JP5738699B2 - 有機金属錯体、発光素子、発光装置、電子機器、及び照明装置 - Google Patents
有機金属錯体、発光素子、発光装置、電子機器、及び照明装置 Download PDFInfo
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- JP5738699B2 JP5738699B2 JP2011158072A JP2011158072A JP5738699B2 JP 5738699 B2 JP5738699 B2 JP 5738699B2 JP 2011158072 A JP2011158072 A JP 2011158072A JP 2011158072 A JP2011158072 A JP 2011158072A JP 5738699 B2 JP5738699 B2 JP 5738699B2
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- 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
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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- 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
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Classifications
-
- H—ELECTRICITY
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Description
本実施の形態では、本発明の一態様の有機金属錯体について説明する。
下記一般式(G1)で表される有機金属錯体の合成方法の一例について説明する。
まず、下記一般式(G0)で表される3−(3−ピリジル)−4H−1,2,4−トリアゾール誘導体は新規物質であるので、その合成法の一例について説明する。
下記合成スキーム(b)に示すように、ステップ1で得られる3−(3−ピリジル)−4H−1,2,4−トリアゾール誘導体(G0)と、ハロゲンを含むイリジウムの金属化合物(塩化イリジウム水和物、ヘキサクロロイリジウム酸アンモニウム等)、又はイリジウムの有機金属錯体(アセチルアセトナト錯体、ジエチルスルフィド錯体、3−(3−ピリジル)−4H−1,2,4−トリアゾール誘導体を配位子とするμ−ハロゲン架橋複核錯体、3−(3−ピリジル)−4H−1,2,4−トリアゾール誘導体を配位子とするμ−オキソ架橋複核錯体等)とを混合した後、加熱することにより、一般式(G1)で表される有機金属錯体を得ることができる。
本実施の形態では、本発明の一態様として、実施の形態1で説明した有機金属錯体を発光層に用いた発光素子について図1(A)を用いて説明する。
本発明の一態様の発光素子は、複数の発光層を有するものであってもよい。複数の発光層を設け、それぞれの発光層から発光させることで、複数の発光が混合された発光を得ることができる。したがって、例えば白色光を得ることができる。本実施の形態では、複数の発光層を有する発光素子の態様について図1(B)を用いて説明する。
本実施の形態では、本発明の一態様として、発光素子においてEL層を複数有する構造(以下、積層型素子という)について、図1(C)を用いて説明する。この発光素子は、第1の電極101と第2の電極103との間に、複数のEL層(第1のEL層700、第2のEL層701)を有する積層型発光素子である。なお、本実施の形態では、EL層が2層の場合について示すが、3層以上としても良い。
本実施の形態では、本発明の一態様として、発光素子を用いて作製される発光装置であるパッシブマトリクス型の発光装置、及びアクティブマトリクス型の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態様である発光装置を用いて完成させた様々な電子機器及び照明器具の一例について、図7、図8を用いて説明する。
本実施例では、実施の形態1の構造式(100)で表される本発明の一態様である有機金属錯体、トリス[5−メチル−4−フェニル−3−(5−ピリジル)−4H−1,2,4−トリアゾラト]イリジウム(III)(略称:[Ir(Mpytz)3])の合成例を具体的に例示する。なお、[Ir(Mpytz)3]の構造を以下に示す。
まず、N−[1−(エチルスルファニル)エチリデン]アニリン3.64g、1−ブタノール20mL、ニコチン酸ヒドラジド2.78gを100mL三ツ口フラスコに入れ、130℃で22時間撹拌した。撹拌後、この反応溶液を減圧下にて濃縮し油状物を得た。この油状物を酢酸エチルで洗浄し、吸引ろ過して固体を得た。この固体を、酢酸エチルを展開溶媒とするアルミナカラムクロマトグラフィーにより精製した。得られたフラクションを濃縮して固体を得た。この固体を酢酸エチルとヘキサンの混合溶媒にて洗浄して3−メチル−4−フェニル−5−(3−ピリジル)−4H−1,2,4−トリアゾール(略称:HMpytz)を得た(白色固体、収率42%)。ステップ1の合成スキームを下記(a−1)に示す。
次に、上記ステップ1にて得られた配位子HMpytz1.01g、トリス(アセチルアセトナト)イリジウム(III)0.42gを、三方コックを付けた反応容器に入れ、反応容器内をアルゴン置換した。その後、245℃にて48時間加熱し、反応させた。反応物をジクロロメタンに溶解し、この溶液をセライト(和光純薬工業株式会社、カタログ番号:531−16855)とシリカゲルの積層物をろ紙の上に敷いた状態で吸引ろ過した。得られたろ液の溶媒を留去し、残渣をアセトン、次いで酢酸エチルにて洗浄した。洗浄後の固体をエタノールとヘキサンの混合溶媒にて再結晶化し、目的物である黄色粉末を収率1%で得た。合成スキームを下記(b−1)に示す。
本実施例では、実施の形態1の構造式(104)で表される本発明の一態様である有機金属錯体、トリス[5−イソプロピル−3−(6−メチル−5−ピリジル)−4−フェニル−4H−1,2,4−トリアゾラト]イリジウム(III)(略称:[Ir(iPrMpytz)3])の合成例を具体的に例示する。なお、[Ir(iPrMpytz)3]の構造を以下に示す。
まず、2−メチルニコチン酸エチル4.12g、1−ブタノール15mL、ヒドラジン一水和物(NH2NH2・H2O)1.25gを100mL三ツ口フラスコに入れて80℃で19時間加熱撹拌した。撹拌後、さらにヒドラジン一水和物2.38gを加えて15時間加熱撹拌した。撹拌後、反応溶液を飽和食塩水に注ぎ入れ、室温で30分間撹拌した。この混合物の有機層と水層を分液し、水層から有機物をクロロホルムで抽出した。得られた抽出溶液と該有機層を合わせ、無水硫酸マグネシウムを加えて乾燥させた。乾燥後の混合物を自然ろ過し、ろ液を濃縮して固体を得た。得られた固体を酢酸エチルとヘキサンの混合溶媒で洗浄して、2−メチルニコチン酸ヒドラジドを得た(白色固体、収率42%)。ステップ1の合成スキームを下記(a−2)に示す。
次に、上記ステップ1で得られた2−メチルニコチン酸ヒドラジド1.70g、1−ブタノール30mL、N−[1−(エチルスルファニル)イソブチリデン]アニリン2.30gを100mL三ツ口フラスコに入れ、130℃で9時間加熱撹拌した。撹拌後、さらにN−[1−(エチルスルファニル)イソブチリデン]アニリン1.15gを加えて130℃で18時間加熱撹拌した。撹拌後、1−ブタノールを減圧下にて留去し、油状物を得た。この油状物をシリカゲルカラムクロマトグラフィーにより精製した。展開溶媒には酢酸エチルを用いた。得られたフラクションを濃縮し固体を得た。この固体をさらにアルミナカラムクロマトグラフィーにより精製した。展開溶媒には酢酸エチルを用いた。得られたフラクションを濃縮して、固体を得た。この固体をヘキサンにて洗浄し、3−イソプロピル−5−(2−メチル−3−ピリジル)−4−フェニル−4H−1,2,4−トリアゾール(略称:HiPrMpytz)を得た(白色固体、収率28%)。ステップ2の合成スキームを下記(b−2)に示す。
さらに、上記ステップ2にて得られた配位子HiPrMpytz0.87g、トリス(アセチルアセトナト)イリジウム(III)0.31gを、三方コックを付けた反応容器に入れ、反応容器内をアルゴン置換した。その後、250℃にて49時間加熱し、反応させた。反応物をジクロロメタンに溶解し、シリカゲルカラムクロマトグラフィーにより精製した。展開溶媒には酢酸エチルを用いた。得られたフラクションを濃縮して固体を得た。得られた固体を酢酸エチルで洗浄し、さらにアセトンにて再結晶化することにより、目的物の淡黄色粉末を収率28%で得た。合成スキームを下記(c−2)に示す。
まず、ガラス基板1100上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極1101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1100上に、ITSOをスパッタリング法にて成膜し、第1の電極1101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。
上記実施例で用いた、2−[3−(ジベンゾチオフェン−4−イル)フェニル]−1−フェニル−1H−ベンゾイミダゾール(略称:mDBTBIm−II)の合成方法について説明する。mDBTBIm−IIの構造を以下に示す。
mDBTBIm−IIの合成スキームを(x−1)に示す。
1H NMR(CDCl3,300MHz):δ=7.23−7.60(m,13H)、7.71−7.82(m,3H)、7.90−7.92(m,2H)、8.10−8.17(m,2H)。
102 EL層
103 第2の電極
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
213 発光層
214 分離層
215 発光層
305 電荷発生層
401 基板
402 絶縁層
403 第1の電極
404 隔壁
405 開口部
406 隔壁
407 EL層
408 第2の電極
501 基板
503 走査線
505 領域
506 隔壁
508 データ線
509 接続配線
510 入力端子
512 入力端子
601 素子基板
602 画素部
603 駆動回路部
604 駆動回路部
605 シール材
606 封止基板
607 配線
608 FPC
609 nチャネル型TFT
610 pチャネル型TFT
611 スイッチング用TFT
612 電流制御用TFT
613 陽極
614 絶縁物
615 EL層
616 陰極
617 発光素子
618 空間
700 EL層
701 EL層
801 照明装置
802 照明装置
803 卓上照明器具
1100 基板
1101 第1の電極
1103 第2の電極
1111 正孔注入層
1112 正孔輸送層
1113 発光層
1114a 第1の電子輸送層
1114b 第2の電子輸送層
1114c 第3の電子輸送層
1115 電子注入層
511a FPC
511b FPC
7100 テレビジョン装置
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 ポインティングデバイス
7301 筐体
7302 筐体
7303 連結部
7304 表示部
7305 表示部
7306 スピーカ部
7307 記録媒体挿入部
7308 LEDランプ
7309 操作キー
7310 接続端子
7311 センサ
7312 マイクロフォン
7400 携帯電話機
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
7501 照明部
7502 傘
7503 可変アーム
7504 支柱
7505 台
7506 電源
Claims (9)
- 一般式(G1)で表される有機金属錯体。
- 一般式(G1)で表される有機金属錯体。
(式中、R1は、炭素数1〜4のアルキル基、又は置換もしくは無置換の炭素数5〜6のシクロアルキル基を表し、R2〜R4は、それぞれ独立に、水素、炭素数1〜4のアルキル基、又は置換もしくは無置換の炭素数6〜13のアリール基を表し、R5は、炭素数1〜4のアルキル基、置換もしくは無置換の炭素数5〜6のシクロアルキル基、又は置換もしくは無置換の炭素数6〜13のアリール基を表す。) - 一般式(G2)で表される有機金属錯体。
(式中、R1は、炭素数1〜4のアルキル基を表し、R2〜R4は、それぞれ独立に、水素、又は炭素数1〜4のアルキル基を表し、R6〜R10は、それぞれ独立に、水素、又は炭素数1〜4のアルキル基を表す。) - 請求項1乃至請求項3のいずれか一項において、
R2がメチル基である有機金属錯体。 - 一対の電極間に、
請求項1乃至請求項4のいずれか一項に記載の有機金属錯体を有する発光素子。 - 一対の電極間に発光層を有し、
前記発光層は請求項1乃至請求項4のいずれか一項に記載の有機金属錯体を有する発光素子。 - 請求項5又は請求項6に記載の発光素子を有する発光装置。
- 請求項7に記載の発光装置を有する電子機器。
- 請求項7に記載の発光装置を有する照明装置。
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US9155158B2 (en) | 2011-04-01 | 2015-10-06 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, display device, electronic device, and lighting device |
KR20140080606A (ko) | 2012-12-12 | 2014-07-01 | 삼성전자주식회사 | 유기 금속 착물, 이를 이용한 유기 전계 발광 소자 및 표시 장치 |
CN104078570A (zh) * | 2013-03-29 | 2014-10-01 | 海洋王照明科技股份有限公司 | 有机电致发光器件及其制备方法 |
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JP6187214B2 (ja) * | 2013-12-09 | 2017-08-30 | コニカミノルタ株式会社 | 金属錯体、有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
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CN102307886A (zh) | 2009-02-06 | 2012-01-04 | 索尔维公司 | 含吡啶基三唑配体的磷光铱络合物 |
EP2496591B1 (en) | 2009-11-02 | 2018-05-30 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, display device, electronic device, and lighting device |
JP5738699B2 (ja) | 2010-07-28 | 2015-06-24 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、及び照明装置 |
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Cited By (2)
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JP2015143267A (ja) * | 2010-07-28 | 2015-08-06 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、照明装置 |
US9461252B2 (en) | 2010-07-28 | 2016-10-04 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device |
Also Published As
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JP2015143267A (ja) | 2015-08-06 |
JP5961305B2 (ja) | 2016-08-02 |
KR101836069B1 (ko) | 2018-03-08 |
US8795851B2 (en) | 2014-08-05 |
US20140339533A1 (en) | 2014-11-20 |
KR20120023525A (ko) | 2012-03-13 |
JP2012046492A (ja) | 2012-03-08 |
US9461252B2 (en) | 2016-10-04 |
US20120025178A1 (en) | 2012-02-02 |
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