JP2016121125A - 有機金属イリジウム錯体、発光素子、発光装置、電子機器、照明装置、および有機金属イリジウム錯体の合成方法 - Google Patents
有機金属イリジウム錯体、発光素子、発光装置、電子機器、照明装置、および有機金属イリジウム錯体の合成方法 Download PDFInfo
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- JP2016121125A JP2016121125A JP2015209686A JP2015209686A JP2016121125A JP 2016121125 A JP2016121125 A JP 2016121125A JP 2015209686 A JP2015209686 A JP 2015209686A JP 2015209686 A JP2015209686 A JP 2015209686A JP 2016121125 A JP2016121125 A JP 2016121125A
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- light
- emitting element
- iridium
- layer
- organometallic iridium
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 192
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 191
- 125000002524 organometallic group Chemical group 0.000 title claims abstract description 137
- 238000001308 synthesis method Methods 0.000 title claims description 10
- 239000003446 ligand Substances 0.000 claims abstract description 97
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 50
- 239000012535 impurity Substances 0.000 claims abstract description 40
- 238000004458 analytical method Methods 0.000 claims abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 14
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims abstract description 9
- 239000000758 substrate Substances 0.000 claims description 123
- 238000000034 method Methods 0.000 claims description 47
- 239000000460 chlorine Substances 0.000 claims description 40
- 229910052801 chlorine Inorganic materials 0.000 claims description 33
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 3
- 238000011002 quantification Methods 0.000 claims description 2
- 238000010606 normalization Methods 0.000 abstract 1
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- 239000000126 substance Substances 0.000 description 56
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- 239000000463 material Substances 0.000 description 37
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 7
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- 125000005595 acetylacetonate group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
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- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/311—Purifying organic semiconductor materials
-
- 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
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Abstract
Description
本実施の形態では、本発明の一態様である有機金属イリジウム錯体について説明する。
本実施の形態では、本発明の一態様として実施の形態1で示した有機金属イリジウム錯体を発光層に用いた発光素子について図1を用いて説明する。
本実施の形態では、本発明の一態様である有機金属イリジウム錯体をEL材料としてEL層に用い、電荷発生層を挟んでEL層を複数有する構造の発光素子(以下、タンデム型発光素子という)について説明する。
本実施の形態では、本発明の一態様である有機金属イリジウム錯体をEL層に用いた発光素子を有する発光装置について説明する。
本実施の形態では、本発明の一態様である発光装置を適用して完成させた様々な電子機器の一例について、図4、図5を用いて説明する。
本実施の形態では、本発明の一態様である発光素子を適用して作製される照明装置の構成について図6を用いて説明する。
本実施の形態では、実施の形態4で説明した発光装置を適用した応用品である照明装置の一例について、図7を用いて説明する。
本実施の形態においては、本発明の一態様の発光素子または本発明の一態様の発光装置を有するタッチパネルについて、図8〜図12を用いて説明を行う。
本実施例では、下記構造式(100)で表される有機金属イリジウム錯体、ビス[2−(6−フェニル−4−ピリミジニル−κN3)フェニル−κC](2,4−ペンタンジオナト−κ2O,O’)イリジウム(III)(略称:[Ir(dppm)2(acac)])の合成において、本発明の一態様であり、高純度な有機金属イリジウム錯体の合成方法について、ハロゲン等の不純物を含む有機金属イリジウム錯体が合成される比較例と併せて説明する。なお、[Ir(dppm)2(acac)]の構造を以下に示す。
はじめに、ステップ1で用いる配位子、4,6−ジフェニルピリミジン(略称:Hdppm)の純度分析をUPLCにより行った。その結果、面積比においてHdppm以外のものは0.1%未満であったため、純度は99.9%と算出された。すなわち、ステップ1では、このような高純度な配位子(Hdppm)を用いた。
次に、2−エトキシエタノール20mL、上記ステップ1で得た複核錯体[Ir(dppm)2Cl]2(ステップ1でサンプルごとにそれぞれ得られた複核錯体)1.60g、2,4−ペンタンジオン(略称:Hacac)0.36g、炭酸ナトリウム1.30gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を60分間照射した。ここで更にHacac 0.36gを加え、再度マイクロ波(2.45GHz 100W)を60分間照射することで加熱した。得られた混合物をエタノールで吸引ろ過した後、水、エタノールで洗浄した。得られた残渣を、ジクロロメタン:酢酸エチル=50:1を展開溶媒とするシリカゲルカラムクロマトグラフィーにより精製し、ジクロロメタンとヘキサンの混合溶媒にて再結晶することにより、[Ir(dppm)2(acac)]を得た(橙色粉末)。なお、ステップ1でサンプルAを用いた場合は、収率28%、サンプルBを用いた場合は、収率38%、サンプルCを用いた場合は、収率44%であった。
まず、ガラス製の基板900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より成膜し、陽極として機能する第1の電極901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。
作製した発光素子1、比較発光素子2、および比較発光素子3の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
本実施例では、下記構造式(200)で表される有機金属イリジウム錯体、トリス[2−(1H−ピラゾール−1−イル−κN2)フェニル−κC]イリジウム(III)(略称:[Ir(ppz)3])の合成において、本発明の一態様であり、高純度な有機金属イリジウム錯体の合成方法について、ハロゲン等の不純物を含む有機金属イリジウム錯体が合成される比較例と併せて説明する。なお、[Ir(ppz)3]の構造を以下に示す。
はじめに、ステップ1、2で用いる配位子、1−フェニルピラゾール(略称:Hppz)の純度分析をUPLCにより行った。その結果、面積比においてHppz以外のものは0.1%未満であったため、純度は99.9%と算出された。すなわち、ステップ1、2では、このような高純度な配位子(Hppz)を用いた。
まず、サンプルAを用いた合成例について説明する。2−エトキシエタノール30mL、水10mL、配位子(Hppz)2.5g、塩化イリジウム水和物(サンプルA)2.5gを、還流管を付けた丸底フラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を1.5時間照射し、反応させた。得られた混合物をエタノールで吸引ろ過した後、水、エタノールで洗浄し、複核錯体[Ir(ppz)2Cl]2を得た(白色粉末)。なお、収率76%であった。
次に、サンプルBを用いた合成例について説明する。2−エトキシエタノール30mL、水10mL、配位子(Hppz)5.0g、塩化イリジウム水和物(サンプルB)4.9gを、還流管を付けた丸底フラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を3時間照射し、反応させた。得られた混合物をエタノールで吸引ろ過した後、水、エタノールで洗浄し、複核錯体[Ir(ppz)2Cl]2を得た(白色粉末)。なお、収率80%であった。
上記ステップ1−1で得た複核錯体[Ir(ppz)2Cl]23.4g、配位子(Hppz)1.4g、炭酸カリウム4.6g、フェノール30gを200ml三口フラスコに入れ、窒素気流下、200℃で20時間加熱した。この反応混合物にメタノールを加えて超音波を照射し、吸引ろ過をして白色固体を得た。得られた固体を水、メタノールでさらに洗浄した。得られた固体を酢酸エチルにて再結晶することにより、[Ir(ppz)3]を収率48%で得た(白色粉末)。
上記ステップ1−2で得た複核錯体[Ir(ppz)2Cl]26.8g、配位子(Hppz)2.8g、炭酸カリウム9.1g、フェノール60gを200ml三口フラスコに入れ、窒素気流下、200℃で19時間加熱した。この反応混合物にメタノールを加えて超音波を照射し、吸引ろ過をして白色固体を得た。得られた固体を水、メタノールでさらに洗浄した。得られた固体を酢酸エチルにて再結晶することにより、[Ir(ppz)3]を収率80%で得た(白色粉末)。
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
116 電荷発生層
201 第1の電極
202(1) 第1のEL層
202(2) 第2のEL層
202(n−1) 第(n−1)のEL層
202(n) 第(n)のEL層
204 第2の電極
205 電荷発生層
205(1) 第1の電荷発生層
205(2) 第2の電荷発生層
205(n−2) 第(n−2)の電荷発生層
205(n−1) 第(n−1)の電荷発生層
301 素子基板
302 画素部
303 駆動回路部(ソース線駆動回路)
304a、304b 駆動回路部(ゲート線駆動回路)
305 シール材
306 封止基板
307 配線
308 FPC(フレキシブルプリントサーキット)
309 FET
310 FET
311 スイッチング用FET
312 電流制御用FET
313 第1の電極(陽極)
314 絶縁物
315 EL層
316 第2の電極(陰極)
317 発光素子
318 空間
351 基板
352 第1の電極
353 第2の電極
354 EL層
355 絶縁膜
356 隔壁
900 基板
901 第1の電極
902 EL層
903 第2の電極
911 正孔注入層
912 正孔輸送層
913 発光層
914 電子輸送層
915 電子注入層
2000 タッチパネル
2501 表示パネル
2502R 画素
2502t トランジスタ
2503c 容量素子
2503g 走査線駆動回路
2503t トランジスタ
2509 FPC
2510 基板
2511 配線
2519 端子
2521 絶縁層
2528 絶縁体
2550R 発光素子
2560 封止層
2567BM 遮光層
2567p 反射防止層
2567R 着色層
2570 基板
2590 基板
2591 電極
2592 電極
2593 絶縁層
2594 配線
2595 タッチセンサ
2597 接着層
2598 配線
2599 端子
2601 パルス電圧出力回路
2602 電流検出回路
2603 容量
2611 トランジスタ
2612 トランジスタ
2613 トランジスタ
2621 電極
2622 電極
4000 照明装置
4001 基板
4002 発光素子
4003 基板
4004 電極
4005 EL層
4006 電極
4007 電極
4008 電極
4009 補助配線
4010 絶縁層
4011 封止基板
4012 シール材
4013 乾燥剤
4015 拡散板
4100 照明装置
4200 照明装置
4201 基板
4202 発光素子
4204 電極
4205 EL層
4206 電極
4207 電極
4208 電極
4209 補助配線
4210 絶縁層
4211 封止基板
4212 シール材
4213 バリア膜
4214 平坦化膜
4215 拡散板
4300 照明装置
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
7302 筐体
7304 表示パネル
7305 時刻を表すアイコン
7306 その他のアイコン
7311 操作ボタン
7312 操作ボタン
7313 接続端子
7321 バンド
7322 留め金
7400 携帯電話機
7401 筐体
7402 表示部
7403 操作用ボタン
7404 外部接続部
7405 スピーカ
7406 マイク
7407 カメラ
7500(1)、7500(2) 筐体
7501(1)、7501(2) 第1面
7502(1)、7502(2) 第2面
8001 照明装置
8002 照明装置
8003 照明装置
8004 照明装置
9310 携帯情報端末
9311 表示パネル
9312 表示領域
9313 ヒンジ
9315 筐体
Claims (9)
- イリジウムと、前記イリジウムとシクロメタル化している複数の配位子とを有する有機金属イリジウム錯体であり、
前記複数の配位子は、いずれも前記イリジウムに配位する窒素原子を含む複素芳香環を有し、
前記有機金属イリジウム錯体のLC分析において、前記複数の配位子のうちの一つがモノクロロ化されてなる配位子を含む有機金属イリジウム錯体を不純物として検出したとき、
前記不純物は、PDA検出器による面積百分率法の定量において、0.1%以下であることを特徴とする有機金属イリジウム錯体。 - イリジウムと、前記イリジウムとシクロメタル化している複数の配位子とを有する有機金属イリジウム錯体であり、
前記複数の配位子は、いずれも前記イリジウムに配位する窒素原子を含む複素芳香環を有し、
前記有機金属イリジウム錯体のLC−MS分析において、前記有機金属イリジウム錯体の質量数+35±1となる質量電荷比として検出される不純物は、PDA検出器による面積百分率法の定量において、0.1%以下であることを特徴とする有機金属イリジウム錯体。 - 請求項1または請求項2に記載の有機金属イリジウム錯体を有する発光素子。
- 一対の電極間にEL層を有し、
前記EL層は、請求項1または請求項2に記載の有機金属イリジウム錯体を有する発光素子。 - 請求項3または請求項4に記載の発光素子と、
トランジスタ、または、基板と、
を有する発光装置。 - 請求項5に記載の発光装置と、
マイク、カメラ、操作用ボタン、外部接続部、または、スピーカと、
を有する電子機器。 - 請求項5に記載の発光装置と、
筐体、カバー、または、支持台を有する照明装置。 - イリジウムと塩素との原子数の割合が、イリジウム1に対し、塩素が3.1未満、2.5以上である塩化イリジウム水和物と、配位子とを用いることを特徴とする有機金属イリジウム錯体の合成方法。
- イリジウムと塩素との原子数の割合が、イリジウム1に対し、塩素が3.0未満、2.5以上である塩化イリジウム水和物と、配位子とを用いることを特徴とする有機金属イリジウム錯体の合成方法。
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JP6427681B2 (ja) * | 2016-01-29 | 2018-11-21 | 住友化学株式会社 | 組成物、燐光発光性化合物及び発光素子 |
CN110243523B (zh) * | 2019-07-12 | 2022-04-01 | 云谷(固安)科技有限公司 | 一种压力检测系统、压力检测方法及压力变化检测方法 |
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- 2015-10-27 US US14/924,114 patent/US20160118606A1/en not_active Abandoned
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2018
- 2018-09-20 US US16/136,590 patent/US20190036041A1/en not_active Abandoned
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JP2005220136A (ja) * | 2004-02-02 | 2005-08-18 | Samsung Sdi Co Ltd | イリジウム化合物及びそれを利用した有機電界発光素子 |
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WO2018061421A1 (ja) * | 2016-09-28 | 2018-04-05 | 住友化学株式会社 | 組成物及び発光素子 |
JPWO2018061421A1 (ja) * | 2016-09-28 | 2018-09-27 | 住友化学株式会社 | 組成物及び発光素子 |
CN109724235A (zh) * | 2017-10-30 | 2019-05-07 | 杭州三花微通道换热器有限公司 | 换热器、换热系统和空调器 |
Also Published As
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US20160118606A1 (en) | 2016-04-28 |
US20190036041A1 (en) | 2019-01-31 |
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