JP5914462B2 - 新規化合物及び光電変換素子 - Google Patents
新規化合物及び光電変換素子 Download PDFInfo
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- JP5914462B2 JP5914462B2 JP2013508797A JP2013508797A JP5914462B2 JP 5914462 B2 JP5914462 B2 JP 5914462B2 JP 2013508797 A JP2013508797 A JP 2013508797A JP 2013508797 A JP2013508797 A JP 2013508797A JP 5914462 B2 JP5914462 B2 JP 5914462B2
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- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical class I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 description 1
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- FBLZDUAOBOMSNZ-UHFFFAOYSA-M tetrapentylazanium;iodide Chemical compound [I-].CCCCC[N+](CCCCC)(CCCCC)CCCCC FBLZDUAOBOMSNZ-UHFFFAOYSA-M 0.000 description 1
- GKXDJYKZFZVASJ-UHFFFAOYSA-M tetrapropylazanium;iodide Chemical compound [I-].CCC[N+](CCC)(CCC)CCC GKXDJYKZFZVASJ-UHFFFAOYSA-M 0.000 description 1
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- KKLAORVGAKUOPZ-UHFFFAOYSA-M trimethyl(phenyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)C1=CC=CC=C1 KKLAORVGAKUOPZ-UHFFFAOYSA-M 0.000 description 1
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Images
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- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
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- C09B23/162—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
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- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
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- C09B29/0805—Amino benzenes free of acid groups
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- H01G9/20—Light-sensitive devices
- H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
- H01G9/2031—Light-sensitive devices comprising an oxide semiconductor electrode comprising titanium oxide, e.g. TiO2
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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。
また、本発明は、上記担持体を有する電極を備えた光電変換素子を提供するものである。
上記一般式(1)におけるAが表す基は、2価の基であり、置換されていてもよい芳香族炭化水素環基又は置換されていてもよい芳香族ヘテロ環基である。
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−、−NR6−、−C=C−、−C≡C−で中断されていてもよく、R6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、Aは置換基を有していてもよく、B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−B(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A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、B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(2)及び(2−1)〜(2−4)において、AからBへの結合手は記載を省略している。下記部分構造(2−1)〜(2−4)においては、AからB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。
尚、下記部分構造(3)、(3−1)及び(3−2)において、BからSi原子への結合手は記載を省略している。下記部分構造(3−1)及び(3−2)においては、BからSi原子への結合手は、右端の環構造中のいずれかの炭素原子に付く。
i)Bが表す基の中に、上記式(B−1)〜(B−9)及び(B−11)〜(B−13)の何れかで表される基を少なくとも一つ有する。
ii)R4及びR5が、置換されていてもよい炭素原子数1〜12の炭化水素基である。
iii)R4及びR5の少なくとも一つが、Aと連結して環を形成している。
上記i)の条件を満たす化合物は、担体への電子注入効率が特に高い点で好ましい。上記ii)の条件を満たす化合物は、製造が容易であり、担持体への吸着モル数が特に大きい点で好ましい。上記iii)の条件を満たす化合物は、光電変換素子の耐久性が特に高い点で好ましい。
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。本発明の新規化合物は、アルコキシシリル基を有することで、担体への吸着力が高い。本発明の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。
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。
4−(4−ブロモフェニルアゾ)−N,N−ジメチルアニリン(ハロゲン体、2.0mmol、0.60g)、トリエトキシシラン(シリル化剤、3.0mmol、0.49g)、トリス(ジベンジリデンアセトン)ジパラジウム(0.03mmol、0.027g)、(2−ビフェニル)ジターシャリーブチルホスフィン(0.12mmol、0.036g)、N,N−ジイソプロピルエチルアミン(6.0mmol、0.78g)及びジメチルホルムアミド(4ml)を仕込み、60℃で3時間撹拌した。室温まで冷却した後、反応液にクロロホルム(10ml)及び水(10ml)を加え、油水分液を行った。得られた有機層をPLC(ヘキサン:酢酸エチル=15:1の移動相溶媒)を用いて精製することにより、黄色固体を0.35g(収率45.2%)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〕〜〔表2〕に示す。
目的化合物に対応したハロゲン体(ブロモ体)及びシリル化剤を用いた以外は合成例1と同様の手法で化合物No.2〜No.25及びNo.66〜No.68を合成した。得られた固体又は液体の外観及び収率を〔表1〕に示す。尚、PLCによる精製時に用いた移動相溶媒は化合物によって異なるため、移動相溶媒についても合わせて〔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〕及び〔表2〕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。
金属スラリー及び化合物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、各色素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〕に示した。尚、〔表3〕に記載の金属スラリーのZnOとしては、酸化亜鉛粉末(平均粒径20nm、堺化学工業社製FINEX−50)を用いた。
Claims (5)
- 下記一般式(1A)又は下記一般式(1B)で表される化合物。
(式(1A)中におけるB及びNR4R5と結合する芳香族ヘテロ環基は置換されていてもよい。また式(1B)中におけるB及びNR5と連結する芳香族炭化水素環基は置換されていてもよく、該芳香族炭化水素環基及びNR5と連結する芳香族炭化水素基は置換されていてもよい。式(1A)及び(1B)において、Bは下記式(B−1)、(B−6)〜(B−8)及び(B−10)〜(B−13)で表される基から選ばれる基を1〜4個連結した基であり、R1、R2及びR3は、置換されていてもよい炭化水素基又は炭化水素オキシ基を表し、R1、R2及びR3の少なくとも一つが置換されていてもよい炭化水素オキシ基であり、R4及びR5は、置換されていてもよい炭化水素基を表す。式(1A)中におけるR4及びR5は互いに連結して環を形成してもよく、式(1B)中におけるR5は、上記芳香族炭化水素基と連結して環を形成してもよく、式(1A)中におけるR4及びR5は互いに独立して上記芳香族ヘテロ環基と連結して環を形成してもよく、式(1B)中におけるR5は、上記芳香族炭化水素環基と連結して環を形成してもよい。)
- 更に以下の条件i)〜iii)の少なくとも一つを満たす請求項1に記載の新規化合物。
i)Bが表す基の中に、上記式(B−1)、(B−6)〜(B−8)及び(B−11)〜(B−13)の何れかで表される基を少なくとも一つ有する。
ii)上記一般式(1A)で表され、R4及びR5が、置換されていてもよい炭素原子数1〜12の炭化水素基であるか、あるいは、上記一般式(1B)で表され、R5が、置換されていてもよい炭素原子数1〜12の炭化水素基である。
iii)上記一般式(1A)で表され、R4及びR5の少なくとも一つが、上記芳香族ヘテロ環基と連結して環を形成しているか、あるいは、上記一般式(1B)で表され、R5が、上記芳香族炭化水素環基と連結して環を形成している。 - 上記一般式(1A)及び(1B)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又は2記載の新規化合物。
- 請求項1〜3の何れか一つに記載の新規化合物を担持した担持体。
- 請求項4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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KR101874496B1 (ko) | 2018-07-04 |
TWI560246B (ja) | 2016-12-01 |
TW201243000A (en) | 2012-11-01 |
CN103415527A (zh) | 2013-11-27 |
EP2695886A1 (en) | 2014-02-12 |
US20130341572A1 (en) | 2013-12-26 |
US9812263B2 (en) | 2017-11-07 |
CN103415527B (zh) | 2016-06-29 |
JPWO2012137568A1 (ja) | 2014-07-28 |
KR20140056159A (ko) | 2014-05-09 |
EP2695886A4 (en) | 2014-12-03 |
US20160211085A1 (en) | 2016-07-21 |
US9324889B2 (en) | 2016-04-26 |
WO2012137568A1 (ja) | 2012-10-11 |
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