JPWO2012117730A1 - 重合体および光電変換素子 - Google Patents
重合体および光電変換素子 Download PDFInfo
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- JPWO2012117730A1 JPWO2012117730A1 JP2013502196A JP2013502196A JPWO2012117730A1 JP WO2012117730 A1 JPWO2012117730 A1 JP WO2012117730A1 JP 2013502196 A JP2013502196 A JP 2013502196A JP 2013502196 A JP2013502196 A JP 2013502196A JP WO2012117730 A1 JPWO2012117730 A1 JP WO2012117730A1
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- polymer
- photoelectric conversion
- organic semiconductor
- type organic
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- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
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- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000414 polyfuran Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000001955 polymer synthesis method Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HLLICFJUWSZHRJ-UHFFFAOYSA-N tioxidazole Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)SC2=C1 HLLICFJUWSZHRJ-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
図1は、実施の形態に係る光電変換素子10の構成を示す概略断面図である。本実施の形態の光電変換素子10は有機半導体を含む光電変換層を有する有機薄膜太陽電池である。
[素子構造] ITO透明電極/PEDOT:PSS膜/光電変換層/Ca/Al
ITO透明電極として市販のITOガラス(面抵抗20Ω/sq以下)を用いた。ITO透明電極の上に、市販のPEDOT:PSS(商品名 Starck AI 4083)をスピン塗布により製膜した後、120〜150℃で加熱し乾燥させて膜厚約40nmのPEDOT:PSS膜を形成した。重量比1:1で[60]PCBMとp型有機半導体をクロロベンゼン溶媒に加えて所定濃度の塗布液を作成し、この塗布液をPEDOT:PSS膜の上にスピン塗布した。この後、所定の温度で乾燥させて膜厚約120nmの光電変換層を形成した。p型有機半導体としての重合体の詳細については後述する。得られた光電変換層の上に、真空蒸着法により膜厚が約10nmになるようにCaを成膜した後、さらに、真空蒸着法により膜厚が約100nmになるようにAlを成膜した。
比較例1のp型有機半導体(ドナー)は、市販のポリ(3−ヘキシルチオフェン)(P3HT)(Rieke Metal製)であり、数平均分子量はポリスチレン換算で16500、多分散度は1.8である。また、P3HTのクロロベンゼン1mLに対しての溶解度は20mgである。また、SCLC法で評価した正孔移動度は3.1×10−4cm2/Vsである。なお、有機薄膜太陽電池素子作成時の塗布液の濃度は2.0質量%、乾燥温度は約110℃である。
比較例1〜4で用いた各重合体の合成方法について以下に説明する。比較例1で用いたp型有機半導体は、市販のポリ(3−ヘキシルチオフェン)(P3HT)(Rieke Metal製)であり、数平均分子量はポリスチレン換算で16500、多分散度は1.8である。比較例2は非特許文献1を参考にし、合成した。比較例3および比較例4は非特許文献2を参考にし、合成した。
<3-(2-ヘキシルデシル)チオフェンの合成>
まず、下記反応式に従って3-(2-ヘキシルデシル)チオフェン(A1)を合成した。
1H-NMR(400MHZ,CDCl3,TMS) δ 7.23 (dd, J=4.9Hz, 1.0Hz, 1H), 6.93 (d, J=4.9Hz, 1H), 6.92 (d, J=1.0Hz, 1H), 2.55 (d, J=6.8Hz, 2H), 1.25 (m, 25H), 0.88 (m, 6H)
続いて、下記反応式に従って2-ブロモ-3-(2-ヘキシルデシル)チオフェン(A2)を合成した。
1H-NMR(400MHZ,CDCl3,TMS) δ 7.17 (d, J=5.4Hz, 1H), 6.75 (d, J=5.4Hz, 1H), 2.49 (d, J=7.0Hz, 2H), 1.25 (m, 25H), 0.88 (m, 6H)
続いて、下記反応式に従って3-(2-ヘキシルデシル)-2チオフェンアルデヒド(A3)を合成した。
1H-NMR(400MHZ,CDCl3,TMS) δ 10.03 (s, 1H) 7.64 (d, J=4.9Hz, 1H), 6.97 (d, J=4.9Hz, 1H), 2.88 (d, J=7.3Hz, 2H), 1.25 (m, 25H), 0.88 (m, 6H)
続いて、下記反応式に従って2,5-ビス(3(2-ヘキシルデシル)チオフェン-2−イル)チアゾロ[5,4-d]チアゾール(A4)を合成した。
1H-NMR(400MHZ,CDCl3,TMS) δ 7.34 (d, J=5.4Hz, 1H), 6.95 (d, J=5.4Hz, 1H), 2.93 (d, J=7.4Hz, 2H), 1.25 (m, 25H), 0.88 (m, 6H)
続いて、下記反応式に従って2,5-ビス(5-ブロモ-3(2-ヘキシルデシル)チオフェン-2−イル)チアゾロ[5,4-d]チアゾール(A5)を合成した。
1H-NMR(400MHZ,CDCl3,TMS) δ 6.90 (d, J=5.4Hz, 1H), 2.84 (d, J=7.5Hz, 2H), 1.25 (m, 25H), 0.88 (m, 6H)
1H-NMR(400MHZ,CDCl3,TMS) δ 7.24 (dd, J=4.9Hz, 1.0Hz, 1H), 6.93 (d, J=4.9Hz, 1H), 6.92 (d, J=1.0Hz, 1H), 2.62 (t, J=7.7Hz, 2H), 1.25 (m, 24H), 0.88 (m, 3H)
1H-NMR(400MHZ,CDCl3,TMS) δ 7.18 (d, J=5.6Hz, 1H), 6.79 (d, J=5.6Hz, 1H), 2.56 (t, J=7.7Hz, 2H), 1.25 (m, 24H), 0.88 (m, 3H)
1H-NMR(400MHZ,CDCl3,TMS) δ 10.04 (s, 1H), 7.64 (d, J=4.9Hz, 1H), 7.00 (d, J=4.9Hz, 1H), 2.96 (t, J=7.7Hz, 2H), 1.25 (m, 24H), 0.88 (m, 3H)
1H-NMR (400MHZ, CDCl3, TMS) δ 7.38 (d, J=5.1 Hz, 1H), 6.99 (d, J=5.1 Hz, 1H), 2.97 (t, J=7.8 Hz, 2H), 1.25 (m, 25 H), 0.88 (m, 6 H)
1H-NMR(400MHZ,CDCl3,TMS) δ 6.95 (d, J=5.4Hz, 1H), 2.88 (d, J=7.5Hz, 2H), 1.25 (m, 25H), 0.88 (m, 6H)
1H-NMR(400MHZ,CDCl3,TMS) δ 7.03 (d, J=5.4Hz, 1H), 2.96 (d, J=7.5Hz, 2H), 1.25 (m, 25H), 0.88 (m, 6H), 0.40 (s, 9H)
出発原料として1−ブロモデカンを用いる以外は、原料モノマーA11と同様の手順で合成した。
出発原料として、1-ブロモ-2-ブチルオクタンを用いる以外は、原料モノマーA5と同様の手順で合成した。
出発原料としてA13を用いる以外は、A10からA11の合成と同様の手順で合成した。
出発原料として1-ブロモ-2-エチルヘキサンを用いる以外は、原料モノマーA11と同様の手順で合成した。
以下の手順に従い合成した。
(1)3-メトキシチオフェンの合成
窒素雰囲気下、ディーンスタークをつけたフラスコにエタノール(60 ml)を加え、その後氷浴でナトリウム(6.9 g, 300 mmol)と加え30分撹拌した。その後。NMP(50 ml)を加え反応溶液を110℃で加熱し、メタノールを取り除いた後3-ブロモチオフェン(32.6 g, 200 mmol)と臭化銅(2.9 g, 20 mmol)を加え110℃で45分撹拌した。反応溶液を室温まで冷却し、反応溶液に水を加え、ペンタンで抽出し、有機層を飽和食塩水、水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、濾過後溶液を減圧下で留去した。得られた反応混合物を減圧蒸留することで、目的物を透明なオイルで得た(収率65%)。
1H-NMR(400MHZ,CDCl3,TMS) δ 7.18 (dd, J=4.8Hz,2.8Hz 1H), 6.75 (dd, J=4.8Hz,1.9Hz, 1H),6.25 (d, J=1.9Hz, 1H), 3.81 (s, 3H)
(2)3-(2-ブチルオクトキシ)チオフェンの合成
窒素雰囲気下、3-メトキシチオフェン(5.0 g, 44.8 mmol)、2-ブチルオクタノール(16.7 g, 89.6 mmol)、p-トルエンスルホン酸(850 mg, 4.48 mmol)をトルエン(40 ml)に溶解させ、15時間還流を行った。その後反応溶液に水を加え、塩化メチレンで抽出し、有機層を飽和食塩水、水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、濾過後溶液を減圧下で留去した。得られた反応溶液を、ヘキサンを移動層とするシリカゲルカラムクロマトグラフィーで分離精製することで目的物を透明なオイルで得た(収率83%)。
1H-NMR(400MHZ,CDCl3,TMS) δ 7.17 (dd, J=5.2Hz,1.6Hz 1H), 6.76 (d, J=5.2Hz, 1H),6.21 (d, J=1.6Hz, 1H), 3.81 (d, J=5.8Hz, 2H), 1.25 (m, 17H), 0.88 (m, 6H)
(3)2-ホルミル-3-(2-ブチルオクトキシ)チオフェンの合成
窒素雰囲気下、0℃でオキシ塩化リン(3.5 ml 40 mmol)をゆっくりDMF(70 ml)に滴下し、10分撹拌する。その後、3-(2-ブチルオクトキシ)チオフェン(9 g, 30.4 mmol)のDMF(15 ml)溶液を反応溶液にゆっくり滴下する。その後反応溶液を70℃で2時間加熱する。その後、室温まで冷却し、水浴で冷却しながら10%水酸化ナトリウム水溶液をゆっくり加え、30分撹拌する。その後反応溶液をクロロホルムで抽出し、有機層を飽和食塩水、水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、濾過後溶液を減圧下で留去した。得られた反応混合物をヘキサンと酢酸エチルの混合溶媒を移動層とするシリカゲルカラムクロマトグラフィーで分離精製することで目的物を透明なオイルで得た(収率80%)。
1H-NMR(400MHZ,CDCl3,TMS) δ 10.00 (s, 1H), 7.67 (d, J=4.8Hz, 1H), 6.84 (d, J=4.8Hz, 1H), 4.03 (d, J=4.8Hz, 2H), 1.25 (m, 17H), 0.88 (m, 6H)
(4)2,5-ビス(3-(2-ブチルオクトキシ)チオフェン-2-イル)チアゾロ[5,4-d]チアゾールの合成
窒素雰囲気下、2-ホルミル-3-(2-ブチルオクトキシ)チオフェン(7 g, 23.6 mmol)、ルベアン酸(1.42 g, 11.8 mmol)をディーンスタークを取り付けたフラスコに加え、200℃に加熱し、5時間攪拌した。その後、反応混合物をクロロホルムで抽出し、有機層を飽和食塩水、水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、濾過後溶媒を減圧下で留去した。得られた反応混合物をヘキサンとクロロホルムの混合溶媒を移動層とするシリカゲルカラムクロマトグラフィーで分離精製することで目的物を黄色固体で得た(収率29%)。
1H-NMR(400MHZ,CDCl3,TMS) δ 7.31 (d, J=5.6Hz, 1H), 6.88 (d, J=5.6Hz, 1H), 4.13 (d, J=4.8Hz, 2H), 1.25 (m, 17H), 0.88 (m, 6H)
(5)2,5-ビス(5-ブロモ-3-(2-ブチルオクトキシ)チオフェン-2-イル)チアゾロ[5,4-d]チアゾールの合成
窒素雰囲気下、2,5-ビス(3-(2-ブチルオクトキシ)チオフェン-2-イル)チアゾロ[5,4-d]チアゾール(2.3 g, 3.4 mmol)、NBS(1.33 g, 7.4 mmol)、クロロホルム(80 ml)、酢酸(40 ml)をフラスコに加え、3時間0℃で撹拌した。その後反応溶液に飽和炭酸水素ナトリウム水溶液を加え、クロロホルムで抽出し、有機層を飽和食塩水、水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、濾過後溶媒を減圧下で留去した。得られた反応混合物をヘキサンとクロロホルムの混合溶媒を移動層とするシリカゲルカラムクロマトグラフィーで分離精製、その後ヘキサンで再結晶することで目的物を黄色固体で得た(収率85%)。
1H-NMR(400MHZ,CDCl3,TMS) δ 6.90 (s,1H), 4.09 (d, J=4.8Hz, 2H), 1.25 (m, 17H), 0.88 (m, 6H)
(6)2,5-ビス(3-(2-ブチルオクトキシ)-5-トリメチルスタニル)チオフェン-2−イル)チアゾロ[5,4-d]チアゾール(A16)の合成
窒素雰囲気下、2,5-ビス(5-ブロモ-3-(2-ブチルオクトキシ)チオフェン-2-イル)チアゾロ[5,4-d]チアゾール(416 mg 0.5 mmol)、THF (20 ml)を加え、-78℃まで冷却した。その後、n-BuLi (1.25 mmol, 0.78 ml, 1.60M)を滴下し、1時間、同温で攪拌し、Me3SnCl (300 mg, 1.5 mmol)を加え室温まで昇温しさらに1時間攪拌した。その後、反応溶液に水を加え、クロロホルムで抽出し、有機層を飽和食塩水、水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、濾過後溶媒を減圧下で留去した。得られた混合物を、ヘキサンで2回再結晶(冷蔵庫等低温で)することで目的物(A16)を黄色固体で得た(収率60%)。
1H-NMR(400MHZ,CDCl3,TMS) δ 6.92 (s,1H), 4.16 (d, J=4.8Hz, 2H), 1.25 (m, 17H), 0.88 (m, 6H), 0.41 (s,9H)
原料モノマーA16の合成で、2−ブチルオクタノールの代わりに、2−ヘキシルデカノールを用いる以外は、同様の手順で合成した。
以下の手順に従い合成した。
(1)5-ブロモ-3-チオフェンカルボン酸の合成
窒素雰囲気下、3-チオフェンカルボン酸( 10 g, 78 mmol)を酢酸(100 ml)に加え、その後臭素( 12.5 g, 78 mmol)ゆっくり滴下し、1時間、同温で攪拌しその後氷(300 g)を加え、析出してきた白色固体を濾過、水で洗浄後、乾燥することで、目的物を白色固体で得た(収率80%)。
1H-NMR(400MHZ,CDCl3,TMS) δ 8.12 (s, 1H), 7.51 (s, 1H)
(1)5-ブロモ-2-ホルミル-3-チオフェンカルボン酸の合成
窒素雰囲気下、5-ブロモ-3-チオフェンカルボン酸( 12 g, 58 mmol)をTHF(300 ml)に加え、LDA(174 mmol, 232 ml, 0.75M)を-78℃でゆっくり滴下した。その後、-30℃で2時間撹拌し、DMFを-78℃でゆっくり滴下した。その後、反応溶液に水を加え、酢酸エチルで抽出し、有機層を飽和食塩水、水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、濾過後溶媒を減圧下で留去することで目的物を固体で得た(収率95%、粗製生物)。
1H-NMR(400MHZ,CDCl3,TMS) δ 10.44 (s, 1H), 7.63 (s, 1H)
(3)2-ヘキシルデシル 5-ブロモ-2-ホルミル-3-チオフェンカルボキシレート
窒素雰囲気下、5-ブロモ-2-ホルミル-3-チオフェンカルボン酸( 12 g, 51 mmol)をDMF(200 ml)に加え、その後炭酸ナトリウム(27 g, 255 mmol)を加えた。その後、120℃で10時間加熱し、その後、室温まで冷却し、反応溶液に水を加え、酢酸エチルで抽出し、有機層を飽和食塩水、水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、濾過後溶媒を減圧下で留去した。得られた混合物を、ヘキサンとクロロホルムの混合溶媒を移動層とするシリカゲルカラムクロマトグラフィーで分離精製することで目的物を透明なオイルで得た(収率55%)。
1H-NMR(400MHZ,CDCl3,TMS) δ 10.50 (s, 1H), 7.52 (s, 1H), 4.26 (d, J=5.9Hz, 2H), 1.25 (m, 25H), 0.88 (m, 6H)
(4)ビス(2-ヘキシルデシル) 2,2’-(チアゾロ[5,4-d]チアゾール)ビス(5-ブロモチオフェン-3-カルボキシレート)(A17)の合成
窒素雰囲気下、2-ヘキシルデシル 5-ブロモ-2-ホルミル-3-チオフェンカルボキシレート(6 g, 13 mmol)、ルベアン酸(780 mg, 6.5 mmol)をDMF(100 ml)に加え、140℃に加熱し、TLCで原料が消費されるのを確認しながら、8時間攪拌した。その後、反応混合物をクロロホルムで抽出し、有機層を飽和食塩水、水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、濾過後溶媒を減圧下で留去した。得られた反応混合物をヘキサンとクロロホルムの混合溶媒を移動層とするシリカゲルカラムクロマトグラフィーで分離精製し、その後ヘキサンで再結晶することで目的物(A18)を黄色固体で得た(収率9%)。
1H-NMR(400MHZ,CDCl3,TMS) δ 7.45 (s,1H), 4.26 (d, J=4.8Hz, 2H), 1.25 (m, 25H), 0.88 (m, 6H)
実施例1で用いられる重合体P3を下記反応式に従って合成した。
実施例2で用いられる重合体P3は実施例1で用いられた重合体P3と同様にして合成した。用いた原料モノマーは実施例1と同様に原料モノマーA5とA11であるが、実施例2の重合体P3の数平均分子量は重合体P3と異なる。
比較例4で用いられる重合体P3は実施例1で用いられた重合体P3と同様にして合成した。用いた原料モノマーは実施例1と同様に原料モノマーA5とA11であるが、比較例4の重合体P3の数平均分子量は重合体P3と異なる。
実施例3で用いられる重合体P4は、原料モノマーA11の代わりに、原料モノマーA12を用いる以外は、実施例1で用いられる重合体P3と同様に合成した。
実施例4で用いられる重合体P5は、原料モノマーA11の代わりに、原料モノマーA14を用いる以外は、実施例1で用いられる重合体P3と同様に合成した。
実施例5で用いられる重合体P6は、原料モノマーA11の代わりに、原料モノマーA15を用いる以外は、実施例1で用いられる重合体P3と同様に合成した。
実施例6で用いられる重合体P7は、原料モノマーA5の代わりに原料モノマーA13、原料モノマーA11の代わりに、原料モノマーA14を用いる以外は、実施例1で用いられる重合体P3と同様に合成した。
実施例7で用いられる重合体P8は、原料モノマーA5の代わりに原料モノマーA17、原料モノマーA11の代わりに、原料モノマーA16を用い、溶媒としてクロロベンゼンの代わりにトルエンを用いる以外は、実施例1で用いられる重合体P3と同様に合成した。
実施例8で用いられる重合体P9は、原料モノマーA17の代わりに原料モノマーA18を用いる以外は、実施例7で用いられる重合体P8と同様に合成した。
PCE(%)=Jsc(mA/cm2)×Voc(V)×FF
AM 1.5G条件で得られた結果を表1に示す。
Claims (6)
- 下記式(1)で表されるチアゾロチアゾール骨格とヘテロ原子を含む5員環を含む繰り返し単位からなる重合体であり、SCLC法で測定した正孔移動度が7.5×10−5cm2/Vs以上であり、クロロベンゼン1mLに対しての溶解度が10mg以上であることを特徴とする重合体。
- 前記式(1)中、R1、R2、R3、R4の中、直鎖アルキル基の比率が50%を超えず、数平均分子量がポリスチレン換算で15000以上である請求項1記載の重合体。
- 前記式(1)中、R1およびR2が分岐アルキル基であり、R3、R4が直鎖アルキル基である請求項1または2に記載の重合体。
- 前記重合体の光吸収末端の波長が650nm以上である請求項1乃至3のいずれか1項に記載の重合体。
- 前記重合体の最高占有分子軌道(HOMO)が5.1eVより深いことである請求項1乃至4のいずれか1項に記載の重合体。
- p型有機半導体と、前記p型有機半導体とバルクヘテロ接合を形成するn型有機半導体とを有する光電変換層と、前記光電変換層の受光面側において前記光電変換層と電気的に接続されている第1の電極と、前記光電変換層の受光面とは反対側において前記光電変換層と電気的に接続されている第2の電極とを備え、前記p型有機半導体が請求項1記載の重合体であることを特徴とする光電変換素子。
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