US20110042658A1 - Anthanthrene based compound and semiconductor device - Google Patents
Anthanthrene based compound and semiconductor device Download PDFInfo
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- US20110042658A1 US20110042658A1 US12/821,598 US82159810A US2011042658A1 US 20110042658 A1 US20110042658 A1 US 20110042658A1 US 82159810 A US82159810 A US 82159810A US 2011042658 A1 US2011042658 A1 US 2011042658A1
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- YFIJJNAKSZUOLT-UHFFFAOYSA-N Anthanthrene Chemical compound C1=C(C2=C34)C=CC=C2C=CC3=CC2=CC=CC3=CC=C1C4=C32 YFIJJNAKSZUOLT-UHFFFAOYSA-N 0.000 title claims abstract description 126
- 150000001875 compounds Chemical class 0.000 title claims abstract description 87
- 239000004065 semiconductor Substances 0.000 title claims description 51
- 125000001424 substituent group Chemical group 0.000 claims abstract description 33
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 239000000758 substrate Substances 0.000 claims description 48
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical class 0.000 claims 4
- -1 acene compound Chemical class 0.000 description 67
- 238000000034 method Methods 0.000 description 66
- 239000000463 material Substances 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
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- 239000010931 gold Substances 0.000 description 18
- 239000011651 chromium Substances 0.000 description 14
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- 238000000576 coating method Methods 0.000 description 11
- 238000007740 vapor deposition Methods 0.000 description 11
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- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 7
- 0 [1*]C1=C([2*])C([3*])=C2C([4*])=C([5*])C3=C4C2=C1CC1=C4C2=C(C3)C([7*])=C([8*])C([9*]C)=C2C([10*])=C1[11*].[1*]C1=C([2*])C([3*]C)=C2C([4*])=C([5*])C3=C4C2=C1CC1=C4C2=C(C3)C([7*])=C([8*])C([9*])=C2C([10*])=C1[11*].[1*]C1=C([2*])C([3*]C)=C2C([4*])=C([5*])C3=C4C2=C1CC1=C4C2=C(C3)C([7*])=C([8*])C([9*]C)=C2C([10*])=C1[11*] Chemical compound [1*]C1=C([2*])C([3*])=C2C([4*])=C([5*])C3=C4C2=C1CC1=C4C2=C(C3)C([7*])=C([8*])C([9*]C)=C2C([10*])=C1[11*].[1*]C1=C([2*])C([3*]C)=C2C([4*])=C([5*])C3=C4C2=C1CC1=C4C2=C(C3)C([7*])=C([8*])C([9*])=C2C([10*])=C1[11*].[1*]C1=C([2*])C([3*]C)=C2C([4*])=C([5*])C3=C4C2=C1CC1=C4C2=C(C3)C([7*])=C([8*])C([9*]C)=C2C([10*])=C1[11*] 0.000 description 7
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- 229910052763 palladium Inorganic materials 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
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- AMDQVKPUZIXQFC-UHFFFAOYSA-N dinaphthylene dioxide Chemical compound O1C(C2=C34)=CC=CC2=CC=C3OC2=CC=CC3=CC=C1C4=C32 AMDQVKPUZIXQFC-UHFFFAOYSA-N 0.000 description 4
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- 238000000354 decomposition reaction Methods 0.000 description 3
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- 238000010438 heat treatment Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000007733 ion plating Methods 0.000 description 3
- 238000005121 nitriding Methods 0.000 description 3
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 229910044991 metal oxide Inorganic materials 0.000 description 2
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
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- 239000011669 selenium Substances 0.000 description 2
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
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- 239000010936 titanium Substances 0.000 description 2
- BODYVHJTUHHINQ-UHFFFAOYSA-N (4-boronophenyl)boronic acid Chemical compound OB(O)C1=CC=C(B(O)O)C=C1 BODYVHJTUHHINQ-UHFFFAOYSA-N 0.000 description 1
- RZCPLOMUUCFPQA-UHFFFAOYSA-N (4-ethylphenyl)boronic acid Chemical compound CCC1=CC=C(B(O)O)C=C1 RZCPLOMUUCFPQA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LXPUQSHCYFARTL-UHFFFAOYSA-N C1=CC=C2C=C3C=C4C=C5C=CC=CC5=CC4=CC3=CC2=C1.C1=CC=C2C=C3C=C4C=CC=CC4=CC3=CC2=C1.C1=CC=C2C=C3C=CC=CC3=CC2=C1 Chemical compound C1=CC=C2C=C3C=C4C=C5C=CC=CC5=CC4=CC3=CC2=C1.C1=CC=C2C=C3C=C4C=CC=CC4=CC3=CC2=C1.C1=CC=C2C=C3C=CC=CC3=CC2=C1 LXPUQSHCYFARTL-UHFFFAOYSA-N 0.000 description 1
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 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 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052699 polonium Inorganic materials 0.000 description 1
- HZEBHPIOVYHPMT-UHFFFAOYSA-N polonium atom Chemical compound [Po] HZEBHPIOVYHPMT-UHFFFAOYSA-N 0.000 description 1
- 229920000090 poly(aryl ether) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000004306 triazinyl group Chemical group 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
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/06—Peri-condensed systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
Definitions
- the present application relates to an anthanthrene based compound and a semiconductor device including a semiconductor layer composed of such an anthanthrene based compound.
- a semiconductor layer can be coated and deposited at a low temperature as compared with a configuration including a semiconductor layer composed of an inorganic material. For that reason, such a semiconductor device is advantageous for realizing a large area and can be formed on a flexible substrate which is, however, low in heat resistance, such as plastics. Reduction in cost as well as multi-functionalization is also expected.
- organic semiconductor materials constituting a semiconductor layer for example, polyacene compounds such as anthracene, naphthacene and pentacene having the following structural formulae are being widely researched.
- the polyacene compound as a constituent unit has reaction active sites within a molecule thereof (specifically, for example, so far as pentacene is concerned, an electron density is high at the 6-position and the 12-position, and the 6-position and the 12-position are a reaction active site) and easily causes a decomposition reaction by oxygen, light, water, high temperature or the like, and its stability in the atmosphere is not satisfactory. Then, even in an oligo polyacene compound, so far as it has such a polyacene compound, it may be considered that it is difficult to establish stability of the molecule.
- an anthanthrene based compound having favorable stability in the atmosphere and a semiconductor device including a semiconductor layer composed of such an anthanthrene based compound.
- anthanthrene based compound represented by the following structural formula (1) (oligo dichalcogeno anthanthrene based compound).
- anthanthrene based compound represented by the following structural formula (2) (oligo dichalcogeno anthanthrene based compound).
- a semiconductor device including a substrate having thereon a gate electrode, a gate insulating layer, source/drain electrodes and a channel-forming region, wherein
- the channel-forming region is composed of the anthanthrene based compound (oligo dichalcogeno anthanthrene based compound) according to the foregoing first embodiment.
- a semiconductor device including a substrate having thereon a gate electrode, a gate insulating layer, source/drain electrodes and a channel-forming region, wherein
- the channel-forming region is composed of the anthanthrene based compound (oligo dichalcogeno anthanthrene based compound) according to the foregoing second embodiment.
- anthanthrene based compound according to the first embodiment or the anthanthrene based compound constituting the channel-forming region of the semiconductor device according to the first embodiment,
- X represents an element belonging to the Group 16
- n an integer of from 0 to 20;
- n an integer of from 1 to 9;
- a bonding position in the A segment to the B segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the B segment to the A segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the B segment to the C segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the C segment to the B segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position.
- the bonding position in the A segment to the B segment is not always required to be identical with the bonding position in the B segment to the C segment; and the bonding position in the B segment to the C segment is not always required to be identical with the bonding position in the C segment to the B segment.
- the B segments may be linearly bonded to each other as a kind, may be bonded to each other in a partially branched state, or may be cyclically bonded to each other as a kind.
- the C segments may be linearly bonded to each as a kind, may be bonded to each other in a partially branched state, or may be cyclically bonded to each other as a kind
- anthanthrene based compound according to the second embodiment or the anthanthrene based compound constituting the channel-forming region of the semiconductor device according to the second embodiment,
- X represents an element belonging to the Group 16
- each of [Y] and [Z] independently represents a functional group of one member selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, an arylalkyl group, an aromatic heterocyclic ring, a heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkylthio group, a cycloalkylthio group, an arylthio group, an alkoxycarbonyl group, an aryloxycarbonyl group, a sulfamoyl group, an acyl group, an acyloxy group, an amide group, a carbamoyl group, a ureido group, an sulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an amino group, a fluorinated hydrocarbon group, a
- n an integer of from 0 to 20;
- n an integer of from 1 to 9;
- a bonding position in the A segment to [Y] is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the B segment to [Y] is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the B segment to [Z] is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the C segment to [Z] is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position.
- the bonding position in the A segment to [Y] is not always required to be identical with the bonding position in the B segment to [Y]; and the bonding position in the B segment to [Z] is not always required to be identical with the bonding position in the C segment to [Z].
- a bonding position in [Y] to the A segment, a bonding position in [Y] to the B segment, a bonding position in [Z] to the B segment and a bonding position in [Z] to the C segment are not important.
- the B segments may be linearly bonded to each other as a kind, may be bonded to each other in a partially branched state, or may be cyclically bonded to each other as a kind.
- the C segments may be linearly bonded to each as a kind, may be bonded to each other in a partially branched state, or may be cyclically bonded to each other as a kind
- each of substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 and R 11 independently represents a substituent of one member selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, an arylalkyl group, an aromatic heterocyclic ring, a heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkylthio group, a cycloalkylthio group, an arylthio group, an alkoxycarbonyl group, an aryloxycarbonyl group, a sulfamoyl group, an acyl group, an acyloxy group, an amide group, a carbamoyl group,
- each of the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 and R 11 independently represents a substituent selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, an arylalkyl group, an aromatic heterocyclic ring and a halogen atom.
- examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group and a dodecyl group. It is not important whether the alkyl group is linear or branched.
- examples of the cycloalkyl group include a cyclopentyl group and a cyclohexyl group;
- examples of the alkenyl group include a vinyl group;
- examples of the alkynyl group include an ethynyl group;
- examples of the aryl group include a phenyl group and a naphthyl group;
- examples of the arylalkyl group include a methylaryl group, an ethylaryl group, an isopropylaryl group and an n-butylaryl group;
- examples of the aromatic heterocyclic ring include a pyridyl group, a thienyl group, a furyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, a quin
- a cyano group a nitro group, a hydroxyl group and a mercapto group.
- the silyl group include a trimethylsilyl group, a triisopropylsilyl group, a triphenylsilyl group and a phenyldiethylsilyl group.
- each of the above-exemplified substituents may be further substituted with any of the foregoing substituents.
- a plurality of these substituents may be bonded to each other to form a ring.
- a mode wherein X is an oxygen atom is much more preferable.
- a repeating unit (monomer unit) is stable in the atmosphere, and the repeating unit (monomer unit) has a wide ⁇ -system (having more aromatic rings). That is, each of the carbon atoms at the 6-position and the 12-position of the monomer unit in the anthanthrene based compound, etc. according to the embodiment is substituted with an element belonging to the Group 16, and therefore, the 6-position and the 12-position are not a reaction active site.
- the compound hardly causes a decomposition reaction by oxygen, light, water, high temperature or the like and is excellent in stability in the atmosphere. Also, larger overlapping of orbits is formed between adjacent molecules, and carrier mobility can be enhanced.
- the embodiments it is possible to provide a stable organic semiconductor material having high oxygen resistance, light fastness, heat resistance, water resistance and solvent resistance in the atmosphere and also having high carrier mobility. Therefore, by constituting a channel-forming region from the anthanthrene based compound, etc. according to the embodiment, the semiconductor device (organic transistor) according to the embodiment is able to display high carrier mobility and even after a thermal treatment at a high temperature in the atmosphere, is able to maintain high stability and high carrier mobility. Also, the anthanthrene based compound, etc. according to the embodiment has high stability, and therefore, it is possible to widen a width of a manufacturing process of a semiconductor device
- FIG. 1A and FIG. 1B are drawings showing synthesis schemes of anthanthrene based compounds of Example 1 and Example 2, respectively.
- FIG. 2 is a drawing showing a synthesis scheme of an anthanthrene based compound of Example 3.
- FIG. 3A is a schematic partial sectional view of a so-called bottom gate/top contact type field effect transistor; and FIG. 3B is a schematic partial sectional view of a so-called bottom gate/bottom contact type field effect transistor.
- FIG. 4A is a schematic partial sectional view of a so-called top gate/top contact type field effect transistor; and FIG. 4B is a schematic partial sectional view of a so-called top gate/bottom contact type field effect transistor.
- Anthanthrene based compound according to the first embodiment anthanthrene based compound according to the second embodiment; semiconductor device according to the first embodiment; semiconductor device according to the second embodiment; and explanation regarding the whole thereof.
- Example 4 Silicon devices according to the first embodiment and second embodiment and others.
- X represents an element belonging to the Group 16.
- the “element belonging to the Group 16” as referred to herein is a generic name of elements belonging to the Group 16 of the periodic table; and oxygen (O), sulfur (S), selenium (Se), tellurium (Te) and polonium (Po) are classified in this.
- This element is also called an oxygen group element or a chalcogen.
- each of the A segment, the B segment and the C segment per se is an organic semiconductor material obtained by substituting a dioxaanthanthrene based compound, specifically 6,12-dioxaanthanthrene (so-called peri-xanthenoxanthene, which is sometimes abbreviated as “PXX”) at from the 1-position to the 5-position and from the 7-position to the 11-position with any of the following substituents including a hydrogen atom.
- a dioxaanthanthrene based compound specifically 6,12-dioxaanthanthrene (so-called peri-xanthenoxanthene, which is sometimes abbreviated as “PXX”)
- semiconductor device is constituted of a bottom gate/bottom contact type field effect transistor (FET), such a bottom gate/bottom contact type FET includes
- such a bottom gate/top contact type FET includes
- such a top gate/bottom contact type FET includes
- such a top gate/top contact type FET includes
- the substrate can be constituted of a silicon oxide based material (for example, SiO X and spin-on glass (SOG)); silicon nitride (SiN Y ); aluminum oxide (Al 2 O 3 ); or a metal oxide high-dielectric constant insulating film.
- a silicon oxide based material for example, SiO X and spin-on glass (SOG)
- SiN Y silicon nitride
- Al 2 O 3 aluminum oxide
- the substrate may be formed on a support (or in an upper part of a support) which is properly selected among the following materials.
- examples of the support and/or a substrate other than the foregoing substrate include organic polymers such as polymethyl methacrylate (polymethacrylic acid methyl (PMMA)), polyvinyl alcohol (PVA), polyvinyl phenol (PVP), polyethersulfone (PES), polyimide, polycarbonate, polyethylene terephthalate (PET) and polyethylene naphthalate (PEN) (having a mode of a polymer material such as flexible plastic films, plastic sheets or plastic substrates constituted of a polymer material); and mica.
- PMMA polymethyl methacrylate
- PVA polyvinyl alcohol
- PVP polyvinyl phenol
- PES polyethersulfone
- PET polyethylene terephthalate
- PEN polyethylene naphthalate
- the semiconductor device can be built in or integrated into a display device or an electronic appliance having a curved shape.
- the substrate include various glass substrates, various glass substrates provided with an insulating film on the surface thereof, quartz substrates, quartz substrates provided with an insulating film on the surface thereof, silicon substrates provided with an insulating film on the surface thereof and metal substrates made of an alloy of every kind or a metal of every kind, such as stainless steel.
- a support having electrical insulating properties an appropriate material may be selected among the foregoing materials.
- the support include conductive substrates (for example, a substrate made of a metal (e.g., gold), a substrate made of highly oriented graphite, a stainless steel substrate, etc.).
- the semiconductor device may be provided on a support. Such a support can be made of any of the foregoing materials.
- Examples of the material constituting the gate electrode, source/drain electrodes and wirings include metals such as platinum (Pt), gold (Au), palladium (Pd), chromium (Cr), molybdenum (Mo), nickel (Ni), aluminum (Al), silver (Ag), tantalum (Ta), tungsten (W), copper (Cu), titanium (Ti), indium (In) and tin (Sn); an alloy containing such a metal element; conductive particles composed of such a metal; conductive particles composed of alloys containing such a metal; and conductive materials such as impurity-containing polysilicon.
- a laminated structure including layers each containing such an element may be employed.
- an organic material such as poly(3,4-ethylenedioxythiophene)/polystyrene sulfonic acid [PEDOT/PSS] can also be exemplified.
- the materials constituting the gate electrode, source/drain electrodes and wirings may be the same or different.
- a method for forming the gate electrode, source/drain electrodes and wiring varies depending upon the materials constituting them, examples thereof include a physical vapor deposition method (PVD method); various chemical vapor deposition methods (CVD methods) inclusive of an MOCVD method; a spin coating method; various printing methods such as a screen printing method, an inkjet printing method, an offset printing method, a reverse offset printing method, a gravure printing method and a microcontact method; various coating methods such as an air doctor coating method, a blade coating method, a rod coating method, a knife coating method, a squeeze coating method, a reverse roll coating method, a transfer roll coating method, a gravure coating method, a kiss coating method, a cast coating method, a spray coating method, a slit orifice coating method, a calender coating method and a dipping method; a stamping method; a lift-off method; a shadow mask method; plating methods such as an electrolytic plating method, an electroless plating method and a combination
- PVD methods include (a) various vacuum vapor deposition methods such as an electron beam heating method, a resistance heating method, a flash vapor deposition method and a method of heating a crucible; (b) a plasma vapor deposition method; (c) various sputtering methods such as a diode sputtering method, a direct current sputtering method, a direct current magnetron sputtering method, a radio frequency sputtering method, a magnetron sputtering method, an ion beam sputtering method and a bias sputtering method; and (d) various ion plating methods such as a direct current (DC) method, an RF method, a multi-cathode method, an activation reaction method, an electric field vapor deposition method, a radio frequency ion plating method and a reactive ion plating method.
- DC direct current
- examples of the material constituting the gate insulating layer include inorganic insulating materials such as silicon oxide based materials, silicon nitride (SiN Y ) and metal oxide high-dielectric constant insulating films; and organic insulating materials such as polymethyl methacrylate (PMMA), polyvinyl phenol (PVP) and polyvinyl alcohol (PVA). These materials may be used in combinations.
- inorganic insulating materials such as silicon oxide based materials, silicon nitride (SiN Y ) and metal oxide high-dielectric constant insulating films
- organic insulating materials such as polymethyl methacrylate (PMMA), polyvinyl phenol (PVP) and polyvinyl alcohol (PVA). These materials may be used in combinations.
- silicon oxide based material examples include silicon oxide (SiO X ), BPSG, PSG, BSG, AsSG, PbSG, silicon oxynitride (SiON), SOG (spin-on glass) and low-dielectric constant materials (for example, polyaryl ethers, cycloperfluorocarbon polymers, benzocyclobutene, cyclic fluorocarbon resins, polytetrafluoroethylene, fluoroaryl ethers, polyfluoroimide, amorphous carbon and organic SOG).
- silicon oxide SiO X
- BPSG silicon oxide
- PSG PSG
- BSG AsSG
- PbSG silicon oxynitride
- SOG spin-on glass
- low-dielectric constant materials for example, polyaryl ethers, cycloperfluorocarbon polymers, benzocyclobutene, cyclic fluorocarbon resins, polytetrafluoroethylene, fluoroaryl ethers, polyfluor
- the gate insulating layer can be formed by oxidizing or nitriding the surface of the gate electrode, or can be obtained by depositing an oxide film or a nitride film on the surface of the gate electrode.
- a method for oxidizing the surface of the gate electrode varies depending upon the material constituting the gate electrode, and examples thereof include an oxidation method using O 2 plasma and an anodic oxidation method.
- a method for nitriding the surface of the gate electrode varies depending upon the material constituting the gate electrode, and examples thereof include a nitriding method using N 2 plasma.
- a gate insulating layer can be formed in a self-assembling manner on the surface of the gate electrode by coating the surface of the gate electrode with an insulating molecule having a functional group capable of forming a chemical bond with the gate electrode, such as linear hydrocarbons whose one end is modified with a mercapto group, by a method such a dipping method.
- Examples of a method for forming the channel-forming region, or the channel-forming region and the channel-forming region extension include the foregoing various PVD methods; a spin coating method; the foregoing various printing methods; the foregoing various coating methods; a dipping method; a casting method; and a spraying method.
- additives for example, so-called doping materials such as n-type impurities and p-type impurities
- doping materials such as n-type impurities and p-type impurities
- the semiconductor device according to the embodiment is applied to and used for display devices or various electronic appliances, a monolithic integrated circuit in which a number of semiconductor devices are integrated on a support may be fabricated, or the individual semiconductor devices may be used upon being separated by cutting to produce discrete components. Also, the semiconductor device may be sealed with a resin. Specifically, the semiconductor device according to the embodiment can be used for liquid crystal display devices, organic electroluminescent light-emitting apparatuses, electronic papers, various sensors, RFIDs (radio frequency identification card) and the like.
- Example 1 is concerned with the anthanthrene based compound according to the first embodiment.
- the anthanthrene based compound of Example 1 is an anthanthrene based compound represented by the following structural formula (1) (oligo dichalcogeno anthanthrene based compound).
- Each of the A segment, the B segment and the C segment per se is an organic semiconductor material obtained by substituting a dioxaanthanthrene based compound, specifically 6,12-dioxaanthanthrene (so-called peri-xanthenoxanthene, “PXX”) at from the 1-position to the 5-position and from the 7-position to the 11-position with any of the foregoing substituents including a hydrogen atom.
- PXX represents an element belonging to the Group 16
- n represents an integer of from 0 to 20
- m represents an integer of from 1 to 9.
- a bonding position in the A segment to the B segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the B segment to the A segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the B segment to the C segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the C segment to the B segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position.
- Example 1 X is an oxygen (O) element; n is 0; and m is 1. Therefore, the B segment does not exist; and a different reading is given such that a bonding position in the A segment to the C segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position; and that a bonding position in the C segment to the A segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position.
- the bonding position in the A segment to the C segment is one site at the 3-position; and the bonding position in the C segment to the A segment is one site at the 10-position.
- each of the substituents R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 and R 11 is a hydrogen atom; and R 9 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an ethylphenyl group.
- each of the substituents R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 and R 11 is a hydrogen atom; and R 3 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an ethylphenyl group.
- the anthanthrene based compound of Example 1 is represented by the following structural formula (3). Also, a synthesis scheme of the anthanthrene based compound of Example 1 is shown in FIG. 1A . That is, equivalent amounts of 3,9-dibromo-peri-xanthenoxanthene and p-ethylphenyl boronic acid are subjected to the Suzuki-Miyaura cross-coupling reaction (see Miyaura, N. and Suzuki, A., J. Chem. Soc., Chem. Commun., 1979, 866; and Miyaura, N., Yamada, K.
- a repeating unit (monomer unit) is stable in the atmosphere. That is, since the carbon atoms at the 6-position and the 12-position of the monomer unit (a major skeleton thereof is constituted of MOO in Example 1 or each of Examples 2 to 3 as described later are substituted with an element belonging to the Group 16 (specifically, an oxygen element), the instant sites are no longer a reaction active site; and the compound hardly causes a decomposition reaction by oxygen, light, water, high temperature or the like and is excellent in stability in the atmosphere. Also, the repeating unit (monomer unit) has a wide ⁇ -system.
- the compound has more aromatic rings, and its ⁇ -electron conjugated region is widened. Accordingly, the anthanthrene based compound of Example 1 or each of Examples 2 to 3 as described later forms larger overlapping of orbits between adjacent molecules (a so-called ⁇ - ⁇ stack, etc.), and its carrier mobility can be enhanced. That is, according to Example 1 or Examples 2 to 3 as described later, it is possible to provide a stable organic semiconductor material having high oxygen resistance, light fastness, heat resistance, water resistance and solvent resistance in the atmosphere and also having high carrier mobility.
- the organic transistor is able to display high carrier mobility and even after a thermal treatment at a high temperature in the atmosphere, is able to maintain high stability and high carrier mobility.
- the anthanthrene based compound of Example 1 or each of the Examples 2 to 3 as described later has high stability, and therefore, it is possible to widen a width of a manufacturing process of a semiconductor device.
- Example 2 is a modification of Example 1. In Example 1, n was set to be 0, whereas in Example 2, n was set to be 1.
- a bonding position in the A segment to the B segment is one site at the 3-position; and a bonding position in the B segment to the A segment is one site at the 10-position.
- a bonding position in the B segment to the C segment is one site at the 3-position; and a bonding position in the C segment to the B segment is one site at the 10-position.
- each of the substituents R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 and R 11 is a hydrogen atom; and R 9 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an ethylphenyl group.
- each of the substituents R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 and R 11 is a hydrogen atom.
- each of the substituents R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 and R 11 is a hydrogen atom; and R 3 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an ethylphenyl group.
- the anthanthrene based compound of Example 2 is represented by the following structural formula (4).
- a synthesis scheme of the anthanthrene based compound of Example 2 is shown in FIG. 1B . That is, 3,9-dibromo-peri-xanthenoxanthene and 2 equivalents of the compound (b) are subjected to the Suzuki-Miyaura cross-coupling reaction in the presence of a palladium catalyst, whereby a compound represented by the structural formula (4) can be obtained.
- Example 3 is concerned with the anthanthrene based compound according to the second embodiment.
- the anthanthrene based compound of Example 3 is an anthanthrene based compound represented by the following structural formula (2) (oligo dichalcogeno anthanthrene based compound).
- X represents an element belonging to the Group 16
- n an integer of from 0 to 20;
- n an integer of from 1 to 9;
- each of [Y] and [Z] independently represents a functional group of one member selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, an arylalkyl group, an aromatic heterocyclic ring, a heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkylthio group, a cycloalkylthio group, an arylthio group, an alkoxycarbonyl group, an aryloxycarbonyl group, a sulfamoyl group, an acyl group, an acyloxy group, an amide group, a carbamoyl group, a ureido group, an sulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an amino group, a fluorinated hydrocarbon group, a
- a bonding position in the A segment to [Y] is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the B segment to [Y] is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the B segment to [Z] is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position;
- a bonding position in the C segment to [Z] is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position.
- Example 3 X is an oxygen (O) element; n is 0; and m is 1. Therefore, the B segment and [Y] do not exist; and a different reading is given such that a bonding position in the A segment to [Z] is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position. Specifically, the bonding position in the A segment to [Z] is one site at the 3-position; and the bonding position in the C segment to [Z] is one site at the 10-position.
- O oxygen
- each of the substituents R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 and R 11 is a hydrogen atom; and R 9 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an ethylphenyl group.
- each of the substituents R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 and R 11 is a hydrogen atom; and R 3 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an ethylphenyl group.
- [Z] is an aryl group, and specifically a phenyl group.
- the anthanthrene based compound of Example 3 is represented by the following structural formula (5).
- a synthesis scheme of the anthanthrene based compound of Example 3 is shown in FIG. 2 . That is, p-phenylenediboronic acid and 2 equivalents of the compound (a) are subjected to the Suzuki-Miyaura cross-coupling reaction in the presence of a palladium catalyst, whereby a compound represented by the structural formula (5) can be obtained.
- n can also be set to be 1.
- the bonding position in the A segment to [Y] is set to be one site at the 3-position
- the bonding position in the B segment to [Y] is set to be one site at the 10-position
- the bonding position in the B segment to [Z] is set to be one site at the 3-position
- the bonding position in the C segment to [Z] is set to be one site at the 10-position.
- each of the substituents R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 and R 11 is a hydrogen atom; and R 9 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an ethylphenyl group. Also, in the B segment, each of the substituents R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 and R 11 is a hydrogen atom.
- each of the substituents R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 and R 11 is a hydrogen atom; and R 3 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an ethylphenyl group.
- R 3 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an ethylphenyl group.
- [Y] is an aryl group, and specifically a phenyl group.
- [Z] is an alkyl group, and specifically an ethyl group.
- Example 4 is concerned with each of the semiconductor devices according to the first embodiment and second embodiment.
- the semiconductor device of Example 4 (specifically, a field effect transistor (FET)) includes a substrate having thereon a gate electrode, a gate insulating layer, source/drain electrodes and a channel-forming region, wherein the channel-forming region is composed of the anthanthrene based compound represented by the foregoing structural formula (1).
- the semiconductor device of Example 4 includes a substrate having thereon a gate electrode, a gate insulating layer, source/drain electrodes and a channel-forming region, wherein the channel-forming region is composed of the anthanthrene based compound represented by the foregoing structural formula (2).
- the semiconductor device of Example 4 is a so-called bottom gate/top contact type FET (more specifically, TFT), including
- the substrates 10 , 11 are constituted of a substrate 10 composed of a glass substrate and an insulating film 11 formed on the surface thereof and made of SiO 2 ; each of the gate electrode 12 and the source/drain electrodes 15 is composed of a metal thin film; and the gate insulating layer 13 is made of SiO 2 .
- each of the channel-forming region 14 and the channel-forming region extension 14 A is constituted of any one of the anthanthrene based compounds described in Examples 1 to 3.
- each of the gate electrode 12 and the gate insulating layer 13 is formed on the insulating film 11 .
- TFT bottom gate/top contact type FET
- the gate electrode 12 is formed on the substrate (the glass substrate 10 in which the insulating film 11 made of SiO 2 is formed on the surface thereof). Specifically, a resist layer (not shown) in which a portion where the gate electrode 12 is to be formed is removed is formed on the insulating film 11 on the basis of a lithography technology. Thereafter, a chromium (Cr) layer (not shown) as a contact layer and a gold (Au) layer as the gate electrode 12 are deposited in success over the whole surface by a vacuum vapor deposition method, and the resist layer is then removed. The gate electrode 12 can be thus obtained on the basis of a so-called lift-off method.
- the gate insulating layer 13 is formed on the substrate (insulating film 11 ) including the gate electrode 12 .
- the gate insulating layer 13 made of SiO 2 is formed on the gate electrode 12 and the insulating film 11 on the basis of a sputtering method.
- a discharge part (not shown) of the gate electrode 12 can be formed without adopting a photolithography process.
- the channel-forming region 14 and the channel-forming region extension 14 A are formed on the gate insulating layer 13 .
- any one of the anthanthrene based compounds described in the foregoing Examples 1 to 3 is deposited on the basis of a vacuum vapor deposition method.
- the source/drain electrodes 15 are formed on the channel-forming region extension 14 A so as to interpose the channel-forming region 14 therebetween. Specifically, a chromium (Cr) layer (not shown) as a contact layer and gold (Au) layers as the source/drain electrodes 15 are formed in success over the whole surface on the basis of a vacuum vapor deposition method. A structure shown in FIG. 3A can be thus obtained.
- the source/drain electrodes 15 by covering a part of the channel-forming region extension 14 A by a hard mask, the source/drain electrodes 15 can be formed without adopting a photolithography process.
- an insulating layer (not shown) which is a passivation film is formed over the whole surface; an opening is formed on the insulating layer in an upper part of the source/drain electrodes 15 ; a wiring material layer is formed over the whole surface including the inside of the opening; and the wiring material layer is then subjected to patterning.
- TFT bottom gate/top contact type FET
- FET is not limited to the so-called bottom gate/top contact type shown in FIG. 3A , but besides, FET can also be formed in a so-called bottom gate/bottom contact type, a so-called top gate/top contact type or a so-called top gate/bottom contact type.
- a so-called bottom gate/bottom contact type FET (more specifically, TFT), a schematic partial sectional view of which is shown in FIG. 3B , includes
- the gate electrode 12 is formed on the substrate (insulating film 11 ); and thereafter, similar to the Step 510 A, the gate insulating layer 13 is formed on the gate electrode 12 and the insulating film 11 .
- the source/drain electrodes 15 composed of a gold (Au) layer are formed on the gate insulating layer 13 .
- a resist layer in which a portion where the source/drain electrodes 15 are to be formed is removed is formed on the basis of a lithography technology.
- a chromium (Cr) layer (not shown) as a contact layer and a gold (Au) layer as the source/drain electrodes 15 are deposited on the resist layer and the gate insulating layer 13 in success by a vacuum vapor deposition method, and thereafter, the resist layer is removed.
- the source/drain electrodes 15 can be thus obtained on the basis of a so-called lift-off method.
- the channel-forming region 14 is formed on a portion of the gate insulating layer 13 located between the source/drain electrodes 15 on the basis of the same manner as in the Step 520 A.
- a structure shown in FIG. 3B can be thus obtained.
- top gate/top contact type FET (more specifically, TFT), a schematic partial sectional view of which is shown in FIG. 4A , includes
- top gate/top contact type TFT An outline of a manufacturing method of the top gate/top contact type TFT is hereunder described.
- the channel-forming region 14 and the channel-forming region extension 14 A are formed on the substrate (the glass substrate 10 in which the insulating film 11 made of SiO 2 is formed on the surface thereof) on the basis of the same method as in the Step 520 A.
- the source/drain electrodes 15 are formed on the channel-forming region extension 14 A so as to interpose the channel-forming region 14 therebetween. Specifically, a chromium (Cr) layer (not shown) as a contact layer and gold (Au) layers as the source/drain electrodes 15 are formed in success over the whole surface on the basis of a vacuum vapor deposition method. During depositing the source/drain electrodes 15 , by covering a part of the channel-forming region extension 14 A by a hard mask, the source/drain electrodes 15 can be formed without adopting a photolithography process.
- Cr chromium
- Au gold
- the gate insulating layer 13 is formed on the source/drain electrodes 15 and the channel-forming region 14 . Specifically, by depositing PVA over the whole surface by a spin coating method, the gate insulating layer 13 can be obtained.
- the gate electrode 12 is formed on the gate insulating layer 13 .
- a chromium (Cr) layer (not shown) as a contact layer and a gold (Au) layer as the gate electrode 12 are deposited in success over the whole surface on the basis of a vacuum vapor deposition method.
- a structure shown in FIG. 4A can be thus obtained.
- the gate electrode 12 can be formed without adopting a photolithography process.
- the top gate/top contact type FET (TFT) can be obtained.
- top gate/bottom contact type FET (more specifically, TFT), a schematic partial sectional view of which is shown in FIG. 4B , includes
- the source/drain electrodes 15 are formed on the substrate (the glass substrate 10 in which the insulating film 11 made of SiO 2 is formed on the surface thereof). Specifically, a chromium (Cr) layer (not shown) as a contact layer and gold (Au) layers as the source/drain electrodes 15 are formed on the basis of a vacuum vapor deposition method. During depositing the source/drain electrodes 15 , by covering a part of the substrate (insulating film 11 ) by a hard mask, the source/drain electrodes 15 can be formed without adopting a photolithography process.
- a chromium (Cr) layer not shown
- Au gold
- the channel-forming region 14 is formed on the substrate (insulating film 11 ) located between the source/drain electrodes 15 on the basis of the same manner as in the Step 520 A. Actually, a channel-forming region extension 14 A is formed on the source/drain electrodes 15 .
- the gate insulating layer 13 is formed on the source/drain electrodes 15 and the channel-forming region 14 (actually, on the channel-forming region 14 and the channel-forming region extension 14 A) in the same manner as in the Step 520 C.
- the gate electrode 12 is formed on the gate insulating layer 13 in the same manner as in the Step 530 C.
- a structure shown in FIG. 4B can be thus obtained.
- the top gate/bottom contact type FET (TFT) can be obtained.
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US20130187145A1 (en) * | 2010-06-25 | 2013-07-25 | Sumitomo Chemical Company Limited | Organic light-emitting composition comprising anthranthene derivates and device and method using the same |
US20130277729A1 (en) * | 2012-04-20 | 2013-10-24 | Palo Alto Research Center Incorporated | Floating gate transistor memory with an organic semiconductor interlayer |
US20140014942A1 (en) * | 2012-07-12 | 2014-01-16 | Polymer Vision B.V. | Thin-film transistor, electronic circuit, display and method of manufacturing the same |
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US8399288B2 (en) * | 2010-08-02 | 2013-03-19 | Sony Corporation | Semiconductor device, method of manufacturing the same, and method of forming multilayer semiconductor thin film |
JP5807738B2 (ja) * | 2011-03-30 | 2015-11-10 | ソニー株式会社 | 有機トランジスタの製造方法、有機トランジスタ、半導体装置の製造方法、半導体装置および電子機器 |
JP6040518B2 (ja) * | 2011-08-25 | 2016-12-07 | ソニー株式会社 | 電子機器および半導体基板 |
JP5899010B2 (ja) * | 2012-03-06 | 2016-04-06 | 株式会社ダイセル | アンタントレン系化合物およびその製造方法 |
WO2014106938A1 (ja) * | 2013-01-07 | 2014-07-10 | 富士電機株式会社 | 透明有機薄膜トランジスタ及びその製造方法 |
US8889475B1 (en) | 2013-05-30 | 2014-11-18 | International Business Machines Corporation | Self-aligned bottom-gated graphene devices |
CN111004249B (zh) * | 2019-11-28 | 2021-08-20 | 北京燕化集联光电技术有限公司 | 一种oled材料及其应用 |
CN110903296B (zh) * | 2019-11-28 | 2021-08-20 | 北京燕化集联光电技术有限公司 | 一种oled材料及其在器件中的应用 |
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US20130187145A1 (en) * | 2010-06-25 | 2013-07-25 | Sumitomo Chemical Company Limited | Organic light-emitting composition comprising anthranthene derivates and device and method using the same |
US9142782B2 (en) | 2010-06-25 | 2015-09-22 | Cambridge Display Technology, Ltd. | Organic light-emitting material, device and method |
US9773981B2 (en) | 2010-06-25 | 2017-09-26 | Cambridge Display Technology, Ltd. | Organic light-emitting device and method |
US9812647B2 (en) | 2010-06-25 | 2017-11-07 | Cambridge Display Technology, Ltd. | Organic light-emitting device and method |
US20130277729A1 (en) * | 2012-04-20 | 2013-10-24 | Palo Alto Research Center Incorporated | Floating gate transistor memory with an organic semiconductor interlayer |
US20140014942A1 (en) * | 2012-07-12 | 2014-01-16 | Polymer Vision B.V. | Thin-film transistor, electronic circuit, display and method of manufacturing the same |
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