JP2020506252A - 化合物およびこれを含む有機太陽電池 - Google Patents
化合物およびこれを含む有機太陽電池 Download PDFInfo
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- JP2020506252A JP2020506252A JP2019536231A JP2019536231A JP2020506252A JP 2020506252 A JP2020506252 A JP 2020506252A JP 2019536231 A JP2019536231 A JP 2019536231A JP 2019536231 A JP2019536231 A JP 2019536231A JP 2020506252 A JP2020506252 A JP 2020506252A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 107
- 239000000126 substance Substances 0.000 claims abstract description 46
- 239000010410 layer Substances 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- -1 nitro, hydroxy, carbonyl Chemical group 0.000 claims description 48
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 238000002347 injection Methods 0.000 claims description 21
- 239000007924 injection Substances 0.000 claims description 21
- 230000005525 hole transport Effects 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 10
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 10
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
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- 150000003949 imides Chemical class 0.000 claims description 9
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- 150000001408 amides Chemical class 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
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- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 96
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- 125000004432 carbon atom Chemical group C* 0.000 description 44
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 239000000203 mixture Substances 0.000 description 39
- 238000004519 manufacturing process Methods 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 20
- 239000000758 substrate Substances 0.000 description 19
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- 239000003054 catalyst Substances 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 11
- 125000001072 heteroaryl group Chemical group 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- 238000000944 Soxhlet extraction Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 9
- 238000007789 sealing Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000005264 aryl amine group Chemical group 0.000 description 7
- 0 CC(C(*)=C(*)C1=C(C)C=C*1)=C Chemical compound CC(C(*)=C(*)C1=C(C)C=C*1)=C 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 125000005241 heteroarylamino group Chemical group 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 150000003974 aralkylamines Chemical group 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- WZQSBCHNVPAYOC-UHFFFAOYSA-N chloro(trihexyl)silane Chemical compound CCCCCC[Si](Cl)(CCCCCC)CCCCCC WZQSBCHNVPAYOC-UHFFFAOYSA-N 0.000 description 3
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 2
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 2
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- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 2
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- SBNNYCBGSSSIAM-UHFFFAOYSA-N CC(C)(C)C(C)(C)NC Chemical compound CC(C)(C)C(C)(C)NC SBNNYCBGSSSIAM-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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Images
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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Abstract
Description
[化学式1]
Ar1は、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、
Ar2は、置換もしくは非置換のアルキレン基;置換もしくは非置換のシクロアルキレン基;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、
R1〜R3は、互いに同一または異なり、それぞれ独立に、アルキル基であり、
aは、1〜5の整数であり、
aが2以上の場合、Ar2は、互いに同一または異なり、
nは、1〜10,000の整数であり、
mは、1または2である。
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、前記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2]
Ar1、Ar2、aおよびnは、化学式1で定義した通りであり、
R1〜R6は、互いに同一または異なり、それぞれ独立に、アルキル基である。
X9〜X11、X14、X15およびX31〜X35は、互いに同一または異なり、それぞれ独立に、S、O、Se、Te、NR、CRR'、SiRR'、PR'、またはGeRR'であり、
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;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミド基;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シクロアルキル基;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オキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;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、
前記構造式中の水素1つまたは2つが
[化学式1−1]
Ar2、R1〜R3およびnは、化学式1で定義した通りであり、
X10、X11、X34およびX35は、互いに同一または異なり、それぞれ独立に、S、O、Se、Te、NR、CRR'、SiRR'、PR'、またはGeRR'であり、
R4〜R6は、互いに同一または異なり、それぞれ独立に、アルキル基であり、
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;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミド基;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シクロアルキル基;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オキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;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。
a、a'、bおよびb'は、互いに同一または異なり、それぞれ0〜5の整数であり、
a、a'、bおよびb'が2以上の場合、括弧内の置換基は、互いに同一または異なり、
Y1〜Y13は、互いに同一または異なり、それぞれ独立に、S、O、Se、Te、NR、CRR'、SiRR'、PR'、またはGeRR'であり、
Y14およびY15は、互いに同一または異なり、それぞれ独立に、C、Si、またはGeであり、
R10〜R23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;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミド基;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シクロアルキル基;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オキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;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1−11]
R1〜R3およびnは、化学式1で定義した通りであり、
X10、X11、X34、X35およびY6〜Y11は、互いに同一または異なり、それぞれ独立に、S、O、Se、Te、NR、CRR'、SiRR'、PR'、またはGeRR'であり、
R4〜R6は、互いに同一または異なり、それぞれ独立に、アルキル基であり、
R10〜R19、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;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミド基;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シクロアルキル基;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オキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;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、
前記有機物層のうちの1層以上は、前記化合物を含むものである有機太陽電池を提供する。
前記製造例で製造した化合物1をドナーとして用い、PCBMをアクセプタとして用いて、1:2の比率でクロロベンゼン(Chlorobenzene、CB)に溶かして複合溶液(composit solution)を製造した。この時、濃度は2.0wt%に調節し、有機太陽電池はITO/ZnO/光活性層/MoO3/Agの構造とした。ITOがコーティングされたガラス基板は蒸留水、アセトン、2−プロパノールを用いて超音波洗浄し、ITO表面を10分間オゾン処理した後、ZnO前駆体溶液をスピンコーティングして、120℃で10分間熱処理した。その後、複合溶液を0.45μmのPPシリンジフィルタ(syringe filter)で濾過した後、スピンコーティングして光活性層を形成した。その後、熱蒸着器でMoO3を0.4Å/sの速度で5nm〜20nmの厚さに前記光活性層上に蒸着して正孔輸送層を製造した。その後、熱蒸着器の内部でAgを1Å/sの速度で前記正孔輸送層上に10nmに蒸着して有機太陽電池を製造した。
前記実施例1における化合物1の代わりに化合物2を用いたことを除き、実施例1と同様の方法で有機太陽電池を製造した。
前記実施例1における化合物1の代わりに化合物3を用いたことを除き、実施例1と同様の方法で有機太陽電池を製造した。
前記実施例1における化合物1の代わりに化合物4を用いたことを除き、実施例1と同様の方法で有機太陽電池を製造した。
前記実施例1における化合物1の代わりに化合物5を用いたことを除き、実施例1と同様の方法で有機太陽電池を製造した。
前記実施例1における化合物1の代わりに化合物6を用いたことを除き、実施例1と同様の方法で有機太陽電池を製造した。
前記実施例1における化合物1の代わりに化合物7を用いたことを除き、実施例1と同様の方法で有機太陽電池を製造した。
前記実施例1における化合物1の代わりに化合物8を用いたことを除き、実施例1と同様の方法で有機太陽電池を製造した。
前記実施例1における化合物1の代わりに化合物9を用いたことを除き、実施例1と同様の方法で有機太陽電池を製造した。
前記実施例1における化合物1の代わりに化合物10を用いたことを除き、実施例1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 (11)
- 前記Ar1は、下記構造のうちのいずれか1つまたは2つ以上の組み合わせを含むものである、請求項1または2に記載の化合物:
X9〜X11、X14、X15およびX31〜X35は、互いに同一または異なり、それぞれ独立に、S、O、Se、Te、NR、CRR'、SiRR'、PR'、またはGeRR'であり、
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;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミド基;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シクロアルキル基;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オキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;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、
前記構造式中の水素1つまたは2つが
- 前記Ar2は、下記構造のうちのいずれか1つまたは2つ以上の組み合わせを含むものである、請求項1または2に記載の化合物:
a、a'、bおよびb'は、互いに同一または異なり、それぞれ0〜5の整数であり、
a、a'、bおよびb'が2以上の場合、括弧内の置換基は、互いに同一または異なり、
Y1〜Y13は、互いに同一または異なり、それぞれ独立に、S、O、Se、Te、NR、CRR'、SiRR'、PR'、またはGeRR'であり、
Y14およびY15は、互いに同一または異なり、それぞれ独立に、C、Si、またはGeであり、
R10〜R23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;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミド基;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シクロアルキル基;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オキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;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。 - 前記化合物は、下記化学式1−1または化学式1−2で表されるものである、請求項1に記載の化合物:
[化学式1−1]
Ar2、R1〜R3およびnは、化学式1で定義した通りであり、
X10、X11、X34およびX35は、互いに同一または異なり、それぞれ独立に、S、O、Se、Te、NR、CRR'、SiRR'、PR'、またはGeRR'であり、
R4〜R6は、互いに同一または異なり、それぞれ独立に、アルキル基であり、
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;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミド基;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シクロアルキル基;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オキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;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。 - 前記化合物は、下記化学式1−11〜化学式1−16のうちのいずれか1つで表されるものである、請求項1に記載の化合物:
[化学式1−11]
R1〜R3およびnは、化学式1で定義した通りであり、
X10、X11、X34、X35およびY6〜Y11は、互いに同一または異なり、それぞれ独立に、S、O、Se、Te、NR、CRR'、SiRR'、PR'、またはGeRR'であり、
R4〜R6は、互いに同一または異なり、それぞれ独立に、アルキル基であり、
R10〜R19、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;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミド基;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シクロアルキル基;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オキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;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。 - 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1〜6のいずれか1項に記載の化合物を含むものである有機太陽電池。 - 前記有機物層は、正孔輸送層、正孔注入層、または正孔輸送および正孔注入を同時に行う層を含み、
前記正孔輸送層、正孔注入層、または正孔輸送および正孔注入を同時に行う層は、前記化合物を含む、請求項7に記載の有機太陽電池。 - 前記有機物層は、電子注入層、電子輸送層、または電子注入および電子輸送を同時に行う層を含み、
前記電子注入層、電子輸送層、または電子注入および電子輸送を同時に行う層は、前記化合物を含む、請求項7に記載の有機太陽電池。 - 前記光活性層は、電子供与体および電子受容体を含み、
前記電子供与体は、前記化合物を含むものである、請求項7から9のいずれか一項に記載の有機太陽電池。 - 前記有機太陽電池は、正孔注入層、正孔輸送層、正孔阻止層、電荷発生層、電子阻止層、電子注入層、および電子輸送層からなる群より選択される1または2以上の有機物層をさらに含むものである、請求項7から10のいずれか一項に記載の有機太陽電池。
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