JP2013199590A - 電子供与性有機材料、それを用いた光起電力素子用材料および光起電力素子 - Google Patents
電子供与性有機材料、それを用いた光起電力素子用材料および光起電力素子 Download PDFInfo
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- JP2013199590A JP2013199590A JP2012068892A JP2012068892A JP2013199590A JP 2013199590 A JP2013199590 A JP 2013199590A JP 2012068892 A JP2012068892 A JP 2012068892A JP 2012068892 A JP2012068892 A JP 2012068892A JP 2013199590 A JP2013199590 A JP 2013199590A
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- 239000011368 organic material Substances 0.000 title claims abstract description 107
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- 125000003118 aryl group Chemical group 0.000 claims description 16
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
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- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 6
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 5
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- 125000001624 naphthyl group Chemical group 0.000 description 1
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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
Landscapes
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Photovoltaic Devices (AREA)
Abstract
【解決手段】特定の構造を有する電子供与性有機材料を含む光起電力素子用材料、およびこれを用いた光起電力素子。
【選択図】なし
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。
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。
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−2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。なお、合成例1記載の化合物(1−e)はマクロモレキュルズ(Macromolecules)、2010年、43巻、8051−8057頁に記載されている方法を参考に、化合物(1−g)はアドバンスドマテリアルズ(Advanced Materials)、2011年、23巻、1409−1413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):3.44(d,J=5.2Hz,2H),1.57」(m,1H),1.4−1.2(m,32H),0.88(t,J=6.2Hz,6H)ppm。
1H−NMR(270MHz,CDCl3):9.97(s,J=1H),7.5−7.4(m,3H),7.14(m,1H),3.89(d,J=5.7Hz,2H),1.78(m,1H),1.5−1.2(m,32H),0.88(t,J=6.2Hz,6H)ppm。
1H−NMR(270MHz,CDCl3):7.53(s,2H),7.40(m,4H),7.19(d,J=7.8Hz,2H),3.88(d,J=5.7Hz,4H),1.78(m,2H),1.4−1.2(m,64H),0.88(t,J=6.2Hz,6H)ppm。
1H−NMR(270MHz,CDCl3):7.92(s,2H),7.2(m,6H),6.92(m,2H),3.69(d,J=5.9Hz,4H),1.56(m,2H),1.4−1.2(m,64H),0.87(t,J=6.5Hz,6H)ppm。
上記化合物(1−f)155mg(0.15mmol)および化合物(1−g)94mg(0.15mmol)をトルエン(和光純薬工業(株)製)10mlに溶解させたところに、トリス(ジベンジリデンアセトン)ジパラジウム(東京化成工業(株)製)4mg、トリス(2−メチルフェニル)ホスフィン(東京化成工業(株)製)を7mg加え、窒素雰囲気下、100℃で12時間撹拌した。次いで、ブロモベンゼン(東京化成工業(株)製)10mgを加え、100℃にて1時間撹拌した。次いで、2−(tributylstannyl)thiophene(アルドリッチ社製)40mgを加え、100℃にてさらに1時間撹拌した。撹拌終了後、反応混合物を室温まで冷却し、メタノール100mlに注いだ。析出した固体をろ取し、メタノール、水、アセトンの順に洗浄し、次いでソックスレー抽出器を用いてメタノール、アセトン、ヘキサンの順で洗浄した。得られた固体をクロロベンゼンに溶解させた後、メタノールに再沈殿し、化合物A−1(126mg)を得た。重量平均分子量は11,500、数平均分子量は7,200、重合度nは9.8であった。また、光吸収端波長は695nm、バンドギャップ(Eg)は1.57eV、最高被占分子軌道(HOMO)準位は−5.05eVであった。
化合物A−2を式2に示す方法で合成した。なお、合成例2記載の化合物(2−g)はアドバンスドファンクショナルマテリアルズ(Advanced Functional Materials)、2011、21巻、718−728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):9.97(s,1H),7.4(m,3H),7.15(m,1H),4.01(t,J=6.5Hz,2H),1.78(m,2H),1.4−1.2(m,10H),0.89(t,J=6.8Hz,3H)ppm。
1H−NMR(270MHz,CDCl3):7.51(s,2H),7.45(d,J=7.6Hz,2H),7.38(t,J=7.6Hz,2H),7.19(d,J=7.6Hz,2H),4.01(t,J=6.5Hz,4H),1.80(m,4H),1.6−1.3(m,24H),0.87(t,J=7.0Hz,6H)ppm。
1H−NMR(270MHz,CDCl3):7.91(s,2H),7.26−7.15(m,6H),6.93(m,2H),3.85(t,J=6.8Hz,4H),1.73(m,4H),1.41−1.24(m,24H),0.89(t,J=7.0Hz,6H)ppm。
1H−NMR(270MHz,CDCl3):8.16(s,2H),7.89(d,J=3.8Hz,2H),7.51(d,J=4.9Hz,2H),7.39(s,2H),7.25−7.20(m,6H),6.94(m,2H),3.91(t,J=6.5Hz,4H),1.75(m,4H),1.5−1.3(m,20H),0.90(t,J=6.6Hz,6H)ppm。
1H−NMR(270MHz,CDCl3):8.12(s,2H),8.01(d,J=3.5Hz,2H),7.38−7.21(m,8H),6.92(m,2H),3.87(t,J=6.5Hz,4H),1.73(m,4H),1.6−1.3(m,20H),0.89(t,J=7.0Hz,6H),0.43(s,18H)ppm。
化合物A−3を式3に示す方法で合成した。なお、合成例3記載の化合物(3−a)はアドバンスドファンクショナルマテリアルズ(Advanced Functional Materials)、2011、21巻、718−728頁に記載されている方法を参考にして合成した。
化合物A−4を式4に示す方法で合成した。なお、合成例4記載の化合物(4−a)は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)」、2009年、131巻、7792頁に記載の方法を参考にして合成した。
化合物B−1を式5に示す方法で合成した。なお、合成例5記載の化合物(5−a)および(5−b)は非特許文献8に記載の方法を参考にして合成した。
合成例6
化合物B−2を式6に示す方法で合成した。なお、合成例6記載の化合物(6−a)および(6−b)は非特許文献10に記載の方法を参考にして合成した。
実施例1
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9.60mA/cm2、開放電圧は0.86V、フィルファクター(FF)は0.59であり、これらの値から算出した光電変換効率は4.87%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6.31mA/cm2、開放電圧は0.88V、フィルファクター(FF)は0.60であり、これらの値から算出した光電変換効率は3.33%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8.91mA/cm2、開放電圧は0.51V、フィルファクター(FF)は0.60であり、これらの値から算出した光電変換効率は2.73%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2.65mA/cm2、開放電圧は0.68V、フィルファクター(FF)は0.53であり、これらの値から算出した光電変換効率は0.96%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ことを特徴とする電子供与性有機材料。
- 請求項1に記載の電子供与性有機材料と電子受容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。
- 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2〜4のいずれか記載の光起電力素子用材料を含むことを特徴とする光起電力素子。
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