JP5791995B2 - 新規化合物、光電変換材料及び光電変換素子 - Google Patents
新規化合物、光電変換材料及び光電変換素子 Download PDFInfo
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- JP5791995B2 JP5791995B2 JP2011169522A JP2011169522A JP5791995B2 JP 5791995 B2 JP5791995 B2 JP 5791995B2 JP 2011169522 A JP2011169522 A JP 2011169522A JP 2011169522 A JP2011169522 A JP 2011169522A JP 5791995 B2 JP5791995 B2 JP 5791995B2
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- photoelectric conversion
- organic semiconductor
- type organic
- conversion element
- semiconductor material
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Images
Classifications
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- 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
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- Photovoltaic Devices (AREA)
Description
しかし、有機系太陽電池の光電変換効率は低いものが多いため、高光電変換効率化が課題となっている。
また本発明の別の目的は、上記新規化合物を用いた光電変換材料、光電変換層、光電変換素子及び有機薄膜太陽電池を提供することにある。
本発明の新規化合物は、上記一般式(1)で表わされる。
上記一般式(1)におけるA1が表す1価の芳香族基としては、置換されてもよい炭素原子数6〜20の芳香族炭化水素環基又は置換されてもよい炭素原子数3〜20の芳香族ヘテロ環基が挙げられる。
上記芳香族炭化水素環基としては、無置換芳香族炭化水素環基又は脂肪族炭化水素基で置換された芳香族炭化水素環基(但し、脂肪族炭化水素基を含めた炭素原子数が6〜20であるもの)が挙げられ、上記芳香族ヘテロ環基としては、無置換芳香族ヘテロ環基又は脂肪族炭化水素基で置換された芳香族ヘテロ環基(但し、脂肪族炭化水素基を含めた炭素原子数が3〜20であるもの)が挙げられる。
上記炭素原子数1〜5の脂肪族炭化水素基は、−O−、−COO−、−OCO−、−CO−、−S−、−SO−、−SO2−、−NR−又は−C=C−で中断されていてもよく、Rは炭素原子数1〜5の脂肪族炭化水素基を表し、その例としては、上記芳香族炭化水素環基を置換してもよい炭素原子数1〜5の脂肪族炭化水素基の説明で例示した基が挙げられ、該炭素原子数1〜5の脂肪族炭化水素基を中断する基に炭素原子を含む場合、中断される基を含めた炭素原子数が1〜5である。
即ち、反応式(ア)において、ビスアルキン体(11)と2当量のハロゲン化アリール(12)との薗頭−萩原クロスカップリングにて、中間体(2)が得られる。
また、ビスアルキン体(11)と当量のハロゲン化アリール(12)との同様の反応にて、中間体(13)にした後に、ジハロゲン化アリール(14)と2当量の中間体(13)を反応させることで、中間体(3)が得られる。
また、中間体(13)と当量のジハロゲン化アリール(14)とを反応させ、中間体(15)にした後に、ビスアルキン体(11)と2当量の中間体(15)を反応させることで中間体(4)が得られる。以下、中間体(2)〜(4)をまとめて、下記一般式(5)で表わす(以下、中間体(5)ともいう)。尚、中間体(5)は、n=0のとき、中間体(2)を表し、n=1のとき、中間体(3)を表し、n=2のとき、中間体(4)を表す。
次に反応式(イ)において、Cp2ZrCl2を2当量のn−BuLiにより還元し、そこへ中間体(5)を反応させることにより、ジルコナシクロペンタジエン誘導体(6)を得ることが出来る。
続いて反応式(ウ)において、ジルコナシクロペンタジエン誘導体(6)と塩化硫黄(S2Cl2)とを反応させることで、本発明の上記一般式(1)で表される新規化合物が得ることが出来る。
本発明の光電変換材料は、(A)本発明の上記一般式(1)で表わされる化合物を、(B)p型有機半導体材料及び(C)n型有機半導体材料に含有させたものである。
(A)上記一般式(1)で表される化合物:好ましくは0.5〜5重量%、更に好ましくは1〜3重量%
(B)p型有機半導体材料:好ましくは25〜70重量%、更に好ましくは35〜60重量%
(C)n型有機半導体材料::好ましくは25〜70重量%、更に好ましくは35〜60重量%
次に、本発明の光電変換層について説明する。本発明の光電変換層は、本発明の光電変換材料を製膜して得られる。製膜方法に関しては特に限定するものではないが、例えば、蒸着法、物理気相成長法(PVD)、化学気相成長法(CVD)、原子層堆積法(ALD)、原子層エピタキシー法(ALE)、分子線エピタキシー法(MBE)、気相エピタキシー法(VPE)、スパッタ法、プラズマ重合法等のドライプロセス;ディップコート法、キャスト法、エアーナイフコート法、カーテンコート法、ローラーコート法、ワイヤーバーコート法、グラビアコート法、スピンコート法、LB法、オフセット印刷法、スクリーン印刷法、フレキソ印刷法、ディスペンサ印刷法、インクジェット法、エクストルージョンコート法等のウェットプロセスによって支持体上に塗膜形成する方法が挙げられる。
本発明の光電変換素子は、本発明の光電変換層を少なくとも一つ有する以外は、従来公知の光電変換素子と同様に構成される。例えば、図1(a)を例にとって示すと、支持体1、電極2、電荷移動層3、光電変換層4、及び電極5が順次積層された構造を有する。また、図1(b)に示すように電荷移動層3を除いた構造であってもよく、図1(c)に示すように電荷移動層6を更に有する構造であってもよい。
<ステップ1>1,7−ビス(2,2’−ビチオフェン)−4,4−ビス(ブトキシメチル)−1,6−ヘプタジイン(下記〔化9〕に示される中間体1)の製造
4,4−ビス(ブトキシメチル)−1,6−ヘプタジイン(3.36g、12.7mmol)、2−ブロモ−5−(2’−チエニル)チオフェン(7.47g、30.5mmol)、Pd(PPh3)4(352mg、0.305mmol)、CuI(116mg、0.61mmol)及びトリエチルアミン(10ml)を、テトラヒドロフラン(30ml)中で混合し、45℃にて攪拌させながら12時間反応させた。得られた反応溶液を、シリカゲルカラムクロマトグラフ法(ヘキサン:酢酸エチル=25:1の移動相溶媒)で精製することにより、無色透明液体(6.3g、単離収率83%)を得た。目的物であることは、1H−NMR、13C−NMR、及び高分解能質量分析スペクトル(HRMS)にて確認した。
1H−NMR(400MHz、CDCl3):δ=7.21(dd、J=1.2,5.5Hz、2H)、7.15(dd、J=0.8,3.6Hz、2H)、6.99−7.03(m、6H)、3.45−3.49(m、8H)、2.65(s、4H)、1.52−1.62(m、4H)、1.35−1.46(m、4H)、0.94(t、J=7.5Hz、6H)
13C−NMR(100MHz、CDCl3):δ=137.6、136.9、131.9、127.8、124.7、123.9、123.2、122.8、92.3、75.6、71.8、71.3、43.1、31.7、23.7、19.4、13.9
HRMS(EI):592.1598(計算値);592.1589(測定値)
Cp2ZrCl2(729mg、2.5mmol)のテトラヒドロフラン溶液を−78℃に冷却し、n−BuLi(1.62M/ヘキサン溶液、5.0mmol)を滴下し、同温のまま1時間反応させた。次に、ステップ1で得られた中間体1(1.25mg、2.1mmol)のテトラヒドロフラン溶液を混合し、30〜35℃にて5時間反応させた。その後、塩化硫黄(338mg、2.5mmol)を加え反応させた。得られた反応溶液を、シリカゲルカラムクロマトグラフ法(ヘキサン:クロロホルム=1:1の移動相溶媒)で精製することにより橙色粉体(948mg、単離収率72%)を得た。目的物であることは、1H−NMR、13C−NMR、及び高分解能質量分析スペクトル(HRMS)にて確認した。
1H−NMR(400MHz、CDCl3):δ=7.22(dd、J=0.8,5.1Hz、2H)、7.17(dd、J=1.2,3.6Hz、2H)、7.09(d、J=4.0Hz、2H)、7.02(dd、J=3.6,5.1Hz、2H)、6.99(d、J=3.6Hz、2H)、3.42−3.49(m、8H)、2.78(s、4H)、1.52−1.59(m、4H)、1.33−1.43(m、4H)、0.92(t、J=7.1Hz、6H)
13C−NMR(100MHz、CDCl3):δ=144.1、137.2、136.1、136.0、127.9、125.0、124.3、124.2、123.9、123.5、73.9、71.2、55.4、34.5、31.6、19.3、13.9
HRMS(EI):624.1318(計算値);624.1301(測定値)
<ステップ1>1−(2,2’−ビチオフェン)−4,4−ビス(ブトキシメチル)−1,6−ヘプタジイン(下記〔化10〕に示される中間体2)の製造
4,4−ビス(ブトキシメチル)−1,6−ヘプタジイン(3.36g、12.7mmol)、2−ブロモ−5−(2’−チエニル)チオフェン(3.11g、12.7mmol)、Pd(PPh3)4(147mg、0.127mmol)、CuI(48mg、0.254mmol)及びトリエチルアミン(5ml)を、テトラヒドロフラン(40ml)中で混合し、室温にて攪拌させながら12時間反応させた。得られた反応溶液を、シリカゲルカラムクロマトグラフ法(ヘキサン:酢酸エチル=25:1の移動相溶媒)で精製することにより、無色透明液体(3.7g、単離収率68%)を得た。目的物であることは、1H−NMR、13C−NMR、及び高分解能質量分析スペクトル(HRMS)にて確認した。
1H−NMR(400MHz、CDCl3):δ=7.21(dd、J=0.8,5.1Hz、1H)、7.15(dd、J=0.8,3.9Hz、1H)、6.99−7.03(m、3H)、3.42−3.47(m、8H)、2.62(s、2H)、2.42(d、J=2.8Hz、1H)、2.00(t、J=2.8Hz、1H)、1.52−1.58(m、4H)、1.36−1.43(m、4H)、0.93(t、J=7.5Hz、6H)
13C−NMR(100MHz、CDCl3):δ=137.5、136.9、131.8、127.8、124.7、123.9、123.2、122.8、92.3、81.1、77.2、75.5、71.5、71.2、70.3、42.4、31.7、23.3、22.2、19.3
HRMS(EI):428.1843(計算値);428.1843(測定値)
ステップ1で得られた中間体2(1.89g、4.4mmol)、5,5’−ジブロモ−(2,2’−ビチオフェン)(583mg、1.8mmol)、Pd(PPh3)4(42mg、0.036mmol)、CuI(14mg、0.072mmol)及びトリエチルアミン(1.7ml)をテトラヒドロフラン(10ml)中で混合し、45℃にて攪拌させながら12時間反応させた。得られた反応溶液を、シリカゲルカラムクロマトグラフ法(ヘキサン:酢酸エチル=15:1の移動相溶媒)で精製することにより淡黄色液体(1.56g、単離収率85%)を得た。目的物であることは、1H−NMR、13C−NMR、及び高分解能質量分析スペクトル(HRMS)にて確認した。
1H−NMR(400MHz、CDCl3):δ=7.22(dd、J=0.8,4.8Hz、2H)、7.16(dd、J=0.8,3.6Hz、2H)、7.00−7.05(m、8H)、6.97−6.99(dd、J=0.8,3.6Hz、2H)、3.46−3.51(m、16H)、2.68(s、8H)、1.55−1.62(m、8H)、1.39−1.47(m、8H)、0.96(dt、J=7.2,7.6Hz、12H)
13C−NMR(100MHz、CDCl3):δ=137.6、136.9、136.8、131.9、131.8、127.8、124.6、123.9、123.4、123.2、123.1、122.7、92.7、92.3、75.63、75.56、71.8、71.3、43.0、31.7、23.7、19.4、13.9
HRMS(EI):1018.3285(計算値);1018.3280(測定値)
Cp2ZrCl2(371mg、1.27mmol)のテトラヒドロフラン溶液を−78℃に冷却し、n−BuLi(1.62M/ヘキサン溶液、2.54mmol)を滴下し、同温のまま1時間反応させた。次に、ステップ2で得られた中間体3(507mg、0.49mmol)のテトラヒドロフラン溶液を混合し、30〜35℃にて5時間反応させた。その後、塩化硫黄(199mg、1.47mmol)を加え反応させた。得られた反応溶液を、シリカゲルカラムクロマトグラフ法(ヘキサン:クロロホルム=1:2の移動相溶媒)で精製することにより赤色粉体(248mg、単離収率46%)を得た。目的物であることは、1H−NMR、13C−NMR、及び高分解能質量分析スペクトル(HRMS)にて確認した。
1H−NMR(400MHz、CDCl3):δ=7.22(dd、J=0.8,5.1Hz、2H)、7.17(dd、J=1.2,3.6Hz、2H)、7.08(d、J=4.0Hz、4H)、7.02(dd、J=3.6,5.1Hz、2H)、7.00(d、J=4.0Hz、4H)、3.42−3.49(m、16H)、2.78(s、8H)、1.52−1.59(m、8H)、1.33−1.43(m、8H)、0.92(t、J=7.1Hz、12H)
13C−NMR(100MHz、CDCl3):δ=144.2、144.1、137.2、136.1、136.05、136.03、135.9、127.9、125.09、125.06、124.3、124.2、124.0、124.0、123.98、123.91、123.5、73.9、71.2、55.4、34.5、31.6、19.3、13.9
HRMS(EI):1082.2726(計算値);1082.2738(測定値)
図1(c)に示す層構成を有する光電変換素子を、以下の手順で作製した。
電極2としてITOが150nm成膜してあるガラス基板(支持体1)をIPA煮沸洗浄及びUV−オゾン洗浄した後、電極2上に、PEDOT:PSS(3,4−エチレンジオキシチオフェン:ポリスチレンスルホン酸)を20nmスピンコート法により成膜し、100℃、10分の条件で減圧乾燥して、電荷移動層3とした。これとは別に、1,2−ジクロロベンゼン2mLに(A)上記一般式(1)で表される化合物として化合物No.1を5mg、(B)p型有機半導体としてP3HTを50mg、及び(C)n型有機半導体としてPCBMを50mg溶解させて、実施例1の光電変換材料を調製した。電荷移動層3上に、調製した光電変換材料を、スピンコート法により成膜し、100℃、30分の条件で減圧乾燥して光電変換層4とした。こうして得られた有機薄膜層である光電変換層4上に、メタルマスクを用いてLiF0.5nm(電荷移動層6)、及びアルミニウム100nm(電極5)を逐次真空蒸着成膜して、実施例1の光電変換素子を作製した。
こうして得られた光電変換素子に対し、エアマス1.5G、100mW/cm2の擬似太陽光をITO電極側から照射して光電変換特性(効率(%))を測定した。結果を[表1]に示す。
上記実施例1の光電変換素子の作製において、(A)〜(C)成分及び組成比を〔表1〕に示すように変更する以外は、実施例1と同様にして、実施例2の光電変換素子を作製した。また、実施例1と同様の操作で、実施例2の光電変換素子の光電変換特性(効率(%))を測定した。結果を[表1]に示す。
上記実施例1の光電変換素子の作製において、(A)成分を用いない以外は実施例1と同様の操作で、比較例1の光電変換素子を作製し、実施例1と同様の操作で、比較例1の光電変換素子の光電変換特性(効率(%))を測定した。結果を[表1]に示す。
従って、上記一般式(1)で表わされる、本発明の新規化合物を添加した光電変換材料は、光電変換素子に有用である。
2 電極
3 電荷移動層
4 光電変換層
5 電極
6 電荷移動層
Claims (6)
- 上記(B)p型有機半導体材料がポリ(3−ヘキシルチオフェン)であり、上記(C)n型有機半導体材料がフラーレン誘導体である請求項2に記載の光電変換材料。
- 請求項2又は3に記載の光電変換材料を製膜して得られる光電変換層。
- 請求項4に記載の光電変換層を有してなる光電変換素子。
- 請求項5に記載の光電変換素子を有してなる有機薄膜太陽電池。
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