JP6940258B2 - 有機半導体をドーピングする方法およびドーピング組成物 - Google Patents
有機半導体をドーピングする方法およびドーピング組成物 Download PDFInfo
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- JP6940258B2 JP6940258B2 JP2016140768A JP2016140768A JP6940258B2 JP 6940258 B2 JP6940258 B2 JP 6940258B2 JP 2016140768 A JP2016140768 A JP 2016140768A JP 2016140768 A JP2016140768 A JP 2016140768A JP 6940258 B2 JP6940258 B2 JP 6940258B2
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- H10K71/30—Doping active layers, e.g. electron transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K71/20—Changing the shape of the active layer in the devices, e.g. patterning
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Description
有機半導体は、ポリマー性または非ポリマー性材料であってもよい。好ましくは、有機半導体はポリマーであり、より好ましくは共役ポリマーである。
−アルキル(C1−20アルキルであってもよい)(ここで1つ以上の非隣接C原子は、置換されてもよいアリールまたはヘテロアリール、O、S、C=Oまたは−COO−で置き換えられてもよく、1つ以上のH原子はFで置き換えられてもよい);
−式−(Ar7)rの基(ここで各Ar7は、独立に、非置換または1つ以上の置換基で置換されてもよいアリールまたはヘテロアリール基であり、rは少なくとも1である(1、2または3であってもよい))、好ましくは分岐状または線状鎖のフェニル基(このそれぞれは1つ以上のC1−20アルキル基を有していてもよい)
からなる群から選択されてもよい。
例示的なn−ドーパント試薬は、2,3−ジヒドロ−ベンゾイミダゾール基(2,3−ジヒドロ−1H−ベンゾイミダゾール基であってもよい)を含む。n−ドーパント試薬は、式(I)を有していてもよい:
各R2は、独立に、C1−20ヒドロカルビル基(C1−10アルキル基であってもよい)であり;
R3はHまたはC1−20ヒドロカルビル基(H、C1−10アルキルまたはC1−10アルキルフェニルであってもよい)であり;
各R4は、独立に、C1−20ヒドロカルビル基(C1−10アルキル、フェニルまたは1つ以上のC1−10アルキル基で置換されたフェニルであってもよい)である。
OLED100は、1つ以上の発光層を含有してもよい。
カソードは、1つ以上の層を含んでいてもよい。好ましくは、カソードは、1つ以上の伝導性材料を含むまたはこれらからなる電子注入層と接触した層を含むまたはこれらからなる。例示的な伝導性材料は、金属、好ましくは少なくとも4eVの仕事関数を有する金属(アルミニウム、銅、銀または金または鉄であってもよい)である。例示的な非金属性伝導性材料としては、伝導性金属酸化物、例えばインジウムスズオキシドおよびインジウム亜鉛オキシド、グラファイトおよびグラフェンが挙げられる。金属の仕事関数は、CRC Handbook of Chemistry and Physics,12−114,87th Edition(CRC Press出版、David R.Lide.編)に与えられる。複数の値が金属に与えられている場合、列挙されたうちの最初の値を適用する。
正孔輸送層が、アノード103と発光層105との間に提供されてもよい。
伝導性有機または無機材料から形成され得る伝導性正孔注入層は、図1に示されるようなOLEDのアノード103と発光層105との間に提供されて、アノードから半導体ポリマーの(1または複数の)層への正孔注入を補助してもよい。ドープされた有機正孔注入材料の例としては、置換されてもよいドープされたポリ(エチレンジオキシチオフェン)(PEDT)、特に欧州特許第0901176号明細書および欧州特許第0947123号明細書に開示されるような、電荷平衡ポリ酸、例えばポリスチレンスルホネート(PSS)でドープされたPEDT、ポリアクリル酸またはフッ素化スルホン酸、例えばNafion(登録商標);米国特許第5723873号明細書および米国特許第5798170明細書に開示されるようなポリアニリン;および置換されてもよいポリチオフェンまたはポリ(チエノチオフェン)が挙げられる。伝導性無機材料の例としては、遷移金属酸化物、例えばJournal of Physics D:Applied Physics(1996),29(11),2750−2753に開示されるような、VOx、MoOxおよびRuOxが挙げられる。
n−ドーパント試薬および有機半導体のフィルムは、好ましくは、湿分および酸素の進入を防ぐためにフィルムを含有するデバイスの封入された後に、本明細書に記載されるn−ドーピングを生じるように放射線に曝露される。
発光層105および電子注入層107は、蒸発および溶液堆積方法を含むいずれの方法によって形成されてもよい。溶液堆積方法が好ましい。
ドープされた有機半導体層は、有機発光デバイスの電子注入層を参照して記載されているが、本明細書に記載されるように形成された層は、他の有機電子デバイスにおいて、例えば有機光起電デバイスまたは有機光検出器の電子抽出層として;n型有機薄膜トランジスタの補助電極層としてまたは熱電気発生器のn型半導体として使用されてもよいことが理解される。
プリスチンおよび本明細書で記載されたn−ドープされた受容体材料のUV−可視吸収スペクトルは、ドーパントとのブレンドとして、またはドーパントの上層を用いて、ガラス基材上にスピンコーティングすることによって測定された。フィルム厚さは、20〜100nmの範囲であった。
ソフトウェアを備えたCHI660D Electrochemical workstation(IJ Cambria Scientific Ltd)
CHI 104 3mm Glassy Carbon Disk Working Electrode(IJ Cambria Scientific Ltd)
白金ワイヤ補助電極
参照電極(Ag/AgCl)(Havard Apparatus Ltd)
化学物質
アセトニトリル(Hi−dry無水グレード−ROMIL) (セル溶液溶媒)
トルエン(Hi−dry無水グレード) (サンプル調製溶媒)
フェロセン−FLUKA (参照標準)
テトラブチルアンモニウムヘキサフルオロホスフェート−FLUKA) (セル溶液塩)
サンプル調製
受容体ポリマーを、作用電極上に薄膜(約20nm)として引き伸ばした;ドーパント材料を、トルエン中の希釈溶液(0.3重量%)として測定した。
測定セルは、電解質、ガラス状炭素作用電極(この上にはサンプルが薄膜としてコーティングされている)、白金対電極、およびAg/AgCl参照ガラス電極を含有する。フェロセンは、参照材料(LUMO(フェロセン)=−4.8eV)として実験の終わりにセルに添加する。
n−ドーパントのイオン化は、結果としてイミダゾリウム炭素の形成をもたらす。対応するイミダゾリウムラジカルのSOMO準位を決定するために、カチオンは、酸化走査の間に中性ドーパント分子から最初に生じ、これによりまた中性ドーパント分子のHOMO準位を決定できる。
材料
ドーパント1によるポリマー1およびポリマー2のドーピングを試験した。
ポリマー1およびドーパント1の配合物を、スピンコーティングによってガラス層上に堆積してフィルムを形成し、Enfis Ltd,UK.から入手可能なENFIS UNO Air Cooled Light Engineを用いて2時間465nmのピーク波長を有する光で照射した。
ポリマー2およびドーパント1の配合物をスピンコーティングによってガラス層上に堆積してフィルムを形成し、Enfis Ltd,UK.から入手可能なENFIS UNO Air Cooled Light Engineを用いて2時間465nmのピーク波長を有する光で照射した。
Enfis Ltd,UK.から入手可能なENFIS UNO Air Cooled Light Engineを用いて2時間520nmのピーク波長を有する光でフィルムを照射する以外、ドーピング実施例2にて記載されたように、配合物を堆積して照射した。
以下の構造を有するエレクトロンオンリーデバイスを調製した:
ガラス基材/ITO/ドナー受容体層/Ag
ドナー−受容体層を、o−キシレン中、ポリマー1:ドーパント1(99:1重量%)の1重量%配合物をスピンコーティングして、約100nmの厚さに形成した。カソードは、約100nmの厚さまで銀の蒸発によって形成された。
ポリマー1:ドーパント1比が95:5重量%であり、照射時間が30分であった以外は、デバイス実施例1について記載される通りにエレクトロンオンリーデバイスを調製した。
本発明は一態様において、以下を提供する。
[項目1]
n−ドープされた半導体層を形成する方法であって、ここで有機半導体およびn−ドーパント試薬を含むフィルムは、前記有機半導体の吸収範囲である波長を有する光によって照射され、前記n−ドーパント試薬の吸収最大波長は前記光のいずれかのピーク波長よりも短い、方法。
[項目2]
前記有機半導体の吸収最大波長は400nmを超える、項目1に記載の方法。
[項目3]
前記n−ドーパント試薬の吸収最大波長は350nm以下である、項目1から2のいずれかに記載の方法。
[項目4]
前記光が、400〜700nmの範囲のピーク波長を有する、項目1から3のいずれかに記載の方法。
[項目5]
前記n−ドーパント試薬が(4−(1,3−ジメチル−2,3−ジヒドロ−1H−ベンゾイミダゾール−2−イル)フェニル)ジメチルアミンである、項目1から4のいずれかに記載の方法。
[項目6]
前記有機半導体が、C=N基、ニトリル基、C=O基およびC=S基から選択される結合を含む、項目1から5のいずれかに記載の方法。
[項目7]
前記有機半導体がポリマーである、項目1から6のいずれかに記載の方法。
[項目8]
前記ポリマーが共役ポリマーである、項目7に記載の方法。
[項目9]
前記有機半導体が、真空準位から3.2eV以内の最低空軌道を有する、項目1から8のいずれかに記載の方法。
[項目10]
前記n−ドーパント試薬から誘導されるラジカルの半占軌道準位が、前記有機半導体の最低空軌道準位よりも真空準位からみて、さらに0.5eV以上はなれていない、項目1から9のいずれかに記載の方法。
[項目11]
前記フィルムが、溶液堆積方法によって形成される、項目1から10のいずれかに記載の方法。
[項目12]
前記フィルムが、空気中で形成される、項目1から11のいずれかに記載の方法。
[項目13]
前記有機半導体:n−ドーパント試薬比が、99:1〜50:50の範囲である、項目1から12のいずれかに記載の方法。
[項目14]
有機電子バイスのn−ドープされた層を形成する方法であって、前記n−ドープされた層が項目1から13のいずれかに記載の方法に従って形成される、方法。
[項目15]
前記有機電子デバイスが、アノード、カソード、ならび前記アノードと前記カソードとの間の発光層を含む有機発光デバイスであり、前記n−ドープされた層が、前記発光層と前記カソードとの間の電子注入層である、項目14に記載の方法。
[項目16]
前記発光層が、溶液堆積方法によって形成される、項目15に記載の方法。
[項目17]
前記電子注入層が、前記発光層と接触する、項目15または16に記載の方法。
[項目18]
前記フィルムが、前記デバイスのアノードまたはカソードを通して照射される、項目15から17のいずれかに記載の方法。
[項目19]
前記フィルムが、前記デバイスの封入後に照射される、項目15から18のいずれかに記載の方法。
[項目20]
(a)C=N基、ニトリル基、C=O基およびC=S基の1つ以上を含む単位を含む有機半導体および(b)2,3−ジヒドロ−ベンゾイミダゾール基を含むn−ドーパント試薬を含む組成物。
[項目21]
前記n−ドーパント試薬が、2,3−ジヒドロ−1H−ベンゾイミダゾール基を含む、項目20に記載の組成物。
[項目22]
前記n−ドーパント試薬が、式(I)の化合物である、項目20または21に記載の組成物:
各R 2 は、独立に、C 1−20 ヒドロカルビル基であり;
R 3 はHまたはC 1−20 ヒドロカルビル基であり;
各R 4 が独立にC 1−20 ヒドロカルビル基である。
[項目23]
前記有機半導体がポリマーである、項目20から22のいずれかに記載の組成物。
[項目24]
前記有機半導体がベンゾチアジアゾール基を含む、項目20から23に記載の組成物。
[項目25]
前記n−ドーパント試薬が(4−(1,3−ジメチル−2,3−ジヒドロ−1H−ベンゾイミダゾール−2−イル)フェニル)ジメチルアミンである、項目20から24のいずれかに記載の組成物。
[項目26]
項目20から25のいずれかに記載の組成物からn−ドープされた半導体層を形成する方法であって、前記方法が前記有機半導体を励起する工程を含む、方法。
[項目27]
前記有機半導体が、熱処理または電磁照射によって励起される、項目27に記載の方法。
[項目28]
前記n−ドーパント試薬が(4−(1,3−ジメチル−2,3−ジヒドロ−1H−ベンゾイミダゾール−2−イル)フェニル)ジメチルアミンである、項目26または27に記載の方法。
101 基材
103 アノード
105 発光層
107 電子注入層
109 カソード
Claims (12)
- アノード、カソード、前記アノードと前記カソードとの間の発光層、および前記発光層と前記カソードとの間の電子注入層を含む有機発光デバイスであって、前記電子注入層は、
(a)C=N基、ニトリル基、C=O基およびC=S基の1つ以上を含む単位を含む有機ポリマー半導体および(b)2,3−ジヒドロ−ベンゾイミダゾール基を含むn−ドーパント試薬を含む組成物から形成されるn−ドープされた半導体を含み、
前記カソードは前記電子注入層と接触する、金属を含む層を含み、
前記ポリマーにカチオンは共有結合していない、
前記有機発光デバイス。 - 前記n−ドーパント試薬が、2,3−ジヒドロ−1H−ベンゾイミダゾール基を含む、請求項1に記載の有機発光デバイス。
- 前記有機半導体がベンゾチアジアゾール基を含む、請求項1から3のいずれかに記載の有機発光デバイス。
- 前記n−ドーパント試薬が(4−(1,3−ジメチル−2,3−ジヒドロ−1H−ベンゾイミダゾール−2−イル)フェニル)ジメチルアミンである、請求項1から4のいずれかに記載の有機発光デバイス。
- 前記金属は少なくとも4eVの仕事関数を有する、請求項1から5のいずれかに記載の有機発光デバイス。
- 前記電子注入層と接触する前記カソード層は金属からなる、請求項1から6のいずれかに記載の有機発光デバイス。
- 前記電子注入層は前記発光層と接触している、請求項1から7のいずれかに記載の有機発光デバイス。
- 請求項1から8のいずれかに記載の有機発光デバイスを形成する方法であって、前記方法がn−ドープされた半導体を形成するために前記有機半導体を励起する工程を含む、方法。
- 前記有機半導体が、熱処理または電磁照射によって励起される、請求項9に記載の方法。
- 前記n−ドーパント試薬が(4−(1,3−ジメチル−2,3−ジヒドロ−1H−ベンゾイミダゾール−2−イル)フェニル)ジメチルアミンである、請求項9または10に記載の方法。
- 前記有機半導体およびn−ドーパント試薬を含む組成物が前記発光層の上に堆積され、カソードが前記組成物の上に堆積される、請求項9から11のいずれかに記載の方法。
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