JP6969725B2 - 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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- JP6969725B2 JP6969725B2 JP2019542549A JP2019542549A JP6969725B2 JP 6969725 B2 JP6969725 B2 JP 6969725B2 JP 2019542549 A JP2019542549 A JP 2019542549A JP 2019542549 A JP2019542549 A JP 2019542549A JP 6969725 B2 JP6969725 B2 JP 6969725B2
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- 229920000642 polymer Polymers 0.000 title claims description 158
- 239000000126 substance Substances 0.000 claims description 267
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- 239000010410 layer Substances 0.000 claims description 57
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 229910003472 fullerene Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
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- 125000004432 carbon atom Chemical group C* 0.000 description 39
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- NWVZZUBZUJKJNG-UHFFFAOYSA-N [4,8-bis[5-(2-ethylhexylsulfanyl)thiophen-2-yl]-2-trimethylstannylthieno[2,3-f][1]benzothiol-6-yl]-trimethylstannane Chemical compound CCCCC(CC)CSc1ccc(s1)-c1c2cc(sc2c(-c2ccc(SCC(CC)CCCC)s2)c2cc(sc12)[Sn](C)(C)C)[Sn](C)(C)C NWVZZUBZUJKJNG-UHFFFAOYSA-N 0.000 description 5
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- 238000007740 vapor deposition Methods 0.000 description 4
- HETICFAGRUKZDA-UHFFFAOYSA-N 1,3-bis(5-bromothiophen-2-yl)-5,7-bis(2-ethylhexyl)thieno[3,4-f][2]benzothiole-4,8-dione Chemical compound CCCCC(CC)Cc1sc(CC(CC)CCCC)c2c1C(=O)c1c(sc(-c3ccc(Br)s3)c1C2=O)-c1ccc(Br)s1 HETICFAGRUKZDA-UHFFFAOYSA-N 0.000 description 3
- 0 Cc1c(*)c(c(*)c2[s]c(C)c(*)c2c2*)c2[s]1 Chemical compound Cc1c(*)c(c(*)c2[s]c(C)c(*)c2c2*)c2[s]1 0.000 description 3
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- OCFFMJYHZKHRKM-UHFFFAOYSA-N [4,8-bis[5-(2-ethylhexyl)thiophen-2-yl]-2-trimethylstannylthieno[2,3-f][1]benzothiol-6-yl]-trimethylstannane Chemical compound S1C(CC(CC)CCCC)=CC=C1C(C=1SC(=CC=11)[Sn](C)(C)C)=C(C=C(S2)[Sn](C)(C)C)C2=C1C1=CC=C(CC(CC)CCCC)S1 OCFFMJYHZKHRKM-UHFFFAOYSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 239000011787 zinc oxide Substances 0.000 description 3
- KZDTZHQLABJVLE-UHFFFAOYSA-N 1,8-diiodooctane Chemical group ICCCCCCCCI KZDTZHQLABJVLE-UHFFFAOYSA-N 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 2
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical group BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
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- 238000007334 copolymerization reaction Methods 0.000 description 2
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
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- 150000004706 metal oxides Chemical class 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910000480 nickel oxide Inorganic materials 0.000 description 2
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
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- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical group FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-UHFFFAOYSA-N 0.000 description 1
- 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
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- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- AVPWUAFYDNQGNZ-UHFFFAOYSA-N 2,3,4,5-tetrabromothiophene Chemical compound BrC=1SC(Br)=C(Br)C=1Br AVPWUAFYDNQGNZ-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- JAEGDDGOGVSXLM-UHFFFAOYSA-N [4,8-bis[5-(2-ethylhexyl)-4-fluorothiophen-2-yl]-2-trimethylstannylthieno[2,3-f][1]benzothiol-6-yl]-trimethylstannane Chemical compound CCCCC(CC)Cc1sc(cc1F)-c1c2cc(sc2c(-c2cc(F)c(CC(CC)CCCC)s2)c2cc(sc12)[Sn](C)(C)C)[Sn](C)(C)C JAEGDDGOGVSXLM-UHFFFAOYSA-N 0.000 description 1
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- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Description
下記化学式1で表される第1単位と、
下記化学式2で表される第2単位と、
下記化学式3または4で表される第3単位とを含む重合体を提供する。
[化学式1]
R1〜R14は、互いに同一または異なり、それぞれ水素;置換もしくは非置換のアルキル基;カルボキシル基;またはエステル基(−COOR')であり、
Eは、SまたはNR"であり、
R'およびR"は、互いに同一または異なり、それぞれ置換もしくは非置換のアルキル基であり、
A1およびA2は、互いに同一または異なり、それぞれ水素;ハロゲン基;置換もしくは非置換のアルキル基;または置換もしくは非置換のアルコキシ基であり、
a〜fは、それぞれ0または1であり、
Y1〜Y4は、互いに同一または異なり、それぞれ下記化学式5で表されるものであり、
[化学式5]
Lは、直接結合、SまたはOであり、
Raは、置換もしくは非置換のアルキル基であり、
RbおよびRcは、互いに同一または異なり、それぞれ水素;ハロゲン基;または置換もしくは非置換のアルキル基であり、
前記化学式1と化学式2は、互いに異なる構造を有するものであり、
前記化学式1〜5において、
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、
前記光活性層は、電子供与体および電子受容体を含み、
前記電子供与体は、前記重合体を含み、前記電子受容体は、非フラーレン(non−fullerene)系化合物を含むものである有機太陽電池を提供する。
[化学式6]
Qは、互いに同一または異なり、それぞれ前記化学式3または4で表される単位であり、
lおよびmは、モル分率を示し、
0<l<1であり、
0<m<1であり、
0<l+m≦1であり、
k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6−1]
Rdは、置換もしくは非置換のアルキル基であり、前記Raとは異なるものである。
[化学式7−1]
Rdは、置換もしくは非置換のアルキル基であり、前記Raとは異なるものである。
[化学式8]
Rdは、置換もしくは非置換のアルキル基であり、前記Raとは異なるものである。
[化学式20]
Rdは、置換もしくは非置換のアルキル基であり、前記Raとは異なるものである。
[化学式A]
X1〜X6は、互いに同一または異なり、それぞれ独立に、水素;または置換もしくは非置換のアルキル基であり、
Z1〜Z4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アリーレン基;または置換もしくは非置換の2価のヘテロ環基であり、
MaおよびMbは、互いに同一または異なり、それぞれ独立に、水素;ハロゲン基;または置換もしくは非置換のアルキル基であり、
pおよびqは、互いに同一または異なり、それぞれ独立に、0〜2の整数であり、
pまたはqが2の場合、括弧内の構造は、互いに同一である。
[化学式A−1]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−(2−エチルヘキシル)チオフェン−2−yl)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−(2−ethylhexyl)thiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))117.9mg(0.5eq)、(4,8−ビス(5−((2−エチルヘキシル)チオ)チオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−((2−ethylhexyl)thio)thiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))126.31mg(0.5eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル)−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)200mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入した後、トルエン16mLおよびジメチルホルムアミド(Dimethylformamide、DMF)1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体1)を精製した。
[重合体1]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−(2−エチルヘキシル)チオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−(2−ethylhexyl)thiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))117.9mg(0.5eq)、(4,8−ビス(5−(2−エチルヘキシル)−4−フルオロチオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−(2−ethylhexyl)−4−fluorothiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))122.64mg(0.5eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル)−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)200mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入した後、トルエン16mLおよびDMF1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体2)を精製した。
[重合体2]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−(2−エチルヘキシル)チオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−(2−ethylhexyl)thiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))117.9mg(0.5eq)、4,8−ビス(5−(オクチル)チオフェン−2−イル)ジチエノベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)(4,8−bis(5−(octyl)thiophen−2−yl)dithienobenzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))132.58mg(0.5eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル)−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)200mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入後、トルエン16mLおよびDMF1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体3)を精製した。
[重合体3]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−(2−エチルヘキシル)チオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−(2−ethylhexyl)thiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))117.9mg(0.5eq)、4,8−ビス(5−((オクチル)チオ)チオフェン−2−イル)ジチエノベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)(4,8−bis(5−((octyl)thio)thiophen−2−yl)dithienobenzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))140.94mg(0.5eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル)−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)200mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入した後、トルエン16mLおよびDMF1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体4)を精製した。
[重合体4]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−((2−エチルヘキシル)チオ)チオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−((2−ethylhexyl)thio)thiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))126.31mg(0.5eq)、(4,8−ビス(5−(2−エチルヘキシル)−4−フルオロチオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−(2−ethylhexyl)−4−fluorothiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))122.64mg(0.5eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル)−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)200mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入した後、トルエン16mLおよびDMF1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体5)を精製した。
[重合体5]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−((2−エチルヘキシル)チオ)チオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−((2−ethylhexyl)thio)thiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))126.31mg(0.5eq)、4,8−ビス(5−(オクチル)チオフェン−2−イル)ジチエノベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)(4,8−bis(5−(octyl)thiophen−2−yl)dithienobenzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))132.58mg(0.5eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル)−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)200mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入した後、トルエン16mLおよびDMF1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体6)を精製した。
[重合体6]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−((2−エチルヘキシル)チオ)チオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−((2−ethylhexyl)thio)thiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))126.31mg(0.5eq)、4,8−ビス(5−((オクチル)チオ)チオフェン−2−イル)ジチエノベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)(4,8−bis(5−((octyl)thio)thiophen−2−yl)dithienobenzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))140.94mg(0.5eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)200mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入した後、トルエン16mLおよびDMF1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体7)を精製した。
[重合体7]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−(2−エチルヘキシル)−4−フルオロチオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−(2−ethylhexyl)−4−fluorothiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))122.64mg(0.5eq)、4,8−ビス(5−(オクチル)チオフェン−2−イル)ジチエノベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)(4,8−bis(5−(octyl)thiophen−2−yl)dithienobenzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))132.58mg(0.5eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル)−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)200mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入した後、トルエン16mLおよびDMF1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体8)を精製した。
[重合体8]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−(2−エチルヘキシル)−4−フルオロチオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−(2−ethylhexyl)−4−fluorothiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))122.64mg(0.5eq)、4,8−ビス(5−((オクチル)チオ)チオフェン−2−イル)ジチエノベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)(4,8−bis(5−((octyl)thio)thiophen−2−yl)dithienobenzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))140.94mg(0.5eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル)−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)200mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入した後、トルエン16mLおよびDMF1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体9)を精製した。
[重合体9]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−(2−エチルヘキシル)チオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−(2−ethylhexyl)thiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))321mg(1.0eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル)−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)272.08mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入した後、トルエン16mLおよびDMF1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体10)を精製した。
[重合体10]
コンデンサ付きの丸いフラスコに、(4,8−ビス(5−((2−エチルヘキシル)チオ)チオフェン−2−イル)ベンゾ[1,2−b:4,5−b']ジチオフェン−2,6−ジイル)ビス(トリメチルスタンナン)((4,8−bis(5−((2−ethylhexyl)thio)thiophen−2−yl)benzo[1,2−b:4,5−b']dithiophene−2,6−diyl)bis(trimethylstannane))133mg(1.0eq)、1,3−ビス(5−ブロモチオフェン−2−イル)−5,7−ビス(2−エチルヘキシル)−4H,8H−ベンゾ[1,2−c:4,5−c']ジチオフェン−4,8−ジオン(1,3−bis(5−bromothiophen−2−yl)−5,7−bis(2−ethylhexyl)−4H,8H−benzo[1,2−c:4,5−c']dithiophene−4,8−dione)105.2mg(1.0eq)、およびPd(PPh3)4 0.01g(0.03eq)を注入した後、トルエン16mLおよびDMF1mLを注入した。この後、100℃で17時間還流させ、メタノールにより反応を終了した後、メタノール、ヘキサン、およびアセトンにより合成された高分子(下記の重合体11)を精製した。
[重合体11]
前記重合体1と140℃でアニーリング(annealing)した下記化学式A−1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2wt%に調節し、前記複合溶液に1,8−ジヨードオクタン(DIO:1,8−diiodooctane)0.5vol%を添加した。
[化学式A−1]
ITOが1.5×1.5cm2のバータイプ(bar type)でコーティングされたガラス基板(11.5Ω/□)を蒸留水、アセトン、および2−プロパノールを用いて超音波洗浄し、ITO表面を10分間オゾン処理して第1電極を形成した。
前記実施例1における前記重合体1の代わりに前記重合体2を用いたことを除けば、実施例1と同様の過程で有機太陽電池を製造した。
前記実施例1における前記重合体1の代わりに前記重合体3を用いたことを除けば、実施例1と同様の過程で有機太陽電池を製造した。
前記実施例1における前記重合体1の代わりに前記重合体4を用いたことを除けば、実施例1と同様の過程で有機太陽電池を製造した。
前記実施例1における前記重合体1の代わりに前記重合体5を用いたことを除けば、実施例1と同様の過程で有機太陽電池を製造した。
前記実施例1における前記重合体1の代わりに前記重合体6を用いたことを除けば、実施例1と同様の過程で有機太陽電池を製造した。
前記実施例1における前記重合体1の代わりに前記重合体7を用いたことを除けば、実施例1と同様の過程で有機太陽電池を製造した。
前記実施例1における前記重合体1の代わりに前記重合体8を用いたことを除けば、実施例1と同様の過程で有機太陽電池を製造した。
前記実施例1における前記重合体1の代わりに前記重合体9を用いたことを除けば、実施例1と同様の過程で有機太陽電池を製造した。
前記実施例1における前記重合体1の代わりに前記重合体10を用いたことを除けば、実施例1と同様の過程で有機太陽電池を製造した。
前記実施例1における前記重合体1の代わりに前記重合体11を用いたことを除けば、実施例1と同様の過程で有機太陽電池を製造した。
102:電子輸送層
103:光活性層
104:正孔輸送層
105:第2電極
Claims (11)
- 下記化学式6−1から6−3、6−5、6−6、および7−1から7−9のいずれかで表される単位を含む重合体:
[化学式6−1]
R1〜R 4 は、互いに同一または異なり、それぞれ水素;置換もしくは非置換のアルキル基;カルボキシル基;またはエステル基(−COOR')であり、
R'は、置換もしくは非置換のアルキル基であり、
Raは、置換もしくは非置換のアルキル基であり、
Rdは、置換もしくは非置換のアルキル基であり、前記Raとは異なるものであり、
Qは、互いに同一または異なり、それぞれ下記化学式3または4で表される単位であり、
lおよびmは、モル分率を示し、
0<l<1であり、
0<m<1であり、
0<l+m≦1であり、
kは、単位の繰り返し数であって、1〜10,000の整数であり、
[化学式3]
R 5 〜R 14 は、互いに同一または異なり、それぞれ水素;置換もしくは非置換のアルキル基;カルボキシル基;またはエステル基(−COOR')であり、
Eは、SまたはNR"であり、
R'およびR"は、互いに同一または異なり、それぞれ置換もしくは非置換のアルキル基であり、
A 1 およびA 2 は、互いに同一または異なり、それぞれ水素;ハロゲン基;置換もしくは非置換のアルキル基;または置換もしくは非置換のアルコキシ基であり、
c〜fは、それぞれ0または1であり、
- 前記重合体は、ランダム重合体である、請求項1から5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6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、
前記光活性層は、電子供与体および電子受容体を含み、
前記電子供与体は、請求項1〜7のいずれか1項に記載の重合体を含み、前記電子受容体は、非フラーレン(non−fullerene)系化合物を含むものである有機太陽電池。 - 前記非フラーレン(non−fullerene)系化合物は、下記化学式Aで表されるものである、請求項8に記載の有機太陽電池:
[化学式A]
X1〜X6は、互いに同一または異なり、それぞれ独立に、水素;または置換もしくは非置換のアルキル基であり、
Z1〜Z4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アリーレン基;または置換もしくは非置換の2価のヘテロ環基であり、
MaおよびMbは、互いに同一または異なり、それぞれ独立に、水素;ハロゲン基;または置換もしくは非置換のアルキル基であり、
pおよびqは、互いに同一または異なり、それぞれ独立に、0〜2の整数であり、
pまたはqが2の場合、括弧内の構造は、互いに同一である。 - 前記電子供与体と前記電子受容体との質量比は、1:2〜2:1である、請求項8から10のいずれか一項に記載の有機太陽電池。
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