JP2012144459A - 有機化合物、有機発光素子及び画像表示装置 - Google Patents
有機化合物、有機発光素子及び画像表示装置 Download PDFInfo
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- JP2012144459A JP2012144459A JP2011002263A JP2011002263A JP2012144459A JP 2012144459 A JP2012144459 A JP 2012144459A JP 2011002263 A JP2011002263 A JP 2011002263A JP 2011002263 A JP2011002263 A JP 2011002263A JP 2012144459 A JP2012144459 A JP 2012144459A
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- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 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
- 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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Abstract
Description
以下に示す試薬、溶媒を反応容器内に投入した。
化合物X1:4.0g(13mmol)
化合物X2:2.8g(13mmol)
エタノール:65ml
以下に示す試薬、溶媒を反応容器内に投入した。
化合物X3:5.0g(10mmol)
化合物X4:6.1g(21mmol)
キシレン:100ml
以下に示す試薬、溶媒を反応容器内に投入した。
化合物X5:1.0g(1.5mmol)
化合物X6:0.55g(2.2mmol)
DMF:20ml
ビス(ジベンジリデンアセトン)パラジウム(0):0.84g(1.5mmol)
1,8―ジアザビシクロ[5.4.0]ウンデセ−7−エン:0.44g(2.9mmol)
トリシクロヘキシルフォスフィン:0.81g(2.9mmol)
以下に示す試薬、溶媒を反応容器内に投入した。
化合物X7:10g(55mmol)
化合物X2:12g(55mmol)
エタノール:200ml
以下に示す試薬、溶媒を反応容器内に投入した。
化合物X8:10g(28mmol)
化合物X4:17g(56mmol)
キシレン:100ml
以下に示す試薬、溶媒を反応容器内に投入した。
化合物X9:2.0g(3.6mmol)
化合物X10:2.0g(5.3mmol)
DMF:40ml
ビス(ジベンジリデンアセトン)パラジウム(0):2.0g(3.6mmol)
1,8―ジアザビシクロ[5.4.0]ウンデセ−7−エン:1.1g(7.1mmol)
トリシクロヘキシルフォスフィン:2.0g(7.1mmol)
DART−TOF−MASS:M+H=563.2
実施例2(1)において、化合物X2に代えて下記に示される化合物X11を使用する以外は、実施例2と同様の方法で合成を行うことにより、例示化合物XX−5を得た。
DART−TOF−MASS:M+H=805.3
実施例2(1)において、化合物X7に代えて下記に示される化合物X12を使用する以外は、実施例2と同様の方法で合成を行うことにより、例示化合物XX−10を得た。
DART−TOF−MASS:M+H=805.3
実施例1(3)において、化合物X6の代わりに下記に示されるX13を使用する以外は、実施例1と同様の方法で合成を行うことにより、例示化合物XY−1を得た。
DART−TOF−MASS:M+H=765.3
実施例2(1)において、化合物X2の代わりに下記に示されるX14を使用する以外は、実施例2と同様の方法で合成を行うことにより、例示化合物XY−3を得た。
DART−TOF−MASS:M+H=877.5
本実施例では、基板上に、陽極、ホール注入層、ホール輸送層、発光層、ホール・エキシトンブロッキング層、電子輸送層、陰極が順次形成された有機発光素子を作製した。以下に、本実施例で使用した材料の一部を示す。
実施例7において、G−2、G−3及びゲストを、表5に示される化合物に適宜変更する以外は、実施例7と同様の方法により有機発光素子を作製した。得られた素子について実施例7と同様に素子の特性を測定・評価した。測定の結果を表5に示す。尚、表5において、G−2として使用したH2、H7、H10、H15、H17、H19、H21及びH23、並びにG−3として使用したH2、H7、H10、H17、H19、H21、H23及びH24は、それぞれ表3に示されるホストである。
本実施例では、基板上に、陽極、ホール注入層、ホール輸送層、発光層、電子輸送層、電子注入層、陰極が順次形成された有機発光素子を作製した。尚、本実施例で作製される有機発光素子は共振構造を有している。以下に、本実施例で使用した材料の一部を示す。
以上により、有機発光素子を作製した。
実施例18において、G−13、G−14及びゲストを、表7に示される化合物に適宜変更する以外は、実施例18と同様の方法により有機発光素子を作製した。得られた素子について実施例18と同様に素子の特性を測定・評価した。測定の結果を表7に示す。尚、表7において、G−13として使用したH6及びH16、並びにG−14として使用したH21及びH24は、それぞれ表3に示されるホストである。
本実施例では、基板上に、陽極、ホール輸送層、第1発光層、第2発光層、ホール・エキシトンブロッキング層、電子輸送層、陰極が順次形成された有機発光素子を作製した。尚、本実施例の有機発光素子は発光層が複数あるので、各発光層に含まれるゲストが個別あるいは同時に発光する態様である。以下に、本実施例で使用した材料の一部を示す。
実施例21において、G−22、G−23、G−24及びゲストを、表9に示される化合物に適宜変更する以外は、実施例22と同様の方法により有機発光素子を作製した。得られた素子について実施例22と同様に素子の特性を測定・評価した。測定の結果を表9に示す。尚、表9において、G−22として使用したH18及びH23、G−23として使用したH18及びH23、並びにG−24として使用したH4及びH10は、それぞれ表3に示されるホストである。
Claims (9)
- 前記R1乃至R20が、それぞれ水素原子及び置換あるいは無置換のアリール基から選ばれる置換基であることを特徴とする、請求項1に記載の有機化合物。
- R2及びR9が、置換あるいは無置換のアリール基であり、R1、R3乃至R8及びR10乃至R20が水素原子であることを特徴とする、請求項1又は2に記載の有機化合物。
- 分子構造中にターシャリーブチル基を2つ以上有することを特徴とする、請求項1乃至3のいずれか一項に記載の有機化合物。
- 陽極と陰極と、
前記陽極と前記陰極との間に配置される有機化合物層と、を有する有機発光素子であって、
前記有機化合物層の少なくとも一層に、請求項1乃至4のいずれか一項に記載の有機化合物が含まれることを特徴とする、有機発光素子。 - 前記有機化合物が、発光層に含まれることを特徴とする、請求項5に記載の有機発光素子。
- 黄色発光することを特徴とする、請求項6に記載の有機発光素子。
- 複数の画素を有する表示装置であって、
前記複数の画素が、請求項5乃至7のいずれか一項に記載の有機発光素子と、前記有機発光素子に電気接続されるTFT素子と、をそれぞれ有することを特徴とする、表示装置。 - 画像情報を入力するための入力部と、画像を出力するための表示部と、を有する画像入力装置であって、
前記表示部が複数の画素を有し、
前記複数の画素が、請求項5乃至7のいずれか一項に記載の有機発光素子と、前記有機発光素子に電気接続されるTFT素子と、をそれぞれ有することを特徴とする、画像入力装置。
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JP2011002263A JP5713686B2 (ja) | 2011-01-07 | 2011-01-07 | 有機化合物、有機発光素子及び画像表示装置 |
US13/978,058 US9397298B2 (en) | 2011-01-07 | 2011-12-09 | Organic compound, organic light-emitting device, and image display device |
CN201180063852XA CN103313957A (zh) | 2011-01-07 | 2011-12-09 | 有机化合物、有机发光器件和图像显示装置 |
PCT/JP2011/079261 WO2012093578A1 (en) | 2011-01-07 | 2011-12-09 | Organic compound, organic light-emitting device, and image display device |
EP11855218.1A EP2661418A4 (en) | 2011-01-07 | 2011-12-09 | ORGANIC CONNECTION, ORGANIC LIGHT-EMITTING DEVICE AND IMAGE DISPLAY DEVICE |
KR1020137020177A KR101555110B1 (ko) | 2011-01-07 | 2011-12-09 | 유기 화합물, 유기 발광 디바이스, 및 화상 표시 디바이스 |
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WO2013084833A1 (en) * | 2011-12-06 | 2013-06-13 | Canon Kabushiki Kaisha | Novel organic compound, organic light emitting device, and image display device |
JP2015530735A (ja) * | 2012-07-23 | 2015-10-15 | メルク パテント ゲーエムベーハー | 2−ジアリールアミノフルオレン誘導体およびそれらを含む有機電子素子 |
WO2016204150A1 (ja) * | 2015-06-16 | 2016-12-22 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
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JP5674707B2 (ja) * | 2012-05-22 | 2015-02-25 | 株式会社東芝 | 表示装置 |
WO2013183280A1 (ja) | 2012-06-06 | 2013-12-12 | パナソニック株式会社 | インクジェット装置および有機elデバイスの製造方法 |
US9266324B2 (en) | 2012-07-05 | 2016-02-23 | Panasonic Intellectual Property Management Co., Ltd. | Inkjet apparatus and method for manufacturing organic EL device |
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JP2003347057A (ja) * | 2002-04-24 | 2003-12-05 | Eastman Kodak Co | 有機発光ダイオードデバイス |
JP2008187185A (ja) * | 2002-12-31 | 2008-08-14 | Eastman Kodak Co | 高効率電場発光デバイス |
JP2005068087A (ja) * | 2003-08-26 | 2005-03-17 | Mitsui Chemicals Inc | ベンゾフルオランテン化合物、および該ベンゾフルオランテン化合物を含有する有機電界発光素子 |
JP2009001499A (ja) * | 2007-06-19 | 2009-01-08 | Mitsui Chemicals Inc | 芳香族炭化水素化合物、および該芳香族炭化水素化合物を含有する有機電界発光素子 |
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JP2009302470A (ja) * | 2008-06-17 | 2009-12-24 | Mitsui Chemicals Inc | 有機トランジスタ |
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WO2013084833A1 (en) * | 2011-12-06 | 2013-06-13 | Canon Kabushiki Kaisha | Novel organic compound, organic light emitting device, and image display device |
US9590199B2 (en) | 2011-12-06 | 2017-03-07 | Canon Kabushiki Kaisha | Organic compound, organic light emitting device, and image display device |
JP2015530735A (ja) * | 2012-07-23 | 2015-10-15 | メルク パテント ゲーエムベーハー | 2−ジアリールアミノフルオレン誘導体およびそれらを含む有機電子素子 |
WO2016204150A1 (ja) * | 2015-06-16 | 2016-12-22 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
US10790449B2 (en) | 2015-06-16 | 2020-09-29 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device |
Also Published As
Publication number | Publication date |
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US20130292662A1 (en) | 2013-11-07 |
KR101555110B1 (ko) | 2015-09-22 |
EP2661418A4 (en) | 2016-02-24 |
US9397298B2 (en) | 2016-07-19 |
WO2012093578A1 (en) | 2012-07-12 |
KR20130112933A (ko) | 2013-10-14 |
CN103313957A (zh) | 2013-09-18 |
JP5713686B2 (ja) | 2015-05-07 |
EP2661418A1 (en) | 2013-11-13 |
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