JP5995594B2 - 高分子化合物及びそれを用いた有機トランジスタ - Google Patents
高分子化合物及びそれを用いた有機トランジスタ Download PDFInfo
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- JP5995594B2 JP5995594B2 JP2012172794A JP2012172794A JP5995594B2 JP 5995594 B2 JP5995594 B2 JP 5995594B2 JP 2012172794 A JP2012172794 A JP 2012172794A JP 2012172794 A JP2012172794 A JP 2012172794A JP 5995594 B2 JP5995594 B2 JP 5995594B2
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- 150000001875 compounds Chemical class 0.000 title claims description 116
- 229920000642 polymer Polymers 0.000 title claims description 105
- 125000001424 substituent group Chemical group 0.000 claims description 225
- 239000010410 layer Substances 0.000 claims description 98
- 125000000623 heterocyclic group Chemical group 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 125000004414 alkyl thio group Chemical group 0.000 claims description 33
- 239000004065 semiconductor Substances 0.000 claims description 31
- 239000000463 material Substances 0.000 claims description 29
- 125000002252 acyl group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 238000005227 gel permeation chromatography Methods 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 229920000547 conjugated polymer Polymers 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- -1 n-octyl group Chemical group 0.000 description 91
- 239000000758 substrate Substances 0.000 description 59
- 125000005843 halogen group Chemical group 0.000 description 37
- 230000005669 field effect Effects 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 125000004432 carbon atom Chemical group C* 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- 125000004423 acyloxy group Chemical group 0.000 description 23
- 238000006116 polymerization reaction Methods 0.000 description 23
- 125000000304 alkynyl group Chemical group 0.000 description 22
- 125000005110 aryl thio group Chemical group 0.000 description 22
- 125000004104 aryloxy group Chemical group 0.000 description 22
- 125000003342 alkenyl group Chemical group 0.000 description 21
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 125000003277 amino group Chemical group 0.000 description 20
- 125000003368 amide group Chemical group 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 0 CC1=C(C)N=C(C)*1 Chemical compound CC1=C(C)N=C(C)*1 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- 150000001721 carbon Chemical group 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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- 125000004093 cyano group Chemical group *C#N 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 229940126062 Compound A Drugs 0.000 description 10
- 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 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 230000006698 induction Effects 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
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- 239000012298 atmosphere Substances 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-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
- 230000000694 effects Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 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 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 238000006619 Stille reaction Methods 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 101710162828 Flavin-dependent thymidylate synthase Proteins 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- ZSBDPRIWBYHIAF-UHFFFAOYSA-N N-acetyl-acetamide Natural products CC(=O)NC(C)=O ZSBDPRIWBYHIAF-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 101710135409 Probable flavin-dependent thymidylate synthase Proteins 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 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 2
- 125000005619 boric acid group Chemical group 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 229910003437 indium oxide Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920005596 polymer binder Polymers 0.000 description 2
- 239000002491 polymer binding agent Substances 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000012756 surface treatment agent Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- FMYXZXAKZWIOHO-UHFFFAOYSA-N trichloro(2-phenylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CCC1=CC=CC=C1 FMYXZXAKZWIOHO-UHFFFAOYSA-N 0.000 description 2
- VIFIHLXNOOCGLJ-UHFFFAOYSA-N trichloro(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CC[Si](Cl)(Cl)Cl VIFIHLXNOOCGLJ-UHFFFAOYSA-N 0.000 description 2
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 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 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical group C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical group NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- WPWWHXPRJFDTTJ-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzamide Chemical group NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F WPWWHXPRJFDTTJ-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/124—Copolymers alternating
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
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Description
A環及びB環は、それぞれ独立に、芳香族炭化水素環または複素環である。
Ar1及びAr2は、それぞれ独立に、式(11)で表される基または式(12)で表される基である。
R1は、水素原子、置換基を有していてもよいアルキル基、置換基を有していてもよいアルコキシ基、置換基を有していてもよいアルキルチオ基、置換基を有していてもよいアリール基、置換基を有していてもよい1価の複素環基、置換基を有していてもよいアリールオキシ基、置換基を有していてもよいアリールチオ基、置換基を有していてもよいアルケニル基、置換基を有していてもよいアルキニル基、置換基を有していてもよいアミノ基、置換基を有していてもよいシリル基、ハロゲン原子、置換基を有していてもよいアシル基、置換基を有していてもよいアシルオキシ基、置換基を有していてもよいアミド基、カルボキシル基、ニトロ基又はシアノ基である。各々のR1は互いに同一でも異なっていてもよい。式(1)に含まれる2つ以上のR1が、置換基を有していてもよいアルキル基、置換基を有していてもよいアルコキシ基、置換基を有していてもよいアルキルチオ基、置換基を有していてもよいアリール基、置換基を有していてもよい1価の複素環基、置換基を有していてもよいアリールオキシ基、置換基を有していてもよいアリールチオ基、置換基を有していてもよいアルケニル基、置換基を有していてもよいアルキニル基、置換基を有していてもよいアミノ基、置換基を有していてもよいシリル基、ハロゲン原子、置換基を有していてもよいアシル基、置換基を有していてもよいアシルオキシ基、置換基を有していてもよいアミド基、カルボキシル基、ニトロ基又はシアノ基である。R1が複数個存在する場合、各々のR1は互いに同一でも異なっていてもよい。
nは正の整数である。〕
E1は、−O−で表される基、−S−で表される基、−Se−で表される基又は−N(RN)−で表される基である。RNは、水素原子、置換基を有していてもよいアルキル基、置換基を有していてもよいアリール基、置換基を有していてもよい1価の複素環基又は置換基を有していてもよいアシル基である。
Xは、=CH−で表される基又は=N−で表される基である。
*は、隣接する構造単位との結合手であることを示す。
R1は前記と同じ意味を表す。〕
〔2〕式(1)で表される構造単位が、式(2)で表される構造単位である上記〔1〕に記載の高分子化合物。
〔3〕式(2)で表される構造単位が、式(2’)で表される構造単位である上記〔2〕に記載の高分子化合物。
〔4〕式(1)で表される構造単位が、式(3)で表される構造単位である上記〔1〕に記載の高分子化合物。
〔5〕式(3)で表される構造単位が、式(3’)で表される構造単位である上記〔4〕に記載の高分子化合物。
〔6〕C1環及びC2環が、式(4)〜式(6)で表されるいずれかである上記〔4〕又は〔5〕に記載の高分子化合物。
〔7〕E1が、−S−で表される基又は−O−で表される基である上記〔2〕〜〔6〕のいずれか一項に記載の高分子化合物。
〔8〕Xが、=CH−で表される基である上記〔2〕〜〔7〕のいずれか一項に記載の高分子化合物。
〔9〕式(7)で表される構造単位を更に有する、上記〔1〕〜〔8〕のいずれか一項に記載の高分子化合物。
〔10〕共役高分子化合物である上記〔1〕〜〔9〕のいずれか一項に記載の高分子化合物。
〔11〕上記〔1〕〜〔10〕のいずれか一項に記載の高分子化合物を含む有機半導体材料。
〔12〕上記〔11〕に記載の有機半導体材料を含む有機層を有する有機半導体素子。
〔13〕ソース電極、ドレイン電極、ゲート電極及び活性層を有し、該活性層に上記〔11〕に記載の有機半導体材料を含む有機トランジスタ。
(第1構造単位)
本発明の高分子化合物は、式(1)で表される構造単位(以下、第1構造単位ということがある。)を含む。第1構造単位は、高分子化合物中に一種のみ含まれていても二種以上含まれていてもよい。
第2構造単位は、式(7)で表される構造単位である。第2構造単位は、高分子化合物中に1種のみ含まれていてもよく、2種以上含まれていてもよい。
本発明の高分子化合物は、第1構造単位及び第2構造単位以外の構造単位(以下、「他の構造単位」という場合がある。)を含んでいてもよい。他の構造単位は、高分子化合物中に一種のみ含まれていても二種以上含まれていてもよい。
本発明の高分子化合物は、より優れた電界効果移動度が得られるため、共役高分子化合物であることが好ましい。
次に、本発明の高分子化合物の製造方法を説明する。
本明細書中、有機半導体材料とは、本発明の高分子化合物と、本発明の高分子化合物とは異なる化合物と、を有する有機半導体用の材料を意味する。本発明の高分子化合物とは異なる化合物は、キャリア輸送性を有する化合物であることが好ましく、低分子化合物であっても高分子化合物であってもよい。有機半導体材料に含まれる本発明の高分子化合物は、1種類単独であってもよく、2種類以上であってもよい。有機半導体材料は、本発明の高分子化合物を30重量%以上含むことが好ましく、50重量%以上含むことがより好ましい。
本発明の高分子化合物は、優れた電界効果移動度を示すことから、有機半導体素子の有機層(活性層、有機半導体層)に好適に用いることができる。有機半導体素子としては、例えば、有機トランジスタ、有機太陽電池及び有機エレクトロルミネッセンス素子が挙げられる。本発明の高分子化合物は、これらの有機半導体素子の中でも、有機トランジスタの有機層に好適に用いることができる。
本発明の有機トランジスタとしては、例えば、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であり本発明の高分子化合物を含む活性層と、該電流経路を通る電流量を制御するゲート電極とを有する有機トランジスタが挙げられる。このような構成を有する有機トランジスタとしては、例えば、電界効果型有機トランジスタ及び静電誘導型有機トランジスタ等が挙げられる。
NMR測定は、化合物を重クロロホルムに溶解させ、NMR装置(Varian社製)を用いて行った。
高分子化合物の数平均分子量及び重量平均分子量は、ゲル透過クロマトグラフィ(GPC、東ソー製)を用いて求めた。測定する高分子化合物は、オルトジクロロベンゼンに溶解させ、GPCに注入した。GPCの移動相にはオルトジクロロベンゼンを用いた。カラムは、TSKgel GMHHR−H(S)HT(2本連結、東ソー製)を用いた。検出器にはUV検出器を用いた。
高分子化合物Aを用いて図8に模式的に示す構成を有する有機トランジスタを作製し、そのトランジスタ特性を測定した。すなわち、まず、ゲート電極となる高濃度に不純物がドープされたn−型シリコン基板4の表面を熱酸化し、200nmのシリコン酸化膜3を形成した。この基板を十分に洗浄した後、ヘキサメチレンジシラザン(HMDS)を用いて、基板表面をシラン処理した。
高分子化合物Aを用いて図8に模式的に示す構成を有する有機トランジスタを作製し、そのトランジスタ特性を測定した。すなわち、まず、ゲート電極となる高濃度に不純物がドープされたn−型シリコン基板4の表面を熱酸化し、厚さ200nmのシリコン酸化膜3を形成した。この基板を十分に洗浄した後、1H,1H,2H,2H−パーフルオロデシルトリエトキシクロロシラン(FDTS)を用いて、基板表面をシラン処理した。
高分子化合物Bを用いて図8に模式的に示す構成を有する有機トランジスタを作製し、そのトランジスタ特性を測定した。すなわち、まず、ゲート電極となる高濃度に不純物がドープされたn−型シリコン基板4の表面を熱酸化し、厚さ200nmのシリコン酸化膜3を形成した。この基板を十分に洗浄した後、1H,1H,2H,2H−パーフルオロデシルトリエトキシクロロシラン(FDTS)を用いて、基板表面をシラン処理した。
高分子化合物Cを用いて図8に模式的に示す構造を有する有機トランジスタを作製し、そのトランジスタ特性を測定した。すなわち、まず、ゲート電極となる高濃度に不純物がドープされたn−型シリコン基板4の表面を熱酸化し、200nmのシリコン酸化膜3を形成した。この基板をアセトンで10分間超音波洗浄した後、オゾンUVを20分間照射した。その後、β−フェニチルトリクロロシラン(β−PTS)を用いて、スピンコート法により基板表面をシラン処理した。
Claims (13)
- 式(1)で表される構造単位を含み、ゲルパーミエーションクロマトグラフィーで測定したポリスチレン換算の重量平均分子量が1×10 3 〜1×10 6 である高分子化合物。
A環及びB環は、それぞれ独立に、芳香族炭化水素環である。
Ar1及びAr2は、それぞれ独立に、式(11)で表される基または式(12)で表される基である。
R1は、水素原子、置換基を有していてもよいアルキル基、置換基を有していてもよいアルコキシ基、又は置換基を有していてもよいアルキルチオ基である。各々のR1は互いに同一でも異なっていてもよい。式(1)に含まれる2つ以上のR1が、置換基を有していてもよいアルキル基、置換基を有していてもよいアルコキシ基、又は置換基を有していてもよいアルキルチオ基である。R1が複数個存在する場合、各々のR1は互いに同一でも異なっていてもよい。
nは正の整数である。〕
E1は、−O−で表される基、−S−で表される基、−Se−で表される基又は−N(RN)−で表される基である。RNは、水素原子、置換基を有していてもよいアルキル基、置換基を有していてもよいアリール基、置換基を有していてもよい1価の複素環基又は置換基を有していてもよいアシル基である。
Xは、=CH−で表される基、=N−で表される基である。
*は、隣接する構造単位との結合手であることを示す。
R1は前記と同じ意味を表す。〕
- E1が、−S−で表される基又は−O−で表される基である請求項2〜6のいずれか一項に記載の高分子化合物。
- Xが、=CH−で表される基である請求項2〜7のいずれか一項に記載の高分子化合物。
- 共役高分子化合物である請求項1〜9のいずれか一項に記載の高分子化合物。
- 請求項1〜10のいずれか一項に記載の高分子化合物を含む有機半導体材料。
- 請求項11に記載の有機半導体材料を含む有機層を有する有機半導体素子。
- ソース電極、ドレイン電極、ゲート電極及び活性層を有し、該活性層に請求項11に記載の有機半導体材料を含む有機トランジスタ。
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