JP7345487B2 - 有機金属錯体、発光材料、発光デバイス、有機化合物および複核錯体 - Google Patents
有機金属錯体、発光材料、発光デバイス、有機化合物および複核錯体 Download PDFInfo
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- JP7345487B2 JP7345487B2 JP2020547474A JP2020547474A JP7345487B2 JP 7345487 B2 JP7345487 B2 JP 7345487B2 JP 2020547474 A JP2020547474 A JP 2020547474A JP 2020547474 A JP2020547474 A JP 2020547474A JP 7345487 B2 JP7345487 B2 JP 7345487B2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 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
- 239000005871 repellent Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 230000035939 shock Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000005507 spraying 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
- 238000005092 sublimation method Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(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
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 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
- 150000003918 triazines Chemical class 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 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
- 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Description
図2Aは発光装置の一例を示す上面図である。図2B、図2Cは発光装置の一例を示す断面図である。
図3Aは発光装置の一例を示す上面図である。図3Bは発光装置の一例を示す断面図である。
図4A~図4Eは電子機器の一例を示す図である。
図5は構造式(200)に示す有機化合物の1H-NMRチャートである。
図6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7は構造式(100)に示す有機金属錯体の紫外・可視吸収スペクトル及び発光スペクトルである。
図8は構造式(100)に示す有機金属錯体の重量変化率を示すグラフである。
図9A、図9Bは実施例の発光デバイスを示す断面図である。
図10は発光デバイス1の電流密度-放射発散度特性を示す図である。
図11は発光デバイス1の電圧-電流密度特性を示す図である。
図12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13は発光デバイス1の電圧-放射発散度特性を示す図である。
図14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15は発光デバイス1の発光スペクトルを示す図である。
図16は発光デバイス1の信頼性試験の結果を示す図である。
図17は発光デバイス2の電流密度-放射発散度特性を示す図である。
図18は発光デバイス2の電圧-電流密度特性を示す図である。
図19は発光デバイス2の電流密度-放射束特性を示す図である。
図20は発光デバイス2の電圧-放射発散度特性を示す図である。
図21は発光デバイス2の電流密度-外部量子効率特性を示す図である。
図22は発光デバイス2の発光スペクトルを示す図である。
図23は発光デバイス2の信頼性試験の結果を示す図である。
図24は発光デバイス3の電流密度-放射発散度特性を示す図である。
図25は発光デバイス3の電圧-電流密度特性を示す図である。
図26は発光デバイス3の電流密度-放射束特性を示す図である。
図27は発光デバイス3の電圧-放射発散度特性を示す図である。
図28は発光デバイス3の電流密度-外部量子効率特性を示す図である。
図29は発光デバイス3の発光スペクトルを示す図である。
図30は発光デバイス3の信頼性試験の結果を示す図である。
図31は発光デバイス3の相対強度の角度依存性を示す図である。
図32は発光デバイス3の規格化フォトン強度の角度依存性を示す図である。
本実施の形態では、本発明の一態様の有機金属錯体について説明する。
本発明の一態様の有機金属錯体は、中心金属であるイリジウムに、ベンゾキノキサリン骨格またはナフトキノキサリン骨格を有する配位子が配位した構造を有する。具体的には、本発明の一態様は、一般式(G1)で表される有機金属錯体である。または、本発明の一態様は、一般式(G1)で表される発光材料である。または、本発明の一態様は、一般式(G1)で表される発光デバイス用材料である。
本発明の一態様の有機金属錯体の合成方法としては種々の反応を適用することができる。一般式(G1)で表される有機金属錯体の合成方法を以下に例示する。
一般式(G0)で表される有機化合物は、キノキサリン誘導体の一種であり、本発明の一態様の有機化合物である。一般式(G0)で表される有機化合物は、例えば、以下に示す3種類の合成スキーム(A-1)、(A-1’)、(A-1’’)のいずれか一を用いて合成することができる。
次に、一般式(G1-1)で表される有機金属錯体の合成方法例について、説明する。一般式(G1-1)で表される有機金属錯体は、本発明の一態様の有機金属錯体であり、一般式(G1)におけるnが2である場合に相当する。
次に、一般式(G1-2)で表される有機金属錯体の合成方法例について、説明する。一般式(G1-2)で表される有機金属錯体は、本発明の一態様の有機金属錯体であり、一般式(G1)におけるnが3である場合に相当する。
本実施の形態では、本発明の一態様の発光デバイス及び本発明の一態様の発光装置について図1~図3を用いて説明する。
≪発光デバイスの基本的な構造≫
図1A~図1Cに、一対の電極間にEL層を有する発光デバイスの一例を示す。
次に、発光デバイスの具体的な構造及び作製方法について説明する。ここでは、図1Cに示すシングル構造を有する発光デバイスを用いて説明する。
第1の電極101及び第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、及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、及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)などの希土類金属及びこれらを適宜組み合わせて含む合金、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に正孔を注入する層であり、正孔注入性の高い材料を含む層である。
発光層113は、発光物質を含む層である。
電子輸送層114は、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、これら以外のものも用いることができる。
電子注入層115は、電子注入性の高い物質を含む層である。電子注入層115には、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)、リチウム酸化物(LiOx)等のようなアルカリ金属、アルカリ土類金属、またはそ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。また、電子注入層115にエレクトライドを用いてもよい。エレクトライドとしては、例えば、カルシウムとアルミニウムの混合酸化物に電子を高濃度添加した物質等が挙げられる。なお、上述した電子輸送層114を構成する物質を用いることもできる。
図1Bに示す発光デバイスにおいて、電荷発生層104は、第1の電極101(陽極)と第2の電極102(陰極)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。
図2Aに発光装置の上面図を示し、図2B、図2Cに、図2Aの一点鎖線X1-Y1間及びX2-Y2間の断面図を示す。図2A~図2Cに示す発光装置は、例えば、照明装置に用いることができる。発光装置は、ボトムエミッション、トップエミッション、デュアルエミッションのいずれであってもよい。
本発明の一態様の発光装置は、パッシブマトリクス型またはアクティブマトリクス型とすることができる。アクティブマトリクス型の発光装置について図3を用いて説明する。
本実施の形態では、本発明の一態様の発光デバイスを用いることができる電子機器について図4を用いて説明する。
本実施例では、本発明の一態様の有機金属錯体の合成方法について説明する。本実施例では、実施の形態1の構造式(100)で表されるビス{4,6-ジメチル-2-[3-(3,5-ジメチルフェニル)-2-ベンゾ[g]キノキサリニル-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(dmdpbq)2(dpm)])の合成方法について説明する。
まず、ステップ1では、本発明の一態様の有機化合物であり、構造式(200)に示す、Hdmdpbqを合成した。3,3’,5,5’-テトラメチルベンジル3.20g、2,3-ジアミノナフタレン1.97g、エタノール60mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した後、90℃で7時間半撹拌した。所定時間経過後、溶媒を留去した。その後、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、目的物を得た(黄色固体、収量3.73g、収率79%)。ステップ1の合成スキームを(a-1)に示す。
1H-NMR.δ(CD2Cl2):2.28(s,12H),7.01(s,2H),7.16(s,4H),7.56-7.58(m,2H),8.11-8.13(m,2H),8.74(s,2H).
次に、ステップ2では、本発明の一態様の複核錯体であり、構造式(210)に示す、[Ir(dmdpbq)2Cl]2を合成した。2-エトキシエタノール15mL、水5mL、ステップ1で得たHdmdpbq1.81g、及び、塩化イリジウム水和物(IrCl3・H2O)(フルヤ金属社製)0.66g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、反応させた。所定時間経過後、得られた残渣をメタノールで吸引ろ過、洗浄し、目的物を得た(黒色固体、収量1.76g、収率81%)。ステップ2の合成スキームを(a-2)に示す。
そして、ステップ3では、本発明の一態様の有機金属錯体であり、構造式(100)に示す、[Ir(dmdpbq)2(dpm)]を合成した。2-エトキシエタノール20mL、ステップ2で得た[Ir(dmdpbq)2Cl]21.75g、ジピバロイルメタン(略称:Hdpm)0.50g、及び、炭酸ナトリウム0.95g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3時間照射した。得られた残渣を、メタノールで吸引ろ過した後、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、目的物を得た(暗緑色固体、収量0.42g、収率21%)。得られた暗緑色固体0.41g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2.7Pa、アルゴンガスを流量10.5mL/minで流しながら、300℃で暗緑色固体を加熱した。昇華精製後、暗緑色固体を収率78%で得た。ステップ3の合成スキームを(a-3)に示す。
1H-NMR.δ(CD2Cl2):0.75(s,18H),0.97(s,6H),2.01(s,6H),2.52(s,12H),4.86(s,1H),6.39(s,2H),7.15(s,2H),7.31(s,2H),7.44-7.51(m,4H),7.80(d,2H),7.86(s,4H),8.04(d,2H),8.42(s,2H),8.58(s,2H).
本実施例で示す発光デバイス1は、図9Aに示すように基板800上に第1の電極801が形成され、第1の電極801上に正孔注入層811、正孔輸送層812、発光層813、電子輸送層814、及び電子注入層815が順次積層され、電子注入層815上に第2の電極803が積層された構造を有する。
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。
次に、発光デバイス1に対する信頼性試験を行った。信頼性試験の結果を図16に示す。図16において、縦軸は初期発光強度を100%とした時の規格化発光強度(%)を示し、横軸は駆動時間(h)を示す。なお、信頼性試験は、電流密度を75mA/cm2に設定し、発光デバイス1を駆動させた。
発光デバイス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。
次に、発光デバイス2に対する信頼性試験を行った。信頼性試験の結果を図23に示す。図23において、縦軸は初期発光強度を100%とした時の規格化発光強度(%)を示し、横軸は素子の駆動時間(h)を示す。なお、信頼性試験は、電流密度を75mA/cm2に設定し、発光デバイス2を駆動させた。
本実施例で示す発光デバイス3は、図9Bに示すように基板800上に第1の電極801が形成され、第1の電極801上にEL層802a(正孔注入層811a、正孔輸送層812a、発光層813a、電子輸送層814a、及び電子注入層815a)、電荷発生層816、及びEL層802b(正孔注入層811b、正孔輸送層812b、発光層813b、電子輸送層814b、及び電子注入層815b)が順次積層され、EL層802b上に第2の電極803が積層された構造を有する。
発光デバイス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。
次に、発光デバイス3に対する信頼性試験を行った。信頼性試験の結果を図30に示す。図30において、縦軸は初期発光強度を100%とした時の規格化発光強度(%)を示し、横軸は駆動時間(h)を示す。なお、信頼性試験は、電流密度を75mA/cm2に設定し、発光デバイス3を駆動させた。
次に、発光デバイス3のELスペクトルの視野角特性を調べた。
上記実施例3で用いたビス(ジベンゾ[a,i]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(dbnphz)2(dpm)])の合成方法について具体的に説明する。[Ir(dbnphz)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)、2,3-ジアミノナフタレン0.67g(4.3mmol)、エタノール20mLを反応容器に入れ、5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に溶解し、セライト・アルミナ・セライトの順に積層したろ過材を通して吸引ろ過した。得られたろ液を濃縮し、トルエンとエタノールの混合溶媒にて再結晶して目的物を得た(1.1g、収率74%)。ステップ1の合成スキームを(b-1)に示す。
次に、ステップ1で得たHdbnphz1.1g(2.9mmol)、塩化イリジウム水和物0.39g(1.3mmol)、ジメチルホルムアミド(DMF)30mLを反応容器に加え、容器内を窒素置換し、160℃で7.5時間加熱撹拌した。所定時間経過後、炭酸ナトリウム0.55g(5.2mmol)とジピバロイルメタン0.72g(3.9mmol)を加えて140℃で14時間加熱撹拌した。次に、この混合物を吸引ろ過し、得られた固体を水、エタノールで洗浄した。
Claims (11)
- 一般式(G1)で表される有機金属錯体。
(式中、R1~R11は、それぞれ独立に、水素または炭素数1以上6以下のアルキル基を表し、R1~R4のうち少なくとも2つは、炭素数1以上6以下のアルキル基を表し、R5~R9のうち少なくとも2つは、炭素数1以上6以下のアルキル基を表し、Xは、置換または無置換のベンゼン環またはナフタレン環を表し、nは2または3であり、Lはモノアニオン性の配位子を表す。) - 一般式(G2)で表される有機金属錯体。
(式中、R1、R3、R6、及びR8は、それぞれ独立に、炭素数1以上6以下のアルキル基を表し、R10及びR11は、それぞれ独立に、水素または炭素数1以上6以下のアルキル基を表し、Xは、置換または無置換のベンゼン環またはナフタレン環を表し、nは2または3であり、Lはモノアニオン性の配位子を表す。) - 請求項1または2において、
前記有機金属錯体が発する光の最大ピーク波長は、760nm以上900nm以下である、有機金属錯体。 - 一般式(G1)で表される発光材料。
(式中、R1~R11は、それぞれ独立に、水素または炭素数1以上6以下のアルキル基を表し、R1~R4のうち少なくとも2つは、炭素数1以上6以下のアルキル基を表し、R5~R9のうち少なくとも2つは、炭素数1以上6以下のアルキル基を表し、Xは、置換または無置換のベンゼン環またはナフタレン環を表し、nは2または3であり、Lはモノアニオン性の配位子を表す。) - 一般式(G2)で表される発光材料。
(式中、R1、R3、R6、及びR8は、それぞれ独立に、炭素数1以上6以下のアルキル基を表し、R10及びR11は、それぞれ独立に、水素または炭素数1以上6以下のアルキル基を表し、Xは、置換または無置換のベンゼン環またはナフタレン環を表し、nは2または3であり、Lはモノアニオン性の配位子を表す。) - 請求項4または5において、
前記発光材料が発する光の最大ピーク波長は、760nm以上900nm以下である、発光材料。 - 発光層を有する発光デバイスであり、
前記発光層は、請求項4乃至6のいずれか一に記載の発光材料を有し、
前記発光デバイスは、最大ピーク波長が760nm以上900nm以下の光を発する機能を有する、発光デバイス。 - 一般式(G0)で表される有機化合物。
(式中、R1~R11は、それぞれ独立に、水素または炭素数1以上6以下のアルキル基を表し、R1~R4のうち少なくとも2つは、炭素数1以上6以下のアルキル基を表し、R5~R9のうち少なくとも2つは、炭素数1以上6以下のアルキル基を表し、Xは、置換または無置換のベンゼン環またはナフタレン環を表す。) - 構造式(200)で表される有機化合物。
- 一般式(B)で表される複核錯体。
(式中、Zはハロゲンを表し、R1~R11は、それぞれ独立に、水素または炭素数1以上6以下のアルキル基を表し、R1~R4のうち少なくとも2つは、炭素数1以上6以下のアルキル基を表し、R5~R9のうち少なくとも2つは、炭素数1以上6以下のアルキル基を表し、Xは、置換または無置換のベンゼン環またはナフタレン環を表す。) - 構造式(210)で表される複核錯体。
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Citations (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH599569A5 (en) | 1970-08-11 | 1978-05-31 | Hoechst Ag | Photoinitiators |
JP2007070361A (ja) | 2002-11-13 | 2007-03-22 | Semiconductor Energy Lab Co Ltd | キノキサリン誘導体、有機半導体素子および電界発光素子 |
CN103665048A (zh) | 2012-09-05 | 2014-03-26 | 清华大学 | 一类金属配合物及在有机电致发光器件中的应用 |
CN104193783A (zh) | 2014-07-31 | 2014-12-10 | 石家庄诚志永华显示材料有限公司 | 苯并异喹啉金属配合物及其制备方法与应用 |
JP2015017088A (ja) | 2013-06-14 | 2015-01-29 | 株式会社半導体エネルギー研究所 | 有機金属イリジウム錯体、発光素子、発光装置、および照明装置 |
CN104804045A (zh) | 2015-04-13 | 2015-07-29 | 清华大学 | 近红外发光材料及有机电致发光器件 |
JP2015162463A (ja) | 2014-02-26 | 2015-09-07 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 有機発光表示装置 |
CN105693631A (zh) | 2016-03-11 | 2016-06-22 | 吉林奥来德光电材料股份有限公司 | 一种芳杂环化合物及其制备方法以及一种有机电致发光器件 |
JP2017507129A (ja) | 2014-02-05 | 2017-03-16 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | 金属錯体 |
WO2017103584A1 (en) | 2015-12-15 | 2017-06-22 | Cambridge Display Technology Limited | Light-emitting compound |
JP2018501634A (ja) | 2014-09-30 | 2018-01-18 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 無機半導体材料および有機結合剤を含む半導体組成物 |
CN107722064A (zh) | 2017-11-15 | 2018-02-23 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN107722065A (zh) | 2017-11-15 | 2018-02-23 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN107722063A (zh) | 2017-11-15 | 2018-02-23 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN107880078A (zh) | 2017-11-15 | 2018-04-06 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN107915762A (zh) | 2017-11-15 | 2018-04-17 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
WO2018133579A1 (zh) | 2017-01-22 | 2018-07-26 | 清华大学 | 铱金属配合物及其应用,以及有机电致发光器件 |
US20180261773A1 (en) | 2017-03-13 | 2018-09-13 | Seiko Epson Corporation | Light-emitting element, light-emitting device, light source, authentication device, and electronic apparatus |
US20190062357A1 (en) | 2017-08-28 | 2019-02-28 | Samsung Display Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and organic light-emitting apparatus including the organic light-emitting device |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5072312B2 (ja) | 2005-10-18 | 2012-11-14 | 株式会社半導体エネルギー研究所 | 有機金属錯体及びそれを用いた発光素子、発光装置 |
KR101290011B1 (ko) * | 2009-12-30 | 2013-07-30 | 주식회사 두산 | 유기발광 화합물 및 이를 포함한 유기 전계 발광 소자 |
KR102344294B1 (ko) * | 2014-02-21 | 2021-12-27 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
JP7503499B2 (ja) * | 2018-12-10 | 2024-06-20 | 株式会社半導体エネルギー研究所 | 発光デバイス |
-
2019
- 2019-09-17 JP JP2020547474A patent/JP7345487B2/ja active Active
- 2019-09-17 DE DE112019004869.4T patent/DE112019004869T5/de active Pending
- 2019-09-17 US US17/264,456 patent/US20210320267A1/en active Pending
- 2019-09-17 KR KR1020217011595A patent/KR20210064283A/ko active Search and Examination
- 2019-09-17 CN CN201980058959.1A patent/CN112689914A/zh active Pending
- 2019-09-17 WO PCT/IB2019/057793 patent/WO2020065443A1/ja active Application Filing
-
2023
- 2023-09-05 JP JP2023143738A patent/JP2023169222A/ja active Pending
Patent Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH599569A5 (en) | 1970-08-11 | 1978-05-31 | Hoechst Ag | Photoinitiators |
JP2007070361A (ja) | 2002-11-13 | 2007-03-22 | Semiconductor Energy Lab Co Ltd | キノキサリン誘導体、有機半導体素子および電界発光素子 |
CN103665048A (zh) | 2012-09-05 | 2014-03-26 | 清华大学 | 一类金属配合物及在有机电致发光器件中的应用 |
JP2015017088A (ja) | 2013-06-14 | 2015-01-29 | 株式会社半導体エネルギー研究所 | 有機金属イリジウム錯体、発光素子、発光装置、および照明装置 |
JP2017507129A (ja) | 2014-02-05 | 2017-03-16 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | 金属錯体 |
JP2015162463A (ja) | 2014-02-26 | 2015-09-07 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 有機発光表示装置 |
CN104193783A (zh) | 2014-07-31 | 2014-12-10 | 石家庄诚志永华显示材料有限公司 | 苯并异喹啉金属配合物及其制备方法与应用 |
JP2018501634A (ja) | 2014-09-30 | 2018-01-18 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 無機半導体材料および有機結合剤を含む半導体組成物 |
CN104804045A (zh) | 2015-04-13 | 2015-07-29 | 清华大学 | 近红外发光材料及有机电致发光器件 |
WO2017103586A1 (en) | 2015-12-15 | 2017-06-22 | Cambridge Display Technology Limited | Light-emitting composition |
WO2017103584A1 (en) | 2015-12-15 | 2017-06-22 | Cambridge Display Technology Limited | Light-emitting compound |
CN105693631A (zh) | 2016-03-11 | 2016-06-22 | 吉林奥来德光电材料股份有限公司 | 一种芳杂环化合物及其制备方法以及一种有机电致发光器件 |
WO2018133579A1 (zh) | 2017-01-22 | 2018-07-26 | 清华大学 | 铱金属配合物及其应用,以及有机电致发光器件 |
US20180261773A1 (en) | 2017-03-13 | 2018-09-13 | Seiko Epson Corporation | Light-emitting element, light-emitting device, light source, authentication device, and electronic apparatus |
US20190062357A1 (en) | 2017-08-28 | 2019-02-28 | Samsung Display Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and organic light-emitting apparatus including the organic light-emitting device |
CN107722064A (zh) | 2017-11-15 | 2018-02-23 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN107722065A (zh) | 2017-11-15 | 2018-02-23 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN107722063A (zh) | 2017-11-15 | 2018-02-23 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN107880078A (zh) | 2017-11-15 | 2018-04-06 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN107915762A (zh) | 2017-11-15 | 2018-04-17 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
Non-Patent Citations (3)
Title |
---|
Guan‐Yu CHEN et al.,"Cationic IrIII Emitters with Near‐Infrared Emission Beyond 800 nm and Their Use in Light‐Emitting Electrochemical Cells",Chemistry - A European Journal,2019年02月14日,Vol. 25,No. 21,p.5489-5497,DOI: 10.1002/chem.201805902 |
Jiahao GUO et al.,"Two efficient near-infrared (NIR) luminescent [Ir(C^N)2(N^O)]-characteristic complexes with 8-hydroxyquinoline (8-Hq) as the ancillary ligand",Inorganic Chemistry Communications,2019年01月15日,Vol. 101,p.69-73,DOI: 10.1016/j.inoche.2019.01.019 |
Young-Inn KIM et al.,"Structural and Photoluminescent Properties of Near-Infrared Emissive Bis(2,3-Diphenylbenzoquinoxalinato)(2-Pyrazinecarboxylato)ridium(III)",Bulletin of the Korean Chemical Society,2018年01月08日,Vol. 39,No. 1,p.133-136,DOI: 10.1002/bkcs.11357 |
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CN112689914A (zh) | 2021-04-20 |
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