JP5909314B2 - 可溶性共役ポリマーを使用する方法及びデバイス - Google Patents
可溶性共役ポリマーを使用する方法及びデバイス Download PDFInfo
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- JP5909314B2 JP5909314B2 JP2007530486A JP2007530486A JP5909314B2 JP 5909314 B2 JP5909314 B2 JP 5909314B2 JP 2007530486 A JP2007530486 A JP 2007530486A JP 2007530486 A JP2007530486 A JP 2007530486A JP 5909314 B2 JP5909314 B2 JP 5909314B2
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- conjugated polymer
- polymer
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- light
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Images
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Description
本件特許出願は、2004年9月3日に出願された米国仮特許出願第60/607,335号及び2005年3月1日に出願された米国仮特許出願第60/657,836号の利益を主張する。
本発明を説明する際に、下記の用語を使用し、下記に示すように定義されるべきことを意図する。
「アルキル」は、1個又は2個以上の位置で任意に置換された1〜24個の炭素原子の、枝分かれした、枝分かれしていない又は環式の飽和炭化水素基を指し、多環式化合物を含む。アルキル基の例には、任意に置換された、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、s−ブチル、t−ブチル、n−ペンチル、イソペンチル、ネオペンチル、n−ヘキシル、n−ヘプチル、n−オクチル、n−デシル、ヘキシルオクチル、テトラデシル、ヘキサデシル、エイコシル、テトラコシルなど並びにシクロアルキル基、例えば、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、アダマンチル及びノルボルニルが含まれる。用語「低級アルキル」は、1〜6個の炭素原子、好ましくは1〜4個の炭素原子のアルキル基を指す。置換されたアルキル基上の代表的な置換基には、ヒドロキシル、シアノ、アルコキシ、=O、=S、−NO2、ハロゲン、ハロアルキル、ヘテロアルキル、カルボキシアルキル、アミン、アミド、チオエーテル及び−SHが含まれる。
「任意の」又は「任意に」は、続いて記載する事象又は状況が起きてもよく又は起きなくてもよいこと並びにこの記載に、該事象又は状況が単独で又は複数で起きている例及びこれが全く起きていない例が含まれることを意味する。例えば、句「任意に置換されたアルキル」は、置換されていてよい又は置換されていなくてよいアルキル単位を意味し、この記載には、置換されていないアルキル、単置換されたアルキル及び多置換されたアルキルの全てが含まれる。
極性媒体中に可溶性である共役ポリマー(CP)が提供され、本明細書に記載された実施形態に於いて使用することができる。CPには、極性媒体中のポリマー溶解度を増加させるための、ポリマーサブユニットに結合された可溶化官能基としての極性基が含まれている。CPのサブユニットの何れか又は全てに、1個又は2個以上の側鎖可溶化基が含まれていてよい。代表的な極性基には、1個又は2個以上の双極子モーメントをCPに導入するもの、例えば、ハロゲン化物、ヒドロキシル、アミン、アミド、シアノ、カルボン酸、スルホン酸及びチオールが含まれる。
可溶性共役ポリマーを溶解させるために使用される媒体は、極性であり、少なくとも1種の極性溶媒を含む。「極性」によって、正味双極子モーメントを有することが意味される。代表的な極性溶媒には、ジメチルスルホキシド、ジメチルホルムアミド、ギ酸、酢酸、酢酸エチル、水、アルコール及びポリアルコール、特に低級アルコール(C1-4)、特にメタノールが含まれる。好ましくは、極性溶媒は、少なくともエタノール又は酢酸エチルのものの極性を有する。幾つかの実施形態に於いて、CPを溶解させるために使用される極性溶媒は、その上にCPを堆積すべき第二の共役ポリマーを溶解させるためのその無能力性に基づいて選択される。
本明細書に記載されたCPは、種々の方法に於いて使用することができる。特に関心のある方法には、電子デバイス、特に共役ポリマーの多層を含むデバイスの中への、CPの堆積が含まれる。限定無しに、真空スパッタリング(RF又はマグネトロン)、電子ビーム蒸発、熱蒸着、化学蒸着、昇華及び溶液処理方法を含む、種々の堆積方法の何れも、所定のデバイスに於いて使用することができる。本発明に於いて提供された可溶性極性ポリマーを堆積するために、当該技術分野に於いて知られている又は見出すことができる何れの堆積方法も使用することができるけれども、溶液方法が現在好ましい。
CPは、オプトエレクトロニクス又はエレクトロニクスデバイス、バイオセンサー、フォトダイオード及び発光ダイオード(LED)を含むダイオード、オプトエレクトロニクス半導体チップ、半導体薄膜及びチップを含む種々の製造物品の何れの中にも含有させることができ、アレイ又はミクロアレイ形で使用することができる。このポリマーは、ポリマー性フォトスイッチの中に含有させることができる。このポリマーは、光信号を電気インパルスに転換させるための光インターコネクト又はトランスデューサーの中に含有させることができる。CPは、液晶材料として機能することができる。CPは、電気化学電池の電極として、エレクトロクロミック・ディスプレイ中の導電層として、電界効果トランジスターとして及びショットキーダイオードとして使用することができる。
下記の実施例は、本発明の製造方法及び使用方法の完全な説明を当業者に提供するように記載され、そして発明として見なされるものの範囲を限定することを意図しない。使用した数字(例えば、量、温度など)に関して正確性を確保する努力を払ったが、幾らかの実験誤差及び偏差が考えられるべきである。他の方法で示さない限り、部は重量部であり、温度は摂氏度であり、圧力は大気圧又はその付近であり、全ての材料は市販されている。
一つの実施形態に於いて、ポリマー発光ダイオード(PLED)を、デバイス形状:ITO/PEDOT/発光性ポリマー/ETL/Ba/Alで、発光層として有機溶媒中の溶液から流延した半導性ポリマー及び電子輸送層(ETL)として水溶性(又はメタノール溶解性)共役コポリマーを使用して製作した。この結果は、ETLを有するデバイスが、著しく低いターンオン電圧、より高い明るさ及び改良された発光効率を有することを示している。図参照。
図2は、ETL有り及び無しで、PFOを使用して製造されたデバイスの、電流密度対電圧及び明るさ対電圧特性を示す。PFO/ETLデバイスは、約3Vでターンオンし(ターンオン電圧は、0.1cd/m2の明るさでの電圧として定義される)、一方、ETL無しで製造されたPFOデバイスについて、ターンオン電圧は約5Vである[18]。6Vで、PFO/ETLデバイスから得られた輝度(luminance)(L)は、ETL無しのデバイスについてのL=30cd/m2に比較して、L=3450cd/m2である。
HTL/HIL層、ETL/EIL層又は両方を含む、種々の形状にある多層PLEDを、下記のようにして製造し、そしてキャラクタリゼーションした。
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Claims (23)
- 半導性共役ポリマーを含有する発光層、並びに
電子を発光層に注入及び/又は輸送するように配置されており、発光半導性ポリマーのπ*−バンドに近い又はその中のエネルギーで、最低空分子軌道(LUMO)を有する共役ポリマーを含有する電子注入/輸送層、並びに
正孔を発光層に注入及び/又は輸送するように配置されており、発光半導性ポリマーの価電子帯に近い又はその中のエネルギーで、最高被占分子軌道(HOMO)を有する共役ポリマーを含有する正孔注入/輸送層、
を含む多層発光デバイス(LED)であって、
電子注入/輸送層、正孔注入/輸送層及び発光層が、溶液処理技術によるそれらの段階的堆積を可能にする溶解度を有し、電子注入/輸送層が、ジメチルスルホキシド、ジメチルホルムアミド、蟻酸、酢酸、酢酸エチル、水、アルコール及びポリアルコールからなる群より選択される少なくとも1種の極性溶媒中に可溶性であり、電子注入/輸送層に含まれる共役ポリマーが、前記共役ポリマーに結合しており前記極性媒体中の前記共役ポリマーの溶解度を増加させるための側鎖可溶化基を有しており、そして発光層がハロ炭化水素及び芳香族炭化水素からなる群より選択される少なくとも1種の有機溶媒中に可溶性である、多層発光デバイス。 - 発光層が緑色光を発光する、請求項1記載のLED。
- 発光層が、ポリ[2−メトキシ−5−(2−エチル−ヘキシルオキシ)−1,4−フェニレンビニレン](「MEH−PPV」)を含有する、請求項2記載のLED。
- 発光層が赤色光を発光する、請求項1記載のLED。
- 発光層が、(9,9−ジヘキシル−フルオレン)−(ベンゾチアジアゾール)共重合体(「PFO−BT」)を含有する、請求項4記載のLED。
- 発光層が青色光を発光する、請求項1記載のLED。
- 発光層が、ポリ(9,9−ジオクチルフルオレニル−2,7−ジイル)(「PFO」)を含有する、請求項6記載のLED。
- 複数個の請求項1記載のLEDを含有するマトリックス。
- 請求項1記載のLEDを含有するディスプレイデバイス。
- ディスプレイデバイスがフルカラーディスプレイである、請求項9記載のディスプレイデバイス。
- 基体上の共役ポリマーの隣接層の形成方法であって、
ジメチルスルホキシド、ジメチルホルムアミド、蟻酸、酢酸、酢酸エチル、水、アルコール及びポリアルコールからなる群より選択される少なくとも1種の極性溶媒及び前記極性媒体中の前記共役ポリマーの溶解度を増加させるための側鎖可溶化基が結合している第一共役ポリマーを含有する第一溶液を用意する工程、
第二共役ポリマー及び第二溶媒を含有する第二溶液を用意する工程、
前記第二溶液の第一層である発光層を基体の上に堆積し、そして第一層から溶媒を除去する工程、及び
前記第一溶液の第二層である電子注入/輸送層を第一層の上に堆積し、そして第二層から溶媒を除去する工程を含み、
第一層内で堆積されたポリマーが、第二層内で堆積された溶媒中に溶解せず、そして、第一共役ポリマーが、第二共役ポリマーのπ*−バンドに近い又はその中のエネルギーで、最低空分子軌道(LUMO)を有する方法。 - 極性溶媒が水を含む、請求項11記載の方法。
- 極性溶媒がメタノールを含む、請求項11記載の方法。
- 第一溶液を堆積することに、第一溶液を第一層の上に印刷することが含まれる、請求項11記載の方法。
- 第一層の上に第一溶液を堆積することに、スピン流延が含まれる、請求項11記載の方法。
- 第一層の上に第一溶液を堆積することに、ドロップ流延が含まれる、請求項11記載の方法。
- 前記溶媒を除去する工程の少なくとも1個に加熱することが含まれる、請求項11記載の方法。
- 前記溶媒を除去する工程の少なくとも1個に、雰囲気圧力を低下させることが含まれる、請求項11記載の方法。
- 前記溶媒を除去する工程の少なくとも1個に蒸発させることが含まれる、請求項11記載の方法。
- 基体に電極が含まれる、請求項11記載の方法。
- 基体がフィルムである、請求項11記載の方法。
- 更に、1個又は2個以上の前記第一層の上への、別個の分離した第二層の複数回の堆積を含む、請求項11記載の方法。
- 半導性共役ポリマーを含有する発光層、並びに
電子を発光層に注入及び/又は輸送するように配置されており、発光半導性ポリマーのπ*−バンドに近い又はその中のエネルギーで、最低空分子軌道(LUMO)を有する共役ポリマーを含有する電子注入/輸送層を含む多層発光デバイス(LED)であって、
電子注入/輸送層が、ジメチルスルホキシド、ジメチルホルムアミド、蟻酸、酢酸、酢酸エチル、水、アルコール及びポリアルコールからなる群より選択される少なくとも1種の極性溶媒中に可溶性であり、電子注入/輸送層に含まれる共役ポリマーが、前記共役ポリマーに結合しており前記極性媒体中の前記共役ポリマーの溶解度を増加させるための側鎖可溶化基を有しており、そして発光層がハロ炭化水素及び芳香族炭化水素からなる群より選択される少なくとも1種の有機溶媒中に可溶性である多層発光デバイス。
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US60/657,836 | 2005-03-01 | ||
PCT/US2005/031911 WO2006029226A1 (en) | 2004-09-03 | 2005-09-06 | Methods and devices utilizing soluble conjugated polymers |
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US8795781B2 (en) | 2014-08-05 |
US20060054886A1 (en) | 2006-03-16 |
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