JP5812355B2 - 有機半導体 - Google Patents
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- JP5812355B2 JP5812355B2 JP2012527375A JP2012527375A JP5812355B2 JP 5812355 B2 JP5812355 B2 JP 5812355B2 JP 2012527375 A JP2012527375 A JP 2012527375A JP 2012527375 A JP2012527375 A JP 2012527375A JP 5812355 B2 JP5812355 B2 JP 5812355B2
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- 239000004065 semiconductor Substances 0.000 title claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 33
- 239000000463 material Substances 0.000 description 26
- 239000000758 substrate Substances 0.000 description 17
- 239000010409 thin film Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 11
- 239000003989 dielectric material Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 8
- 238000000151 deposition Methods 0.000 description 7
- 230000003381 solubilizing effect Effects 0.000 description 6
- 238000007641 inkjet printing Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000011241 protective layer Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000005669 field effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 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
- 238000004528 spin coating Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004630 atomic force microscopy Methods 0.000 description 2
- 125000005620 boronic acid group Chemical class 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) 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
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C12C3(*)*1)(c1c2cc(C(C)(*C24*)C5=C2C=C*5)c4c1)C(*)=C3C(C=C)=C(*)C=CI[Al] Chemical compound CC(C12C3(*)*1)(c1c2cc(C(C)(*C24*)C5=C2C=C*5)c4c1)C(*)=C3C(C=C)=C(*)C=CI[Al] 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 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
- 229910004541 SiN Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- WXRSDHICEYICMV-UHFFFAOYSA-N diethyl 2,5-dibromobenzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC(Br)=C(C(=O)OCC)C=C1Br WXRSDHICEYICMV-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UHPJWJRERDJHOJ-UHFFFAOYSA-N ethene;naphthalene-1-carboxylic acid Chemical compound C=C.C1=CC=C2C(C(=O)O)=CC=CC2=C1 UHPJWJRERDJHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 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
- 230000002452 interceptive effect Effects 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
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 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
- PYHOFAHZHOBVGV-UHFFFAOYSA-N triazane Chemical compound NNN PYHOFAHZHOBVGV-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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Classifications
-
- 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
- C07D495/04—Ortho-condensed systems
-
- 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
- C07D495/12—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 three hetero rings
- C07D495/14—Ortho-condensed systems
-
- 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
- C07D495/22—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- 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]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Thin Film Transistor (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Metal-Oxide And Bipolar Metal-Oxide Semiconductor Integrated Circuits (AREA)
Description
X1およびX2は独立に、S、O、NR5またはSiR6R7を含み、R5〜R7は独立に、C1〜C5の分岐、直鎖、または環状のアルキル鎖を含み、
Ar1は、複素環式芳香環を含み、nは、1〜4の間の整数である)
を含む。
の群から選択される構造を含むことが好ましい。
Claims (6)
- 下記一般式(I)または(II)で表される構造を含む半導体化合物であって:
X1およびX2は独立に、SまたはOから選択され、
Ar1は、S、O、NR5またはSiR6R7の群から選択される少なくとも1つのヘテロ原子を含む複素環式芳香環であり、ここで、R 5 〜R 7 は独立に、C 1 〜C 5 の分岐、直鎖または環状のアルキル鎖から選択され、
Ar 2 は、同素環式または複素環式芳香環であり、
nは、1〜4の間の整数である。)
Ar1および/または存在する場合、Ar2と連続して縮合された1つまたは複数のさらなる芳香族基を含み、
前記半導体化合物の末端芳香族が、1つ以上の反応基または重合可能基である置換基Tで置換されており、ここで、置換基Tはそれぞれ独立して、ハロゲン、ボロン酸、ボロン酸のエステル、アルキレン基およびスタンニル基から選ばれる、前記半導体化合物。 - Ar2が、S、O、NR5またはSiR6R7の群から選択される少なくとも1つのヘテロ原子を含む複素環式芳香環である、請求項1に記載の半導体化合物。
- 前記さらなる芳香族基の1つ、いくつか、またはすべてが、S、O、NR5、またはSiR6R7の群から選択される少なくとも1つのヘテロ原子を含有する複素環基を含む、請求項1に記載の半導体化合物。
- R1〜R4が同じであるか、または異なっており、独立に、2〜12個の間の炭素原子を有する、置換された、または置換されていない、直鎖、分岐、または環状のアルキル鎖を含む、請求項1〜4のいずれか一項に記載の半導体化合物。
- R1〜R4が同じであるか、または異なっており、独立に、2〜6個の間の炭素原子を有する、置換された、または置換されていない、直鎖、分岐、または環状のアルキル鎖を含む、請求項5に記載の半導体化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0913628.4 | 2009-08-05 | ||
GB0913628.4A GB2472413B (en) | 2009-08-05 | 2009-08-05 | Organic semiconductors |
PCT/GB2010/001485 WO2012017184A1 (en) | 2009-08-05 | 2010-08-05 | Organic semiconductors |
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JP2015138071A Division JP6053880B2 (ja) | 2009-08-05 | 2015-07-09 | 有機半導体 |
Publications (2)
Publication Number | Publication Date |
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JP2013501076A JP2013501076A (ja) | 2013-01-10 |
JP5812355B2 true JP5812355B2 (ja) | 2015-11-11 |
Family
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JP2012527375A Active JP5812355B2 (ja) | 2009-08-05 | 2010-08-05 | 有機半導体 |
JP2015138071A Active JP6053880B2 (ja) | 2009-08-05 | 2015-07-09 | 有機半導体 |
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JP2015138071A Active JP6053880B2 (ja) | 2009-08-05 | 2015-07-09 | 有機半導体 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8853679B2 (ja) |
EP (4) | EP2462146A1 (ja) |
JP (2) | JP5812355B2 (ja) |
KR (1) | KR101787121B1 (ja) |
CN (1) | CN102482291A (ja) |
GB (1) | GB2472413B (ja) |
WO (1) | WO2012017184A1 (ja) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9761805B2 (en) | 2011-07-19 | 2017-09-12 | Merck Patent Gmbh | Organic semiconductors |
CN104024263A (zh) * | 2011-10-20 | 2014-09-03 | 默克专利有限公司 | 有机半导体 |
GB2514508A (en) * | 2012-02-16 | 2014-11-26 | Merck Patent Gmbh | Organic semiconducting polymers |
US9673397B2 (en) | 2012-04-25 | 2017-06-06 | Merck Patent Gmbh | Conjugated polymers |
EP2904067A1 (en) * | 2012-10-05 | 2015-08-12 | Merck Patent GmbH | Organic semiconductors |
WO2014086457A1 (en) | 2012-12-07 | 2014-06-12 | Merck Patent Gmbh | Polymer comprising a naphthalene group and its use in organic electronic devices |
WO2014094954A1 (en) * | 2012-12-18 | 2014-06-26 | Merck Patent Gmbh | Indenophenanthrene based compounds |
KR102173046B1 (ko) * | 2013-12-06 | 2020-11-03 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
JP6252264B2 (ja) * | 2014-03-12 | 2017-12-27 | 住友化学株式会社 | 高分子化合物およびそれを用いた有機半導体素子 |
CN105315298B (zh) * | 2014-08-04 | 2017-10-10 | 中国科学院化学研究所 | 基于七并稠环单元的a‑d‑a共轭分子及其制备方法和应用 |
CN104557972B (zh) * | 2015-01-20 | 2017-02-22 | 武汉理工大学 | 双(噻吩并[3,2‑b]噻吩)并芴单体、共轭聚合物及其应用 |
WO2017097924A1 (en) * | 2015-12-10 | 2017-06-15 | Basf Se | Naphthoindacenodithiophenes and polymers |
CN106905344B (zh) * | 2015-12-23 | 2018-11-30 | 北京大学 | 基于七并稠环单元的共轭大分子及其制备方法和在太阳能电池中的应用 |
CN108603012A (zh) | 2016-01-29 | 2018-09-28 | 住友化学株式会社 | 组合物及使用其的有机薄膜晶体管 |
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GB0913628D0 (en) | 2009-09-16 |
JP2015227461A (ja) | 2015-12-17 |
US8853679B2 (en) | 2014-10-07 |
KR101787121B1 (ko) | 2017-10-18 |
JP2013501076A (ja) | 2013-01-10 |
JP6053880B2 (ja) | 2016-12-27 |
KR20120069675A (ko) | 2012-06-28 |
EP2462146A1 (en) | 2012-06-13 |
EP3141551A1 (en) | 2017-03-15 |
GB2472413A (en) | 2011-02-09 |
EP3447057A1 (en) | 2019-02-27 |
EP3524610A1 (en) | 2019-08-14 |
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