JP5494390B2 - 透明導電膜、および有機エレクトロルミネッセンス素子 - Google Patents
透明導電膜、および有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP5494390B2 JP5494390B2 JP2010213255A JP2010213255A JP5494390B2 JP 5494390 B2 JP5494390 B2 JP 5494390B2 JP 2010213255 A JP2010213255 A JP 2010213255A JP 2010213255 A JP2010213255 A JP 2010213255A JP 5494390 B2 JP5494390 B2 JP 5494390B2
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- Manufacturing Of Electric Cables (AREA)
Description
〈バインダー樹脂〉
本発明のバインダー樹脂は、バインダー骨格中にオキサゾリン基を含有していれば特に限定はない、オキサゾリン基を含有する構造単位以外に他の構造単位を含有していてもよい。
本発明では、第2導電層は導電性ポリマーを含有する。
本発明に用いるπ共役系導電性高分子としては、特に限定されず、ポリチオフェン(基本のポリチオフェンを含む、以下同様)類、ポリピロール類、ポリインドール類、ポリカルバゾール類、ポリアニリン類、ポリアセチレン類、ポリフラン類、ポリパラフェニレンビニレン類、ポリアズレン類、ポリパラフェニレン類、ポリパラフェニレンサルファイド類、ポリイソチアナフテン類、ポリチアジル類、の鎖状導電性ポリマーを利用することができる。中でも、導電性、透明性、安定性等の観点からポリチオフェン類やポリアニリン類が好ましい。ポリエチレンジオキシチオフェンが最も好ましい。
π共役系導電性高分子の形成に用いられる前駆体モノマーは、分子内にπ共役系を有し、適切な酸化剤の作用によって高分子化した際にもその主鎖にπ共役系が形成されるものである。例えば、ピロール類及びその誘導体、チオフェン類及びその誘導体、アニリン類及びその誘導体等が挙げられる。
本発明に用いられるポリ陰イオンは、置換もしくは未置換のポリアルキレン、置換もしくは未置換のポリアルケニレン、置換もしくは未置換のポリイミド、置換もしくは未置換のポリアミド、置換もしくは未置換のポリエステル及びこれらの共重合体であって、アニオン基を有する構成単位とアニオン基を有さない構成単位とからなるものである。
本発明に係る第1導電層は、フィルム基板上に金属材料をパターン状に形成することを特徴とする。これにより金属材料からなる光不透過の導電部と透光性窓部を併せ持つフィルム基板となり、透明性、導電性に優れた電極基板が作製できる。金属材料は、導電性に優れていれば特に制限はなく、例えば、金、銀、銅、鉄、ニッケル、クロム等の金属の他に合金でもよい。特に、後述のようにパターンの形成のしやすさの観点から金属材料の形状は、金属微粒子または金属ナノワイヤであることが好ましく、金属材料は導電性の観点から銀であることが好ましい。
本発明の透明電極に用いられる基材はフィルム基板とも呼ばれ、高い光透明性を有し、フレキシブル性に優れており、誘電損失係数が十分小さくて、マイクロ波の吸収が加熱対象である導電層よりも小さい材質であれば特に制限はない。例えば、樹脂基板、樹脂フィルム等が好適に挙げられるが、生産性の観点や軽量性と柔軟性といった性能の観点から透明樹脂フィルムを用いることが好ましい。
本発明の有機エレクトロルミネッセンス素子は、本発明の透明電極を有することを特徴とする。
合成例1(P−1の合成:本発明)
P−1はPolymer Journal,Vol.3,No.3,307−314(1972)に記載の方法に準じて下記のように合成した。
装置:Wagers2695(Separations Module)
検出器:Waters 2414(Refractive Index Detector)
カラム:Shodex Asahipak GF−7M HQ
溶離液:ジメチルホルムアミド(20mM LiBr)
流速:1.0ml/min
温度:40℃
合成例2(P−2の合成:本発明)
モノマーとしてOM−2、0.89g(8mmol、分子量:111.07)、M−1、0.93g(8mmol、分子量:116.05)、N−アクリロイルモルホリン0.56g(4mmol、分子量:141.08)を用いた以外は合成例1と同様な方法により、数平均分子量8900、分子量分布2.7、の水溶性バインダー樹脂P−2を1.79g(収率75%)得た。
モノマーとしてOM−16、1.74g(8mmol、分子量:217.07)、メチルアクリレート0.17g(2mmol、分子量:86.04)、N,N−ジメチルアクリルアミド0.99g(10mmol、分子量:99.07)を用いた以外は合成例1と同様な方法により、数平均分子量9100、分子量分布2.6、の水溶性バインダー樹脂P−3を2.25g(収率78%)得た。
モノマーとしてOM−2、0.67g(6mmol、分子量:111.07)、M−1、1.62g(14mmol、分子量:116.05)を用いた以外は合成例1と同様な方法により、数平均分子量11100、分子量分布2.3、の水溶性バインダー樹脂P−4を1.62g(収率71%)得た。
モノマーとしてOM−2、0.89g(8mmol、分子量:111.07)、M−1、1.39g(12mmol、分子量:116.05)を用いた以外は合成例1と同様な方法により、数平均分子量8400、分子量分布2.8、の水溶性バインダー樹脂P−5を1.82g(収率80%)得た。
モノマーとしてOM−2、1.11g(10mmol、分子量:111.07)、M−1、1.16g(10mmol、分子量:116.05)を用いた以外は合成例1と同様な方法により、数平均分子量7900、分子量分布3.1、の水溶性バインダー樹脂P−6を1.66g(収率73%)得た。
モノマーとしてOM−2、1.33g(12mmol、分子量:111.07)、M−1、0.93g(8mmol、分子量:116.05)を用いた以外は合成例1と同様な方法により、数平均分子量9100、分子量分布2.6、の水溶性バインダー樹脂P−7を1.74g(収率77%)得た。
モノマーとしてOM−2、1.55g(14mmol、分子量:111.07)、M−1 0.70g(6mmol、分子量:116.05)を用いた以外は合成例1と同様な方法により、数平均分子量9600、分子量分布2.7、の水溶性バインダー樹脂P−8を1.62g(収率72%)得た。
モノマーとしてOM−5、1.11g(10mmol、分子量:111.07)、M−11、1.16g(10mmol、分子量:116.05)を用いた以外は合成例1と同様な方法により、数平均分子量8200、分子量分布2.4、の水溶性バインダー樹脂P−9を1.72g(収率76%)得た。
モノマーとしてOM−10、1.25g(10mmol、分子量:125.08)、M−1、1.15g(10mmol、分子量:115.06)を用いた以外は合成例1と同様な方法により、数平均分子量9100、分子量分布2.6、の水溶性バインダー樹脂P−10を1.92g(収率80%)得た。
モノマーとしてアクリル酸の代わりにM−11、1.15g(10mmol、分子量:115.06)を用いた以外は合成例1と同様な方法により、数平均分子量11200、分子量分布2.9、の水溶性バインダー樹脂P−8を1.79g(収率79%)得た。
200ml三ツ口フラスコにTHF100mlを加え10分間加熱還流させた後、窒素下で室温に冷却した。2−ヒドロキシエチルアクリレート3.0g(26mmol、分子量:115.06)、AIBN、0.43g(2.6mmol、分子量:164.11)を加え、5時間加熱還流した。室温に冷却した後、不溶部を直径40mmの桐山ロート(No.5C濾紙使用)で濾過し、40℃1時間減圧乾燥した。得られた不溶物を水10mlに溶解し、激しく撹拌した100mlヘプタン中へ投入した。1時間後、不溶部を直径60mmの桐山ロート(No.5C濾紙使用)で濾過し、40℃1時間減圧乾燥した。その結果、数平均分子量25200、分子量分布2.8の水溶性バインダー樹脂P−12を2.81g(収率94%)得た。
厚み100μmのポリエチレンテレフタレートフィルム(コスモシャインA4100、東洋紡績株式会社製)の下引き加工していない面に、JSR株式会社製UV硬化型有機/無機ハイブリッドハードコート材:OPSTAR Z7501を塗布、乾燥後の平均膜厚が4μmになるようにワイヤーバーで塗布した後、80℃、3分で乾燥後、空気雰囲気下、高圧水銀ランプ使用して硬化条件1.0J/cm2で硬化を行い、平滑層を形成した。
パーヒドロポリシラザン(PHPS、AZエレクトロニックマテリアルズ(株)製アクアミカ NN320)の20質量%ジブチルエーテル溶液をワイヤレスバーにて、乾燥後の(平均)膜厚が、0.30μmとなるように塗布し、塗布試料を得た。
得られた塗布試料を温度85℃、湿度55%RHの雰囲気下で1分処理し、乾燥試料を得た。
乾燥試料をさらに温度25℃、湿度10%RH(露点温度−8℃)の雰囲気下に10分間保持し、除湿処理を行った。
除湿処理を行った試料を下記の条件で改質処理を行い、ガスバリア層を形成した。改質処理時の露点温度は−8℃で実施した。
株式会社エム・ディ・コム製エキシマ照射装置MODEL:MECL−M−1−200、波長172nm、ランプ封入ガス Xe
稼動ステージ上に固定した試料を以下の条件で改質処理を行った。
エキシマ光強度 60mW/cm2(172nm)
試料と光源の距離 1mm
ステージ加熱温度 70℃
照射装置内の酸素濃度 1%
エキシマ照射時間 3秒
上記のようにしてガスバリア性を有する透明電極用のフィルム基板を作製した。
上記で得られたガスバリア性を有する透明電極用フィルム基板上のバリアのない面に、以下の方法で第1導電層を形成した。
細線格子(金属材料)については以下に示す、グラビア印刷または銀ナノワイヤにより作製した。
銀ナノ粒子ペースト1(M−Dot SLP:三ツ星ベルト製)をRK Print Coat Instruments Ltd製グラビア印刷試験機K303MULTICOATERを用いて線幅50μm、高さ1.5μm、間隔1.0mmの細線格子を印刷した後、110℃、5分の乾燥処理を行った。
ランダムな網目構造については以下に示すように銀ナノワイヤを用いて作製した。
《透明電極の作製》
〈透明電極TC−101の作製〉
ガスバリア性を有する透明電極用のフィルム基板上にグラビア印刷にて第1導電層を形成した透明電極上に、下記塗布液Aを、押し出し法を用いて、乾燥膜厚300nmになるように押し出しヘッドのスリット間隙を調整して塗布し、110℃、5分で加熱乾燥し、導電性ポリマーと水溶性バインダー樹脂からなる第2導電層を形成し、得られた電極を8×8cmに切り出した。得られた電極を、オーブンを用いて110℃、30分加熱することで透明電極TC−101を作製した。
(塗布液A)
ポリチオフェン:PEDOT−PSS CLEVIOS PH510(固形分濃度1.89%、H.C.Starck社製) 1.59g
P−1(固形分20%水溶液) 0.35g
ジメチルスルホキシド(DMSO) 0.08g
(透明電極TC−102〜TC−111の作製)
透明電極1の作製において、塗布液AのP−1を、P−2〜P−11に変更したこと以外は透明電極TC−101の作製と同様にして、透明電極TC−102〜TC−111を作製した。
透明電極1の作製において、塗布液A中のP−1をP−6に変更し、更に塗布液AのPEDOT−PSS CLEVIOS PH510(固形分1.89%、H.C.Starck社製)を、ポリアニリンM(固形分濃度6.0%、ティーエーケミカル)0.5gに変更したこと以外は透明電極TC−101の作製と同様にして、透明電極TC−112を作製した。
(ランダムな網目構造)
銀ナノワイヤ分散液は、Adv.Mater.,2002,14,833〜837に記載の方法を参考に、PVP K30(分子量5万;ISP社製)を利用して、平均短径75nm、平均長さ35μmの銀ナノワイヤを作製し、限外濾過膜を用いて銀ナノワイヤを濾別、洗浄処理した後、ヒドロキシプロピルメチルセルロース60SH−50(信越化学工業社製)を銀に対し25質量%加えた水溶液に再分散し、銀ナノワイヤ分散液を調製した。
透明電極TC−101の作製において、塗布液A中のP−1をP−12に変更した以外し、第1導電層を形成したこと以外は透明電極TC−101の作製と同様にして、透明電極TC−114を作製した。
透明電極TC−101の作製において、第1導電層を形成しないで第2導電層を形成したこと以外は透明電極TC−101の作製と同様にして、透明電極TC−115を作製した。
得られた透明電極のフィルム形状、透明性、表面抵抗(導電性)及び膜強度を下記のように評価した。また、透明電極の安定性を評価するため、80℃90%RHの環境下で3日間置く強制劣化試験後の透明電極試料のフィルム形状、透明性、表面抵抗及び膜強度評価を行なった。
JIS K 7361−1:1997に準拠して、東京電色社製 HAZE METER NDH5000を用いて、全光線透過率を測定し、下記基準で評価した。有機電子デバイスに用いるため、75%以上であることが好ましい。
○:75%〜80%未満
△:70%〜75%未満
×:70%未満
(表面抵抗)
JIS K 7194:1994に準拠して、抵抗率計(ロレスタGP(MCP−T610型):(株)ダイヤインスツルメンツ社製)を用いて表面抵抗を測定した。表面抵抗は100Ω/□以下であることが好ましく、有機電子デバイスを大面積にするには、30Ω/□以下であることが好ましい。
導電層の膜の強度を、テープ剥離法により評価した。
○:3回の圧着剥離で変化無し
△:1回の圧着剥離で剥離が見られるが8割以上のパターンが残っている
×:1回の圧着剥離で剥離が見られ、残っているパターンが8割未満
評価の結果を表1に示す。
《有機ELデバイスの作製》
作製した透明電極基板を超純水で洗浄後、パターン辺長20mmの正方形タイル状透明パターン一個が中央に配置されるように30mm角に切り出し、アノード電極に用いて、以下の手順でそれぞれ有機ELデバイスを作製した。正孔輸送層以降は蒸着により形成した。透明電極TC−101〜TC−115を用い、それぞれ有機EL素子OEL−201〜OEL−215を作製した。
真空度1×10−4Paまで減圧した後、化合物1の入った前記蒸着用るつぼに通電して加熱し、蒸着速度0.1nm/秒で蒸着し、厚さ30nmの正孔輸送層を設けた。
次に、以下の手順で各発光層を設けた。
さらに、形成した有機発光層と同じ領域に、化合物6を膜厚5nmに蒸着して正孔阻止層を形成した。
引き続き、形成した正孔阻止層と同じ領域に、CsFを膜厚比で10%になるように化合物6と共蒸着し、厚さ45nmの電子輸送層を形成した。
形成した電子輸送層の上に、透明電極を陽極として陽極外部取り出し端子及び15mm×15mmの陰極形成用材料としてAlを5×10−4Paの真空下にてマスク蒸着し、厚さ100nmの陽極を形成した。
得られた有機EL素子について発光ムラ及び寿命を下記のように評価した。
発光均一性は、KEITHLEY製ソースメジャーユニット2400型を用いて、直流電圧を有機EL素子に印加し発光させた。1000cd/m2で発光させた有機EL素子OEL−201〜OEL−215について、50倍の顕微鏡で各々の発光輝度ムラを観察した。また、有機EL素子OEL−201〜OEL−215をオーブンにて60%RH、80℃2時間加熱したのち、再び前記23±3℃、55±3%RHの環境下で1時間以上調湿した後、同様に発光均一性を観察した。
○:ほとんど均一発光しており、問題ない
△:部分的に若干発光ムラが見られるが、許容できる
×:全面にわたって発光ムラが見られ、許容できない
(寿命)
得られた有機EL素子の、初期の輝度を5000cd/m2で連続発光させて、電圧を固定して、輝度が半減するまでの時間を求めた。アノード電極をITOとした有機EL素子を上記と同様の方法で作製し、これに対する比率を求め、以下の基準で評価した。100%以上が好ましく、150%以上であることがより好ましい。
○:100〜150%未満
△:80〜100%未満
×:80%未満
評価の結果を表2に示す。
2 本発明のバインダー樹脂と導電性ポリマーを含有する第2導電層
3 基材
Claims (4)
- 基材上にパターン上に形成された金属材料からなる第1導電層と、導電性ポリマーを含有する第2導電層を有する透明導電膜において、前記第2導電層にオキサゾリン基を有する構造単位を含むバインダー樹脂を含有させることを特徴とする透明導電膜。
- 前記第2導電層に含有させるバインダー樹脂がヒドロキシ基を有する構造単位とオキサゾリン基を有する構造単位を含むことを特徴とする請求項1に記載の透明導電膜。
- 前記バインダー樹脂中のオキサゾリン基を有する構造単位のモル比が40〜60%であることを特徴とする請求項1または2に記載の透明導電膜。
- 請求項1〜3のいずれか1項に記載の透明導電膜を用いたことを特徴とする有機エレクトロルミネッセンス素子。
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WO2012014621A1 (ja) * | 2010-07-29 | 2012-02-02 | コニカミノルタホールディングス株式会社 | 透明導電膜、および有機エレクトロルミネッセンス素子 |
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