JP2010157373A - 光電変換素子用色素および光電変換素子 - Google Patents
光電変換素子用色素および光電変換素子 Download PDFInfo
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- JP2010157373A JP2010157373A JP2008333597A JP2008333597A JP2010157373A JP 2010157373 A JP2010157373 A JP 2010157373A JP 2008333597 A JP2008333597 A JP 2008333597A JP 2008333597 A JP2008333597 A JP 2008333597A JP 2010157373 A JP2010157373 A JP 2010157373A
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- VRKHAMWCGMJAMI-UHFFFAOYSA-M tetrahexylazanium;iodide Chemical compound [I-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC VRKHAMWCGMJAMI-UHFFFAOYSA-M 0.000 description 1
- 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
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
【解決手段】作用電極10および対向電極20と共に電解質含有層30を備え、作用電極10には、色素13を担持した金属酸化物半導体層12が設けられている。色素13は、シアニン化合物を含み、そのシアニン化合物は、メチン鎖の両端に結合したインドレニン骨格を含む複素環骨格と、そのインドレニン骨格が含む窒素原子に導入されたアンカー基と、複素環骨格のうちの一方が有するフェナンスレン骨格とを有する。色素13に光が入射すると、金属酸化物半導体層12に対する電子注入効率が高くなる。
【選択図】図1
Description
上記実施の形態で説明した色素の具体例として、上記した式(I)、式(III )および式(IV)の化学反応式に示した手順に従って、式(1)に示したシアニン化合物として式(4)に示した化合物である式(8)に示した構造部およびヨウ化物イオンからなる化合物を合成した。
式(9)に示した構造部およびヨウ化物イオンからなる化合物を合成した。この際、まず、実験例1−1の式(I−1)の化学反応式に示した手順と同様にして式(286−1)に示した4級アンモニウム塩を用意した。その一方で、式(I−3)の化学反応式に示したように、式(298−1)に示した化合物に代えて、式(298−2)で表される化合物を用いたことを除き、実験例1−1の式(I−2)の化学反応式に示した手順と同様にして式(291−2)で表される4級アンモニウム塩を得た。
式(11)に示した構造部およびヨウ化物イオンからなる化合物を合成した。この際、まず、式(IV−3)の化学反応式に示したように、式(286−2)で表される4級アンモニウム塩を用意すると共に、実験例1−2の式(I−3)および式(III −2)の化学反応式に示した手順と同様にして式(290−2)に示したシアニン中間体を用意した。続いて、式(286−1)に示した4級アンモニウム塩に代えて、式(286−2)で表される4級アンモニウム塩を用いたことを除き、実験例1−2の式(IV−2)の化学反応式に示した手順と同様にして、最終生成物(式(11−1)で表される化合物)を得た。この最終生成物の収率は16%であった。
式(13)に示した構造部およびヨウ化物イオンからなる化合物を合成した。この際、まず、式(IV−4)の化学反応式に示したように、式(286−3)で表される4級アンモニウム塩を用意すると共に、実験例1−2の式(I−3)および式(III −2)の化学反応式に示した手順と同様にして式(290−2)に示したシアニン中間体を用意した。続いて、式(286−1)に示した4級アンモニウム塩に代えて、式(286−3)に示した4級アンモニウム塩を用いたことを除き、実験例1−2の式(IV−2)の化学反応式に示した手順と同様にして、最終生成物(式(13−1)で表される化合物)を得た。この最終生成物の収率は4.5%であった。
上記した式(I)および式(V)の化学反応式に示した手順に従って、式(14)に示した構造部およびヨウ化物イオンからなる化合物を合成した。この際、まず、式(286−2)に示した4級アンモニウム塩を用意した。そののち、式(V−1)の化学反応式に示したように、式(286−2)に示した4級アンモニウム塩10mmolと、式(289−6)に示したブリッジ剤5mmolと、無水酢酸20mmolと、塩基としてトリメチルアミン10mmolと、アセトニトリル(CH3 CN)10gとを混合し、その混合物を4時間加熱還流して反応させた。最後に、この反応物に対してクロロホルム10gと水10gとを加えたのち、析出した固体をろ別後、減圧乾燥することにより、4.2%の収率で最終生成物(式(14−1)で表される化合物)を得た。
式(15)に示した構造部およびヨウ化物イオンからなる化合物を合成した。この際、まず、式(III −3)の化学反応式に示したように、式(286−2)に示した4級アンモニウム塩を用意すると共に、実験例1−1の式(I−2)の化学反応式に示した手順と同様にして式(291−1)に示した4級アンモニウム塩を用意した。続いて、式(289−5)に示したブリッジ剤に代えて式(289−7)に示したブリッジ剤を用いたことを除き、実験例1−1の式(III −1)の化学反応式に示した手順と同様にして、式(290−3)で表されるシアニン中間体を得た。
実験例1−1で合成した式(8−1)に示した化合物を用いて、上記実施の形態で説明した光電変換素子の具体例として色素増感型太陽電池を以下の手順により作製した。
色素として、式(8−1)に示した化合物に代えて、実験例1−2で合成した式(9−1)に示した化合物(実験例2−2)、式(10−1)で表される化合物(実験例2−3)、実験例1−3で合成した式(11−1)に示した化合物(実験例2−4)、式(12−1)で表される化合物(実験例2−5)、実験例1−4で合成した式(13−1)に示した化合物(実験例2−6)、実験例1−5で合成した式(14−1)に示した化合物(実験例2−7)あるいは実験例1−6で合成した式(15−1)に示した化合物(実験例2−8)を用いたことを除き、実験例2−1と同様の手順を経た。なお、実験例として具体的な合成手順および最終合成物の物性データ等を示していないが、式(10−1)に示した化合物および式(12−1)に示した化合物についても上記した実験例1−1等と同様にして合成することができる。
実験例2−1〜2−8に対する比較例として、色素である式(8−1)に示した化合物に代えて、以下の式(299)〜式(305)に示した化合物(色素)を用いたことを除き、実験例2−1と同様の手順を経た。
電解析出法により金属酸化物半導体層12を形成したことを除き、実験例2−1〜2−15と同様の手順を経た。電解析出法により金属酸化物半導体層12を形成する場合には、以下の手順により行った。まず、水に対してエオシンY(30μmol/dm3 )、塩化亜鉛(5mmol/dm3 )、塩化カリウム(0.09mol/dm3 )の濃度になるように調製した電解浴液40mlと、亜鉛板よりなる対極と、銀/塩化銀電極よりなる参照電極とを用意した。続いて、電解浴を酸素により15分間バブリングしたのち、電解浴中の溶液の温度を70℃とし、60分、電位−1.0Vの定電位電解をバブリングしながら導電性基板11の表面に製膜した。最後に、この基板を、乾燥させることなく水酸化カリウム水溶液(pH11)に浸漬し、そののち水洗することによりエオシンYを脱着した。続いて、150℃、30分間乾燥させた。
焼成法により金属酸化物半導体層12を形成する際に、酸化亜鉛粉末に代えて、酸化チタン(TiO2 )粉末を含む金属酸化物スラリーを用いたことを除き、実験例2−1〜2−15と同様の手順を経た。この場合、酸化チタン粉末を含む金属酸化物スラリーは、以下のように調製した。まず、チタンイソプロポキシド125cm3 を、0.1mol/dm3 硝酸水溶液750cm3 に攪拌しながら添加し、80℃で8時間激しく攪拌した。得られた液体をテフロン(登録商標)製の圧力容器に注ぎ入れ、その圧力容器を230℃、16時間オートクレーブにて処理した。そののちオートクレーブ処理した沈殿物を含む液体(ゾル液)を攪拌することにより再懸濁させた。続いて、この懸濁液を吸引濾過して再懸濁しなかった沈殿物を除き、ゾル状の濾液をエバポレータで酸化チタン濃度が11質量%になるまで濃縮した。こののち、濃縮液に基板への塗れ性を高めるためにTriton X-100を1滴添加した。続いて、平均粒径30nmの酸化チタン粉末(日本アエロジル社製P−25)をこのゾル状の濃縮液に、酸化チタンの含有率が全体として33質量%となるように加え、自転公転を利用した遠心撹拌を1時間行い、分散させた。
焼成法により金属酸化物半導体層12を形成する際に、酸化亜鉛粉末に代えて、酸化錫(SnO2 )粉末を用いたことを除き、実験例2−1〜2−15と同様の手順を経た。この場合、酸化錫粉末として、表面積50m2 /g、平均一次粒径30nm以下のもの(ジェムコ社製S−2000)を用いた。
Claims (17)
- 色素と、この色素を担持した担持体とを有する電極を備え、
前記色素は、式(1)で表されるシアニン化合物を含む
ことを特徴とする光電変換素子。
- 前記式(1)に示したシアニン化合物は、式(3)で表される化合物である
ことを特徴とする請求項1記載の光電変換素子。
- 前記式(3)に示した化合物は、式(4)で表される化合物である
ことを特徴とする請求項2記載の光電変換素子。
- 前記式(4)に示した化合物は、式(5)で表される化合物である
ことを特徴とする請求項3記載の光電変換素子。
- 前記R7、R8、R10およびR11のうちの少なくとも1つは、前記式(2)に示した基である
ことを特徴とする請求項1ないし請求項4のいずれか1項に記載の光電変換素子。 - 前記アンカー基は、−CH2 −CH2 −C(=O)−OHで表される基あるいは−CH2 −CH2 −C(=O)−O- で表される基である
ことを特徴とする請求項1ないし請求項5のいずれか1項に記載の光電変換素子。 - 前記Y1およびY2の双方がアンカー基である
ことを特徴とする請求項1ないし請求項6のいずれか1項に記載の光電変換素子。 - 前記Qは、メチン鎖にシアノ基が導入された連結基である
ことを特徴とする請求項1ないし請求項7のいずれか1項に記載の光電変換素子。 - 前記担持体は、酸化亜鉛(ZnO)を含む
ことを特徴とする請求項1ないし請求項8のいずれか1項に記載の光電変換素子。 - 式(1)で表されるシアニン構造を有する
ことを特徴とする光電変換素子用色素。
- 前記式(1)に示したシアニン構造は、式(3)で表される構造である
ことを特徴とする請求項10記載の光電変換素子用色素。
- 前記式(3)に示した構造は、式(4)で表される構造である
ことを特徴とする請求項11記載の光電変換素子用色素。
- 前記式(4)に示した構造は、式(5)で表される構造である
ことを特徴とする請求項12記載の光電変換素子用色素。
- 前記R7、R8、R10およびR11のうちの少なくとも1つは、前記式(2)に示した基である
ことを特徴とする請求項10ないし請求項13のいずれか1項に記載の光電変換素子用色素。 - 前記アンカー基は、−CH2 −CH2 −C(=O)−OHで表される基あるいは−CH2 −CH2 −C(=O)−O- で表される基である
ことを特徴とする請求項10ないし請求項14のいずれか1項に記載の光電変換素子用色素。 - 前記Y1およびY2の双方がアンカー基である
ことを特徴とする請求項10ないし請求項15のいずれか1項に記載の光電変換素子用色素。 - 前記Qは、メチン鎖にシアノ基が導入された連結基である
ことを特徴とする請求項10ないし請求項16のいずれか1項に記載の光電変換素子用色素。
Priority Applications (5)
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JP2008333597A JP5250412B2 (ja) | 2008-12-26 | 2008-12-26 | 光電変換素子用色素および光電変換素子 |
PCT/JP2009/071547 WO2010074203A1 (ja) | 2008-12-26 | 2009-12-25 | 光電変換素子用色素および光電変換素子 |
CN200980152843.0A CN102265454B (zh) | 2008-12-26 | 2009-12-25 | 光电转换元件用色素及光电转换元件 |
US13/141,993 US8912344B2 (en) | 2008-12-26 | 2009-12-25 | Dye for photoelectric conversion device and photoelectric conversion device |
EP09834999.6A EP2372829B1 (en) | 2008-12-26 | 2009-12-25 | Pigment for use with photoelectric conversion element, and photoelectric conversion element |
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JP2008333597A JP5250412B2 (ja) | 2008-12-26 | 2008-12-26 | 光電変換素子用色素および光電変換素子 |
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JP5250412B2 JP5250412B2 (ja) | 2013-07-31 |
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US (1) | US8912344B2 (ja) |
EP (1) | EP2372829B1 (ja) |
JP (1) | JP5250412B2 (ja) |
CN (1) | CN102265454B (ja) |
WO (1) | WO2010074203A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012060346A1 (ja) * | 2010-11-01 | 2012-05-10 | パナソニック株式会社 | 光電気素子、光電気素子の製造方法、及び光増感剤 |
WO2015029771A1 (ja) | 2013-08-29 | 2015-03-05 | 株式会社Adeka | 色素増感型太陽電池 |
JPWO2014103831A1 (ja) * | 2012-12-28 | 2017-01-12 | 株式会社Adeka | 担持体及び光電変換素子 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8884029B2 (en) * | 2008-09-30 | 2014-11-11 | Adeka Corporation | Dye for photoelectric conversion device and photoelectric conversion device |
JP5583990B2 (ja) * | 2010-02-26 | 2014-09-03 | 株式会社Adeka | 光電変換素子及び光電変換素子用色素 |
EP2621599A1 (en) * | 2010-09-27 | 2013-08-07 | The Technical University of Denmark | Improved electron transport layer |
US20130180577A1 (en) * | 2012-01-18 | 2013-07-18 | Semiconductor Energy Laboratory Co., Ltd. | Photoelectric conversion device |
KR20140138749A (ko) * | 2012-03-30 | 2014-12-04 | 가부시키가이샤 아데카 | 색소증감 태양전지 및 색소증감 태양전지의 제조방법 |
KR102345977B1 (ko) * | 2014-08-26 | 2021-12-30 | 삼성전자주식회사 | 유기 광전 소자 및 이미지 센서 |
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JP2008277268A (ja) * | 2007-03-30 | 2008-11-13 | Tdk Corp | 光電変換素子 |
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JP2000294303A (ja) * | 1999-04-02 | 2000-10-20 | Fuji Photo Film Co Ltd | 光電変換素子および光電気化学電池 |
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- 2009-12-25 WO PCT/JP2009/071547 patent/WO2010074203A1/ja active Application Filing
- 2009-12-25 CN CN200980152843.0A patent/CN102265454B/zh not_active Expired - Fee Related
- 2009-12-25 EP EP09834999.6A patent/EP2372829B1/en not_active Not-in-force
- 2009-12-25 US US13/141,993 patent/US8912344B2/en not_active Expired - Fee Related
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WO2012060346A1 (ja) * | 2010-11-01 | 2012-05-10 | パナソニック株式会社 | 光電気素子、光電気素子の製造方法、及び光増感剤 |
US9236576B2 (en) | 2010-11-01 | 2016-01-12 | Panasonic Corporation | Photoelectric element, process for producing photoelectric element, and photosensitizer |
JPWO2014103831A1 (ja) * | 2012-12-28 | 2017-01-12 | 株式会社Adeka | 担持体及び光電変換素子 |
WO2015029771A1 (ja) | 2013-08-29 | 2015-03-05 | 株式会社Adeka | 色素増感型太陽電池 |
CN105340037A (zh) * | 2013-08-29 | 2016-02-17 | 株式会社艾迪科 | 色素敏化型太阳能电池 |
JPWO2015029771A1 (ja) * | 2013-08-29 | 2017-03-02 | 株式会社Adeka | 色素増感型太陽電池 |
US9881745B2 (en) | 2013-08-29 | 2018-01-30 | Adeka Corporation | Dye sensitized solar cell |
Also Published As
Publication number | Publication date |
---|---|
US8912344B2 (en) | 2014-12-16 |
US20110253218A1 (en) | 2011-10-20 |
EP2372829A4 (en) | 2012-08-08 |
WO2010074203A1 (ja) | 2010-07-01 |
JP5250412B2 (ja) | 2013-07-31 |
CN102265454A (zh) | 2011-11-30 |
CN102265454B (zh) | 2014-04-30 |
EP2372829B1 (en) | 2015-08-19 |
EP2372829A1 (en) | 2011-10-05 |
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