JP5564305B2 - トリアゾール誘導体、発光素子、及び発光装置 - Google Patents
トリアゾール誘導体、発光素子、及び発光装置 Download PDFInfo
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- JP5564305B2 JP5564305B2 JP2010076823A JP2010076823A JP5564305B2 JP 5564305 B2 JP5564305 B2 JP 5564305B2 JP 2010076823 A JP2010076823 A JP 2010076823A JP 2010076823 A JP2010076823 A JP 2010076823A JP 5564305 B2 JP5564305 B2 JP 5564305B2
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- light
- layer
- emitting
- emitting element
- triazole derivative
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- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 36
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- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- 239000010410 layer Substances 0.000 description 263
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
- Y02B20/30—Semiconductor lamps, e.g. solid state lamps [SSL] light emitting diodes [LED] or organic LED [OLED]
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
本実施の形態では、本発明の一態様であるトリアゾール誘導体について説明する。
実施の形態1のトリアゾール誘導体を用いた発光素子の一態様について図1(A)を用いて以下に説明する。
本実施の形態では、実施の形態2で示した構成と異なる構成の発光素子について図3(A)(B)を用いて説明する。
本実施の形態は、複数の発光ユニットを積層した構成の発光素子(以下、積層型素子という)の態様について、図4を参照して説明する。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する発光素子である。
本実施の形態では、上記実施の形態で示したトリアゾール誘導体を用いて作製された発光装置について説明する。
本実施の形態では、本発明を適用した一様態である発光装置をその一部に含む電子機器について説明する。本実施の形態の電子機器は、実施の形態1に示したトリアゾール誘導体を含み、高信頼性の表示部を有する。
このステップは、9−(2’−ブロモビフェニル−4−イル)−9H−カルバゾールの合成工程であり、そのステップを合成スキーム(E1−1)に示すと共にそのステップの反応に関し以下において詳述する。
このステップは、4’−(9H−カルバゾール−9−イル)ビフェニル−2−ボロン酸の合成工程であり、そのステップを合成スキーム(E1−2)に示すと共にそのステップの反応に関し以下において詳述する。
このステップは、9−(2’’−ブロモ−[1,1’:2’,1’’]テルフェニル−4−イル)−9H−カルバゾールの合成工程であり、そのステップを合成スキーム(E1−3)に示すと共にそのステップの反応に関し以下において詳述する。
このステップは、4’’−(9H−カルバゾール−9−イル)−[1,1’:2’,1’’]テルフェニル−2−ボロン酸の合成工程であり、そのステップを合成スキーム(E1−4)に示すと共にそのステップの反応に関し以下において詳述する。
このステップは、9−[4’’’−(4,5−ジフェニル−4H−1,2,4−トリアゾール−3−イル)−[1,1’:2’,1’’:2’’,1’’’]クアテルフェニル−4−イル]−9H−カルバゾール(略称:Z−CzPTAZ)の合成工程であり、そのステップを合成スキーム(E1−5)に示すと共にそのステップの反応に関し以下において詳述する。
1H NMR(CDCl3,300MHz):δ=6.60−6.68(m,4H)、7.06−7.56(m,29H)、8.14(d,J=7.8Hz,2H)
まず、ガラス基板2101上に、酸化珪素を含むインジウムスズ酸化物をスパッタリング法にて成膜し、第1の電極2102を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
まず、ガラス基板2101上に、酸化珪素を含むインジウムスズ酸化物をスパッタリング法にて成膜し、第1の電極2102を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
102 第1の電極
103 第1の層
104 第2の層
105 第3の層
105a 発光層
105b 発光層
106 第4の層
107 第2の電極
108 EL層
130 層
301 基板
302 第1の電極
303 第1の層
304 第2の層
305 第3の層
306 第4の層
307 第2の電極
308 EL層
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 ソース側駆動回路
602 画素部
603 ゲート側駆動回路
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 第1の電極
614 絶縁物
616 発光物質を含む層
617 第2の電極
618 発光素子
623 nチャネル型TFT
624 pチャネル型TFT
901 筐体
902 液晶層
903 バックライト
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 発光物質を含む層
956 電極
2001 筐体
2002 光源
2101 ガラス基板
2102 第1の電極
2103 第1の層
2104 第2の層
2105 第3の層
2106 第4の層
2107 第5の層
2108 第2の電極
3001 照明装置
8001 筐体
8002 支持台
8003 表示部
8004 スピーカー部
8005 ビデオ入力端子
8102 筐体
8103 表示部
8104 キーボード
8105 外部接続ポート
8106 ポインティングデバイス
8202 表示部
8204 外部接続ポート
8205 リモコン受信部
8206 受像部
8209 操作キー
8403 表示部
8404 音声入力部
8405 音声出力部
8406 操作キー
8407 外部接続ポート
Claims (6)
- 式(G1)で表されるトリアゾール誘導体。
(式中、Ar 1 〜Ar 3 は、環を形成する炭素数6〜10のアリール基を表し、置換基を有していても良い。また、R 1 は炭素数1〜4のアルキル基、又は、環を形成する炭素数6〜10のアリール基のいずれかを表し、R 1 が環を形成する炭素数6〜10のアリール基の場合、置換基を有していても良い。また、Ar 1 とαの炭素、又は、Ar 1 とAr 2 はそれぞれ互いに結合してカルバゾール骨格を形成していても良い。) - 式(G2)で表されるトリアゾール誘導体。
(式中、Ar 3 は環を形成する炭素数6〜10のアリール基を表し、置換基を有していても良い。また、R 1 は炭素数1〜4のアルキル基、又は、環を形成する炭素数6〜10のアリール基のいずれかを表し、R 1 が環を形成する炭素数6〜10のアリール基の場合、置換基を有していても良い。また、R 11 〜R 20 は、水素、炭素数1〜4のアルキル基、又は、環を形成する炭素数6〜10のアリール基のいずれかを表す。また、αの炭素、βの炭素、及びγの炭素のいずれか2は、それぞれ互いに結合してカルバゾール骨格を形成していてもよい。) - 式(G4)で表されるトリアゾール誘導体。
(式中、R 11 〜R 30 は、水素、炭素数1〜4のアルキル基、又は環を形成する炭素数6〜10のアリール基のいずれかを表す。また、αの炭素、βの炭素、及びγの炭素のいずれか2は、それぞれ互いに結合してカルバゾール骨格を形成していてもよい。) - 式(G4)で表されるトリアゾール誘導体。
(式中、R 11 〜R 30 は、水素、炭素数1〜4のアルキル基、又は環を形成する炭素数6〜10のアリール基のいずれかを表す。また、βの炭素とγの炭素は、互いに結合してカルバゾール骨格を形成している。) - 請求項1乃至4のいずれか一に記載のトリアゾール誘導体と、発光物質とを含む発光層を有する発光素子。
- 請求項5に記載の発光素子を有する発光装置。
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US (1) | US8293921B2 (ja) |
JP (1) | JP5564305B2 (ja) |
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CN (1) | CN101875652B (ja) |
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US11230521B2 (en) | 2017-08-01 | 2022-01-25 | Samsung Display Co., Ltd. | Monoamine compound and organic electroluminescence device including the same |
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CN102144313B (zh) | 2008-09-05 | 2014-07-30 | 株式会社半导体能源研究所 | 有机半导体材料和发光元件、发光装置、照明系统和使用这些的电子装置 |
TWI469968B (zh) * | 2009-03-31 | 2015-01-21 | Semiconductor Energy Lab | 雜環化合物及使用該雜環化合物之發光元件、發光裝置、照明裝置和電子設備 |
US8993125B2 (en) | 2010-05-21 | 2015-03-31 | Semiconductor Energy Laboratory Co., Ltd. | Triazole derivative, and light-emitting element, light-emitting device, electronic device and lighting device using the triazole derivative |
WO2012017842A1 (en) | 2010-08-02 | 2012-02-09 | Semiconductor Energy Laboratory Co., Ltd. | Triazole derivative, heterocyclic compound, light-emitting element, light-emitting device, electronic device and lighting device |
CN116056479A (zh) * | 2011-02-16 | 2023-05-02 | 株式会社半导体能源研究所 | 发光元件 |
US9273079B2 (en) | 2011-06-29 | 2016-03-01 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device |
JP6363836B2 (ja) | 2012-12-20 | 2018-07-25 | 株式会社半導体エネルギー研究所 | 発光素子 |
CN103468246B (zh) * | 2013-09-04 | 2016-05-11 | 吉林奥来德光电材料股份有限公司 | 一种含1,2,4-三氮唑类的有机发光材料、其制备方法及其电致发光器件 |
KR102353647B1 (ko) | 2014-08-29 | 2022-01-20 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 표시 장치, 전자 기기, 및 조명 장치 |
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TW201721922A (zh) | 2015-09-30 | 2017-06-16 | 半導體能源研究所股份有限公司 | 發光元件,顯示裝置,電子裝置,及照明裝置 |
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JP3654909B2 (ja) * | 1996-12-28 | 2005-06-02 | Tdk株式会社 | 有機el素子 |
JP4364130B2 (ja) | 1996-12-28 | 2009-11-11 | Tdk株式会社 | 有機el素子 |
US5869929A (en) * | 1997-02-04 | 1999-02-09 | Idemitsu Kosan Co., Ltd. | Multicolor luminescent device |
JP4103491B2 (ja) * | 2002-08-07 | 2008-06-18 | 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及び表示装置 |
US7271406B2 (en) * | 2003-04-15 | 2007-09-18 | 3M Innovative Properties Company | Electron transport agents for organic electronic devices |
WO2004107822A1 (ja) * | 2003-05-29 | 2004-12-09 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子 |
JP4587703B2 (ja) * | 2004-05-07 | 2010-11-24 | ケミプロ化成株式会社 | 新規クオーターフェニレン誘導体、およびそれを用いた有機el素子 |
CN101171239B (zh) * | 2005-04-28 | 2013-08-14 | 西巴特殊化学品控股有限公司 | 场致发光器件 |
JP4871607B2 (ja) * | 2006-02-23 | 2012-02-08 | 富士フイルム株式会社 | 有機電界発光素子 |
CN101679383B (zh) * | 2007-05-17 | 2014-10-29 | 株式会社半导体能源研究所 | 三唑衍生物,和使用三唑衍生物的发光元件、发光器件和电子器件 |
WO2009081718A1 (en) * | 2007-12-21 | 2009-07-02 | Semiconductor Energy Laboratory Co., Ltd. | Triazole derivative, light-emitting element, light-emitting device, and electronic device |
TWI371225B (en) * | 2008-06-02 | 2012-08-21 | Ind Tech Res Inst | Organic light-emitting device |
JP5473490B2 (ja) * | 2008-09-01 | 2014-04-16 | 株式会社半導体エネルギー研究所 | トリアゾール誘導体及び発光素子 |
CN102144313B (zh) * | 2008-09-05 | 2014-07-30 | 株式会社半导体能源研究所 | 有机半导体材料和发光元件、发光装置、照明系统和使用这些的电子装置 |
TWI469968B (zh) * | 2009-03-31 | 2015-01-21 | Semiconductor Energy Lab | 雜環化合物及使用該雜環化合物之發光元件、發光裝置、照明裝置和電子設備 |
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- 2010-03-29 TW TW099109428A patent/TWI476184B/zh not_active IP Right Cessation
- 2010-03-30 US US12/750,400 patent/US8293921B2/en not_active Expired - Fee Related
- 2010-03-30 CN CN201010158614.4A patent/CN101875652B/zh not_active Expired - Fee Related
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Cited By (1)
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US11230521B2 (en) | 2017-08-01 | 2022-01-25 | Samsung Display Co., Ltd. | Monoamine compound and organic electroluminescence device including the same |
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TW201105638A (en) | 2011-02-16 |
TWI476184B (zh) | 2015-03-11 |
CN101875652B (zh) | 2014-09-24 |
JP2010254679A (ja) | 2010-11-11 |
CN101875652A (zh) | 2010-11-03 |
KR20100109413A (ko) | 2010-10-08 |
US8293921B2 (en) | 2012-10-23 |
US20100244674A1 (en) | 2010-09-30 |
KR101764599B1 (ko) | 2017-08-03 |
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