JP7478670B2 - 有機金属錯体、発光デバイス、発光装置、電子機器、および照明装置 - Google Patents
有機金属錯体、発光デバイス、発光装置、電子機器、および照明装置 Download PDFInfo
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- JP7478670B2 JP7478670B2 JP2020561972A JP2020561972A JP7478670B2 JP 7478670 B2 JP7478670 B2 JP 7478670B2 JP 2020561972 A JP2020561972 A JP 2020561972A JP 2020561972 A JP2020561972 A JP 2020561972A JP 7478670 B2 JP7478670 B2 JP 7478670B2
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 125
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- 239000003446 ligand Substances 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 27
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
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- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
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- 239000011733 molybdenum Substances 0.000 description 1
- WOYDRSOIBHFMGB-UHFFFAOYSA-N n,9-diphenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 WOYDRSOIBHFMGB-UHFFFAOYSA-N 0.000 description 1
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- XAWQWMLNBYNXJX-UHFFFAOYSA-N n,n-diphenyl-9-[4-(10-phenylanthracen-9-yl)phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C(C=4C=CC=CC=4)=C4C=CC=CC4=3)C2=CC=1)C1=CC=CC=C1 XAWQWMLNBYNXJX-UHFFFAOYSA-N 0.000 description 1
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- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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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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- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
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- 229920002994 synthetic fiber Polymers 0.000 description 1
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
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- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 150000003518 tetracenes Chemical class 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
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 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
Images
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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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- 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
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21S—NON-PORTABLE LIGHTING DEVICES; SYSTEMS THEREOF; VEHICLE LIGHTING DEVICES SPECIALLY ADAPTED FOR VEHICLE EXTERIORS
- F21S2/00—Systems of lighting devices, not provided for in main groups F21S4/00 - F21S10/00 or F21S19/00, e.g. of modular construction
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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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
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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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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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
- H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
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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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- General Engineering & Computer Science (AREA)
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- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Description
図2A、図2B、図2Cは発光装置について説明する図である。
図3A、図3Bは発光装置について説明する図である。
図4A、図4B、図4C、図4D、図4E、図4F、図4Gは電子機器について説明する図である。
図5A、図5B、図5Cは電子機器について説明する図である。
図6A、図6Bは自動車について説明する図である。
図7A、図7Bは照明装置について説明する図である。
図8は構造式(100)に示す有機金属錯体の1H-NMRチャートである。
図9は構造式(100)に示す有機金属錯体の溶液中の紫外・可視吸収スペクトル及び発光スペクトルである。
図10は構造式(101)に示す有機金属錯体の1H-NMRチャートである。
図11は構造式(101)に示す有機金属錯体の溶液中の紫外・可視吸収スペクトル及び発光スペクトルである。
図12A、図12Bは蒸着方法について説明する図である。
図13は発光デバイスについて説明する図である。
図14は発光デバイス1の電流密度-放射束特性を示す図である。
図15は発光デバイス1の電圧-放射輝度特性を示す図である。
図16は発光デバイス1の電圧-電流特性を示す図である。
図17は発光デバイス1の電流密度-外部量子効率特性を示す図である。
図18は発光デバイス1の電圧-外部エネルギー効率特性を示す図である。
図19は発光デバイス1の発光スペクトルを示す図である。
図20は発光デバイス1の信頼性を示す図である。
図21は構造式(116)に示す有機金属錯体の溶液中の紫外・可視吸収スペクトル及び発光スペクトルである。
本実施の形態では、本発明の一態様である有機金属錯体について説明する。
下記一般式(G0)で表されるキノキサリン誘導体は以下のような合成方法により合成することができる。
次に、一般式(G1)で表される有機金属錯体の合成方法について説明する。まず、下記合成スキーム(D)に示すように、一般式(G0)で表されるキノキサリン誘導体またはモノアニオン性配位子Lと、ハロゲンを含む第9族または第10族の金属化合物とを、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る複核錯体(d1)またはモノアニオン性の配位子を含む複核錯体(d2)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。
本実施の形態では、本発明の一態様である発光デバイスの一例について説明する。なお、本実施の形態で説明する発光デバイスには、本発明の一態様である有機金属錯体を用いることができる。
図1Aは、一対の電極間に発光層を含むEL層を有する発光デバイスの一例を示す。具体的には、第1の電極101と第2の電極102との間にEL層103が挟まれた構造を有する。なお、EL層103は、例えば、第1の電極101を陽極とした場合、正孔(ホール)注入層111、正孔(ホール)輸送層112、発光層113、電子輸送層114、電子注入層115が機能層として、順次積層された構造を有する。また、その他の発光デバイスの構造として、図1Bに示すように一対の電極間に電荷発生層104を挟んで形成される複数のEL層(103a、103b)を有する構成(タンデム構造)とすることにより低電圧駆動を可能とする発光デバイスや、一対の電極間に微小光共振器(マイクロキャビティ)構造を形成することにより光学特性を向上させた発光デバイス等も本発明の一態様に含めることとする。なお、電荷発生層104は、第1の電極101と第2の電極102に電圧を印加したときに、隣り合う一方のEL層に電子を注入し、他方のEL層に正孔を注入する機能を有する。
第1の電極101および第2の電極102を形成する材料としては、上述した両電極の機能が満たせるのであれば、以下に示す材料を適宜組み合わせて用いることができる。例えば、金属、合金、電気伝導性化合物、およびこれらの混合物などを適宜用いることができる。具体的には、In-Sn酸化物(ITOともいう)、In-Si-Sn酸化物(ITSOともいう)、In-Zn酸化物、In-W-Zn酸化物が挙げられる。その他、アルミニウム(Al)、チタン(Ti)、クロム(Cr)、マンガン(Mn)、鉄(Fe)、コバルト(Co)、ニッケル(Ni)、銅(Cu)、ガリウム(Ga)、亜鉛(Zn)、インジウム(In)、スズ(Sn)、モリブデン(Mo)、タンタル(Ta)、タングステン(W)、パラジウム(Pd)、金(Au)、白金(Pt)、銀(Ag)、イットリウム(Y)、ネオジム(Nd)などの金属、およびこれらを適宜組み合わせて含む合金を用いることもできる。その他、上記例示のない元素周期表の第1族または第2族に属する元素(例えば、リチウム(Li)、セシウム(Cs)、カルシウム(Ca)、ストロンチウム(Sr))、ユウロピウム(Eu)、イッテルビウム(Yb)などの希土類金属およびこれらを適宜組み合わせて含む合金、その他グラフェン等を用いることができる。
正孔注入層111は、陽極である第1の電極101からEL層103に正孔(ホール)を注入する層であり、有機アクセプター材料や正孔注入性の高い材料を含む層である。
正孔輸送層112は、正孔注入層111によって、第1の電極101から注入された正孔を発光層113に輸送する層である。なお、正孔輸送層112は、正孔輸送性材料を含む層である。従って、正孔輸送層112には、正孔注入層111に用いることができる正孔輸送性材料を用いることができる。
発光層113は、発光物質(有機化合物)を含む層である。なお、発光層113に用いることができる発光物質としては、特に限定は無く、一重項励起エネルギーを可視光領域の発光に変える発光物質(例えば、蛍光発光物質)、または三重項励起エネルギーを可視光領域の発光に変える発光物質(例えば、燐光発光物質やTADF材料など)を用いることができる。また、青色、紫色、青紫色、緑色、黄緑色、黄色、橙色、赤色などの発光色を呈する物質を適宜用いることができる。
電子輸送層114は、後述する電子注入層115によって第2の電極102から注入された電子を発光層113に輸送する層である。なお、電子輸送層114は、電子輸送性材料を含む層である。電子輸送層114に用いる電子輸送性材料は、1×10-6cm2/Vs以上の電子移動度を有する物質が好ましい。なお、正孔よりも電子の輸送性の高い物質であれば、これら以外のものを用いることができる。また、電子輸送層114は、単層でも機能するが、必要に応じて2層以上の積層構造とすることにより、デバイス特性を向上させることもできる。
電子注入層115は、陰極102からの電子の注入効率を高めるための層であり、陰極102の材料の仕事関数の値と、電子注入層115に用いる材料のLUMO準位の値とを比較した際、その差が小さい(0.5eV以下)材料を用いることが好ましい。従って、電子注入層115には、リチウム、セシウム、フッ化リチウム(LiF)、フッ化セシウム(CsF)、フッ化カルシウム(CaF2)、8-(キノリノラト)リチウム(略称:Liq)、2-(2-ピリジル)フェノラトリチウム(略称:LiPP)、2-(2-ピリジル)-3-ピリジノラトリチウム(略称:LiPPy)、4-フェニル-2-(2-ピリジル)フェノラトリチウム(略称:LiPPP)リチウム酸化物(LiOx)、炭酸セシウム等のようなアルカリ金属、アルカリ土類金属、またはこれらの化合物を用いることができる。また、フッ化エルビウム(ErF3)のような希土類金属化合物を用いることができる。
なお、図1Bの発光デバイスにおける電荷発生層104は、第1の電極(陽極)101と第2の電極(陰極)102との間に電圧を印加したときに、EL層103aに電子を注入し、EL層103bに正孔を注入する機能を有する。なお、電荷発生層104は、正孔輸送性材料に電子受容体(アクセプター)が添加された構成であっても、電子輸送性材料に電子供与体(ドナー)が添加された構成であってもよい。また、これらの両方の構成が積層されていても良い。なお、上述した材料を用いて電荷発生層104を形成することにより、EL層が積層された場合における駆動電圧の上昇を抑制することができる。
本実施の形態で示した発光デバイスは、様々な基板上に形成することができる。なお、基板の種類は、特定のものに限定されることはない。基板の一例としては、半導体基板(例えば単結晶基板又はシリコン基板)、SOI基板、ガラス基板、石英基板、プラスチック基板、金属基板、ステンレス・スチル基板、ステンレス・スチル・ホイルを有する基板、タングステン基板、タングステン・ホイルを有する基板、可撓性基板、貼り合わせフィルム、繊維状の材料を含む紙、又は基材フィルムなどが挙げられる。
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。なお、図2Aに示す発光装置は、第1の基板201上のトランジスタ(FET)202と発光デバイス(203R、203G、203B、203W)が電気的に接続されてなるアクティブマトリクス型の発光装置であり、複数の発光デバイス(203R、203G、203B、203W)は、共通のEL層204を有し、また、各発光デバイスの発光色に応じて、各発光デバイスの電極間の光学距離が調整されたマイクロキャビティ構造を有する。また、EL層204から得られた発光が第2の基板205に形成されたカラーフィルタ(206R、206G、206B)を介して射出されるトップエミッション型の発光装置である。
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デバイス、本発明の一態様である発光デバイスを有す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。なお、発光装置は、本実施の形態で説明する電子機器において、主に表示部に適用することができる。
本実施の形態では、本発明の一態様である発光装置、またはその一部である発光デバイスを適用して作製される照明装置の構成について図7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様態である有機金属錯体、ビス(13,14-ジシアノベンゾ[a]ナフト[2,1-c]フェナジン-10-イル-κC10,κN11)(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(bnphz-dCN)2(dpm)])の合成方法について説明する。なお、[Ir(bnphz-dCN)2(dpm)]の構造を以下に示す。
まず、クリセン-5,6-ジオン1.0g(4.0mmol)、4,5-ジアミノフタロニトリル0.69g(4.4mmol)、エタノール20mLを反応容器に入れ、63時間加熱還流した。所定時間経過後、得られた混合物を吸引ろ過し、固体をエタノールで洗浄した。この固体を加熱トルエンで洗浄し、目的物を得た(1.1g、収率70%)。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2で得た配位子、Hbnphz-dCN1.0g(2.6mmol)、塩化イリジウム水和物0.37g(1.3mmol)、ジメチルホルムアミド(DMF)26mLを反応容器に加え、容器内を窒素置換し、160℃で7時間加熱撹拌した。所定時間経過後、炭酸ナトリウム0.70g(6.6mmol)とジピバロイルメタン0.70g(3.8mmol)を加えて140℃で8時間加熱撹拌した。得られた反応混合物を吸引ろ過し、水、エタノールで洗浄した。得られた固体をジクロロメタンで洗浄し、得られたろ液を濃縮して固体を得た。この固体をフラッシュ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、ジクロロメタン:トルエン=3:7の混合溶媒を用い、徐々にジクロロメタンの量を増やして極性を上げながら行った。得られたフラクションを濃縮して得た固体をヘキサンにて洗浄して、目的物を得た(黒色固体5mg、収率0.4%)。
ステップ2の合成スキームを下記式(a-2)に示す。
本実施例では、実施の形態1の構造式(101)で表される本発明の一様態である有機金属錯体、ビス{4,6-ジメチル-[5,7-ビス(トリフルオロメチル)-3-(3,5-ジメチルフェニル)-2-キノキサリニル-κN1]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(dmdpq-dCF3)2(acac)])の合成方法について説明する。なお、[Ir(dmdpq-dCF3)2(acac)]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4.1g(15mmol)、3,5-ビス(トリフルオロメチル)-1,2-フェニレンジアミン4.1g(17mmol)、エタノール80mLを反応容器に入れ23時間加熱還流した。ここに、酢酸0.098g(1.6mmol)を加え、18時間加熱還流した。所定時間経過後、得られた混合物を吸引ろ過し、固体をエタノールで洗浄して目的物を得た(淡黄色固体6.8g、収率93%)。ステップ1の合成スキームを下記式(b-1)に示す。
次に、上記ステップ2で得た、配位子Hdmdpq-dCF32.0g(4.2mmol)、トリス(アセチルアセトナト)イリジウム(III)0.42g(0.84mmol)を反応容器に入れ、容器内をアルゴン置換した後、250℃で44時間加熱撹拌した。所定時間経過後、反応物をジクロロメタンに溶解しシリカゲルに吸着させてシリカゲルカラムクロマトグラフィーによる精製を行った。展開溶媒にはトルエン:ヘキサン=3:1を用いた。得られたフラクションを濃縮して固体を得た。この固体をジクロロメタンとメタノールの混合溶媒により精製して目的物を得た(黒色固体174mg、収率17%)。ステップ2の合成スキームを下記式(b-2)に示す。
本実施例で示す発光デバイスは、図13に示すように基板900上に形成された第1の電極901上に正孔注入層911、正孔輸送層912、発光層913、電子輸送層914、電子注入層915が順次積層され、電子注入層915上に第2の電極903が積層された構造を有する。
作製した発光デバイス1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、発光デバイス1の電流密度-放射束特性を図14、電圧-放射輝度特性を図15、電圧-電流特性を図16、電流密度-外部量子効率特性を図17、電流密度-外部エネルギー効率特性を図18にそれぞれ示す。なお、放射束、外部量子効率は、デバイスの配光特性がランバーシアン型と仮定し、放射輝度を用いて算出した。
本実施例では、実施の形態1の構造式(116)で表される本発明の一様態である有機金属錯体、ビス{3-[5,7-ビス(トリフルオロメチル)-3-(2-ナフチル)-2―キノキサリニル-κN1]-2-ナフチル-κC}(2,4-ペンタンジオナト-κ2O,O’)イリジウム(III)((略称:[Ir(d2nq-dCF3)2(acac)])の合成方法について説明する。なお、[Ir(d2nq-dCF3)2(acac)]の構造を以下に示す。
まず、2-ブロモナフタレン25g(122mmol)と炭酸ビニレン3.6g(40mmol)、トリフェニルホスフィン2.1g(8mmol)、炭酸セシウム28g(88mmol)、ジメチルホルムアミド180mLを三口フラスコに入れ、フラスコ内を脱気、窒素置換した。ここに酢酸パラジウム(II)0.90g(4.0mmol)を加え120℃で4.5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。抽出溶液を水、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。得られた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。展開溶媒にはトルエン:ヘキサン=4:1の混合溶媒を用いた。得られたフラクションを濃縮して目的物である白色固体を3.2g、収率26%で得た。ステップ1の合成スキームを下記式(c-1)に示す。
次に、上記ステップ2で得た1,2-ジ-2-ナフチル-1,2-エタンジオン1.6g(4.8mmol)、3,5-ビス(トリフルオロメチル)-1,2-フェニレンジアミン1.3g(5.3mmol)、エタノール25mL、酢酸30mg(0.48mmol)を反応容器に入れ22時間加熱還流した。ここに、酢酸をパスツールで2滴加え、さらに41時間加熱還流した。所定時間経過後、得られた混合物を吸引ろ過し、固体を水、エタノールで洗浄して目的物を得た(淡黄色固体2.4g、収率96%)。ステップ2の合成スキームを下記式(c-2)に示す。
次に、上記ステップ2で得た配位子、Hd2nq-dCF32.0g(3.8mmol)、トリス(アセチルアセトナト)イリジウム(III)0.38g(0.77mmol)を反応容器に入れ、容器内をアルゴン置換した後、250℃で48時間加熱撹拌した。所定時間経過後、反応物をトルエンに溶解し、シリカゲルカラムクロマトグラフィーによる精製を行った。展開溶媒にはトルエンを用いた。得られたフラクションを濃縮して固体を得た。この固体をジクロロメタンとエタノールの混合溶媒により精製して目的物を得た(黒色固体76mg、収率7.5%)。ステップ3の合成スキームを下記式(c-3)に示す。
Claims (14)
- 一般式(G2)で表される有機金属錯体。
(式中、Mはイリジウムを表す。また、R1~R13はそれぞれ独立に、水素、炭素数1~6のアルキル基、置換もしくは無置換の炭素数6~12のアリール基、または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し、かつ、R1~R4の少なくとも一は、シアノ基、トリフルオロメチル基、トリフルオロメチルスルホニル基、またはペンタフルオロスルファニル基のいずれかを表す。また、R9およびR10は、互いに結合し、環を形成していても良い。また、R5およびR6、R6およびR7、R7およびR8、R8およびR9、R10およびR11、R11およびR12、ならびにR12およびR13のいずれか一または複数が互いに結合し、置換もしくは無置換の炭素数3~24の飽和環もしくは不飽和環を形成してもよい。また、Lは、モノアニオン性の配位子を表す。また、m+n=3(但し、m=0、1または2、n=1、2、または3のいずれか)である。) - 一般式(G4)で表される有機金属錯体。
(式中、R1~R13はそれぞれ独立に、水素、炭素数1~6のアルキル基、置換もしくは無置換の炭素数6~12のアリール基、または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し、かつ、R1~R4の少なくとも一は、シアノ基、トリフルオロメチル基、トリフルオロメチルスルホニル基、またはペンタフルオロスルファニル基のいずれかを表す。また、R9およびR10は、互いに結合し、環を形成していても良い。また、R5およびR6、R6およびR7、R7およびR8、R8およびR9、R10およびR11、R11およびR12、ならびにR12およびR13のいずれか一または複数が互いに結合し、置換もしくは無置換の炭素数3~24の飽和環もしくは不飽和環を形成してもよい。また、Lは、モノアニオン性の配位子を表す。) - 一般式(G5)で表される有機金属錯体。
(式中、R1~R8およびR11~R13はそれぞれ独立に、水素、炭素数1~6のアルキル基、置換もしくは無置換の炭素数6~12のアリール基、または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し、かつ、R1~R4の少なくとも一は、シアノ基、トリフルオロメチル基、トリフルオロメチルスルホニル基、およびペンタフルオロスルファニル基のいずれかを表す。また、R5およびR6、R6およびR7、R7およびR8、R11およびR12、ならびにR12およびR13のいずれか一または複数が互いに結合し、置換もしくは無置換の炭素数3~24の飽和環もしくは不飽和環を形成してもよい。また、Lは、モノアニオン性の配位子を表す。) - 請求項1乃至請求項3のいずれか一において、
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である有機金属錯体。 - 一般式(G6)で表される有機金属錯体。
(式中、R1~R16はそれぞれ独立に、水素、炭素数1~6のアルキル基、置換もしくは無置換の炭素数6~12のアリール基、または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し、かつ、R1~R4の少なくとも一は、シアノ基、トリフルオロメチル基、トリフルオロメチルスルホニル基、またはペンタフルオロスルファニル基のいずれかを表す。また、R9およびR10は、互いに結合し、環を形成していても良い。また、R5およびR6、R6およびR7、R7およびR8、R8およびR9、R10およびR11、R11およびR12、ならびにR12およびR13のいずれか一または複数が互いに結合し、置換もしくは無置換の炭素数3~24の飽和環もしくは不飽和環を形成してもよい。) - 一般式(G7)で表される有機金属錯体。
(式中、R1~R8およびR11~R16はそれぞれ独立に、水素、炭素数1~6のアルキル基、置換もしくは無置換の炭素数6~12のアリール基、または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し、かつ、R1~R4の少なくとも一は、シアノ基、トリフルオロメチル基、トリフルオロメチルスルホニル基、またはペンタフルオロスルファニル基のいずれかを表す。また、R5およびR6、R6およびR7、R7およびR8、R11およびR12、ならびにR12およびR13のいずれか一または複数が互いに結合し、置換もしくは無置換の炭素数3~24の飽和環もしくは不飽和環を形成してもよい。) - 請求項1乃至請求項6のいずれか一において、
R 1 ~R 4 の少なくとも一は、シアノ基、またはトリフルオロメチル基を表す、有機金属錯体。 - 請求項1乃至請求項7のいずれか一において、
R 5 およびR 6 、R 6 およびR 7 、R 7 およびR 8 、R 8 およびR 9 、R 10 およびR 11 、R 11 およびR 12 、ならびにR 12 およびR 13 のいずれか一または複数が互いに結合し、置換もしくは無置換のベンゼン環を形成する、有機金属錯体。 - 構造式(100)、構造式(101)または構造式(116)で表される有機金属錯体。
- 請求項1乃至請求項9のいずれか一に記載の有機金属錯体を有する発光デバイス。
- 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9のいずれか一に記載の有機金属錯体を有する発光デバイス。 - 請求項10または請求項11に記載の発光デバイスと、
トランジスタ、または基板のいずれか一と、
を有する発光装置。 - 請求項12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、スピーカのいずれか一と、
を有する電子機器。 - 請求項12に記載の発光装置と、
筐体、カバー、または、支持台のいずれか一と、
を有する照明装置。
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