JP2011529631A - 光起電力デバイスのためのペリレンテトラカルボキシイミド誘導体 - Google Patents
光起電力デバイスのためのペリレンテトラカルボキシイミド誘導体 Download PDFInfo
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- JP2011529631A JP2011529631A JP2011520463A JP2011520463A JP2011529631A JP 2011529631 A JP2011529631 A JP 2011529631A JP 2011520463 A JP2011520463 A JP 2011520463A JP 2011520463 A JP2011520463 A JP 2011520463A JP 2011529631 A JP2011529631 A JP 2011529631A
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- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- -1 diisopropylphenyl Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 15
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 150000001345 alkine derivatives Chemical class 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229920006295 polythiol Polymers 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- 239000011541 reaction mixture Substances 0.000 description 51
- 229910052757 nitrogen Inorganic materials 0.000 description 34
- 239000000243 solution Substances 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- 239000000203 mixture Substances 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- 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 24
- 239000007787 solid Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000013086 organic photovoltaic Methods 0.000 description 21
- 239000010410 layer Substances 0.000 description 18
- 238000002390 rotary evaporation Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- VDNOMEBXKZREHO-UHFFFAOYSA-N 6-iminohexyl 3,5-didodecoxybenzoate Chemical compound CCCCCCCCCCCCOC1=CC(OCCCCCCCCCCCC)=CC(C(=O)OCCCCCC=N)=C1 VDNOMEBXKZREHO-UHFFFAOYSA-N 0.000 description 13
- 239000000370 acceptor Substances 0.000 description 13
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 11
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 9
- 238000010791 quenching Methods 0.000 description 9
- 230000000171 quenching effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 7
- 229910052741 iridium Inorganic materials 0.000 description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000002484 cyclic voltammetry Methods 0.000 description 6
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000002411 thermogravimetry Methods 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 5
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 4
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 4
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 4
- PONZBUKBFVIXOD-UHFFFAOYSA-N 9,10-dicarbamoylperylene-3,4-dicarboxylic acid Chemical class C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=N)C2=C1C3=CC=C2C(=N)O PONZBUKBFVIXOD-UHFFFAOYSA-N 0.000 description 4
- PLTWYBSYQRKPQG-UHFFFAOYSA-N C=1C=CSC=1C1(Br)CC=CS1.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 Chemical compound C=1C=CSC=1C1(Br)CC=CS1.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 PLTWYBSYQRKPQG-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- RNVFYQUEEMZKLR-UHFFFAOYSA-N methyl 3,5-dihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=CC(O)=C1 RNVFYQUEEMZKLR-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 229910021417 amorphous silicon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 150000002503 iridium Chemical class 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
- KXSFECAJUBPPFE-UHFFFAOYSA-N 2,2':5',2''-terthiophene Chemical compound C1=CSC(C=2SC(=CC=2)C=2SC=CC=2)=C1 KXSFECAJUBPPFE-UHFFFAOYSA-N 0.000 description 2
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 2
- QZVHYFUVMQIGGM-UHFFFAOYSA-N 2-Hexylthiophene Chemical compound CCCCCCC1=CC=CS1 QZVHYFUVMQIGGM-UHFFFAOYSA-N 0.000 description 2
- CNLSKHCVAUZKTB-UHFFFAOYSA-N 3,5-didodecoxybenzoic acid Chemical compound CCCCCCCCCCCCOC1=CC(OCCCCCCCCCCCC)=CC(C(O)=O)=C1 CNLSKHCVAUZKTB-UHFFFAOYSA-N 0.000 description 2
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QBGPSEDSHFOKJR-UHFFFAOYSA-N boric acid;2-(2-hexyl-3h-thiophen-2-yl)-3-thiophen-2-ylthiophene Chemical compound OB(O)O.S1C=CC(C=2SC=CC=2)=C1C1(CCCCCC)CC=CS1 QBGPSEDSHFOKJR-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910021419 crystalline silicon Inorganic materials 0.000 description 2
- 229910000071 diazene Inorganic materials 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002979 perylenes Chemical group 0.000 description 2
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
- OZNYBWZLXMPDRK-UHFFFAOYSA-N 1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=C(Br)C=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=C(Br)C=C(C(O)=O)C2=C1C3=CC=C2C(=O)O OZNYBWZLXMPDRK-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- KGCJCDXZSPVGGX-UHFFFAOYSA-N 1-bromoperylene Chemical group C1=CC(C=2C(Br)=CC=C3C=2C2=CC=C3)=C3C2=CC=CC3=C1 KGCJCDXZSPVGGX-UHFFFAOYSA-N 0.000 description 1
- UPOXMRITEFEFOG-UHFFFAOYSA-N 2,3-dithiophen-2-ylthiophene perylene Chemical compound C1=CSC(C2=C(SC=C2)C=2SC=CC=2)=C1.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 UPOXMRITEFEFOG-UHFFFAOYSA-N 0.000 description 1
- HVKXVCDUSKRXKX-UHFFFAOYSA-N 2-(2-bromo-3H-thiophen-2-yl)-3-thiophen-2-ylthiophene perylene Chemical compound S1C=CC(C=2SC=CC=2)=C1C1(Br)CC=CS1.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 HVKXVCDUSKRXKX-UHFFFAOYSA-N 0.000 description 1
- KUJYDIFFRDAYDH-UHFFFAOYSA-N 2-thiophen-2-yl-5-[5-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophene Chemical group C1=CSC(C=2SC(=CC=2)C=2SC(=CC=2)C=2SC(=CC=2)C=2SC(=CC=2)C=2SC=CC=2)=C1 KUJYDIFFRDAYDH-UHFFFAOYSA-N 0.000 description 1
- ORJVNTYEPAIOJV-UHFFFAOYSA-N 3-bromo-2-thiophen-2-ylthiophene perylene Chemical compound C1=CSC(C=2SC=CC=2)=C1Br.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 ORJVNTYEPAIOJV-UHFFFAOYSA-N 0.000 description 1
- JEDHEMYZURJGRQ-UHFFFAOYSA-N 3-hexylthiophene Chemical compound CCCCCCC=1C=CSC=1 JEDHEMYZURJGRQ-UHFFFAOYSA-N 0.000 description 1
- MARUHZGHZWCEQU-UHFFFAOYSA-N 5-phenyl-2h-tetrazole Chemical compound C1=CC=CC=C1C1=NNN=N1 MARUHZGHZWCEQU-UHFFFAOYSA-N 0.000 description 1
- IMXNSYLJKARJKD-UHFFFAOYSA-N 6-[(2-bromoperylen-1-yl)amino]hexan-1-ol Chemical group C1=CC(C=2C(NCCCCCCO)=C(Br)C=C3C=2C2=CC=C3)=C3C2=CC=CC3=C1 IMXNSYLJKARJKD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- AYVQDNKHPMWPMQ-UHFFFAOYSA-N B(O)(O)O.C(CCCCC)C1=C(SC=C1)C=1SC=CC1C=1SC=CC1 Chemical compound B(O)(O)O.C(CCCCC)C1=C(SC=C1)C=1SC=CC1C=1SC=CC1 AYVQDNKHPMWPMQ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- NSNPWMPQNPSJTQ-UHFFFAOYSA-N BrC1=C(SC=C1)C=1SC=CC1C=1SC=CC1.C1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45 Chemical compound BrC1=C(SC=C1)C=1SC=CC1C=1SC=CC1.C1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45 NSNPWMPQNPSJTQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- NMFFQIWOMOZFSU-UHFFFAOYSA-N boric acid;3-hexyl-2-thiophen-2-ylthiophene Chemical compound OB(O)O.C1=CSC(C=2SC=CC=2)=C1CCCCCC NMFFQIWOMOZFSU-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 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
- 125000005446 heptyloxy 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])O* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- KJOLVZJFMDVPGB-UHFFFAOYSA-N perylenediimide Chemical compound C=12C3=CC=C(C(NC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 KJOLVZJFMDVPGB-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000005476 size effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000003115 supporting electrolyte Substances 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
- 238000012360 testing method Methods 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Photovoltaic Devices (AREA)
Abstract
Description
Mは、以下の式:
R1、R2、R3、R4、R5、R6、R7、R8、R10、R11、X1、X2およびX3は、各出現で同じかまたは異なり、1つ以上の非芳香族基で置換されていてもよい、−H、−F、−Cl、−Br、−NO2、−CN、直鎖もしくは分枝のC1〜20アルキル、C2〜20アルケン、C2〜20アルキン、C3〜20環状アルキル、直鎖もしくは分枝のC1〜20アルコキシ、C1〜20ジアルキルアミノ、C4〜20ポリオキサアルキル、C4〜20ポリチオアルキル、C4〜20ポリアザアルキル、C4〜14アリールおよびC4〜14ヘテロアリールから成る群より選択され、ここで、R10およびR11またはR1、R2、R3、R4、R5、R6、R7、R8およびX1のうちのいずれかは、場合により芳香族であってよい単環式環または多環式環を一緒に形成していてもよく;
Lは、−NR9−、−PR9−、−O−および−S−から成る群より選択され、ここで、R9は、1つ以上の非芳香族基で置換されていてもよい、−H、−F、−Cl、−Br、−NO2、−CN、直鎖もしくは分枝のC1〜20アルキル、C2〜20アルケン、C2〜20アルキン、C3〜20環状アルキル、直鎖もしくは分枝のC1〜20アルコキシ、C1〜20ジアルキルアミノ、C4〜20ポリオキサアルキル、C4〜20ポリチオアルキル、C4〜20ポリアザアルキル、C4〜14アリールおよびC4〜14ヘテロアリールから成る群より選択され、;
a、bおよびcは、各出現で同じかまたは異なり、0〜2の整数であり;
dおよびeは、各出現で同じかまたは異なり、0〜3の整数であり;
xおよびyは、各出現で同じかまたは異なり、0〜4の整数であり;
zは、0または1である。
電気化学測定を、RTで、白金電極(直径2mm)、Pt線対電極、およびAg/AgCl基準電極から成る電気化学的電池を用い、CHI600C(CH Instruments Inc.,USA)を使用して行った。ジクロロメタン(Aldrich,HPLCグレード)中の0.1M過塩素酸テトラブチルアンモニウム(Bu4NClO4、TBAP)を、支持電解質として使用した(走査速度50mVs−1)。
上記の実施例1〜5において得られた化合物のUV−可視吸収スペクトルを、JascoのV−570UV−可視分光計を使用して測定した(クロロホルム中5×10−5M)。その結果を図5a〜bおよび下記表1および2に示す。
熱重量分析(TGA)を、Mettler Toledo TGA/SDTA 851(Mettler−Toledo GmbH,Schwerzenbach,Switzerland)で行い、示差走査熱量分析(DSC)を、PerkinElmer Pyris 1測定装置(U.S.A)で、N2雰囲気下、10℃/分の速度で実施した。温度が上昇する中、試験化合物の5重量%が減少した時点の温度を測定した。図6は、TCPTCDI誘導体のTGA曲線を示している。オリゴ−TCPTCDI誘導体のTGAサーモグラムは、5%の減量が362〜388℃の範囲で起こり、オリゴ−TCPTCDIが少なくとも360℃までは安定していることを示した。これは、TCPTCDI誘導体にはOPVデバイス用途に十分な熱安定性があることを示している。
TCPTCDIのUV−可視吸収挙動を、OPVデバイスにおける従来の供与体材料であるIr錯体(Ir(btp)2(acac))のものと比較した。Ir錯体の吸収スペクトルを、実施例30と同じ方法を用いて測定した。図7は、TCPTCDIおよびIr錯体のUV−可視吸収挙動を比較したデータを示しており、TCPTCDI(SP2T)は、イリジウム錯体よりもはるかに長い(赤色)波長領域に吸収を有する。SP2Tの最長λmaxにおけるモル吸光率(2.4×104)は、475nmにおけるイリジウム錯体のモル吸光率(6.0×103)より4倍大きい。より長い吸収波長に吸収を有し、最長λmaxにおける吸光率がより高いことから、TCPTCDIは、Ir錯体よりも効率の良い供与体分子として有能である。
TCPTCDIは、TCPTCDIよりも高いエネルギーバンドを有する供与体分子が利用される場合には、受容体分子としても使用され得る。例えば、Ir(btp)2(acac)またはP3HTが、供与体分子として使用され得る(図3参照)。本実施例においては、イリジウム錯体Ir(btp)2(acac)の三重項リン光の消光を、TCPTCDIを使用して決定した。
Claims (13)
- 式I:
Mは以下の式:
R1、R2、R3、R4、R5、R6、R7、R8、R10、R11、X1、X2およびX3は、各出現で同じかまたは異なり、1つ以上の非芳香族基で置換されていてもよい、−H、−F、−Cl、−Br、−NO2、−CN、直鎖もしくは分枝のC1〜20アルキル、C2〜20アルケン、C2〜20アルキン、C3〜20環状アルキル、直鎖もしくは分枝のC1〜20アルコキシ、C1〜20ジアルキルアミノ、C4〜20ポリオキサアルキル、C4〜20ポリチオアルキル、C4〜20ポリアザアルキル、C4〜14アリールおよびC4〜14ヘテロアリールから成る群より選択され、ここで、R10およびR11またはR1、R2、R3、R4、R5、R6、R7、R8およびX1のうちのいずれかは、場合により芳香族であってよい単環式環または多環式環を一緒に形成していてもよく;
Lは、−NR9−、−PR9−、−O−および−S−から成る群より選択され、ここで、R9は、1つ以上の非芳香族基で置換されていてもよい、−H、−F、−Cl、−Br、−NO2、−CN、直鎖もしくは分枝のC1〜20アルキル、C2〜20アルケン、C2〜20アルキン、C3〜20環状アルキル、直鎖もしくは分枝のC1〜20アルコキシ、C1〜20ジアルキルアミノ、C4〜20ポリオキサアルキル、C4〜20ポリチオアルキル、C4〜20ポリアザアルキル、C4〜14アリールおよびC4〜14ヘテロアリールから成る群より選択され、;
a、bおよびcは、各出現で同じかまたは異なり、0〜2の整数であり;
dおよびeは、各出現で同じかまたは異なり、0〜3の整数であり;
xおよびyは、各出現で同じかまたは異なり、0〜4の整数であり;
zは、0または1である
化合物。 - R1が、1つ以上の非芳香族基で置換されていてもよい、−H、直鎖もしくは分枝のC1〜20アルキル、C4〜20ポリオキサアルキル、C4〜20ポリチオアルキル、またはC4〜20ポリアザアルキルである、請求項1に記載の化合物。
- R2およびR3が、1つ以上の非芳香族基で置換されていてもよいC4〜14アリールである、請求項1または2に記載の化合物。
- R2およびR3が、ジイソプロピルフェニルである、請求項3に記載の化合物。
- R4、R5、R6およびR7が、−Hである、請求項1〜4のいずれか1項に記載の化合物。
- R8が、以下の式:
式中、R12は、1つ以上の非芳香族基で置換されていてもよい、−F、−Cl、−Br、−NO2、−CN、直鎖もしくは分枝のC1〜20アルキル、C2〜20アルケン、C2〜20アルキン、C3〜20環状アルキル、直鎖もしくは分枝のC1〜20アルコキシ、C1〜20ジアルキルアミノ、C4〜20ポリオキサアルキル、C4〜20ポリチオアルキル、C4〜20ポリアザアルキル、C4〜14アリールおよびC4〜14ヘテロアリールから成る群より選択され、ここで、fが少なくとも2の整数である場合、複数のR12が、場合により芳香族であってよい単環式環または多環式環を一緒に形成していてもよく;
fは、0〜5の整数である、請求項1〜5のいずれか1項に記載の化合物。 - R8−L−が、以下の式:
- 前記化合物が、以下の式:
- R1が、1つ以上のシアノ基および/またはカルボキシル基で置換された、直鎖もしくは分枝のC1〜20アルキル、C2〜20アルケン、C2〜20アルキン、C4〜20ポリオキサアルキル、C4〜20ポリチオアルキル、またはC4〜20ポリアザアルキルである、請求項1、3、4、5、6または7のいずれか1項に記載の化合物。
- 前記化合物が、以下の式:
R1が、
nが2〜6の整数である、請求項9に記載の化合物。 - 請求項1〜10のいずれか1項に記載の化合物を含む分子ヘテロ接合材料。
- 請求項11に記載の分子ヘテロ接合材料の、光起電力デバイスにおける使用。
- 請求項11に記載の分子ヘテロ接合材料を含む光起電力デバイス。
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DE102006048638A1 (de) * | 2006-10-13 | 2008-04-17 | Langhals, Heinz, Prof. Dr. | Perylenfarbstoffe mit NIR-Absorption, starker Fluoreszenz und großem Stokes-Shift |
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TW201016695A (en) | 2010-05-01 |
US20110130566A1 (en) | 2011-06-02 |
US8618298B2 (en) | 2013-12-31 |
TWI473804B (zh) | 2015-02-21 |
KR20110036637A (ko) | 2011-04-07 |
WO2010012710A1 (en) | 2010-02-04 |
CN102112470B (zh) | 2014-12-10 |
JP5568554B2 (ja) | 2014-08-06 |
EP2307406A1 (en) | 2011-04-13 |
CN102112470A (zh) | 2011-06-29 |
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