WO2015108206A1 - 化合物および電子素子 - Google Patents
化合物および電子素子 Download PDFInfo
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- WO2015108206A1 WO2015108206A1 PCT/JP2015/051937 JP2015051937W WO2015108206A1 WO 2015108206 A1 WO2015108206 A1 WO 2015108206A1 JP 2015051937 W JP2015051937 W JP 2015051937W WO 2015108206 A1 WO2015108206 A1 WO 2015108206A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 202
- 125000005843 halogen group Chemical group 0.000 claims abstract description 53
- 125000000962 organic group Chemical group 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 24
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 23
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 21
- 125000003277 amino group Chemical group 0.000 claims abstract description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 84
- 229920000642 polymer Polymers 0.000 claims description 78
- 239000010409 thin film Substances 0.000 claims description 47
- 125000005549 heteroarylene group Chemical group 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- -1 silylthio group Chemical group 0.000 description 141
- 239000010410 layer Substances 0.000 description 74
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 125000004432 carbon atom Chemical group C* 0.000 description 54
- 239000000243 solution Substances 0.000 description 49
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 44
- 238000000034 method Methods 0.000 description 36
- 239000000758 substrate Substances 0.000 description 36
- 125000003118 aryl group Chemical group 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- 239000004065 semiconductor Substances 0.000 description 30
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
- 239000010408 film Substances 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 27
- 125000001424 substituent group Chemical group 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 23
- 239000007789 gas Substances 0.000 description 22
- 229910052763 palladium Inorganic materials 0.000 description 20
- 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 19
- 238000004519 manufacturing process Methods 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 17
- 125000000623 heterocyclic group Chemical group 0.000 description 17
- 125000001153 fluoro group Chemical group F* 0.000 description 16
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 16
- 229910052731 fluorine Inorganic materials 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 229910052786 argon Inorganic materials 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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- 229910001873 dinitrogen Inorganic materials 0.000 description 11
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- 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 10
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 10
- 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 9
- 229940126062 Compound A Drugs 0.000 description 9
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 9
- 238000006069 Suzuki reaction reaction Methods 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 0 CC(*1)=NC2=C1*(*)C1=C2*(*)C(C)=C1* Chemical compound CC(*1)=NC2=C1*(*)C1=C2*(*)C(C)=C1* 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000006619 Stille reaction Methods 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 239000004327 boric acid Substances 0.000 description 8
- 229910003472 fullerene Inorganic materials 0.000 description 8
- 125000000547 substituted alkyl group Chemical group 0.000 description 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 238000002835 absorbance Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 230000005669 field effect Effects 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000003107 substituted aryl group Chemical group 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 6
- 239000013076 target substance Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
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- 229940125898 compound 5 Drugs 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000031700 light absorption Effects 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 5
- 125000005415 substituted alkoxy group Chemical group 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 4
- 125000006539 C12 alkyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 125000001626 borono group Chemical group [H]OB([*])O[H] 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
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- 150000002739 metals Chemical class 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
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- 125000005338 substituted cycloalkoxy group Chemical group 0.000 description 4
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- 229910052718 tin Inorganic materials 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 3
- 125000005917 3-methylpentyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
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- 125000003368 amide group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001204 arachidyl group Chemical group [H]C([*])([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])C([H])([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])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
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- 125000004659 aryl alkyl thio group Chemical group 0.000 description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
- 125000005015 aryl alkynyl group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 238000007611 bar coating method Methods 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000002704 decyl 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])C([H])([H])C([H])([H])* 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 3
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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 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 3
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 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 3
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011574 phosphorus Chemical group 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PWLCTAFCDZYKEF-UHFFFAOYSA-N triphenyl arsorite Chemical compound C=1C=CC=CC=1O[As](OC=1C=CC=CC=1)OC1=CC=CC=C1 PWLCTAFCDZYKEF-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/151—Copolymers
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- C08G2261/1412—Saturated aliphatic units
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- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/146—Side-chains containing halogens
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- C08G2261/3245—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing nitrogen and oxygen as heteroatoms
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
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- C08G2261/90—Applications
- C08G2261/91—Photovoltaic applications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G2261/90—Applications
- C08G2261/92—TFT applications
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/403—Cells and electrode assemblies
- G01N27/414—Ion-sensitive or chemical field-effect transistors, i.e. ISFETS or CHEMFETS
- G01N27/4141—Ion-sensitive or chemical field-effect transistors, i.e. ISFETS or CHEMFETS specially adapted for gases
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- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02S—GENERATION OF ELECTRIC POWER BY CONVERSION OF INFRARED RADIATION, VISIBLE LIGHT OR ULTRAVIOLET LIGHT, e.g. USING PHOTOVOLTAIC [PV] MODULES
- H02S40/00—Components or accessories in combination with PV modules, not provided for in groups H02S10/00 - H02S30/00
- H02S40/30—Electrical components
- H02S40/38—Energy storage means, e.g. batteries, structurally associated with PV modules
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
- H10K10/488—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising a layer of composite material having interpenetrating or embedded materials, e.g. a mixture of donor and acceptor moieties, that form a bulk heterojunction
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
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- H10K39/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic radiation-sensitive element covered by group H10K30/00
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
- H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
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- 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
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- 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
- Y02E70/00—Other energy conversion or management systems reducing GHG emissions
- Y02E70/30—Systems combining energy storage with energy generation of non-fossil origin
Definitions
- the present invention relates to a compound and an organic photoelectric conversion element and an organic thin film transistor using the compound.
- Patent Document 1 a polymer compound composed of a repeating unit (A) and a repeating unit (B) is known (Patent Document 1).
- an organic thin film solar cell containing an organic layer containing the polymer compound is not necessarily sufficiently high in photoelectric conversion efficiency.
- An object of the present invention is to provide a compound capable of producing an organic thin film solar cell with high photoelectric conversion efficiency.
- X 1 , X 2 , X 3 and X 4 are the same or different and represent a nitrogen atom or ⁇ CH—.
- Y 1 and Y 2 are the same or different and each represents a sulfur atom, an oxygen atom, a selenium atom, —N (R 1 ) — or —CR 2 ⁇ CR 3 —.
- R 1 , R 2 and R 3 are the same or different and each represents a hydrogen atom, a halogen atom, an amino group, a cyano group or a monovalent organic group.
- W 1 and W 3 are the same or different and represent a halogen atom, a cyano group, or a monovalent organic group.
- W 2 and W 4 are the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, or a monovalent organic group.
- the structural unit represented by Formula (1) and the structural unit represented by Formula (2) are not the same.
- [2] The compound according to [1], wherein Y 1 and Y 2 are not the same.
- [3] The compound according to [1] or [2], wherein W 1 , W 2 , W 3 and W 4 are all halogen atoms.
- [4] The compound according to any one of [1] to [3], further having a structural unit represented by formula (3).
- Ar 1 represents an arylene group or a heteroarylene group.
- [5] The compound according to [4], wherein Ar 1 is a heteroarylene group.
- [6] The compound according to [4] or [5], wherein the heteroarylene group is a group containing a thiophene ring.
- [7] The compound according to any one of [1] to [6], which is a polymer compound.
- [8] The polymer compound according to [7], which has a polystyrene-equivalent weight average molecular weight of 3 ⁇ 10 3 or more.
- the organic photoelectric conversion element containing the compound as described in any one, or the high molecular compound as described in [7] or [8].
- a sensor comprising the compound according to any one of [1] to [6] or the polymer compound according to [7] or [8].
- the compound of the present invention has a structural unit represented by the following formula (1) and a structural unit represented by the formula (2).
- Formula (1) and Formula (2) are not the same structures.
- X 1 , X 2 , X 3 and X 4 are the same or different and represent a nitrogen atom or ⁇ CH—.
- X 1 , X 2 , X 3 and X 4 are preferably nitrogen atoms.
- Y 1 is preferably a sulfur atom, an oxygen atom, or —N (R 1 ) —, more preferably a sulfur atom or an oxygen atom, and still more preferably an oxygen atom.
- Y 2 represents any of a sulfur atom, an oxygen atom, a selenium atom, —N (R 1 ) — or —CR 2 ⁇ CR 3 —.
- Y 2 is preferably a sulfur atom, an oxygen atom, or —N (R 1 ) —, more preferably a sulfur atom or an oxygen atom, and still more preferably a sulfur atom.
- Y 1 and Y 2 may be the same, but different ones are preferable from the viewpoint of increasing the photoelectric conversion efficiency. When Y 1 and Y 2 are different from each other, it is preferable that one of Y 1 and Y 2 is a sulfur atom and the other is an oxygen atom.
- R 1 , R 2 and R 3 are the same or different and each represents a hydrogen atom, a halogen atom, an amino group, a cyano group or a monovalent organic group.
- R 1 is preferably a hydrogen atom or a monovalent organic group.
- Examples of the monovalent organic group include an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkoxy group, an optionally substituted cycloalkoxy group, and a substituted An optionally substituted alkylthio group, an optionally substituted cycloalkylthio group, an optionally substituted aryl group, an optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted aryl Alkyl group, arylalkoxy group which may be substituted, arylalkylthio group which may be substituted, acyl group, acyloxy group, amide group, imide group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group Substituted silylamino group, monovalent heterocyclic group, heterocyclic oxy group, heterocyclic thio group, arylal It represents a group, aryl
- the alkyl group which may be substituted may be linear or branched.
- the alkyl group usually has 1 to 30 carbon atoms.
- the alkyl group may be substituted, and examples of the substituent include a halogen atom.
- a halogen atom is preferably a fluorine atom.
- alkyl group which may be substituted include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl tomb, pentyl group, isopentyl group, 2- Methylbutyl group, 1-methylbutyl group, hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, 3,7- Examples include dimethyloctyl group, nonyl group, decyl group, undecyl group, dodecyl group, tetradecyl group, hexadecyl grave, octadecyl group, and eicosyl group.
- the cycloalkyl group usually has 3 to 30 carbon atoms.
- the cycloalkyl group may be substituted, and examples of the substituent include a halogen atom and an alkyl group (for example, having 1 to 20 carbon atoms).
- a halogen atom a fluorine atom is preferable.
- Two or more alkyl groups substituted on a cycloalkyl group may be linked to each other to form a cyclic structure together with the carbon atoms to which they are bonded.
- Specific examples of the optionally substituted cycloalkyl group include a cyclopentyl group, a cyclohexyl group, and an adamantyl group.
- the alkyl part of the alkoxy group may be linear or branched.
- the alkoxy group may have a substituent.
- the carbon number of the alkoxy group is usually 1-20.
- the alkoxy group may be substituted, and examples of the substituent include a halogen atom and an alkoxy group (for example, having 1 to 20 carbon atoms) and a cycloalkoxy group (for example, having 3 to 20 carbon atoms).
- a halogen atom for example, having 1 to 20 carbon atoms
- a cycloalkoxy group for example, having 3 to 20 carbon atoms.
- the optionally substituted alkoxy group include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, Octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, trifluoromethoxy group, pentafluoroethoxy group, perfluorobutoxy group, perfluorohexyloxy group, A perfluorooctyloxy group, a methoxymethyloxy group and a 2-methoxyethyloxy group can be mentioned.
- the cycloalkoxy group usually has 3 to 20 carbon atoms.
- the cycloalkoxy group may be substituted, and examples of the substituent include a halogen atom, an alkoxy group (eg, having 1 to 20 carbon atoms), and a cycloalkoxy group (eg, having 3 to 20 carbon atoms).
- a halogen atom a fluorine atom is preferable.
- the optionally substituted cycloalkoxy group include a cyclopentyloxy group and a cyclohexyloxy group.
- the alkyl part of the alkylthio group may be linear or branched.
- the alkylthio group usually has 1 to 20 carbon atoms.
- the alkylthio group may be substituted, and examples of the substituent include a halogen atom.
- a halogen atom As the halogen atom, a fluorine atom is preferable.
- alkylthio group which may be substituted include methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, tert-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group.
- the cycloalkylthioalkylthio group has 3 to 20 carbon atoms.
- the cycloalkylthio group may be substituted, and examples of the substituent include a halogen atom.
- a halogen atom As the halogen atom, a fluorine atom is preferable.
- An aryl group means a group obtained by removing one hydrogen atom on an aromatic ring from an aromatic hydrocarbon, and usually has 6 to 60 carbon atoms.
- the aryl group may be substituted, and examples of the substituent include a halogen atom, an alkoxy group (for example, having 1 to 20 carbon atoms), and a cycloalkoxy group (for example, having 3 to 20 carbon atoms).
- a halogen atom a fluorine atom is preferable.
- the aryl group which may be substituted include a phenyl group, a C1 to C12 alkoxyphenyl group (C1 to C12 alkoxy represents an alkoxy having 1 to 12 carbon atoms), and a C1 to C12 alkylphenyl. And a group (C1 to C12 alkyl represents an alkyl having 1 to 12 carbon atoms), 1-naphthyl group, 2-naphthyl group, and pentafluorophenyl group.
- a preferred embodiment is a C1-C8 alkoxyphenyl group
- a more preferred embodiment is a C1-C6 alkoxyphenyl group.
- Specific examples of C1 to C8 alkoxy and C1 to C6 alkoxy include those of C1 to C8 and C1 to C6 among the alkoxys exemplified for the above alkoxy group.
- the aryloxy group usually has 6 to 60 carbon atoms.
- the aryl moiety may be substituted, and examples of the substituent include a halogen atom, an alkoxy group (eg, having 1 to 20 carbon atoms), and a cycloalkoxy group (eg, having 3 to 20 carbon atoms).
- Specific examples of the optionally substituted aryloxy group include a phenoxy group, a C1-C12 alkoxyphenoxy group, a C1-C12 alkylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and a pentafluorophenoxy group. It is done.
- the arylthio group usually has 6 to 60 carbon atoms.
- the aryl moiety may be substituted, and examples of the substituent include a halogen atom, an alkoxy group (eg, having 1 to 20 carbon atoms), and a cycloalkoxy group (eg, having 3 to 20 carbon atoms).
- Specific examples of the arylthio group which may be substituted include a phenylthio group, a C1-C12 alkoxyphenylthio group, a C1-C12 alkylphenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, and a pentafluorophenylthio group. It is done.
- the arylalkyl group usually has 7 to 60 carbon atoms.
- the aryl moiety may be substituted, and examples of the substituent include a halogen atom and an alkoxy group (eg, having 1 to 20 carbon atoms) and a cycloalkoxy group (eg, having 3 to 20 carbon atoms).
- Specific examples of the optionally substituted arylalkyl group include a phenyl-C1 to C12 alkyl group, a C1 to C12 alkoxyphenyl-C1 to C12 alkyl group, a C1 to C12 alkylphenyl-C1 to C12 alkyl group, and 1-naphthyl. -C1-C12 alkyl group and 2-naphthyl-C1-C12 alkyl group are mentioned.
- the arylalkoxy group usually has 7 to 60 carbon atoms.
- the aryl moiety may be substituted, and examples of the substituent include a halogen atom and an alkoxy group (eg, having 1 to 20 carbon atoms) and a cycloalkoxy group (eg, having 3 to 20 carbon atoms).
- Specific examples of the optionally substituted arylalkoxy group include a phenyl-C1 to C12 alkoxy group, a C1 to C12 alkoxyphenyl-C1 to C12 alkoxy group, a C1 to C12 alkylphenyl-C1 to C12 alkoxy group, and 1-naphthyl. -C1-C12 alkoxy group and 2-naphthyl-C1-C12 alkoxy group are mentioned.
- the arylalkylthio group usually has 7 to 60 carbon atoms.
- the aryl moiety may be substituted, and examples of the substituent include a halogen atom and an alkoxy group (eg, having 1 to 20 carbon atoms) and a cycloalkoxy group (eg, having 3 to 20 carbon atoms).
- Specific examples of the optionally substituted arylalkylthio group include phenyl-C1-C12 alkylthio group, C1-C12 alkoxyphenyl-C1-C12 alkylthio group, C1-C12 alkylphenyl-C1-C12 alkylthio group, and 1-naphthyl. -C1-C12 alkylthio group and 2-naphthyl-C1-C12 alkylthio group are mentioned.
- Acyl group means a group obtained by removing a hydroxyl group from a carboxyl group (—COOH) of a carboxylic acid, and usually has 2 to 20 carbon atoms.
- Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pivaloyl group, a trifluoroacetyl group, an alkylcarbonyl group which may be substituted with a halogen having 2 to 20 carbon atoms, a benzoyl group, Examples thereof include a phenylcarbonyl group which may be substituted with a halogen such as a pentafluorobenzoyl group.
- Acyloxy group means a group obtained by removing a hydrogen atom from a carboxyl group (—COOH) of a carboxylic acid, and usually has 2 to 20 carbon atoms.
- Specific examples of the acyloxy group include an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, a benzoyloxy group, a trifluoroacetyloxy group, and a pentafluorobenzoyloxy group.
- An amide group means a group obtained by removing one hydrogen atom bonded to a nitrogen atom from an amide, and the carbon number is usually 2 to 20.
- Specific examples of the amide group include a formamide group, an acetamide group, a propioamide group, a butyroamide group, a benzamide group, a trifluoroacetamide group, a pentafluorobenzamide group, a diformamide group, a diacetamide group, a dipropioamide group, a dibutyroamide group, and a dibenzamide group. , Ditrifluoroacetamide group and dipentafluorobenzamide group.
- An imide group means a group obtained by removing one hydrogen atom bonded to a nitrogen atom from an imide, and specific examples include a succinimide group and a phthalimide group.
- the carbon number of the imide group is usually 2-20.
- the substituted amino group is one in which one or two hydrogen atoms of the amino group are substituted with a substituent.
- the substituents are, for example, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, and an optionally substituted aryl group.
- Specific examples of the optionally substituted alkyl group, the optionally substituted cycloalkyl group, and the optionally substituted aryl group include an optionally substituted alkyl group represented by R 1 , Specific examples of the cycloalkyl group which may be substituted and the aryl group which may be substituted are the same.
- the substituted amino group usually has 1 to 40 carbon atoms.
- substituted amino group examples include methylamino group, dimethylamino group, ethylamino group, diethylamino group, propylamino group, dipropylamino group, isopropylamino group, diisopropylamino group, butylamino group, isobutylamino group, tert -Butylamino group, pentylamino group, hexylamino group, cyclohexylamino group, heptylamino group, octylamino group, 2-ethylhexylamino group, nonylamino group, decylamino group, 3,7-dimethyloctylamino group, laurylamino group, Cyclopentylamino group, dicyclopentylamino group, cyclohexylamino group, dicyclohexylamino group, pyrrolidyl group, piperidyl
- a substituted silyl group is one in which one, two, or three of the hydrogen atoms of the silyl group are substituted with a substituent, and in general, all three hydrogen atoms of the silyl group are substituted.
- an alkyl group that may be substituted a cycloalkyl group that may be substituted, and an aryl group that may be substituted.
- Specific examples of the optionally substituted alkyl group, the optionally substituted cycloalkyl group, and the optionally substituted aryl group include an optionally substituted alkyl group represented by R 1 , Specific examples of the cycloalkyl group which may be substituted and the aryl group which may be substituted are the same.
- the carbon number of the substituted silyl group is usually 1 to 36.
- Specific examples of the substituted silyl group include trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, tert-butyldimethylsilyl group, triphenylsilyl group, tri-p-xylylsilyl group, tribenzylsilyl group, Examples include a diphenylmethylsilyl group, a tert-butyldiphenylsilyl group, and a dimethylphenylsilyl group.
- the substituted silyloxy group is a group in which an oxygen atom is bonded to the above substituted silyl group, and examples of the substituent include the substituents exemplified for the substituted silyl group.
- the carbon number of the substituted silyloxy group is usually 1 to 36.
- Specific examples of the substituted silyloxy group include trimethylsilyloxy group, triethylsilyloxy group, tripropylsilyloxy group, triisopropylsilyloxy group, tert-butyldimethylsilyloxy group, triphenylsilyloxy group, tri-p-xylyl group.
- Examples thereof include a silyloxy group, a tribenzylsilyloxy group, a diphenylmethylsilyloxy group, a tert-butyldiphenylsilyloxy group, and a dimethylphenylsilyloxy group.
- the substituted silylthio group is a group in which a sulfur atom is bonded to the above substituted silyl group, and examples of the substituent include the substituents exemplified for the substituted silyl group.
- the carbon number of the substituted silylthio group is usually 1 to 36.
- Specific examples of the substituted silylthio group include trimethylsilylthio group, triethylsilylthio group, tripropylsilylthio group, triisopropylsilylthio group, tert-butyldimethylsilylthio group, triphenylsilylthio group, and tri-p-xylyl.
- Examples thereof include a silylthio group, a tribenzylsilylthio group, a diphenylmethylsilylthio group, a tert-butyldiphenylsilylthio group, and a dimethylphenylsilylthio group.
- the substituted silylamino group is one in which one or two hydrogen atoms of the amino group are substituted with a substituted silyl group, and the substituted silyl group is as described above.
- the substituted silylamino group usually has 1 to 36 carbon atoms.
- Specific examples of the substituted silylamino group include trimethylsilylamino group, triethylsilylamino group, tripropylsilylamino group, triisopropylsilylamino group, tert-butyldimethylsilylamino group, triphenylsilylamino group, tri-p-xylyl.
- the monovalent heterocyclic group may be substituted.
- a monovalent heterocyclic group is a group obtained by removing one hydrogen atom from a heterocyclic compound.
- Heterocyclic compounds include furan, thiophene, pyrrole, pyrroline, pyrrolidine, oxazole, isoxazole, thiazole, isothiazole, imidazole, imidazoline, imidazolidine, pyrazole, pyrazoline, prazolidine, furazane, triazole, thiadiazole, oxadiazole, tetrazole , Pyran, pyridine, piperidine, thiopyran, pyridazine, pyrimidine, pyrazine, piperazine, morpholine, triazine, benzofuran, isobenzofuran, benzothiophene, indole, isoindole, indolizine, indoline, isoind
- heterocyclic oxy group examples include a group represented by the formula (D) in which an oxygen atom is bonded to the monovalent heterocyclic group.
- heterocyclic thio group examples include a group represented by the formula (E) in which a sulfur atom is bonded to the above monovalent heterocyclic group.
- Ar 7 represents a monovalent heterocyclic group.
- the heterocyclic oxy group usually has 4 to 60 carbon atoms.
- heterocyclic oxy group examples include thienyloxy group, C1-C12 alkylthienyloxy group, pyrrolyloxy group, furyloxy group, pyridyloxy group, C1-C12 alkylpyridyloxy group, imidazolyloxy group, pyrazolyloxy group, triazolyl group. And a ruoxy group, an oxazolyloxy group, a thiazoleoxy group, and a thiadiazoleoxy group.
- the heterocyclic thio group usually has 4 to 60 carbon atoms.
- Specific examples of the heterocyclic thio group include thienyl mercapto group, C1-C12 alkyl thienyl mercapto group, pyrrolyl mercapto group, furyl mercapto group, pyridyl mercapto group, C1-C12 alkyl pyridyl mercapto group, imidazolyl mercapto group, pyrazolyl mercapto group. , Triazolyl mercapto group, oxazolyl mercapto group, thiazole mercapto group and thiadiazole mercapto group.
- the arylalkenyl group usually has 8 to 20 carbon atoms, and specific examples of the arylalkenyl group include a styryl group.
- the arylalkynyl group usually has 8 to 20 carbon atoms, and specific examples of the arylalkynyl group include a phenylacetylenyl group.
- R 1 , R 2 and R 3 are preferably an alkyl group, an aryl group or an arylalkyl group.
- W 1 and W 3 are the same or different and each represent a halogen atom, a cyano group, or a monovalent organic group.
- the definition and specific examples of the monovalent organic group are the same as the definition and specific examples of the monovalent organic group described in the above R 1 , R 2 and R 3 .
- W 1 and W 3 are preferably a monovalent organic group or a halogen atom, more preferably a monovalent organic group having a halogen atom or a halogen atom, and still more preferably a halogen atom.
- the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferable.
- W 2 and W 4 are the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, or a monovalent organic group.
- the definition and specific examples of the monovalent organic group are the same as the definition and specific examples of the monovalent organic group described in the above R 1 , R 2 and R 3 .
- Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- W 2 and W 4 are preferably a monovalent organic group, a halogen atom or a hydrogen atom, more preferably a monovalent organic group having a halogen atom, a halogen atom or a hydrogen atom, still more preferably a halogen atom or a hydrogen atom.
- the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferable.
- W 1 , W 2 , W 3 and W 4 are preferably all halogen atoms, and more preferably all are fluorine atoms.
- R 2 and R 3 represent the same meaning as described above. Among the above, it is preferably 1-1 to 1-6, more preferably 1-1 or 1-2, and still more preferably 1-1.
- R 2 and R 3 represent the same meaning as described above. Among the above, it is preferably 2-1 to 2-6, more preferably 2-1 or 2-2, and further preferably 2-2.
- the compound of the present invention may have a structure represented by the formula (3) in addition to the above formulas (1) and (2).
- Ar 1 represents an arylene group or a heteroarylene group.
- the arylene group is an atomic group obtained by removing two hydrogen atoms from an optionally substituted aromatic hydrocarbon.
- the number of carbon atoms constituting the aromatic ring contained in the arylene group is usually about 6 to 60, and preferably 6 to 20.
- Aromatic hydrocarbons include those having a benzene ring, those having a condensed ring, those having two or more independent benzene rings or two or more condensed rings directly bonded, or those bonded via a group such as vinylene.
- the heteroarylene group is an atomic group obtained by removing two hydrogen atoms from an optionally substituted aromatic heterocyclic compound.
- the number of carbon atoms constituting the aromatic ring contained in the heteroarylene group is usually about 2 to 60, preferably 3 to 20.
- An aromatic heterocyclic compound is an organic compound having an aromatic cyclic structure, and the elements constituting the ring are not only carbon atoms, but also heteroatoms such as oxygen, sulfur, nitrogen, phosphorus, boron, arsenic, and silicon. Is included in the ring.
- Ar 1 is preferably a heteroarylene group, and more preferably a heteroarylene group containing a thiophene ring.
- Two or more structural units represented by the formula (3) may be present continuously in the compound of the present invention, or the formula (1) is present on both sides of the structural unit represented by the formula (3). ) And / or a structural unit represented by formula (2) may be present. When two or more are present in succession, the structural units represented by the formula (3) present in succession may be the same or different from each other.
- ring d represents an optionally substituted aromatic carbocyclic ring or an optionally substituted aromatic heterocyclic ring.
- m represents an integer of 1 or more.
- Z is a group represented by formula (z-1) to formula (z-8). When there are a plurality of d rings, they may be the same or different. When there are a plurality of Z, they may be the same or different.
- R represents a hydrogen atom, a halogen atom, an amino group, a cyano group, or a monovalent organic group. The two R's may be linked together to form a cyclic structure together with the carbon atoms to which they are bonded.
- Aromatic heterocycles include furan ring, thiophene ring, pyrrole ring, silole ring, borole ring, phosphole ring, imidazole ring, triazole ring, thiazole ring, oxazole ring, isoxazole ring, pyrazole ring, isothiazole ring, pyridine ring , Pyrazine ring, pyrimidine ring, quinoline ring, isoquinoline ring, indole ring, benzofuran ring, isobenzofuran ring, benzimidazole ring, benzothiophene ring, benzothiazole ring, benzoxazole ring and the like.
- M represents an integer of 1 or more. Preferably, it is 1 to 3, more preferably 1 to 2, and still more preferably 1.
- Examples of the monovalent organic group represented by R include the same groups as the monovalent organic group represented by R 1 described above.
- R is preferably an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkoxy group, an optionally substituted alkoxy group, or an optionally substituted aryl.
- Group, an optionally substituted aryloxy group, more preferably an optionally substituted alkyl group having 9 to 18 carbon atoms, and an optionally substituted cycloalkyl group having 9 to 18 carbon atoms An optionally substituted alkoxy group having 9 to 18 carbon atoms, an optionally substituted cycloalkoxy group having 9 to 18 carbon atoms, an optionally substituted aryl group having 9 to 18 carbon atoms, An aryloxy group having 9 to 18 carbon atoms which may be substituted, and more preferably an alkyl group having 9 to 18 carbon atoms.
- the aromatic carbocycle and the aromatic heterocycle may have a substituent.
- the aromatic carbocycle or the aromatic heterocycle has two or more substituents, the substituents may be connected to each other to form a cyclic structure together with the carbon atoms to which they are bonded.
- the substituent that the aromatic carbocycle and aromatic heterocycle may have include the same groups as the halogen atom, amino group, cyano group, or monovalent organic group represented by R 1 described above.
- e ring represents a monocyclic aromatic carbocyclic ring which may be substituted or a monocyclic aromatic heterocyclic ring which may be substituted.
- n represents an integer of 1 or more.
- p represents an integer of 0 to 5. When there are a plurality of e-rings, they may be the same or different.
- n represents an integer of 1 or more. Preferably, it is 1 to 4, more preferably 1 to 3, and still more preferably 1 to 2.
- p represents an integer of 0 to 5. The number is preferably 0 to 4, more preferably 0 to 3, and still more preferably 0 to 2.
- the substituent that the monocyclic aromatic carbocycle and the monocyclic aromatic heterocycle may have is the same as the substituent that the aromatic carbocycle or aromatic heterocycle in the d ring may have. Groups.
- the compound of the present invention is used for an organic thin film transistor, from the viewpoint of increasing hole mobility, among structural units represented by formula (D-1) to formula (D-5),
- the structural unit represented by the structural unit represented by Formula (D-4) is preferable, and the structural unit represented by Formula (D-1) is more preferable.
- Examples of the structural unit represented by the formula (D-1) include groups represented by the formulas 1 to 152.
- R represents the same meaning as described above.
- Examples of the structural unit represented by Formula (D-3) include groups represented by Formula 201 to Formula 234.
- R represents the same meaning as described above.
- Examples of the structural unit represented by formula (D-4) include groups represented by formula 235 to formula 238.
- R represents the same meaning as described above.
- Examples of the structural unit represented by Formula (D-5) include groups represented by Formula 301 to Formula 323.
- R represents the same meaning as described above.
- the compound of the present invention may have a group in which structural units represented by two or more formulas (D-1) to (D-5) are bonded.
- Examples of the group include groups represented by formulas 401 to 414.
- a and b are the same or different and represent an integer of 1 to 5. Preferably it is 1 to 3, more preferably 1.
- R represents the same meaning as described above.
- Formula 401 to Formula 414 When using the compound of the present invention as a material for a photoelectric conversion element, from the viewpoint of increasing the photoelectric conversion efficiency, among the groups represented by Formula 401 to Formula 414, Formula 401, Formula 402, Formula 409, Formula 410, Formula 411, Formula 412, Formula 413, and Formula 414 are preferable, Formula 401, Formula 409, Formula 413, and Formula 414 are more preferable, and Formula 401 and Formula 409 are further groups. preferable.
- the ratio of the number of structural units represented by the formula (1) and the number of structural units represented by the formula (2) in the compound of the present invention is as follows. From the viewpoint of increasing the photoelectric conversion efficiency, the numerical value of P represented by the following formula is preferably 0.1 to 0.9, more preferably 0.2 to 0.8, 0.4 Is more preferably from 0.8 to 0.8, particularly preferably from 0.5 to 0.8.
- the compound of the present invention has a structural unit represented by the formula (3)
- the number of structural units represented by the formula (1) in the compound of the present invention and the structural unit represented by the formula (2) From the viewpoint of increasing the solubility of the compound of the present invention in the solvent, the sum of the numbers and the ratio of the number of structural units represented by the formula (3) are as follows. It is preferably 10 to 0.80, more preferably 0.15 to 0.60, and still more preferably 0.20 to 0.50.
- the compound of the present invention is preferably a polymer compound from the viewpoint of increasing the photoelectric conversion efficiency.
- the polymer compound in the present invention refers to a compound having a polystyrene-equivalent number average molecular weight of 1000 or more measured by gel permeation chromatography (hereinafter sometimes referred to as GPC).
- the number average molecular weight in terms of polystyrene of the polymer compound of the present invention is preferably 2,000 to 1,000,000, more preferably 2500 to 1,000,000, and further preferably 3,000 to 100,000.
- the structural unit represented by the formula (1) in the polymer compound of the present invention only needs to be contained in the compound.
- the polymer compound contains an average of 2 or more per polymer chain, more preferably an average of 3 or more per polymer chain.
- At least one structural unit represented by the formula (2) in the polymer compound of the present invention may be contained in the compound.
- the polymer compound contains an average of 2 or more per polymer chain, more preferably an average of 3 or more per polymer chain.
- the polymer compound of the present invention is preferably a ⁇ -conjugated polymer compound.
- the ⁇ -conjugated polymer compound refers to a polymer compound in which multiple bonds exist with a single bond between them in the main chain.
- One preferred embodiment of the compounds of the present invention is a compound structural units the structural unit represented by the formula (1) (Y 1 is a sulfur atom) represented by formula (2) and (Y 2 is an oxygen atom) and a.
- P ′ defined by the following formula is preferably 0.1 to 0.9, more preferably 0.2 to 0.8, and preferably 0.4 to 0.8. More preferable. Particularly preferred is 0.5 to 0.8.
- S ′ ⁇ (number of structural units represented by formula (1) (Y 1 is a sulfur atom)) + (number of structural units represented by formula (2) (Y 2 is an oxygen atom)) ⁇ / ⁇ (Number of structural units represented by Formula (1) (Y 1 is a sulfur atom))) + (Number of structural units represented by Formula (2) (Y 2 is an oxygen atom)) + (Formula (3) Number of structural units represented by
- the solubility in a solvent is high in terms of ease of device production.
- the compound of the present invention has a solubility capable of producing a solution containing 0.01% by weight or more of the compound, and a solubility capable of producing a solution containing 0.1% by weight or more. It is more preferable to have a solubility capable of producing a solution containing 0.4 wt% or more.
- the method for producing the compound of the present invention is not particularly limited, but a method using a Suzuki coupling reaction or a Stille coupling reaction is preferable from the viewpoint of ease of synthesis of the compound.
- E 1 is preferably an arylene group or a heteroarylene group, and more preferably a group represented by the above formulas 1 to 255.
- the total number of moles of one or more compounds represented by formula (200) used in the reaction is excessive with respect to the total number of moles of one or more compounds represented by formula (100). Is preferred.
- the total number of moles of one or more compounds represented by the formula (200) used in the reaction is 1 mole, the total number of moles of the one or more compounds represented by the formula (100) is 0.6-0.
- the amount is preferably 99 mol, more preferably 0.7 to 0.95 mol.
- the boric acid ester residue means a group obtained by removing a hydroxyl group from a boric acid diester, and examples thereof include a dialkyl ester residue, a diaryl ester residue, and a di (arylalkyl) ester residue.
- Specific examples of the boric acid ester residue include the following formula: (In the formula, Me represents a methyl group, and Et represents an ethyl group.) The group represented by these is illustrated.
- Examples of the halogen atom represented by T 1 and T 2 in Formula (200) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- a bromine atom and an iodine atom are preferable, and a bromine atom is more preferable.
- the sulfonic acid residue represented by T 1 and T 2 means an atomic group obtained by removing acidic hydrogen from sulfonic acid (—SO 3 H), and specific examples include an alkyl sulfonate group.
- alkyl sulfonate group for example, methanesulfonate group, ethanesulfonate group), arylsulfonate group (for example, benzenesulfonate group, p-toluenesulfonate group), arylalkylsulfonate group (for example, benzylsulfonate group) and trifluoromethanesulfonate group.
- the method for carrying out the Suzuki coupling reaction includes a method in which a palladium catalyst is used as a catalyst in an arbitrary solvent and the reaction is carried out in the presence of a base.
- Examples of the palladium catalyst used in the Suzuki coupling reaction include a Pd (0) catalyst and a Pd (II) catalyst.
- a Pd (0) catalyst examples include a Pd (0) catalyst and a Pd (II) catalyst.
- the addition amount of the palladium catalyst is not particularly limited as long as it is an effective amount as a catalyst, but is usually 0.0001 mol to 0.5 mol with respect to 1 mol of the compound represented by the formula (100). The amount is preferably 0.0003 mol to 0.1 mol.
- a phosphorus compound such as triphenylphosphine, tri (o-tolyl) phosphine, tri (o-methoxyphenyl) phosphine is added as a ligand.
- the addition amount of the ligand is usually 0.5 mol to 100 mol, preferably 0.9 mol to 20 mol, more preferably 1 mol to 10 mol with respect to 1 mol of the palladium catalyst. is there.
- Examples of the base used for the Suzuki coupling reaction include inorganic bases, organic bases, inorganic salts and the like.
- examples of the inorganic base include potassium carbonate, sodium carbonate, and barium hydroxide.
- examples of the organic base include triethylamine and tributylamine.
- An example of the inorganic salt is cesium fluoride.
- the amount of the base added is usually 0.5 mol to 100 mol, preferably 0.9 mol to 20 mol, more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by the formula (100). is there.
- the Suzuki coupling reaction is usually performed in a solvent.
- the solvent include N, N-dimethylformamide, toluene, dimethoxyethane, and tetrahydrofuran. From the viewpoint of solubility of the polymer compound used in the present invention, toluene and tetrahydrofuran are preferred.
- the base may be added as an aqueous solution and reacted in a two-phase system.
- an inorganic salt is used as the base, it is usually added as an aqueous solution and reacted from the viewpoint of solubility of the inorganic salt.
- phase transfer catalysts such as a quaternary ammonium salt
- the temperature at which the Suzuki coupling reaction is carried out depends on the solvent, but is usually about 50 to 160 ° C., and 60 to 120 ° C. is preferable from the viewpoint of increasing the molecular weight of the polymer compound. Alternatively, the temperature may be raised to near the boiling point of the solvent and refluxed.
- the reaction time may be reached when the target degree of polymerization is reached, but is usually about 0.1 to 200 hours. About 1 hour to 30 hours is efficient and preferable.
- the Suzuki coupling reaction is performed in a reaction system in which the Pd (0) catalyst is not deactivated under an inert atmosphere such as argon gas or nitrogen gas.
- an inert atmosphere such as argon gas or nitrogen gas.
- it is performed in a system sufficiently deaerated with argon gas or nitrogen gas.
- the compound represented by the formula (100), the compound represented by the formula (200), Dichlorobis (triphenylphosphine) palladium (II) was charged, the polymerization vessel was sufficiently replaced with nitrogen gas, degassed, and then degassed by adding a degassed solvent such as toluene by bubbling with nitrogen gas in advance.
- a base degassed by bubbling with nitrogen gas in advance for example, an aqueous sodium carbonate solution
- nitrogen gas in advance for example, an aqueous sodium carbonate solution
- E 3 is preferably an arylene group or a heteroarylene group, more preferably a group represented by the above formulas 1 to 255.
- Examples of the substituted stannyl group include a group represented by —SnR 100 3 .
- R 100 represents a monovalent organic group.
- Examples of the monovalent organic group include an alkyl group, a cycloalkyl group, and an aryl group.
- the carbon number of the alkyl group is usually 1 to 30, and specific examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl grave, n-pentyl group, isopentyl group, 2-methylbutyl group, 1-methylbutyl group, n-hexyl group, isohexyl group, 3-methylpentyl group, 21-methylpentyl group, 1-methylpentyl group, heptyl group, octyl group, Examples include isooctyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group, dodecyl group, tetradecyl group, hexadecyl tomb, octadecyl group, eicosyl group and the like.
- the cycloalkyl group usually has 3 to 30 carbon atoms, and specific examples thereof include a cyclopentyl group, a cyclohexyl group, and an adamantyl group.
- the aryl group include a phenyl group and a naphthyl group.
- Substituted stannyl preferably -SnMe 3 as a base, -SnEt 3, -SnBu 3, an -SnPh 3, more preferably -SnMe 3, -SnEt 3, is -SnBu 3.
- Me represents a methyl group
- Et represents an ethyl group
- Bu represents a butyl group
- Ph represents a phenyl group.
- examples of the catalyst include a method of reacting in an arbitrary solvent under a palladium catalyst.
- examples of the palladium catalyst used in the Stille coupling reaction include a Pd (0) catalyst and a Pd (II) catalyst.
- Specific examples include palladium [tetrakis (triphenylphosphine)], palladium acetates, dichlorobis (triphenylphosphine) palladium, palladium acetate, tris (dibenzylideneacetone) dipalladium, and bis (dibenzylideneacetone) palladium.
- Palladium [tetrakis (triphenylphosphine)] and tris (dibenzylideneacetone) dipalladium are preferable from the viewpoints of easy reaction (polymerization) operation and reaction (polymerization) rate.
- the addition amount of the palladium catalyst used for the Stille coupling reaction is not particularly limited as long as it is an effective amount as a catalyst, but is usually 0.0001 per 1 mol of the compound represented by the formula (100). The amount is from mol to 0.5 mol, preferably from 0.0003 mol to 0.2 mol.
- a ligand or a cocatalyst can be used as necessary.
- the ligand include phosphorus such as triphenylphosphine, tri (o-tolyl) phosphine (that is, tris (2-tolyl) phosphine), tri (o-methoxyphenyl) phosphine, and tris (2-furyl) phosphine.
- arsenic compounds such as triphenylarsine and triphenoxyarsine.
- the cocatalyst include copper iodide, copper bromide, copper chloride, and copper (I) 2-thenoylate.
- the amount of ligand or promoter added is usually 0.5 to 100 moles, preferably 0.9 to 20 moles per mole of palladium catalyst. More preferably, it is 1 mol to 10 mol.
- the Stille coupling reaction is usually performed in a solvent.
- the solvent include N, N-dimethylformamide, N, N-dimethylacetamide, toluene, dimethoxyethane, tetrahydrofuran and the like. From the viewpoint of solubility of the polymer compound used in the present invention, toluene and tetrahydrofuran are preferred.
- the temperature at which the Stille coupling reaction is performed depends on the solvent, but is usually about 50 to 160 ° C., and preferably 60 to 120 ° C. from the viewpoint of increasing the molecular weight of the compound. Alternatively, the temperature may be raised to near the boiling point of the solvent and refluxed.
- the time for performing the reaction may be the end point when the target degree of polymerization is reached, but is usually about 0.1 to 200 hours. About 1 hour to 30 hours is efficient and preferable.
- the Stille coupling reaction is performed in a reaction system in which the Pd catalyst is not deactivated under an inert atmosphere such as argon gas or nitrogen gas.
- an inert atmosphere such as argon gas or nitrogen gas.
- the polymerization vessel is charged with a compound represented by the formula (300), a compound represented by the formula (200), A palladium catalyst is charged, and the polymerization vessel is sufficiently replaced with nitrogen gas, degassed, and then bubbled with nitrogen gas in advance to add a degassed solvent, for example, toluene, and then coordinate as necessary.
- the mixture is heated and heated, for example, and polymerized while maintaining an inert atmosphere at the reflux temperature for 8 hours.
- the polymerization active group may be protected with a stable group.
- the polymerization active group of the terminal group of the compound of the present invention is protected with a stable group, the characteristics and lifetime of the device using the compound of the present invention are hardly lowered.
- the stable group is preferably a group having a conjugated bond continuous with the conjugated structure of the main chain.
- the stable group may have a structure bonded to an aryl group or a heterocyclic group via a vinylene group.
- Examples of the stable group include a phenyl group having no substituent, a naphthyl group, a methyl group, an ethyl group, a propyl group, a butyl group, a trifluoromethyl group, and a pentafluoroethyl group.
- a smaller amount of the metal element contained in the compound of the present invention is preferable because photoelectric conversion efficiency and hole mobility are increased.
- the amount of the transition metal element contained in the compound of the present invention is small.
- the transition metal element include palladium, iron, tin, nickel, and copper. Especially, it is preferable that there are few amounts of palladium, iron, and tin.
- the amount of impurities contained in the compound of the present invention is measured by elemental analysis, but the total amount of palladium, iron and tin is preferably 1000 ppm or less, more preferably 500 ppm or less, and even more preferably 100 ppm or less. And particularly preferably 30 ppm or less. Elemental analysis methods include atomic absorption analysis, emission spectroscopy analysis, plasma emission analysis, fluorescent X-ray analysis, plasma mass analysis, glow discharge mass analysis, ion chromatograph analysis and the like.
- the compound of the present invention has a structural unit represented by the formula (1) and a structural unit represented by the formula (2).
- the compound can be synthesized, for example, by using the compound represented by the formula (4) and the compound represented by the formula (5) as an essential component of the raw material.
- X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , W 1 , W 2 , W 3 , W 4 represent the same meaning as described above.
- Q and Q 2 are the same or different and each represents a hydrogen atom, a halogen atom, a dihydroxyboryl group, or a monovalent organic group.
- Two Qs may be the same or different.
- Two Q 2 may be the same or different
- Y 1 is more preferably a sulfur atom, an oxygen atom, or —CR 2 ⁇ CR 3 —, and still more preferably a sulfur atom.
- Y 2 is more preferably a sulfur atom, an oxygen atom, or —CR 2 ⁇ CR 3 —, and still more preferably an oxygen atom.
- Examples of the monovalent organic group represented by Q or Q 2 include a substituted silyl group, a boric acid ester residue, and a substituted stannyl group.
- Examples of the definition and specific examples of the boric acid ester residue and the substituted stannyl group include the same definitions and examples as those described for Q 100 or Q 300 above.
- Examples of the substituted silyl group include a group represented by —SiR 500 3 .
- R 500 represents a monovalent organic group.
- Examples of the monovalent organic group include an alkyl group, a cycloalkyl group, and an aryl group.
- the carbon number of the alkyl group is usually 1 to 30, and specific examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl grave, n-pentyl group, isopentyl group, 2-methylbutyl group, 1-methylbutyl group, n-hexyl group, isohexyl group, 3-methylpentyl group, 21-methylpentyl group, 1-methylpentyl group, heptyl group, octyl group, Examples include isooctyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group, dodecyl group, tetradecyl group, hexadecyl tomb, octadecyl group, and eicosyl group.
- the cycloalkyl group usually has 3 to 30 carbon atoms, and specific examples thereof include a cyclopentyl group, a cyclohexyl group, and an adamantyl group.
- Examples of the aryl group include a phenyl group and a naphthyl group.
- the substituted silyl group is preferably -SiMe 3 , -SiEt 3 , -SiBu 3 , -SiPh 3 , more preferably -SiMe 3 , -SiEt 3 , or -SiBu 3 .
- Me represents a methyl group
- Et represents an ethyl group
- Bu represents a butyl group
- Ph represents a phenyl group.
- the halogen atom represented by Q includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- Q is preferably a bromine atom, a dihydroxyboryl group, a boric acid ester residue, a substituted stannyl group, or a substituted silyl group, more preferably a bromine atom, a dihydroxyboryl group, or a boric acid ester residue, and more preferably a bromine atom. It is.
- Examples of the compound represented by Formula (4) include compounds represented by Formula 501 to Formula 652.
- R, R 1 , R 2 and R 3 represent the same meaning as described above.
- Formula 501 to Formula 510, Formula 531 to Formula 550, Formula 571 to Formula 590, Formula 611 to 620, 621, 624, 625, 628, 629, 632, 633 to 642, and 643 to 652 are preferable. More preferred are compounds represented by the formulas 501 to 510, 541 to 550, 581 to 590, 621, 625, 629, 633 to 637, and 643 to 647.
- a known method can be used for bromination, and examples thereof include a method of brominating without a solvent or using a brominating agent in a solvent.
- the solvent used in the reaction includes saturated hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane, unsaturated hydrocarbons such as benzene, toluene, ethylbenzene, xylene, carbon tetrachloride, chloroform, dichloromethane, Examples thereof include halogenated saturated hydrocarbons such as chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane and bromocyclohexane, and halogenated unsaturated hydrocarbons such as chlorobenzene, dichlorobenzene and trichlorobenzene.
- brominating agent examples include bromine, N-bromosuccinimide (hereinafter sometimes referred to as NBS), carbon tetrachloride, hydrobromic acid and the like. It is also possible to use a combination of a plurality of these brominating agents.
- the amount of brominating agent used is usually 2 to 100,000 equivalents relative to the number of moles of the compound represented by formula (4-2).
- Catalysts include metals such as iron, cobalt, nickel, copper, iron halides, cobalt halides, halogenated metals such as nickel halides, copper halides, radical generators such as benzoyl peroxide, azoisobutyronitrile, etc. Can be mentioned.
- the catalyst is preferably a metal or a metal halide, more preferably iron or iron bromide.
- the amount of the catalyst used is usually 0.001 to 10 equivalents, preferably 0.01 to 1 equivalent, relative to the number of moles of the compound represented by the formula (4-2).
- the reaction temperature is usually ⁇ 50 to 200 ° C., preferably 0 to 150 ° C.
- the product After the reaction, for example, after adding water to stop the reaction, the product is extracted with an organic solvent and subjected to usual post-treatment such as distilling off the solvent, and the compound represented by the formula (4-1) is obtained. Obtainable.
- the product can be isolated and purified by a method such as chromatographic fractionation or recrystallization.
- a commercially available compound can be used.
- a compound in which Y 1 is a sulfur atom can be obtained by the production method described in Patent Literature (International Patent Publication WO2011-136311A1). It can be produced and used by reacting the compound represented by formula (4-3) with thionyl chloride.
- the compound of the present invention can exhibit high electron and / or hole transport properties, when an organic thin film containing the compound is used in a device, it is generated by electrons or holes injected from an electrode or light absorption. Charge can be transported. Taking advantage of these characteristics, it can be suitably used for various elements such as a photoelectric conversion element, an organic thin film transistor, an organic electroluminescence element, and a sensor. Hereinafter, these elements will be described individually.
- the compound of the present invention preferably has a long light absorption wavelength.
- the light absorption terminal wavelength can be determined by the following method.
- a spectrophotometer for example, JASCO-V670, made by JASCO Corporation
- JASCO-V670 since the measurable wavelength range is 200 to 1500 nm, the measurement is performed in the wavelength range.
- the absorption spectrum of the substrate used for measurement is measured.
- a quartz substrate, a glass substrate, or the like is used.
- a thin film containing a compound is formed on the substrate from a solution containing the compound or a melt containing the compound.
- the absorbance of the absorption peak with the longest wavelength among the absorption peaks is defined as 100%, and the intersection of the absorption peak and a straight line parallel to the horizontal axis (wavelength axis) including the absorbance of 50% of the absorption peak.
- the intersection point that is longer than the peak wavelength is taken as the first point.
- the intersection point between the absorption peak and a straight line parallel to the wavelength axis containing 25% of the absorbance, which is longer than the peak wavelength of the absorption peak, is defined as a second point.
- the intersection of the straight line connecting the first point and the second point and the reference line is defined as the light absorption terminal wavelength.
- the reference line is the intersection of the absorption peak and the straight line parallel to the wavelength axis including the absorbance of 10% at the absorption peak of the longest wavelength, where the absorbance of the absorption peak is 100%.
- the third point on the absorption spectrum that is 100 nm longer than the reference wavelength and the absorption spectrum that is 150 nm longer than the reference wavelength with reference to the wavelength of the intersection that is longer than the peak wavelength of the absorption peak A straight line connecting the top and the fourth point.
- the photoelectric conversion element having the compound of the present invention has one or more active layers containing the compound of the present invention between the first electrode and the second electrode.
- the compound of the present invention is preferably used as a p-type organic semiconductor. The operation mechanism of the photoelectric conversion element of this embodiment will be described.
- an electron-accepting compound such as a fullerene derivative and / or an electron-donating compound (p-type organic semiconductor) such as the compound of the present invention.
- an electron-accepting compound such as a fullerene derivative and / or an electron-donating compound (p-type organic semiconductor) such as the compound of the present invention.
- n-type organic semiconductor such as a fullerene derivative and / or an electron-donating compound (p-type organic semiconductor) such as the compound of the present invention.
- p-type organic semiconductor such as the compound of the present invention.
- the photoelectric conversion element produced using the compound of the present invention is usually formed on a substrate.
- the substrate may be any substrate that does not chemically change when the electrodes are formed and the organic layer is formed.
- Examples of the material for the substrate include glass, plastic, polymer film, and silicon.
- the opposite electrode that is, the electrode far from the substrate
- a first active layer containing the compound of the present invention is interposed between a pair of electrodes, at least one of which is transparent or translucent, and the first active layer. Adjacent to the photoelectric conversion element is a second active layer containing an electron-accepting compound such as a fullerene derivative.
- the photoelectric conversion element of the present invention preferably has an active layer containing the compound.
- the transparent or translucent electrode material examples include a conductive metal oxide film and a translucent metal thin film. Specifically, a film formed using a conductive material made of indium oxide, zinc oxide, tin oxide, and indium tin oxide (ITO), indium zinc oxide, etc., which is a composite thereof, NESA Alternatively, gold, platinum, silver, copper, or the like is used, and ITO, indium / zinc / oxide, and tin oxide are preferable.
- the method for producing the electrode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and the like.
- an organic transparent conductive film such as polyaniline and derivatives thereof, polythiophene and derivatives thereof may be used.
- One electrode may not be transparent, and as the electrode material of the electrode, a metal, a conductive polymer, or the like can be used.
- the electrode material include metals such as lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, etc.
- one or more alloys selected from the group consisting of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, and tin.
- Examples include alloys with metals, graphite, graphite intercalation compounds, polyaniline and derivatives thereof, and polythiophene and derivatives thereof.
- Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy.
- An additional intermediate layer other than the active layer may be used as a means for improving the photoelectric conversion efficiency.
- the material used for the intermediate layer include alkali metals such as lithium fluoride, halides of alkaline earth metals, oxides such as titanium oxide, and PEDOT (poly-3,4-ethylenedioxythiophene).
- the active layer may contain the compound of the present invention alone or in combination of two or more.
- a compound other than the compound of the present invention can be mixed and used as the electron donating compound and / or the electron accepting compound in the active layer.
- the electron-donating compound and the electron-accepting compound are relatively determined from the energy levels of these compounds.
- Examples of the electron donating compound include, in addition to the compound of the present invention, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, oligothiophene and derivatives thereof, polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, side Examples thereof include polysiloxane derivatives having an aromatic amine residue in the chain or main chain, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, polyphenylene vinylene and derivatives thereof, polythienylene vinylene and derivatives thereof.
- Examples of the electron-accepting compound include, in addition to the compound of the present invention, carbon materials, metal oxides such as titanium oxide, oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof.
- Anthraquinone and derivatives thereof tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof , Polyfluorenes and derivatives thereof, phenanthroline derivatives such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (basocuproin), fullerenes and fullerene derivatives.
- phenanthroline derivatives such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (basocuproin), fullerenes and fullerene derivatives.
- Ku is titanium oxide, carbon nanotubes, fullerene, a fullerene derivative, particularly preferably a fullerene, a fullerene derivative.
- fullerene and fullerene derivatives include C 60 , C 70 , C 76 , C 78 , C 84 and derivatives thereof.
- the fullerene derivative represents a compound in which at least a part of fullerene is modified.
- Examples of the fullerene derivative include a compound represented by the formula (I), a compound represented by the formula (II), a compound represented by the formula (III), and a compound represented by the formula (IV).
- R a is an alkyl group, aryl group, heteroaryl group or group having an ester structure. A plurality of R a may be the same or different.
- R b represents an alkyl group or an aryl group, and a plurality of R b may be the same or different.
- alkyl group and aryl group represented by R a and R b are the same as the definitions and specific examples of the alkyl group and aryl group represented by R 1 .
- heteroaryl group represented by Ra examples include a thiophenediyl group, a pyridinediyl group, a furandiyl group, and a pyrrolediyl group.
- Examples of the group having an ester structure represented by Ra include a group represented by the formula (V). (In the formula, u1 represents an integer of 1 to 6, u2 represents an integer of 0 to 6, and R c represents an alkyl group, an aryl group, or a heteroaryl group.)
- alkyl group, aryl group and heteroaryl group represented by R c are the same as the definitions and specific examples of the alkyl group, aryl group and heteroaryl group represented by R a .
- C 60 derivative examples include the following.
- C 70 derivative examples include the following.
- fullerene derivatives include [6,6] phenyl-C61 butyric acid methyl ester (C60PCBM, [6,6] -phenyl C61 butyric acid methyl ester), [6,6] phenyl-C71 butyric acid methyl ester (C70PCBM, [ 6,6] -Phenyl C71 butyric acid methyl ester), [6,6] Phenyl-C85 butyric acid methyl ester (C84PCBM, [6,6] -Phenyl C85 butyric acid methyl ester), [6,6] Chenyl-C61 butyric acid And methyl ester ([6,6] -Thienyl C61 butyric acid methyl ester).
- the ratio of the fullerene derivative is preferably 10 to 1000 parts by weight, preferably 20 to 500 parts by weight with respect to 100 parts by weight of the compound of the present invention. More preferably.
- the thickness of the active layer is usually preferably 1 nm to 100 ⁇ m, more preferably 2 nm to 1000 nm, still more preferably 5 nm to 500 nm, and more preferably 20 nm to 200 nm.
- the method for producing the active layer may be produced by any method, and examples thereof include a film formation from a solution containing a compound and a solvent, and a film formation method by a vacuum deposition method.
- a preferred method for producing a photoelectric conversion element is a method for producing an element having a first electrode and a second electrode, and having an active layer between the first electrode and the second electrode, An element having a step of forming an active layer by applying a solution (ink) containing the compound of the present invention and a solvent on the first electrode by a coating method, and a step of forming a second electrode on the active layer It is a manufacturing method.
- the solvent used for film formation from a solution may be any solvent that dissolves the compound of the present invention.
- the solvent include unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexyl, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene, carbon tetrachloride, chloroform, and dichloromethane.
- Halogenated saturated hydrocarbon solvents such as dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane and bromocyclohexane, and halogenated unsaturated hydrocarbons such as chlorobenzene, dichlorobenzene and trichlorobenzene
- the solvent include ether solvents such as tetrahydrofuran and tetrahydropyran.
- the compound of the present invention can usually be dissolved in the solvent in an amount of 0.1% by weight or more.
- slit coating method When forming a film using a solution, slit coating method, knife coating method, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, Application methods such as spray coating, screen printing, gravure printing, flexographic printing, offset printing, inkjet coating, dispenser printing, nozzle coating, capillary coating, slit coating, capillary A coating method, a gravure coating method, a micro gravure coating method, a bar coating method, a knife coating method, a nozzle coating method, an ink jet coating method, and a spin coating method are preferable. From the viewpoint of film formability, the surface tension of the solvent at 25 ° C.
- the value is preferably larger than 15 mN / m, more preferably larger than 15 mN / m and smaller than 100 mN / m, larger than 25 mN / m and larger than 60 mN / m. It is more preferable that the value is small.
- Organic thin film transistor The compound of the present invention can also be used for organic thin film transistors.
- the organic thin film transistor has a configuration including a source electrode and a drain electrode, an organic semiconductor layer (active layer) serving as a current path between these electrodes, and a gate electrode for controlling the amount of current passing through the current path.
- the organic semiconductor layer is constituted by the organic thin film described above. Examples of such an organic thin film transistor include a field effect type and an electrostatic induction type.
- a field effect organic thin film transistor includes a source electrode and a drain electrode, an organic semiconductor layer (active layer) serving as a current path between them, a gate electrode for controlling the amount of current passing through the current path, and an organic semiconductor layer and a gate electrode It is preferable to provide an insulating layer disposed between the two.
- the source electrode and the drain electrode are preferably provided in contact with the organic semiconductor layer (active layer), and the gate electrode is preferably provided with an insulating layer in contact with the organic semiconductor layer interposed therebetween.
- the organic semiconductor layer is constituted by an organic thin film containing the compound of the present invention.
- the static induction organic thin film transistor has a source electrode and a drain electrode, an organic semiconductor layer (active layer) serving as a current path between them, and a gate electrode that controls the amount of current passing through the current path. It is preferable to be provided in the organic semiconductor layer.
- the source electrode, the drain electrode, and the gate electrode provided in the organic semiconductor layer are preferably provided in contact with the organic semiconductor layer.
- the structure of the gate electrode may be a structure in which a current path flowing from the source electrode to the drain electrode is formed and the amount of current flowing through the current path can be controlled by a voltage applied to the gate electrode. An electrode is mentioned.
- the organic semiconductor layer is constituted by an organic thin film containing the compound of the present invention.
- the photoelectric conversion element using the compound of the present invention can be operated as an organic thin film solar cell by generating photovoltaic power between the electrodes by irradiating light such as sunlight from a transparent or translucent electrode. . It can also be used as an organic thin film solar cell module by integrating a plurality of organic thin film solar cells.
- the organic light sensor By irradiating light from a transparent or translucent electrode in a state where a voltage is applied between the electrodes or in a state where no voltage is applied, a photocurrent flows and the organic light sensor can be operated. It can also be used as an organic image sensor by integrating a plurality of organic photosensors.
- the above-mentioned organic thin film transistor can be used as a pixel driving element used for controlling the pixel of an electrophoretic display, a liquid crystal display, an organic electroluminescence display, etc., and controlling the uniformity of screen luminance and the screen rewriting speed. .
- the organic thin film solar cell can basically have the same module structure as a conventional solar cell module.
- the solar cell module generally has a structure in which cells are formed on a support substrate such as metal or ceramic, and the cell is covered with a filling resin or protective glass, and light is taken in from the opposite side of the support substrate. It is also possible to use a transparent material such as tempered glass for the support substrate, configure a cell thereon, and take in light from the transparent support substrate side.
- a module structure called a super straight type, a substrate type, and a potting type, a substrate integrated module structure used in an amorphous silicon solar cell, and the like are known.
- the organic thin-film solar cell produced using the compound of the present invention can also be appropriately selected from these module structures depending on the purpose of use, the place of use and the environment.
- a typical super straight type or substrate type module cells are arranged at regular intervals between support substrates that are transparent on one or both sides and subjected to antireflection treatment, and adjacent cells are connected by metal leads or flexible wiring.
- the current collector electrode is connected to the outer edge portion, and the generated power is taken out to the outside.
- plastic materials such as ethylene vinyl acetate (EVA) may be used between the substrate and the cell in the form of a film or a filling resin depending on the purpose in order to protect the cell and improve the current collection efficiency.
- EVA ethylene vinyl acetate
- the surface protective layer is made of a transparent plastic film, or a protective function is provided by curing the above filling resin. It is possible to eliminate the support substrate on one side.
- the periphery of the support substrate is fixed in a sandwich shape with a metal frame in order to ensure internal sealing and module rigidity, and the support substrate and the frame are hermetically sealed with a sealing material. If a flexible material is used for the cell itself, the support substrate, the filling material, and the sealing material, a solar cell can be formed on the curved surface.
- a solar cell using a flexible support such as a polymer film
- cells are sequentially formed while feeding out a roll-shaped support, cut to a desired size, and then the periphery is sealed with a flexible and moisture-proof material.
- the battery body can be produced. It may be a module structure called “SCAF” described in Solar Energy Materials and Solar Cells, 48, p383-391.
- SCAF solar Energy Materials and Solar Cells, 48, p383-391.
- a solar cell using a flexible support can be used by being bonded and fixed to a curved glass or the like.
- the compound of this invention can also be used for an organic electroluminescent element (organic EL element).
- the organic EL element has a light emitting layer between the first electrode and the second electrode.
- the organic EL element may include a hole transport layer and an electron transport layer in addition to the light emitting layer.
- the compound of the present invention is contained in any one of the light emitting layer, the hole transport layer, and the electron transport layer.
- the light emitting layer may contain a charge transport material (which means a generic term for an electron transport material and a hole transport material).
- an organic EL element an element having an anode, a light emitting layer, and a cathode, and an anode, a light emitting layer, and an electron having an electron transport layer containing an electron transport material adjacent to the light emitting layer between the cathode and the light emitting layer.
- At least one of the first electrode and the second electrode is preferably transparent or translucent.
- the compounds of the present invention can be used in the manufacture of organic field effect transistor (OFET) sensors.
- the OFET sensor of the present invention uses an organic field effect transistor as a signal conversion element when an input signal is output as an electric signal, and has sensitivity or selectivity in any of a metal-insulator-semiconductor structure. It has been granted.
- Examples of the OFET sensor of the present invention include a biosensor, a gas sensor, an ion sensor, and a humidity sensor.
- the biosensor of the present invention includes a substrate and an organic transistor provided on the substrate, and the organic transistor includes an organic semiconductor layer containing the compound of the present invention and a source region provided in contact with the organic semiconductor. And a drain region, a channel region provided in the organic semiconductor layer and serving as a channel between the source region and the drain region, a gate electrode capable of applying an electric field to the channel region, and the channel region; A gate insulating film provided between the gate electrode and a sensitive region as a probe that specifically interacts with a target substance in the channel region and / or the gate insulating film.
- the biosensor of the present invention functions as a biosensor element by causing a characteristic change when the target substance concentration changes in the sensitive region.
- a method for detecting a target substance in a test sample a method using a biosensor in which a biomolecule such as nucleic acid or protein or an artificially synthesized functional group is immobilized on the surface of a solid phase carrier as a probe is widely used.
- the target substance is captured on the surface of the solid support using the specific affinity of biomolecules such as complementary nucleic acid chain interaction, antigen-antibody reaction, enzyme-substrate reaction, and receptor-ligand interaction. Therefore, a substance having specific affinity for the target substance is selected as a probe.
- the probe is fixed on the surface of the solid support by a method suitable for the type of probe or solid support.
- the probe can be synthesized on the surface of the solid phase carrier (for example, nucleic acid extension reaction, etc.).
- the surface of the solid phase carrier to which the probe is immobilized is brought into contact with the test sample and cultured under appropriate conditions. By doing so, a probe-target substance complex is formed on the surface of the solid phase carrier.
- the channel region and / or the gate insulating film itself may function as a probe.
- the gas sensor of the present invention includes a substrate and an organic transistor provided on the substrate, and the organic transistor includes an organic semiconductor layer containing the compound of the present invention, a source region provided in contact with the organic semiconductor, and A drain region; a channel region provided in the organic semiconductor layer and serving as a channel between the source region and the drain region; a gate electrode capable of applying an electric field to the channel region; the channel region; And the channel region and / or the gate insulating film is a gas sensitive part.
- the gas sensor of the present invention functions as a gas sensor element by causing a change in characteristics such as conductivity and dielectric constant when gas is adsorbed and desorbed from the channel region and / or the gate insulating film.
- the gases to be detected include halogens such as F2 and Cl2 as electron accepting gases, organic acids such as nitrogen oxides, sulfur oxides and acetic acid, amines such as ammonia and aniline as electron donating gases, carbon monoxide and hydrogen. It is also possible to detect.
- the compound of the present invention can also be used for the production of a pressure sensor.
- the pressure sensor of the present invention includes a substrate and an organic transistor provided on the substrate, and the organic transistor includes an organic semiconductor layer containing the compound of the present invention and a source region provided in contact with the organic semiconductor. And a drain region, a channel region provided in the organic semiconductor layer and serving as a channel between the source region and the drain region, a gate electrode capable of applying an electric field to the channel region, and the channel region; A gate insulating film provided between the gate electrode and the channel region and / or the gate insulating film is a pressure-sensitive portion.
- the pressure sensor of the present invention functions as a pressure sensitive element by causing a characteristic change when pressure is sensed by the pressure sensitive part.
- the organic material is generally more flexible and stretchable than the inorganic material, and therefore the organic material is preferable as the pressure sensitive part of the pressure sensor.
- an alignment layer may be included in order to increase the crystallinity of the organic semiconductor. Examples of the alignment layer include a monomolecular film formed with a silane coupling agent such as hexamethyldisilazane on the gate insulating film.
- the compound of the present invention can also be used for a conductivity modulation type sensor.
- the conductivity modulation type sensor of the present invention uses a conductivity measuring element as a signal conversion element when outputting an input signal as an electric signal, and an organic semiconductor layer using the compound of the present invention or Sensitivity or selectivity for the sensor target input is given to any of the coating films coated on at least a part of the organic semiconductor layer using the compound, and the sensor target input is transmitted to the polymer compound. It is detected as a change in degree.
- the sensor include a biosensor, a gas sensor, an ion sensor, and a humidity sensor.
- the compound of the present invention is an amplification circuit including an organic field effect transistor (OFET) for amplifying output signals from various sensors such as a biosensor, a gas sensor, an ion sensor, a humidity sensor, and a pressure sensor formed separately. It can also be used for manufacturing.
- OFET organic field effect transistor
- the compound of the present invention can be used as a sensor array including a plurality of various sensors such as a biosensor, a gas sensor, an ion sensor, a humidity sensor, and a pressure sensor.
- the compound of the present invention includes a plurality of various sensors such as a biosensor, a gas sensor, an ion sensor, a humidity sensor, and a pressure sensor formed separately, and an organic field effect transistor (amplifying an output signal from each sensor individually) OFET) as an amplifier circuit can be used to manufacture a sensor array with an amplifier circuit.
- various sensors such as a biosensor, a gas sensor, an ion sensor, a humidity sensor, and a pressure sensor formed separately, and an organic field effect transistor (amplifying an output signal from each sensor individually) OFET) as an amplifier circuit can be used to manufacture a sensor array with an amplifier circuit.
- the flask was cooled to ⁇ 78 ° C., and the above solution A was added dropwise over 5 minutes. After the dropwise addition, the mixture was stirred at -78 ° C for 5 minutes, and then 3.63 mL (33.4 mmol) of trimethylsilyl chloride was added dropwise over 5 minutes. After dropping, the flask was warmed to room temperature over 10 minutes and then stirred at room temperature for 2 hours. Thereafter, water was added to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was distilled off with an evaporator. The obtained solid was dissolved in hexane and passed through silica gel column chromatography. The solvent of the filtrate was distilled off with an evaporator to obtain 3.33 g (11.1 mmol) of the target compound 2. The yield was 86.5%.
- Example 1 In a 200 mL flask in which the gas in the flask was replaced with argon, 203.6 mg (0.193 mmol) of Compound 4 synthesized by the method described in International Publication No. 2011/052709 was described in International Publication No. 2011/052709. 214.5 mg (0.193 mmol) of the compound 5 synthesized by the above method, 61.3 mg (0.186 mmol) of the compound 6 synthesized by the method described in International Publication No.
- polymer compound A this polymer is referred to as polymer compound A.
- Example 2 (Production and evaluation of ink and organic thin film solar cell) A glass substrate on which an ITO film having a thickness of 150 nm was applied by a sputtering method was subjected to surface treatment using an ozone UV apparatus. Next, polymer compound A and phenyl C61-butyric acid methyl ester (fullerene C60PCBM) (manufactured by Frontier Carbon) were dissolved in orthodichlorobenzene so that the weight ratio of fullerene C60PCBM to polymer compound A was 2, and the ink 1 was produced. In ink 1, the total weight of polymer compound A and fullerene C60PCBM was 2.0% by weight with respect to the weight of ink 1.
- fullerene C60PCBM phenyl C61-butyric acid methyl ester
- the ink 1 was applied onto an indium tin oxide (ITO) film on a glass substrate by spin coating to prepare an organic film containing the polymer compound A.
- the thickness of the organic film was about 100 nm. It was 890 nm when the light absorption terminal wavelength of the organic film was measured.
- calcium was vapor-deposited with a thickness of 42 nm on the organic film by a vacuum vapor deposition machine, and then aluminum was vapor-deposited with a thickness of 100 nm to produce an organic thin film solar cell.
- the shape of the obtained organic thin film solar cell was a square of 2 mm ⁇ 2 mm.
- the obtained organic thin film solar cell is irradiated with constant light using a solar simulator (trade name: OTENTO-SUNII: AM1.5G filter, irradiance: 100 mW / cm 2 , manufactured by Spectrometer Co., Ltd.), and the generated current and voltage are measured.
- the photoelectric conversion efficiency, short-circuit current density, open-circuit voltage, and fill factor were determined. Jsc (short-circuit current density) is 13.9 mA / cm 2 , Voc (open-circuit voltage) is 0.793 V, FF (fill factor) is 0.639, and photoelectric conversion efficiency ( ⁇ ) Was 7.02%.
- Comparative Example 1 Synthesis of polymer compound B 3200 mg (3.039 mmol) of the compound 4 synthesized by the method described in International Publication No. 2011/052709, and the method described in International Publication No. 2011/052709, in a 1000 mL flask in which the gas in the flask was replaced with argon 3371 mg (3.039 mmol) of the compound 5 synthesized in the above, 2100 mg (6.365 mmol) of the compound 6 synthesized by the method described in International Publication No.
- Comparative Example 2 Provide and evaluation of ink and organic thin film solar cell
- An organic thin film solar cell was prepared in the same manner as in Example 2 except that the polymer compound B was used in place of the polymer compound A.
- Photoelectric conversion efficiency, short-circuit current density, open-circuit voltage, The fill factor was determined. Jsc (short circuit current density) is 15.0 mA / cm 2 , Voc (open circuit voltage) is 0.712 V, FF (fill factor) is 0.637, and photoelectric conversion efficiency ( ⁇ ) was 6.81%.
- the resulting toluene solution was bubbled with argon for 30 minutes. Thereafter, 4.38 mg (0.0048 mmol) of tris (dibenzylideneacetone) dipalladium was added to the toluene solution, and the mixture was stirred at 100 ° C. for 8 hours. Thereafter, 209 mg of phenyl bromide was added to the reaction solution and reacted at 100 ° C. for 1 hour. Thereafter, the flask was cooled to 25 ° C., and the reaction solution was poured into 100 mL of methanol.
- polymer compound C The precipitated polymer was collected by filtration, and the obtained polymer was dissolved in 21 mL of o-dichlorobenzene and passed through an alumina / silica gel column. The obtained solution was poured into methanol to precipitate a polymer, and the polymer was filtered and then dried to obtain 130 mg of a purified polymer.
- this polymer is referred to as polymer compound C.
- Comparative Example 4 Provide and evaluation of ink and organic thin film solar cell
- An organic thin film solar cell was prepared in the same manner as in Example 2 except that the polymer compound C was used in place of the polymer compound A.
- Photoelectric conversion efficiency, short-circuit current density, open-circuit voltage, The fill factor was determined. Jsc (short circuit current density) is 0.21 mA / cm 2 , Voc (open end voltage) is 0.891 V, FF (fill factor) is 0.421, and photoelectric conversion efficiency ( ⁇ ) was 0.787%.
- Example 3 In a 200 mL flask in which the gas in the flask was replaced with argon, 293.8 mg (279.0 mmol) of compound 4, 309.5 mg (279.0 mmol) of compound 5, 125.0 mg (378.9 mmol) of compound 6, and compound 3 in 50.9 mg (162.4 mmol), tris (2-toluyl) phosphine 12.2 mg (0.040 mmol), and toluene 32 ml were added to obtain a uniform solution. The resulting toluene solution was bubbled with argon for 30 minutes.
- Example 4 Provide and evaluation of ink and organic thin film solar cell
- An organic thin film solar cell was prepared in the same manner as in Example 2 except that the polymer compound D was used in place of the polymer compound A.
- Photoelectric conversion efficiency, short-circuit current density, open-circuit voltage, The fill factor was determined. Jsc (short circuit current density) is 15.4 mA / cm 2 , Voc (open circuit voltage) is 0.738 V, FF (fill factor) is 0.627, and photoelectric conversion efficiency ( ⁇ ) was 7.12%.
- Example 5 In a 200 mL flask in which the gas in the flask was replaced with argon, 284.5 mg (270.2 mmol) of compound 4, 128.4 mg (115.8 mmol) of compound 5, 61.3 mg (0.186 mmol) of compound 6, and compound 3 in 58.3 mg (0.186 mmol), tris (2-toluyl) phosphine 10.2 mg (0.033 mmol), and toluene 25 ml were added to obtain a uniform solution. The resulting toluene solution was bubbled with argon for 30 minutes.
- Example 6 Provide and evaluation of ink and organic thin film solar cell
- An organic thin film solar cell was prepared in the same manner as in Example 2 except that the polymer compound E was used instead of the polymer compound A, and the photoelectric conversion efficiency, short-circuit current density, open-circuit voltage, The fill factor was determined.
- Jsc short-circuit current density
- Voc open-circuit voltage
- FF fill factor (curve factor))
- photoelectric conversion efficiency ( ⁇ ) was 7.10%.
- An organic thin film solar cell having an organic layer containing the compound of the present invention is useful because of its high photoelectric conversion efficiency.
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Abstract
Description
[1]式(1)で表される構造単位と式(2)で表される構造単位とを有する化合物。
〔式中、X1、X2、X3及びX4は、同一又は相異なり、窒素原子又は
=CH−を表す。Y1及びY2は、同一又は相異なり、硫黄原子、酸素原子、セレン原子、−N(R1)−又は−CR2=CR3−を表す。R1、R2及びR3は、同一又は相異なり、水素原子、ハロゲン原子、アミノ基、シアノ基又は1価の有機基を表す。W1及びW3は、同一又は相異なり、ハロゲン原子、シアノ基、又は1価の有機基を表す。W2及びW4は、同一又は相異なり、水素原子、ハロゲン原子、シアノ基又は1価の有機基を表す。ただし、式(1)で表される構造単位と式(2)で表される構造単位とは同一ではない。〕
[2]Y1とY2が同一ではない[1]記載の化合物。
[3] W1、W2、W3及びW4がいずれもハロゲン原子である[1]または[2]記載の化合物。
[4]さらに、式(3)で表される構造単位を有する[1]~[3]のいずれかに記載の化合物。
〔式中、Ar1は、アリーレン基又はヘテロアリーレン基を表す。〕
[5]Ar1が、ヘテロアリーレン基である[4]に記載の化合物。
[6]ヘテロアリーレン基がチオフェン環を含む基である[4]または[5]に記載の化合物。
[7] 高分子化合物である[1]~[6]のいずれか一項に記載の化合物。
[8]ポリスチレン換算の重量平均分子量が3×103以上である[7]に記載の高分子化合物。
[9] 第1の電極と第2の電極とを有し、該第1の電極と該第2の電極との間に活性層を有し、該活性層に[1]~[6]のいずれかに記載の化合物、または[7]もしくは[8]に記載の高分子化合物を含有する有機光電変換素子。
[10]ゲート電極と、ソース電極と、ドレイン電極と、活性層とを有し、該活性層に[1]~[6]のいずれかに記載の化合物、または[7]もしくは[8]に記載の高分子化合物を含有する有機薄膜トランジスタ。
[11][1]~[6]のいずれかに記載の化合物、または[7]もしくは[8]に記載の高分子化合物を含有するセンサー。
式中、X1、X2、X3及びX4は、同一又は相異なり、窒素原子又は
=CH−を表す。X1、X2、X3及びX4として好ましくは窒素原子である。
Y1は、硫黄原子、酸素原子、セレン原子、−N(R1)−又は
−CR2=CR3−のいずれかを表す。Y1として好ましくは硫黄原子、酸素原子、または−N(R1)−であり、より好ましくは硫黄原子または酸素原子であり、さらに好ましくは酸素原子である。
Y2は、硫黄原子、酸素原子、セレン原子、−N(R1)−又は−CR2=CR3−のいずれかを表す。Y2として好ましくは硫黄原子、酸素原子、または
−N(R1)−であり、より好ましくは硫黄原子または酸素原子であり、さらに好ましくは硫黄原子である。
Y1とY2は同一であってもよいが、相異なるほうが光電変換効率を高める観点で好ましい。
Y1とY2が相異なる場合、Y1及びY2の一方が硫黄原子であり、他方が酸素原子であることが好ましい。
1価の有機基としては、置換されていてもよいアルキル基、置換されていてもよいシクロアルキル基、置換されていてもよいアルコキシ基、置換されていてもよいシクロアルコキシ基、置換されていてもよいアルキルチオ基、置換されていてもよいシクロアルキルチオ基、置換されていてもよいアリール基、置換されていてもよいアリールオキシ基、置換されていてもよいアリールチオ基、置換されていてもよいアリールアルキル基、置換されていてもよいアリールアルコキシ基、置換されていても良いアリールアルキルチオ基、アシル基、アシルオキシ基、アミド基、イミド基、置換アミノ基、置換シリル基、置換シリルオキシ基、置換シリルチオ基、置換シリルアミノ基、1価の複素環基、複素環オキシ基、複素環チオ基、アリールアルケニル基、アリールアルキニル基又はカルボキシル基を表す。
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子が挙げられる。
1価の複素環基は、複素環化合物から水素原子1個を除いた基である。
複素環化合物としては、フラン、チオフェン、ピロール、ピロリン、ピロリジン、オキサゾール、イソオキサゾール、チアゾール、イソチアゾール、イミダゾール、イミダゾリン、イミダゾリジン、ピラゾール、ピラゾリン、プラゾリジン、フラザン、トリアゾール、チアジアゾール、オキサジアゾール、テトラゾール、ピラン、ピリジン、ピペリジン、チオピラン、ピリダジン、ピリミジン、ピラジン、ピペラジン、モルホリン、トリアジン、ベンゾフラン、イソベンゾフラン、ベンゾチオフェン、インドール、イソインドール、インドリジン、インドリン、イソインドリン、クロメン、クロマン、イソクロマン、ベンゾピラン、キノリン、イソキノリン、キノリジン、ベンゾイミダゾール、ベンゾチアゾール、インダゾール、ナフチリジン、キノキサリン、キナゾリン、キナゾリジン、シンノリン、フタラジン、プリン、プテリジン、カルバゾール、キサンテン、フェナントリジン、アクリジン、β−カルボリン、ペリミジン、フェナントロリン、チアントレン、フェノキサチイン、フェノキサジン、フェノチアジン、フェナジンが挙げられる。1価の複素環基の炭素数は通常1~20である。1価の複素環基としては、ヘテロアリール基が好ましい。
〔式(D)及び式(E)中、Ar7はそれぞれ1価の複素環基を表す。〕
複素環オキシ基は、その炭素数が通常4~60である。複素環オキシ基の具体例としては、チエニルオキシ基、C1~C12アルキルチエニルオキシ基、ピロリルオキシ基、フリルオキシ基、ピリジルオキシ基、C1~C12アルキルピリジルオキシ基、イミダゾリルオキシ基、ピラゾリルオキシ基、トリアゾリルオキシ基、オキサゾリルオキシ基、チアゾールオキシ基及びチアジアゾールオキシ基が挙げられる。
R1、R2及びR3として好ましくはアルキル基、アリール基又はアリールアルキル基である。
ここで、アリーレン基とは、置換されていてもよい芳香族炭化水素から、水素原子2個を除いた原子団である。アリーレン基に含まれる芳香環を構成する炭素数は通常6~60程度であり、好ましくは6~20である。芳香族炭化水素としては、ベンゼン環をもつもの、縮合環をもつもの、独立したベンゼン環又は縮合環2個以上が直接結合したもの又はビニレン等の基を介して結合したものも含まれる。
〔式中、d環は、置換されていてもよい芳香族炭素環又は置換されていてもよい芳香族複素環を表す。mは、1以上の整数を表す。Zは、式(z−1)~式(z−8)で表される基である。d環が複数個ある場合、それらは同一であっても相異なってもよい。Zが複数個ある場合、それらは同一であっても相異なってもよい。
(式(z−1)~式(z−8)中、Rは、水素原子、ハロゲン原子、アミノ基、シアノ基又は1価の有機基を表す。Rが2個ある場合、それらは同一でも相異なってもよい。2個あるRは互いに連結し、それらが結合した炭素原子とともに環状構造を形成していてもよい。)〕
芳香族複素環としては、フラン環、チオフェン環、ピロール環、シロール環、ボロール環、ホスホール環、イミダゾール環、トリアゾール環、チアゾール環、オキサゾール環、イソオキサゾール環、ピラゾール環、イソチアゾール環、ピリジン環、ピラジン環、ピリミジン環、キノリン環、イソキノリン環、インドール環、ベンゾフラン環、イソベンゾフラン環、ベンゾイミダゾール環、ベンゾチオフェン環、ベンゾチアゾール環、ベンゾオキサゾール環などが挙げられる。
〔式中、e環は、置換されていてもよい単環の芳香族炭素環又は置換されていてもよい単環の芳香族複素環を表す。nは、1以上の整数を表す。pは、0~5の整数を表す。e環が複数個ある場合、それらは、同一であっても相異なってもよい。〕
pは、0~5の整数を表す。好ましくは0~4であり、より好ましくは0~3であり、さらに好ましくは0~2である。
P=(式(1)で表される構造単位の数)/{(式(1)で表される構造単位の数))+(式(2)で表される構造単位の数)}
本発明における高分子化合物とは、ゲルパーミエーションクロマトグラフィー(以下GPCと呼称することもある)で測定したポリスチレン換算の数平均分子量が1000以上の化合物を指す。本発明の高分子化合物のポリスチレン換算の数平均分子量は、好ましくは2000~1000000であり、より好ましくは2500~1000000であり、さらに好ましくは3000~100000である。
本発明の高分子化合物中の式(2)で表される構造単位は、化合物中に少なくとも1つ含まれていればよい。好ましくは高分子化合物中、高分子鎖一本あたり平均2個以上、さらに好ましくは高分子鎖一本あたり平均3個以上含まれる。
本発明の化合物の好ましい一態様は、式(1)で示される構造単位(Y1が硫黄原子)と式(2)で示される構造単位(Y2が酸素原子)とを有する化合物である。
この場合、下式で定義されるP’は0.1~0.9であることが好ましく、0.2~0.8であることがより好ましく、0.4~0.8であることがさらに好ましく。0.5~0.8であることが特に好ましい。
P’=(式(1)で表される構造単位(Y1が硫黄原子)の数)/{(式(1)で表される構造単位(Y1が硫黄原子)の数))+(式(2)で表される構造単位(Y2が酸素原子)の数)}
この化合物はさらに上記式(3)で表される構造単位を含んでいてもよい。
上記式(3)で示される構造単位の定義及び具体例は前述と同じである。
この場合、下式で定義されるS’は0.10~0.80であることが好ましく、0.15~0.60であることがより好ましく、0.20~0.50であることがさらに好ましい。
S’={(式(1)で表される構造単位(Y1が硫黄原子)の数)+(式(2)で表される構造単位(Y2が酸素原子)の数)}/{(式(1)で表される構造単位(Y1が硫黄原子)の数))+(式(2)で表される構造単位(Y2が酸素原子)の数)+(式(3)で表される構造単位の数)}
Q100−E1−Q200 (100)
〔式中、E1は、芳香環を含む2価の基を表す。Q100及びQ200は、同一又は相異なり、ジヒドロキシボリル基[−B(OH)2]又はホウ酸エステル残基を表す。〕
で表される1種類以上の化合物と、式(200):
T1−E2−T2 (200)
〔式中、E2は、式(1)で表される構造単位を表す。T1及びT2は、同一又は相異なり、ハロゲン原子又はスルホン酸残基を表す。〕
で表される1種類以上の化合物とを、パラジウム触媒及び塩基の存在下で反応させる工程を有する製造方法が挙げられる。E1として好ましくはアリーレン基、ヘテロアリーレン基であり、さらに好ましくは前述の式1~式255で表される基が挙げられる。
(式中、Meはメチル基を表し、Etはエチル基を表す。)
で表される基が例示される。
パラジウム触媒の添加量は、特に限定されず、触媒としての有効量であればよいが、式(100)で表される化合物1モルに対して、通常、0.0001モル~0.5モル、好ましくは0.0003モル~0.1モルである。
塩基の添加量は、式(100)で表される化合物1モルに対して、通常、0.5モル~100モル、好ましくは0.9モル~20モル、さらに好ましくは1モル~10モルである。
なお、塩基を水溶液として加え、2相系で反応させる場合は、必要に応じて、第4級アンモニウム塩などの相間移動触媒を加えてもよい。
Q300−E3−Q400 (300)
〔式中、E3は、芳香環を含む2価の基を表す。Q300及びQ400は、同一又は相異なり、置換スタンニル基を表す。〕
で表される1種類以上の化合物と、前記式(200)で表される1種類以上の化合物とを、パラジウム触媒の存在下で反応させる工程を有する製造方法が挙げられる。E3として好ましくはアリーレン基、ヘテロアリーレン基であり、さらに好ましくは前述の式1~式255で表される基である。
アルキル基の炭素数は通常1~30であり、具体例としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル墓、n−ペンチル基、イソペンチル基、2−メチルブチル基、1−メチルブチル基、n−ヘキシル基、イソヘキシル基、3−メチルペンチル基、2一メチルペンチル基、1−メチルペンチル基、ヘプチル基、オクチル基、イソオクチル基、2−エチルヘキシル基、ノニル基、デシル基、ウンデシル基、ドデシル基、テトラデシル基、ヘキサデシル墓、オクタデシル基、エイコシル基等が挙げられる。シクロアルキル基の炭素数は通常3~30であり、具体例としては、シクロペンチル基、シクロヘキシル基、アダマンチル基等が挙げられる。アリール基としてはフェニル基、ナフチル基などが挙げられる。置換スタンニル基として好ましくは−SnMe3、−SnEt3、−SnBu3、−SnPh3であり、さらに好ましくは−SnMe3、−SnEt3、−SnBu3である。上記好ましい例において、Meはメチル基を、Etはエチル基を、Buはブチル基を、Phはフェニル基を表す。
Stilleカップリング反応に使用するパラジウム触媒としては、例えば、Pd(0)触媒、Pd(II)触媒が挙げられる。具体的には、パラジウム[テトラキス(トリフェニルホスフィン)]、パラジウムアセテート類、ジクロロビス(トリフェニルホスフィン)パラジウム、パラジウムアセテート、トリス(ジベンジリデンアセトン)ジパラジウム、ビス(ジベンジリデンアセトン)パラジウムが挙げられ、反応(重合)操作の容易さ、反応(重合)速度の観点からは、パラジウム[テトラキス(トリフェニルホスフィン)]、トリス(ジベンジリデンアセトン)ジパラジウムが好ましい。
Stilleカップリング反応に使用するパラジウム触媒の添加量は、特に限定されず、触媒としての有効量であればよいが、式(100)で表される化合物1モルに対して、通常、0.0001モル~0.5モル、好ましくは0.0003モル~0.2モルである。
配位子又は助触媒を用いる場合、配位子又は助触媒の添加量は、パラジウム触媒1モルに対して、通常、0.5モル~100モルであり、好ましくは0.9モル~20モル、さらに好ましくは1モル~10モルである。
前記反応を行う時間(反応時間)は、目的の重合度に達したときを終点としてもよいが、通常、0.1時間~200時間程度である。1時間~30時間程度が効率的で好ましい。
元素分析の方法としては、原子吸光分析、発光分光分析、プラズマ発光分析、蛍光X線分析、プラズマ質量分析、グロー放電質量分析、イオンクロマトグラフ分析などが挙げられる。
置換シリル基としては、−SiR500 3で表される基が挙げられる。ここで、ここでR500は1価の有機基を表す。1価の有機基としては、アルキル基、シクロアルキル基、アリール基などが挙げられる。
式501~式652で表される化合物の中でも、重合した化合物を含む光電変換素子の光電変換効率を高める観点からは、式501~式510、式531~式550、式571~式590、式611~式620、式621、式624、式625、式628、式629、式632、式633~642、式643~式652が好ましい。さらに好ましくは式501~式510、式541~式550、式581~式590、式621、式625、式629、式633~式637、式643~式647で表される化合物である。さらにより好ましくは、式501、式507、式541、式547、式581、式587、式621、式634、式643で表される化合物である。合成の容易さからは、式501、式507、式541、式581、式634、式643で表される化合物が好ましい。
(式中、Y1は前記と同じ意味を表す。)
で表される化合物は、式(4−2)
(式中、Y1は前記と同じ意味を表す。)
で表される化合物を臭素化することで製造することが可能である。
溶媒を用いる場合、反応に用いられる溶媒としては、ペンタン、ヘキサン、ヘプタン、オクタン、シクロヘキサンなどの飽和炭化水素、ベンゼン、トルエン、エチルベンゼン、キシレンなどの不飽和炭化水素、四塩化炭素、クロロホルム、ジクロロメタン、クロロブタン、ブロモブタン、クロロペンタン、ブロモペンタン、クロロヘキサン、ブロモヘキサン、クロロシクロヘキサン、ブロモシクロヘキサンなどのハロゲン化飽和炭化水素、クロロベンゼン、ジクロロベンゼン、トリクロロベンゼンなどのハロゲン化不飽和炭化水素などが挙げられる。
臭素化剤としては臭素、N−ブロモスクシンイミド(以下、NBSと呼称することもある)、四塩化炭素、臭化水素酸などが挙げられる。これらの臭素化剤を複数組み合わせて使用することも可能である。臭素化剤の使用量は、式(4−2)で表される化合物のモル数に対して、通常2~100000当量である。
反応後は、例えば、水を加えて反応を停止した後に生成物を有機溶媒で抽出し、溶媒を留去するなどの通常の後処理を行い、式(4−1)で表される化合物を得ることができる。生成物の単離後及び精製はクロマトグラフィーによる分取や再結晶などの方法により行うことができる。
測定には、紫外、可視、近赤外の波長領域で動作する分光光度計(例えば、日本分光製、紫外可視近赤外分光光度計JASCO−V670)を用いる。JASCO−V670を用いる場合、測定可能な波長範囲が200~1500nmであるため、該波長範囲で測定を行う。まず、測定に用いる基板の吸収スペクトルを測定する。基板としては、石英基板、ガラス基板等を用いる。次いで、その基板の上に化合物を含む溶液若しくは化合物を含む溶融体から化合物を含む薄膜を形成する。溶液からの製膜では、製膜後乾燥を行う。その後、薄膜と基板との積層体の吸収スペクトルを得る。薄膜と基板との積層体の吸収スペクトルと基板の吸収スペクトルとの差を、薄膜の吸収スペクトルとして得る。
該薄膜の吸収スペクトルは、縦軸が化合物の吸光度を、横軸が波長を示す。最も大きい吸収ピークの吸光度が0.5~2程度になるよう、薄膜の膜厚を調整することが望ましい。吸収ピークの中で一番長波長の吸収ピークの吸光度を100%とし、その50%の吸光度を含む横軸(波長軸)に平行な直線と該吸収ピークとの交点であって、該吸収ピークのピーク波長よりも長波長である交点を第1の点とする。その25%の吸光度を含む波長軸に平行な直線と該吸収ピークとの交点であって、該吸収ピークのピーク波長よりも長波長である交点を第2の点とする。第1の点と第2の点とを結ぶ直線と基準線の交点を光吸収末端波長と定義する。ここで、基準線とは、最も長波長の吸収ピークにおいて、該吸収ピークの吸光度を100%とし、その10%の吸光度を含む波長軸に平行な直線と該吸収ピークの交点であって、該吸収ピークのピーク波長よりも長波長である交点の波長を基準として、基準となる波長より100nm長波長である吸収スペクトル上の第3の点と、基準となる波長より150nm長波長である吸収スペクトル上と第4の点を結んだ直線をいう。
本発明の化合物を有する光電変換素子は、第1の電極と第2の電極との間に、本発明の化合物を含む1層以上の活性層を有する。
本発明の化合物を有する光電変換素子の好ましい形態としては、少なくとも一方が透明又は半透明である一対の電極と、p型の有機半導体とn型の有機半導体との有機組成物から形成される活性層を有する。本発明の化合物は、p型の有機半導体として用いることが好ましい。この形態の光電変換素子の動作機構を説明する。透明又は半透明の電極から入射した光エネルギーがフラーレン誘導体等の電子受容性化合物(n型の有機半導体)及び/又は本発明の化合物等の電子供与性化合物(p型の有機半導体)で吸収され、電子とホールが結合した励起子を生成する。生成した励起子が移動して、電子受容性化合物と電子供与性化合物が隣接しているヘテロ接合界面に達すると、界面でのそれぞれのHOMOエネルギー及びLUMOエネルギーの違いにより電子とホールが分離し、独立に動くことができる電荷(電子とホール)が発生する。発生した電荷は、それぞれ電極へ移動することにより外部へ電気エネルギー(電流)として取り出すことができる。
電極材料として、ポリアニリン及びその誘導体、ポリチオフェン及びその誘導体等の有機の透明導電膜を用いてもよい。
前記活性層は、本発明の化合物を一種単独で含んでいても二種以上を組み合わせて含んでいてもよい。前記活性層のホール輸送性を高めるため、前記活性層中に電子供与性化合物及び/又は電子受容性化合物として、本発明の化合物以外の化合物を混合して用いることもできる。なお、前記電子供与性化合物、前記電子受容性化合物は、これらの化合物のエネルギー準位のエネルギーレベルから相対的に決定される。
フラーレン、フラーレン誘導体としてはC60、C70、C76、C78、C84及びその誘導体が挙げられる。フラーレン誘導体は、フラーレンの少なくとも一部が修飾された化合物を表す。
(式(I)~(IV)中、Raは、アルキル基、アリール基、ヘテロアリール基又はエステル構造を有する基である。複数個あるRaは、同一であっても相異なってもよい。Rbはアルキル基又はアリール基を表す。複数個あるRbは、同一であっても相異なってもよい。)
(式中、u1は、1~6の整数を表す、u2は、0~6の整数を表す、Rcは、アルキル基、アリール基又はヘテロアリール基を表す。)
光電変換素子の好ましい製造方法は、第1の電極と第2の電極とを有し、該第1の電極と該第2の電極との間に活性層を有する素子の製造方法であって、該第1の電極上に本発明の化合物と溶媒とを含む溶液(インク)を塗布法により塗布して活性層を形成する工程、該活性層上に第2の電極を形成する工程を有する素子の製造方法である。
成膜性の観点からは、25℃における溶媒の表面張力が15mN/mより大きいことが好ましく、15mN/mより大きく100mN/mよりも小さいことがより好ましく、25mN/mより大きく60mN/mよりも小さいことがさらに好ましい。
本発明の化合物は、有機薄膜トランジスタにも用いることができる。有機薄膜トランジスタとしては、ソース電極及びドレイン電極と、これらの電極間の電流経路となる有機半導体層(活性層)と、この電流経路を通る電流量を制御するゲート電極とを備えた構成を有するものが挙げられ、有機半導体層が上述した有機薄膜によって構成されるものである。このような有機薄膜トランジスタとしては、電界効果型、静電誘導型等が挙げられる。
特に、ソース電極及びドレイン電極が、有機半導体層(活性層)に接して設けられており、さらに有機半導体層に接した絶縁層を挟んでゲート電極が設けられていることが好ましい。電界効果型有機薄膜トランジスタにおいては、有機半導体層が、本発明の化合物を含む有機薄膜によって構成される。
本発明の化合物を用いた光電変換素子は、透明又は半透明の電極から太陽光等の光を照射することにより、電極間に光起電力が発生し、有機薄膜太陽電池として動作させることができる。有機薄膜太陽電池を複数集積することにより有機薄膜太陽電池モジュールとして用いることもできる。
上述の有機薄膜トランジスタは、例えば電気泳動ディスプレイ、液晶ディスプレイ、有機エレクトロルミネッセンスディスプレイ等の画素の制御や、画面輝度の均一性や画面書き換え速度を制御のために用いられる画素駆動素子等として用いることができる。
有機薄膜太陽電池は、従来の太陽電池モジュールと基本的には同様のモジュール構造をとりうる。太陽電池モジュールは、一般的には金属、セラミック等の支持基板の上にセルが構成され、その上を充填樹脂や保護ガラス等で覆い、支持基板の反対側から光を取り込む構造をとるが、支持基板に強化ガラス等の透明材料を用い、その上にセルを構成してその透明の支持基板側から光を取り込む構造とすることも可能である。具体的には、スーパーストレートタイプ、サブストレートタイプ、ポッティングタイプと呼ばれるモジュール構造、アモルファスシリコン太陽電池などで用いられる基板一体型モジュール構造等が知られている。本発明の化合物を用いて製造される有機薄膜太陽電池も使用目的や使用場所及び環境により、適宜これらのモジュール構造を選択できる。
支持基板の周囲は、内部の密封及びモジュールの剛性を確保するため金属製のフレームでサンドイッチ状に固定し、支持基板とフレームの間は封止材料で密封シールする。セルそのものや支持基板、充填材料及び封止材料に可撓性の素材を用いれば、曲面の上に太陽電池を構成することもできる。
ポリマーフィルム等のフレキシブル支持体を用いた太陽電池の場合、ロール状の支持体を送り出しながら順次セルを形成し、所望のサイズに切断した後、周縁部をフレキシブルで防湿性のある素材でシールすることにより電池本体を作製できる。Solar Energy Materials and Solar Cells,48,p383−391記載の「SCAF」とよばれるモジュール構造とすることもできる。更に、フレキシブル支持体を用いた太陽電池は曲面ガラス等に接着固定して使用することもできる。
本発明の化合物は、有機エレクトロルミネッセンス素子(有機EL素子)に用いることもできる。有機EL素子は、第1の電極と第2の電極との間に発光層を有する。有機EL素子は、発光層の他にも、正孔輸送層、電子輸送層を含んでいてもよい。該発光層、正孔輸送層、電子輸送層のいずれかの層中に本発明の化合物が含まれる。発光層中には、本発明の化合物の他にも、電荷輸送材料(電子輸送材料と正孔輸送材料の総称を意味する)を含んでいてもよい。有機EL素子としては、陽極と発光層と陰極とを有する素子、さらに陰極と発光層の間に、該発光層に隣接して電子輸送材料を含有する電子輸送層を有する陽極と発光層と電子輸送層と陰極とを有する素子、さらに陽極と発光層の間に、該発光層に隣接して正孔輸送材料を含む正孔輸送層を有する陽極と正孔輸送層と発光層と陰極とを有する素子、陽極と正孔輸送層と発光層と電子輸送層と陰極とを有する素子等が挙げられる。第1の電極と第2の電極の少なくとも一方は、透明又は半透明であることが好ましい。
本発明の化合物は有機電界効果型トランジスタ(OFET)センサの製造に用いることができる。本発明のOFETセンサは入力信号を電気信号として出力する際の信号変換素子として有機電界効果型トランジスタを用いたものであり、金属−絶縁膜−半導体構造中のいずれかに感応性あるいは選択性を付与したものである。本発明のOFETセンサとしてはバイオセンサ、ガスセンサ、イオンセンサ、湿度センサなどがあげられる。
前記チャネル領域を感圧部とする場合、有機半導体の結晶性を高めるため、配向層を有していてもよい。配向層としてはゲート絶縁膜上にヘキサメチルジシラザン等のシランカップリング剤で作成した単分子膜等が挙げられる。
別の300mLフラスコに化合物1を2.00g(12.8mmol)と脱水THF 20mLを入れて均一溶液とした。フラスコを−78℃に冷却し、上記の溶液Aを5分かけて滴下した。滴下後、5分間−78℃で攪拌し、その後、トリメチルシリルクロリド3.63mL(33.4mmol)を5分かけて滴下した。滴下後、フラスコを10分かけて室温まで昇温し、その後、室温で2時間攪拌した。その後、水を加えて反応を停止し、酢酸エチルで抽出した。有機層を硫酸ナトリウムで乾燥し、エバポレーターで溶媒を留去した。得られた固体をヘキサンに溶解させ、シリカゲルカラムクロマトグラフィーを通過させた。ろ液の溶媒をエバポレーターで留去して、目的の化合物2を3.33g(11.1mmol)得た。収率は86.5%であった。
フラスコ内の気体をアルゴンで置換した200mLフラスコに、国際公開第2011/052709号に記載された方法で合成した化合物4を203.6mg(0.193mmol)、国際公開第2011/052709号に記載された方法で合成した化合物5を214.5mg(0.193mmol)、国際公開第2011/052709号に記載された方法で合成した化合物6を61.3mg(0.186mmol)、上記合成例2で合成した化合物3を58.3g(0.186mmol)、トリス(2−トルイル)ホスフィンを10.2mg(0.033mmol)、トルエンを25ml入れて均一な溶液とした。得られたトルエン溶液を、アルゴンで30分バブリングした。その後、トルエン溶液に、トリス(ジベンジリデンアセトン)ジパラジウムを5.10mg(0.0056mmol)加え、100℃で4時間攪拌した。その後、反応液にフェニルブロミド254mgを加えて100℃で1時間反応させた。その後、フラスコを25℃に冷却し、反応液をメタノール300mLに注いだ。析出したポリマーを濾過して集め、得られたポリマーをo−ジクロロベンゼン25mLに溶解させ、アルミナ/シリカゲルカラムに通した。得られた溶液をメタノールに注いでポリマーを析出させ、ポリマーを濾過後、乾燥させ、精製された重合体を210mg得た。以下、この重合体を高分子化合物Aと呼称する。
(インク及び有機薄膜太陽電池の作製及び評価)
スパッタ法によりITO膜を150nmの厚みで付けたガラス基板を、オゾンUV装置を用いて表面処理を行った。次に、高分子化合物A及びフェニルC61−酪酸メチルエステル(フラーレンC60PCBM)(フロンティアカーボン社製)を、高分子化合物Aに対するフラーレンC60PCBMの重量比が2となるよう、オルトジクロロベンゼンに溶解させ、インク1を製造した。インク1中、高分子化合物Aの重量とフラーレンC60PCBMの重量との合計は、インク1の重量に対して2.0重量%であった。該インク1をスピンコートによりガラス基板の酸化インジウムスズ(ITO)膜上に塗布して、高分子化合物Aを含む有機膜を作製した。該有機膜の膜厚は、約100nmであった。有機膜の光吸収末端波長を測定したところ、890nmであった。その後、有機膜上に、真空蒸着機によりカルシウムを厚さ42nmで蒸着し、次いでアルミニウムを厚さ100nmで蒸着し、有機薄膜太陽電池を作製した。得られた有機薄膜太陽電池の形状は、2mm×2mmの正方形であった。得られた有機薄膜太陽電池にソーラシミュレーター(分光計器製、商品名OTENTO−SUNII:AM1.5Gフィルター、放射照度100mW/cm2)を用いて一定の光を照射し、発生する電流と電圧を測定して光電変換効率、短絡電流密度、開放電圧、フィルファクターを求めた。Jsc(短絡電流密度)は13.9mA/cm2であり、Voc(開放端電圧)は0.793Vであり、FF(フィルファクター(曲線因子))は0.639であり、光電変換効率(η)は7.02%であった。
(高分子化合物Bの合成)
フラスコ内の気体をアルゴンで置換した1000mLフラスコに、国際公開第2011/052709号に記載された方法で合成した化合物4を3200mg(3.039mmol)、国際公開第2011/052709号に記載された方法で合成した化合物5を3371mg(3.039mmol)、国際公開第2011/052709号に記載された方法で合成した化合物6を2100mg(6.365mmol)、トリス(2−トルイル)ホスフィンを174.3mg(0.573mmol)、トルエンを435ml入れて均一な溶液とした。得られたトルエン溶液を、アルゴンで30分バブリングした。その後、トルエン溶液に、トリス(ジベンジリデンアセトン)ジパラジウムを87.42mg(0.0955mmol)加え、100℃で5時間攪拌した。その後、反応液にフェニルブロミド4127mgを加えて100℃で1時間反応させた。その後、フラスコを25℃に冷却し、反応液をメタノール2000mLに注いだ。析出したポリマーを濾過して集め、得られたポリマーをo−ジクロロベンゼン413mLに溶解させ、アルミナ/シリカゲルカラムに通した。得られた溶液をメタノールに注いでポリマーを析出させ、ポリマーを濾過後、乾燥させ、精製された重合体を3980mg得た。以下、この重合体を高分子化合物Bと呼称する。
(インク及び有機薄膜太陽電池の作製及び評価)
高分子化合物Aの代わりに高分子化合物Bを用いた以外は実施例2と同様にして有機薄膜太陽電池を作成し、実施例2と同様の方法で光電変換効率、短絡電流密度、開放電圧、フィルファクターを求めた。Jsc(短絡電流密度)は15.0mA/cm2であり、Voc(開放端電圧)は0.712Vであり、FF(フィルファクター(曲線因子))は0.637であり、光電変換効率(η)は6.81%であった。
(高分子化合物Cの合成)
フラスコ内の気体をアルゴンで置換した100mLフラスコに、国際公開第2011/052709号に記載された方法で合成した化合物4を167.7mg(0.159mmol)、国際公開第2011/052709号に記載された方法で合成した化合物5を176.7mg(0.159mmol)、合成例2で合成した化合物3を100mg(0.319mmol)、トリス(2−トルイル)ホスフィンを8.70mg(0.029mmol)、トルエンを23ml入れて均一な溶液とした。得られたトルエン溶液を、アルゴンで30分バブリングした。その後、トルエン溶液に、トリス(ジベンジリデンアセトン)ジパラジウムを4.38mg(0.0048mmol)加え、100℃で8時間攪拌した。その後、反応液にフェニルブロミド209mgを加えて100℃で1時間反応させた。その後、フラスコを25℃に冷却し、反応液をメタノール100mLに注いだ。析出したポリマーを濾過して集め、得られたポリマーをo−ジクロロベンゼン21mLに溶解させ、アルミナ/シリカゲルカラムに通した。得られた溶液をメタノールに注いでポリマーを析出させ、ポリマーを濾過後、乾燥させ、精製された重合体を130mg得た。以下、この重合体を高分子化合物Cと呼称する。
(インク及び有機薄膜太陽電池の作製及び評価)
高分子化合物Aの代わりに高分子化合物Cを用いた以外は実施例2と同様にして有機薄膜太陽電池を作成し、実施例2と同様の方法で光電変換効率、短絡電流密度、開放電圧、フィルファクターを求めた。Jsc(短絡電流密度)は0.21mA/cm2であり、Voc(開放端電圧)は0.891Vであり、FF(フィルファクター(曲線因子))は0.421であり、光電変換効率(η)は0.787%であった。
フラスコ内の気体をアルゴンで置換した200mLフラスコに、化合物4を293.8mg(279.0mmol)、化合物5を309.5mg(279.0mmol)、化合物6を125.0mg(378.9mmol)、化合物3を50.9mg(162.4mmol)、トリス(2−トルイル)ホスフィンを12.2mg(0.040mmol)、トルエンを32ml入れて均一な溶液とした。得られたトルエン溶液を、アルゴンで30分バブリングした。その後、トルエン溶液に、トリス(ジベンジリデンアセトン)ジパラジウムを6.0mg(0.0065mmol)加え、100℃で4時間攪拌した。その後、反応液にフェニルブロミド284mgを加えて100℃で1時間反応させた。その後、フラスコを25℃に冷却し、反応液をメタノール400mLに注いだ。析出したポリマーを濾過して集め、得られたポリマーをo−ジクロロベンゼン33mLに溶解させ、アルミナ/シリカゲルカラムに通した。得られた溶液をメタノールに注いでポリマーを析出させ、ポリマーを濾過後、乾燥させ、精製された重合体を246mg得た。以下、この重合体を高分子化合物Dと呼称する。
(インク及び有機薄膜太陽電池の作製及び評価)
高分子化合物Aの代わりに高分子化合物Dを用いた以外は実施例2と同様にして有機薄膜太陽電池を作成し、実施例2と同様の方法で光電変換効率、短絡電流密度、開放電圧、フィルファクターを求めた。Jsc(短絡電流密度)は15.4mA/cm2であり、Voc(開放端電圧)は0.738Vであり、FF(フィルファクター(曲線因子))は0.627であり、光電変換効率(η)は7.12%であった。
フラスコ内の気体をアルゴンで置換した200mLフラスコに、化合物4を284.5mg(270.2mmol)、化合物5を128.4mg(115.8mmol)、化合物6を61.3mg(0.186mmol)、化合物3を58.3mg(0.186mmol)、トリス(2−トルイル)ホスフィンを10.2mg(0.033mmol)、トルエンを25ml入れて均一な溶液とした。得られたトルエン溶液を、アルゴンで30分バブリングした。その後、トルエン溶液に、トリス(ジベンジリデンアセトン)ジパラジウムを5.10mg(0.0056mmol)加え、100℃で4時間攪拌した。その後、反応液にフェニルブロミド254mgを加えて100℃で1時間反応させた。その後、フラスコを25℃に冷却し、反応液をメタノール300mLに注いだ。析出したポリマーを濾過して集め、得られたポリマーをo−ジクロロベンゼン25mLに溶解させ、アルミナ/シリカゲルカラムに通した。得られた溶液をメタノールに注いでポリマーを析出させ、ポリマーを濾過後、乾燥させ、精製された重合体を198mg得た。以下、この重合体を高分子化合物Eと呼称する。
(インク及び有機薄膜太陽電池の作製及び評価)
高分子化合物Aの代わりに高分子化合物Eを用いた以外は実施例2と同様にして有機薄膜太陽電池を作成し、実施例2と同様の方法で光電変換効率、短絡電流密度、開放電圧、フィルファクターを求めた。Jsc(短絡電流密度)は14.0mA/cm2であり、Voc(開放端電圧)は0.795Vであり、FF(フィルファクター(曲線因子))は0.638であり、光電変換効率(η)は7.10%であった。
Claims (11)
- 式(1)で表される構造単位と式(2)で表される構造単位とを有する化合物。
〔式中、X1、X2、X3及びX4は、同一又は相異なり、窒素原子又は
=CH−を表す。Y1及びY2は、同一又は相異なり、硫黄原子、酸素原子、セレン原子、−N(R1)−又は−CR2=CR3−を表す。R1、R2及びR3は、同一又は相異なり、水素原子、ハロゲン原子、アミノ基、シアノ基又は1価の有機基を表す。W1及びW3は、同一又は相異なり、ハロゲン原子、シアノ基、又は1価の有機基を表す。W2及びW4は、同一又は相異なり、水素原子、ハロゲン原子、シアノ基又は1価の有機基を表す。ただし、式(1)で表される構造単位と式(2)で表される構造単位とは同一ではない。〕 - Y1とY2が同一ではない請求項1記載の化合物。
- W1、W2、W3及びW4がいずれもハロゲン原子である請求項1または2記載の化合物。
- Ar1が、ヘテロアリーレン基である請求項4に記載の化合物。
- ヘテロアリーレン基がチオフェン環を含む基である請求項4または5に記載の化合物。
- 高分子化合物である請求項1~6のいずれか一項に記載の化合物。
- ポリスチレン換算の重量平均分子量が3×103以上である請求項7に記載の高分子化合物。
- 第1の電極と第2の電極とを有し、該第1の電極と該第2の電極との間に活性層を有し、該活性層に請求項1~6のいずれか一項に記載の化合物、または請求項7もしくは8に記載の高分子化合物を含有する光電変換素子。
- ゲート電極と、ソース電極と、ドレイン電極と、活性層とを有し、該活性層に請求項1~6のいずれか一項に記載の化合物、または請求項7もしくは8に記載の高分子化合物を含有する有機薄膜トランジスタ。
- 請求項1~6のいずれか一項に記載の化合物、または請求項7もしくは8に記載の高分子化合物を含有するセンサ。
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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US15/109,674 US10777746B2 (en) | 2014-01-20 | 2015-01-19 | Compound and electronic device |
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