JP5691628B2 - 光起電力素子用材料および光起電力素子 - Google Patents
光起電力素子用材料および光起電力素子 Download PDFInfo
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- JP5691628B2 JP5691628B2 JP2011038024A JP2011038024A JP5691628B2 JP 5691628 B2 JP5691628 B2 JP 5691628B2 JP 2011038024 A JP2011038024 A JP 2011038024A JP 2011038024 A JP2011038024 A JP 2011038024A JP 5691628 B2 JP5691628 B2 JP 5691628B2
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- 239000000463 material Substances 0.000 title claims description 47
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 6
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 3
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Images
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Photovoltaic Devices (AREA)
Description
ITO:インジウム錫酸化物
PEDOT:ポリエチレンジオキシチオフェン
PSS:ポリスチレンスルホネート
PC70BM:フェニル C71 ブチリックアシッドメチルエステル
Eg:バンドギャップ
HOMO:最高被占分子軌道
Isc:短絡電流密度
Voc:開放電圧
FF:フィルファクター
η:光電変換効率
なお、1H−NMR測定にはFT−NMR装置((株)日本電子製JEOL JNM−EX270)を用いた。また、平均分子量(数平均分子量、重量平均分子量)はGPC装置(クロロホルムを送液したTOSOH社製、高速GPC装置HLC−8220GPC)を用い、絶対検量線法によって算出した。重合度nは以下の式で算出した。
重合度n=[(重量平均分子量)/(繰り返しユニットの分子量)]
また、光吸収端波長は、ガラス上に約60nmの厚さに形成した薄膜について、日立製作所(株)製のU−3010型分光光度計を用いて測定した薄膜の紫外可視吸収スペクトル(測定波長範囲:300〜900nm)から得た。バンドギャップ(Eg)は下式により、光吸収端波長から算出した。なお、薄膜はクロロホルムを溶媒に用いてスピンコート法により形成した。
Eg(eV)=1240/薄膜の光吸収端波長(nm)
また、最高被占分子軌道(HOMO)準位は、ITOガラス上に約60nmの厚さに形成した薄膜について、表面分析装置(大気中紫外線光電子分光装置AC−1型、理研機器(株)製)を用いて測定した。なお、薄膜はクロロホルムを溶媒に用いてスピンコート法により形成した。
化合物A−1を式1に示す方法で合成した。合成例1記載中の化合物(1−d)はマクロモレキュルズ(Macromolecules)2007年、40巻、1981−1986頁に記載されている方法を参考にして合成した。
1H−NMR(270MHz,CDCl3):7.91(s,2H),7.65(m,4H),7.38(m,6H)ppm。
化合物A−2を式2に示す方法で合成した。
1H−NMR(270MHz,CDCl3):8.15(s,2H),7.88(d,J=4.1Hz,2H),7.76−7.73(m,4H),7.52(d,J=4.9Hz,2H),7.40−7.36(m,6H),7.20−7.17(m,2H)ppm。
1H−NMR(270MHz,CDCl3):8.07(s,2H),7.71−7.68(m,4H),7.57(d,J=4.1Hz,2H),7.44−7.37(m,6H),7.12(d,J=4.1Hz,2H)ppm。
化合物A−3を式3に示す方法で合成した。合成例3記載中の化合物(3−a)はマクロモレキュルズ(Macromolecules)2007年、40巻、1981−1986頁に記載されている方法を参考にして合成した。
1H−NMR(270MHz,CDCl3):8.08(s,2H)、7.84(s,2H)、7.75(m,4H)、7.41(m,6H)、7.15(d,J=4.9Hz,2H)、6.95(d,J=4.9Hz,2H)、1.95(m,8H)、1.02−0.95(m,60H)ppm。
1H−NMR(270MHz,CDCl3):8.10(s,2H)、7.77(s,2H)、7.73−7.54(m,4H)、7.44−7.42(m,6H)、6.98(s,2H)、2.0−1.8(m,8H)、1.02−0.59(m,60H)ppm。
化合物A−4を式4に示す方法で合成した。
1H−NMR(270MHz,CDCl3):9.48(d,J=8.6H,2H)、8.58(d,J=8.6H,2H)、8.04(s,2H)、7.88−7.77(m,4H)ppm。
1H−NMR(270MHz,CDCl3):9.47(d,J=7.8H,2H)、8.56(d,J=7.8H,2H)、8.18(s,2H)、7.76(m,4H)、1.57(s,24H)ppm。
化合物A−5を式5に示す方法で合成した。
1H−NMR(270MHz,CDCl3):9.36(d,J=8.0Hz,2H)、8.12(d,J=8.0Hz,2H)、8.02(d,J=8.0Hz,2H)、7.95(d,J=8.0Hz,2H)、7.56(t,J=8.0Hz,2H)、7.64(t,J=8.0Hz,2H)、7.48(t,J=8.0Hz,2H)ppm。
13C−NMR(67.5MHz,CDCl3):196.72,135.67,134.95,134.00,131.05,129.29,128.83,128.60,126.98,125.94,124.38ppm。
1H−NMR(270MHz,CDCl3):8.06(d,J=8.0Hz,2H)、8.03(s,2H)、7.76(d,J=8.0Hz,2H)、7.71(d,J=8.0Hz,2H)、7.42(t,J=8.0Hz,2H)、7.34(t,J=8.0Hz,2H)、7.25(d,J=8.0Hz,2H)、7.15(t,J=8.0Hz,2H)ppm。
化合物A−6を式6に示す方法で合成した。合成例6記載中の化合物(6−c)ジャーナルオブザアメリカンケミカルソサエティ(Journal of the American Chemical Society)2006年、128巻、10992−10993頁に記載されている方法を参考にして合成した。
1H−NMR(270MHz,CDCl3):7.95(d,J=8.1Hz,2H)、7.71(d,J=8.1Hz,2H)、7.38−7.32(m,2H)、7.22−7.13(m,4H)、6.95−6.85(m,4H)、6.92(s,2H)ppm。
1H−NMR(270MHz,CDCl3):7.82(d,J=7.6Hz,4H)、7.42−7.16(m,8H)、7.03(d,J=7.6Hz,2H)、6.58(d,J=7.6Hz,2H)ppm。
1H−NMR(270MHz,CDCl3):8.52(d,J=7.6Hz,2H)、8.02(s,2H)、7.74(d,J=7.6Hz,2H)、7.46(t,J=7.6Hz,2H)、7.34(t,7.6Hz,2H)、7.23−7.18(m,4H),7.07(t,J=7.6Hz,2H)、6.76(d,J=7.6Hz,2H)ppm。
化合物B−1を式7に示す方法で合成した。
1H−NMR(270MHz,CDCl3):7.99(s,2H),7.53(d,J=4.1Hz,2H),7.11(d,J=4.1Hz)、2.83(s,6H)ppm。
化合物B−2を式8に示す方法で合成した。合成例8記載中の化合物(8−a)は上記非特許文献4に記載されている方法を参考にして合成した。
化合物B−3を式9に示す方法で合成した。合成例9記載中の化合物(9−a)は上記非特許文献4に記載されている方法を参考にして合成した。
上記A−1(1mg)とPC70BM(4mg、Solenne社製)をクロロベンゼン0.25mlの入ったサンプル瓶の中に加え、超音波洗浄機((株)井内盛栄堂製US−2(商品名)、出力120W)中で30分間超音波照射することにより溶液Aを得た。
フィルファクター=IVmax(mA・V/cm2)/(短絡電流密度(mA/cm2)×開放電圧(V))
(ここで、IVmaxは、印加電圧が0Vから開放電圧値の間で電流密度と印加電圧の積が最大となる点における電流密度と印加電圧の積の値である。)
光電変換効率=[(短絡電流密度(mA/cm2)×開放電圧(V)×フィルファクター)/擬似太陽光強度(100mW/cm2)]×100(%)
以下の実施例と比較例におけるフィルファクターと光電変換効率も全て上式により算出した。
A−1の代わりに上記A−2を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流−電圧特性を測定した。この時の短絡電流密度は9.12mA/cm2、開放電圧は0.61V、フィルファクター(FF)は0.50であり、これらの値から算出した光電変換効率は2.78%であった。
A−1の代わりに上記A−3を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流−電圧特性を測定した。この時の短絡電流密度は7.72mA/cm2、開放電圧は0.64V、フィルファクター(FF)は0.42であり、これらの値から算出した光電変換効率は2.08%であった。
A−1の代わりに上記A−4を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流−電圧特性を測定した。この時の短絡電流密度は8.36mA/cm2、開放電圧は0.58V、フィルファクター(FF)は0.49であり、これらの値から算出した光電変換効率は2.37%であった。
実施例5
A−1の代わりに上記A−5を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流−電圧特性を測定した。この時の短絡電流密度は7.61mA/cm2、開放電圧は0.60V、フィルファクター(FF)は0.56であり、これらの値から算出した光電変換効率は2.56%であった。
実施例6
A−1の代わりに上記A−6を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流−電圧特性を測定した。この時の短絡電流密度は7.25mA/cm2、開放電圧は0.62V、フィルファクター(FF)は0.48であり、これらの値から算出した光電変換効率は2.16%であった。
A−1の代わりに上記B−1を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流−電圧特性を測定した。この時の短絡電流密度は4.34mA/cm2、開放電圧は0.61V、フィルファクター(FF)は0.54であり、これらの値から算出した光電変換効率は1.43%であった。
A−1の代わりに上記B−2を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流−電圧特性を測定した。この時の短絡電流密度は4.81mA/cm2、開放電圧は0.60V、フィルファクター(FF)は0.41であり、これらの値から算出した光電変換効率は1.18%であった。
A−1の代わりに上記B−3を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流−電圧特性を測定した。この時の短絡電流密度は3.20mA/cm2、開放電圧は0.62V、フィルファクター(FF)は0.49であり、これらの値から算出した光電変換効率は0.97%であった。
2:正極
3:有機半導体層
4:負極
5:電子供与性有機材料を有する層
6:電子受容性有機材料を有する層
Claims (5)
- 一般式(1)で表される構造を有する電子供与性有機材料を含むことを特徴とする光起電力素子用材料。
- さらに電子受容性有機材料を含む請求項1記載の光起電力素子用材料。
- 前記電子受容性有機材料がフラーレン化合物である請求項2記載の光起電力素子用材料。
- 前記フラーレン化合物がC70誘導体である請求項3記載の光起電力素子用材料。
- 少なくとも正極と負極を有する光起電力素子であって、負極と正極の間に請求項1〜4のいずれか記載の光起電力素子用材料を含む光起電力素子。
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