JP2017114853A - 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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- JP2017114853A JP2017114853A JP2016242518A JP2016242518A JP2017114853A JP 2017114853 A JP2017114853 A JP 2017114853A JP 2016242518 A JP2016242518 A JP 2016242518A JP 2016242518 A JP2016242518 A JP 2016242518A JP 2017114853 A JP2017114853 A JP 2017114853A
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- AFNRRBXCCXDRPS-UHFFFAOYSA-N tin(ii) sulfide Chemical compound [Sn]=S AFNRRBXCCXDRPS-UHFFFAOYSA-N 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
- 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
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- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
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- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- H—ELECTRICITY
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- 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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- 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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- 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
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- 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
- C07F15/004—Iridium compounds without a metal-carbon linkage
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- 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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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- 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
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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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
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- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
【解決手段】イリジウムとピラジン骨格の1位の窒素とが結合し、ピラジン骨格の2位及び3位にはアルキル基置換フェニル基が結合し、ピラジン骨格の5位にはシアノ基を置換フェニル基が結合し、ピラジン骨格の2位に結合しているフェニル基がイリジウムとオルトメタル化している構造を含む、式(100)に代表される有機金属錯体。
【選択図】なし
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。
一般式(G3)および一般式(G5)の合成に用いる、下記一般式(G0)で表されるピラジン誘導体は、以下のような3種類の合成スキーム(A1)、(A2)、(A3)で示す合成方法により合成することができる。
次に、一般式(G3)で表される有機金属錯体の合成方法を示す。まず、下記合成スキーム(B−1)に示すように、一般式(G0)で表されるピラジン誘導体と、ハロゲンを含むイリジウム化合物(塩化イリジウム、臭化イリジウム、ヨウ化イリジウムなど)と、を無溶媒、またはアルコール系溶媒(グリセロール、エチレングリコール、2−メトキシエタノール、2−エトキシエタノールなど)単独、あるいはアルコール系溶媒1種類以上と水との混合溶媒を用いて、不活性ガス雰囲気にて加熱することにより、ハロゲンで架橋された構造を有する有機金属錯体の一種であり、新規物質である複核錯体(B)を得ることができる。加熱手段として特に限定はなく、オイルバス、サンドバス、又はアルミブロック等を用いることができる。また、マイクロ波を加熱手段として用いることも可能である。
次に、一般式(G5)で表される有機金属錯体の合成方法を示す。合成スキーム(C)に示すように、ハロゲンを含むイリジウム化合物(塩化イリジウム水和物、臭化イリジウム、ヨウ化イリジウム、酢酸イリジウム、ヘキサクロロイリジウム酸アンモニウム等)、または有機イリジウム錯体化合物(アセチルアセトナト錯体、ジエチルスルフィド錯体、ジ−μ−クロロ架橋二核錯体、ジ−μ−ヒドロキソ架橋二核錯体等)と、一般式(G0)で表されるピラジン誘導体と、を混合した後、無溶媒、またはアルコール系溶媒(グリセロール、エチレングリコール、2−メトキシエタノール、2−エトキシエタノール等)に溶解させ、その後、加熱することにより、一般式(G5)で表され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。
本実施の形態においては、本発明の一態様の発光素子を有する表示装置として、反射型の液晶素子と、発光素子と、を有し、透過モードと反射モードの両方の表示を行うことのできる表示装置について、図15〜図17を用いて説明する。なお、このような表示装置は、ER−hybrid display(Emissive OLED and Reflective LC Hybrid display)とも呼ぶことができる。
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説明する。なお、本実施の形態で説明する発光素子は、実施の形態2で説明した発光素子と異なる構成を有する。従って、発光素子の素子構造およびその作製方法について図31(A)(B)を用いて説明する。但し、実施の形態2で説明した発光素子と共通する部分については、実施の形態2の説明を参照することとして、説明を省略する。
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、ビス{4,6−ジメチル−2−[5−(4−シアノ−2,6−ジメチルフェニル)−3−(3,5−ジメチルフェニル)−2−ピラジニル−κN]フェニル−κC}(2,2,6,6−テトラメチル−3,5−ヘプタンジオナト−κ2O,O’)イリジウム(III)(略称:[Ir(dmdppr−dmCP)2(dpm)])の合成方法について説明する。なお、[Ir(dmdppr−dmCP)2(dpm)]の構造を以下に示す。
まず、3,3’,5,5’−テトラメチルベンジル5.27gとグリシンアミド塩酸塩2.61g、水酸化ナトリウム1.92g、メタノール50mLを、還流管を付けた三口フラスコに入れ、フラスコ内部を窒素置換した。その後、これを80℃で7時間撹拌することで反応させた。ここに12M塩酸2.5mLを加え30分撹拌した後、炭酸水素カリウム2.02gを加え、30分撹拌した。この懸濁液を吸引ろ過した後、得られた固体を水、メタノールで洗浄することにより、目的のピラジン誘導体を得た(乳白色粉末、収率79%)。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で得た5−ヒドロキシ−2,3−(3,5−ジメチルフェニル)ピラジン4.80gとトリエチルアミン4.5mL、脱水ジクロロメタン80mLを三口フラスコに入れ、内部を窒素置換した。このフラスコを−20℃に冷却した後、トリフルオロメタンスルホン酸無水物3.5mLを滴下し、室温で17時間半攪拌した。その後、フラスコを0℃に冷却した後、更にトリフルオロメタンスルホン酸無水物0.7mLを滴下し、室温で22時間攪拌して反応させた。反応溶液に水50mL、1M塩酸5mLを加え、ジクロロメタンを加えて、反応溶液中に含まれる物質をジクロロメタン中に抽出させた。このジクロロメタンに飽和炭酸水素ナトリウム水溶液および飽和食塩水を加えて洗浄し、硫酸マグネシウムを加えて乾燥させた。乾燥後にこの溶液をろ過し、ろ液を濃縮して得られた残渣を、トルエン:ヘキサン=1:1(体積比)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、目的のピラジン誘導体を得た(黄色オイル、収率96%)。ステップ2の合成スキームを下記(a−2)に示す。
次に、上記ステップ2で得た5,6−ビス(3,5−ジメチルフェニル)ピラジン−2−イルトリフルオロメタンスルホン酸2.05g、4−シアノ−2,6−ジメチルフェニルボロン酸1.00g、リン酸三カリウム3.81g、トルエン40mL、水4mLを三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌することで脱気した後、トリス(ジベンジリデンアセトン)ジパラジウム(0)0.044g、トリス(2,6−ジメトキシフェニル)ホスフィン0.084gを加え、7時間還流した。反応溶液に水を加え、トルエンを加えて、反応溶液中に含まれる物質をトルエン中に抽出させた。このトルエンに飽和食塩水を加えて洗浄し、硫酸マグネシウムを加えて乾燥させた。乾燥後、この溶液をろ過し、ろ液を濃縮して得られた残渣を、ヘキサン:酢酸エチル=5:1(体積比)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、目的のピラジン誘導体Hdmdppr−dmCPを得た(白色粉末、収率90%)。ステップ3の合成スキームを下記(a−3)に示す。
次に、2−エトキシエタノール15mLと水5mL、上記ステップ3で得たHdmdppr−dmCP(略称)1.74g、塩化イリジウム水和物(IrCl3・H2O)(フルヤ金属社製)0.60g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1時間照射し、反応させた。溶媒を留去した後、得られた残渣をヘキサンで吸引ろ過、洗浄し、複核錯体[Ir(dmdppr−dmCP)2Cl]2を得た(褐色粉末、収率89%)。また、ステップ4の合成スキームを下記(a−4)に示す。
さらに、2−エトキシエタノール30mL、上記ステップ4で得た複核錯体[Ir(dmdppr−dmCP)2Cl]2 0.96g、ジピバロイルメタン(略称:Hdpm)0.26g、炭酸ナトリウム0.48g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、Hdpm0.13gを加え、反応容器にマイクロ波(2.45GHz 120W)を60分間照射することで反応させた。溶媒を留去し、得られた残渣を、ジクロロメタン:ヘキサン=1:1(体積比)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た。更に、ジクロロメタン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た後、ジクロロメタンとメタノールの混合溶媒にて再結晶することにより、本発明の一態様である有機金属錯体、[Ir(dmdppr−dmCP)2(dpm)]を赤色粉末として得た(収率37%)。得られた赤色粉末固体0.39gを、トレインサブリメーション法により昇華精製した。昇華精製条件は、圧力2.6Pa、アルゴンガスを流量5mL/minで流しながら、300℃で固体を加熱した。昇華精製後、目的物の赤色固体を収率85%で得た。ステップ5の合成スキームを下記(a−5)に示す。
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70nmとし、電極面積は2mm×2mmとした。
作製した発光素子1、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、実施の形態1の構造式(108)で表される本発明の一態様である有機金属錯体、ビス{4,6−ジメチル−2−[5−(5−シアノ−2−メチルフェニル)−3−(3,5−ジメチルフェニル)−2−ピラジニル−κN]フェニル−κC}(2,2,6,6−テトラメチル−3,5−ヘプタンジオナト−κ2O,O’)イリジウム(III)(略称:[Ir(dmdppr−m5CP)2(dpm)])の合成方法について説明する。なお、[Ir(dmdppr−m5CP)2(dpm)]の構造を以下に示す。
まず、5,6−ビス(3,5−ジメチルフェニル)ピラジン−2−イルトリフルオロメタンスルホン酸1.83g、5−シアノ−2−メチルフェニルボロン酸0.79g、リン酸三カリウム3.17g、トルエン33mL、水3.3mLを三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌することで脱気した後、トリス(ジベンジリデンアセトン)ジパラジウム(0)0.038g、トリス(2,6−ジメトキシフェニル)ホスフィン0.075gを加え、8時間還流した。反応後、トルエンによる抽出を行った。その後、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、目的のピラジン誘導体、Hdmdppr−m5CP(略称)を得た(白色固体、収率96%)。ステップ1の合成スキームを下記(b−1)に示す。
次に、2−エトキシエタノール15mLと水5mL、上記ステップ1で得たHdmdppr−m5CP(略称)1.59g、塩化イリジウム水和物(IrCl3・H2O)(フルヤ金属社製)0.57g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1時間照射し、反応させた。溶媒を留去した後、得られた残渣をメタノールで吸引ろ過、洗浄し、複核錯体、[Ir(dmdppr−m5CP)2Cl]2 を得た(赤褐色固体、収率66%)。ステップ2の合成スキームを下記(b−2)に示す。
さらに、2−エトキシエタノール20mL、上記ステップ2で得た複核錯体[Ir(dmdppr−m5CP)2Cl]2 0.65g、ジピバロイルメタン(略称:Hdpm)0.25g、炭酸ナトリウム0.33g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2時間照射した。得られた反応溶液を吸引ろ過した後、ろ物を水、メタノールで洗浄した。
本実施例では、実施の形態1の構造式(114)で表される本発明の一態様である有機金属錯体、ビス{4,6−ジメチル−2−[5−(2−シアノ−6−メチルフェニル)−3−(3,5−ジメチルフェニル)−2−ピラジニル−κN]フェニル−κC}(2,2,6,6−テトラメチル−3,5−ヘプタンジオナト−κ2O,O’)イリジウム(III)(略称:[Ir(dmdppr−m2CP)2(dpm)])の合成方法について説明する。なお、[Ir(dmdppr−m2CP)2(dpm)]の構造を以下に示す。
まず、5,6−ビス(3,5−ジメチルフェニル)ピラジン−2−イルトリフルオロメタンスルホン酸1.40g、3−メチル−2−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)ベンゾニトリル0.98g、リン酸三カリウム2.48g、トルエン26mL、水2.6mLを三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌することで脱気した後、トリス(ジベンジリデンアセトン)ジパラジウム(0)0.029g、トリス(2,6−ジメトキシフェニル)ホスフィン0.058gを加え、7時間半還流した。反応後、トルエンによる抽出を行った。その後、ヘキサン:酢酸エチル=5:1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、目的のピラジン誘導体Hdmdppr−m2CP(略称)を得た(白色固体、収率85%)。ステップ1の合成スキームを下記(c−1)に示す。
次に、2−エトキシエタノール15mLと水5mL、上記ステップ1で得たHdmdppr−m2CP(略称)1.08g、塩化イリジウム水和物(IrCl3・H2O)(フルヤ金属社製)0.39g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1時間照射し、反応させた。得られた反応溶液を吸引ろ過し、ろ物をメタノールで洗浄し、複核錯体[Ir(dmdppr−m2CP)2Cl]2 (略称)を得た(橙色固体、収率44%)。ステップ2の合成スキームを下記(c−2)に示す。
さらに、2−エトキシエタノール20mL、上記ステップ2で得た複核錯体[Ir(dmdppr−m5CP)2Cl]2(略称)0.59g、ジピバロイルメタン(略称:Hdpm)0.22g、炭酸ナトリウム0.31g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2時間照射した。反応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することにより、本発明の有機金属錯体[Ir(dmdppr−m2CP)2(dpm)](略称)を深赤色粉末として得た(収率10%)。ステップ3の合成スキームを下記(c−3)に示す。
作製した各発光素子(発光素子4、発光素子5、および比較発光素子6)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。また、結果を図36〜図40に示す。
本参考合成例では、実施例5において比較発光素子6に用いた有機金属錯体、ビス{4,6−ジメチル−2−[5−(2,5−ジメチルフェニル)−3−(3,5−ジメチルフェニル)−2−ピラジニル−κN]フェニル−κC}(2,2,6,6−テトラメチル−3,5−ヘプタンジオナト−κ2O,O’)イリジウム(III)(略称:[Ir(dmdppr−25dmp)2(dpm)])の合成方法について説明する。なお、[Ir(dmdppr−25dmp)2(dpm)]の構造を以下に示す。
まず、3,3’,5,5’−テトラメチルベンジル5.27gとグリシンアミド塩酸塩2.61g、水酸化ナトリウム1.92g、メタノール50mLを、還流管を付けた三口フラスコに入れ、フラスコ内部を窒素置換した。その後、これを80℃で7時間撹拌することで反応させた。ここに12M塩酸2.5mLを加え30分撹拌した後、炭酸水素カリウム2.02gを加え、30分撹拌した。この懸濁液を吸引ろ過した後、得られた固体を水、メタノールで洗浄することにより、目的のピラジン誘導体を得た(乳白色粉末、収率79%)。ステップ1の合成スキームを下記(d−1)に示す。
次に、上記ステップ1で得た5−ヒドロキシ−2,3−(3,5−ジメチルフェニル)ピラジン4.80gとトリエチルアミン4.5mL、dryジクロロメタン80mLを三口フラスコに入れ、内部を窒素置換した。このフラスコを−20℃に冷却した後、トリフルオロメタンスルホン酸無水物3.5mLを滴下し、室温で17時間半攪拌した。ここで、フラスコを0℃に冷却した後、更にトリフルオロメタンスルホン酸無水物0.7mLを滴下し、室温で22時間攪拌し反応させた。反応溶液に水、1M塩酸5mLを加え、ジクロロメタンで有機層を抽出した。得られた抽出液を飽和炭酸水素ナトリウム水溶液、飽和食塩水で洗浄し、硫酸マグネシウムで乾燥した。乾燥した後の溶液をろ過した。このろ液を濃縮し、得られた残渣を、トルエン:ヘキサン=1:1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、目的のピラジン誘導体を得た(黄色オイル、収率96%)。ステップ2の合成スキームを下記(d−2)に示す。
次に、上記ステップ2で得た5,6−ビス(3,5−ジメチルフェニル)ピラジン−2−イルトリフルオロメタンスルホン酸1.22g、2,5−ジメチルフェニルボロン酸0.51g、リン酸三カリウム2.12g、トルエン20mL、水2mLを三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌することで脱気した後、トリス(ジベンジリデンアセトン)ジパラジウム(0)0.026g、トリス(2,6−ジメトキシフェニル)ホスフィン0.053gを加え、4時間還流した。反応溶液に水を加え、トルエンにて有機層を抽出した。得られた抽出液を飽和食塩水で洗浄し、硫酸マグネシウムで乾燥した。乾燥した後の溶液をろ過した。このろ液を濃縮し、得られた残渣を、トルエン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、目的のピラジン誘導体Hdmdppr−25dmpを得た(無色オイル、収率97%)。ステップ3の合成スキームを下記(d−3)に示す。
次に、2−エトキシエタノール15mLと水5mL、上記ステップ3で得たHdmdppr−25dmp1.04g、塩化イリジウム水和物(IrCl3・H2O)(フルヤ金属社製)0.36g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1時間照射し、反応させた。溶媒を留去した後、得られた残渣をメタノールで吸引ろ過、洗浄し、複核錯体[Ir(dmdppr−25dmp)2Cl]2を得た(赤褐色粉末、収率80%)。また、ステップ4の合成スキームを下記(d−4)に示す。
さらに、2−エトキシエタノール30mL、上記ステップ4で得た複核錯体[Ir(dmdppr−25dmp)2Cl]2 1.58g、ジピバロイルメタン(略称:Hdpm)0.44g、炭酸ナトリウム0.84g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分間照射することで加熱した。溶媒を留去し、得られた残渣をメタノールで吸引ろ過した。得られた固体を水、メタノールで洗浄した。得られた固体を、ジクロロメタン:ヘキサン=1:1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により精製した後、ジクロロメタンとメタノールの混合溶媒にて再結晶することにより、有機金属錯体[Ir(dmdppr−25dmp)2(dpm)]を赤色粉末として得た(収率71%)。得られた赤色粉末固体1.27gを、トレインサブリメーション法により昇華精製した。昇華精製条件は、圧力2.6Pa、アルゴンガスを流量5mL/minで流しながら、250℃で固体を加熱した。昇華精製後、目的物の赤色固体を収率92%で得た。ステップ5の合成スキームを下記(d−5)に示す。
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
500 表示装置
503 表示部
504 画素
505 導電膜
506 位置
507 開口部
510 液晶素子
511 発光素子
515 トランジスタ
516 トランジスタ
517 トランジスタ
518 端子部
519 端子部
521 基板
522 基板
523 発光素子
524 液晶素子
525 絶縁層
528 着色層
529 接着層
530 導電層
531 EL層
532 導電層
533 開口部
534 着色層
535 遮光層
536 構造体
537 導電層
538 液晶
539 導電層
540 配向膜
541 配向膜
542 接着層
543 導電層
544 FPC
545 接続層
546 絶縁層
547 接続部
548 接続体
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
3200 基板
3201 陰極
3202 EL層
3203 陽極
3213 発光層
3214 電子注入層
3215 正孔輸送層
3216 正孔注入層
3217 絶縁物
3300 ヘッド部
3301a 噴射部
3301c 噴射部
3302a 圧電素子
3302c 圧電素子
3303a インク
3303c インク
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 (21)
- 一般式(G1)で表される構造を含む有機金属錯体。
(一般式(G1)中、A1〜A4は、それぞれ独立に、置換もしくは無置換の炭素数1〜6のアルキル基を表し、R1〜R6は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基のいずれかを表す。また、R7〜R11は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基、シアノ基のいずれかを表し、少なくとも一は、シアノ基を表す。) - 一般式(G2)で表される構造を含む有機金属錯体。
(一般式(G2)中、A1〜A4は、それぞれ独立に、置換もしくは無置換の炭素数1〜6のアルキル基を表し、R6は、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基のいずれかを表す。また、R7〜R11は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基、シアノ基のいずれかを表し、少なくとも一は、シアノ基を表す。) - 一般式(G3)で表される有機金属錯体。
(一般式(G3)中、A1〜A4は、それぞれ独立に、置換もしくは無置換の炭素数1〜6のアルキル基を表し、R1〜R6は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基のいずれかを表す。また、R7〜R11は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基、シアノ基のいずれかを表し、少なくとも一は、シアノ基を表す。Lは、モノアニオン性の配位子を表す。) - 一般式(G4)で表される有機金属錯体。
(一般式(G4)中、A1〜A4は、それぞれ独立に、置換もしくは無置換の炭素数1〜6のアルキル基を表し、R6は、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基のいずれかを表す。また、R7〜R11は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基、シアノ基のいずれかを表し、少なくとも一は、シアノ基を表す。Lは、モノアニオン性の配位子を表す。) - 請求項3または請求項4において、
前記モノアニオン性の配位子は、β−ジケトン構造を有するモノアニオン性の二座キレート配位子、カルボキシル基を有するモノアニオン性の二座キレート配位子、フェノール性水酸基を有するモノアニオン性の二座キレート配位子、又は二つの配位元素がいずれも窒素であるモノアニオン性の二座キレート配位子、又はシクロメタル化によりイリジウムと金属−炭素結合を形成する芳香族複素環二座配位子である有機金属錯体。 - 請求項3または請求項4において、
前記モノアニオン性の配位子は、下記一般式(L1)〜(L6)のいずれか一である有機金属錯体。
(式中、R71〜R94は、それぞれ独立に水素又は置換もしくは無置換の炭素数1〜6のアルキル基、ハロゲン基、ビニル基、置換もしくは無置換の炭素数1〜6のハロアルキル基、置換もしくは無置換の炭素数1〜6のアルコキシ基、又は置換もしくは無置換の炭素数1〜6のアルキルチオ基を表す。また、A1〜A3は、それぞれ独立に窒素、または水素と結合するsp2混成炭素、又は置換基を有するsp2混成炭素を表し、前記置換基は炭素数1〜6のアルキル基、ハロゲン基、炭素数1〜6のハロアルキル基、又はフェニル基を表し、B1〜B8は、それぞれ独立に窒素、または置換もしくは無置換の炭素を表し、前記置換基は炭素数1〜6のアルキル基、ハロゲン基、炭素数1〜6のハロアルキル基、又はフェニル基を表す。) - 一般式(G5)で表される有機金属錯体。
(一般式(G5)中、A1〜A4は、それぞれ独立に、置換もしくは無置換の炭素数1〜6のアルキル基を表し、R1〜R6は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基のいずれかを表す。また、R7〜R11は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基、シアノ基のいずれかを表し、少なくとも一は、シアノ基を表す。) - 一般式(G6)で表される有機金属錯体。
(一般式(G6)中、A1〜A4は、それぞれ独立に、置換もしくは無置換の炭素数1〜6のアルキル基を表し、R6は、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基のいずれかを表す。また、R7〜R11は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基、シアノ基のいずれかを表し、少なくとも一は、シアノ基を表す。) - 一般式(G7)で表される有機金属錯体。
(一般式(G7)中、A1〜A4は、それぞれ独立に、置換もしくは無置換の炭素数1〜6のアルキル基を表し、R1〜R6は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基のいずれかを表す。また、R7〜R11は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基、シアノ基のいずれかを表し、少なくとも一は、シアノ基を表す。) - 一般式(G8)で表される有機金属錯体。
(一般式(G8)中、A1〜A4は、それぞれ独立に、置換もしくは無置換の炭素数1〜6のアルキル基を表し、R6は、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基のいずれかを表す。また、R7〜R11は、それぞれ独立に、水素、置換もしくは無置換の炭素数1〜6のアルキル基、置換もしくは無置換の炭素数6〜13のアリール基、置換もしくは無置換の炭素数3〜12のヘテロアリール基、シアノ基のいずれかを表し、少なくとも一は、シアノ基を表す。) - 請求項1乃至請求項10のいずれかに記載の有機金属錯体において、R7〜R11の少なくとも一が、炭素数1〜6のアルキル基である有機金属錯体。
- 請求項1乃至請求項10のいずれかに記載の有機金属錯体において、R7またはR11の少なくとも一が、炭素数1〜6のアルキル基である有機金属錯体。
- 下記構造式(100)で表される有機金属錯体。
- 請求項1乃至請求項13のいずれか一に記載の有機金属錯体を用いた発光素子。
- 一対の電極間にEL層を有し、
前記EL層は、請求項1乃至請求項13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EL層を有し、
前記EL層は、発光層を有し、
前記発光層は、請求項1乃至請求項13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EL層を有し、
前記EL層は、発光層を有し、
前記発光層は、複数の有機化合物を有し、
前記複数の有機化合物のうち一は、
請求項1乃至請求項13のいずれか一に記載の有機金属錯体である発光素子。 - 請求項14乃至請求項17のいずれか一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18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18に記載の発光装置と、
筐体またはタッチセンサ機能と、
を有する電子機器。 - 請求項18に記載の発光装置と、
筐体、カバー、または、支持台と、
を有する照明装置。
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US9960371B2 (en) | 2018-05-01 |
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