JP6095229B2 - ビベンゾ[b]フラン化合物、光電変換材料及び光電変換素子 - Google Patents
ビベンゾ[b]フラン化合物、光電変換材料及び光電変換素子 Download PDFInfo
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- JP6095229B2 JP6095229B2 JP2013540764A JP2013540764A JP6095229B2 JP 6095229 B2 JP6095229 B2 JP 6095229B2 JP 2013540764 A JP2013540764 A JP 2013540764A JP 2013540764 A JP2013540764 A JP 2013540764A JP 6095229 B2 JP6095229 B2 JP 6095229B2
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
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- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 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
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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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。
特許文献1〜3には、高分子型のp型有機半導体に関する開示がなされている。
しかしながら、有機系太陽電池のより一層の光電変換効率向上が要望されている。
また本発明の目的は、上記p型有機半導体材料を用いた高い光電変換効率を有する光電変換材料、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。
第一のビベンゾ[b]フラン化合物は、上記式(1)又は(2)で表される構成単位を少なくとも1つ有する化合物である。尚、上記式(1)又は(2)中の*は、これらの式で表される基が、*部分で、隣接する基と結合することを意味する(以下同様)。
上記芳香族炭化水素基としては、例えば、フェニル、ナフチル、シクロヘキシルフェニル、ビフェニル、ターフェニル、フルオレイル、チオフェニルフェニル、フラニルフェニル、2’−フェニル−プロピルフェニル、ベンジル、ナフチルメチル等が挙げられ、
上記脂肪族炭化水素基としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、s−ブチル、t−ブチル、イソブチル、アミル、イソアミル、t−アミル、ヘキシル、ヘプチル、イソヘプチル、t−ヘプチル、n−オクチル、イソオクチル、t−オクチル、ノニル、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、シクロノニル、シクロデシル等の直鎖、分岐及び環状のアルキル基が挙げられ、これら脂肪族炭化水素基は、−O−、−COO−、−OCO−、−CO−、−S−、−SO−、−SO2−、−NR15−、−HC=CH−又は−C≡C−で中断されていてもよく(尚、該中断は脂肪族炭化水素基の結合する部分を中断していてもよい)、R15は、置換されていてもよい炭化水素基を表し、置換されていてもよい炭化水素基としては、R13及びR14が表す置換されていてもよい炭化水素基と同様の基が挙げられ、中でもパーフルオロアルキルが好ましい。
上記脂肪族炭化水素で置換された芳香族炭化水素基としては、上記脂肪族炭化水素基により置換されたフェニル、ナフチル、ベンジル等が挙げられる。
これらの炭化水素基を置換してもよい基としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子、シアノ基、ニトロ基、水酸基、チオール基、−NR’R”基等が挙げられ、R’及びR”は、置換されていてもよい炭化水素基を表し、置換されていてもよい炭化水素基としては、R13及びR14が表す置換されていてもよい炭化水素基と同様の基が挙げられる。
また、上記一般式(4)で表される化合物の中でも、Y3、Y4又はZ2の少なくとも一つが単結合ではない化合物は、製造が容易であるため好ましい。
続いて、ジブロモビベンゾ[b]フラン(A)に、対応するY1−又はY2−を有するボロン酸ピナコールエステル誘導体をカップリングさせ中間体(B)とした後、トリメチルフェニルアンモニウムブロミドにて臭素化して中間体(C)とし、対応するZ1−又はZ2−を有するビスボロン酸ピナコールエステル誘導体にて高分子量化して中間体(D)とし、末端をキャッピングすることにより上記一般式(3)で表わされる化合物を得ることが出来る。尚、中間体(D)の生成後にクエンチした場合、R1及びR2は水素原子となる。
本発明の光電変換材料は、(A)第一のビベンゾ[b]フラン化合物を少なくとも一種含有するp型有機半導体材料、及び(B)n型有機半導体材料を含有するものである。
チルオクチロキシ)−1,4−フェニレンビニレン])、ポリチオフェン及びその誘導体(例えば、ポリ(3−ドデシルチオフェン)、ポリ(3−ヘキシルチオフェン):P3HT、ポリ(3−オクチルチオフェン))、ポリ−N−ビニルカルバゾール誘導体等が挙げられる。
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。
第二のビベンゾ[b]フラン化合物は、上記一般式(B1)又は(B2)で表される。
尚、特に説明しない部分については、第一のビベンゾ[b]フラン化合物における説明が適宜適用される。
続いて、ジブロモビベンゾ[b]フラン(A)と、R21−X−及びR22−X−に対応する合成中間体とのカップリング反応を経て、目的の第二のビベンゾ[b]フラン化合物を得ることができる。
また、R21−X−及びR22−X−の構造によっては、ブロモ化せずに、3,4:3'4'−ビベンゾ[b]フランに対し、直接、R21−X−及びR22−X−に対応する合成中間体とのカップリング反応を行うことができる。
<ステップ1>下記〔化13〕に示すジカルボン酸体の合成
アントラルフィン25.0g(0.10mol)、2−ブタノン470ml、炭酸カリウム54.7g(0.40mol)、及びブロモ酢酸エチル60.8g(0.36mol)を仕込んだ溶液を、90℃まで昇温し、6時間反応させた後、室温まで冷却し塩酸を加え、ろ過した。残渣を塩酸、超純水、メタノールにて洗浄した後、減圧にて乾燥させ、茶色結晶42.1gを得た(収率98%)。
引き続き、上記茶色結晶36.0g(0.09mol)、水酸化ナトリウム12.1g(0.30mol)、超純水32.0g、エタノール65g、及び2−ブタノン600mlを仕込んだ溶液を90℃まで昇温し、6時間反応させた後、室温付近まで冷却し塩酸を加え、残渣をろ過した。この残渣を塩酸、超純水、トルエンにて洗浄した後、減圧にて乾燥させ、黄緑色結晶のジカルボン酸体30.8gを得た(収率99%)。得られた黄緑色結晶が目的物のジカルボン酸体であることは1H−NMRで確認した。分析結果を次に示す。
1H−NMR(DMSO−D6)δ:13.09(2H、s)、7.80−7.71(4H、m)、7.37(2H、d、J=7.3Hz)、4.91(4H、s)
ステップ1で得られたジカルボン酸体200mg(0.56mmol)、4−ピコリン3.6g、及び無水酢酸3.3gを仕込んだ溶液を175℃まで昇温した後、2時間反応させた。5℃まで冷却し、塩酸及びクロロホルムを加え、油水分離し、有機層を塩酸、飽和炭酸水素ナトリウム水溶液、超純水にて洗浄した。有機層に硫酸マグネシウムを加えて乾燥させ、ろ過、減圧濃縮した後、薄層クロマトクロマトグラフィー(ヘキサン−クロロホルム)にてBBFの生成を確認した。得られた化合物が目的物のBBFであることは1H−NMR及び13C−NMRで確認した。また質量分析も行った。分析結果を次に示す。
1H−NMR(CDCl3)δ:7.89(2H、s)、7.42(2H、dd、J=5.8、2.1Hz)、7.32(4H、t、J=3.0Hz)
13C−NMR(CDCl3)δ:154.13、137.91、128.74、126.39、123.63、117.90、117.17、110.23
MS(TOF−MS、Dith):m/z 232.2(100%)、464.3(8%)
MS(TOF−MS、DHB):m/z 232.2(100%)、464.3(14%)
<ステップ3>BBF−Br2の合成
窒素雰囲気下、ステップ2で得られたBBFの1.0g(4.3mmol)、及びジメチルホルムアミド(DMF)22mlを仕込んだ溶液を0℃まで冷却した後、N−ブロモこはく酸イミド(NBS)1.8g(10.3mmol)のDMF溶液15mlを滴下し、20分間撹拌した。室温まで昇温し2時間反応させ、超純水及びトルエンを加え油水分離し、有機層を超純水で洗浄した。有機層を硫酸マグネシウムで乾燥させた後、ろ過、減圧濃縮、シリカゲルカラムクロマトグラフィーにて精製し(展開溶媒:ヘキサン−トルエン)、茶色結晶を171mg得た(収率10%)。得られた茶色結晶が目的物のBBF−Br2であることは1H−NMRで確認した。分析結果を次に示す。
1H−NMR(CDCl3)δ:7.75(2H、d、J=7.3Hz)、7.39−7.31(4H、m)
窒素雰囲気下、中間体合成例1で得られたBBF−Br2を1.0g(2.56mmol)、及びトルエン130mlを仕込んだ溶液を超音波照射し、更にこの溶液に3−ヘキシル−2−チオフェンボロン酸ピナコールエステル2.1g(7.17mmol)、テトラキス(トリフェニルホスフィン)パラジウム300mg(0.26 mmol)、及び炭酸ナトリウム水溶液6.4ml(2.0M、12.8mmol)を加え、110℃で7時間反応させた。更に、3−ヘキシル−2−チオフェンボロン酸ピナコールエステル1.4g(4.76mmol)、及びテトラキス(トリフェニルホスフィン)パラジウム250mg(0.22 mmol)を加え、110℃で5時間反応させた。塩酸及びトルエンを加え油水分離し、有機層を超純水にて2回洗浄した。有機層を硫酸マグネシウムで乾燥させた後、ろ過、減圧濃縮、シリカゲルカラムクロマトグラフィーにて精製し(展開溶媒:ヘキサン−トルエン)、黄色油状物を1.45g得た(収率99%)。得られた黄色油状物が目的物のBBF−3HTであることは1H−NMRで確認した。分析結果を次に示す。
1H−NMR(CDCl3)δ:7.50(2H、d、J=26.2Hz)、7.37(2H、d、J=18.3Hz)、7.33−7.27(4H、m)、7.11(2H、d、J=18.9Hz)、2.72(4H、t、J=48.2Hz)、1.67−1.55(4H、m)、1.31−1.08(12H、m)、0.76(6H、t、J=46.3Hz)
中間体合成例2で得られたBBF−3HTを100mg(0.24mmol)、及びテトラヒドロフラン(THF)6.5mlを仕込んだ溶液に、トリメチルフェニルアンモニウムブロミド(PTMA-Br3)266 mg(0.71 mmol)のTHF溶液1.0mlを滴下し、室温で30分間撹拌した。チオ硫酸ナトリウム水溶液、及びトルエンを加え油水分離し、有機層を超純水で洗浄した。有機層を硫酸マグネシウムで乾燥させた後、ろ過、減圧濃縮、シリカゲルカラムクロマトグラフィーにて精製し(展開溶媒:ヘキサン−トルエン)、黄色結晶を142mg得た(収率99%)。得られた黄色結晶が目的物のBBF−3HTBであることは1H−NMRで確認した。分析結果を次に示す。
1H−NMR(CDCl3)δ:7.40−7.34(2H、m)、7.34−7.29(4H、m)、7.07(2H、s)、2.64(4H、t、J=48.8Hz)、1.64−1.50(4H、m)、1.28−1.06(12H、m)、0.76(6H、t、J=44.5Hz)
中間体合成例3で合成したBBF−3HTBを0.19g(0.33mmol)、及びトルエン20mlを仕込んだ溶液を超音波照射し、更にこの溶液に3−ヘキシル−2−チオフェンボロン酸ピナコールエステル0.26g(0.92mmol)、テトラキス(トリフェニルホスフィン)パラジウム38mg(0.033mmol)、及び炭酸ナトリウム水溶液0.83ml(2M、1.65mmol)を加え、110℃で8時間反応させた。更に、3−ヘキシル−2−チオフェンボロン酸ピナコールエステル0.17g(0.61mmol)、及びテトラキス(トリフェニルホスフィン)パラジウム32mg(0.027mmol)を加え、110℃で5時間反応させた。塩酸及びトルエンを加え油水分離し、有機層を超純水にて2回洗浄した。有機層を硫酸マグネシウムで乾燥させた後、ろ過、減圧濃縮、シリカゲルカラムクロマトグラフィーにて精製した。精製物をテトラヒドロフラン(THF)9mlに溶解し、トリメチルフェニルアンモニウムブロミド(PTMA−Br3)355mg(0.95mmol)のTHF溶液1.3mlを滴下し、室温で30分間攪拌した。チオ硫酸ナトリウム水溶液、及びトルエンを加え油水分離し、有機層を超純水で洗浄した。有機層を硫酸マグネシウムで乾燥させた後、ろ過、減圧濃縮、シリカゲルカラムクロマトグラフィーにて精製し(展開溶媒:ヘキサン−トルエン)、橙色結晶のBBF−3HT2Bを0.24g得た(収率93%)。同定は1H−NMRにて行った。分析結果を次に示す。
1H−NMR(CDCl3)δ:7.54−7.44(2H、m)、7.37−7.27(4H、m)、7.05(2H、s)、6.94(2H、s)、2.78(4H、t、J=27.4Hz)、2.71(4H、t、J=26.8Hz)、1.71−1.58(8H、m)、1.45−1.12(24H、m)、0.88(6H、t、J=37.2Hz)、0.77(6H、t、J=26.2Hz)
中間体合成例2で用いた3−ヘキシル−2−チオフェンボロン酸ピナコールエステルを4−ヘキシル−2−チオフェンボロン酸ピナコールエステルに変更した以外は中間体合成例2と同様の手順で反応させ、BBF−4HTとし、更に、中間体合成例3と同様の手順で臭素化し、黄色結晶のBBF−4HTBを141mg得た(収率99%)。同定は、1H−NMRにて行った。分析結果を次に示す。
1H−NMR(CDCl3)δ:7.91(2H、d、J=30.5Hz)、7.48(2H、s)、7.34(4H、q、J=50.0Hz)、2.68(4H、t、J=59.1Hz)、1.78−1.63(4H、m)、1.49−1.29(12H、m)、0.92(6H、t、J=78.7Hz)
窒素雰囲気下、中間体合成例3で合成したBBF−3HTBを180mg(0.25mmol)、及びトルエン10mlを仕込んだ溶液を超音波照射し、更にこの溶液に2,1,3−ベンゾチアジアゾール−4,7−ビス(ボロン酸ピナコールエステル)97mg(0.21mmol)、トリス(ジベンジリデンアセトン)ジパラジウム11mg(0.013 mmol)、トリ(o−トリル)ホスフィン23mg(0.075mmol)、及び炭酸ナトリウム水溶液1.7ml(2.0M、3.4mmol)を加え、120℃で6時間反応させた。更に、トリス(ジベンジリデンアセトン)ジパラジウム11mg(0.013 mmol)、及びトリ(o−トリル)ホスフィン23mg(0.075mmol)を加え、120℃で6時間反応させた。メタノールを加え再沈殿させ、得られた残渣をメタノール、超純水にて洗浄し、アセトン中で還流した。溶液をろ過後、アセトンで洗浄し、乾燥させ、黒紫色結晶の化合物No.5を126mg得た(収率99%)。得られた化合物No.5の数平均分子量(Mn)は3638であり、重量平均分子量(Mw)は5800であり、Mw/Mnは1.59であった。
窒素雰囲気下、中間体合成例2で合成したBBF−3HTを300mg(0.53mmol)、及びクロロホルム53mlを仕込んだ溶液に、塩化鉄(III)580mg(3.58mmol)を加え、室温で40時間反応させた。ヒドラジン一水和物を加え4時間撹拌した後、メタノールを加え再沈殿させ、得られた残渣をメタノール、超純水にて洗浄し、アセトン中で還流した。得られた残渣を乾燥させ、赤暗色固体の化合物No.6を390mg得た(収率95%)。得られた化合物No.6の数平均分子量(Mn)は、6236であり、重量平均分子量(Mw)は15437であり、Mw/Mnは2.47であった。
窒素雰囲気下、中間体合成例4で合成したBBF−3HT2Bを200mg(0.19mmol)、2,1,3−ベンゾチアジアゾール−4,7−ビス(ボロン酸ピナコールエステル)81mg(0.21mmol)、及びトルエン15mlを仕込んだ溶液を超音波照射し、更にこの溶液に、テトラキス(トリフェニルホスフィン)パラジウム22mg(0.019mmol)、及び炭酸ナトリウム水溶液8.0ml(2.0M、16.0mmol)を加え、90℃で12時間反応させた。フェニルボロン酸232mg(1.9mmol)、及びテトラキス(トリフェニルホスフィン)パラジウム11mg(0.001mmol)、を加え、90℃で4時間反応させた後、更にファニルブロミド298mg(1.9mmol)、及びテトラキス(トリフェニルホスフィン)パラジウム11mg(0.001mmol)を加え90℃で4時間反応させた。室温まで冷却し、メタノールを加え再沈殿させ、得られた残渣をメタノール、超純水にて洗浄した。更にこの残渣をソックスレー抽出器を用いてアセトンで9時間洗浄した後、乾燥させ、黒紫色結晶の化合物No.7を143mg得た(収率72%)。得られた化合物No.7の数平均分子量(Mn)は、2980であり、重量平均分子量(Mw)は4073であり、Mw/Mnは1.37であった。
実施例3で用いた手法と同様の手法により、化合物No.8〜11、化合物No.13、化合物No.14、化合物No.29及び化合物No.71〜78を合成した。収率及び分子量を〔表1〕に示す。
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、電荷移動層3として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た。1,2−ジクロロベンゼン2mLに(A)p型有機半導体として実施例1の化合物を20mg、及び(B)n型有機半導体としてPCBMを80mg溶解させて、実施例19の光電変換材料を調製した。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の上に、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19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2]に示す。
上記実施例19の光電変換素子の作製において、(A)成分、(B)成分及びそれらの組成比を〔表2〕に示すように変更する以外は、実施例19と同様にして、実施例20〜60の光電変換素子を作製した。また、実施例19と同様の操作で、実施例20〜60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2〕に示す。
上記実施例19の光電変換素子の作製において、(A)成分として、本発明の化合物の代わりに、下記〔化18〕に示す比較化合物No.1〜4を用い、〔表3〕に記載の配合量に従い実施例19と同様の操作で、比較例1〜10の光電変換素子を作製し、実施例19と同様の操作で、比較例1〜10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3〕に示す。
比較化合物No.2:自社合成品
比較化合物No.3:Aldrich社製、数平均分子量>20000
比較化合物No.4:Aldrich社製、数平均分子量10000〜20000
従って、本発明のビベンゾ[b]フラン化合物を用いた光電変換材料は、光電変換素子及び有機薄膜太陽電池に有用である。
Claims (8)
- 下記式(1)又は(2)で表される構成単位を2以上100以下と、該式(1)又は(2)で表される構成単位以外のπ共役の基とのみからなり、
上記π共役の基が下記群Y又は群Zから選ばれるものであるビベンゾ[b]フラン化合物。
R5基、置換されていてもよい炭化水素基又は置換されていてもよい複素環基で置換され
ていてもよく、R4及びR5は、置換されていてもよい炭化水素基を表す。)
し、群Zで表される構成単位中の水素原子は、フッ素原子、塩素原子、臭素原子、ヨウ素原子、シアノ基、ニトロ基、水酸基、チオール基、−NR9R10基、置換されていてもよ
い炭化水素基又は置換されていてもよい複素環基で置換されていてもよく、R9及びR10
は、置換されていてもよい炭化水素基を表す。) - 下記一般式(1’)又は(2’)で表される請求項1に記載のビベンゾ[b]フラン化合物。
- 下記一般式(3)又は(4)で表される請求項1に記載のビベンゾ[b]フラン化合物。
R8を表し、X5はS、O又はNR6を表し、R6、R7及びR8は、置換されていてもよい炭化水素基を表し、(Z−1)〜(Z−21)基中の水素原子は、フッ素原子、塩素原子、臭素原子、ヨウ素原子、シアノ基、ニトロ基、水酸基、チオール基、−NR9R10基、置
換されていてもよい炭化水素基又は置換されていてもよい複素環基で置換されていてもよく、R9及びR10は、置換されていてもよい炭化水素基を表す。) - (A)請求項1〜3の何れか1項に記載のビベンゾ[b]フラン化合物を少なくとも一種を含有するp型有機半導体材料、及び(B)n型有機半導体材料を含有してなる光電変換材料。
- 請求項4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5に記載の光電変換層を有してなる光電変換素子。
- 請求項6に記載の光電変換素子を有してなる有機薄膜太陽電池。
- 下記一般式(B1)又は(B2)で表されるビベンゾ[b]フラン化合物。
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PCT/JP2012/077208 WO2013061909A1 (ja) | 2011-10-24 | 2012-10-22 | ビベンゾ[b]フラン化合物、光電変換材料及び光電変換素子 |
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TWI582082B (zh) | 2017-05-11 |
TW201326146A (zh) | 2013-07-01 |
CN108250208A (zh) | 2018-07-06 |
US20140252278A1 (en) | 2014-09-11 |
EP2772494A1 (en) | 2014-09-03 |
KR20140083969A (ko) | 2014-07-04 |
US9450119B2 (en) | 2016-09-20 |
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