JP6935176B2 - 有機金属錯体、発光素子、発光装置、電子機器、および照明装置 - Google Patents
有機金属錯体、発光素子、発光装置、電子機器、および照明装置 Download PDFInfo
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- JP6935176B2 JP6935176B2 JP2016165408A JP2016165408A JP6935176B2 JP 6935176 B2 JP6935176 B2 JP 6935176B2 JP 2016165408 A JP2016165408 A JP 2016165408A JP 2016165408 A JP2016165408 A JP 2016165408A JP 6935176 B2 JP6935176 B2 JP 6935176B2
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- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 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
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-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
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
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- 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
- C07F15/0086—Platinum 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
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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
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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
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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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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- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Description
本実施の形態では、本発明の一態様である有機金属錯体について説明する。
下記一般式(G0)で表されるピリドインドール誘導体は、以下のような簡便な合成方法により合成することができる。
次に、下記合成スキーム(A−2)に示すように、上記一般式(G0)で表されるピリドインドール誘導体と、ハロゲンを含む白金の金属化合物(テトラクロロ白金酸カリウム等)とを、酢酸または酢酸を含む溶媒を用いて、不活性ガス雰囲気にて加熱する。これにより、一般式(G1)で表される本発明の一態様である有機金属錯体が得られる。
本実施の形態では、本発明の一態様である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り、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や自動車の一例について、説明する。
本実施の形態では、本発明の一態様である発光素子を適用して作製される照明装置の構成について図8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9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10〜図14を用いて説明を行う。
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、{2−[9’−(1,2−フェニレン−κC2)(9,2’−ビ−9H−ピリド[2,3−b]インドール−1,1’−ジイル−κN1,κN1’)]−1,2−フェニレン−κC1}白金(II)(略称:[Pt(pidrpy2)])の合成方法について説明する。なお、[Pt(pidrpy2)]の構造を以下に示す。
まず、2−ヨードフェニルアセトアミド18.94gと2,6−ジクロロピリジン−3−ボロン酸20.73g、トリフェニルホスフィン1.18g、酢酸パラジウム0.49g、トリエチルアミン30mL,dryDMF290mLを、還流管を付けた三口フラスコに入れ、フラスコ内を窒素置換した。その後、100℃で6時間撹拌した。この反応溶液に水を加え、酢酸エチルにて有機層を抽出した。得られた有機層を飽和食塩水で洗浄し、硫酸マグネシウムにて乾燥した後、ヘキサン:酢酸エチル=2:1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で精製し、目的物を得た(黄白色粉末、収率68%)。ステップ1の合成スキームを下記式(a−1)に示す。
次に、上記ステップ1で得たN−[2−(2,6−ジクロロ−3−ピリジニル)フェニル]アセトアミド14.22gと炭酸カリウム41.43g、dryDMF250mLを、還流管を付けたナスフラスコに入れ、フラスコ内を窒素置換した。ここに水素化ナトリウム(60% in mineral oil)4.02gを加え、100℃で7時間撹拌した。得られた反応溶液を水1Lに注ぎ、析出した固体を吸引ろ過し、エタノールで洗浄することで、目的物を得た(クリーム色粉末、収率75%)。ステップ2の合成スキームを下記式(a−2)に示す。
次に、上記ステップ2で得た2−クロロ−9H−ピリド[2,3−b]インドール0.50gとヨードベンゼン0.42mL、リン酸三カリウム1.39g、trans−1,2−シクロヘキサンジアミン0.037g、ヨウ化銅0.030g、dryジオキサン15mLを、還流管を付けたナスフラスコに入れ、フラスコ内を窒素置換した。110℃で30時間半撹拌した後、得られた混合物を、ジクロロメタンを用いて吸引ろ過した。この溶液の溶媒を留去した後、得られた残渣を、ヘキサン:酢酸エチル=5:1を展開溶媒とするフラッシュカラムクロマトグラフィーで精製し、目的物を得た(白色粉末、収率68%)。また、ステップ3の合成スキームを下記式(a−3)に示す。
次に、上記ステップ2で得た2−クロロ−9H−ピリド[2,3−b]インドール0.50gとフェニルボロン酸0.61g、炭酸ナトリウム0.53g、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド(略称:Pd(PPh3)2Cl2)0.021g、DMF10mL、水10mLを、還流管のついたナスフラスコに入れ、フラスコ内をアルゴン置換した。この反応容器にマイクロ波(2.45GHz 100W)を2時間照射することで加熱した。
次に、上記ステップ3で得た2−クロロ−9−フェニル−9H−ピリド[2,3−b]インドール0.48gと上記ステップ4で得た2−フェニル−9H−ピリド[2,3−b]インドール0.42g、ナトリウムtert−ブトキシド0.49g、メシチレン9mLを、還流管のついたナスフラスコに入れ、フラスコ内を窒素置換した。フラスコ内を減圧下で撹拌することで脱気した後、2−ジシクロヘキシルホスフィノ−2’−6’−ジメトキシビフェニル(略称:S−Phos)0.028g、ビス(ジベンジリデンアセトン)パラジウム(0)(略称:Pd(dba)2)0.020gを加え、130℃で16時間撹拌した。
さらに、上記ステップ5で得たHpidrpy2、0.53gとテトラクロリド白金(II)酸カリウム0.50g、テトラブチルアンモニウムブロミド0.035g、氷酢酸70mLを、還流管のついたナスフラスコに入れ、フラスコ内を窒素置換した。窒素バブリングを30分間した後、室温で23時間、120℃で24時間撹拌した。
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(ITO)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および発光素子2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。
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
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
312 電流制御用FET
313a、313b 第1の電極(陽極)
314 絶縁物
315 EL層
316 第2の電極(陰極)
317a、317b 発光素子
318 空間
320a、320b 導電膜
321、322 領域
323 引き回し配線
324 有色層(カラーフィルタ)
325 黒色層(ブラックマトリクス)
326、327、328 FET
401 基板
402 第1の電極
403a、403b、403c EL層
404 第2の電極
405 発光素子
406 絶縁膜
407 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
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
5101 ライト
5102 ホイール
5103 ドア
5104 表示部
5105 ハンドル
5106 シフトレバー
5107 座席シート
5108 インナーリアビューミラー
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 表示部
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
9310 携帯情報端末
9311 表示部
9312 表示領域
9313 ヒンジ
9315 筐体
Claims (9)
- 請求項1乃至請求項3のいずれか一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3のいずれか一に記載の有機金属錯体を有する発光素子。 - 請求項4又は請求項5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6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6に記載の発光装置と、
筐体またはタッチセンサと、
を有する電子機器。 - 請求項4又は請求項5に記載の発光素子と、
筐体、カバー、または、支持台と、
を有する照明装置。
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JP6847589B2 (ja) | 2015-05-20 | 2021-03-24 | 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、および照明装置 |
KR102501466B1 (ko) * | 2017-04-21 | 2023-02-20 | 삼성전자주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물 |
CN109427817B (zh) * | 2017-08-30 | 2020-09-15 | 瀚宇彩晶股份有限公司 | 薄膜晶体管基板以及显示器 |
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US6267601B1 (en) * | 1997-12-05 | 2001-07-31 | The Psychological Corporation | Computerized system and method for teaching and assessing the holistic scoring of open-ended questions |
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JP4628108B2 (ja) | 2003-02-14 | 2011-02-09 | 株式会社半導体エネルギー研究所 | 有機金属錯体、及び電界発光素子を有する電子機器 |
JP2009023938A (ja) | 2007-07-19 | 2009-02-05 | Showa Denko Kk | イリジウム錯体化合物、有機エレクトロルミネッセンス素子およびその用途 |
JP2009224762A (ja) | 2008-02-18 | 2009-10-01 | Fujifilm Corp | 有機電界発光素子 |
WO2011121955A1 (ja) * | 2010-03-30 | 2011-10-06 | パナソニック株式会社 | オーディオ装置 |
TWI541247B (zh) | 2011-02-18 | 2016-07-11 | 美國亞利桑那州立大學董事會 | 具有幾何失真電荷轉移態之四配位鉑及鈀錯合物及彼等於發光裝置中之應用 |
TWI529238B (zh) * | 2011-04-15 | 2016-04-11 | 半導體能源研究所股份有限公司 | 有機發光元件、有機金屬錯合物發光裝置、電子用具及照明裝置 |
US9238668B2 (en) * | 2011-05-26 | 2016-01-19 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Synthesis of platinum and palladium complexes as narrow-band phosphorescent emitters for full color displays |
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JP6117618B2 (ja) * | 2012-06-01 | 2017-04-19 | 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 |
JP6234100B2 (ja) | 2012-07-31 | 2017-11-22 | 株式会社半導体エネルギー研究所 | 発光素子、複素環化合物、ディスプレイモジュール、照明モジュール、発光装置、表示装置、照明装置及び電子機器 |
KR102238075B1 (ko) | 2013-05-03 | 2021-04-07 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 복소환 화합물, 발광 소자, 디스플레이 모듈, 조명 모듈, 발광 장치, 표시 장치, 조명 장치, 및 전자 기기 |
KR102265675B1 (ko) * | 2013-05-20 | 2021-06-15 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 금속 착체, 발광 소자, 발광 장치, 전자기기, 및 조명 장치 |
KR102349659B1 (ko) | 2013-06-10 | 2022-01-11 | 아리조나 보드 오브 리젠츠 온 비하프 오브 아리조나 스테이트 유니버시티 | 개질된 방출 스펙트럼을 갖는 인광성 네자리 금속 착물 |
JP6804823B2 (ja) * | 2013-10-14 | 2020-12-23 | アリゾナ・ボード・オブ・リージェンツ・オン・ビハーフ・オブ・アリゾナ・ステイト・ユニバーシティーArizona Board of Regents on behalf of Arizona State University | 白金錯体およびデバイス |
CN104447880A (zh) * | 2014-12-11 | 2015-03-25 | 石家庄诚志永华显示材料有限公司 | 氮杂咔唑类oled磷光材料及其制备方法与应用 |
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