JP2013529189A - 有機半導体 - Google Patents
有機半導体 Download PDFInfo
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- JP2013529189A JP2013529189A JP2013505530A JP2013505530A JP2013529189A JP 2013529189 A JP2013529189 A JP 2013529189A JP 2013505530 A JP2013505530 A JP 2013505530A JP 2013505530 A JP2013505530 A JP 2013505530A JP 2013529189 A JP2013529189 A JP 2013529189A
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 58
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 12
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 10
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 150000001408 amides Chemical class 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 239000000758 substrate Substances 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 14
- 230000003381 solubilizing effect Effects 0.000 claims description 8
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 238000010276 construction Methods 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 12
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- 239000010410 layer Substances 0.000 description 41
- 239000000463 material Substances 0.000 description 29
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- 239000010409 thin film Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003989 dielectric material Substances 0.000 description 11
- 238000000151 deposition Methods 0.000 description 8
- 0 CCC(C(C(CI)=C)=C12)=C(*C(CI)=ICCC(**)I)C1=*(C=C(C)C(I)=C1C(I(CCC(CCCCCI)*C)=C)=C3*)C1=C3C2=CC Chemical compound CCC(C(C(CI)=C)=C12)=C(*C(CI)=ICCC(**)I)C1=*(C=C(C)C(I)=C1C(I(CCC(CCCCCI)*C)=C)=C3*)C1=C3C2=CC 0.000 description 7
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002094 self assembled monolayer Substances 0.000 description 3
- 239000013545 self-assembled monolayer Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000004630 atomic force microscopy Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000412 polyarylene Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 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
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- HHOPYTCVCFFXSQ-UHFFFAOYSA-N CCC(C(C)(C)N)F Chemical compound CCC(C(C)(C)N)F HHOPYTCVCFFXSQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- FAERCJFAEOYPRX-UHFFFAOYSA-M [Br-].CCCCCCCCC1=CC=C([Mg+])C=C1 Chemical compound [Br-].CCCCCCCCC1=CC=C([Mg+])C=C1 FAERCJFAEOYPRX-UHFFFAOYSA-M 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
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- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
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- -1 diboronic acid ester Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- CDKDZKXSXLNROY-UHFFFAOYSA-N octylbenzene Chemical compound CCCCCCCCC1=CC=CC=C1 CDKDZKXSXLNROY-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 1
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D343/00—Heterocyclic compounds containing rings having sulfur and selenium or sulfur and tellurium atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/06—Peri-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/78—Other dyes in which the anthracene nucleus is condensed with one or more carbocyclic rings
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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
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
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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
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
- C09B69/102—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye containing a perylene dye
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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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract
【化1】
(式中、X1およびX2は独立して、S、Se、SiR1R2、O、CR3R4、C2R5R6、N、NR7であり、R1からR7は、水素、直鎖、分枝もしくは環式アルキル、アルケニルもしくはアルキニル基、アルコキシ、アリール、シリルまたはアミノを独立して含み;Ar1からAr4はそれぞれ任意であり、存在する場合、アリールまたはヘテロアリール基を独立して含み;およびY1からY4は、水素、反応性基、置換されていてもよい直鎖、分枝もしくは環式アルキル、アルコキシ、アルケニル、アルキニル、アミドまたはアミノ基、置換されていてもよいアリールまたはヘテロアリールを独立して含み、Y1からY4の少なくとも1つが水素を含まない。)を含む半導体化合物ならびにこれに関連する方法およびデバイス。
【選択図】図2
Description
式中、X1およびX2は独立して、S、Se、SiR1R2、O、CR3R4、C2R5R6、N、NR7であり、R1からR7は、水素、好ましくは1から20個の炭素原子を有する直鎖、分枝もしくは環式アルキル、アルケニルもしくはアルキニル基、アルコキシ、アリール、シリルまたはアミノを独立して含み;
Ar1からAr4はそれぞれ任意であり、存在する場合、アリールまたはヘテロアリール基を独立して含み;
およびY1からY4は、水素、反応性基、好ましくは1から20個の炭素原子を有する、置換されていてもよい直鎖、分枝もしくは環式アルキル、アルコキシ、アルケニル、アルキニル、アミドまたはアミノ基、置換されていてもよいアリールまたはヘテロアリールを独立して含み、Y1からY4の少なくとも1つは水素を含まない。
式中、nは2から10,000の間の整数であり;
X1およびX2は独立して、S、Se、SiR1R2、O、CR3R4、C2R5R6、N、NR7であり、R1からR7は、水素、好ましくは1から20個の炭素を有する直鎖、分枝もしくは環式アルキル、アルケニルもしくはアルキニル基、アルコキシ、アリール、シリルまたはアミノを独立して含み;
Ar1からAr4はそれぞれ任意であり、存在する場合、アリールまたはヘテロアリール基を独立して含み;
およびY1からY4は、水素、反応性基、好ましくは1から20個の炭素原子を有する、置換されていてもよい直鎖、分枝もしくは環式アルキル、アルコキシ、アルケニル、アルキニル、アミドまたはアミノ基を、置換されていてもよい(optionally substituted)アリールまたはヘテロアリールを独立して含み、Y1からY4の少なくとも1つは水素を含まない。
中間体1
窒素下の1,5−ジクロロアントラキノン(6.8g、24.6mmol)の無水トルエン(100ml)懸濁液に、4−オクチルフェニルマグネシウムブロミド溶液[無水THF(60ml)中の4−オクチルベンゼン(20.9g、74.3mmol)および削り状マグネシウム(2.14g、89.2mmol)より調製]を滴加した。
Claims (14)
- 構造:
Ar1からAr4はそれぞれ任意であり、存在する場合、アリールまたはヘテロアリール基を独立して含み;
およびY1からY4は、水素、反応性基、置換されていてもよい直鎖、分枝もしくは環式アルキル、アルコキシ、アルケニル、アルキニル、アミドまたはアミノ基、置換されていてもよいアリールまたはヘテロアリールを独立して含み、Y1からY4の少なくとも1つが水素を含まない。)
を含む半導体化合物。 - 構造:
式中、X1およびX2は独立して、S、Se、SiR1R2、O、CR3R4、C2R5R6、N、NR7であり、R1からR7は、水素、直鎖、分枝もしくは環式アルキル、アルケニルもしくはアルキニル基、アルコキシ、アリール、シリルまたはアミノを独立して含み;
Ar1からAr4はそれぞれ任意であり、存在する場合、アリールまたはヘテロアリール基を独立して含み;
およびY1からY4は、水素、反応性基、置換されていてもよい直鎖、分枝もしくは環式アルキル、アルコキシ、アルケニル、アルキニル、アミドまたはアミノ基、置換されていてもよいアリールまたはヘテロアリールを独立して含み、Y1からY4の少なくとも1つが水素を含まない。)
を含む半導体化合物。 - 該化合物がポリマーまたはコポリマーである、請求項2に記載の半導体化合物。
- nが2から10の間の整数である、請求項2に記載の半導体化合物。
- Ar1からAr4が基:S、O、Si、N、Seより選択されるヘテロ原子を有する複素環式基を独立して含む、請求項1から4のいずれかに記載の半導体化合物。
- Y1からY4の少なくとも1つが可溶化基を含む、請求項1から5のいずれかに記載の半導体化合物。
- Y1からY4の可溶化基が、置換されていてもよい直鎖、分枝もしくは環式アルキル、アルコキシ、アルケニル、アルキニル、アミドまたはアミノ基を独立して含む、請求項6に記載の半導体化合物。
- 該半導体化合物が2個以上の反応性基または重合性基を含む、請求項1から7のいずれかに記載の半導体化合物。
- Y1およびY3またはY2およびY4は反応性基または重合性基を含む、請求項8に記載の半導体化合物。
- 該反応性基または重合性基がハロゲン、ボロン酸、ジボロン酸、ボロン酸およびジボロン酸のエステル、アルキレン基またはスタンニル基を独立して含む、請求項8または9に記載の半導体化合物。
- 請求項1から11のいずれかに記載の化合物を含む半導体部分を含む電子デバイス。
- 該基板上に半導体部分を形成するために基板表面に塗布する溶液であって、該溶液が請求項1から12のいずれかに記載の化合物を含む溶液。
- 請求項13に記載の溶液を基板に塗布することを含む電子デバイスを製造する方法。
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GB1006832A GB2479793A (en) | 2010-04-23 | 2010-04-23 | Organic semiconductor compounds and devices |
GB1006832.8 | 2010-04-23 | ||
PCT/GB2011/000613 WO2011131936A1 (en) | 2010-04-23 | 2011-04-20 | Organic semiconductors |
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JP2012234873A (ja) * | 2011-04-28 | 2012-11-29 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置および照明装置 |
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US20130161602A1 (en) * | 2010-06-24 | 2013-06-27 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Process for modifying electrodes in an organic electronic device |
CN103242360B (zh) * | 2013-05-16 | 2016-02-24 | 中国科学院化学研究所 | 一种线形可溶性含硫原子的并五苯衍生物及其制备方法与应用 |
US9985222B2 (en) * | 2014-06-23 | 2018-05-29 | Samsung Electronics Co., Ltd. | Organic compound, and organic thin film and electronic device |
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GB2479793A (en) | 2011-10-26 |
WO2011131936A1 (en) | 2011-10-27 |
US20130102792A1 (en) | 2013-04-25 |
CN102844903B (zh) | 2016-06-22 |
EP2564439A1 (en) | 2013-03-06 |
US8946448B2 (en) | 2015-02-03 |
CN102844903A (zh) | 2012-12-26 |
GB201006832D0 (en) | 2010-06-09 |
KR20130094720A (ko) | 2013-08-26 |
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