JP2006522487A - 発光材料として二核金属化合物を利用する有機発光デバイス - Google Patents
発光材料として二核金属化合物を利用する有機発光デバイス Download PDFInfo
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Abstract
Description
Yは、C、N、S、およびPからなるグループから選択され;
Rは、Hまたは何らかの有機物置換基であり;そして、
NおよびN’は、4〜8の員環数(member)を持つ炭化水素鎖であって、望ましくは、ヘテロ原子を含む。
ここで使用されるように、材料に対する略称は以下の通りである:
CBP: 4,4’−N,N−ジカルバゾール−ビフェニル
m−MTDATA:4,4’,4”−トリス(3−メチルフェニルフェンリアミノ)トリ
フェニルアミン
Alq3: 8−トリス−ヒドロキシキノリン・アルミニウム
Bphen: 4,7−ジフェニル−1,10−フェナントロリン
n−BPhen: nドーピングしたBPhen(リチウムでドーピング)
F4−TCNQ: テトラフルオロ−テトラシアノ−キノジメタン
p−MTDATA:pドーピングしたm−MTDATA(F4−TCNQでドーピング)
Ir(ppy)3 :トリス(2−フェニルピリジン)−イリジウム
Ir(ppz)3 :トリス(1−フェニルピラゾラト,N,C(2’)イリジウム(III
)
BCP: 2,9−ジメチル−4,7−ジフェニル−1,10−フェナントロリ
ン
TAZ: 3−フェニル−4−(1’−ナフチル)−5−フェニル−1,2,4
−トリアゾール
CuPc: 銅フタロシアニン
ITO: インジウムすず酸化物
NPD: ナフチル−フェニル−ジアミン
TPD: N,N’−ビス(3−メチルフェニル)−N,N’−ビス−(フェニ
ル)ベンジジン
BAlg: アルミニウム(III)ビス(2−メチル−8−キノリナト)4−フ
ェニルフェノレート
mCP: 1,3−N,N−ジカルバゾール−ベンゼン
DCM: 4−(ジシアノエチレン)−6−(4−ジメチルアミノスチリル−2
−メチル)−4H−ピラン
DMQA: N,N’−ジメチルキナクリドン
PEDOT:PSS:ポリ(3,4−エチレンジオキシチオフェン)とポリスチレンスル
ホン酸(PSS)の水分散液
FPt: 白金(II)(2−(4−,6−ジフルオロフェニル)ピリジナト−
N,C2)(2,4−ペンタンジオナト−O,O)
FPtdpm: 白金(II)(2−(4−,6−ジフルオロフェニル)ピリジナト−
N,C2)(2,2,6,6−テトラメチル−3,5−ヘプタンジオナ
ト−O,O)
(F2ppy)2Pt2(SPy)2:ジ−白金(II),ビス(2−(4−,6−ジフルオ
ロフェニル)ピリジナト−N,C2)ビス[μ−(2−ピリジンチオナ
ト−N1:S2)]
Pt2Spy4: ジ−白金(II),テトラキス[μ−(2−ピリジンチオナト−N1
:S2)
Spy: 2−チオピリジン
さて、本発明の特定の代表的な実験例を、そのような実験例をどのように成されるかを含めて説明する。特定の方法、材料、条件、処理パラメータ、デバイスなどは、必ずしも本発明の範囲を制限しない、ということが理解される。
2メルカプトピリジン(0.53g、4.80mmol)を、参考としてその全体が組み込まれているBrooksら著,「Synthesis and Characterization of Phosphorescent Cyclometalated Platinum Complexes」,Inorganic Chemistry,2002年,41 (12),3055-3066に開示されたような、4,6−dfppy白金ダイマー(dimer)(2.00g、2.38mmol)のメタノール溶液に追加した。炭酸カリウム(0.50g)をその溶液に追加し、18時間の間60℃に加熱した。次に、その溶液を冷却し、減圧下で溶剤を取り除いた。未精製の生成物をアセトンに溶かし、溶離剤としてのアセトンと共にシリカゲル・コラムに通した。溶剤をもう一度減圧下で取り除き、メタノールから生成物を再結晶させ、82%収率で(F2ppy)2Pt2(SPy)2を赤い結晶化合物として生じさせた。
ガラス基板を洗浄剤で洗浄し、脱イオン水で、続いてアセトンですすぐことによって準備した。次に、ガラスを、窒素の流れの下で乾燥し、次に、オゾン・オーブン中に10分間置いた。100ml計量フラスコ中のトルエンに5.00mgの(F2ppy)2Pt2(SPy)2と100mgのCBPを溶解して(F2ppy)2Pt2(SPy)2/CBPの100mlの溶液を準備した(溶液A)。100ml計量フラスコ中のトルエンに5.00mgのFPtと100mlのCBPを溶解してFPt/CBPの100ml溶液を準備した(溶液B)。2つの薄膜をこれらの溶液から準備した。溶液Aを、40秒間、40000rpmでガラス基板上にスピンコートし、(F2ppy)2Pt2(SPy)2薄膜を得た。溶液Bを、40秒間、40000rpmで他のガラス基板上にスピンコートし、FPt薄膜を得た。
100nm程度の厚さの20Ω/□のシート抵抗を持ったインジウムすず酸化物(ITO)を用いて、予め被覆したガラス基板上に有機発光デバイスを成長させた。基板を溶剤で脱脂し、次に、UVオゾン環境に10分間さらして清浄化した。清浄化の後、直ちに基板をベース圧力約1x10−6Torrで作動する熱蒸散システムに設置した。いくつかの異なったデバイス構成を図6および図8で示されるように作製した。第1に、400Å厚さの4−4’−ビス[N−(1−ナフチル)−N−フェニル−アミノ]ビフェニル(α−NPD)正孔輸送層(HTL)を蒸着した。いくつかのデバイスでは、200Å厚さのmCPの層を電子障壁層(EBL)として蒸着した。次に、9%(重量比)の(F2ppy)2Pt2(SPy)2をmCPかCBPのどちらかと共に蒸着して、300Å厚さの発光層を形成した。いくつかのデバイスでは、120Å厚さのBCPの層を電子障壁層(EBL)として蒸着した。最終的に、ジルコニウム(IV)テトラ(8−ヒドロキシキノリン)(Zrq4)からなる350Å厚さの電子輸送層(ETL)を蒸着した。10Å厚さのLiFの層からなるデバイスカソードに続いて1000Å厚さのアルミニウムの層をシャドウマスクによって蒸着した。デバイス活性面積は2×2mm2であった。以下の4つの構成が作製された:
構成1:ITO/NPD/(F2ppy)2Pt2(SPy)2:CBP/ZrQ4/LiF:Al
構成2:ITO/NPD/(F2ppy)2Pt2(SPy)2:CBP/BCP/ZrQ4/
LiF:Al
構成3:ITO/NPD/(F2ppy)2Pt2(SPy)2:mCP/ZrQ4/LiF:Al
構成4:ITO/NPD/mCP/(F2ppy)2Pt2(SPy)2:mCP/ZrQ4/
LiF:Al
110 基板
115 アノード
120 正孔注入層
125 正孔輸送層
130 正孔輸送層
130 電子障壁層
135 発光層
140 正孔障壁層
145 電子輸送層
150 電子注入層
155 保護層
160 カソード
162 金属層
164 導電性金属酸化物層
200 デバイス(OLED)
210 基板
215 カソード
220 発光層
225 正孔輸送層
230 アノード
615 アノード
625 正孔輸送層
635 発光層
640 正孔障壁層
645 電子輸送層
660 カソード
1115 アノード
1125 正孔輸送層
1130 電子障壁層
1135 発光層
1145 電子輸送層
1160 カソード
Claims (38)
- アノードと、
カソードと、
前記アノードおよび前記カソードの間に配置され、かつ電気的に接続された発光層であって、さらに、
d7、d8、およびd9金属からなるグループから選択された第1の中心金属、
d7、d8、およびd9金属からなるグループから選択された第2の中心金属、および
前記第1の中心金属と前記第2の中心金属に配位された架橋配位子、を含む発光材料を備えた発光層と、
を有することを特徴とする有機発光デバイス。 - 前記第1の中心金属および前記第2の中心金属はd8金属からなるグループから共に選択されることを特徴とする請求項1に記載のデバイス。
- 前記第1の中心金属と前記第2の中心金属の間の距離は、前記第1の中心金属のd8軌道と前記第2の中心金属におけるd8軌道との間に、大きな重なりがあるようなものであることを特徴とする請求項2に記載のデバイス。
- 前記第1の中心金属と前記第2の中心金属は共に同一の金属であることを特徴とする請求項2に記載のデバイス。
- 前記第1の中心金属と前記第2の中心金属は共にPtであることを特徴とする請求項4に記載のデバイス。
- 前記発光材料は、
第1の中心金属、
第2の中心金属、および
4つの架橋配位子であって、各架橋配位子が前記第1の中心金属および前記第2の中心金属に配位する架橋配位子、
を含む二核材料であることを特徴とする請求項1に記載のデバイス。 - 前記発光材料は、
第1の中心金属、
第2の中心金属、
2つの架橋配位子であって、各架橋配位子が前記第1の中心金属および前記第2の中心金属に配位する架橋配位子、
前記第1の中心金属に結合された第1の二座の光活性な配位子、および
前記第2の中心金属に結合された第2の二座の光活性な配位子、
を含む二核材料であることを特徴とする請求項1に記載のデバイス。 - 前記第1の光活性な配位子および前記第2の光活性な配位子は前記架橋配位子によって近接して保持され、前記第1および第2の中心金属は前記第1および第2の光活性な配位子間の大きなπ−π相互作用を可能にすることを特徴とする請求項7に記載のデバイス。
- 前記第1および第2の光活性な配位子は同一の構造を持つことを特徴とする請求項8に記載のデバイス。
- 前記発光材料は、
第1の中心金属、
第2の中心金属、
1つの架橋配位子であって、その架橋配位子が前記第1の中心金属および前記第2の中心金属に配位する架橋配位子、
前記第1の中心金属に結合された第1の三座の光活性な配位子、および
前記第2の中心金属に結合された第2の三座の光活性な配位子、
を含む二核材料であることを特徴とする請求項1に記載のデバイス。 - 前記第1の光活性な配位子および前記第2の光活性な配位子は前記架橋配位子によって近接して保持され、前記第1および第2の中心金属は前記第1および第2の光活性な配位子間の大きなπ−π相互作用を可能にすることを特徴とする請求項10に記載のデバイス。
- 前記第1および第2の光活性な配位子は同一の構造を持つことを特徴とする請求項11に記載のデバイス。
- 前記発光層はさらにホスト材料を有し、前記発光材料がホスト材料内のドーパントとして存在していることを特徴とする請求項1に記載のデバイス。
- アノードと、
正孔輸送層と、
電子輸送層と、
カソードと、
発光層であって、前記発光層が前記正孔輸送層と前記電子輸送層との間に配置される発光層と、
を有することを特徴とする請求項1に記載のデバイス。 - デバイスから放たれたほぼ全ての前記デバイスの光がエキシマ発光から生じることを特徴とする請求項1に記載のデバイス。
- 前記発光分子は燐光性の発光材料であることを特徴とする請求項1に記載のデバイス。
- NおよびN’がヘテロ原子を含むことを特徴とする請求項19に記載のデバイス。
- 前記第1の中心金属と第2の中心金属との間の距離は約4オングストローム未満であることを特徴とする請求項1に記載のデバイス。
- 前記第1の中心金属と第2の中心金属との間の距離は約2.5オングストロームから約2.8オングストロームであることを特徴とする請求項22に記載のデバイス。
- 前記発光材料は光活性な配位子を含まないことを特徴とする請求項1に記載のデバイス。
- アノードと、
カソードと、
前記アノードおよび前記カソードの間に配置され、かつ電気的に接続された発光層であって、さらに、
少なくとも3配位数をもつ第1の中心金属、
少なくとも3配位数をもつ第2の中心金属、および
前記第1の中心金属と前記第2の中心金属に配位された架橋配位子、を含む二核発光材料を備えた発光層と、
を有することを特徴とする有機発光デバイス。 - 前記第1の中心金属および前記第2の中心金属は共に少なくとも4配位数を持つことを特徴とする請求項25に記載のデバイス。
- 前記第1の中心金属および前記第2の中心金属は共に4配位数を持つことを特徴とする請求項26に記載のデバイス。
- 前記発光材料は光活性な配位子を含まないことを特徴とする請求項25に記載のデバイス。
- 前記第1の中心金属および前記第2の中心金属は同一の配位数を有し、
前記発光材料は、前記第1の中心金属および前記第2の中心金属に配位された複数の架橋配位子をさらに有し、前記架橋配位子の数は前記第1の中心金属の配位数と等しいようなものであることを特徴とする請求項25に記載のデバイス。 - アノードと、
カソードと、
前記アノードおよび前記カソードの間に配置され、かつ電気的に接続された発光層であって、さらに、
第1の中心金属、
第2の中心金属、
前記第1の中心金属および前記第2の中心金属に配位された架橋配位子、
前記第1の中心金属に結合された第1の光活性な配位子、および
前記第2の中心金属に結合された第2の光活性な配位子、を含む二核発光材料を備えた発光層と、
を有することを特徴とする有機発光デバイス。 - NおよびN’がヘテロ原子を含むことを特徴とする請求項33に記載のデバイス。
- アノードと、
カソードと、
前記アノードおよび前記カソードの間に配置され、かつ電気的に接続された発光層であって、さらに、
第1の中心金属、
第2の中心金属、および
前記第1の中心金属と前記第2の中心金属に配位された架橋配位子、を含む二核発光材料を備えた発光層と、
を有し、
前記二核発光材料が電気的に中性であることを特徴とする有機発光デバイス。 - アノードと、
カソードと、
前記アノードおよび前記カソードの間に配置され、かつ電気的に接続された発光層であって、さらに、
第1の中心金属、
第2の中心金属、および
前記第1の中心金属と前記第2の中心金属に配位された架橋配位子、を含む二核発光材料を備えた発光層と、
を有し、
前記中心金属が前記架橋配位子によってコフェイシャル形態に保持されることを特徴とする有機発光デバイス。 - 前記第1および第2の中心金属はそれぞれ正方平面状形態を持つことを特徴とする請求項36に記載のデバイス。
- アノードと、
カソードと、
前記アノードおよび前記カソードの間に配置され、かつ電気的に接続された発光層であって、さらに、
40に等しいかまたはそれ以上の原子番号を持つ金属からなるグループから選択された第1の中心金属、
40に等しいかまたはそれ以上の原子番号を持つ金属からなるグループから選択された第2の中心金属、
前記第1の中心金属と前記第2の中心金属に配位された架橋配位子、を含む発光材料を備えた発光層と、
を有することを特徴とする有機発光デバイス。
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US10/404,785 US7090928B2 (en) | 2003-04-01 | 2003-04-01 | Binuclear compounds |
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PCT/US2004/009683 WO2004093210A1 (en) | 2003-04-01 | 2004-03-29 | Organic light emitting devices utilizing binuclear metal-compounds as emissive material |
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KR (1) | KR101056477B1 (ja) |
CN (1) | CN1795569B (ja) |
AT (1) | ATE355618T1 (ja) |
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WO2010132416A3 (en) * | 2009-05-12 | 2011-02-03 | E. I. Du Pont De Nemours And Company | Organic electronic device with electron tunneling layer |
JP2012527123A (ja) * | 2009-05-12 | 2012-11-01 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電子トンネル層を有する有機電子デバイス |
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WO2004093210A1 (en) | 2004-10-28 |
JP5384789B2 (ja) | 2014-01-08 |
JP2011109140A (ja) | 2011-06-02 |
CN1795569A (zh) | 2006-06-28 |
TWI354693B (en) | 2011-12-21 |
US20060269785A1 (en) | 2006-11-30 |
JP5730613B2 (ja) | 2015-06-10 |
EP1609197B1 (en) | 2007-02-28 |
DE602004005014T2 (de) | 2007-07-12 |
DE602004005014D1 (de) | 2007-04-12 |
US7090928B2 (en) | 2006-08-15 |
TW200427813A (en) | 2004-12-16 |
CN1795569B (zh) | 2010-09-22 |
US7824778B2 (en) | 2010-11-02 |
KR101056477B1 (ko) | 2011-08-12 |
ATE355618T1 (de) | 2006-03-15 |
EP1609197A1 (en) | 2005-12-28 |
KR20050109618A (ko) | 2005-11-21 |
US20040197600A1 (en) | 2004-10-07 |
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