JP4653061B2 - アミン化合物および有機発光素子および青色有機発光素子 - Google Patents
アミン化合物および有機発光素子および青色有機発光素子 Download PDFInfo
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- JP4653061B2 JP4653061B2 JP2006312927A JP2006312927A JP4653061B2 JP 4653061 B2 JP4653061 B2 JP 4653061B2 JP 2006312927 A JP2006312927 A JP 2006312927A JP 2006312927 A JP2006312927 A JP 2006312927A JP 4653061 B2 JP4653061 B2 JP 4653061B2
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- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Description
そして、蛍光性化合物または燐光性化合物の励起子を生成させ、この励起子が基底状態にもどる際に放射される光利用する素子である。
アミノ化合物の有機発光素子材料および有機発光素子の例としては、特許文献1にジアミノ縮合芳香環誘導体を用いた有機発光素子が開示されている。また他の例として、特許文献2、特許文献3には、ジアミノフルオレン誘導体を用いた有機発光素子が開示されている。また他の例として、特許文献4や特許文献5には、ジアミノ化合物を用いた有機発光素子が開示されている。さらに他の例として、特許文献6には中心のビフェニレン基がオルト置換タイプのクォーターフェニレン誘導体であるジアミノ化合物を用いた有機発光素子が開示されている。
(1)下記一般式[1]で示されることを特徴とするアミン化合物である。
上記一般式[1]における置換基の具体例を以下に示す。
本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に狭持された一または複数の有機化合物を含む層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が一般式[1]で示される化合物の少なくとも一種を含有する。
図1は、本発明の有機発光素子の一例を示す断面図である。図1は、基板1上に、陽極2、発光層3及び陰極4を順次設けた構成のものである。ここで使用する発光素子は、それ自体でホール輸送能、エレクトロン輸送能及び発光性の性能を単一で有している場合や、それぞれの特性を有する化合物を混ぜて使う場合に有用である。
(電子親和力)=(イオン化ポテンシャル)−(バンドギャップ)
バンドギャップの測定は、例えば、有機化合物をガラス上に50nm程度の厚みに蒸着し、この蒸着膜の吸収スペクトルを測定し、その吸収端の波長Y(nm)をX(eV)に換算して求められる。
換算式はX=1240/Yで求められる。
例示化合物C−5の合成
a)中間体化合物の合成
(化合物[1−1]は、
N−(9,9−Dimethyl−fluorene−2−yl)−N−phenyl−amineと3−Bromoiodobenzeneを原料として用いUllmann反応により製造できる。
例示化合物B−2の合成
例示化合物D−2の合成
例示化合物E−5の合成
例示化合物E−1の合成
図3に示す構造の有機発光素子を以下に示す方法で作成した。
化合物3−1(イオン化ポテンシャル:5.31eV,電子親和力:2.39eV、バンドギャップ:2.92eV)
更に電子輸送層6としてバソフェナントロリン(BPhen)を真空蒸着法にて40nmの膜厚に形成した。蒸着時の真空度は1.0×10−4Pa、成膜速度は0.2〜0.3nm/secの条件であった。
<実施例7−10>
例示化合物C−5に代えて、例示化合物B−2,D−2,E−5,E−1を用いた他は実施例6と同様に素子を作成し評価を行った。(結果は一覧として表1に示す。)
<比較例1>
例示化合物C−5に代えて、下記に示す比較化合物4−1を用いた他は実施例1と同様に素子を作成し、同様な評価を行った。5.0Vの印加電圧で、発光輝度1800cd/m2、458nm青色の発光が観測された。さらに、窒素雰囲気下で電流密度を30mA/cm2に保ち100時間電圧を印加したところ、初期輝度1250cd/m2から100時間後、500cd/m2となった。(結果は一覧として表1に示す。)
実施例6−10及び比較例1の検討結果のまとめ一覧を以下の表1に示す。
B:電子親和力の絶対値
C:A−B(バンドギャップの値)
D:2.72(発光層ホストとして用いた化合物2−1の電子親和力の絶対値)−B
E:C−2.95(発光層ホストとして用いた化合物2−1のバンドギャップの値)
F:印加電圧5Vにおける初期輝度(cd/m2)
G:電流密度を30mA/cm2に保ち、初期の発光輝度を1とした場合の100時間後の発光輝度をパーセンテージで表した値
H:○・・・Fが2700以上且つGが70以上
△・・・Fが2100以上で2700未満且つGが50以上70未満
×・・・Fが2100未満且つGが50未満
図4に示す構造の有機発光素子を以下に示す方法で作成した。
基板1としてのガラス基板上に、陽極2としての酸化錫インジウム(ITO)をスパッタ法にて120nmの膜厚で成膜したものを透明導電性支持基板として用いた。これをアセトン、イソプロピルアルコール(IPA)で順次超音波洗浄し、次いでIPAで煮沸洗浄後乾燥した。さらに、UV/オゾン洗浄したものを透明導電性支持基板として使用した。
実施例11と同様に正孔注入層には化合物5−1を用い、正孔輸送層には例示化合物C−5に代えて、例示化合物B−2,D−2,E−5,E−1を用いた他は実施例11と同様に素子を作成し、同様な評価を行った。(結果は一覧として表3に示す。)
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
Claims (4)
- 陽極および陰極からなる一対の電極と前記一対の電極の間に配置された有機化合物層とを有する有機発光素子において、
前記有機化合物層は請求項1または2のいずれか一項に記載のアミン化合物を有することを特徴とする有機発光素子。 - 陽極および陰極からなる一対の電極と前記一対の電極の間に配置された発光層とを有する有機発光素子において、
前記陽極と前記発光層の間に配置された正孔輸送層をさらに有し、
前記正孔輸送層は請求項1または2のいずれか一項に記載のアミン化合物を有することを特徴とする有機発光素子。
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JP2006312927A JP4653061B2 (ja) | 2005-12-20 | 2006-11-20 | アミン化合物および有機発光素子および青色有機発光素子 |
CN2006800208323A CN101193851B (zh) | 2005-12-20 | 2006-12-13 | 胺化合物、有机发光器件和有机发蓝光器件 |
US11/912,621 US20090091244A1 (en) | 2005-12-20 | 2006-12-13 | Amine compound, organic light-emitting device, and organic blue-light-emitting device |
EP06834988.5A EP1966123B1 (en) | 2005-12-20 | 2006-12-13 | Amine compound, organic light-emitting device, and organic blue-light-emitting device |
PCT/JP2006/325318 WO2007072838A1 (en) | 2005-12-20 | 2006-12-13 | Amine compound, organic light-emitting device, and organic blue-light-emitting device |
KR1020087017390A KR101036399B1 (ko) | 2005-12-20 | 2006-12-13 | 아민 화합물, 유기발광소자 및 청색 유기발광소자 |
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JP5277588B2 (ja) * | 2007-08-21 | 2013-08-28 | 東ソー株式会社 | 有機el素子 |
TW200935639A (en) | 2007-11-28 | 2009-08-16 | Fuji Electric Holdings | Organic EL device |
EP2225204B1 (en) * | 2007-12-03 | 2014-04-23 | Semiconductor Energy Laboratory Co, Ltd. | Carbazole derivative, and light-emitting element, light-emitting device, and electronic device using carbazole derivative |
KR101050459B1 (ko) * | 2008-09-03 | 2011-07-20 | 삼성모바일디스플레이주식회사 | 플루오렌 화합물 및 이를 이용한 유기 전계 발광 장치 |
EP2415752B1 (en) * | 2009-03-19 | 2016-03-09 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent element using same |
JP5476034B2 (ja) * | 2009-04-27 | 2014-04-23 | ケミプロ化成株式会社 | 新規なトリアリールアミン化合物、それよりなるホール輸送材料およびそれを用いた有機エレクトロルミネッセンス素子 |
US8860013B2 (en) * | 2009-11-27 | 2014-10-14 | Sharp Kabushiki Kaisha | Organic electroluminescence element, manufacturing method thereof, and organic electroluminescence display device |
EP2511969A4 (en) * | 2009-12-11 | 2014-03-19 | Mitsubishi Chem Corp | ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC ELECTROLUMINESCENT SCREEN, AND ORGANIC ELECTROLUMINESCENT LIGHTING |
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EP2740165B1 (de) * | 2011-08-03 | 2018-11-07 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
KR102104855B1 (ko) * | 2012-07-23 | 2020-04-27 | 메르크 파텐트 게엠베하 | 2-디아릴아미노플루오렌의 유도체 및 이를 함유하는 유기 전자 화합물 |
KR102006621B1 (ko) | 2012-07-23 | 2019-08-02 | 메르크 파텐트 게엠베하 | 화합물 및 유기 전계 발광 디바이스 |
JP6444046B2 (ja) | 2013-04-03 | 2018-12-26 | キヤノン株式会社 | 有機化合物及び有機発光素子 |
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WO2016076384A1 (ja) * | 2014-11-14 | 2016-05-19 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
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JP7493931B2 (ja) * | 2019-12-12 | 2024-06-03 | JDI Design and Development 合同会社 | 有機el素子、有機el表示パネル、および、有機el素子の製造方法 |
CN114512617A (zh) * | 2020-11-17 | 2022-05-17 | 京东方科技集团股份有限公司 | 一种发光器件、显示装置和发光器件的制作方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10251633A (ja) * | 1997-03-17 | 1998-09-22 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用発光材料およびそれを使用した有機エレクトロルミネッセンス素子 |
JP2000016973A (ja) * | 1998-04-28 | 2000-01-18 | Canon Inc | 新規なトリアリ―ルアミン化合物及び該化合物を用いた発光素子 |
JP2001039933A (ja) * | 1999-07-30 | 2001-02-13 | Mitsui Chemicals Inc | アミン化合物 |
JP2005268228A (ja) * | 2004-03-19 | 2005-09-29 | Lg Electron Inc | 有機電界発光素子 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5061569A (en) * | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
US6517957B1 (en) * | 1997-05-19 | 2003-02-11 | Canon Kabushiki Kaisha | Organic compound and electroluminescent device using the same |
US6833200B2 (en) * | 1998-04-28 | 2004-12-21 | Canon Kabushiki Kaisha | Luminescent device with a triarylamine compound |
JP4233070B2 (ja) * | 1999-08-23 | 2009-03-04 | 三井化学株式会社 | アミン化合物 |
KR100662949B1 (ko) * | 1999-09-30 | 2006-12-28 | 이데미쓰 고산 가부시키가이샤 | 아민 화합물 및 이를 이용한 유기 전자발광 소자 |
JP2002367786A (ja) * | 2001-06-08 | 2002-12-20 | Toray Ind Inc | 発光素子 |
JP4003824B2 (ja) * | 2001-07-11 | 2007-11-07 | 富士フイルム株式会社 | 発光素子 |
JP3848262B2 (ja) * | 2002-03-27 | 2006-11-22 | キヤノン株式会社 | オリゴフルオレニレン化合物及び有機発光素子 |
JP3902993B2 (ja) | 2002-08-27 | 2007-04-11 | キヤノン株式会社 | フルオレン化合物及びそれを用いた有機発光素子 |
JP2004315366A (ja) * | 2003-02-28 | 2004-11-11 | Yasuhiko Shirota | 発光材料およびそれを用いるエレクトロルミネッセンス素子 |
JP4736336B2 (ja) * | 2003-03-26 | 2011-07-27 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、照明装置および表示装置 |
US7485376B2 (en) * | 2003-03-26 | 2009-02-03 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, illuminator, and display |
JP3848307B2 (ja) * | 2003-06-27 | 2006-11-22 | キヤノン株式会社 | アミノアントリル誘導基置換化合物およびそれを使用した有機発光素子 |
JP3848306B2 (ja) * | 2003-06-27 | 2006-11-22 | キヤノン株式会社 | アントリル誘導基置換化合物およびそれを使用した有機発光素子 |
JP2005285410A (ja) * | 2004-03-29 | 2005-10-13 | Fuji Photo Film Co Ltd | 有機電界発光素子 |
JP4065547B2 (ja) * | 2004-04-12 | 2008-03-26 | キヤノン株式会社 | フルオレン化合物及びそれを用いた有機発光素子 |
JP4955971B2 (ja) * | 2004-11-26 | 2012-06-20 | キヤノン株式会社 | アミノアントリル誘導基置換ピレン化合物および有機発光素子 |
JP4378366B2 (ja) * | 2005-08-04 | 2009-12-02 | キヤノン株式会社 | 発光素子アレイ |
JP5064678B2 (ja) * | 2005-12-16 | 2012-10-31 | キヤノン株式会社 | 有機発光素子 |
-
2006
- 2006-11-20 JP JP2006312927A patent/JP4653061B2/ja not_active Expired - Fee Related
- 2006-12-13 KR KR1020087017390A patent/KR101036399B1/ko active IP Right Grant
- 2006-12-13 US US11/912,621 patent/US20090091244A1/en not_active Abandoned
- 2006-12-13 WO PCT/JP2006/325318 patent/WO2007072838A1/en active Application Filing
- 2006-12-13 CN CN2006800208323A patent/CN101193851B/zh not_active Expired - Fee Related
- 2006-12-13 EP EP06834988.5A patent/EP1966123B1/en not_active Not-in-force
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10251633A (ja) * | 1997-03-17 | 1998-09-22 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用発光材料およびそれを使用した有機エレクトロルミネッセンス素子 |
JP2000016973A (ja) * | 1998-04-28 | 2000-01-18 | Canon Inc | 新規なトリアリ―ルアミン化合物及び該化合物を用いた発光素子 |
JP2001039933A (ja) * | 1999-07-30 | 2001-02-13 | Mitsui Chemicals Inc | アミン化合物 |
JP2005268228A (ja) * | 2004-03-19 | 2005-09-29 | Lg Electron Inc | 有機電界発光素子 |
Also Published As
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US20090091244A1 (en) | 2009-04-09 |
KR101036399B1 (ko) | 2011-05-23 |
WO2007072838A1 (en) | 2007-06-28 |
EP1966123A1 (en) | 2008-09-10 |
CN101193851B (zh) | 2013-06-12 |
JP2007191465A (ja) | 2007-08-02 |
CN101193851A (zh) | 2008-06-04 |
KR20080077023A (ko) | 2008-08-20 |
EP1966123B1 (en) | 2014-11-19 |
EP1966123A4 (en) | 2010-12-08 |
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