JP5835386B2 - 有機半導体材料、有機半導体膜及び有機薄膜トランジスタ - Google Patents
有機半導体材料、有機半導体膜及び有機薄膜トランジスタ Download PDFInfo
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- JP5835386B2 JP5835386B2 JP2014056244A JP2014056244A JP5835386B2 JP 5835386 B2 JP5835386 B2 JP 5835386B2 JP 2014056244 A JP2014056244 A JP 2014056244A JP 2014056244 A JP2014056244 A JP 2014056244A JP 5835386 B2 JP5835386 B2 JP 5835386B2
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- Prior art keywords
- group
- substituted
- alkyl
- organic semiconductor
- alkyl group
- Prior art date
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- 239000004065 semiconductor Substances 0.000 title claims description 66
- 239000010408 film Substances 0.000 title claims description 51
- 239000010409 thin film Substances 0.000 title claims description 43
- 239000000463 material Substances 0.000 title claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- -1 silylethynyl group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 13
- 125000005110 aryl thio group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 238000000576 coating method Methods 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 5
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000005281 alkyl ureido group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 238000007740 vapor deposition Methods 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910005965 SO 2 Inorganic materials 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000006339 pentafluoro alkyl group Chemical group 0.000 claims description 2
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 71
- 239000010410 layer Substances 0.000 description 37
- 239000010419 fine particle Substances 0.000 description 23
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
- 239000006185 dispersion Substances 0.000 description 15
- 239000000758 substrate Substances 0.000 description 14
- 229920001940 conductive polymer Polymers 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 238000007639 printing Methods 0.000 description 10
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- 238000000059 patterning Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052738 indium Inorganic materials 0.000 description 4
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 4
- 229910052809 inorganic oxide Inorganic materials 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002985 plastic film Substances 0.000 description 4
- 229920006255 plastic film Polymers 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000004544 sputter deposition Methods 0.000 description 4
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,3-dimethylpentane Natural products CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 3
- AEXMKKGTQYQZCS-UHFFFAOYSA-N 3,3-dimethylpentane Chemical compound CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical class C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- FLTJDUOFAQWHDF-UHFFFAOYSA-N 2,2-dimethylhexane Chemical compound CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- HDGQICNBXPAKLR-UHFFFAOYSA-N 2,4-dimethylhexane Chemical compound CCC(C)CC(C)C HDGQICNBXPAKLR-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- KUMXLFIBWFCMOJ-UHFFFAOYSA-N 3,3-dimethylhexane Chemical compound CCCC(C)(C)CC KUMXLFIBWFCMOJ-UHFFFAOYSA-N 0.000 description 2
- RNTWWGNZUXGTAX-UHFFFAOYSA-N 3,4-dimethylhexane Chemical compound CCC(C)C(C)CC RNTWWGNZUXGTAX-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- DUPUVYJQZSLSJB-UHFFFAOYSA-N 3-ethyl-2-methylpentane Chemical compound CCC(CC)C(C)C DUPUVYJQZSLSJB-UHFFFAOYSA-N 0.000 description 2
- SFRKSDZMZHIISH-UHFFFAOYSA-N 3-ethylhexane Chemical compound CCCC(CC)CC SFRKSDZMZHIISH-UHFFFAOYSA-N 0.000 description 2
- AORMDLNPRGXHHL-UHFFFAOYSA-N 3-ethylpentane Chemical compound CCC(CC)CC AORMDLNPRGXHHL-UHFFFAOYSA-N 0.000 description 2
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 2
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- CHBAWFGIXDBEBT-UHFFFAOYSA-N 4-methylheptane Chemical compound CCCC(C)CCC CHBAWFGIXDBEBT-UHFFFAOYSA-N 0.000 description 2
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
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- 229920008347 Cellulose acetate propionate Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 229910001111 Fine metal Inorganic materials 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- VNSWULZVUKFJHK-UHFFFAOYSA-N [Sr].[Bi] Chemical compound [Sr].[Bi] VNSWULZVUKFJHK-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 229910002115 bismuth titanate Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Chemical class C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isononane Chemical compound CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 2
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
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- 229920005591 polysilicon Polymers 0.000 description 2
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- 229910001936 tantalum oxide Inorganic materials 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
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Images
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Description
下記一般式(ア)で表される芳香族縮合環を有する化合物であるか、又は、該化合物のベンゼン環がアルキル基、アルキル基が置換したシリルエチニル基、アルキル基が置換したアリール基、アルキルシリルエチニル基が置換したアリール基、アルキル基が置換した芳香族複素環基、アルコキシル基、シクロアルコキシル基、アルキル基が置換したアリールオキシ基、アルキルチオ基、シクロアルキルチオ基、アルキル基が置換したアリールチオ基、アルコキシカルボニル基、アルキル基が置換したアリールオキシカルボニル基、アルキルスルファモイル基、アルキルカルボニル基、アルキルカルボニルオキシ基、アルキルカルボニルアミノ基、アルキルカルバモイル基、アルキルウレイド基、アルキルスルフィニル基、アルキルスルホニル基、アルキル基が置換したアリールスルホニル基、アルキルアミノ基、フルオロアルキル基、トリフルオロアルキル基、ペンタフルオロアルキル基、アルキルシリル基又はアルキルアリールエチニル基からなる置換基を有することを特徴とする有機半導体材料。
前記1記載の有機半導体材料を含むことを特徴とする有機半導体膜。
蒸着又は塗布により形成されたことを特徴とする前記2記載の有機半導体膜。
前記有機半導体材料を少なくとも0.1%溶解してなる溶液を用いて塗布形成されたことを特徴とする前記7記載の有機半導体膜。
前記2〜4の何れかに記載の有機半導体膜を備えたことを特徴とする有機薄膜トランジスタ。
本発明の有機半導体材料は、下記一般式(ア)で表される芳香族縮合環を有する化合物である。
本発明において、有機半導体層を形成する方法としては、真空蒸着により形成する蒸着プロセス、あるいはキャストコート、ディップコート、スピンコート等の塗布法やインクジェット印刷、スクリーン印刷等の印刷法等に代表される溶液プロセス等が挙げられるが、本発明では溶液プロセスにより基板上に有機半導体膜を形成することが好ましい。
本発明において、溶液プロセスに用いられる有機溶媒は、本発明の有機半導体材料を溶解して適切な濃度の溶液が調製できるものであれば格別の制限はないが、ジエチルエーテルやジイソプロピルエーテル等の鎖状エーテル系溶媒、テトラヒドロフランやジオキサンなどの環状エーテル系溶媒、アセトンやメチルエチルケトン等のケトン系溶媒、クロロホルムや1,2−ジクロロエタン等の脂肪族ハロゲン化炭化水素系溶媒、トルエン、o−ジクロロベンゼン、ニトロベンゼン、m−クレゾール等の芳香族系溶媒、ヘキサンやシクロヘキサン等の脂肪族炭化水素系溶媒、N−メチルピロリドン、2硫化炭素等を挙げることができる。
有機薄膜トランジスタは、支持体上に有機半導体チャネル(活性層)で連結されたソース電極とドレイン電極を有し、その上にゲート絶縁層を介してゲート電極を有するトップゲート型と、支持体上に先ずゲート電極を有し、ゲート絶縁層を介して有機半導体チャネルで連結されたソース電極とドレイン電極を有するボトムゲート型に大別される。本発明の有機薄膜トランジスタは、これらトップゲート型またボトムゲート型のいずれでもよく、またその形態を問わない。
《有機薄膜トランジスタ素子の作製》
図1(f)に記載の層構成を有する有機薄膜トランジスタ素子(以下、TFT素子と呼ぶ)1を作製した。
(トランジスタ特性)
以上のように作製したTFT素子1〜15は、pチャンネルのエンハンスメント型FETの動作特性を示した。それぞれのTFT素子について、I−V特性の飽和領域からキャリア移動度を求め、更にON/OFF比(ドレインバイアス−40Vとし、ゲートバイアス−50V及び0Vにしたときのドレイン電流値の比率)を求め、結果を表1に示した。また、25℃、湿度45%の条件下で1ヶ月放置したとき、及び50℃、湿度60%の条件下で1ヶ月放置したとき、それぞれのキャリア移動度及びON/OFF比についても評価し、表1に示した。
2 ソース電極
3 ドレイン電極
4 ゲート電極
5 絶縁層
6 支持体
7 ゲートバスライン
8 ソースバスライン
10 TFTシート
11 有機TFT
12 出力素子
13 蓄積コンデンサ
14 垂直駆動回路
15 水平駆動回路
Claims (5)
- 下記一般式(ア)で表される芳香族縮合環を有する化合物であるか、又は、該化合物のベンゼン環がアルキル基、アルキル基が置換したシリルエチニル基、アルキル基が置換したアリール基、アルキルシリルエチニル基が置換したアリール基、アルキル基が置換した芳香族複素環基、アルコキシル基、シクロアルコキシル基、アルキル基が置換したアリールオキシ基、アルキルチオ基、シクロアルキルチオ基、アルキル基が置換したアリールチオ基、アルコキシカルボニル基、アルキル基が置換したアリールオキシカルボニル基、アルキルスルファモイル基、アルキルカルボニル基、アルキルカルボニルオキシ基、アルキルカルボニルアミノ基、アルキルカルバモイル基、アルキルウレイド基、アルキルスルフィニル基、アルキルスルホニル基、アルキル基が置換したアリールスルホニル基、アルキルアミノ基、フルオロアルキル基、トリフルオロアルキル基、ペンタフルオロアルキル基、アルキルシリル基又はアルキルアリールエチニル基からなる置換基を有することを特徴とする有機半導体材料。
(式中、Xは、S、Se、SO2、O、N(R3)、Si(R3)R4またはC(R3)R4を表し、R3、R4は水素原子またはアルキル基、シクロアルキル基、アリール基、芳香族複素環基、複素環基、アルコキシル基、シクロアルコキシル基、アリールオキシ基、アルキルチオ基、シクロアルキルチオ基、若しくはアリールチオ基を表すが、Xはそれぞれ異なってもよい。該化合物がベンゼン環に前記置換基を有さない場合、少なくとも一つのXは、N(R3)、Si(R3)R4またはC(R3)R4を表し、ここで、Xが、N(R3)を表すとき、R3はアルキル基、シクロアルキル基、アルキル基が置換したアリール基、アルキル基が置換した芳香族複素環基、アルキル基が置換した複素環基、アルコキシル基、シクロアルコキシル基、アルキル基が置換したアリールオキシ基、アルキルチオ基、シクロアルキルチオ基又はアルキル基が置換したアリールチオ基を表し、Xが、Si(R3)R4またはC(R3)R4を表すとき、R3、R4の少なくとも一方はアルキル基、シクロアルキル基、アルキル基が置換したアリール基、アルキル基が置換した芳香族複素環基、アルキル基が置換した複素環基、アルコキシル基、シクロアルコキシル基、アルキル基が置換したアリールオキシ基、アルキルチオ基、シクロアルキルチオ基又はアルキル基が置換したアリールチオ基を表す。前記芳香族縮合環の2位及び7位のみに置換基を有する場合は、該置換基として、アルキル基が置換したシリルエチニル基、アルキルシリルエチニル基が置換したアリール基、アルキル基が置換した芳香族複素環基、シクロアルコキシル基、アルキル基が置換したアリールオキシ基、シクロアルキルチオ基、アルキル基が置換したアリールチオ基、アルコキシカルボニル基、アルキル基が置換したアリールオキシカルボニル基、アルキルスルファモイル基、アルキルカルボニル基、アルキルカルボニルオキシ基、アルキルカルボニルアミノ基、アルキルカルバモイル基、アルキルウレイド基、アルキルスルフィニル基、アルキルスルホニル基、アルキル基が置換したアリールスルホニル基、アルキルアミノ基、アルキルシリル基又はアルキルアリールエチニル基を有する。) - 請求項1記載の有機半導体材料を含むことを特徴とする有機半導体膜。
- 蒸着又は塗布により形成されたことを特徴とする請求項2記載の有機半導体膜。
- 前記有機半導体材料を少なくとも0.1%溶解してなる溶液を用いて塗布形成されたことを特徴とする請求項7記載の有機半導体膜。
- 請求項2〜4の何れかに記載の有機半導体膜を備えたことを特徴とする有機薄膜トランジスタ。
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EP2330108A1 (en) * | 2005-01-19 | 2011-06-08 | National University of Corporation Hiroshima University | Method for the preparation of condensed polycyclic aromatic compounds |
JP5499422B2 (ja) * | 2006-06-28 | 2014-05-21 | コニカミノルタ株式会社 | 有機半導体材料、有機半導体膜、有機薄膜トランジスタ及び有機薄膜トランジスタの製造方法 |
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