JPWO2013073243A1 - 新規化合物及びこの新規化合物を担持した担持体 - Google Patents
新規化合物及びこの新規化合物を担持した担持体 Download PDFInfo
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- JPWO2013073243A1 JPWO2013073243A1 JP2013544156A JP2013544156A JPWO2013073243A1 JP WO2013073243 A1 JPWO2013073243 A1 JP WO2013073243A1 JP 2013544156 A JP2013544156 A JP 2013544156A JP 2013544156 A JP2013544156 A JP 2013544156A JP WO2013073243 A1 JPWO2013073243 A1 JP WO2013073243A1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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Abstract
Description
色素増感型光電変換素子の主たる用途の一つである太陽電池においては、その用途の特性上高い耐久性が要求されており、公知の色素及び該色素を用いた光電変換素子では未だ十分な特性を得られていない。
本発明の担持体に用いられる材料(担体)としては、アクリル樹脂、フッ素樹脂等の有機樹脂、酸化チタン、酸化亜鉛、酸化アルミニウム等の金属酸化物、酸化ケイ素、ゼオライト、活性炭等が挙げられ、表面が多孔質であるものが好ましい。担持させる化合物としては、上記一般式(1)で表される化合物であることを特徴としている。該化合物は、炭化水素オキシ基とSiとが結合したシリル基を有することで、担体への吸着力が高い。該化合物を担体に担持させる方法としては、公知の気層吸着、液層吸着等の方法を用いることが可能であるが、例えば、液層吸着の例として、本発明の化合物を溶媒に溶解し、その溶液に上記担体を浸漬することで吸着させる方法が挙げられる。
置換されていてもよい炭化水素基としては、脂肪族炭化水素基、無置換芳香族炭化水素基、脂肪族炭化水素基で置換された芳香族炭化水素基、無置換ヘテロ環基及び脂肪族炭化水素基で置換されたヘテロ環基が挙げられる。
炭素原子数1〜4の脂肪族炭化水素基としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、s−ブチル、t−ブチル、イソブチル、シクロプロピル、シクロブチル等の直鎖、分岐及び環状のアルキル基が挙げられ、炭素原子数1〜4の脂肪族炭化水素基は、−O−、−COO−、−OCO−、−CO−、−S−、−SO−、−SO2−、−NR12−、−C=C−、−C≡C−で中断されていてもよく、R12は炭素原子数1〜4の脂肪族炭化水素基であり、その例としては上記炭素原子数1〜4の脂肪族炭化水素基と同じであり、中断する基に炭素原子を含む場合、中断される基を含めた炭素原子数が1〜4である。
上記芳香族炭化水素環基としては、無置換芳香族炭化水素環基、脂肪族炭化水素基で置換された芳香族炭化水素環基等が挙げられ、上記芳香族ヘテロ環基としては、無置換芳香族ヘテロ環基、脂肪族炭化水素基で置換された芳香族ヘテロ環基等が挙げられる。
炭素原子数1〜20の脂肪族炭化水素基としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、s−ブチル、t−ブチル、イソブチル、アミル、イソアミル、t−アミル、ヘキシル、ヘプチル、イソヘプチル、t−ヘプチル、n−オクチル、イソオクチル、t−オクチル、ノニル、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、シクロノニル、シクロデシル等の直鎖、分岐及び環状のアルキル基が挙げられ、炭素原子数1〜20の脂肪族炭化水素基は、−O−、−COO−、−OCO−、−CO−、−S−、−SO−、−SO2−、−NR13−、−C=C−、−C≡C−で中断されていてもよく、R13は炭素原子数1〜20の脂肪族炭化水素基であり、その例としては上記炭素原子数1〜20の脂肪族炭化水素基と同じであり、中断する基に炭素原子を含む場合、中断される基を含めた炭素原子数が1〜20である。
上記の置換されていてもよい脂肪族炭化水素基としては、例えば前述の炭素原子数1〜20の脂肪族炭化水素基が挙げられ、それらを置換してもよい置換基は、芳香族炭化水素環基及び芳香族ヘテロ環基を置換してもよい基として挙げたものと同様である。
R7及びR8で表される上記の置換されていてもよい炭化水素基は、R1、R2及びR3で表される置換されていてもよい炭化水素基として後に挙げるものと同様である。
尚、以下には、置換基を有していないものを示しているが、上記の通り、A1は置換基を有していてもよく、A2中の水素原子は置換基で置換されていてもよい。また、以下のA(16)〜(23)において、複数の環にまたがって記載されている結合手は、それらの環を構成する炭素原子のいずれかに結合することを意味する(以下同様)。
上記芳香族炭化水素基としては、フェニル、ナフチル、シクロヘキシルフェニル、ビフェニル、ターフェニル、フルオレイル、チオフェニルフェニル、フラニルフェニル、2’−フェニル−プロピルフェニル、ベンジル、ナフチルメチル等が挙げられ、上記脂肪族炭化水素基としては、例えばA1の説明で用いた炭素原子数1〜20の脂肪族炭化水素基が挙げられ、上記脂肪族炭化水素基で置換された芳香族炭化水素基としては、上記脂肪族炭化水素基で置換されたフェニル、ナフチル、ベンジル等が挙げられる。
これらの炭化水素基を置換してもよい基としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子、シアノ基、ニトロ基、水酸基、チオール基、−NR7R8基等が挙げられ、R7及びR8が表す基は、A2において説明したR7及びR8と同様である。
尚、下記部分構造(3)及び(3−1)〜(3−12)において、A1からA2への結合手は記載を省略している。下記部分構造(3−1)〜(3−12)においては、A1からA2への結合手は、芳香族炭化水素環及び芳香族ヘテロ環を構成するいずれの炭素原子に付いていてもよい。
上記部分構造(3)を表す(3−11)及び(3−12)において、M2の金属元素としては、4配位又は6配位が可能な金属が挙げられ、より好ましくはRu、Fe、Os、Cu、W、Cr、Mo、Ni、Pd、Pt、Co、Ir、Rh、Re、Mn、Znであり、更に好ましくはRu、Fe、Os、Cuであり、特に好ましくはRuである。
本発明の光電変換素子は、色素増感型光電変換素子であり、色素として本発明の新規化合物を用いる点以外は、従来の色素増感型光電変換素子と同様とすることができる。以下、本発明の光電変換素子の代表的な構成例について、図1及び図2を参照して説明する。
作用電極10は、外部回路に対して、負極として機能するものである。導電性基板11は、例えば、絶縁性の基板11Aの表面に導電層11Bを設けたものである。
有機金属錯体化合物としては、芳香族複素環内にある窒素アニオンと金属カチオンとで形成されるイオン性の配位結合と、窒素原子又はカルコゲン原子と金属カチオンとの間に形成される非イオン性配位結合の両方を有する有機金属錯体化合物や、酸素アニオン又は硫黄アニオンと金属カチオンとで形成されるイオン性の配位結合と、窒素原子又はカルコゲン原子と金属カチオンとの間に形成される非イオン性配位結合の両方を有する有機金属錯体化合物等が挙げられる。具体的には、銅フタロシアニン、チタニルフタロシアニン、コバルトフタロシアニン、ニッケルフタロシアニン、鉄フタロシアニン等の金属フタロシアニン系色素、金属ナフタロシアニン系色素、金属ポルフィリン系色素、金属アザポルフィリン系色素ならびにルテニウム、鉄、オスミウムを用いたビピリジル金属錯体、ターピリジル金属錯体、フェナントロリン金属錯体、ビシンコニン酸金属錯体、アゾ金属錯体あるいはキノリノール金属錯体等のルテニウム錯体等が挙げられる。
MK−2 Dye(シグマアルドリッチ製、0.10mmol、96mg)、塩化オキサリル(0.11mmol、14mg)、ジメチルホルムアミド(0.01ml)及びクロロホルム(2ml)をフラスコに仕込み、25℃で1時間撹拌した。10℃まで冷却した後、N,N−ジイソプロピルエチルアミン(0.20mmol、26mg)及び(トリエトキシシリルメチル)ヘキシルアミン(0.10mmol、28mg)を加えて、更に1時間撹拌した。反応液に水(2ml)を加え、油水分液を行った。得られた有機層をシリカゲルカラムクロマトグラフィー(移動相;クロロホルム)により精製することにより、紫色固体を108mg(収率89%)得た。得られた固体が、化合物No.1であることをUV−VIS(λmax)、1H−NMRを用いて確認した。データを〔表1〕及び〔表2−1〕に示す。
目的化合物に対応したカルボン酸又はスルホン酸を有する化合物及びアミン化合物を用いた以外は合成例1と同様の手法で化合物No.2〜No.24、61、62、70〜72を合成した。得られた化合物の外観及び収率を〔表1〕に示す。合成した化合物が目的化合物であることは、合成例1と同様に確認した。データを〔表1〕、〔表2−1〕、〔表2−2〕及び〔表2−3〕に示す。
まず、縦2.0cm×横1.5cm×厚さ1.1mmの導電性ガラス基板(F−SnO2)よりなる導電性基板11を用意した。続いて、導電性基板11に、縦0.5cm×横0.5cmの四角形を囲むように厚さ70μmのマスキングテープを貼り、この部分に金属酸化物スラリー3cm3を一様の厚さとなるように塗布して乾燥させた。金属酸化物スラリーとしては、10重量%となるように酸化チタン粉末(TiO2、Solaronix社製Ti−NanoxideD)を、水に懸濁したものを用いた。続いて、導電性基板11上のマスキングテープを剥がし取り、この基板を電気炉により450℃で焼成し、厚さ約5μmの金属酸化物半導体層12を形成した。続いて、化合物No.1を3×10-4mol/dm3の濃度になるようにトルエンに溶解させて、色素溶液を調製した。続いて、金属酸化物半導体層12が形成された導電性基板11を上記の色素溶液に浸漬し、色素13を担持させた作用電極10を作製した。
作製した作用電極10を25℃、24時間の条件で、剥離液(アセトニトリル:水=99:1)に浸漬した。剥離液浸漬前の色素担持量(色素のλmaxにおけるAbs.)を100としたときの、剥離液浸漬後の色素担持量(剥離液浸漬前の色素担持量に対する割合)を、耐剥離性として〔表3〕に示した。剥離後の色素担持量が100に近いほど耐剥離性が高いといえる。
化合物No.1を〔表3〕の化合物に替えた以外は実施例1と同様の操作により、各化合物を担持させた作用電極10を作製し、色素の耐剥離性を求めた。結果を〔表3〕に示す。
(実施例30〜42及び比較例5〜8)
図1に示すように、上記実施例1〜11、27〜29及び比較例1〜4で作製した担持体(作用電極)を用いた作用電極10と、導電性基板21としてITO電極(西野田電工(株)製)上に黒鉛微粒子(導電層22)をコーティングして作製した対向電極20とを、スペーサー(63μm)を介して対向させ、それらの間に電解質含有層30を配し、これらをクリップで固定し、電解質含有層30に電解液〔アセトニトリルに対して、4−t−ブチルピリジン(0.5mol/dm3)、ヨウ化リチウム(0.5mol/dm3)、ヨウ素(0.05mol/dm3)を、それぞれ所定の濃度になるように混合したもの〕を浸透させ、光電変換素子を作製した。セル上部を開口部1cm2のマスクで覆い、AM−1.5(1000W/m2)のソーラーシミュレーターを用いて変換効率を測定した。結果を、〔表4〕に示す。
(実施例43〜45及び比較例9)
化合物No.1を〔表4A〕の化合物に替え、酸化チタン粉末を酸化亜鉛(ZnO、ソーラー社製)に変更した以外は実施例1と同様の操作により、各化合物を担持させた作用電極10を作製した。得られた作用電極10を用いて、実施例30と同様の操作により変換効率を測定した。結果を〔表4A〕に示す。
上記実施例4、7及び比較例1、2で作製した担持体(作用電極)について耐光性評価を行った。評価は、該作用電極に55000ルクスの光を4時間照射し、UV吸収スペクトルのλmaxの変化を、照射前を100として算出した。具体的には、λmaxにおける照射後のAbs.及び照射前のAbs.を測定し、「(照射後のAbs./照射前のAbs.)×100」を求め、耐光性の値とした。結果を〔表5〕に示す。
Claims (8)
- 下記一般式(1)で表される新規化合物。
但し、Yは、下記の部分構造式(Y−11)及び(Y−12)で表わされる基を除く。)
- 上記一般式(1)におけるR1、R2及びR3が、直鎖又は分岐鎖脂肪族炭化水素オキシ基である請求項1に記載の新規化合物。
- 上記一般式(1)におけるZが、下記部分構造式(2)で表される請求項1〜3の何れか一項に記載の新規化合物。
- 上記一般式(1)におけるR1、R2及びR3が、直鎖又は分岐鎖脂肪族炭化水素オキシ基である請求項6に記載の担持体。
- 請求項6又は7に記載の担持体を有する電極を備えた光電変換素子。
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CN103827126B (zh) | 2017-05-17 |
TW201321391A (zh) | 2013-06-01 |
EP2781555A4 (en) | 2015-10-07 |
US9530571B2 (en) | 2016-12-27 |
TWI598354B (zh) | 2017-09-11 |
US20140261647A1 (en) | 2014-09-18 |
JP6145407B2 (ja) | 2017-06-14 |
WO2013073243A1 (ja) | 2013-05-23 |
KR20140094507A (ko) | 2014-07-30 |
CN103827126A (zh) | 2014-05-28 |
EP2781555A1 (en) | 2014-09-24 |
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