CA2729334A1 - High performance solution processable seminconductor based on dithieno [2,3-d:2',3'-d']benzo[1,2-b:4,5-b'] dithiophene - Google Patents
High performance solution processable seminconductor based on dithieno [2,3-d:2',3'-d']benzo[1,2-b:4,5-b'] dithiophene Download PDFInfo
- Publication number
- CA2729334A1 CA2729334A1 CA2729334A CA2729334A CA2729334A1 CA 2729334 A1 CA2729334 A1 CA 2729334A1 CA 2729334 A CA2729334 A CA 2729334A CA 2729334 A CA2729334 A CA 2729334A CA 2729334 A1 CA2729334 A1 CA 2729334A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- alkyl
- aryl
- dithienobenzodithiophenes
- independently selected
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- JFYIISXNMRMQNF-UHFFFAOYSA-N dithieno[2,3-d:2',3'-d']benzo[1,2-b:4,5-b']dithiophene Chemical compound S1C2=CC(C=3SC=CC=3S3)=C3C=C2C2=C1C=CS2 JFYIISXNMRMQNF-UHFFFAOYSA-N 0.000 title description 13
- 239000004065 semiconductor Substances 0.000 claims abstract description 50
- 239000000463 material Substances 0.000 claims abstract description 28
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 23
- 239000010409 thin film Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 230000003287 optical effect Effects 0.000 claims abstract description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims abstract description 9
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims abstract description 5
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 3
- 239000007772 electrode material Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 28
- 239000000758 substrate Substances 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 17
- 238000007639 printing Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 238000005266 casting Methods 0.000 claims description 13
- 238000000151 deposition Methods 0.000 claims description 10
- 239000002131 composite material Substances 0.000 claims description 9
- 230000005669 field effect Effects 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000004528 spin coating Methods 0.000 claims description 7
- 238000003618 dip coating Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003106 haloaryl group Chemical group 0.000 claims description 4
- 229910003828 SiH3 Inorganic materials 0.000 claims description 2
- -1 poly(3-hexyl) Polymers 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 230000037230 mobility Effects 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052681 coesite Inorganic materials 0.000 description 12
- 229910052906 cristobalite Inorganic materials 0.000 description 12
- 229910052682 stishovite Inorganic materials 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 229910052905 tridymite Inorganic materials 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002800 charge carrier Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 239000010931 gold Substances 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 239000003990 capacitor Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- HSYMNOCSKWURAC-UHFFFAOYSA-N 2-[2,5-bis(methylsulfinyl)-4-(5-pentylthiophen-2-yl)phenyl]-5-pentylthiophene Chemical compound S1C(CCCCC)=CC=C1C1=CC(S(C)=O)=C(C=2SC(CCCCC)=CC=2)C=C1S(C)=O HSYMNOCSKWURAC-UHFFFAOYSA-N 0.000 description 4
- WTZQNHGJVLMBNT-UHFFFAOYSA-N 2-[2,5-bis(methylsulfinyl)-4-(5-propylthiophen-2-yl)phenyl]-5-propylthiophene Chemical compound S1C(CCC)=CC=C1C1=CC(S(C)=O)=C(C=2SC(CCC)=CC=2)C=C1S(C)=O WTZQNHGJVLMBNT-UHFFFAOYSA-N 0.000 description 4
- CTUKYEVLWCKVMP-UHFFFAOYSA-N 2-hexyl-5-[4-(5-hexylthiophen-2-yl)-2,5-bis(methylsulfinyl)phenyl]thiophene Chemical compound S1C(CCCCCC)=CC=C1C1=CC(S(C)=O)=C(C=2SC(CCCCCC)=CC=2)C=C1S(C)=O CTUKYEVLWCKVMP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000002508 contact lithography Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- ZJZMTFNSMGTRBF-UHFFFAOYSA-N (5-hexylthiophen-2-yl)-trimethylstannane Chemical compound CCCCCCC1=CC=C([Sn](C)(C)C)S1 ZJZMTFNSMGTRBF-UHFFFAOYSA-N 0.000 description 3
- IGGOSWVQBAXYSR-UHFFFAOYSA-N 1,4-dibromo-2,5-bis(methylsulfinyl)benzene Chemical compound CS(=O)C1=CC(Br)=C(S(C)=O)C=C1Br IGGOSWVQBAXYSR-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UVAMFBJPMUMURT-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenethiol Chemical compound FC1=C(F)C(F)=C(S)C(F)=C1F UVAMFBJPMUMURT-UHFFFAOYSA-N 0.000 description 3
- QZVHYFUVMQIGGM-UHFFFAOYSA-N 2-Hexylthiophene Chemical compound CCCCCCC1=CC=CS1 QZVHYFUVMQIGGM-UHFFFAOYSA-N 0.000 description 3
- VHOQONMRVDSCNI-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-(5-pentylthiophen-2-yl)-1,3,2-dioxaborolane Chemical compound S1C(CCCCC)=CC=C1B1OC(C)(C)C(C)(C)O1 VHOQONMRVDSCNI-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 150000001347 alkyl bromides Chemical class 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
- 230000017858 demethylation Effects 0.000 description 3
- 238000010520 demethylation reaction Methods 0.000 description 3
- 239000003989 dielectric material Substances 0.000 description 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000007646 gravure printing Methods 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000813 microcontact printing Methods 0.000 description 3
- 238000007645 offset printing Methods 0.000 description 3
- 238000007649 pad printing Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000010129 solution processing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 3
- YMTNDDOLCXZMND-UHFFFAOYSA-N trimethyl-(5-propylthiophen-2-yl)stannane Chemical compound CCCC1=CC=C([Sn](C)(C)C)S1 YMTNDDOLCXZMND-UHFFFAOYSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 229920003026 Acene Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000005841 biaryl group Chemical group 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VCUDBOXVJZSMOK-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-henicosafluorodecane-1-thiol Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)S VCUDBOXVJZSMOK-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 1
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical class C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- NOYVOSGVFSEKPR-UHFFFAOYSA-N 2-Pentylthiophene Chemical compound CCCCCC1=CC=CS1 NOYVOSGVFSEKPR-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- BTXIJTYYMLCUHI-UHFFFAOYSA-N 2-propylthiophene Chemical compound CCCC1=CC=CS1 BTXIJTYYMLCUHI-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 1
- AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 description 1
- 229920001621 AMOLED Polymers 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 229910017049 AsF5 Inorganic materials 0.000 description 1
- 229910017048 AsF6 Inorganic materials 0.000 description 1
- 229910015845 BBr3 Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910005185 FSO3H Inorganic materials 0.000 description 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
- 229910015400 FeC13 Inorganic materials 0.000 description 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
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Classifications
-
- 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
-
- 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
- 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
-
- 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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- 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
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- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
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- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08159525 | 2008-07-02 | ||
| EP08159525.8 | 2008-07-02 | ||
| PCT/EP2009/057985 WO2010000670A1 (en) | 2008-07-02 | 2009-06-25 | High performance solution processable seminconductor based on dithieno [2,3-d:2',3'-d']benzo[1,2-b:4,5-b'] dithiophene |
Publications (1)
| Publication Number | Publication Date |
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| CA2729334A1 true CA2729334A1 (en) | 2010-01-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2729334A Abandoned CA2729334A1 (en) | 2008-07-02 | 2009-06-25 | High performance solution processable seminconductor based on dithieno [2,3-d:2',3'-d']benzo[1,2-b:4,5-b'] dithiophene |
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| Country | Link |
|---|---|
| US (1) | US8367717B2 (enExample) |
| EP (1) | EP2307424B1 (enExample) |
| JP (1) | JP2011526588A (enExample) |
| KR (2) | KR101855051B1 (enExample) |
| CN (1) | CN102083838B (enExample) |
| CA (1) | CA2729334A1 (enExample) |
| TW (1) | TWI471328B (enExample) |
| WO (1) | WO2010000670A1 (enExample) |
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| GB2465626B (en) * | 2008-11-28 | 2013-07-31 | Cambridge Display Tech Ltd | Organic semiconductors |
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| WO2010149451A1 (en) | 2009-06-05 | 2010-12-29 | Basf Se | Fused bithiophene-vinylene polymers |
| KR20120052222A (ko) | 2009-06-15 | 2012-05-23 | 리어케 메탈즈 인코포레이티드 | 위치규칙성 폴리-(3-치환된) 티오펜, 셀레노펜, 티아졸 및 셀레나졸을 제조하는 방법 |
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| JP5847800B2 (ja) | 2010-04-19 | 2016-01-27 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ベンゾジチオフェンのポリマーおよび有機半導体としてのそれらの使用 |
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| JP2012206953A (ja) * | 2011-03-29 | 2012-10-25 | Tosoh Corp | ジチエノベンゾジチオフェン誘導体及びこれを用いた有機薄膜トランジスタ |
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| JP6108329B2 (ja) * | 2011-08-15 | 2017-04-05 | 国立大学法人東京工業大学 | 有機半導体材料 |
| JP5834673B2 (ja) * | 2011-09-16 | 2015-12-24 | 株式会社リコー | ジチエノベンゾジチオフェン誘導体からなる有機発光材料、発光部材、有機発光デバイス |
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| CN103242343B (zh) * | 2013-05-15 | 2015-12-09 | 北京博如德工程技术研究有限公司 | 一种有机小分子半导体材料及其制备方法 |
| CN103289062B (zh) * | 2013-06-04 | 2015-10-28 | 孟鸿 | 一种网状低能级p型聚合物半导体材料及其制备方法与应用 |
| JP6252032B2 (ja) * | 2013-08-19 | 2017-12-27 | 東ソー株式会社 | ベンゾジフラン誘導体及び有機薄膜トランジスタ |
| KR101595919B1 (ko) * | 2013-08-30 | 2016-02-29 | 한국과학기술연구원 | 전도성 유기 반도체 화합물 및 이를 포함하는 유기태양전지 |
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| JP6295781B2 (ja) * | 2014-03-28 | 2018-03-20 | 東ソー株式会社 | ヘテロアセン誘導体、有機半導体層、及び有機薄膜トランジスタ |
| JP6331579B2 (ja) * | 2014-03-28 | 2018-05-30 | 東ソー株式会社 | ヘテロアセン誘導体、有機半導体層、及び有機薄膜トランジスタ |
| JP6344063B2 (ja) * | 2014-05-29 | 2018-06-20 | 東ソー株式会社 | ジチエノベンゾジチオフェン誘導体の製造方法 |
| JP6318863B2 (ja) * | 2014-05-29 | 2018-05-09 | 東ソー株式会社 | ジチエノベンゾジチオフェン誘導体の製造方法 |
| EP3171420A4 (en) * | 2014-07-18 | 2017-07-05 | Fujifilm Corporation | Organic semiconductor film formation composition, organic semiconductor element, and production method therefor |
| JP6372290B2 (ja) * | 2014-10-07 | 2018-08-15 | 東ソー株式会社 | １，４−ビス（３−ハロ−２−チエニル）−２，５−ジハロベンゼンの製造方法 |
| CN104393174B (zh) * | 2014-10-27 | 2017-02-15 | 中国科学院化学研究所 | 一种有机场效应晶体管及其在紫外光传感中的应用 |
| EP3050887B1 (en) | 2015-01-29 | 2017-06-28 | Samsung Electronics Co., Ltd. | Fused polycyclic heteroaromatic compound, organic thin film including compound and electronic device including organic thin film |
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| JP6399956B2 (ja) * | 2015-03-31 | 2018-10-03 | 東ソー株式会社 | ヘテロアセン誘導体、その製造方法、有機半導体層、及び有機薄膜トランジスタ |
| JP6597087B2 (ja) * | 2015-09-09 | 2019-10-30 | Ｄｉｃ株式会社 | 有機化合物、その製造方法、それを含有する有機半導体材料及びそれを含有する有機トランジスタ |
| EP3379590A4 (en) | 2015-11-20 | 2018-12-05 | Fujifilm Corporation | Organic semiconductor composition, organic semiconductor film, organic thin film transistor and method for manufacturing organic thin film transistor |
| EP3522243A4 (en) | 2016-09-29 | 2019-10-23 | FUJIFILM Corporation | COMPOSITION FOR FORMING AN ORGANIC SEMICONDUCTOR FILM, ORGANIC SEMICONDUCTOR FILM AND METHOD FOR THE PRODUCTION THEREOF AND ORGANIC SEMICONDUCTOR ELEMENT |
| CN109791983B (zh) * | 2016-09-29 | 2023-06-16 | 富士胶片株式会社 | 微晶有机半导体膜、有机半导体晶体管及其制造方法 |
| EP3551635B1 (en) * | 2016-12-06 | 2021-04-28 | Basf Se | Thieno-indeno-monomers and polymers |
| JP7034541B2 (ja) * | 2017-07-18 | 2022-03-14 | 株式会社日本触媒 | 縮合多環式化合物 |
| US10686145B2 (en) | 2017-07-28 | 2020-06-16 | Samsung Electronics Co., Ltd. | Organic compound, organic thin film, and electronic device |
| KR102464890B1 (ko) | 2017-10-18 | 2022-11-07 | 삼성전자주식회사 | 축합다환 헤테로방향족 화합물, 유기 박막 및 전자 소자 |
| CN111471055B (zh) * | 2020-01-17 | 2021-07-16 | 中国长江三峡集团有限公司 | 苯并三噻吩的二维非富勒烯受体材料与用途 |
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| US4423995A (en) * | 1981-06-17 | 1984-01-03 | Beloit Corporation | Arrangement for automatic changeover between ream and skid loading in a continuous sheeter |
| US5198153A (en) | 1989-05-26 | 1993-03-30 | International Business Machines Corporation | Electrically conductive polymeric |
| JP3224829B2 (ja) | 1991-08-15 | 2001-11-05 | 株式会社東芝 | 有機電界効果型素子 |
| WO1996021659A1 (en) | 1995-01-10 | 1996-07-18 | University Of Technology, Sydney | Organic semiconductor |
| EP1839339A2 (en) | 2004-12-23 | 2007-10-03 | Northwestern University | Siloxane-polymer dielectric compositions and related organic field-effect transistors |
| JP2007088016A (ja) * | 2005-09-20 | 2007-04-05 | Konica Minolta Holdings Inc | 有機半導体材料、有機半導体膜、有機半導体デバイス、有機薄膜トランジスタ及び有機エレクトロルミネッセンス素子 |
| EP2573833B1 (en) * | 2005-12-12 | 2014-04-02 | Basf Se | Organic semiconductors, their manufacture and semiconductor devices comprising them |
| US7678463B2 (en) | 2005-12-20 | 2010-03-16 | Northwestern University | Intercalated superlattice compositions and related methods for modulating dielectric property |
| JP5499422B2 (ja) | 2006-06-28 | 2014-05-21 | コニカミノルタ株式会社 | 有機半導体材料、有機半導体膜、有機薄膜トランジスタ及び有機薄膜トランジスタの製造方法 |
| US8138355B2 (en) * | 2006-08-28 | 2012-03-20 | Tosoh Corporation | Heteroacene derivative, tetrahaloterphenyl derivative, and processes for producing the same |
| JP5272345B2 (ja) * | 2006-08-28 | 2013-08-28 | 東ソー株式会社 | ヘテロアセン誘導体、テトラハロターフェニル誘導体及びそれらの製造方法 |
| WO2009016107A1 (en) | 2007-07-30 | 2009-02-05 | Basf Se | Method for depositing a semiconducting layer from a liquid |
| JP5160842B2 (ja) * | 2007-08-28 | 2013-03-13 | 山本化成株式会社 | 有機トランジスタ |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR101855051B1 (ko) | 2018-05-04 |
| CN102083838A (zh) | 2011-06-01 |
| EP2307424A1 (en) | 2011-04-13 |
| KR20110031364A (ko) | 2011-03-25 |
| TWI471328B (zh) | 2015-02-01 |
| JP2011526588A (ja) | 2011-10-13 |
| TW201008948A (en) | 2010-03-01 |
| CN102083838B (zh) | 2016-05-25 |
| KR20170010056A (ko) | 2017-01-25 |
| US8367717B2 (en) | 2013-02-05 |
| EP2307424B1 (en) | 2018-08-15 |
| WO2010000670A1 (en) | 2010-01-07 |
| US20110155248A1 (en) | 2011-06-30 |
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