合物および有機電界発光素子 |
JP2003105332A (ja) * | 2001-09-28 | 2003-04-09 | Canon Inc | 有機発光素子 |
JP2007507449A (ja) * | 2003-09-29 | 2007-03-29 | ビーエーエスエフ アクチェンゲゼルシャフト | ディールスアルダー反応によるフェニル置換フルオランテンの合成及びその使用 |
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JPH10189248A (ja) * | 1996-11-07 | 1998-07-21 | Mitsui Chem Inc | 有機電界発光素子 |
JP2001244075A (ja) * | 2000-02-29 | 2001-09-07 | Mitsui Chemicals Inc | 炭化水素化合物および有機電界発光素子 |
JP2001257074A (ja) * | 2000-03-10 | 2001-09-21 | Mitsui Chemicals Inc | 炭化水素化合物および有機電界発光素子 |
JP2003105332A (ja) * | 2001-09-28 | 2003-04-09 | Canon Inc | 有機発光素子 |
JP2007507449A (ja) * | 2003-09-29 | 2007-03-29 | ビーエーエスエフ アクチェンゲゼルシャフト | ディールスアルダー反応によるフェニル置換フルオランテンの合成及びその使用 |
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