JP7200381B2 - 非対称構造を有する有機高分子およびその光電材料としての使用 - Google Patents
非対称構造を有する有機高分子およびその光電材料としての使用 Download PDFInfo
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- JP7200381B2 JP7200381B2 JP2021536297A JP2021536297A JP7200381B2 JP 7200381 B2 JP7200381 B2 JP 7200381B2 JP 2021536297 A JP2021536297 A JP 2021536297A JP 2021536297 A JP2021536297 A JP 2021536297A JP 7200381 B2 JP7200381 B2 JP 7200381B2
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- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
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- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 1
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Description
R2は、それぞれ独立して基7~基12からなる群から選択され、
式中、Rは、C1~C30のアルキル基、C3~C30のシクロアルキル基、C1~C30のアルコキシ基からなる群から選択され、n>4であり、
R3は、それぞれ独立してC6~C30のアルキル基、C3~C30のシクロアルキル基、C6~C30のアルコキシ基及び酸素含有エーテル鎖から選択される。
窒素保護下、100mL三口フラスコに1-ブロモ-4-ヘキシルベンゼン(1.06g、4.49mmol)と、無水テトラヒドロフラン30mLとを入れ、-78℃まで降温し、n-BuLi(2.8mL、1.6Mのn-ヘキサン溶液)をゆっくり滴下し、-78℃で30分間反応させた後、エチル2-ブロモ-3-チオフェンカルボキシレート(0.5g、1.12mmol)を滴下して4h反応させた。反応終了後、水でクエンチし、酢酸エチル(3×50mL)で抽出し、有機相を合わせ、有機相を水、飽和NaClで順次洗浄し、無水硫酸ナトリウムで乾燥した。溶媒を留去し、黄色液体粗生成物中間体を得た。
1H NMR(400MHz,CDCl3),δ(ppm):7.28(dd,J=13.9,6.1Hz,4H),7.12-7.03(m,6H),6.99(d,J=4.9Hz,1H),6.96(d,J=5.3Hz,1H),3.71(d,J=8.1Hz,2H),2.58(t,J=7.8Hz,4H),1.59(dd,J=8.1,4.3Hz,6H),1.38-1.27(m,15H),1.11-1.03(m,2H),0.91(d,J=6.7Hz,6H),0.77(t,J=7.3Hz,3H),0.57(d,J=4.4Hz.6H).13C NMR(101MHz,CDCl3)δ144.94,144.56,141.69,141.47,141.08,136.89,135.61,135.17,134.21,133.53,133.50,131.84,131.24,131.04,129.10,128.33,128.16,127.89,126.04,122.91,122.87,122.76,122.70,114.70,114.63,114.55,110.89,110.83,110.32,110.04,108.68,77.32,77.00,76.68,51.19,51.11,40.38,40.33,35.68,35.57,32.02,31.81,31.71,31.68,31.32,30.60,29.03,28.64,24.03,23.96,22.96,22.93,22.85,22.74,22.58,22.48,14.08,14.01,13.96,13.93,10.65,10.60.。
100mLの三口フラスコに7(0.20g、0.28mmol)および30mLの乾燥クロロホルムを加え、窒素を吸引して0℃に降温し、NBS(79.6mg、0.62mmol)のDMF溶液(2mL)に加え、0℃で30分間避光反応を行った。有機溶媒を減圧留去し、石油エーテルを溶離液として直接カラムクロマトグラフィーで分離し、黄色固体8(0.19g、78.8%)を得た。
1H NMR(CDCl3,400MHz),δ(ppm):δ7.29(s,1H),7.12(d,J=8.3Hz,4H),6.96(d,J=7.1Hz,4H),6.79(s,1H),3.90(t,J=7.6Hz,2H),2.58(t,J=7.8Hz,4H),2.04(t,J=7.4Hz,3H),1.59(q,J=7.3Hz,6H),1.33-1.27(m,24H),0.88(dd,J=8.1,2.3Hz,14H),0.55(ddt,J=12.3,7.2,4.0Hz,2H).;13C NMR(100MHz,CDCl3),δ(ppm):143.64,142.63,142.03,137.41,136.08,135.89,134.68,133.57,132.59,132.53,129.06,128.48,128.43,128.01,126.03,114.66,114.27,114.22,110.21,109.85,109.62,108.75,77.32,77.00,76.68,53.40,51.24,40.30,35.56,32.05,31.69,31.32,30.55,29.01,28.60,23.93,22.92,22.58,22.41,14.07,13.98,13.90,10.57.
25mL三口フラスコ中で、化合物8(80mg,0.113mmol)および化合物9(137mg,0.113mmol)を、トルエン4.5mLとN,N-ジメチルホルムアミド0.5mLとの混合溶媒に溶解させ、窒素を15分間バブリングした。Pd2(dba)3を5.17mg及びp-(o-tol)6mg加え、4時間加熱還流し、溶液が粘稠になったところで直ちに加熱を停止し、冷却後、無水メタノール100mL中に導入して沈降し、吸引濾過し、ソックスレー抽出器で精製した後、カラムクロマトグラフィーで2次精製を行い、青黒色固体100.1gを得た。
化合物10の熱安定性は、TA instrument SDT-TG Q600熱重量分析装置上で、図5および6に示されるように、窒素流下加熱走査速度10℃/分で、熱重量分析(TG)によって行った。
本発明は、化合物10の溶液及び薄膜状態での吸収スペクトルをUV-Visを用いて測定した結果を図7に示す。
電気化学的特性の試験は、上海華晨CHI600E電気化学分析器の電気化学的ステーションを用いて行い、電解セルは三電極系(グラッシーカーボン電極が作用極、白金ワイヤー電極が補助電極、カロメル電極が参照電極)であり、内部標準としてフェロセンを用い、0.1Mのテトラブチルヘキサフルオロホスホラミン(n-Bu4NPF6)を支持電解質として、走査速度は100mVs-1である。アルゴン保護下でのそのサイクリックボルタンメトリ曲線を図8及び表1に示す。
[光起電力素子の作製]
図9に示すように、素子構造はITO/SnO2/Perovskite/HTM/MoO3/Agである。具体的な手順は以下の通りである。
R1は、それぞれ独立してC1~C30のアルキル基、C3~C30のシクロアルキル基、C1~C30のアルコキシ基からなる群から選択されるいずれか1つであることを特徴とする、付記1に記載の非対称有機高分子。
R2は、それぞれ独立して基7~基12からなる群から選択されるいずれか1つであることを特徴とする、付記2に記載の非対称有機高分子。
(式中、Rは、C1~C30のアルキル基、C3~C30のシクロアルキル基、C1~C30のアルコキシ基からなる群から選択されるいずれか1つであり、n>4である。)
R3は、それぞれ独立してC6~C30のアルキル基、C3~C30のシクロアルキル基、C6~C30のアルコキシ基及び酸素含有エーテル鎖からなる群から選択されるいずれか1つであることを特徴とする、付記3に記載の非対称有機高分子。
前記非対称有機高分子は、電子供与性D単位と電子求引性A単位とを、溶媒および触媒の存在下、Stilleカップリング反応させて重合することにより得られるものであることを特徴とする、付記1~5のいずれか一つに記載の非対称有機高分子の製造方法。
電子供与性D単位は、それぞれ独立して下記の式で表される基13~基17から選択され、電子求引性A単位は、それぞれ独立して下記の式で表される基18および基19から選択されることを特徴とする、付記6に記載の非対称有機高分子の製造方法。
(式中、R1は、それぞれ独立してC1~C30のアルキル基、C3~C30のシクロアルキル基、C1~C30のアルコキシ基からなる群から選択されるいずれか1つであり、
R2は、それぞれ独立して基7~基12からなる群から選択されるいずれか1つであり、
式中、Rは、C1~C30のアルキル基、C3~C30のシクロアルキル基、C1~C30のアルコキシ基からなる群から選択されるいずれか1つであり、n>4であり、
R3は、それぞれ独立してC6~C30のアルキル基、C3~C30のシクロアルキル基、C6~C30のアルコキシ基及び酸素含有エーテル鎖からなる群から選択されるいずれか1つである。)
前記溶媒は、混合溶媒であり、好ましくはトルエンとN,N-ジメチルホルムアミドとの混合溶媒であり、溶媒の体積比はトルエン:N,N-ジメチルホルムアミド混合溶媒=6~10:1であることを特徴とする、付記6に記載の非対称有機高分子の製造方法。
前記触媒はPd2(dba)3またはPd(PPh3)4であることを特徴とする、付記7に記載の非対称有機高分子の製造方法。
前記製造方法は保護ガス下で行われ、前記保護ガスは窒素またはアルゴンが好ましいことを特徴とする、付記8に記載の非対称有機高分子の製造方法。
付記1~5のいずれか一つに記載の非対称有機高分子のペロブスカイト太陽電池の製造における使用。
前記非対称有機高分子はペロブスカイト電池の光活性層における正孔輸送層の製造に使用されることを特徴とする、付記11に記載の使用。
Claims (11)
- 下記構造式の化合物1-1~5-2から選択されるいずれか1つを含む、電子供与性単位と電子求引性単位とを含む非対称有機高分子であって、
R1は、それぞれ独立してC1~C30のアルキル基、C3~C30のシクロアルキル基、C1~C30のアルコキシ基からなる群から選択されるいずれか1つであり、
R2は、それぞれ独立して基7~基12からなる群から選択されるいずれか1つであり、
式中、Rは、C1~C30のアルキル基、C3~C30のシクロアルキル基、C1~C30のアルコキシ基からなる群から選択されるいずれか1つであり、n>4であり、
R3は、それぞれ独立してC6~C30のアルキル基、C3~C30のシクロアルキル基、C6~C30のアルコキシ基及び酸素含有エーテル鎖からなる群から選択されるいずれか1つであることを特徴とする、非対称有機高分子。 - 前記非対称有機高分子は、電子供与性D単位と電子求引性A単位とを、溶媒および触媒の存在下、Stilleカップリング反応させて重合することにより得られるものであることを特徴とする、請求項1または2に記載の非対称有機高分子の製造方法。
- 電子供与性D単位は、それぞれ独立して下記の式で表される基13~基17から選択され、電子求引性A単位は、それぞれ独立して下記の式で表される基18および基19から選択されることを特徴とする、請求項3に記載の非対称有機高分子の製造方法。
(式中、R1は、それぞれ独立してC1~C30のアルキル基、C3~C30のシクロアルキル基、C1~C30のアルコキシ基からなる群から選択されるいずれか1つであり、
R2は、それぞれ独立して基7~基12からなる群から選択されるいずれか1つであり、
式中、Rは、C1~C30のアルキル基、C3~C30のシクロアルキル基、C1~C30のアルコキシ基からなる群から選択されるいずれか1つであり、n>4であり、
R3は、それぞれ独立してC6~C30のアルキル基、C3~C30のシクロアルキル基、C6~C30のアルコキシ基及び酸素含有エーテル鎖からなる群から選択されるいずれか1つである。) - 前記溶媒は、混合溶媒であることを特徴とする、請求項3に記載の非対称有機高分子の製造方法。
- 前記混合溶媒は、トルエンとN,N-ジメチルホルムアミドとの混合溶媒であり、溶媒の体積比はトルエン:N,N-ジメチルホルムアミド=6~10:1であることを特徴とする、請求項5に記載の非対称有機高分子の製造方法。
- 前記触媒はPd2(dba)3またはPd(PPh3)4であることを特徴とする、請求項4に記載の非対称有機高分子の製造方法。
- 前記製造方法は保護ガス下で行われることを特徴とする、請求項5に記載の非対称有機高分子の製造方法。
- 前記保護ガスは窒素またはアルゴンであることを特徴とする、請求項8に記載の非対称有機高分子の製造方法。
- 請求項1または2に記載の非対称有機高分子のペロブスカイト太陽電池の製造における使用。
- 前記非対称有機高分子はペロブスカイト電池の光活性層における正孔輸送層の製造に使用されることを特徴とする、請求項10に記載の使用。
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