JP6157497B2 - 有機電界効果トランジスタ - Google Patents
有機電界効果トランジスタ Download PDFInfo
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- JP6157497B2 JP6157497B2 JP2014545196A JP2014545196A JP6157497B2 JP 6157497 B2 JP6157497 B2 JP 6157497B2 JP 2014545196 A JP2014545196 A JP 2014545196A JP 2014545196 A JP2014545196 A JP 2014545196A JP 6157497 B2 JP6157497 B2 JP 6157497B2
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- 230000005669 field effect Effects 0.000 title description 9
- 239000010410 layer Substances 0.000 claims description 89
- 229920000642 polymer Polymers 0.000 claims description 74
- -1 cyano, phenyl Chemical group 0.000 claims description 71
- 239000004065 semiconductor Substances 0.000 claims description 51
- 239000002904 solvent Substances 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000000463 material Substances 0.000 claims description 35
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 16
- 238000009472 formulation Methods 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000011877 solvent mixture Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 2
- 239000000243 solution Substances 0.000 description 34
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
- 238000000151 deposition Methods 0.000 description 14
- 239000012212 insulator Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229960001701 chloroform Drugs 0.000 description 9
- 238000007641 inkjet printing Methods 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- 239000010931 gold Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 238000000059 patterning Methods 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 0 Cc1c(*)c(*)c(C)[o]1 Chemical compound Cc1c(*)c(*)c(C)[o]1 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 239000003989 dielectric material Substances 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
- 238000000206 photolithography Methods 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide 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
- 125000002511 behenyl 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])C([H])([H])C([H])([H])[H] 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000755 henicosyl 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])C([H])([H])[H] 0.000 description 3
- 125000005842 heteroatom Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002463 lignoceryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002960 margaryl 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])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 125000002958 pentadecyl 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])[H] 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 125000004079 stearyl 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])[H] 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000002889 tridecyl 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])[H] 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- MSIUQOWNDKIKSG-UHFFFAOYSA-N Cc1cc([s]c(C)c2)c2[s]1 Chemical compound Cc1cc([s]c(C)c2)c2[s]1 MSIUQOWNDKIKSG-UHFFFAOYSA-N 0.000 description 2
- GWQOOADXMVQEFT-UHFFFAOYSA-N Cc1ccc(C)[s]1 Chemical compound Cc1ccc(C)[s]1 GWQOOADXMVQEFT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910052454 barium strontium titanate Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
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- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 125000003136 n-heptyl 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])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010020 roller printing Methods 0.000 description 2
- 239000002094 self assembled monolayer Substances 0.000 description 2
- 239000013545 self-assembled monolayer Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000007764 slot die coating Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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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
- C08G61/124—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 nitrogen atom in the ring
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/105—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a methine or polymethine dye
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- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
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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]
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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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
- H10K85/10—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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- H10K85/151—Copolymers
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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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
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Description
本発明は、ゲート電極、ソース電極およびドレイン電極を含む電子素子またはデバイスであって、ソース電極とドレイン電極との間に備えられる有機半導体(OSC)材料をさらに含み、前記OSC材料が(a)式Iによって表されるポリマーおよび(b)式IIの化合物を含む、前記電子素子またはデバイスを提供する。式Iによって示されるポリマーおよび(b)式(II)の化合物から構成される半導体材料を選択することによって、高品質なOFETを製造できる。
によって表される化学構造を有する化合物を含む。とりわけ、以下のポリマーが明示されている:
(a) 式
R101およびR102は、同一または異なっていてよく、且つ、水素、C1〜C38−アルキル基、C2〜C38−アルケニル基、C3〜C38−アルキニル基であって各々随意に1つまたはそれより多くの箇所、−O−、−S−またはCOOによって中断されていてよいもの、1〜5箇所、C1〜C8−アルキル、C1〜C8−アルコキシ、CF3および/またはFで置換されていてよいC7〜C100−アリールアルキル基、および1またはそれより多くの箇所、C1〜C25−アルキル、C1〜C8−アルコキシ、ハロゲンまたはシアノによって随意に置換されていてよいフェニル基から選択される;
各々のA6およびA7は、独立して
各々のMは独立して、
R13およびR13'は互いに独立して、水素、ハロゲン、ハロゲン化されたC1〜C25−アルキル、特にCF3、シアノ、C1〜C25−アルキルであって随意に1つまたはそれより多くの酸素または硫黄原子によって中断されていてよいもの、C7〜C25−アリールアルキルまたはC1〜C25−アルコキシである;
sは1〜4の数を表し、tは1〜4の数を表し、vは0〜3の数を表し、且つ、nは少なくとも5の数を表す]
によって表されるポリマー、および
(b) 式
A1およびA2は互いに独立して、式
aは1または2であり、bは0または1であり、cは0または1である;
R1およびR2は、同一または異なっていてよく、且つ、水素、C1〜C38−アルキル基、C2〜C38−アルケニル基、C3〜C38−アルキニル基であって各々随意に1つまたはそれより多くの箇所、−O−、−S−またはCOOによって中断されていてよいもの、1〜5箇所、C1〜C8−アルキル、C1〜C8−アルコキシ、CF3および/またはFで置換されていてよいC7〜C100−アリールアルキル基、および1またはそれより多くの箇所、C1〜C25−アルキル、C1〜C8−アルコキシ、ハロゲンまたはシアノによって随意に置換されていてよいフェニル基から選択される;
Ar1、Ar2およびAr3は互いに独立して、式
R14およびR14'は互いに独立して、水素、ハロゲン、ハロゲン化されたC1〜C25−アルキル、特にCF3、シアノ、C1〜C25−アルキルであって随意に1つまたはそれより多くの酸素または硫黄原子によって中断されていてよいもの、C7〜C25−アリールアルキルまたはC1〜C25−アルコキシである;
R3は水素、ハロゲン、シアノ、C1〜C25−アルキル、ハロ−C1〜C25−アルキル、
[式中、
R22〜R25およびR29〜R33は、互いに独立してH、ハロゲン、シアノまたはC1〜C25−アルキルを表す、且つ、
R26はH、ハロゲン、シアノ、フェニルまたはC1〜C25−アルキルである]]
の化合物を含み、その際、式IIの化合物は式Iのポリマーおよび式IIの化合物の量に対して0.1〜99.9質量%の量で含有される、前記素子またはデバイスによって解決される。
a) DPPポリマーとドーパントとを連続的に堆積させ、次にドーパントを随意に熱処理によって中に拡散させる;
b) DPPポリマー層をドーパントの溶液によってドーピングし、次に溶剤を随意に熱処理によって蒸発させる;
c) DPPポリマーの溶液または分散液をドーパントの溶液によってドーピングし、次に溶剤を随意に熱処理によって蒸発させる; および
d) DPPポリマーの溶液を式IIの固体の化合物でドーピングして分散液または溶液にし、次に溶剤を随意に熱処理によって蒸発させる。
によって表すことができる。キラル側鎖、例えばR101およびR102は、ホモキラルかラセミかのいずれかであってよく、そのことが化合物の形態に影響することがある。
A6およびA7は、独立して
のポリマーである。
A6およびA7は、独立して
Mは
vは1、2または3の整数を表す、且つ、R101およびR102はC1〜C38−アルキル基であり、且つ、nは5〜1000である]
のポリマーである。
R101およびR102はC1〜C38−アルキル基であり、且つnは5〜1000である]
によって表されるポリマーがより好ましく、式(Ib−1)、(Ib−4)、(Ib−6)および(Ib−7)のポリマーがさらにより好ましく、且つ、式(Ib−1)のポリマーが最も好ましく、例えば
aは1または2である; bは0または1である; cは0または1である、
R1およびR2は同一または異なり、且つ、C1〜C38−アルキル基である、
Ar1、Ar2およびAr3は互いに独立して式
R3は水素、シアノ、
の化合物である。式IIaの化合物の例を以下に示す:
によって表すことができる。キラル側鎖、例えばR1およびR2は、ホモキラルかラセミかのいずれかであってよく、そのことが化合物の形態に影響することがある。
(a) 上記で定義された式Iのポリマー、
(b) 上記で定義された式IIの化合物、および
(c) 溶剤または溶剤混合物
を含む配合物に関する。
(a) 上記で定義された式Iのポリマー、
(b) 上記で定義された式IIの化合物、および
(c) 溶剤または溶剤混合物
を含む配合物にも関する。
(i) 式IIの化合物と式Iのポリマーとを最初に混合すること。好ましくは前記の混合は、溶剤または溶剤混合物中で成分を一緒に混合することを含む、
(ii) 式IIの化合物と式Iのポリマーとを含有する溶剤を基板に施与すること、および随意に溶剤を蒸発させて本発明による固体のOSC層を形成すること、および
(iii) 随意に、固体のOSC層を基板から除去する、または前記固体層から基板を除去すること
を含む方法によって製造できる。
固体含有率(%)=((a+b)/(a+b+c))×100、
[式中、a=式IIの化合物の質量、b=式Iのポリマーの質量、およびc=溶剤の質量]。
・ ソース電極、
・ ドレイン電極、
・ ゲート電極、
・ 半導体層、
・ 1つまたはそれより多くのゲート絶縁体層、および
・ 随意に基板
を含み、その際、前記半導体層は式IのDPPポリマーおよび式IIの化合物を含む。
1. ゲートの堆積およびパターニング(例えばITO被覆された基板のパターニング)。
2. 誘電体の堆積およびパターニング(例えば架橋可能な、フォトパターニング可能な誘電体)。
3. ソース・ドレイン材料の堆積およびパターニング(例えば銀、フォトリソグラフィー)。
4. ソース・ドレインの表面処理。基板を自己組織化材料の溶液中に浸漬させることによって表面処理基を施与できるか、または希釈溶液からスピンコーティングによって施与する。過剰な(未結合の)材料を洗浄によって除去できる。
5. 有機半導体材料を(例えばインクジェット印刷によって)堆積。
a) 基板の製造:
ポリエチレンテレフタレート(PET)のフレキシブル箔(Mitsubishi Hostaphan GN)を、30nm厚の金層で被覆する。櫛形(Interdigited)電極を金層上でのフォトリソグラフィーによって製造する。チャネル幅Lは10ミクロンであり、チャネル長Wは10000ミクロンであり、W/L比は1000になる。その後、基板をアセトンおよびイソプロパノールで入念に洗浄して、電極作製に用いられた残留フォトレジストを全て除去する。
c1) 有機半導体層
前記半導体溶液を空気中(クリーンルーム)で、清浄なフレキシブル基板上にスピンコートする。その後、その膜を90℃ホットプレート上で30秒間、空気中で乾燥させる。スピン条件(1500rpm、15秒間)は、乾燥後の半導体層の厚さが50±5nm(Dektak 6M (Veeco製)を用いて測定された厚さ)になるような条件である。
誘電体溶液は、ポリメチルメタクリレート(PMMA)の4%の酢酸ブチル/乳酸エチル(60/40)溶液である(950K(1004084、Allresist製))。該誘電体溶液を、乾燥された半導体層上にスピンコーティング(1800rpm、30秒間)によって施与し、500nm±10nmの厚さ(乾燥後)をもたらす。誘電体層を2分間、空気中、90℃で乾燥させる。該誘電体膜のキャパシタンスは、7±0.2nF/cm2である。
50nmの金を誘電体上に熱蒸着することによってゲート電極を製造する。蒸着を高真空下(<10-5Torr)で行う。
OFETの飽和移動曲線をKeithley 2612Aソースメータを用いて測定した。ゲート電圧−15Vで観察されたホール移動度(ドレイン電圧=−20Vでの飽和移動曲線から計算された6つのOFETの平均)は、0.45±0.03cm2/秒*Vであり、閾値下の振れは0.5V/DEC未満であった。閾値下の振れ(低いほうが良い)は、誘電体/半導体界面でのトラッピング状態の濃度の指標である。最高で、それは室温で60mV/decであり得る。
半導体溶液が化合物A−1を含有しないこと以外は、適用例1を繰り返す。
Claims (15)
- ゲート電極、ソース電極およびドレイン電極を含む電子素子またはデバイスであって、ソース電極とドレイン電極との間に備えられた有機半導体(OSC)材料をさらに含み、その際、前記OSC材料が以下の(a)および(b)
(a) 式
R101およびR102は、同一または異なっていてよく、且つ、C 1〜C38−アルキル基である;
各々のA6およびA7は、独立して
各々のMは独立して、
R13およびR13'は互いに独立して、水素、ハロゲン、ハロゲン化されたC1〜C25−アルキル、シアノ、C1〜C25−アルキルであって随意に1つまたはそれより多くの酸素または硫黄原子によって中断されていてよいもの、C7〜C25−アリールアルキルまたはC1〜C25−アルコキシである;
sは1〜4の数を表し、tは1〜4の数を表し、vは0〜3の数を表し、且つ、nは少なくとも5の数を表す]
によって表されるポリマー、および
(b) 式
A1およびA2は互いに独立して、式
aは1または2であり、bは0または1であり、cは0または1である;
R1およびR2は、同一または異なっていてよく、且つ、C 1〜C38−アルキル基である;
Ar1、Ar2およびAr3は互いに独立して、式
R14およびR14'は互いに独立して、水素、ハロゲン、ハロゲン化されたC1〜C25−アルキル、シアノ、C1〜C25−アルキルであって随意に1つまたはそれより多くの酸素または硫黄原子によって中断されていてよいもの、C7〜C25−アリールアルキルまたはC1〜C25−アルコキシである;
R3は水素、ハロゲン、シアノ、C1〜C25−アルキル、ハロ−C1〜C25−アルキル、
[式中、
R22〜R25およびR29〜R33は、互いに独立してH、ハロゲン、シアノまたはC1〜C25−アルキルを表す、且つ、
R26はH、ハロゲン、シアノ、フェニルまたはC1〜C25−アルキルである]]
の化合物を含み、その際、式IIの化合物は式Iのポリマーおよび式IIの化合物の量に対して0.1〜99.9質量%の量で含有される、前記素子またはデバイス。 - 式(Ib)によって表されるポリマーが、式(Ib−1)のポリマーであり、且つ式IIaの化合物が、式(IIa−1)の化合物である、請求項5および7に記載の素子またはデバイス。
- 式IIの化合物が、式Iのポリマーおよび式IIの化合物の量に対して5〜95質量%の量で含有される、請求項1から8までのいずれか1項に記載の素子またはデバイス。
- 以下の段階:
(i) 請求項1から9までのいずれか1項に定義された1つまたはそれより多くの式IIの化合物および式Iのポリマーを、随意に溶剤または溶剤混合物と混合する段階、
(ii) 前記混合物、または式IIの化合物および式Iのポリマーを含有する溶剤を、基板に施与し、且つ随意に、溶剤を蒸発させて、固体のOSC層を形成する段階
を含むことを特徴とする、請求項1から9までのいずれか1項に記載のデバイスの製造方法。 - 請求項1に定義された式Iのポリマーと、請求項1に定義された式IIの化合物とを含む有機層。
- (a) 請求項1から7までのいずれか1項に定義された式Iのポリマー、
(b) 請求項1から7までのいずれか1項に定義された式IIの化合物、および
(c) 溶剤、または溶剤混合物
を含む配合物。 - 請求項11に記載の有機層の、有機半導体デバイス内での使用。
- 有機層を製造するための請求項12に記載の配合物の使用。
- 請求項1から9までのいずれか1項に記載の素子またはデバイス、または請求項11に記載の有機層を含む装置。
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