JP2010526902A - ホスト及びドーパント機能をもつ有機金属化合物 - Google Patents
ホスト及びドーパント機能をもつ有機金属化合物 Download PDFInfo
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- JP2010526902A JP2010526902A JP2010507385A JP2010507385A JP2010526902A JP 2010526902 A JP2010526902 A JP 2010526902A JP 2010507385 A JP2010507385 A JP 2010507385A JP 2010507385 A JP2010507385 A JP 2010507385A JP 2010526902 A JP2010526902 A JP 2010526902A
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Abstract
Description
で表される、発光性コアに連結された1つ以上の分枝を含む有機金属化合物を提供する。
一般に、OLEDは、アノードとカソードとの間に配置され且つこれらに電気的に接続された少なくとも1つの有機層を含む。電流が流れると、有機層(複数であってもよい)に、アノードはホールを注入し、カソードは電子を注入する。注入されたホールと電子はそれぞれ、反対に帯電した電極に向かって移動する。電子とホールが同じ分子に局在するとき、「励起子」(励起エネルギー状態を有する局在化した電子-ホール対である)が形成される。励起子が光放出機構により緩和するときに光が放射される。いくつかの場合には、励起子はエキシマーまたはエキシプレックスに局在化されることがある。非放射機構、例えば熱緩和も起こり得るが、一般には望ましくないと考えられている。
化合物A、B、及びC(以下に示す)を合成した。図9は化合物A及びBの合成を示す。図10は化合物Cの合成を示す。
例示デバイス1〜12を、本発明の化合物を用いて作製した。これらのデバイスは、窒素中でのスピンコーティングと高真空(<10−7Torr)熱蒸着によって作製した。アノード電極は約1200Åのインジウムスズ酸化物(ITO)であり、カソードは10ÅのLiFとそれに続く1000ÅのAlであった。全てのデバイスは、作製後すぐに窒素グローブボックス中(<1ppmのH2O及びO2)においてエポキシ樹脂で封止したガラス蓋と、そのパッケージ内に組み込んだ吸湿剤とを用いて密封した。
Claims (39)
- 下記式で表される、発光性コアに連結された1つ以上の分枝を含む有機金属化合物。
各分枝は前記の複数の配位子の1つに連結されており;
変数「y」は1〜3の整数値を有し;
各変数「x」は独立に少なくとも2の整数値を有し;
各変数「n」は独立に0以上の整数値を有し;
各変数「m」は独立に1以上の整数値を有し;
各ホスト残基RHは独立に、少なくとも2つの環を有するアリール基又は少なくとも2つの環を有するヘテロアリール基であり;
各末端基RTは独立に、アルキル基、ヘテロアルキル基、アリール基、及びヘテロアリール基からなる群から選択され;
R1及びR2のそれぞれは、それらの各環の任意の位置にある1つ以上の独立して選択された置換基を表し、前記置換基のそれぞれは独立に、アルキル基、ヘテロアルキル基、アリール基、及びヘテロアリール基からなる群から選択される。) - 上記の鎖の中のなかの各フェニル単位が、それに隣り合ったフェニル単位とメタ配置で連結されている、請求項1記載の有機金属化合物。
- 前記発光性コアが、下記式:
Lは、Mに配位した複数の配位子のうちの1つ又は複数であり;
「p」は前記金属Mの形式酸化状態であり;
変数「q」は1〜「p」の整数値を有し;
A及びBは、それぞれ5又は6員芳香環であり、A−Bは、環Aの窒素原子と環Bのsp2混成炭素原子とを介してMに配位した、芳香環の結合したペアを表し;
環A及び環Bのそれぞれは任意選択でそれぞれR3基及びR4基で置換されていてもよく、R3及びR4のそれぞれは、それら各環上の任意の位置にある1つ又は複数の独立に選択された置換基を表し、各置換基は縮合しているか又はそれらの各環に連結しており、それぞれの置換基は独立に、アルキル基、ヘテロアルキル基、アリール基、及びヘテロアリール基からなる群から選択され;
前記分枝の1つ以上が、環A、環B、又はその両方と連結されている。)
によって表される、請求項1記載の有機金属化合物。 - 環Aがキノリン又はイソキノリンであり、環Bがフェニルである、請求項3に記載の有機金属化合物。
- 変数「q」が2であり、Lがアセチルアセトナート又はアセチルアセトナートの誘導体である、請求項5に記載の有機金属化合物。
- 前記分枝の1つがLに連結している、請求項6に記載の有機金属化合物。
- 各RHが独立に3〜6の環を有する、請求項1に記載の有機金属化合物。
- 各RHが独立に、カルバゾール、トリフェニレン、フェナントレン、フェナントロリン、及びそれらの誘導体からなる群から選択される、請求項1に記載の有機金属化合物。
- 各変数「x」が独立に2〜7の範囲である、請求項1に記載の有機金属化合物。
- 各分枝中のポリフェニレン鎖が4〜14のフェニル単位を含む、請求項1に記載の有機金属化合物。
- 前記発光性コアの分子量が、ホスト残基RHをもつ全ての分枝の分子量の合計の15%〜100%である、請求項1に記載の有機金属化合物。
- 前記発光性コアの分子量が、ホスト残基RHをもつ全ての分枝の分子量の合計の0〜30%である、請求項1に記載の有機金属化合物。
- 前記有機金属化合物が、10mlの有機溶媒中に少なくとも0.01gの溶解度を有する、請求項1記載の有機金属化合物。
- 前記金属原子がイリジウムである、請求項1記載の有機金属化合物。
- アノード;
カソード;及び
前記アノードと前記カソードとの間に配置された第一の有機層
を含み、前記第一の有機層が下記式:
各分枝は前記の複数の配位子の1つに連結されており;
変数「y」は1〜3の整数値を有し;
各変数「x」は独立に少なくとも2の整数値を有し;
各変数「n」は独立に0以上の整数値を有し;
各変数「m」は独立に1以上の整数値を有し;
各ホスト残基RHは独立に、少なくとも2つの環を有するアリール基又は少なくとも2つの環を有するヘテロアリール基であり;
各末端基RTは独立に、アルキル基、ヘテロアルキル基、アリール基、及びヘテロアリール基からなる群から選択され;
R1及びR2のそれぞれは、それらの各環の任意の位置にある1つ以上の独立して選択された置換基を表し、前記置換基のそれぞれは独立に、アルキル基、ヘテロアルキル基、アリール基、及びヘテロアリール基からなる群から選択される。)
を有する有機金属化合物を含む、有機電子デバイス。 - 前記第一の有機層がエレクトロルミネッセンス層である、請求項19に記載のデバイス。
- 前記第一の有機層が、前記有機金属化合物とは別個且つ明確なホスト材料をさらに含む、請求項20に記載のデバイス。
- 前記デバイスが有機発光ダイオードである、請求項19に記載のデバイス。
- 前記第一の有機層が溶液法によって形成される、請求項19に記載のデバイス。
- 前記第一の有機層と前記アノードとの間に配置された第二の有機層をさらに含み、前記第二の有機層が正孔注入材料を含む、請求項19に記載のデバイス。
- 前記第二の有機層と前記第一の有機層との間に配置された第三の有機層をさらに含み、前記第三の有機層が正孔輸送材料を含む、請求項24に記載のデバイス。
- 前記第一の有機層と前記カソードとの間に配置された第四の有機層をさらに含み、前記第四の有機層が電子輸送材料を含む、請求項25に記載のデバイス。
- 前記第四の有機層と前記カソードとの間に配置された第五の有機層をさらに含み、前記第五の有機層が電子輸送材料を含む、請求項26に記載のデバイス。
- 基材上に配置された第一の電極を準備する工程;
前記第一の電極の上に第一の有機層を形成し、前記第一の有機層が有機金属化合物を含む工程;及び、
前記第一の有機層の上に配置された第二の電極を形成する工程を含み、
前記有機金属化合物が下記式:
各分枝は前記の複数の配位子の1つに連結されており;
変数「y」は1〜3の整数値を有し;
各変数「x」は独立に少なくとも2の整数値を有し;
各変数「n」は独立に0以上の整数値を有し;
各変数「m」は独立に1以上の整数値を有し;
各ホスト残基RHは独立に、少なくとも2つの環を有するアリール基又は少なくとも2つの環を有するヘテロアリール基であり;
各末端基RTは独立に、アルキル基、ヘテロアルキル基、アリール基、及びヘテロアリール基からなる群から選択され;
R1及びR2のそれぞれは、それらの各環の任意の位置にある1つ以上の独立して選択された置換基を表し、前記置換基のそれぞれは独立に、アルキル基、ヘテロアルキル基、アリール基、及びヘテロアリール基からなる群から選択される。)
を有する、有機電子デバイスの製造方法。 - 前記第一の有機層を形成する工程が、前記有機金属化合物を溶液法によって堆積させる工程を含む、請求項28に記載の方法。
- 前記第一の電極の上に第二の有機層を形成させて、前記第二の有機層を前記第一の有機層と前記第一の電極との間に配置することをさらに含む、請求項28に記載の方法。
- 前記第二の有機層を形成する工程が、溶液法によって堆積させる工程を含む、請求項30に記載の方法。
- 前記第二の有機層が正孔注入材料を含む、請求項30に記載の方法。
- 前記第二の有機層を架橋させる工程をさらに含む、請求項31に記載の方法。
- 前記第二の有機層の上に第三の有機層を形成させて、前記第三の有機層を前記第二の有機層と前記第一の有機層との間に配置する工程をさらに含み、前記第三の有機層が正孔輸送材料を含む、請求項30に記載の方法。
- 前記第三の有機層を形成させる工程が、溶液法によって堆積させる工程を含む、請求項34に記載の方法。
- 前記第三の有機層を架橋する工程をさらに含む、請求項35に記載の方法。
- 前記第一の有機層の上に第四の有機層を堆積させる工程をさらに含み、前記第四の有機層は前記第一の有機層と前記カソードとの間に配置され、前記第四の有機層が電子輸送材料を含む、請求項34に記載の方法。
- 前記第四の有機層が真空熱蒸着によって堆積される、請求項37に記載の方法。
- 前記第四の有機層の上に第五の有機層を堆積させる工程をさらに含み、前記第五の有機層は前記第四の有機層と前記カソードとの間に配置され、前記第五の有機層が電子輸送材料を含む、請求項37に記載の方法。
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KR101969895B1 (ko) | 2019-04-17 |
US7993763B2 (en) | 2011-08-09 |
KR101866546B1 (ko) | 2018-06-08 |
TWI628259B (zh) | 2018-07-01 |
CN114920781A (zh) | 2022-08-19 |
US20080280163A1 (en) | 2008-11-13 |
TW200907018A (en) | 2009-02-16 |
EP2142559B1 (en) | 2016-12-21 |
KR20180064562A (ko) | 2018-06-14 |
JP5587176B2 (ja) | 2014-09-10 |
KR20150140874A (ko) | 2015-12-16 |
WO2008140657A1 (en) | 2008-11-20 |
CN106380489A (zh) | 2017-02-08 |
KR20100016367A (ko) | 2010-02-12 |
CN106380489B (zh) | 2022-02-01 |
EP2142559A1 (en) | 2010-01-13 |
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