JPWO2020079524A1 - 有機化合物、発光デバイス用材料、発光デバイス、発光装置、発光モジュール、電子機器、及び照明装置 - Google Patents
有機化合物、発光デバイス用材料、発光デバイス、発光装置、発光モジュール、電子機器、及び照明装置 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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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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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- 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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- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
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、図3Cは発光装置の一例を示す断面図である。図3Bは発光デバイスの一例を示す断面図である。
図4A、図4Bは発光装置の一例を示す断面図である。
図5Aは発光装置の一例を示す上面図である。図5Bは発光装置の一例を示す断面図である。図5C、図5Dはトランジスタの一例を示す断面図である。
図6A、図6B、図6C、図6Dは電子機器の一例を示す図である。
図7A、図7B、図7C、図7D、図7E、図7Fは電子機器の一例を示す図である。
図8Aは自動車の外観の一例を示す図である。図8B、図8Cは自動車の車内の一例を示す図である。
図9A、図9Cは生体認証機器の一例を示す図である。図9Bは光源の一例を示す図である。図9Dは非破壊検査機器の一例を示す図である。図9Eは電携帯電話機の一例を示す図である。
図10は構造式(100)に示す有機化合物の1H−NMRチャートである。
図11A、図11Bは構造式(100)に示す有機化合物の紫外・可視吸収スペクトル及び発光スペクトルである。
図12は実施例の発光デバイスを示す断面図である。
図13は発光デバイス1の電流密度−輝度特性を示す図である。
図14は発光デバイス1の電圧−輝度特性を示す図である。
図15は発光デバイス1の輝度−電流効率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の輝度−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の発光スペクトルを示す図である。
図19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20は発光デバイス2、3の電流密度−輝度特性を示す図である。
図21は発光デバイス2、3の電圧−輝度特性を示す図である。
図22は発光デバイス2、3の輝度−電流効率特性を示す図である。
図23は発光デバイス2、3の電圧−電流特性を示す図である。
図24は発光デバイス2、3の輝度−外部量子効率特性を示す図である。
図25は発光デバイス2、3の発光スペクトルを示す図である。
図26は発光デバイス2、3の信頼性試験の結果を示す図である。
図27は構造式(113)に示す有機化合物の1H−NMRチャートである。
本実施の形態では、本発明の一態様の有機化合物について説明する。
本発明の一態様は、フロキノキサリン骨格またはチエノキノキサリン骨格に縮合芳香環が縮合した構造を有する有機化合物である。また、本発明の一態様は、フロキノキサリン骨格またはチエノキノキサリン骨格に縮合芳香環が縮合した構造を有する発光デバイス用材料である。当該発光デバイス用材料は、特に、赤色または近赤外光を発する発光デバイス用の材料であることが好ましい。また、当該発光デバイス用材料は、発光デバイス用のホスト材料または電子輸送性材料であることが好ましい。
本発明の一態様の有機化合物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(G0)で表される有機化合物の合成方法を以下に例示する。以下では、一般式(G0’)で表される有機化合物の合成方法の一例について説明する。なお、一般式(G0’)で表される有機化合物は、縮合芳香環が縮合したフロキノキサリン誘導体または縮合芳香環が縮合したチエノキノキサリン誘導体であり、一般式(G0)で表される有機化合物の一態様である。
まず、合成スキーム(A−1)に示すように、メチルオキシ基またはメチルチオ基で置換されたアリールボロン酸(a1)と、アミノ基とハロゲンで置換されたキノキサリン誘導体(a2)と、をカップリングして、中間体(a3)を得た後、中間体(a3)と、亜硝酸tert−ブチルとを反応させ、環化させることで、縮合芳香環が縮合したフロキノキサリン誘導体または縮合芳香環が縮合したチエノキノキサリン誘導体(a4)を得る。なお、合成スキーム(A−1)においてY1がハロゲンの場合、さらにハロゲンを含む芳香環のボロン酸(Y3−(α)n−B2)をカップリングして得られた中間体(a5)もキノキサリン誘導体(a4)と同様に以降の反応に用いることができる。
本実施の形態では、本発明の一態様の発光デバイスについて図1を用いて説明する。本実施の形態では、可視光または近赤外光を発する機能を有する発光デバイスについて説明する。
≪発光デバイスの基本的な構造≫
図1A〜図1D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について説明する。ここでは、図1B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。発光層113は、1種または複数種の発光物質を有することができる。発光物質としては、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。また、発光物質として、近赤外光を発する物質を用いることもできる。また、複数の発光層に異なる発光物質を用いることにより、異なる発光色を呈する構成(例えば、補色の関係にある発光色を組み合わせて得られる白色発光)とすることができる。さらに、1つの発光層が異なる発光物質を有する積層構造であってもよい。
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。本発明の一態様の発光デバイスは、電子輸送層114に用いる電子輸送性材料として、本発明の一態様の有機化合物を有することが好ましい。
電子注入層115は、電子注入性の高い材料を含む層である。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1C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。
本実施の形態では、本発明の一態様の発光装置について図2〜図5を用いて説明する。
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。
図3Aに、発光装置の断面図を示す。図3Aに示す発光装置は、トランジスタと発光デバイスと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る。
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5を用いて説明する。
本実施の形態では、本発明の一態様の電子機器について図を用いて説明する。
本実施例では、本発明の一態様の有機化合物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10−[(3’−ジベンゾチオフェン−4−イル)ビフェニル−3−イル]ナフト[1’,2’:4,5]フロ[2,3−b]キノキサリン(略称:10mDBtBPNfqn)の合成方法について説明する。
まず、3,7−ジクロロキノキサリン−2−アミン2.49g、2−メトキシナフタレン−1−ボロン酸2.38g、炭酸セシウム3.90g、1,4−ジオキサン46mL、及び水23mL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。フラスコ内を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)1.38gを加え、80℃で6時間撹拌し、反応させた。
次に、ステップ1で得た7−クロロ−3−(2−メトキシナフタレン−1−イル)キノキサリン−2−アミン2.89g、脱水テトラヒドロフラン90mL、及び、氷酢酸90mLを三口フラスコに入れ、内部を窒素置換した。フラスコを−10℃に冷却した後、亜硝酸tert−ブチル3.0mLを滴下し、−10℃で1時間、0℃で18時間攪拌した。所定時間経過後、得られた懸濁液に水400mLを加え、吸引ろ過することにより、目的のキノキサリン誘導体を得た(黄白色固体、収量1.63g、収率64%)。ステップ2の合成スキームを(a−2)に示す。
さらに、ステップ2で得た10−クロロナフト[1’,2’:4,5]フロ[2,3−b]キノキサリン1.63g、3’−(4−ジベンゾチオフェン)−1,1’−ビフェニル−3−ボロン酸3.29g、リン酸三カリウム5.48g、tert−ブチルアルコール1.42g、ジエチレングリコールジメチルエーテル(略称:diglyme)60mL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、酢酸パラジウム(II)(略称:Pd(OAc)2)0.10g、ジ(1−アダマンチル)−n−ブチルホスフィン(略称:CataCXium A)0.32gを加え、140℃で31時間半撹拌し、反応させた。
本実施例で示す発光デバイス1は、図12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。
発光デバイス2、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、本発明の一態様の有機化合物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(113)で表される12−[(3’−ジベンゾチオフェン−4−イル)ビフェニル−3−イル]フェナントロ[9’,10’:4,5]フロ[2,3−b]キノキサリン(略称:12mDBtBPPnfqn)の合成方法について説明する。
まず、3,7−ジクロロキノキサリン−2−アミン2.70g、10−メトキシフェナントレン−9−ボロン酸3.27g、炭酸セシウム4.22g、1,4−ジオキサン50mL、及び水25mL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。フラスコ内を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)0.75gを加え、80℃で11時間撹拌し、反応させた。
次に、ステップ1で得た7−クロロ−3−(10−メトキシフェナントレン−9−イル)キノキサリン−2−アミン3.29g、脱水テトラヒドロフラン100mL、及び氷酢酸100mLを三口フラスコに入れ、内部を窒素置換した。フラスコを−10℃に冷却した後、亜硝酸tert−ブチル3.1mLを滴下し、−10℃で1時間、0℃で24時間撹拌した。所定時間経過後、得られた懸濁液に水400mLを加え、吸引ろ過することにより、目的のキノキサリン誘導体を得た(黄色固体、収量2.52g、収率82%)。ステップ2の合成スキームを(b−2)に示す。
さらに、ステップ2で得た12−クロロフェナントロ[9’,10’:4,5]フロ[2,3−b]キノキサリン1.19g、3’−(4−ジベンゾチオフェン)−1,1’−ビフェニル−3−ボロン酸1.58g、リン酸三カリウム2.19g、tert−ブチルアルコール0.76g、ジエチレングリコールジメチルエーテル(略称:diglyme)27mL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、酢酸パラジウム(II)(略称:Pd(OAc)2)15mg、ジ(1−アダマンチル)−n−ブチルホスフィン(略称:CataCXium A)48mgを加え、150℃で15時間撹拌し、反応させた。
Claims (25)
- 請求項1または2において、
前記正孔輸送性の骨格は、置換もしくは無置換のジアリールアミノ基、置換もしくは無置換の縮合芳香族炭化水素環、及び置換もしくは無置換のπ過剰型の縮合複素芳香環のうちいずれか一である、有機化合物。 - 請求項4または5において、
前記縮合環は、置換もしくは無置換の縮合芳香族炭化水素環、及び置換もしくは無置換のπ過剰型の縮合複素芳香環のうちいずれか一である、有機化合物。 - 請求項4または5において、
前記縮合環は、ジベンゾチオフェン骨格、ジベンゾフラン骨格、及びカルバゾール骨格のうちいずれか一を有する、置換もしくは無置換の縮合複素芳香環である、有機化合物。 - 請求項4または5において、
前記縮合環は、ナフタレン骨格、フルオレン骨格、トリフェニレン骨格、及びフェナントレン骨格のうちいずれか一を有する、置換もしくは無置換の縮合芳香族炭化水素環である、有機化合物。 - 一般式(G0)で表される有機化合物。
- 一般式(G0)で表される有機化合物。
- 縮合芳香環が縮合したフロキノキサリン骨格を有する、発光デバイス用材料。
- 赤色または近赤外光を発する発光デバイス用材料であり、
縮合芳香環が縮合したフロキノキサリン骨格を有する、発光デバイス用材料。 - 請求項1乃至15のいずれか一に記載の有機化合物、または請求項16または17に記載の発光デバイス用材料を有する、発光デバイス。
- 一対の電極間に有機化合物を含む層を有し、
前記有機化合物を含む層は、請求項1乃至15のいずれか一に記載の有機化合物、または請求項16または17に記載の発光デバイス用材料を有する、発光デバイス。 - 一対の電極間に有機化合物を含む層を有し、
前記有機化合物を含む層は、発光層を有し、
前記発光層は、請求項1乃至15のいずれか一に記載の有機化合物、または請求項16または17に記載の発光デバイス用材料を有する、発光デバイス。 - 一対の電極間に有機化合物を含む層を有し、
前記有機化合物を含む層は、発光層及び電子輸送層を有し、
前記発光層及び前記電子輸送層のうち少なくとも一方は、請求項1乃至15のいずれか一に記載の有機化合物、または請求項16または17に記載の発光デバイス用材料を有する、発光デバイス。 - 請求項18乃至21のいずれか一に記載の発光デバイスと、
トランジスタ及び基板のうち少なくとも一方と、を有する、発光装置。 - 請求項22に記載の発光装置と、
コネクタ及び集積回路の少なくとも一方と、を有する、発光モジュール。 - 請求項22に記載の発光装置と、
アンテナ、バッテリ、筐体、カメラ、スピーカ、マイク、及び操作ボタンのうち少なくとも一つと、を有する、電子機器。 - 請求項18乃至21のいずれか一に記載の発光デバイスと、
筐体、カバー、及び支持台のうち少なくとも一つと、を有する、照明装置。
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