JP2019532146A - 重合体およびこれを含む有機太陽電池 - Google Patents
重合体およびこれを含む有機太陽電池 Download PDFInfo
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- JP2019532146A JP2019532146A JP2019516941A JP2019516941A JP2019532146A JP 2019532146 A JP2019532146 A JP 2019532146A JP 2019516941 A JP2019516941 A JP 2019516941A JP 2019516941 A JP2019516941 A JP 2019516941A JP 2019532146 A JP2019532146 A JP 2019532146A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 111
- 239000000126 substance Substances 0.000 claims description 172
- 239000010410 layer Substances 0.000 claims description 77
- -1 GeRR ′ Inorganic materials 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 239000011737 fluorine Substances 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
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- 0 CC(C)(C)c(c1n[s]nc1c(-c1c(C)c(C)c(-c2c(C)c(C)c(C)[s]2)[s]1)c1O*)c1O* Chemical compound CC(C)(C)c(c1n[s]nc1c(-c1c(C)c(C)c(-c2c(C)c(C)c(C)[s]2)[s]1)c1O*)c1O* 0.000 description 4
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- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 2
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 2
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
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- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
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- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
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- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
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- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
[化学式1]
d1、d2、xおよびx'は、それぞれ1または2であり、
前記d1、d2、xおよびx'がそれぞれ2の場合、括弧内の構造は、互いに同一または異なり、
X1およびX2は、互いに同一または異なり、それぞれ独立に、CRR'、NR、O、SiRR'、PR、S、GeRR'、Se、またはTeであり、
Y1〜Y4は、互いに同一または異なり、それぞれ独立に、CR"、N、SiR"、P、またはGeR"であり、
XおよびX'は、互いに同一または異なり、それぞれ独立に、SまたはSeであり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の直鎖もしくは分枝鎖のアルキル基であり、
R1およびR2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の分枝鎖のアルキル基であり、
G1およびG2は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R、R'およびR"は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
D1およびD2は、互いに同一または異なり、それぞれ独立に、下記構造の中から選択されるいずれか1つであり、
X"、X"'およびX""は、互いに同一または異なり、それぞれ独立に、SまたはSeであり、
YおよびY'は、互いに同一または異なり、それぞれ独立に、CR"'、N、SiR"'、P、またはGeR"'であり、
G11〜G18、G101およびG102は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R"'は、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
gは、0または1である。
[化学式1−1]
Ar1、Ar2およびD1は、前記化学式1で定義したものと同じである。
X"、X"'およびX""は、互いに同一または異なり、それぞれ独立に、SまたはSeであり、
YおよびY'は、互いに同一または異なり、それぞれ独立に、CR"'、N、SiR"'、P、またはGeR"'であり、
G11〜G18、G101およびG102は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R"'は、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
gは、0または1である。
[化学式1−2]
Ar1およびAr2は、前記化学式1で定義したものと同じであり、
G11〜G18、G101およびG102は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R"'は、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基である。
[化学式2−1]
R1、R2、G1、G2およびD2は、化学式2で定義したものと同じである。
X"、X"'およびX""は、互いに同一または異なり、それぞれ独立に、SまたはSeであり、
YおよびY'は、互いに同一または異なり、それぞれ独立に、CR"'、N、SiR"'、P、またはGeR"'であり、
G11〜G18、G101およびG102は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R"'は、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
gは、0または1である。
[化学式2−2]
R1、R2、G1およびG2は、化学式2で定義したものと同じであり、
G11〜G18、G101およびG102は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R"'は、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基である。
[化学式4]
Aは、前記化学式1で表される第1単位であり、
Bは、前記化学式2で表される第2単位であり、
lは、モル分率であって0<l<1であり、
mは、モル分率であって0<m<1であり、
l+m=1であり、
nは、単位の繰り返し数であって1〜10,000の整数である。
[化学式4−1]
Ar1およびAr2は、前記化学式1で定義したものと同じであり、
R1、R2、G1およびG2は、前記化学式2で定義したものと同じであり、
G11〜G18、G101およびG102は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R"'は、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
lは、モル分率であって0<l<1であり、
mは、モル分率であって0<m<1であり、
l+m=1であり、
nは、単位の繰り返し数であって1〜10,000の整数である。
[化学式5−1−1]
lは、モル分率であって0<l<1であり、
mは、モル分率であって0<m<1であり、
l+m=1であり、
nは、単位の繰り返し数であって1〜10,000の整数である。
HOMO(or LUMO)(eV)=−4.8−(Eonset−E1/2(Ferrocene))
前記重合体1とPC71BMとを1:1でクロロベンゼン(Chlorobenzene、CB)に溶かして複合溶液(composit solution)を製造した。この時、濃度は4wt%に調節し、有機太陽電池はITO/ZnO NP/光活性層/MoO3/Agのインバーテッド構造にした。
前記実験例1−1において、光活性層のコーティングのために、重合体1とPC71BMとの複合溶液を700rpmの代わりに1000rpmでスピンコーティングしたことを除き、実験例1−1と同様の方法で有機太陽電池を製造した。
前記実験例1−1において、光活性層のコーティングのために、重合体1とPC71BMとの複合溶液を700rpmの代わりに1500rpmでスピンコーティングしたことを除き、実験例1−1と同様の方法で有機太陽電池を製造した。
前記実験例1−1において、光活性層のコーティングのために、重合体1とPC71BMとの複合溶液を700rpmの代わりに2000rpmでスピンコーティングしたことを除き、実験例1−1と同様の方法で有機太陽電池を製造した。
前記重合体1とPC71BMとを1:2でクロロベンゼン(Chlorobenzene、CB)に溶かして複合溶液(composit solution)を製造した。この時、濃度は4wt%に調節し、有機太陽電池はITO/ZnO NP/光活性層/MoO3/Agのインバーテッド構造にした。
前記実験例2−1において、光活性層のコーティングのために、重合体1とPC71BMとの複合溶液を700rpmの代わりに1000rpmでスピンコーティングしたことを除き、実験例2−1と同様の方法で有機太陽電池を製造した。
前記実験例2−1において、光活性層のコーティングのために、重合体1とPC71BMとの複合溶液を700rpmの代わりに1500rpmでスピンコーティングしたことを除き、実験例2−1と同様の方法で有機太陽電池を製造した。
前記実験例2−1において、光活性層のコーティングのために、重合体1とPC71BMとの複合溶液を700rpmの代わりに2000rpmでスピンコーティングしたことを除き、実験例2−1と同様の方法で有機太陽電池を製造した。
前記実験例1−1において、前記重合体1とPC71BMとを1:1の代わりに1:3でクロロベンゼン(Chlorobenzene、CB)に溶かして複合溶液(composit solution)を製造したことを除き、実験例1−1と同様の方法で有機太陽電池を製造した。
前記実験例1−2において、前記重合体1とPC71BMとを1:1の代わりに1:3でクロロベンゼン(Chlorobenzene、CB)に溶かして複合溶液(composit solution)を製造したことを除き、実験例1−2と同様の方法で有機太陽電池を製造した。
前記実験例1−3において、前記重合体1とPC71BMとを1:1の代わりに1:3でクロロベンゼン(Chlorobenzene、CB)に溶かして複合溶液(composit solution)を製造したことを除き、実験例1−3と同様の方法で有機太陽電池を製造した。
前記実験例1−4において、前記重合体1とPC71BMをと1:1の代わりに1:3でクロロベンゼン(Chlorobenzene、CB)に溶かして複合溶液(composit solution)を製造したことを除き、実験例1−4と同様の方法で有機太陽電池を製造した。
前記実験例2−1において、前記重合体1とPC71BMとの複合溶液(composit solution)を4wt%の代わりに2wt%で製造したことを除き、実験例2−1と同様の方法で有機太陽電池を製造した。
前記実験例2−2において、前記重合体1とPC71BMとの複合溶液(composit solution)を4wt%の代わりに2wt%で製造したことを除き、実験例2−2と同様の方法で有機太陽電池を製造した。
前記実験例2−3において、前記重合体1とPC71BMとの複合溶液(composit solution)を4wt%の代わりに2wt%で製造したことを除き、実験例2−3と同様の方法で有機太陽電池を製造した。
前記実験例2−4において、前記重合体1とPC71BMとの複合溶液(composit solution)を4wt%の代わりに2wt%で製造したことを除き、実験例2−4と同様の方法で有機太陽電池を製造した。
前記実験例2−1において、重合体1とPC71BMとの複合溶液に1,8−ジヨードオクタン(DIO:1,8−diiodooctane)を3vol%添加したことを除き、実験例2−1と同様の方法で有機太陽電池を製造した。
前記実験例2−2において、重合体1とPC71BMとの複合溶液に1,8−ジヨードオクタン(DIO:1,8−diiodooctane)を3vol%添加したことを除き、実験例2−2と同様の方法で有機太陽電池を製造した。
前記実験例2−3において、重合体1とPC71BMとの複合溶液に1,8−ジヨードオクタン(DIO:1,8−diiodooctane)を3vol%添加したことを除き、実験例2−3と同様の方法で有機太陽電池を製造した。
前記実験例2−4において、重合体1とPC71BMとの複合溶液に1,8−ジヨードオクタン(DIO:1,8−diiodooctane)を3vol%添加したことを除き、実験例2−4と同様の方法で有機太陽電池を製造した。
前記実験例2−1において、重合体1とPC71BMとの複合溶液にジフェニルエーテル(DPE:diphenylether)を3vol%添加したことを除き、実験例2−1と同様の方法で有機太陽電池を製造した。
前記実験例2−2において、重合体1とPC71BMとの複合溶液にジフェニルエーテル(DPE:diphenylether)を3vol%添加したことを除き、実験例2−2と同様の方法で有機太陽電池を製造した。
前記実験例2−3において、重合体1とPC71BMとの複合溶液にジフェニルエーテル(DPE:diphenylether)を3vol%添加したことを除き、実験例2−3と同様の方法で有機太陽電池を製造した。
前記実験例2−4において、重合体1とPC71BMとの複合溶液にジフェニルエーテル(DPE:diphenylether)を3vol%添加したことを除き、実験例2−4と同様の方法で有機太陽電池を製造した。
前記実験例2−1において、重合体1とPC71BMとの複合溶液に1−クロロナフタレン(1−CN:1−chloronaphthalene)を3vol%添加したことを除き、実験例2−1と同様の方法で有機太陽電池を製造した。
前記実験例2−2において、重合体1とPC71BMとの複合溶液に1−クロロナフタレン(1−CN:1−chloronaphthalene)を3vol%添加したことを除き、実験例2−2と同様の方法で有機太陽電池を製造した。
前記実験例2−3において、重合体1とPC71BMとの複合溶液に1−クロロナフタレン(1−CN:1−chloronaphthalene)を3vol%添加したことを除き、実験例2−3と同様の方法で有機太陽電池を製造した。
前記実験例2−4において、重合体1とPC71BMとの複合溶液に1−クロロナフタレン(1−CN:1−chloronaphthalene)を3vol%添加したことを除き、実験例2−4と同様の方法で有機太陽電池を製造した。
102:第1電極
103:正孔輸送層
104:光活性層
105:第2電極
Claims (16)
- 下記化学式1で表される第1単位;および
下記化学式2で表される第2単位を含む重合体:
[化学式1]
d1、d2、xおよびx'は、それぞれ1または2であり、
前記d1、d2、xおよびx'がそれぞれ2の場合、括弧内の構造は、互いに同一または異なり、
X1およびX2は、互いに同一または異なり、それぞれ独立に、CRR'、NR、O、SiRR'、PR、S、GeRR'、Se、またはTeであり、
Y1〜Y4は、互いに同一または異なり、それぞれ独立に、CR"、N、SiR"、P、またはGeR"であり、
XおよびX'は、互いに同一または異なり、それぞれ独立に、SまたはSeであり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の直鎖もしくは分枝鎖のアルキル基であり、
R1およびR2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の分枝鎖のアルキル基であり、
G1およびG2は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R、R'およびR"は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
D1およびD2は、互いに同一または異なり、それぞれ独立に、下記構造の中から選択されるいずれか1つであり、
X"、X"'およびX""は、互いに同一または異なり、それぞれ独立に、SまたはSeであり、
YおよびY'は、互いに同一または異なり、それぞれ独立に、CR"'、N、SiR"'、P、またはGeR"'であり、
G11〜G18、G101およびG102は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R"'は、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
gは、0または1である。 - 前記化学式1で表される第1単位は、下記化学式1−2〜1−5のうちのいずれか1つで表されるものである、請求項1に記載の重合体:
[化学式1−2]
Ar1およびAr2は、前記化学式1で定義したものと同じであり、
G11〜G18、G101およびG102は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R"'は、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基である。 - 前記化学式2で表される第2単位は、下記化学式2−2〜2−5のうちのいずれか1つで表されるものである、請求項1に記載の重合体:
[化学式2−2]
R1、R2、G1およびG2は、前記化学式2で定義したものと同じであり、
G11〜G18、G101およびG102は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R"'は、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基である。 - 前記重合体は、下記化学式4−1〜4−16および5−1〜5−16のうちのいずれか1つで表される単位を含むものである、請求項1に記載の重合体:
[化学式4−1]
Ar1およびAr2は、前記化学式1で定義したものと同じであり、
R1、R2、G1およびG2は、前記化学式2で定義したものと同じであり、
G11〜G18、G101およびG102は、互いに同一または異なり、それぞれ独立に、水素;またはフッ素であり、
R"'は、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
lは、モル分率であって0<l<1であり、
mは、モル分率であって0<m<1であり、
l+m=1であり、
nは、単位の繰り返し数であって1〜10,000の整数である。 - 前記重合体のHOMOエネルギー準位は、5eV〜5.9eVである、請求項1から8のいずれか一項に記載の重合体。
- 前記重合体の数平均分子量は、5,000g/mol〜1,000,000g/molである、請求項1から9のいずれか一項に記載の重合体。
- 前記重合体の分子量分布は、1〜10である、請求項1から10のいずれか一項に記載の重合体。
- 第1電極と、前記第1電極に対向して備えられる第2電極と、前記第1電極と前記第2電極との間に備えられ、光活性層を含む1層以上の有機物層とを含み、前記有機物層のうちの1層以上は、請求項1から11のいずれか一項に記載の重合体を含むものである有機太陽電池。
- 前記光活性層は、電子供与体および電子受容体からなる群より選択される1以上を含み、
前記電子供与体は、前記重合体を含むものである、請求項12に記載の有機太陽電池。 - 前記電子供与体および電子受容体は、バルクヘテロジャンクション(BHJ)を構成するものである、請求項13に記載の有機太陽電池。
- 前記光活性層は、添加剤をさらに含むものである、請求項13または14に記載の有機太陽電池。
- 前記光活性層は、n型有機物層およびp型有機物層を含む二層薄膜(bilayer)構造であり、
前記p型有機物層は、前記重合体を含むものである、請求項12から15のいずれか一項に記載の有機太陽電池。
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004339516A (ja) * | 2003-05-16 | 2004-12-02 | Merck Patent Gmbh | フルオレンおよびアリール基を含むモノマー、オリゴマーおよびポリマー |
JP2011246503A (ja) * | 2010-05-21 | 2011-12-08 | Jsr Corp | 新規重合体及びその中間体 |
JP2015046639A (ja) * | 2010-10-22 | 2015-03-12 | レイナジー テック インコーポレイテッド | 共役ポリマーおよび光電子デバイスにおけるその使用 |
WO2015100441A1 (en) * | 2013-12-26 | 2015-07-02 | Raynergy Tek Incorporation | Conjugated polymers and devices incorporating the same |
KR20160110199A (ko) * | 2015-03-09 | 2016-09-21 | 주식회사 엘지화학 | 중합체 및 이를 포함하는 유기 태양 전지 |
JP2016531171A (ja) * | 2013-07-15 | 2016-10-06 | エルジー・ケム・リミテッド | 共重合体およびこれを含む有機太陽電池 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102574991B (zh) | 2009-08-28 | 2014-04-23 | 新加坡科技研究局 | 聚合物半导体、装置及相关方法 |
KR101099601B1 (ko) | 2011-01-13 | 2011-12-29 | 한국화학연구원 | 디티에노티오펜 화합물이 도입된 전도성 고분자 및 그를 광전변환재료로 이용한 유기 태양전지 |
WO2013010615A1 (en) | 2011-07-21 | 2013-01-24 | Merck Patent Gmbh | Conjugated polymers |
KR20130090736A (ko) | 2012-02-06 | 2013-08-14 | 주식회사 엘지화학 | 헤테로 방향족 화합물 및 이를 포함하는 유기 태양전지 |
TWI635111B (zh) | 2012-03-16 | 2018-09-11 | 馬克專利公司 | 共軛聚合物 |
KR101595147B1 (ko) | 2012-08-20 | 2016-02-18 | 주식회사 엘지화학 | 방향족 화합물 및 이를 포함하는 유기 태양전지 |
KR101707028B1 (ko) * | 2014-09-15 | 2017-02-16 | 한국화학연구원 | 신규한 벤조티아디아졸기를 포함한 유기 반도체 화합물, 이의 제조방법 및 이를 채용한 유기 반도체 소자 |
JP2017534621A (ja) * | 2014-10-22 | 2017-11-24 | ザ・ホンコン・ユニバーシティー・オブ・サイエンス・アンド・テクノロジーThe Hong Kong University of Science & Technology | 電子工学的及びフォトニック用途のためのジフルオロビチオフェン系ドナー−アクセプター型ポリマー |
KR101736556B1 (ko) * | 2014-12-24 | 2017-05-16 | 주식회사 엘지화학 | 유-무기 하이브리드 태양 전지 |
KR101807870B1 (ko) | 2015-01-20 | 2017-12-12 | 한국화학연구원 | 신규한 유기반도체 화합물 및 이를 이용한 유기 전자 소자 |
-
2017
- 2017-03-06 KR KR1020170028258A patent/KR102074556B1/ko active IP Right Grant
- 2017-12-13 CN CN201780065912.9A patent/CN109863188A/zh active Pending
- 2017-12-13 EP EP17900222.5A patent/EP3511357B1/en active Active
- 2017-12-13 WO PCT/KR2017/014608 patent/WO2018164353A1/ko unknown
- 2017-12-13 JP JP2019516941A patent/JP6805461B2/ja active Active
- 2017-12-13 US US16/339,665 patent/US10629816B2/en active Active
- 2017-12-27 TW TW106145985A patent/TWI669323B/zh active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004339516A (ja) * | 2003-05-16 | 2004-12-02 | Merck Patent Gmbh | フルオレンおよびアリール基を含むモノマー、オリゴマーおよびポリマー |
JP2011246503A (ja) * | 2010-05-21 | 2011-12-08 | Jsr Corp | 新規重合体及びその中間体 |
JP2015046639A (ja) * | 2010-10-22 | 2015-03-12 | レイナジー テック インコーポレイテッド | 共役ポリマーおよび光電子デバイスにおけるその使用 |
JP2016531171A (ja) * | 2013-07-15 | 2016-10-06 | エルジー・ケム・リミテッド | 共重合体およびこれを含む有機太陽電池 |
WO2015100441A1 (en) * | 2013-12-26 | 2015-07-02 | Raynergy Tek Incorporation | Conjugated polymers and devices incorporating the same |
KR20160110199A (ko) * | 2015-03-09 | 2016-09-21 | 주식회사 엘지화학 | 중합체 및 이를 포함하는 유기 태양 전지 |
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EP3511357A4 (en) | 2019-10-23 |
EP3511357B1 (en) | 2024-04-03 |
TWI669323B (zh) | 2019-08-21 |
CN109863188A (zh) | 2019-06-07 |
EP3511357A1 (en) | 2019-07-17 |
TW201833171A (zh) | 2018-09-16 |
US10629816B2 (en) | 2020-04-21 |
WO2018164353A1 (ko) | 2018-09-13 |
US20190378987A1 (en) | 2019-12-12 |
KR102074556B1 (ko) | 2020-02-06 |
JP6805461B2 (ja) | 2020-12-23 |
KR20180101827A (ko) | 2018-09-14 |
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