JP6625546B2 - ピセン誘導体、光電変換材料及び光電変換素子 - Google Patents
ピセン誘導体、光電変換材料及び光電変換素子 Download PDFInfo
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- JP6625546B2 JP6625546B2 JP2016555186A JP2016555186A JP6625546B2 JP 6625546 B2 JP6625546 B2 JP 6625546B2 JP 2016555186 A JP2016555186 A JP 2016555186A JP 2016555186 A JP2016555186 A JP 2016555186A JP 6625546 B2 JP6625546 B2 JP 6625546B2
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- photoelectric conversion
- substituted
- unsubstituted hydrocarbon
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- 239000000463 material Substances 0.000 title claims description 57
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
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- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
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- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical group C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical group [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 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
- 229930192474 thiophene Natural products 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
- 150000003613 toluenes Chemical class 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
- 229940036248 turpentine Drugs 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-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
- 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。
また本発明の目的は、上記p型有機半導体材料を用いて高い光電変換効率を有する光電変換層、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。
(式中、A1及びA2は、それぞれ独立に単環を表し、
R1、R2、R3、R4、R5及びR6は、それぞれ独立に水素原子、ハロゲン原子、シアノ基、ニトロ基、水酸基、カルボキシル基、チオール基、−SiR7R8R9、−NR10R11基、又は置換基を有している若しくは無置換の炭化水素基を表し、
R1、R2、R3、R4、R5及びR6の少なくとも一つは水素原子では無く、
R7、R8、R9、R10又はR11はそれぞれ独立に水素原子又は置換基を有している若しくは無置換の炭化水素基を表す。)
ピセン誘導体は、上記一般式(1)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、上記一般式(1)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)。
R7、R8、R9、R10又はR11はそれぞれ独立に水素原子又は置換基を有している又は無置換の炭化水素基を示す。
上記一般式(1)において、ハロゲン原子としては、フッ素、塩素、臭素、ヨウ素等が挙げられ、
上記炭化水素基としては、芳香族炭化水素基、脂肪族炭化水素で置換された芳香族炭化水素基、脂肪族炭化水素基が挙げられ、炭素原子数1〜40、特に4〜22であるものが好ましい。
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、置換基を有している又は無置換の炭化水素基を表し、置換基を有している又は無置換の炭化水素基としては、上記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、ハロゲン原子、シアノ基、ニトロ基、水酸基、カルボキシル基、チオール基、−NR’R”基等が挙げられ、R’及びR”は、置換基を有している又は無置換の炭化水素基を表し、置換基を有している又は無置換の炭化水素基としては、上記と同様の基が挙げられる。
(式中、A3及びA4は、上記A1及びA2で例示した内の6員環であるものを表し、
A5及びA6は、上記A1及びA2で例示した内の5員環であるものを表し、
R1、R2、R3、R4、R5又はR6は、上記一般式(1)と同様であり、
R1、R2、R3、R4、R5及びR6の少なくとも一つは水素原子ではない。)
(式中、X1及びX4はS、O又はNR12を表し、
kは1〜4の整数を表し、
R12は置換されている若しくは無置換の炭化水素基を表し、
群Yで表される構成単位中の水素原子は、ハロゲン原子、シアノ基、ニトロ基、水酸基、カルボキシル基、チオール基、−NR13R14基、置換されている若しくは無置換の炭化水素基又は置換されていている若しくは無置換の複素環基で置換されていてもよく、
R13及びR14は、置換されていている又は無置換の炭化水素基を表す。)
(式中、X2はS又はNR15を表し、
X3はS、NR15、CR16R17又はSiR16R17を表し、
X5はS、O又はNR15を表し、
R15、R16及びR17は、置換されている若しくは無置換の炭化水素基を表し、
群Zで表される構成単位中の水素原子は、ハロゲン原子、シアノ基、ニトロ基、水酸基、カルボキシル基、チオール基、−NR18R19基、置換されている若しくは無置換の炭化水素基又は置換されている若しくは無置換の複素環基で置換されていてもよく、
R18及びR19は、置換されている若しくは無置換の炭化水素基を表す。)
(式中の水素原子は、上記一般式(1)と同様に置換されていてもよく、
Yは上記群Yから選ばれる基を表し、
Zは上記群Zから選ばれる基を表し、
oは1以上1000以下を表し、
p及びqは、0以上1000以下を表す。)
(式中、A1、A2、R1、R2、R3、R4、R5及びR6は、上記式(1)と同様の基を表し、
R1、R2、R3、R4、R5及びR6の少なくとも一つは水素原子では無く、
Y1及びY2は単結合又は下記(Y−1)〜(Y−8)から選ばれる基を1〜5個組み合わせて連結した基であり、
Z1は、単結合又は下記(Z−1)〜(Z−21)から選ばれる基を表し、
nは1以上1000以下の整数を表す。)
(式中、X1及びX4はS、O又はNR12を表し、
kは1〜4の整数を表し、
R12は置換されている若しくは無置換の炭化水素基を表し、
(Y−1)〜(Y−4)及び(Y−6)〜(Y−8)で表される基中の水素原子は、ハロゲン原子、シアノ基、ニトロ基、水酸基、カルボキシル基、チオール基、−NR13R14基、置換されている若しくは無置換の炭化水素基又は置換されている若しくは無置換の複素環基で置換されていてもよく、
R13及びR14は、置換されている若しくは無置換の炭化水素基を表す。)
(式中、X2はS又はNR15を表し、
X3はS、NR15、CR16R17又はSiR16R17を表し、
X5はS、O又はNR15を表し、
R15、R16及びR17は、置換されている若しくは無置換の炭化水素基を表し、
(Z−1)〜(Z−21)で表される基中の水素原子は、ハロゲン原子、シアノ基、ニトロ基、水酸基、カルボキシル基、チオール基、−NR18R19基、置換されている若しくは無置換の炭化水素基又は置換されている若しくは無置換の複素環基で置換されていてもよく、
R18及びR19は、置換されている若しくは無置換の炭化水素基を表す。)
(式中、A1、A2、R1、R2、R3、R4、R5及びR6は、上記式(1)と同様の基を表し、
A3及びA4は、上記式(1−1)と同様であり、
A5及びA6は、上記式(1−2)と同様であり、
Y1、Y2、Z1及びnは、上記式(2)と同様であり、
R1、R2、R3、R4、R5及びR6の少なくとも一つは水素原子ではない。)
また、一般式(2)、(2−1)又は(2−2)で表される化合物において、R1、R2、R3、R4、R5及びR6の少なくとも一つは水素原子以外の置換基であり、R1、R2、R3、R4、R5及びR6の置換基の種類に特に限定されず本発明の効果を奏するが、好ましくは、R1、R2、R3、R4、R5及びR6の少なくとも一つが、炭素原子数1〜30の無置換アルキル基、又は炭素原子数1〜30の置換アルキル基を表し、該無置換アルキル基及び置換アルキル基中のメチレン基は、−CH=CH−又は−C≡C−を表してもよく、該アルキル基を置換してもよい置換基は、アルコキシ基、アルキルチオ基、アリール基、アリールオキシ基、アリールチオ基、複素環基、アシル基、アシルオキシ基、アミノ基、スルホニル基、カルボキシル基、シアノ基、スルホ基、水酸基、メルカプト基、イミド基、ハロゲン原子である化合物、より好ましくは炭素原子数1〜30の無置換アルキル基、又は炭素原子数1〜30の置換アルキル基である化合物、特に炭素原子数10〜20の無置換アルキル基、又は炭素原子数10〜20の置換アルキル基である化合物が好ましい。
また、R1、R2、R3、R4、R5及びR6において、水素原子以外の置換基の位置については、置換基の位置に特に限定されず本発明の効果を奏するが、好ましくは、R1、R3、R4及びR6であり、より好ましくは、R1及びR6である。
本発明の光電変換材料は、(A)ピセン誘導体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。
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)2,9-Bis(triisopropylsilyl)phenanthro[1,2-b:8,7-b']dithiophene(7a)の合成
アルゴンガス雰囲気下、50mLシュレンク管にフェナントロ[1,2-b:8,7-b']ジチオフェン(PDT) (6a) (809mg, 2.8mmol, 1equiv), 脱水THF(50mL) を加え、−78℃に冷却した。その後,n-BuLi(1.6M in hexane)(3.85mL, 6.2mmol, 2.2equiv) を滴下した後、室温まで放冷し、1時間撹拌した。撹拌後、−78℃に冷却し、TIPSCl(トリイソプロピルシリルクロライド, 1.44mL, 6.7mmol, 2.4equiv) を滴下した後、24 時間還流させた。水及び1N塩酸を加えることで反応を停止させ、クロロホルムで抽出した。飽和塩化ナトリウム水溶液で有機層を洗浄した後、無水硫酸マグネシウムで乾燥し、この混合溶液をろ過後、ロータリーエバポレーターを用いて溶媒を留去した。その後、シリカゲルカラムクロマトグラフィーで精製し、目的の化合物である7aを白色固体として 69%(1.17g, 1.9mmol) の収率で得た。以下に、シリカゲルカラムクロマトグラフィーの条件及び化合物7aの分析結果を示す。
シリカゲルカラムクロマトグラフィー (Rf=0.38, hexane)。
m.p.: 98-100℃
FT-IR (KBr, cm-1): 2941 (w), 2989 (m), 2864 (w), 1564 (s), 1460 (m), 1284 (m), 1072 (m), 949 (w), 883 (m), 842 (m), 686 (m), 592 (m).
1H NMR (600 MHz, CDCl3, rt): 1.20 (d, J = 7.2 Hz, 36H), 1.55 (sept, J = 7.2 Hz, 6H) 7.68 (s, 2H), 8.04 (d, J = 8.4 Hz, 2H), 8.26 (s, 2H), 8.65 (d, J = 9 Hz, 2H).
13C[1H] NMR (150 MHz, CDCl3, rt):11.9, 18.7, 120.2, 122.2, 123.8, 126.8, 127.4, 133.5, 135.8, 138.9, 142.9.
29Si[1H] NMR (119 MHz, CDCl3, rt):2.16.
Anal. Calcd for C36H50S2Si2: C, 71.70; H, 8.36%. Found: C, 71.72; H, 8.36%.
アルゴンガス雰囲気下、50mLシュレンク管に[Ir(OMe)(cod)]2((1,5-Cyclooctadiene)(methoxy)iridium(I)Dimer, 50mg, 0.075mmol, 5 mol %)、dtbpy (4,4-di-tert-butyl bipyridine, 40mg, 0.15mmol, 10mol%)、B2pin2(Bis(pinacolato)diboron, 762mg, 3mmol, 2equiv)、脱水シクロヘキサン(30mL)を加え、室温で10分撹拌した。その後、7a(905mg, 1.5mmol, 1 equiv)を加え、遮光下80℃で10時間撹拌した。水を加えることで反応を停止させ、クロロホルムを用いて抽出した。飽和塩化ナトリウム水溶液で有機層を洗浄した後、無水硫酸マグネシウムで乾燥し、この混合溶液をろ過後,ロータリーエバポレーターを用いて溶媒を留去した。その後、シリカゲルカラムクロマトグラフィーで精製し、目的の化合物である8aを白色固体として84%(1.07g, 1.26mmol) の収率で得た。以下に、シリカゲルカラムクロマトグラフィーの条件及び化合物8aの分析結果を示す。
シリカゲルカラムクロマトグラフィー (Rf = 0.54, hexane/ethyl acetate = 5/1)。
m.p.: 174-175℃
FT-IR (KBr, cm-1): 2943 (w), 2891 (m), 2866 (w), 1587 (m), 1463 (m), 1317 (w), 1303 (w), 1143 (w), 1099 (m), 974 (w), 846 (m), 680 (m), 605 (s).
1H NMR (600 MHz, CDCl3, rt):1.25 (d, J = 7.8 Hz, 36H), 1.48-1.53 (m, 30H), 8.33 (s, 2H), 8.48 (s, 2H), 9.32 (s, 2H).
13C[1H] NMR (150 MHz, CDCl3, rt):12.0, 18.7, 25.1, 83.9, 125.1, 126.9, 128.6, 129.2, 135.1, 136.1, 142.5, 142.7. The carbon signal adjacent to B was not observed due to low intensity.
11B[1H] NMR (192 MHz, CDCl3, rt):31.6.
29Si[1H] NMR (119 MHz, CDCl3, rt):1.96.
Anal. Calcd for C48H72B2O4S2Si2: C, 67.43; H, 8.49%. Found: C, 67.14; H, 8.52%.
50mLシュレンク管に8a(1.07g, 1.25mmol, 1equiv)、CuBr2(1.68g, 7.5mmol,6equiv)、NMP/MeOH/H2O(15mL/6mL/3mL)を加え、15時間還流させた。1N塩酸を加えることで反応を停止させ、沈殿物を濾過した後、ヘキサンで洗浄、乾燥させることで目的化合物である9aを白色固体として88%(833mg, 1.1mmol)の収率で得た。以下に、化合物9aの分析結果を示す。
m.p.: 184-185℃
FT-IR (KBr, cm-1): 2943 (w), 2889 (m), 2864 (w), 1548 (s), 1460 (m), 1087 (m), 954 (w), 881 (m), 648 (m), 599 (m).
1H NMR (600 MHz, CDCl3, rt): 1.22 (d, J = 7.2 Hz, 36H), 1.51 (sept, J = 7.2 Hz, 6H) 7.79 (s, 2H), 8.09 (s, 2H), 8.66 (s, 2H).
13C[1H] NMR (150 MHz, CDCl3, rt): 11.9, 18.6, 116.8, 123.0, 123.6, 125.9, 127.3, 133.6, 137.3, 138.7, 143.3.
29Si[1H] NMR (119 MHz, CDCl3, rt): 2.55.
Anal. Calcd for C36H48Br2S2Si2: C, 56.83; H, 6.36%. Found: C, 56.83; H, 6.30%.
アルゴンガス雰囲気下、50mLシュレンク管に1-ドデセン(412μL, 1.86 mmol, 3 equiv)、9-BBN dimer (232 mg, 0.95 mmol, 1.53 equiv)、脱水THF(12mL)を加え、60℃で1時間撹拌した。室温まで放冷した後,9a(472mg, 0.62mmol, 1equiv)、Pd(dba)2(36mg, 0.03mmol, 10mol%)、[HPtBu3]BF4(36mg, 0.06mmol, 20mol%),水酸化カリウム(209mg, 3.72mmol, 6 equiv)を加え、7時間還流させた。水を加えることで反応を停止させ、クロロホルムで抽出した。飽和塩化ナトリウム水溶液で有機層を洗浄した後、無水硫酸マグネシウムで乾燥し、この混合溶液をろ過後、ロータリーエバポレーターを用いて溶媒を留去した。その後、シリカゲルカラムクロマトグラフィーで精製し、目的の化合物である10aを無色液体として87%(506mg, 0.54mmol)の収率で得た。以下に、シリカゲルカラムクロマトグラフィーの条件及び化合物10aの分析結果を示す。
シリカゲルカラムクロマトグラフィー (Rf = 0.69, hexane)。
FT-IR (KBr, cm-1): 2924 (w), 2854 (w), 1573 (s), 1454 (w), 1382 (s), 999 (m), 883 (m), 650 (m), 500 (s).
1H NMR (600 MHz, CDCl3, rt): 0.92 (t, J = 7.2 Hz, 6H), 1.26 (d, J = 7.8 Hz, 36H), 1.30-1.37 (m, 28H), 1.45 (quin, J = 7.8 Hz, 4H), 1.51-1.57 (m, 10H), 1.93 (quin, J = 7.8 Hz, 4H), 3.22 (t, J = 7.8 Hz, 4H), 7.77 (s, 2H), 8.17 (s, 2H), 8.42 (s, 2H).
13C[1H] NMR (150 MHz, CDCl3, rt): 11.9, 14.1, 18.7, 22.7, 29.4, 29.6, 29.66, 29.69, 29.73, 29.75, 29.8, 31.1, 31.9, 35.0, 119.1, 122.8, 125.5, 127.5, 131.5, 134.8, 136.2, 138.6, 143.2.
29Si[1H] NMR (119 MHz, CDCl3, rt): 2.16.
Anal. Calcd for C60H98S2Si2: C, 76.69; H, 10.51%. Found: C, 76.72; H, 10.69%.
アルゴンガス雰囲気下、50mLシュレンク管に10a(613mg, 0.65mmol, 1equiv)、TBAF(1M in THF)(6.5mL,6.5mmol, 10equiv)、脱水THF(26mL)を加え、室温で15時間撹拌した。水を加えることで反応を停止させ、クロロホルムで抽出した。飽和塩化ナトリウム水溶液で有機層を洗浄した後、無水硫酸マグネシウムで乾燥し、この混合溶液をろ過後、ロータリーエバポレーターを用いて溶媒を留去した。その後、シリカゲルカラムクロマトグラフィーで精製し、目的の化合物である3aを白色固体として89%(363mg, 0.58mmol) の収率で得た。以下に、シリカゲルカラムクロマトグラフィーの条件及び化合物3aの分析結果を示す。
シリカゲルカラムクロマトグラフィー (Rf = 0.52, hexane)
m.p.: 84-86℃
FT-IR (KBr, cm-1): 3039 (m), 3072 (s), 3043 (s), 2954 (w), 2914 (w), 2848 (w), 1577 (s), 1469 (w), 1344 (s), 1153 (m), 854 (w), 802 (w), 694 (w).
1H NMR (600 MHz, CDCl3, rt): 0.89 (t, J = 7.8 Hz, 6H), 1.22-1.35 (m, 28H), 1.41 (quin, J = 7.8 Hz, 4H), 1.51 (quin, J = 7.8 Hz, 4H), 1.87 (quin, J= 7.8 Hz, 4H), 3.17 (t, J = 7.8 Hz, 4H), 7.56 (d, J = 5.4 Hz, 2H), 7.60 (d, J = 5.4 Hz, 2H), 8.11 (s, 2H), 8.43 (s, 2H).
13C[1H] NMR (150 MHz, CDCl3, rt): 14.1, 22.7, 29.4, 29.6, 29.65, 29.69, 29.71, 29.8, 31.1, 31.9, 35.0, 119.2, 122.6, 123.0, 125.1, 125.7, 127.7, 136.6, 137.3, 139.0.
Anal. Calcd for C42H58S2: C, 80.45; H, 9.32%. Found: C, 80.51; H, 9.17%.
アルゴンガス雰囲気下、20mlシュレンク管に3a(188mg, 0.3mmol, 1equiv)、脱水THF(12mL)を加え、0℃に冷却した。その後、n-BuLi(1.6M in hexane)(0.56mL, 0.9mmol, 3equiv)を滴下した後、2時間還流させた。撹拌後、0℃に冷却し、Me3SnCl(239mg, 1.2mmol, 4equiv)を滴下した後、室温で12時間撹拌させた。水を加えることで反応を停止させ、ジクロロメタンで抽出した。飽和塩化ナトリウム水溶液で有機層を洗浄した後、無水硫酸マグネシウムで乾燥し、この混合溶液をろ過後、ロータリーエバポレーターを用いて溶媒を留去した。その後,高速液体クロマトグラフィーを2回用いて精製し、目的の化合物である4aを薄黄色液体として56%(159mg, 0.17mmol) の収率で得た。以下に、化合物4aの分析結果を示す。
FT-IR (KBr, cm-1): 2924 (w), 2852 (w), 1571 (s), 1465 (s), 1377 (s), 950 (s), 771 (m), 532 (m).
1H NMR (600 MHz, CDCl3, rt): 0.46 (t, J = 28.8 Hz, 18H), 0.88 (t, J = 7.2 Hz, 6H), 1.22-1.36 (m, 28H), 1.43 (quin, J = 7.8 Hz, 4H), 1.53 (quin, J = 7.8 Hz, 4H), 1.90 (quin, J = 7.8 Hz, 4H), 3.20 (t, J = 7.8 Hz, 4H), 7.65 (s, 2H), 8.15 (s, 2H), 8.40 (s, 2H).
13C[1H] NMR (150 MHz, CDCl3, rt): 8.16 (t, JC-Sn= 177 Hz), 14.1, 22.7, 29.4, 29.6, 29.67, 29.69, 29.72, 29.8, 31.0, 31.9, 35.0, 119.1, 122.8, 125.4, 127.2, 130.8, 136.0, 138.6, 138.8, 143.9.
Anal. Calcd for C48H74S2Sn2: C, 60.52; H, 7.83%. Found: C, 60.74; H, 7.96%.
5mLのバイアル管に、4a(62.7mg, 0.066mmol, 1equiv)、BTz-2T-HD(5a、59.7mg,0.066mmol, 1equiv)、Pd(PPh3)4(1.5mg, 1.32μmol, 2mol%)を加えた後、アルゴンガスを封入し、栓をして密閉した。その後、脱水トルエン(3.3mL)を加え、マイクロウェーブ照射装置を用いて、マイクロウェーブ照射下、180℃で40分撹拌した。その後、メタノール/塩酸(100mL/5 mL)を加え、室温で3時間撹拌した。フィルターに沈殿物を濾取し、ソックスレー抽出器を用いて、メタノール、ヘキサン、クロロホルムでそれぞれ3時間抽出した。クロロホルム成分をロータリーエバポレーターを用いて溶媒を留去し、減圧乾燥させることで、目的の化合物である化合物No.11を黒紫色固体として77%(69.7mg, 0.051mmol)の収率で得た。以下に、化合物No.11の分析結果を示す。
Anal. Calcd for C88H128N2S5: C, 76.91; H, 9.39; N, 2.04%. Found: C, 76.54; H, 9.26; N, 1.99%.
Mw/Mn=31443/21602(測定条件:140℃、o-DCB)
まず、実施例1のステップ1〜ステップ6と同様の方法で、化合物4bを合成した。5mlの反応容器に4b(56.1 mg, 0.059 mmol), 5b (55.5 mg, 0.059 mmol) 及び Pd(PPh3)4 (1.4 mg, 1.2 μmol) を加えた後、アルゴンガスを入れ、反応容器を密閉した。その後、トルエン (2.5 mL) を反応容器に加え、マイクロ波反応装置で180℃で40分間撹拌した。反応混合物を室温まで冷却した後、メタノール (100mL) と濃塩酸 (5mL) の混合溶液に加え、室温で3時間撹拌した。沈殿物をろ過した後、メタノール、ヘキサン、クロロホルム、クロロベンゼンの順にソックスレー抽出を行った。クロロホルム及びクロロベンゼンで抽出した溶液をそれぞれ濃縮し、メタノールを用いて再沈殿させた後、ろ過及び減圧下で乾燥させることでクロロホルムに可溶な目的の化合物である化合物No.16を金属光沢を有する紫色固体として37.9mg(46%)を得た。
以下に、化合物No.16の分析結果を示す。
GPC (o-DCB, 140℃): Mn = 30.6 kDa, PDI = 2.05 (CHCl3), Mn = 42.3 kDa, PDI = 1.82 (PhCl).
まず、実施例1のステップ1〜ステップ6と同様の方法で、化合物4bを合成した。5mLの反応容器に4b(60.0 mg、0.063 mmol)、5c(72.1 mg、 0.063 mmol) 及び Pd(PPh3)4 (1.5 mg、 1.2μmol)を加えた後、アルゴンガスを入れ、反応容器を密閉した。その後、トルエン (2.9 mL) を反応容器に加え、マイクロ波反応装置で180℃で 40 分間撹拌した。反応混合物を室温まで冷却した後、メタノール (100 mL) と濃塩酸 (5 mL) の混合溶液に注ぎ、室温で3 時間撹拌した。沈殿物をろ過した後、メタノール、ヘキサン、クロロホルムの順にソックスレー抽出を行った。クロロホルムで抽出した溶液をそれぞれ濃縮し、メタノールを用いて再沈殿させた後、ろ過及び減圧下で乾燥させることでクロロホルムに可溶な目的の化合物である化合物No.17を金属光沢を有する紫色固体として90.7mg(89%)を得た。
以下に、化合物No.17の分析結果を示す。
GPC (o-DCB, 140 ℃): Mn = 22.8 kDa, PDI = 1.39.
ITO基板(ジオマテック社、膜厚:150nm、抵抗率:<12Ω/□、透過率:(λ=550nm)≧85%)を中性洗剤、イオン交換水、アセトン及びイソプロパノールを用いてそれぞれ10分間超音波洗浄した。その後、基板の入ったイソプロパノールを10分間煮沸し、乾燥後、UV−オゾン洗浄を20分間行った。洗浄した基板上に、陽極バッファ層としてポリ(3、4-エチレン-ジオキシチオフェン):ポリ(スチレンスルホナート)(PEDOT:PSS、CleviousPVPAI4083)の水溶液を0.45μmのPVDF製シリンジフィルターを通じて滴下し、5000rpmで30秒間スピンコートした。120℃で10分間ホットプレート上で乾燥後、直ちにグローブボックス内に搬入した。濃度10g/Lの化合物No.16(実施例2で合成)の無水クロロベンゼン溶液に、重量比((A)/(B))=1:1〜1:2となるように可溶性フラーレン誘導体(PC61BM)を加え、100℃に保ったまま、400rpmで30秒、続いて1000rpmを5秒間スピンコートすることで(PEDOT:PSS)をコートした基板上に活性層を作製した。室温で乾燥後、真空蒸着装置に移し、3×10?5Pa程度の減圧下で陰極バッファ層として10nmのカルシウム、続いて陰極として80nmのアルミニウムをシャドーマスクを通じて真空蒸着することで、活性エリア0.16cm?2のバルクヘテロ接合型太陽電池素子を作製し、光電変換効率を測定した。光電変換効率は、得られたバルクヘテロ接合型太陽電池素子に対し、エアマス1.5G、100mW/cm2の疑似太陽光をITO電極側から照射することにより測定した。
また、比較例として、化合物No.16の代わりに化合物Aを用いる以外は、実施例4及び5と同様の手法で太陽電池素子を作製し、光電変換効率を測定した。これらの結果を表1に示す。
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 (5)
- 下記一般式(2)で表される構成単位を2以上、100以下有するピセン誘導体。
(式中、A1及びA2は、それぞれ独立に単環を表し、
R1、R2、R3、R4、R5及びR6は、それぞれ独立に水素原子、ハロゲン原子、シアノ基、ニトロ基、水酸基、カルボキシル基、チオール基、−SiR7R8R9、−NR10R11基、又は置換基を有している若しくは無置換の炭化水素基を表し、
R1、R2、R3、R4、R5及びR6の少なくとも一つは水素原子では無く、
R7、R8、R9、R10又はR11はそれぞれ独立に水素原子又は置換基を有している若しくは無置換の炭化水素基を表し、
Y 1 及びY 2 は単結合又は下記(Y−1)〜(Y−8)から選ばれる基を1〜5個組み合わせて連結した基であり、
Z 1 は、単結合又は下記(Z−1)〜(Z−21)から選ばれる基を表し、
nは1以上1000以下の整数を表す。)
(式中、X 1 及びX 4 はS、O又はNR 12 を表し、
kは1〜4の整数を表し、
R 12 は置換されている若しくは無置換の炭化水素基を表し、
(Y−1)〜(Y−4)及び(Y−6)〜(Y−8)で表される基中の水素原子は、ハロゲン原子、シアノ基、ニトロ基、水酸基、カルボキシル基、チオール基、−NR 13 R 14 基、置換されている若しくは無置換の炭化水素基又は置換されている若しくは無置換の複素環基で置換されていてもよく、
R 13 及びR 14 は、置換されている若しくは無置換の炭化水素基を表す。)
(式中、X 2 はS又はNR 15 を表し、
X 3 はS、NR 15 、CR 16 R 17 又はSiR 16 R 17 を表し、
X 5 はS、O又はNR 15 を表し、
R 15 、R 16 及びR 17 は、置換されている若しくは無置換の炭化水素基を表し、
(Z−1)〜(Z−21)で表される基中の水素原子は、ハロゲン原子、シアノ基、ニトロ基、水酸基、カルボキシル基、チオール基、−NR 18 R 19 基、置換されている若しくは無置換の炭化水素基又は置換されている若しくは無置換の複素環基で置換されていてもよく、
R 18 及びR 19 は、置換されている若しくは無置換の炭化水素基を表す。) - (A)p型有機半導体材料として請求項1に記載のピセン誘導体、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2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3に記載の光電変換層を有してなる光電変換素子。
- 請求項4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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