JPWO2010024090A1 - 光電気素子 - Google Patents
光電気素子 Download PDFInfo
- Publication number
- JPWO2010024090A1 JPWO2010024090A1 JP2010526633A JP2010526633A JPWO2010024090A1 JP WO2010024090 A1 JPWO2010024090 A1 JP WO2010024090A1 JP 2010526633 A JP2010526633 A JP 2010526633A JP 2010526633 A JP2010526633 A JP 2010526633A JP WO2010024090 A1 JPWO2010024090 A1 JP WO2010024090A1
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- Prior art keywords
- transport layer
- electron transport
- redox
- organic compound
- chemical formula
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 claims abstract description 67
- 239000008151 electrolyte solution Substances 0.000 claims abstract description 34
- 230000005525 hole transport Effects 0.000 claims abstract description 31
- -1 radical compound Chemical class 0.000 claims description 70
- 150000003949 imides Chemical class 0.000 claims description 9
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 7
- 150000004059 quinone derivatives Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 75
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 3
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- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
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- 238000006138 lithiation reaction Methods 0.000 description 1
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- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- CZNGTXVOZOWWKM-UHFFFAOYSA-N methyl 4-bromobenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1 CZNGTXVOZOWWKM-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 description 1
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
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- 239000001103 potassium chloride Substances 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 125000001339 silanediyl group Chemical group [H][Si]([H])(*)* 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
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- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
- PEQHIRFAKIASBK-UHFFFAOYSA-N tetraphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PEQHIRFAKIASBK-UHFFFAOYSA-N 0.000 description 1
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- 230000002463 transducing effect Effects 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical group N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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- 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
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- H01G9/2009—Solid electrolytes
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Abstract
Description
ゲル乾燥体とは、ゲルを乾燥させたもの指す。この、ゲルを乾燥させるとは、ゲルに内包される溶液の除去、特には溶媒の除去を指す。またゲルを乾燥させる方法としては、加熱、真空環境中での溶液または溶媒の除去、他の溶媒でのゲルに内包される溶液または溶媒の除去などが挙げられる。
(Xi)n及び(Xi)njはゲル部位を示し、Xiはゲル部位を形成する化合物のモノマーを示すものであり、ポリマー骨格で形成することができる。モノマーの重合度nは、n=1〜10万の範囲が好ましい。YはXに結合している酸化還元部を示すものである。またj,kはそれぞれ1分子中に含まれる(Xi)n、Yの数を表す任意の整数であり、いずれも1〜10万の範囲が好ましい。酸化還元部Yはゲル部位(Xi)n及び(Xi)njをなすポリマー骨格のあらゆる部位に結合していてもよい。また酸化還元部Yは種類の異なる材料を含んでいてもよく、この場合は電子交換反応の観点から酸化還元電位が近い材料が好ましい。
[化25]に示す反応の手順で、既述の[化7]のガルビ(Galvi)化合物を合成した。
まず、4−ブロモ−2,6−ジ−tert−ブチルフェノール(135.8g;0.476mol)にアセトニトリル(270ml)を加え、さらに不活性雰囲気下、N,O−ビス(トリメチルシリル)アセトアミド(BSA)(106.3g;129.6ml)を加え、70℃で終夜撹拌し、完全に結晶が析出するまで反応した。そして析出した白色結晶を濾過し、真空乾燥した後、エタノールで再結晶して精製することによって、[化25]において符号「1」で示す、(4−ブロモ−2,6−ジ−tert−ブチルフェノキシ)トリメチルシラン(150.0g;0.420mol)を白色板状結晶として得た。
上記ガルビモノマーの合成で得られたガルビモノマー(p−ヒドロガルビノキシルスチレン)1gと、テトラエチレングリコールジアクリレート57.7mgと、アゾビスイソブチロニトリル15.1mgを、テトラヒドロフラン2mlに溶解した後、窒素置換し、一晩還流することで、ガルビモノマーを重合させ、[化25]において符号「4」で示すガルビポリマーを得た。このガルビポリマーの数平均分子量は10000であった。
[化27]に示す反応で、既述の[化4]のキノンポリマーを合成した。
まず、アルゴン雰囲気下、30mlのナスフラスコに、4−4’−オキシジフタル酸無水物310.20mg(0.001mol)、N−N−ジメチルアセトアミド2ml、1.4−フェニレンジアミン108.15mg(0.001mol)を加え、室温下で18時間反応させた。反応終了後、アセトンに沈殿させて精製することによって、白色固体として[化28]に示す重合体411.8mgを得た。
20mlのナスフラスコに、4,4′−ビピリジン(1.008g;6.46×10-3mol)と1,10−ジブロモデカン(1.938g、6.46×10-3mol)を投入し、CH3OH−DMF(=50:50vol%)(10ml)中で攪拌し、完全に溶解させた。この攪拌を60℃で54時間継続すると、淡黄色沈殿が析出し始めた。さらに12時間攪拌するとほぼ溶媒がなくなり、溶媒を含んだ淡黄色沈殿が析出した。この淡黄色沈殿をアセトニトリルとクロロホルムで洗浄した後、グラスフィルターを用いてろ過し、加熱減圧乾燥により溶媒を除去することによって、淡黄色粉末としてポリデシルビオロゲン(PV10)(1.95g、Yield:65%)を得た。尚、化学構造をNMRにより測定したところ、重合度は10、分子量はおよそ3200であり、PV10であると同定することができた。
実施例4と同様にしてビオロゲン誘導体からなる電子輸送層3を形成し、さらに実施例4と同様にして電子輸送層3に亜鉛錯体色素を付着させた
そして電極1の周囲に付いた電子輸送層3の材料を削り取り、電子輸送層3を囲むように、熱溶融性接着剤(三井デュポンポリケミカル製「バイネル」)の封止材を配置した。次に、ダイヤモンドドリルで中央付近に孔をあけたこの電極1にPt対極6を対向させて張り合わせ、水に2,2,6,6−テトラメチルピペリジン−1−オキシル(TEMPO)を0.1mol/l、塩化カリウムを1.6mol/lそれぞれ溶解して調製した電解液を上記の孔から注入し、紫外線硬化樹脂で孔を封止することによって、色素増感性光電変換素子を得た(図2参照)。
厚み1mmのガラス基板1aの表面にフッ素ドープSnO2の透明導電性酸化物層2で電極1を形成したものを用いた(旭硝子(株)製、10Ω/□)。
2 透明導電性酸化物の層
3 電子輸送層
4 正孔輸送層
5 電極
6 対極
7 ゲル層
Claims (9)
- 一対の電極間に電子輸送層と正孔輸送層を挟んで形成される光電気素子であって、電子輸送層は、繰り返し酸化還元が可能な酸化還元部を有する有機化合物を備えて形成され、有機化合物は酸化還元部の還元状態を安定化させる電解質溶液を含んでゲル層として形成されていることを特徴とする光電気素子。
- 上記有機化合物の酸化還元部は、フェノキシル誘導体で形成されていることを特徴とする請求項1に記載の光電気素子。
- 上記有機化合物の酸化還元部は、キノン誘導体で形成されていることを特徴とする請求項1に記載の光電気素子。
- 上記有機化合物の酸化還元部は、イミド誘導体で形成されていることを特徴とする請求項1に記載の光電気素子。
- 上記有機化合物の酸化還元部は、ビオロゲン誘導体で形成されていることを特徴とする請求項1に記載の光電気素子。
- 上記有機化合物は、数平均分子量が1000以上であることを特徴とする請求項1乃至5のいずれか1項に記載の光電気素子。
- 上記電子輸送層の厚みは100nm以上であることを特徴とする請求項1乃至6のいずれか1項に記載の光電気素子。
- 上記正孔輸送層に安定ラジカル化合物が含まれていることを特徴とする請求項1乃至7のいずれか1項に記載の光電気素子。
- 色素を上記電子輸送層に接して、電子輸送層と正孔輸送層の界面に設けて、色素増感型太陽電池として形成したことを特徴とする請求項1乃至8のいずれか1項に記載の光電気素子。
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JP5654779B2 (ja) * | 2009-06-19 | 2015-01-14 | パナソニック株式会社 | 光電気素子 |
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JP2013020990A (ja) * | 2009-11-02 | 2013-01-31 | Murata Mfg Co Ltd | 光電変換素子および光電変換装置 |
US20130008510A1 (en) * | 2010-03-24 | 2013-01-10 | Nec Corporation | Photoelectric conversion element, photosensor, and solar cell |
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TWI453926B (zh) * | 2010-09-09 | 2014-09-21 | Chi Lin Technology Co Ltd | 太陽能電池及其電極層結構 |
JP5894372B2 (ja) * | 2010-11-01 | 2016-03-30 | パナソニック株式会社 | 光電気素子、及び光電気素子の製造方法 |
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