JP5599980B2 - 導電膜とその製造方法、並びに有機エレクトロルミネッセンス素子 - Google Patents
導電膜とその製造方法、並びに有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP5599980B2 JP5599980B2 JP2009057237A JP2009057237A JP5599980B2 JP 5599980 B2 JP5599980 B2 JP 5599980B2 JP 2009057237 A JP2009057237 A JP 2009057237A JP 2009057237 A JP2009057237 A JP 2009057237A JP 5599980 B2 JP5599980 B2 JP 5599980B2
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- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical group CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- FGKCGMMQJOWMFW-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;bromide Chemical compound [Br-].CC(=C)C(=O)OCC[N+](C)(C)C FGKCGMMQJOWMFW-UHFFFAOYSA-M 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
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Description
一般式(II) R 5 COO −
〔式中、R 5 は置換基を示す。〕
2.前記一般式(I)で表される化合物のX1、X2、X3及びX4が硫黄原子であることを特徴とする前記1記載の導電膜。
前記一般式(I)で表される化合物を含有する溶液と、前記一般式(I)で表される化合物の酸化体の塩を含有する溶液と、前記バインダーを含有する溶液とを混合後、支持体上へ塗布、乾燥する工程で製造することを特徴とする導電膜の製造方法。
5.前記一般式(I)で表される化合物のX 1 、X 2 、X 3 及びX 4 が硫黄原子であることを特徴とする前記4記載の導電膜の製造方法。
6.前記一般式(I)で表される化合物の酸化体の塩のカウンターアニオンが下記一般式(II)表されるアニオンであることを特徴とする前記4又は5記載の導電膜の製造方法。
一般式(II) R 5 COO −
〔式中、R 5 は置換基を示す。〕
本発明に係る導電性ナノワイヤーとは、導電性を有し、かつその長さが直径(太さ)に比べて十分に長い形状を持つものである。本発明に係る導電性ナノワイヤーは、透明導電層内において導電性ナノワイヤーが互いに接触し合うことにより3次元的な導電ネットワークを形成し補助電極として機能すると考えられる。従って、導電性ナノワイヤーが長い方が導電ネットワーク形成に有利であるため好ましい。一方で、導電性ナノワイヤーが長くなると導電性ナノワイヤーが絡み合って凝集体を生じ、光学特性を劣化させる場合がある。導電ネットワーク形成や凝集体生成には、導電性ナノワイヤーの剛性や直径等も影響するため、使用する導電性ナノワイヤーに応じて最適な平均アスペクト比(アスペクト=長さ/直径)のものを使用することが好ましい。大凡の目安として、平均アスペクト比は、10〜10,000であるものが好ましく、より好ましくはで15〜1,000である。
本発明のナノワイヤーの形状としては中空チューブ状、ワイヤー状、ファイバー状、ロッド状等がある。本発明の導電性ナノワイヤーは、有機物成分のみで構成されているが、該有機導電性ナノワイヤーと無機ナノワイヤー、導電性金属酸化物ナノワイヤー、金属ナノワイヤー、炭素繊維、カーボンナノチューブ等と併用して用いても良い。また、本発明の導電性ナノワイヤーを金属や金属酸化物等でコーティングして用いても良い。コスト(原材料費、製造費)と性能(導電性、透明性、可撓性)の観点から、有機導電性ナノワイヤーである一般式(I)と該一般式(I)で表わされる化合物の酸化体の塩からなる混合原子価化合物で構成される導電性ナノワイヤーが最も好ましい。
本発明に係るバインダーとしては透明ならば何を用いてもかまわない。水溶性高分子、有機溶剤溶解性高分子、ポリマーラテックス、水性アイオノマーや熱硬化性樹脂、光硬化樹脂、エネルギー線硬化樹脂等の組成物等の中から任意に選択すればよい。また、重合性モノマーやオリゴマーあるいはそれらの混合物を塗布した後、光や熱や電子線などで重合して透明バインダー層を形成しても良い。これらのうち、透明バインダー層として高分子バインダーを用いる場合、高分子バインダーとなるものの例としては、PolymerHandbookVI/453−VI/461に列挙されているものを好適に用いることができる。
本発明の導電膜は、本発明の導電性ナノワイヤーとバインダーからなる自立膜でもよく、また支持体に該導電膜を積層しても良い。
本発明の支持体として、本発明の導電ナノワイヤーとバインダーからなる導電膜が積層できれば特に制限はないが、ガラス、樹脂フィルムが好ましく、光学用途に用いる場合、無色で透明である透明基材であることが好ましい。
本発明の導電膜の製造方法において、一般式(I)で表される化合物を含有する溶液(A)、一般式(I)で表される化合物の酸化体の塩を含有する溶液(B)及びバインダーを含有する溶液(C)を混合後、支持体上へ塗布し、その後乾燥を行ない製造される。一般式(I)で表される化合物を含有する溶液(A)の溶媒は一般式(I)で表される化合物が溶解すれば特に制限はないが、アセトニトリルが好ましい。溶液(A)の濃度は、一般式(I)で表される化合物が析出しない濃度が良く、1〜20mMが好ましく、特に好ましくは3〜10mMである。一般式(I)で表される化合物の酸化体の塩は、一般式(I)で表される化合物と酸化剤を溶解した溶液中で製造される。酸化剤には特に制限はないが、フェリシアン化カリウム(K3Fe(CN)6)、ヨードベンゼンジアセテートが好ましく、特に好ましくはヨードベンゼンジアセテートである。一般式(I)で表される化合物の酸化体の塩を製造するときの用いる溶媒には、特に制限はないが、アセトニトリルが好ましい。一般式(I)で表される化合物の酸化体の塩を含有する溶液(B)の溶媒は一般式(I)で表される化合物の酸化体の塩が溶解すれば特に制限はないが、アセトニトリルが好ましい。溶液(B)の濃度は、一般式(I)で表される酸化体の塩が析出しない濃度が良く、1〜50mMが好ましく、特に好ましくは5〜30mMである。バインダーを含有する溶液(C)の溶媒は、使用するバインダーが溶解すれば特に制限はなく、例えばポリメチルメタクリレート、ポリビニルピロリドン及びポリスチレンの場合は、それぞれ塩化メチレン、アセトニトリル及びベンゼンが好ましい。塗布溶液の調製は、一般式(I)で表される化合物を含有する溶液(A)、一般式(I)で表される化合物の酸化体の塩を含有する溶液(B)及びバインダーを含有する溶液(C)を混合後、室温で攪拌することにより得られる。攪拌時間は、1〜180分が好ましく、より好ましくは3〜120分で、更に好ましくは5〜60分である。
本発明の導電膜はパターニングすることができる。パターニングの方法やプロセスには特に制限はなく、公知の手法を適宜適用することができる。例えば、離型面上にパターニングされた導電膜を形成した後、透明基材上に転写することによってパターニングされた導電膜を形成する方法を用いることができ、具体的には、以下のような方法を好ましく用いることができる。
ii)離型性基板上に本発明の導電膜を一様に形成した後、一般的なフォトリソプロセスを用いてパターニングする方法
iii)例えば紫外線硬化型樹脂を含む導電性材料を使用して本発明の導電膜を一様に形成した後、フォトリソプロセス様にパターニングする方法
iv)離型性基板上に予めフォトレジストで形成したネガパターン上に本発明の導電膜を一様に形成し、リフトオフ法を用いてパターニングする方法
上記のいずれの方法においても、離型性基板上でパターニングした導電膜層を透明基材上に転写することにより、パターニングされた本発明の導電膜を形成することができる。
本発明の導電膜は高い導電性と透明性を併せ持ち、液晶表示素子、有機発光素子、無機電界発光素子、電子ペーパー、有機太陽電池、無機太陽電池等の各種オプトエレクトロニクスデバイスや、電磁波シールド、タッチパネル等の分野において好適に用いることができる。その中でも、透明電極表面の平滑性が厳しく求められる有機エレクトロルミネッセンス素子の導電膜として特に好ましく用いることができる。
(一般式(I)で表される化合物の酸化体の塩合成)
100mlのナスフラスコにおいて、テトラチアフルバレン(以後TTFと省略する)(286mg,1.40mmol、東京化成社より購入)とヘプタフルオロ酪酸(363μL,2.80mmol、和光純薬社より購入)をiodebenzene−diacetate(225mg,0.70mmol、東京化成社より購入)存在下、15mlのアセトニトリル(和光純薬社より購入)溶液中に溶解させた。室温中で30分間の撹拌により溶液が褐色に変化した後、200mlのジエチルエーテル(和光純薬社より購入)を加え、対アニオンとしてヘプタブチル酪酸アニオンを有するTTFラジカルカチオン塩の沈殿を形成させた。該沈殿をろ過後、アセトニトリルにより洗浄することにより褐色沈殿として434mg(収率74%)を得た。化合物の物性データは元素分析、紫外可視吸収スペクトル測定と質量測定に行なった。
計算値(%):C,28.78;H,0.97;F,31.86;O,7.67;S,30.73
実験値(%):C,29.07;H,1.18;F,31.66.
UV/vis/NIR(CH3CN)
λmax(ε)=265(1200),339(4900),436(14600),578(4000).
HRMS(EI+)
計算値:C6H4S4(TTF+)として203.9196
測定値:203.9192.
(FAB)
計算値:C4F7O2(C3F7COO−),212.9792
測定値:212.9786.
比較例1
(比較導電膜1(PEDOT/PSS膜)の作製)
Aldrich社より購入したPEDOT/PSS水溶液をガラス基板上に滴下し、室温で16時間放置することで、乾燥膜厚2μmの比較導電膜1を作製した。
TTF(10mg、0.049mmol)と合成例1により得られたTTFの酸化体の塩 28.8mg、0.069mmol)を10mlのアセトニトリルに溶解した溶液をガラス基板上に滴下し、室温で16時間放置することで、乾燥膜厚4μmの比較導電膜2を作製した。比較導電膜2の透明度及び導電性を比較導電膜1の方法で測定した結果、透過率69%、導電性1.6×10−2S/cmであった。
(導電膜1−1〜1−6の作製)
スキーム1に導電性ナノワイヤーを含む導電膜の作製法の概略を示す。
得られた導電膜1及び比較導電膜1、2について、以下の評価を行った。
四端子法により導電膜上の異なる5点における導電率を算出し、平均値を算出した。表2に導電膜中のTTF種の濃度に対するそれぞれの平均の導電率を示す。括弧内は値の標準偏差を示す。得られた結果を表2に示す。
400nmから800nm間で紫外可視吸収スペクトル測定を行い、透過率を計測した。この波長間での平均透過率を1μm当たりに換算したものを透過率とした。得られた結果を表2に示す。
導電膜2−1〜2−6の作製
ポリメタクリル酸メチルをポリビニルピロリドン(PVP,Mw=10,000、Aldrich社より購入)に換えた以外は実施例1と同様に本発明の導電膜2−1〜2−6を作製した。
導電膜3−1〜3−6の作製
ポリメタクリル酸メチルをポリスチレン(Mw=100,000〜140,000、ナカライテスク社より購入)に換えた以外は実施例1と同様に本発明の導電膜3−1〜3−6を作製した。
導電膜を空気中、室温で放置し、時間経過による導電率の変化を調べ、図2に結果を示す。
a.実施例3の導電膜(PSバインダー)の導電率の時間変化、
b.実施例1の導電膜(PMMAバインダー)の導電率の時間変化、
c.実施例2の導電膜(PVPバインダー)の導電率の時間変化、
d.比較例2の導電膜(導電性ナノワイヤーのみ)の導電率の時間変化を示す図である。
導電膜の表面観察を走査型電子顕微鏡(JEOL JSM−5600)を用いて行なった。電圧1.5kVにより測定を行ない、図3に結果を示す。
a.導電膜3−6(TTF35mol%含有PS導電膜)の走査型顕微鏡写真、
b.導電膜1−3(TTF35mol%含有PMMA導電膜)の走査型顕微鏡写真、
c.導電膜2−3(TTF35mol%含有PVP導電膜)の走査型顕微鏡写真、
d.比較導電膜2(TTFのみからなる導電膜)の走査型顕微鏡写真である。
紫外可視近赤外吸収スペクトルにより35mol%導電性ナノワイヤー含有導電膜を観察し、図4にその結果を示す。
a.導電膜3−6(導電性ナノワイヤー35mol%含有PS導電膜)の紫外可視近赤外吸収スペクトルを示す
b.導電膜1−3(導電性ナノワイヤー35mol%含有PMMA導電膜)の紫外可視近赤外吸収スペクトルを示す
c.導電膜2−3(導電性ナノワイヤー35mol%含有PVP導電膜)の紫外可視近赤外吸収スペクトルを示す図である。
本発明の導電膜1〜3をガラス基板上よりはがした後、破砕することで粉末状の試料を作製した。得られたサンプル10mgを用い、粉末X線回析スペクトル(SHIMADZUX−ray diffractometer−6000)を測定した。CuKα線により、0.02度/Sで2度から90度まで測定を行った。図5にその結果を示す。
a.導電膜3の粉末X線回析スペクトル、
b.導電膜1の粉末X線回析スペクトル、
c.導電膜2の粉末X線回析スペクトルを示す。
[有機エレクトロルミネッセンス素子(有機EL素子)の作製]
実施例1〜3で作製した本発明の導電膜1−3、2−3、3−3及び1−6、2−6、3−6を第1電極(アノード電極)に用いて、以下の手順でそれぞれ有機EL素子OEL−101〜106を作製した。
上記本発明の各導電膜の上に、ポリ(3,4−エチレンジオキシチオフェン)−ポリスチレンスルホネート(PEDOT/PSS、Bayer社製、Baytron P Al 4083)を純水で70%に希釈した溶液を3000rpm、30秒でスピンコート法により成膜した後、200℃にて1時間乾燥し、膜厚30nmの正孔輸送層を設けた。
正孔輸送層が形成された各フィルム上に、ホスト材料として20mgのH−1を用い、発光ドーパントとして2mgのD−1をトルエン2mlに溶解した溶液を、1500rpm、30秒の条件下、スピンコート法により成膜し、120℃で1時間加熱乾燥し、膜厚40nmの発光層を設けた。
発光層まで形成した各試料を真空蒸着装置に取付け、真空槽を4×10−4Paまで減圧した。次いで、電子輸送層として、E−1(ビス(2−メチル−8−キノラート)−p−フェニルフェノラートアルミニウム錯体;BAlq)を30nm、陰極バッファー層としてフッ化リチウム1nm及び陰極としてアルミニウム110nmを蒸着して第2電極(アノード電極)を形成し、有機EL素子OEL−101〜106を作製した。
形成した第2電極上に、ポリエチレンテレフタレートを基材とし、Al2O3を厚さ300nmで蒸着した可撓性封止部材を封止膜として使用した。第1電極および第2電極の外部取り出し端子が形成出来る様に端部を除き第2電極の周囲に接着剤を塗り、可撓性封止部材を貼合した後、熱処理で接着剤を硬化させた。
Synthetic Metals,1995,68,281を参考に比較導電膜を以下のように作製した。ポリビニルアルコール(Aldrich社製、MW=115,000)0.5gに蒸留水を加え10mlとし、90℃に加熱溶解した。溶液をアルゴンパージし、The Journal of Organic Chemistry,1974,2456の方法を用いて合成したテトラフルバレンジカルボン酸 T−1 25mg(6.8×10−5mol、Fw 368.6)、フェリシアン化カリウム7.3mg(2.2×10−5mol、Fw 329.2)を温度を50℃に維持したまま添加し、10分間攪拌した。この溶液をガラス基板上へキャスティングし、膜厚10μmの比較導電膜TC−107を作製した。
テトラフルバレンジカルボン酸、フェリシアン化カリウムの添加温度を80℃、90℃に換えた以外はTC−107と同様な方法により、膜厚10μmの比較導電膜TC−108、TC−109を作製した。
作製したTC−107〜109を用いて、前記本発明の有機EL素子OEL−101〜106と同様の方法により比較有機EL素子OEL−107〜109を作製した。
本発明の有機EL素子OEL−101〜106、比較有機EL素子OEL−107〜109に対し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、23±3℃、55±3%RHの環境下で発光させた。また、本発明有機EL素子OEL−101〜106、比較有機EL素子OEL−107〜109を80℃60%RHの環境下で30分置いたのち、再び前記23±3℃、55±3%RHの環境下で1時間以上調湿した後、同様に素子を発光させた。
◎:EL素子の発光が認められる
○:EL素子の弱い発光が認められる
△:EL素子の不均一な弱い発光が認められる
×:EL素子の発光認められない
上記評価結果を表4に示す。
21 導電性材料
31 透明導電層
51 透明基材
Claims (6)
- 導電性ナノワイヤーとバインダーを含有する導電膜であって、該導電性ナノワイヤーが下記一般式(I)で表される化合物と該一般式(I)で表される化合物の酸化体の塩からなる混合原子価化合物であり、前記酸化体の塩のカウンターアニオンが下記一般式(II)で表されるアニオンであることを特徴とする導電膜。
一般式(II) R 5 COO −
〔式中、R 5 は置換基を示す。〕 - 前記一般式(I)で表される化合物のX1、X2、X3及びX4が硫黄原子であることを特徴とする請求項1記載の導電膜。
- 請求項1又は2記載の導電膜から構成される電極を用いることを特徴とする有機エレクトロルミネッセンス素子。
- 導電性ナノワイヤーとバインダーを含有し、前記導電性ナノワイヤーが下記一般式(I)で表される化合物と該一般式(I)で表される化合物の酸化体の塩からなる混合原子価化合物である導電膜の製造方法であって、
前記一般式(I)で表される化合物を含有する溶液と、前記一般式(I)で表される化合物の酸化体の塩を含有する溶液と、前記バインダーを含有する溶液とを混合後、支持体上へ塗布、乾燥する工程で製造することを特徴とする導電膜の製造方法。
- 前記一般式(I)で表される化合物のX 1 、X 2 、X 3 及びX 4 が硫黄原子であることを特徴とする請求項4記載の導電膜の製造方法。
- 前記一般式(I)で表される化合物の酸化体の塩のカウンターアニオンが下記一般式(II)表されるアニオンであることを特徴とする請求項4又は5記載の導電膜の製造方法。
一般式(II) R 5 COO −
〔式中、R 5 は置換基を示す。〕
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