JP6598513B2 - 有機金属イリジウム錯体、発光素子、発光装置、電子機器、および照明装置 - Google Patents
有機金属イリジウム錯体、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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- JP6598513B2 JP6598513B2 JP2015107139A JP2015107139A JP6598513B2 JP 6598513 B2 JP6598513 B2 JP 6598513B2 JP 2015107139 A JP2015107139 A JP 2015107139A JP 2015107139 A JP2015107139 A JP 2015107139A JP 6598513 B2 JP6598513 B2 JP 6598513B2
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- KUGSVDXBPQUXKX-UHFFFAOYSA-N n-[9,10-bis(2-phenylphenyl)anthracen-2-yl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C(=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 KUGSVDXBPQUXKX-UHFFFAOYSA-N 0.000 description 1
- COVCYOMDZRYBNM-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N1C2=CC=C(N(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 COVCYOMDZRYBNM-UHFFFAOYSA-N 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000005381 potential energy Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229960000286 proflavine Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- HKCRVXUAKWXBLE-UHFFFAOYSA-N terbium(3+) Chemical compound [Tb+3] HKCRVXUAKWXBLE-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000012780 transparent material Substances 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
- 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229960001296 zinc oxide Drugs 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
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
- H10K85/30—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
-
- 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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- 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
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- 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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- Engineering & Computer Science (AREA)
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- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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。
一般式(G2)において、Lは、モノアニオン性の配位子を表す。
まず、下記合成スキーム(A−1)に示すように、構造式(G0)で表されるピリミジン誘導体と、ハロゲンを含む金属化合物(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(P)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を用いてもよい。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。
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材料として用いることができる発光素子の一態様について図1を用いて説明する。
フェニル)ベンズオキサゾラト]亜鉛(略称:Zn(BOX)2)、ビス[2−(2−ヒドロキシフェニル)ベンゾチアゾラト]亜鉛(略称:Zn(BTZ)2)などの金属錯体を用いることができる。また、2−(4−ビフェニリル)−5−(4−tert−ブチルフェニル)−1,3,4−オキサジアゾール(略称:PBD)、1,3−ビス[5−(p−tert−ブチルフェニル)−1,3,4−オキサジアゾール−2−イル]ベンゼン(略称:OXD−7)、3−(4’−tert−ブチルフェニル)−4−フェニル−5−(4’’−ビフェニル)−1,2,4−トリアゾール(略称:TAZ)、3−(4−tert−ブチルフェニル)−4−(4−エチルフェニル)−5−(4−ビフェニリル)−1,2,4−トリアゾール(略称:p−EtTAZ)、バソフェナントロリン(略称:BPhen)、バソキュプロイン(略称:BCP)、4,4’−ビス(5−メチルベンゾオキサゾール−2−イル)スチルベン(略称:BzOs)などの複素芳香族化合物も用いることができる。また、ポリ(2,5−ピリジンジイル)(略称:PPy)、ポリ[(9,9−ジヘキシルフルオレン−2,7−ジイル)−co−(ピリジン−3,5−ジイル)](略称:PF−Py)、ポリ[(9,9−ジオクチルフルオレン−2,7−ジイル)−co−(2,2’−ビピリジン−6,6’−ジイル)](略称:PF−BPy)のような高分子化合物を用いることもできる。ここに述べた物質は、主に1×10−6cm2/Vs以上の電子移動度を有する物質である。なお、正孔よりも電子の輸送性の高い物質であれば、上記以外の物質を電子輸送層114として用いてもよい。
本実施の形態では、本発明の一態様として、有機金属イリジウム錯体に加え、他の2種類以上の有機化合物を発光層に用いた発光素子について説明する。
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、実施の形態2や実施の形態3で説明した発光素子に着色層(カラーフィルタ等)を組み合わせる場合の発光装置の一態様について説明する。なお、本実施の形態では、発光装置の画素部の構成について図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装置を適用した照明装置の一例について、図6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イリジウム錯体、ビス[2−(5−フェニル−2−ピリミジニル−κN)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(5dppm2)2(acac)])の合成方法について説明する。なお、[Ir(5dppm2)2(acac)]の構造を以下に示す。
まず、5−ブロモ−2−クロロピリミジン5.0g(26mmol)、フェニルボロン酸7.0g(57mmol)、リン酸三カリウム12g(57mmol)、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(S−Phos)0.79g(1.9mmol)、トルエン250mLを500mL三口フラスコに入れ、フラスコ内を窒素置換した。この混合物に酢酸パラジウム(II)174mg(0.77mmol)加え、80℃で11時間、100℃で8時間撹拌した。所定時間経過後、この混合溶液に酢酸パラジウム(II)319mg(1.42mmol)、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(S−Phos)1.2g(2.8mmol)をさらに加え、100℃で8時間加熱撹拌した。得られた反応混合物に水を加え、水層をトルエンで抽出した。得られた抽出溶液と有機層を合わせて飽和食塩水で洗浄し、無水硫酸マグネシウムを加えて乾燥させた。この混合物を自然ろ過し、ろ液を濃縮して固体を得た。この固体をトルエンに溶解し、ろ紙上にセライト・アルミナ・フロリジールの順に積層してろ過した。得られたろ液を濃縮して得た固体を、トルエンにて再結晶して2,5−ジフェニルピリミジンを得た(白色固体、収率50%)。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で得られた配位子H5dppm2 1.8g(8.1mmol)、塩化イリジウム(III)水和物1.2g(3.8mmol)、2−エトキシエタノール15mL、水5mLを50mLナス型フラスコに入れ、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を、100℃、100Wの条件で1時間照射させることによって加熱し、反応させた。所定時間経過後、得られた反応溶液を濃縮し、残渣をエタノールで洗浄して複核錯体[Ir(5dppm2)2Cl]2を得た(橙色粉末、収率97%)。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で得られた複核錯体[Ir(5dppm2)2Cl]22.5g(1.8mmol)、炭酸ナトリウム1.9g(18mmol)、アセチルアセトン0.55g(5.5mmol)、2−エトキシエタノール40mLを100mL丸底フラスコに入れ、フラスコ内をアルゴン置換した。この反応容器に、110℃、120Wの条件で1時間マイクロ波を照射することによって反応させた。所定時間経過後、得られた反応混合物に水を加え、水層をジクロロメタンで抽出した。得られた抽出溶液を飽和食塩水で洗浄し、有機層に無水硫酸マグネシウムを加えて乾燥させた。得られた混合物を自然ろ過してろ液を得た。このろ液を濃縮して得た固体を、ジクロロメタンに溶解し、アルミナを通してろ過した。得られたろ液を濃縮して、残渣をジクロロメタンとヘキサンの混合溶媒にて再結晶して、本発明の一様態である有機金属錯体[Ir(5dppm2)2(acac)]を得た(橙色粉末、収率30%)。ステップ3の合成スキームを下記(a−3)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(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および比較発光素子2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。
図16は、本実施例で説明する発光素子3〜6の積層構造を示すものであるが、発光素子3は赤色発光を示し、発光素子4は緑色発光を示し、発光素子5は青色発光を示し、発光素子6が黄色発光を示すという構成であるため、それぞれの発光色が得られるように光学調整がなされている。具体的には、第1の電極4001と第1の正孔注入層4011aの膜厚を発光素子ごとに変えることにより光学調整がなされている。また、これらの発光素子は、いずれも第2の電極4003側から光が出る構造を有する。なお、図16には示していないが、発光素子3と重なる第2の電極4003側(図16における第2の電極4003の上方)には、赤色の発光を取り出すためのカラーフィルタが備えられており、発光素子4と重なる第2の電極4003側には、緑色の発光を取り出すためのカラーフィルタが備えられており、発光素子5と重なる第2の電極4003側には、青色の発光を取り出すためのカラーフィルタが備えられており、発光素子6と重なる第2の電極4003側には、黄色の発光を取り出すためのカラーフィルタが備えられており、それぞれの発光色に応じた色純度の高い発光が得られる。
作製した各発光素子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17〜図19に示す。
本実施例では、実施例2の構造式(200)で表される有機金属イリジウム錯体、ビス{2−[5−(2,6−ジメチルフェニル)−2−ピリミジニル−κN]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(ppm2−dmp)2(acac)]の合成方法について説明する。なお、[Ir(ppm2−dmp)2(acac)]の構造を以下に示す。
まず、5−ブロモ−2−ヨードピリミジン1.97gとフェニルボロン酸0.85g、2M炭酸ナトリウム水溶液7.0mL、トルエン18mLを、還流管を付けた200mL三口フラスコに入れ、フラスコ内を窒素置換した。減圧下で撹拌することで脱気した後、テトラキス(トリフェニルホスフィン)パラジウム(0)(略称:Pd(PPh3)4)0.081gを加え、8時間還流した。ここで、Pd(PPh3)40.040gを加え、8時間還流した後、更にPd(PPh3)40.040gを加え、8時間還流することで反応させた。反応溶液に水を加え、ジクロロメタ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、硫酸マグネシウムにて乾燥した。乾燥した後の溶液をろ過した。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、目的のピリミジン誘導体を得た(白色粉末、収率59%)。ステップ1の合成スキームを下記(b−1)に示す。
次に、上記ステップ1で得た5−ブロモ−2−フェニルピリミジン0.96gと2,6−ジメチルフェニルボロン酸1.21g、炭酸ナトリウム0.87g、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)0.035g、水15mL、アセトニトリル15mLを、還流管を付けたナスフラスコに入れ、15分間アルゴンバブリングした。この反応容器にマイクロ波(2.45GHz 100W)を3時間照射することで加熱した。ここで更に2,6−ジメチルフェニルボロン酸1.21g、炭酸ナトリウム0.87g、Pd(PPh3)2Cl2 0.035gをフラスコに入れ、15分間アルゴンバブリングした。この反応容器に再度マイクロ波(2.45GHz 100W)を3時間照射することで加熱した。その後、得られた混合物を水で吸引ろ過した。得られた固体を、トルエン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、目的のピリミジン誘導体Hppm2−dmpを得た(白色粉末、収率64%)。なお、マイクロ波の照射はマイクロ波合成装置(CEM社製 Discover)を用いた。ステップ2の合成スキームを下記(b−2)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2で得たHppm2−dmp0.68g、塩化イリジウム水和物(IrCl3・H2O)(Sigma−Aldrich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、得られた残渣をヘキサンで吸引ろ過、洗浄し、複核錯体[Ir(ppm2−dmp)2Cl]2を得た(黄褐色粉末、収率53%)。ステップ3の合成スキームを下記(b−3)に示す。
さらに、2−エトキシエタノール20mL、上記ステップ3で得た複核錯体[Ir(ppm2−dmp)2Cl]20.48g、アセチルアセトン(略称:Hacac)0.094g、炭酸ナトリウム0.34g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 120W)を60分間照射した。ここで更にHacac0.094gを加え、再度マイクロ波(2.45GHz 200W)を60分間照射することで加熱した。溶媒を留去し、得られた残渣をヘキサンで吸引ろ過した。得られた固体を水、ヘキサンで順次洗浄した。得られた固体を、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により精製した後、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、有機金属錯体[Ir(ppm2−dmp)2(acac)]を黄色粉末として得た(収率58%)。ステップ4の合成スキームを下記(b−4)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 陽極
202 陰極
203 EL層
204 発光層
205 燐光性化合物
206 第1の有機化合物
207 第2の有機化合物
501 第1の電極
502(1) 第1のEL層
502(2) 第2のEL層
502(n−1) 第(n−1)のEL層
502(n) 第(n)のEL層
504 第2の電極
505 電荷発生層
505(1) 第1の電荷発生層
505(2) 第2の電荷発生層
505(n−2) 第(n−2)の電荷発生層
505(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
801 基板
802 FET
803 第1の電極
804 隔壁
805 EL層
806R、806G、806B、806Y 発光領域
807R、807G、807B、807Y 発光素子
808R、808G、808B、808Y 着色層
809 黒色層(ブラックマトリクス)
810 第2の電極
811 封止基板
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
4000 基板
4001 第1の電極
4002a、4002b EL層
4003 第2の電極
4004 電荷発生層
4011a、4011b 正孔注入層
4012a、4012b 正孔輸送層
4013a、4013b 発光層
4013(b1)、4013(b2) 発光層
4014a、4014b 電子輸送層
4015a、4015b 電子注入層
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
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)
- 第1のフェニル基と第2のフェニル基で置換されたピリミジン環を配位子とするイリジウム錯体であり、
前記第1のフェニル基がイリジウムと結合し、
前記ピリミジン環が前記イリジウムと配位結合を形成し、
前記第1のフェニル基が前記ピリミジン環の2位に置換し、
前記第2のフェニル基が前記ピリミジン環の5位に置換し、
前記第1のフェニル基は置換基を有さず、
前記第2のフェニル基は置換基を有さない有機金属イリジウム錯体。 - 式(G2)で表される有機金属イリジウム錯体。
(式(G2)中、Lは、モノアニオン性の配位子を表す。) - 請求項2において、
前記モノアニオン性の配位子は、2つの配位元素がいずれも酸素であるモノアニオン性の二座キレート配位子、又は2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である有機金属イリジウム錯体。 - 請求項1乃至請求項3のいずれか一において、
550nm以上580nm以下の範囲に発光スペクトルの第1のピーク波長を有し、かつ570nm以上630nm以下の範囲に発光スペクトルの第2のピーク波長を有することを特徴とする有機金属イリジウム錯体。 - 請求項1乃至請求項4のいずれか一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、発光層を有し、
前記発光層は、3種以上の有機化合物を有し、
前記3種以上の有機化合物のうちの一は、
請求項1乃至請求項4のいずれか一に記載の有機金属イリジウム錯体である発光素子。 - 請求項5または請求項6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7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7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。
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