JP5741366B2 - 透明電極の製造方法 - Google Patents
透明電極の製造方法 Download PDFInfo
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- JP5741366B2 JP5741366B2 JP2011227558A JP2011227558A JP5741366B2 JP 5741366 B2 JP5741366 B2 JP 5741366B2 JP 2011227558 A JP2011227558 A JP 2011227558A JP 2011227558 A JP2011227558 A JP 2011227558A JP 5741366 B2 JP5741366 B2 JP 5741366B2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- VELSFHQDWXAPNK-UHFFFAOYSA-N tetracontacyclo[25.6.5.516,28.44,32.35,11.321,34.28,10.212,15.222,35.229,31.113,20.124,38.02,6.014,19.017,25.018,23.030,37.033,36.547,54.446,53.448,58.126,51.150,52.03,45.07,42.09,61.039,40.041,43.044,63.049,76.055,78.056,62.057,68.059,64.060,67.065,69.066,71.070,73.072,75.074,77]octaheptaconta-1,3(45),4(48),5(61),6,8,10,12,14,16,18,20,22,24(39),25,27(38),28,30,32,34(42),35(40),36,41(43),44(63),46,49(76),50(77),51,53,55(78),56(62),57,59,64,66,68,70(73),71,74-nonatriacontaene Chemical compound c12c3c4c5c6c1c1c7c8c2c2c3c3c9c4c4c5c5c%10c%11c%12c%13c%14c%15c%12c%12c%16c%17c%18c%19c%20c%21c%17c%17c%22c%21c%21c%23c%20c%20c%19c%19c%24c%18c%16c%15c%15c%24c%16c(c7c%15c%14c1c6c5%13)c8c1c2c2c3c3c(c%21c5c%22c(c%11c%12%17)c%10c4c5c93)c%23c2c%20c1c%19%16 VELSFHQDWXAPNK-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
- MPKQTNAUFAZSIJ-UHFFFAOYSA-N thiophene-3,4-diol Chemical compound OC1=CSC=C1O MPKQTNAUFAZSIJ-UHFFFAOYSA-N 0.000 description 1
- GSXCEVHRIVLFJV-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical compound N#CC=1C=CSC=1 GSXCEVHRIVLFJV-UHFFFAOYSA-N 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001456 vanadium ion Inorganic materials 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Landscapes
- Photovoltaic Devices (AREA)
- Electroluminescent Light Sources (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
1.透明基板上に、金属ナノ粒子より形成された導電性の金属細線パターンと、該金属細線パターン上に少なくともπ共役系導電性高分子とポリ陰イオンとを含んでなる導電性ポリマー含有層とを有する透明電極の製造方法であって、該金属細線パターンを加熱焼成する前に該金属細線パターン上に該導電性ポリマー含有層を形成し、その後に、フラッシュ光照射により加熱焼成を行うことを特徴とする透明電極の製造方法。
2.前記導電性ポリマー含有層が、少なくとも前記π共役系導電性高分子とポリ陰イオン
とを含んでなる導電性ポリマーと下記一般式(I)で表される構造単位を含む水溶性バイ
ンダー樹脂を有することを特徴とする前記1項に記載の透明電極の製造方法。
本発明の透明電極に用いられる透明基板としては、高い光透明性を有していれば、特に制限はない。例えば樹脂基板、樹脂フィルム、ガラス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。
本発明の金属細線パターンは、金属ナノ粒子より形成されることを特徴とする。金属ナノ粒子の金属材料は、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が、導電性及び安定性の観点から銀であることが好ましい。
本発明に係る導電性ポリマー含有層は、少なくとも、π共役系導電性高分子とポリ陰イオンとを含んでなる導電性ポリマーから形成される。本発明の透明電極において、前記導電性ポリマー含有層が、少なくともπ共役系導電性高分子とポリ陰イオンとを含んでなる導電性ポリマーと前記一般式(I)で表される構造単位を含む水溶性バインダー樹脂とから形成されることが、高い透明性と導電性を保持したまま、高い表面平滑性が得られる点から好ましい。
本発明に係る導電性ポリマーは、π共役系導電性高分子とポリ陰イオンとを含んでなる。こうした導電性ポリマーは、後述するπ共役系導電性高分子を形成する前駆体モノマーを、適切な酸化剤と酸化触媒と後述のポリ陰イオンの存在下で化学酸化重合することによって容易に製造できる。
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、及び、金属ナノ粒子への吸着のしやすさから、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、遊離酸状態の酸性ポリマーであり、アニオン基を有するモノマーの重合体、あるいはアニオン基を有するモノマーとアニオン基を有しないモノマーとの共重合体である。遊離酸は、一部が中和された塩の形をとっていてもよい。
本発明の導電性ポリマー含有層においては、少なくとも前記一般式(I)で表される構造単位を含む水溶性バインダー樹脂を含有することが好ましい。こうした樹脂は導電性ポリマーと容易に混合可能で、また、前述の第二ドーパント的な効果も有するため、該水溶性バインダー樹脂を併用することにより、導電性、透明性を低下させることなく、導電性ポリマー含有層の膜厚を上げることが可能となる。膜厚を上げることで、高い表面平滑性が得られ、また金属細線パターンを導電性ポリマー含有層で十分に覆うことが可能となり、有機発光デバイスや有機太陽電池デバイス等の電極に使用した場合でも整流比に優れ電極間のリークを防ぐことが可能となる。
本発明のフラッシュランプを用いた光照射による加熱焼成は、金属ナノ粒子より形成された導電性の金属細線パターンを焼成して、その導電性を向上させるために行う。
本発明における透明電極の全光線透過率は、70%以上、好ましくは80%以上であることが望ましい。全光線透過率は、分光光度計等を用いた公知の方法に従って測定することができる。
本発明における有機電子素子は、本発明の方法で製造された透明電極と有機機能層とを有する。
〈有機機能層構成〉
〔有機発光層〕
本発明において、有機機能層としての有機発光層を有する有機EL素子は、有機発光層に加えて、ホール注入層、ホール輸送層、電子輸送層、電子注入層、ホールブロック層、電子ブロック層などの発光を制御する層を有機発光層と併用しても良い。
(ii)(第一電極部)/正孔輸送層/発光層/電子輸送層/(第二電極部)
(iii)(第一電極部)/正孔輸送層/発光層/正孔ブロック層/電子輸送層/(第二電極部)
(iv)(第一電極部)/正孔輸送層/発光層/正孔ブロック層/電子輸送層/陰極バッファー層/(第二電極部)
(v)(第一電極部)/陽極バッファー層/正孔輸送層/発光層/正孔ブロック層/電子輸送層/陰極バッファー層/(第二電極部)
ここで、発光層は、発光極大波長が各々430〜480nm、510〜550nm、600〜640nmの範囲にある単色発光層であってもよく、また、これらの少なくとも3層の発光層を積層して白色発光層としたものであってもよく、さらに発光層間には非発光性の中間層を有していてもよい。本発明の有機EL素子としては、白色発光層であることが好ましい。
本発明の透明電極は、上記の第一、又は第二電極部で使用される。第一電極部が陽極で第二電極部が陰極であることが好ましい態様である。
有機光電変換素子は、第一電極部、バルクヘテロジャンクション構造(p型半導体層及びn型半導体層)を有する光電変換層(以下、バルクヘテロジャンクション層とも呼ぶ)、第二電極部が積層された構造を有することが好ましい。本発明の透明電極は、少なくとも入射光側に用いられる。
光電変換層は、光エネルギーを電気エネルギーに変換する層であって、p型半導体材料とn型半導体材料とを一様に混合したバルクヘテロジャンクション層を構成していることが好ましい。p型半導体材料は、相対的に電子供与体(ドナー)として機能し、n型半導体材料は、相対的に電子受容体(アクセプター)として機能する。
(導電性ポリマー液CP−1の調製)
(水溶性バインダー樹脂1(構造単位;例示化合物I−1)の合成)
300ml三ツ口フラスコにテトラヒドロフラン(THF)200ml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(10.0g、86.2mmol、分子量116.12)、アゾビスブチロニトリル(AIBN)(2.8g、17.2mmol、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、2000mlのMEK中に反応溶液を滴下し、1時間攪拌した。MEKをデカンテーション後、100mlのMEKで3回洗浄後、THFでポリマーを溶解し、100mlフラスコへ移した。THFをロータリーエバポレーターにより減圧留去後、50℃で3時間減圧乾燥した。その結果、数平均分子量22100、分子量分布1.42の水溶性バインダー樹脂1を9.0g(収率90%)得た。
装置:Waters2695(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℃
得られた水溶性バインダー樹脂1を純水に溶解し、固形分20%の水溶性バインダー樹脂1水溶液を調製した。
水溶性バインダー樹脂1水溶液(固形分20%水溶液) 0.40g
PEDOT−PSS CLEVIOS PH750(固形分1.03%)
(Heraeus社製) 1.90g
ジメチルスルホキシド 0.10g
(導電性ポリマー液CP−2、3の調製)
(水溶性バインダー樹脂2、水溶性バインダー樹脂3の合成)
水溶性バインダー樹脂1(構造単位;例示化合物I−1)の合成において、2−ヒドロキシエチルアクリレートを3−ヒドロキプロピルアクリレート(11.2g、分子量130.14)、4−ヒドロキシブチルアクリレート(12.4g、分子量144.17)に変え、更に精製溶媒をMEKからノルマルヘプタンに変更した以外は全く同操作を実施することにより、数平均分子量25500、分子量分布1.53水溶性バインダー樹脂2を9.5g(収率85%)、数平均分子量21700、分子量分布1.36の水溶性バインダー樹脂3を10.2g(収率82%)得た。
ついで導電性ポリマー液CP−1の調整において、水溶性バインダー樹脂1をそれぞれ同質量の水溶性バインダー樹脂2、3に変えることにより、導電性ポリマー液CP−2、3を得た。
<水溶性バインダー樹脂4の合成>
水溶性バインダー樹脂1(構造単位;例示化合物I−1)の合成において、2−ヒドロキシエチルアクリレートを2−ヒドロキシエチルアクリルアミド(9.9g、分子量115.15)に変え、更に精製溶媒をMEKからジイソプロピルエーテルに変更した以外は全く同操作を実施することにより、数平均分子量28300、分子量分布1.48の水溶性バインダー樹脂4を7.9g(収率80%)得た。
ついで導電性ポリマー液CP−1の調整において、水溶性バインダー樹脂1を同質量の水溶性バインダー樹脂4に変えることにより、導電性ポリマー液CP−4を得た。
〔透明電極TCF−1の作製(比較例)〕
下記の方法で両面にガスバリア層を設けた、厚さ100μm、大きさ180mm×180mmのポリエチレンテレフタレートフィルム基板上に、150mm×150mmの面積大にITOを平均膜厚150nmで蒸着し、透明電極TCF−1を作製した。
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
〔透明電極TCF−2の作製(比較例)〕
TCF−1同様に両面にガスバリア層を設けた、厚さ100μm、大きさ180mm×180mmの二軸延伸ポリエチレンテレフタレート樹脂フィルム基板上に、銀ナノ粒子インキ1(TEC−PA−010;InkTec社製)を用いて、50μm幅、1mmピッチ、正方形格子状のスクリーン版パターンにて、小型厚膜半自動印刷機STF−150IP(東海商事社製)を用い、焼成後の細線の高さが800nmになるようスクリーン印刷方式で金属細線パターンの印刷を行った。パターンを印刷するエリアの面積は150mm×150mmとした。
透明電極TCF−2において、導電性ポリマー含有層を樹脂フィルム基板上に塗布する前に、250nm以下の短波長カットフィルターを装着したキセノンランプ2400WS(COMET社製)を用いて、金属細線パターンを、印刷面側から照射エネルギー1.5J/cm2、照射時間2000μ秒で1回照射する以外はTCF−2と同様にして、透明電極TCF−3を作製した。透明電極TCF−3は、導電性ポリマー含有層を塗布した際に、金属細線パターン上で部分的に導電性ポリマー含有層のハジキが見られた。
透明電極TCF−3において、導電性ポリマー含有層を樹脂フィルム基板上に塗布した後にフラッシュランプ照射する以外はTCF−2と同様にして、透明電極TCF−4を作製した。
透明電極TCF−4において、フラッシュランプ照射条件を、照射エネルギー1.2J/cm2、照射時間1000μ秒で1回行う以外はTCF−4と同様にして、透明電極TCF−5を作製した。
透明電極TCF−4において、フラッシュランプ照射条件を、照射エネルギー1.8J/cm2、照射時間500μ秒で1回行う以外はTCF−4と同様にして、透明電極TCF−6を作製した。
透明電極TCF−4において、フラッシュランプ照射条件を、照射エネルギーの総計1.0J/cm2、照射時間2000μ秒で3回均等に行う以外はTCF−4と同様にして、透明電極TCF−7を作製した。
透明電極TCF−4において、アプリケーターのギャップを調整し、導電性ポリマー含有層の乾燥膜厚が250nmとなるよう樹脂フィルム基板上に塗布する以外はTCF−4と同様にして、透明電極TCF−8を作製した。
透明電極TCF−4において、アプリケーターのギャップを調整し、導電性ポリマー含有層の乾燥膜厚が850nmとなるよう樹脂フィルム基板上に塗布する以外はTCF−4と同様にして、透明電極TCF−9を作製した。
透明電極TCF−4において、導電性ポリマー液CP−1の代わりに導電性ポリマー液CP−2を用いて本発明の例示化合物I−3とする以外はTCF−4と同様にして、透明電極TCF−10を作製した。
透明電極TCF−4において、導電性ポリマー液CP−1の代わりに導電性ポリマー液CP−3を用いて本発明の例示化合物I−4とする以外はTCF−4と同様にして、透明電極TCF−11を作製した。
透明電極TCF−4において、導電性ポリマー液CP−1の代わりに導電性ポリマー液CP−4を用いて本発明の例示化合物I−19とする以外はTCF−4と同様にして、透明電極TCF−12を作製した。
下記方法で、各透明電極の導電部の透過率、表面比抵抗について測定し、透明性と導電性を評価した。
透過率は、東京電色社製AUTOMATICHAZEMETER(MODEL TC−HIIIDP)を用いて、透明電極の全光線透過率を測定した。
表面比抵抗は、ダイアインスツルメンツ製抵抗率計ロレスタGPを用いて透明電極の表面比抵抗を四端子法で測定した。
各透明電極を第一電極(陽極)に用いて、以下の手順でそれぞれ有機EL素子OLED−1〜12を作製した。
下記方法で、上記のように作製した各有機EL素子の整流比、発光ムラ、電圧値を測定し、有機EL素子の発光均一性、駆動電圧を評価した。
整流比は、各有機EL素子に、+4V/−4Vの電圧を印加した時の電流値を測定し、下記の計算式により整流比を求め、下記基準で評価した。電極間リークがあると、整流比が低い値となる。102以上であることが実用的範囲である。
◎:整流比103以上
○:整流比102以上103未満
△:整流比101以上102未満
×:整流比101未満
(発光ムラ)
発光ムラは、KEITHLEY製ソースメジャーユニット2400型を用いて、各有機EL素子に直流電圧を印加して輝度が1000cd/m2になるよう発光させ、発光状態を下記基準で目視評価した。
○:ほぼ均一発光しており、実用的に問題ない
△:部分的に発光ムラが見られ、実用的に許容できない
×:全面に渡って発光ムラが見られ、全く許容できない
(駆動電圧)
駆動電圧は、KEITHLEY製ソースメジャーユニット2400型を用いて、各有機EL素子に直流電流を印加して輝度が1000cd/m2になるよう発光させ、1000cd/m2での電圧値を測定した。電圧値が低いほど駆動電圧が低く、5V以下が実用的範囲である。
例示:例示化合物
HP:ホットプレート
FL照射:フラッシュランプ照射
塗布前:導電性ポリマー含有層塗布前
塗布後:導電性ポリマー含有層塗布後
Claims (3)
- 透明基板上に、金属ナノ粒子より形成された導電性の金属細線パターンと、該金属細線パターン上に少なくともπ共役系導電性高分子とポリ陰イオンとを含んでなる導電性ポリマー含有層とを有する透明電極の製造方法であって、該金属細線パターンを加熱焼成する前に該金属細線パターン上に該導電性ポリマー含有層を形成し、その後に、フラッシュ光照射により加熱焼成を行うことを特徴とする透明電極の製造方法。
- 前記透明基板が二軸延伸ポリエステル樹脂フィルムであることを特徴とする請求項1又は2に記載の透明電極の製造方法。
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