JP2013508358A - N型材料および有機電子デバイス - Google Patents
N型材料および有機電子デバイス Download PDFInfo
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- JP2013508358A JP2013508358A JP2012535170A JP2012535170A JP2013508358A JP 2013508358 A JP2013508358 A JP 2013508358A JP 2012535170 A JP2012535170 A JP 2012535170A JP 2012535170 A JP2012535170 A JP 2012535170A JP 2013508358 A JP2013508358 A JP 2013508358A
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- Prior art keywords
- poly
- electron
- diyl
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- independently
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- 239000000463 material Substances 0.000 title claims abstract description 62
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 34
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims abstract description 22
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims abstract description 13
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 claims description 47
- -1 arheteroalkyl Chemical group 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000010409 thin film Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000001408 amides Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000001425 triazolyl group Chemical group 0.000 claims description 7
- 238000009499 grossing Methods 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 5
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 claims description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 4
- 229920000264 poly(3',7'-dimethyloctyloxy phenylene vinylene) Polymers 0.000 claims description 4
- 229920000553 poly(phenylenevinylene) Polymers 0.000 claims description 4
- NUCIQEWGTLOQTR-UHFFFAOYSA-N 4,4-bis(2-ethylhexyl)-4h-cyclopenta[1,2-b:5,4-b']dithiophene Chemical compound S1C=CC2=C1C(SC=C1)=C1C2(CC(CC)CCCC)CC(CC)CCCC NUCIQEWGTLOQTR-UHFFFAOYSA-N 0.000 claims description 3
- LQQKFGSPUYTIRB-UHFFFAOYSA-N 9,9-dihexylfluorene Chemical compound C1=CC=C2C(CCCCCC)(CCCCCC)C3=CC=CC=C3C2=C1 LQQKFGSPUYTIRB-UHFFFAOYSA-N 0.000 claims description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 8
- 150000002894 organic compounds Chemical class 0.000 abstract description 4
- 230000031700 light absorption Effects 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 46
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 239000000370 acceptor Substances 0.000 description 31
- 238000005481 NMR spectroscopy Methods 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 229910052786 argon Inorganic materials 0.000 description 16
- 0 CCNC1C*(C)=C(C)C1 Chemical compound CCNC1C*(C)=C(C)C1 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 238000013086 organic photovoltaic Methods 0.000 description 9
- 239000011575 calcium Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 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 8
- 239000002904 solvent Substances 0.000 description 8
- 229920000144 PEDOT:PSS Polymers 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 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 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- BPTABBGLHGBJQR-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BPTABBGLHGBJQR-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 229910003472 fullerene Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 101100391174 Dictyostelium discoideum forC gene Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
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- 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 2
- 125000005496 phosphonium group Chemical group 0.000 description 2
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- CLGIPVVEERQWSQ-UHFFFAOYSA-N (2,3,4-trifluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(F)C(F)=C1F CLGIPVVEERQWSQ-UHFFFAOYSA-N 0.000 description 1
- UHDDEIOYXFXNNJ-UHFFFAOYSA-N (3,4,5-trifluorophenyl)boronic acid Chemical compound OB(O)C1=CC(F)=C(F)C(F)=C1 UHDDEIOYXFXNNJ-UHFFFAOYSA-N 0.000 description 1
- VKUJTJNTVLWDEM-UHFFFAOYSA-N (9,9-dihexyl-7-trimethylsilylfluoren-2-yl)boronic acid Chemical compound C1=C([Si](C)(C)C)C=C2C(CCCCCC)(CCCCCC)C3=CC(B(O)O)=CC=C3C2=C1 VKUJTJNTVLWDEM-UHFFFAOYSA-N 0.000 description 1
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- ZIIMIGRZSUYQGW-UHFFFAOYSA-N 4,7-bis(5-bromothiophen-2-yl)-2,1,3-benzothiadiazole Chemical compound S1C(Br)=CC=C1C(C1=NSN=C11)=CC=C1C1=CC=C(Br)S1 ZIIMIGRZSUYQGW-UHFFFAOYSA-N 0.000 description 1
- FEOWHLLJXAECMU-UHFFFAOYSA-N 4,7-dibromo-2,1,3-benzothiadiazole Chemical compound BrC1=CC=C(Br)C2=NSN=C12 FEOWHLLJXAECMU-UHFFFAOYSA-N 0.000 description 1
- OGYSYXDNLPNNPW-UHFFFAOYSA-N 4-butoxy-4-oxobutanoic acid Chemical compound CCCCOC(=O)CCC(O)=O OGYSYXDNLPNNPW-UHFFFAOYSA-N 0.000 description 1
- CYKRLNASXFWLKF-UHFFFAOYSA-N CC(C1)SC2=C1CC1=C2BC(C)=C1 Chemical compound CC(C1)SC2=C1CC1=C2BC(C)=C1 CYKRLNASXFWLKF-UHFFFAOYSA-N 0.000 description 1
- HPYMNDNFUAFVEZ-UHFFFAOYSA-N CC1SC(c2c(C3)cc(C)[s]2)=C3C=C1 Chemical compound CC1SC(c2c(C3)cc(C)[s]2)=C3C=C1 HPYMNDNFUAFVEZ-UHFFFAOYSA-N 0.000 description 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 229910000733 Li alloy Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- BBNQFBHQOPZKTI-AATRIKPKSA-N [(e)-2-[4-(trifluoromethyl)phenyl]ethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=C(C(F)(F)F)C=C1 BBNQFBHQOPZKTI-AATRIKPKSA-N 0.000 description 1
- ALMFIOZYDASRRC-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(C(F)(F)F)C=C1 ALMFIOZYDASRRC-UHFFFAOYSA-N 0.000 description 1
- NPNMHHNXCILFEF-UHFFFAOYSA-N [F].[Sn]=O Chemical compound [F].[Sn]=O NPNMHHNXCILFEF-UHFFFAOYSA-N 0.000 description 1
- ASIIQTABPIPDFG-UHFFFAOYSA-L [Sn+2]=O.[F-].[F-] Chemical compound [Sn+2]=O.[F-].[F-] ASIIQTABPIPDFG-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229960002311 dithranol Drugs 0.000 description 1
- 229950004394 ditiocarb Drugs 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229920005570 flexible polymer Polymers 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920003214 poly(methacrylonitrile) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical compound N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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Abstract
【解決手段】式I(式中、各Aは、独立して選択される共役電子吸引性芳香族またはヘテロ芳香族基であり;各Dは、独立して選択されるエテニレン基、エチニレン基または共役電子供与性芳香族もしくはヘテロ芳香族基であり;rは2以上の値を有する整数であり;各nは独立して1〜20の整数であり;そして各pは独立して1〜10の整数である)で表される有機化合物。
【選択図】 なし
Description
ガラス/ITO/PEDOT:PSS/活性層/Ca/Ag(ここで、光活性層は、クロロホルム中、1:1〜1:4重量比のP3HT:式Iの化合物の範囲のある割合のP3HT:式Iの化合物から形成される)。特定の実施形態では、P3HT:式Iの化合物の重量比は1:2または1:3である。
[実施例]
装置
1Hおよび13C NMRデータを、CDCl3を基準とした化学シフトを用いてBruker DPX 400MHz分光計で実施した。マトリックス支援レーザー脱離/イオン化飛行時間型(MALDI−TOF)質量スペクトルを、必要があれば、マトリックスとしてジトラノールおよびイオン化塩としてトリフルオロ酢酸銀を用いてBruker Autoflex TOF/TOF装置で得た。示差走査熱量測定(DSC)を窒素下、DSC Q100装置で実施した(10℃/分のスキャニング速度)。熱重量分析(TGA)を、TGA Q500装置を用いて実施した(10℃/分の加熱速度)。サイクリックボルタンメトリー実験を、Echochimie製Autolabポテンシオスタット(PGSTAT30型)を用いて実施した。すべてのCV測定を支持電解質として0.1Mのテトラブチルアンモニウムヘキサフルオロホスフェートを含むジクロロメタン中で記録した(100mV/sのスキャニング速度)。実験は、白金線作用電極、金対電極、および3MのKCl中Ag/AgCl基準電極からなる通常の3電極配置で室温にて実施した。測定された電位をSCE(飽和カロメル電極)に変換し、対応するイオン化電位(IP)および電子親和性(EA)値は、真空に対するSCEエネルギーレベルとして−4.4eVに基づき、開始レドックス電位から誘導した(EA=Ered-onset+4.4eV、IP=Eox-onset+4.4eV)。UV−VisスペクトルをShimadzuモデル2501−PC UV−VIS分光計で記録し、フォトルミネッセンス(PL)スペクトルをPerkin−Elmer(LS50B)分光蛍光光度計で測定した。
[実施例1] スキーム1にしたがったN−1、N−2、N−3の合成
2の合成。1(0.94g、1.0ミリモル)および無水酢酸ナトリウム(0.16g、2.0ミリモル)を含むTHF溶液(20mL)を0℃まで冷却した。臭素(0.64g、4.0ミリモル)を添加し、混合物を45分間暗所で撹拌した。トリエチルアミン(1.12mL、8.0ミリモル)を添加し、続いて過剰の水性Na2SO4を添加することにより、反応をクエンチした。生成物をジエチルエーテルで抽出し、抽出物を水性Na2SO4で洗浄し、MgSO4上で乾燥した。濾過後、濾液を吸引乾燥し、残留物を熱ヘキサンから再結晶して、生成物を黄色固体として得た(0.91g、94%収率)。
N−1の合成。反応系:2(0.29g、0.30ミリモル)、4−トリフルオロメチルフェニルボロン酸(0.17g、0.90ミリモル)、Pd(PPh3)4(0.014g、0.012ミリモル)。生成物をヘキサンから再結晶し、明黄色固体を得た(0.29g、88%収率)。
N−2の合成。
N−3の合成。
[実施例2] スキーム2にしたがったN−4の合成
4の合成。3(1.11g、1.0ミリモル)および無水酢酸ナトリウム(0.16g、2.0ミリモル)を含むTHF溶液(20mL)を0℃まで冷却した。臭素(0.64g、4.0ミリモル)を添加し、混合物を45分間暗所で撹拌した。トリエチルアミン(1.12mL、8.0ミリモル)を添加し、続いて過剰の水性Na2SO4を添加することにより、反応をクエンチした。生成物をジエチルエーテルで抽出し、抽出物を水性Na2SO4で洗浄し、MgSO4上で乾燥した。濾過後、濾液を吸引乾燥し、残留物を熱ヘキサンから再結晶し、赤色固体を得た(1.06g、94%収率)。
N−4の合成。N−1の合成の同じ前記方法を使用した。カラムクロマトグラフィー後、生成物を、1%ヘキサン中酢酸エチルを用いた薄層クロマトグラフィー(TLC)によりさらに精製した。生成物を次いで熱ヘキサンから再結晶し、生成物を暗赤色固体として得た(収率62%)。
[実施例3] スキーム3にしたがったN−5、N−6、N−7の合成
6の合成。
N−5の合成。還流冷却器を備えた25mLの2口丸底フラスコに、6(0.32g、0.4ミリモル)、トリフルオロフェニルボロン酸(0.31g、1.2ミリモル)およびテトラキス(トリフェニルホスフィン)パラジウム(0)(37mg、2モル%)を入れた。フラスコを窒素でフラッシュし、続いて、トルエン(4.5mL)、2MのNa2CO3(1.5mL)およびエタノール(1.5mL)を添加した。混合物を85℃で18時間撹拌した。1mLの水中50mgのジエチルジチオカルバミン酸ナトリウムを次いで添加し、混合物を一夜80℃で撹拌した。これを次いで冷却し、水に注ぎ、ジクロロメタンで抽出した。有機層を水で洗浄し、MgSO4で乾燥し、濃縮し、シリカ上クロマトグラフィー(5%ヘキサン中ジクロロメタン)にかけ、ジクロロメタン/エタノールから再結晶し、標記化合物を得た(220mg、61%)。
N−6の合成。10mLのマイクロ波用ガラスバイアルに、撹拌棒、6(158mg、0.2ミリモル)、3,5−ビス(トリフルオロメチル)ベンゼンボロン酸(155mg、0.6ミリモル)、およびジクロロビス(トリフェニルホスフィン)パラジウム(II)(6mg、2モル%)を入れた。バイアルを窒素でパージし、密封した。1,2−ジメトキシエタン(0.99mL)、水(0.43mL)およびエタノール(0.23mL)を次いでシリンジを通してバイアルに添加した。ガラスバイアルをマイクロ波反応器中で2分間100℃、15分間150度にて加熱した。バイアルを次いで冷却し、内容物をジクロロメタンで抽出した。有機層をMgSO4で乾燥し、濃縮し、シリカ上クロマトグラフィー(5%のヘキサン中クロロホルム)にかけて、標記化合物を得た(55mg、26%)。
N−7の合成。
[実施例4] スキーム4にしたがったN−8、N−9、N−10、N−11の合成
N−8の合成。
N−9の合成。
N−10の合成。
N−11の合成。
[実施例5] 化合物N−1〜N−11の特性化
化合物をNMRおよびMALDI−TOFにより特性化した。物質の熱特性をDSCおよびTGAにより分析し、結果を第1表に示す。この物質は、166〜231℃の範囲の融点を有し、N2下で高い熱安定性(>330℃)を有する。化合物の光物理的特性をトルエン中UV−visおよび蛍光分光法により測定した。化合物は、330〜700nmで強い吸収を示す。CH2C12中サイクリックボルタンモグラムを用いて、物質のHOMOおよびLUMO特性を測定した。HOMO/LUMOおよびバンドギャップ値は、HOMOは−5.18〜−5.79eV、LUMOは−2.98〜−3.55eVの範囲に調節することができた。
N−4、N−8、およびN−9をOPVデバイス製作のために選択し、n型材料の光起電装置性能を調べた。
Claims (15)
- 式I:
各Dは、独立して選択されるエテニレン基、エチニレン基または5〜50個の主鎖原子を有する共役電子供与性芳香族もしくはヘテロ芳香族基であり;各Dは場合によって1以上の電子供与性置換基または電子吸引性置換基で置換され(ただし、置換される場合でも、各Dの電子特性は電子供与性であるとする);
rは2以上の値を有する整数であり;そして
各nは独立して1〜20の整数でありそして各pは独立して1〜10の整数である)
の化合物。 - 各Aが独立して、1以上のハロ、フルオロアルキル、パーフルオロアルキル、カルボキシル、シアノ、アンモニオ、ニトロ、チオニル、スルホニル、酸素を介して主鎖に結合したアミド、ピリジニウム、ホスホニウム、ピリジル、チアゾリル、オキサジアゾリル、トリアゾリル、アルコキシル、アルキルチオ、アミノ、ヒドロキシル、窒素を介して主鎖と結合したアミド、酸素を介して主鎖と結合したカルボキシル、フェニル、ナフチル、チエニル、フリル、ピロリル、カルバゾリル、アルキル、アルケニルもしくはアルキニルまたはそれらの任意の組み合わせで場合によって置換され、置換される場合、各Aの電子特性は、電子受容性である、請求項1〜3のいずれか1項に記載の化合物。
- 各Dが独立して、1以上のアルコキシル、アルキルチオ、アミノ、ヒドロキシル、窒素を介して主鎖と結合したアミド、酸素を介して主鎖と結合したカルボキシル、フェニル、ナフチル、チエニル、フリル、ピロリル、カルバゾリル、アルキル、アルケニル、アルキニル、ハロ、フルオロアルキル、パーフルオロアルキル、カルボキシル、シアノ、アンモニオ、ニトロ、チオニル、スルホニル、酸素を介して主鎖に結合したアミド、ピリジニウム、ホスホニウム、ピリジル、チアゾリル、オキサジアゾリルもしくはトリアゾリルまたはそれらの任意の組み合わせで場合によって置換され、ただし、置換される場合、各Dの電子特性は電子供与性である、請求項1〜4のいずれか1項に記載の化合物。
- 請求項1〜6のいずれか1項に記載の化合物を含む薄膜。
- 電子供与体材料をさらに含む、請求項7記載の薄膜。
- 電子供与体材料が、立体規則性ポリ(3−ヘキシルチオフェン−2,5−ジイル)(P3HT)、立体規則性ポリ(3−オシルチオフェン−2,5−ジイル)(P3OT)、立体規則性ポリ(クォーターチオフェン)(PQT)、a−ポリ(フェニレンエチニレン)−ポリ(フェニレンビニレン)(A−PPE−PPV)、ポリ[2−メトキシ−5−(2’−エチルヘキシルオキシ)−1,4−フェニレンビニレン](MEH−PPV)、ポリ[2−メトキシ−5−(3,7−ジメチルオクチルオキシ)−1,4−フェニレンビニレン](MDMO−PPV)、ポリ(9,9−ジヘキシル−フルオレン−2,7−ジイル−アルト−ビチオフェン−2,5’−ジイル)、ポリ(N−アルキル−カルバゾ−2,7−ジイル−アルト−4,7−ジチエニル−2,1,3−ベンゾチアジアゾ−2,5”−ジイル)、ポリ[2,6−(4,4−ビス(2−エチルヘキシル)−4H−シクロペンタ[2,1−b:3,4−b’]ジチオフェン)−アルト−4,7−(2,1,3−ベンゾチアジアゾール)](PCPDTBT)、ポリ(9,9−ジオクチル−シラフルオレン−2,7−ジイル−アルト−4,7−ジチエニル−2,1,3−ベンゾチアジアゾ−2,5”−ジイル)、またはポリ[2,6−(4,4−ビス(2−エチルヘキシル)−4H−シクロペンタ[2,1−b:3,4−b’]ジチオフェンシロール)−アルト−4,7−(2,1,3−ベンゾチアジアゾール)]を含む、請求項8に記載の薄膜。
- 供与体材料がP3HTを含む、請求項8に記載の薄膜。
- アノード、カソードおよび請求項1〜6のいずれか1項に記載の化合物を含む電子受容体材料を含むデバイスであって、電子受容体材料がアノードとカソードの間に配置されている、デバイス。
- 電子受容体材料が光活性層中にある、請求項11に記載のデバイス。
- 光活性層が電子供与体材料をさらに含む、請求項12に記載のデバイス。
- 供与体材料が、立体規則性ポリ(3−ヘキシルチオフェン−2,5−ジイル)(P3HT)、立体規則性ポリ(3−オシルチオフェン−2,5−ジイル)(P3OT)、立体規則性ポリ(クォーターチオフェン)(PQT)、a−ポリ(フェニレンエチニレン)−ポリ(フェニレンビニレン)(A−PPE−PPV)、ポリ[2−メトキシ−5−(2’−エチル−ヘキシルオキシ)−1,4−フェニレンビニレン](MEH−PPV)、ポリ[2−メトキシ−5−(3,7−ジメチルオクチルオキシ)−1,4−フェニレンビニレン](MDMO−PPV)、ポリ(9,9−ジヘキシル−フルオレン−2,7−ジイル−アルト−ビチオフェン−2,5’−ジイル)、ポリ(N−アルキル−カルバゾ−2,7−ジイル−アルト−4,7−ジチエニル−2,1,3−ベンゾチアジアゾ−2,5”−ジイル)、ポリ[2,6−(4,4−ビス(2−エチルヘキシル)−4H−シクロペンタ[2,1−b:3,4−b’]ジチオフェン)−アルト−4,7−(2,1,3−ベンゾチアジアゾール)](PCPDTBT)、ポリ(9,9−ジオクチル−シラフルオレン−2,7−ジイル−アルト−4,7−ジチエニル−2,1,3−ベンゾチアジアゾ−2,5”−ジイル)、またはポリ[2,6−(4,4−ビス(2−エチルヘキシル)−4H−シクロペンタ[2,1−b:3,4−b’]ジチオフェンシロール)−アルト−4,7−(2,1,3−ベンゾチアジアゾール)]を含む、請求項13に記載のデバイス。
- 光活性層とアノードの間、または光活性層とカソードの間に配置されたスムージング層をさらに含む、請求項11〜14のいずれか1項に記載のデバイス。
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WO2013123047A1 (en) | 2012-02-14 | 2013-08-22 | Next Energy Technologies Inc. | Electronic devices using organic small molecule semiconducting compounds |
US9865821B2 (en) | 2012-02-17 | 2018-01-09 | Next Energy Technologies, Inc. | Organic semiconducting compounds for use in organic electronic devices |
US20130247989A1 (en) * | 2012-03-23 | 2013-09-26 | The Regents Of The University Of California | Inert solution-processable molecular chromophores for organic electronic devices |
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US10770665B2 (en) | 2015-03-26 | 2020-09-08 | Next Energy Technology, Inc. | Fluorinated dye compounds for organic solar cells |
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