JP5442625B2 - 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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- JP5442625B2 JP5442625B2 JP2010531801A JP2010531801A JP5442625B2 JP 5442625 B2 JP5442625 B2 JP 5442625B2 JP 2010531801 A JP2010531801 A JP 2010531801A JP 2010531801 A JP2010531801 A JP 2010531801A JP 5442625 B2 JP5442625 B2 JP 5442625B2
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- 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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- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- 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
Images
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
- C07D421/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
- C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
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Description
上記実施の形態で説明した色素の具体例として、上記した化学式(I)および化学反応式(III )に従って、化学式(4)に示した化合物である化学式(7)に示した化合物を合成した。
化学式(8)に示した化合物を合成した。この際、まず、化学反応式(I−2)に示したように、化学式(162−1)に示した化合物に代えて、化学式(162−2)で表される化合物を用いたことを除き、実施例1−1と同様にして、化学式(164−2)で表されるインドレニウム塩を得た。次に、この化学式(164−2)に示したインドレニウム塩を、化学式(164−1)に示したインドレニウム塩に代えて用いたことを除き、実施例1−1と同様にして最終生成物を得た。この場合の収率は50%であった。
化学式(9)に示した化合物を合成した。この際、まず、化学反応式(I−3)に示したように、化学式(162−1)に示した化合物に代えて、化学式(162−3)で表される化合物を用いると共に、化学式(163−1)に示した化合物に代えて化学式(163−2)で表される化合物を用いたことを除き、実施例1−1と同様にして、化学式(164−3)で表されるインドレニウム塩を得た。次に、この化学式(164−3)に示したインドレニウム塩を、化学式(164−1)に示したインドレニウム塩に代えて用いたことを除き、実施例1−1と同様にして最終生成物を得た。この場合の収率は2.3%であった。
化学式(35)に示した化合物を合成した。この際、まず、化学反応式(I−4)に示したように、化学式(162−3)に示した化合物に代えて、化学式(164−4)で表される化合物を用いたことを除き、実施例1−3と同様にして化学式(162−4)で表される塩(4級アンモニウム塩)を得た。次に、この化学式(164−4)に示した化合物を、化学式(164−3)に示したインドレニウム塩に代えて用いたことを除き、実施例1−3と同様にして最終生成物を得た。この場合の収率は6.3%であった。
化学式(47)に示した化合物を合成した。この際、まず、化学反応式(I−5)に示したように、化学式(164−5A)で表されるインドレニン化合物と、化学式(164−5B)で表される化合物と、酢酸と、水とを混合することにより、化学式(164−5C)で表されるインドレニウム塩を得た。次に、この化学式(164−5C)に示したインドレニウム塩を、化学反応式(III −1)において化学式(164−1)に示したインドレニウム塩に代えて用いたことを除き、実施例1−1と同様にして最終生成物を得た。この場合の収率は8.7%であった。
化学式(158)に示した化合物を合成した。この際、まず、化学反応式(I−6)に示したように、化学式(162−1)に示した化合物に代えて、化学式(162−6)で表される化合物を用いたことを除き、実施例1−1と同様にして化学式(164−6)で表される塩を得た。
化学式(159)に示した化合物を合成した。この際、まず、化学反応式(I−7)に示したように、化学式(162−3)に示した化合物に代えて、化学式(162−6)で表される化合物を用いたことを除き、実施例1−3と同様にして化学式(164−6)で表される塩を得た。続いて、実施例1−5と同様に化学反応式(III −2A),化学反応式(III −2B)に示したように化学式(174B)に示した中間体を得た。最後に、化学式(164−6)に示した塩を、化学反応式(III −2C)における化学式(164−5)に示した塩に代えて用いたことを除き、実施例1−5と同様にして最終生成物を得た。この場合の収率は、25%であった。
化学式(160)に示した化合物を合成した。この際、まず、実施例1−3と同様に化学反応式(I−3)に示したように化学式(164−3)に示したインドレニウム塩を得た。続いて、実施例1−5と同様に化学反応式(III −2A),化学反応式(III −2B)に示したように化学式(174B)に示した中間体を得た。最後に、化学式(164−3)に示したインドレニウム塩を、化学反応式(III −2C)における化学式(164−5)に示した塩に代えて用いたことを除き、実施例1−5と同様にして最終生成物を得た。この場合の収率は、1.1%であった。
化学式(161)に示した化合物を合成した。この際、まず、化学反応式(I−8)に示したように、化学式(162−3)に示した化合物に代えて、化学式(162−7)で表される化合物を用いたことを除き、実施例1−3と同様にして化学式(164−7)で表されるインドレニウム塩を得た。続いて、実施例1−5と同様に化学反応式(III −2A),化学反応式(III −2B)に示したように化学式(174B)に示した中間体を得た。最後に、化学式(164−7)に示したインドレニウム塩を、化学反応式(III −2C)における化学式(164−5)に示した塩に代えて用いたことを除き、実施例1−5と同様にして最終生成物を得た。この場合の収率は、22%であった。
実施例1−1で合成した化学式(7)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、化学式(7)に示した化合物に代えて、以下の化学式(175)に示した色素(比較例1−1)あるいは化学式(176)に示した色素(比較例1−2)を用いたことを除き、実施例2と同様の手順を経た。
色素として化学式(7)に示した化合物に代えて、表3に示したように実施例1−2〜1−9で合成した化学式(8),化学式(9),化学式(35),化学式(47),化学式(158)〜化学式(161)に示した化合物を用いたことを除き、実施例2と同様にして色素増感型太陽電池を作製した。
色素として化学式(7)に示した化合物に代えて、表3に示したように下記の化学式(177)〜化学式(183)に示した色素を用いたことを除き、実施例2と同様にして色素増感型太陽電池を作製した。
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、実施例2,3−1〜3−8と同様の手順を経た。この場合には、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整した電解浴液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。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。
実施例4−1〜4−9と同様に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、比較例1−1,2−3〜2−7と同様の手順を経た。
焼結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、実施例2,3−1〜3−8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、以下のように調整した。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、分散させて金属酸化物スラリーを調整した。
実施例5−1〜5−9と同様に焼結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、比較例1−1,2−3〜2−7と同様の手順を経た。
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た光電変換素子であって、
前記色素は、化学式(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。
- 前記化学式(1)に示したシアニン化合物は、化学式(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。
- 前記化学式(3)に示したR9およびR10のうちの少なくとも1つは、炭素原子数6以上25以下のアルキル基である
ことを特徴とする請求項2記載の光電変換素子。 - 前記化学式(3)に示した化合物は、化学式(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。
- 前記化学式(4)に示した環Aおよび環Bは、いずれもメトキシ基を有するベンゼン環である
ことを特徴とする請求項4記載の光電変換素子。 - 前記化学式(4)に示したR9、R10、R12およびR13のうちの少なくとも1つは、炭素原子数6以上25以下のアルキル基である
ことを特徴とする請求項4または請求項5に記載の光電変換素子。 - 前記化学式(4)に示したR9、R10、R12およびR13は、いずれも炭素原子数6以上25以下のアルキル基である
ことを特徴とする請求項4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7のいずれか1項に記載の光電変換素子。 - 前記担持体は、電解析出法により形成されると共に酸化亜鉛(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。 - 化学式(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。
- 前記化学式(1)に示したシアニン構造は、化学式(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。
- 前記化学式(3)に示したR9およびR10のうちの少なくとも1つは、炭素原子数6以上25以下のアルキル基である
ことを特徴とする請求項11記載の光電変換素子用色素。 - 前記化学式(3)に示した構造は、化学式(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。
- 前記化学式(4)に示した環Aおよび環Bは、いずれもメトキシ基を有するベンゼン環である
ことを特徴とする請求項13記載の光電変換素子用色素。 - 前記化学式(4)に示したR9、R10、R12およびR13のうちの少なくとも1つは、炭素原子数6以上25以下のアルキル基である
ことを特徴とする請求項13または請求項14に記載の光電変換素子用色素。 - 前記化学式(4)に示したR9、R10、R12およびR13は、いずれも炭素原子数6以上25以下のアルキル基である
ことを特徴とする請求項13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16のいずれか1項に記載の光電変換素子用色素。
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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 |
KR101549320B1 (ko) * | 2011-03-10 | 2015-09-01 | 고꾸리츠 다이가꾸호오징 기후다이가꾸 | 헵타메틴 구조를 가지는 화합물, 증감 색소 및 광전변환 소자 |
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- 2009-09-09 WO PCT/JP2009/065713 patent/WO2010038589A1/ja active Application Filing
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- 2009-09-09 KR KR1020107027963A patent/KR101236035B1/ko active IP Right Grant
- 2009-09-09 CN CN200980139355.6A patent/CN102187513B/zh active Active
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JP2007220412A (ja) * | 2006-02-15 | 2007-08-30 | Gifu Univ | 色素増感型光電変換素子に用いられる増感色素と該増感色素が用いられた色素増感型太陽電池 |
JP2008101064A (ja) * | 2006-10-17 | 2008-05-01 | Tdk Corp | 色素、電極および光電変換素子 |
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US20110155249A1 (en) | 2011-06-30 |
CN102187513A (zh) | 2011-09-14 |
KR20110008324A (ko) | 2011-01-26 |
JPWO2010038589A1 (ja) | 2012-03-01 |
US9424999B2 (en) | 2016-08-23 |
CN102187513B (zh) | 2014-04-02 |
EP2330680A1 (en) | 2011-06-08 |
WO2010038589A1 (ja) | 2010-04-08 |
US20150027542A1 (en) | 2015-01-29 |
EP2330680A4 (en) | 2012-08-08 |
EP2330680B1 (en) | 2013-10-23 |
KR101236035B1 (ko) | 2013-02-21 |
US8884029B2 (en) | 2014-11-11 |
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