JP2013539584A - 量子ドットおよびホスト - Google Patents
量子ドットおよびホスト Download PDFInfo
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- JP2013539584A JP2013539584A JP2013520984A JP2013520984A JP2013539584A JP 2013539584 A JP2013539584 A JP 2013539584A JP 2013520984 A JP2013520984 A JP 2013520984A JP 2013520984 A JP2013520984 A JP 2013520984A JP 2013539584 A JP2013539584 A JP 2013539584A
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- quantum dots
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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Abstract
Description
Ar8およびAr9は、互いに独立して、3価の芳香族炭化水素基または3価のヘテロ環基を示し、
X3およびX4は、互いに独立して、O、S、C(=O)、S(=O)、SO2、C(R1)(R2)、Si(R1)(R2)、N(R1)、B(R1)、P(R1)、またはP(=O)(R1)を示し、
X5およびX6は、互いに独立して、N、B、P、C(R1)、またはSi(R1)を示し、
R1およびR2は、互いに独立して、H、ハロゲン、−CN、−NC、−NCO、−NCS、−OCN、−SCN、−C(=O)NR0R00、−C(=O)X、−C(=O)R0、−NH2、−NR0R00、−SH、−SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、任意に置換されていてもよいシリル、または1ないし40個のC原子を有するカルビルもしくはヒドロカルビル(これらは、任意に置換されていてもよく、任意に1個以上のヘテロ原子を含んでいてもよい)から選択される同一のまたは異なる基であり、任意に基R1およびR2はこれらが結合するフルオレン部分を有するスピロ基を形成していてもよく、
Xはハロゲンであり、
R0およびR00は、互いに独立して、H、または任意に1個以上のヘテロ原子を含んでいてもよい、任意に置換されていてもよいカルビルもしくはヒドロカルビル基であり、
さらに式中、
X3およびAr9は、Ar9の芳香族環内で隣接する炭素原子に結合され、
X4およびAr8は、Ar9の芳香族環内で隣接する炭素原子に結合され、
X5およびAr9は、Ar8の芳香族環内で隣接する原子に結合され、
X6およびAr8は、Ar9の芳香族環内で隣接する原子に結合されている)。
Ar’およびAr”は、芳香族炭化水素基またはヘテロ環基を示し;
X7およびX8の一方は、C(=O)またはC(R1)(R2)を示し、他方は、O、S、C(=O)、S(=O)、SO2、C(R1)(R2)、Si(R1)(R2)、N(R1)、B(R1)、P(R1)、またはP(=O)(R1)を示し、
Qは、X9、X9−X10、またはX11=X12であり、
X9およびX10は、互いに独立して、O、S、C(=O)、S(=O)、SO2、C(R1)(R2)、Si(R1)(R2)、N(R1)、B(R1)、P(R1)、またはP(=O)(R1)を示し、
X11およびX12は、互いに独立して、N、B、P、C(R1)、またはSi(R1)を示し、
Zは、−CR1=CR2−または−C≡C−を示し、
zは0または1であり、
R1は、上記にて定義された通りであり、
R2は、上記にて定義された通りである)。
M0は、複数出現する場合、互いに独立して、2ないし40個のC原子を有する芳香族、ヘテロ芳香族、または非芳香族環構造であり(これらは、置換されておらず、または1個以上の同一のもしくは異なる基R1で置換されている)、
K1、2およびYは、複数出現する場合、互いに独立して、Mと共に環構造を形成する架橋基であり(これらは、B(R1)、C(R1)2、Si(R1)2、C=O、C=S、C=Se、C=Te、C=NR1、C=C(R1)2、O、S、S=O、SO2、S(R1)2、N(R1)、P(R1)、P(=O)R1、P(=S)R1、C≡C、またはこれらの基の1、2、3、もしくは4個の組合せから選択される)、
Jは、ポリマーへの結合基であり、置換されたまたは置換されていないC−C二重または三重結合、置換された芳香族またはヘテロ芳香族または非芳香族環の環構造であって2ないし40個のC原子を有するもの(これらは、置換されておらず、または1個以上の同一のもしくは異なる基R1で置換される)であってもよく、
R1は、式1で定義された通りであり、
x、y、pは、複数出現する場合、互いに独立して0または1であり、但し、xおよびyの少なくとも一方は1であることを条件とし、
qは、整数≧1である)。
D−B−A 式(5)
(式中、Aは、QD表面に固定されるアンカー基、例えばチオール基であり;Bは、好ましくはアルキル、アルコキシ基から選択されるスペーサであり;Dは、−5.7eVより高い、より好ましくは−5.5eVより高い、非常に好ましくは−5.3eVより高いHOMOを有する有機官能基である)。
Ar4−(Ar5)p−Ar6 式(13)
(式中、
Ar4、Ar5、Ar6は、出現する毎に、同一のまたは異なった、1個以上の基により置換されていてもよい5ないし30個の芳香族環原子を有するアリールまたはヘテロアリール基であり、
pは、1、2、または3であり、
Ar4、Ar5、およびAr6中のπ電子の合計は、p=1の場合に少なくとも30であり、p=2の場合は少なくとも36であり、p=3の場合は少なくとも42である)。
[M(L)2]n 式(40)
(式中、M、L、およびnは、参考文献のように定義される)。好ましくは、MはZnであり、Lはキノリネートであり、nは2、3、または4である。[Znq2]2、[Znq2]3、および[Znq2]4が、特に非常に好ましい。
− 任意に、第1の基材、
− アノード層、
− 電荷発生層または正孔注入層、
− 任意に、電子および/または励起子遮断層、
− 上記および下記の量子ドットおよび有機ホストを含む活性層、
− 任意に、正孔および/または励起子遮断層、
− 任意に、電子輸送層、
− 任意に、電子注入層または緩衝層、
− カソード層、
− 任意に、第2の基材。
適切で好ましい有機溶媒の例には、ジクロロメタン、トリクロロメタン、モノクロロベンゼン、o−ジクロロベンゼン、テトラヒドロフラン、アニソール、モルホリン、トルエン、o−キシレン、m−キシレン、p−キシレン、1,4−ジオキサン、アセトン、メチルエチルケトン、1,2−ジクロロエタン、1,1,1−トリクロロエタン、1,1,2,2−テトラクロロエタン、酢酸エチル、酢酸n−ブチル、ジメチルホルムアミド、ジメチルアセトアミド、ジメチルスルホキシド、テトラリン、デカリン、インダン、および/またはこれらの混合物が含まれるが、これらに限定するものではない。溶液中の混合物の濃度は、好ましくは0.1ないし10重量%、より好ましくは0.5ないし5重量%である。任意で溶液は、WO 2005/055248 A1に記載されるように、レオロジー特性を調節するために1以上の結合剤も含む。
1)QDの大部分または全てがナノ液滴(不連続層)に、かつ有機発光体およびさらなる機能性化合物の大部分または全てが連続相に;
2)QD、有機発光体、およびホスト材料の大部分または全てがナノ液滴に、かつさらなる機能性化合物、例えば共ホスト材料またはETMまたはHTMの大部分または全てが連続相にある。
例1
材料
以下の材料を、例として本発明で使用する。
本発明で使用される材料および本発明によるQD−LEDに適切ないくつかのさらなる材料のエネルギー準位。
溶液からのQD−LEDの調製
図1に示される構造を備えたQD−LEDを、下記の手順に従い調製する:
1)1×10-7mbarのベース圧力で、真空システム内での熱蒸着により、ITOでコーティングされたガラス基板上のHILとして10nmのWO3を堆積する。
3)デバイスを加熱して、残留溶媒を180℃で10分間除去する。;
4)1×10-7mbarのベース圧力で、真空システム内での熱蒸着により、ETL(または緩衝層)として30nmのTMMを堆積する。
測定および結果の比較
QD−LEDを社内で特性評価し、以下の性質を記録した:VIL特性、ELスペクトル、および色座標、効率、駆動電圧。
Claims (20)
- カソードと、アノードと、発光層と、前記アノードと前記発光層との間に堆積された正孔注入層または電荷発生層とを含む電子デバイスであって、前記発光層は少なくとも1つの量子ドットと少なくとも1つの有機ホスト材料とを含むことを特徴とする電子デバイス。
- 請求項1に記載の電子デバイスであって、前記電荷発生層または正孔注入層は5.6eVより高い、好ましくは6.0eVより高い仕事関数または電子親和力を有する、および/または前記正孔注入層または電荷発生層は遷移金属酸化物、酸化バナジウム(VOx)、酸化モリブデン(MoOx)、酸化ルテニウム(RuOx)および酸化タングステン(WOx)から選択される少なくとも1つの要素を含むことを特徴とする電子デバイス。
- 請求項1または2に記載の電子デバイスであって、前記量子ドットのイオン化ポテンシャルもしくは価電子帯(VB)が前記有機ホストのHOMOより少なくとも0.3eV、好ましくは0.4eV、特に好ましくは0.5eV高い、または前記量子ドットの電子親和力もしくは伝導帯が前記ホスト材料のLUMOより少なくとも0.3eV、好ましくは0.4eV、特に好ましくは0.5eV低いことを特徴とする電子デバイス。
- 請求項1ないし3のいずれか1項に記載の電子デバイスであって、前記ホスト材料は、前記量子ドットより大きなバンドギャップを有するホスト材料、少なくとも−5.7eVより低いHOMOを有する有機化合物、および少なくとも−3.0eVより低いLUMOを有する有機化合物から選択される少なくとも1つの要素であることを特徴とする電子デバイス。
- 請求項1ないし4のいずれか1項に記載の電子デバイスであって、前記量子ドットは−5.7eVより高い、好ましくは−5.5eVより高い、非常に好ましくは−5.3eVより高い価電子帯を有することを特徴とする電子デバイス。
- 請求項1ないし5のいずれか1項に記載の電子デバイスであって、前記量子ドットは、II−VI族、III−V族、IV−VI族、およびIV族半導体、好ましくはZnO、ZnS、ZnSe、ZnTe、CdS、CdSe、CdTe、HgS、HgSe、HgTe、MgS、MgSe、GeS、GeSe、GeTe、SnS、SnSe、SnTe、PbO、PbS、PbSe、PbTe、GaN、GaP、GaAs、GaSb、InN、InP、InAs、InSb、AlN、AlP、AlAs、AlSb、GaN、GaP、GaAs、GaSb、および2以上のこのような半導体の適切な組合せから選択される少なくとも1つの要素を含む、および/またはこれらのコア/シェル、コアマルチシェル層状構造をもつことを特徴とする電子デバイス。
- 請求項1ないし6のいずれか1項に記載の電子デバイスであって、前記量子ドットの濃度が、前記量子ドットが前記有機ホスト内で正孔トラップまたは電子トラップとして作用するように、好ましくは0.5ないし20体積%、非常に好ましくは1ないし15体積%、最も好ましくは2ないし10体積%に選択されることを特徴とする電子デバイス。
- 請求項1ないし7のいずれか1項に記載の電子デバイスであって、少なくとも1つのさらなる有機発光体、または前記量子ドットの発光スペクトルと重なる吸収スペクトルをもつ少なくとも1つのさらなる有機発光体を含む電子デバイス。
- 少なくとも1つの量子ドットと1つの有機ホストとを含む混合物であって、前記量子ドットのイオン化ポテンシャルまたは価電子帯が、前記有機ホストのHOMOより少なくとも0.3eV、好ましくは0.4eV、非常に好ましくは0.5eV高い混合物。
- 請求項9に記載の混合物であって、前記有機ホストは前記量子ドットより大きいバンドギャップを有することを特徴とする混合物。
- 請求項9または10に記載の混合物であって、前記量子ドットは−5.7eVより高い、好ましくは−5.5eVより高い、非常に好ましくは−5.3eVより高い価電子帯(VB)を有する、および/または前記量子ドットは、II−VI族、III−V族、IV−VI族、およびIV族半導体、好ましくはZnO、ZnS、ZnSe、ZnTe、CdS、CdSe、CdTe、HgS、HgSe、HgTe、MgS、MgSe、GeS、GeSe、GeTe、SnS、SnSe、SnTe、PbO、PbS、PbSe、PbTe、GaN、GaP、GaAs、GaSb、InN、InP、InAs、InSb、AlN、AlP、AlAs、AlSb、GaN、GaP、GaAs、GaSb、および2以上のこのような半導体の適切な組合せから選択される少なくとも1つの要素を含む、および/またはこれらのコア/シェル、コアマルチシェルの層状構造をもつことを特徴とする混合部。
- 請求項9ないし11のいずれか1項に記載の混合物であって、前記有機ホストは、少なくとも−6.0eVより低いHOMOを有する有機化合物、小分子および/またはポリマーから選択される少なくとも1つの要素であることを特徴とする混合物。
- 請求項9ないし12のいずれか1項に記載の混合物であって、前記量子ドットの濃度が、前記量子ドットが前記有機ホスト内で正孔トラップとして作用するように、好ましくは0.5ないし30重量%、非常に好ましくは1ないし20重量%、最も好ましくは5ないし15重量%に選択されることを特徴とする混合物。
- 請求項9ないし13のいずれか1項に記載の混合物であって、少なくとも1つのさらなる発光体、または前記量子ドットの発光スペクトルに重なる吸収スペクトルをもつ少なくとも1つのさらなる発光体を含む、および/または前記少なくとも1つのさらなる発光体は有機化合物または他の量子ドットから選択される混合物。
- 好ましくは−5.7eVより高い、非常に好ましくは−5.5eVより高い、最も好ましくは−5.3eVより高いHOMOを有する正孔輸送単位を有するキャップを含む量子ドット。
- 請求項15に記載の量子ドットであって、前記正孔輸送単位は、小分子正孔輸送材料、アミン、トリアリールアミン、チオフェン、カルバゾール、フタロシアニン、ポルフィリン、これらの異性体および誘導体から選択される少なくとも1つの基を含むことを特徴とする量子ドット。
- 請求項15または16に記載の量子ドットを調製するための方法であって、前記量子ドットを配位子交換によって形成することを特徴とする方法。
- 請求項9ないし14のいずれか1項に記載の混合物、または請求項15または16に記載の量子ドットを含む、またはアノードと、カソードと、前記アノードと前記カソードとの間の機能層とを含み、前記機能層が請求項9ないし14のいずれか1項に記載の混合物、または請求項15もしくは16に記載の量子ドットを含む電子デバイス。
- 請求項1ないし8または18のいずれか1項に記載の電子デバイスであって、前記デバイスが発光デバイス、光変換デバイス、集光デバイス、光起電力デバイス、フォトダイオード、光センサデバイス、有機発光ダイオード(OLED)、ポリマー発光ダイオード(PLED)、有機発光電気化学セル、有機電界効果トランジスタ(OFET)、薄膜トランジスタ(TFT)、有機太陽電池(O−SC)、有機レーザダイオード(O−laser)、有機集積回路(O−IC)、無線認証(RFID)タグ、光検出器、センサ、論理回路、メモリ素子、キャパシタ、電荷注入層、ショットキーダイオード、平坦化層、帯電防止膜、伝導性基材またはパターン、光導電体、電子写真用素子、有機発光トランジスタ(OLET)、有機スピントロニックデバイス、および有機プラズモン発光デバイス(OPED)から選択され、好ましくは有機発光ダイオードから選択されることを特徴とする電子デバイス。
- 請求項9ないし14のいずれか1項に記載の混合物、または請求項15もしくは16に記載の量子ドットを含む、配合物、特に溶液、分散液、またはエマルジョン。
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EP2599141B1 (en) | 2019-12-11 |
JP6382259B2 (ja) | 2018-08-29 |
US20130214249A1 (en) | 2013-08-22 |
US9093656B2 (en) | 2015-07-28 |
WO2012013272A1 (en) | 2012-02-02 |
JP2016197601A (ja) | 2016-11-24 |
EP2599141A1 (en) | 2013-06-05 |
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