CN101528753A - 新型缩合多环芳香族化合物及其制造方法和用途 - Google Patents
新型缩合多环芳香族化合物及其制造方法和用途 Download PDFInfo
- Publication number
- CN101528753A CN101528753A CNA200780039700XA CN200780039700A CN101528753A CN 101528753 A CN101528753 A CN 101528753A CN A200780039700X A CNA200780039700X A CN A200780039700XA CN 200780039700 A CN200780039700 A CN 200780039700A CN 101528753 A CN101528753 A CN 101528753A
- Authority
- CN
- China
- Prior art keywords
- compound
- general formula
- changing
- organic semiconductor
- represented
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 107
- 150000001491 aromatic compounds Chemical class 0.000 title abstract description 23
- 230000008569 process Effects 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 171
- 239000004065 semiconductor Substances 0.000 claims abstract description 156
- 239000000463 material Substances 0.000 claims abstract description 128
- 125000003118 aryl group Chemical group 0.000 claims abstract description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
- 230000005669 field effect Effects 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims description 60
- 238000004519 manufacturing process Methods 0.000 claims description 59
- 150000001787 chalcogens Chemical class 0.000 claims description 40
- 230000000694 effects Effects 0.000 claims description 35
- 229910052798 chalcogen Inorganic materials 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000000304 alkynyl group Chemical group 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 238000012546 transfer Methods 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000004414 alkyl thio group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 239000003153 chemical reaction reagent Substances 0.000 claims description 24
- 238000009833 condensation Methods 0.000 claims description 24
- 230000005494 condensation Effects 0.000 claims description 24
- 125000000524 functional group Chemical group 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 23
- 239000002800 charge carrier Substances 0.000 claims description 22
- 239000010409 thin film Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 239000005864 Sulphur Substances 0.000 claims description 10
- 125000005605 benzo group Chemical group 0.000 claims description 10
- VLXBWPOEOIIREY-UHFFFAOYSA-N dimethyl diselenide Chemical compound C[Se][Se]C VLXBWPOEOIIREY-UHFFFAOYSA-N 0.000 claims description 6
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical group CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 claims description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 abstract description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 6
- 230000009878 intermolecular interaction Effects 0.000 abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 abstract description 6
- 239000001301 oxygen Substances 0.000 abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 182
- 239000000758 substrate Substances 0.000 description 53
- 239000010408 film Substances 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 230000037230 mobility Effects 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- -1 phenyl aldehyde Chemical class 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 18
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 229910052710 silicon Inorganic materials 0.000 description 18
- 239000010703 silicon Substances 0.000 description 18
- 239000011241 protective layer Substances 0.000 description 17
- 239000011347 resin Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 11
- 230000006870 function Effects 0.000 description 11
- 229930192474 thiophene Natural products 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000000151 deposition Methods 0.000 description 10
- BOCFGAMKSYQRCI-UHFFFAOYSA-N dinaphtho[2,3-b:2',3'-d]furan Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4OC3=CC2=C1 BOCFGAMKSYQRCI-UHFFFAOYSA-N 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 230000008021 deposition Effects 0.000 description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 description 8
- 239000011630 iodine Substances 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 7
- 235000012239 silicon dioxide Nutrition 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 6
- 239000000956 alloy Substances 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 238000004455 differential thermal analysis Methods 0.000 description 6
- 230000005611 electricity Effects 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 6
- OWQUYBAASOSGNO-CDNKMLFNSA-N 2-[[(Z)-N-(2-hydroxy-5-sulfoanilino)-C-phenylcarbonimidoyl]diazenyl]benzoic acid Chemical compound C1=CC=C(C=C1)/C(=N/NC2=C(C=CC(=C2)S(=O)(=O)O)O)/N=NC3=CC=CC=C3C(=O)O OWQUYBAASOSGNO-CDNKMLFNSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003541 multi-stage reaction Methods 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000011669 selenium Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 5
- 229940043798 zincon Drugs 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 229920001197 polyacetylene Polymers 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000007670 refining Methods 0.000 description 4
- 238000003980 solgel method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WWIKFXPBGKBXLZ-UHFFFAOYSA-N 6-methylnaphthalene-2-carbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(C)=CC=C21 WWIKFXPBGKBXLZ-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229920000265 Polyparaphenylene Polymers 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 229910052581 Si3N4 Inorganic materials 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 235000002597 Solanum melongena Nutrition 0.000 description 3
- 244000061458 Solanum melongena Species 0.000 description 3
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 229940091250 magnesium supplement Drugs 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 238000000206 photolithography Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 3
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 229920003026 Acene Polymers 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004695 Polyether sulfone Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 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 2
- 238000007645 offset printing Methods 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
- 239000011112 polyethylene naphthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- TYWAOIBYSDORAH-UHFFFAOYSA-N 1,2-bis(4-aminophenyl)ethane-1,2-dione Chemical compound C1=CC(N)=CC=C1C(=O)C(=O)C1=CC=C(N)C=C1 TYWAOIBYSDORAH-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- MKFDXMSXDXBYSD-UHFFFAOYSA-N 6-methyl-2-[2-(6-methyl-3-methylsulfanylnaphthalen-2-yl)ethenyl]-3-methylsulfanylnaphthalene Chemical group C1=C(C)C=C2C=C(SC)C(C=CC3=CC4=CC=C(C)C=C4C=C3SC)=CC2=C1 MKFDXMSXDXBYSD-UHFFFAOYSA-N 0.000 description 1
- XWUYJMONJUOJCD-UHFFFAOYSA-N 6-methyl-3-methylsulfanylnaphthalene-2-carbaldehyde Chemical compound CC1=CC=C2C=C(C=O)C(SC)=CC2=C1 XWUYJMONJUOJCD-UHFFFAOYSA-N 0.000 description 1
- AAFVYQRQJBENSZ-UHFFFAOYSA-N 6-methylnaphthalene-2-carbaldehyde Chemical compound CC=1C=C2C=CC(=CC2=CC1)C=O.CC=1C=C2C=CC(=CC2=CC1)C=O AAFVYQRQJBENSZ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 101100391174 Dictyostelium discoideum forC gene Proteins 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 229910005540 GaP Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- DPBBOLLANMIQSE-UHFFFAOYSA-N N=1OC=C2C1C=CC=C2.N=2OC=C1C=CC=CC21 Chemical compound N=1OC=C2C1C=CC=C2.N=2OC=C1C=CC=CC21 DPBBOLLANMIQSE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910002367 SrTiO Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001786 chalcogen compounds Chemical class 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 230000005685 electric field effect Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- HZXMRANICFIONG-UHFFFAOYSA-N gallium phosphide Chemical compound [Ga]#P HZXMRANICFIONG-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 238000000608 laser ablation Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229940073589 magnesium chloride anhydrous Drugs 0.000 description 1
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- VOFUROIFQGPCGE-UHFFFAOYSA-N nile red Chemical compound C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=O)C2=C1 VOFUROIFQGPCGE-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- UEXCJVNBTNXOEH-UHFFFAOYSA-N phenyl acethylene Natural products C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001510 poly[2-(diisopropylamino)ethyl methacrylate] polymer Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000015 polydiacetylene Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 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
- 238000012360 testing method Methods 0.000 description 1
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
- C07C391/02—Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic 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
- C07D495/02—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
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
- C07D517/04—Ortho-condensed systems
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/30—Organic light-emitting transistors
-
- 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
-
- 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
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Thin Film Transistor (AREA)
Abstract
Description
Claims (17)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP290192/2006 | 2006-10-25 | ||
JP2006290192 | 2006-10-25 | ||
PCT/JP2007/070569 WO2008050726A1 (fr) | 2006-10-25 | 2007-10-22 | Nouveau composé aromatique à cycle fusionne, son procédé de production et son utilisation |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101528753A true CN101528753A (zh) | 2009-09-09 |
CN101528753B CN101528753B (zh) | 2012-05-23 |
Family
ID=39324523
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200780039700XA Active CN101528753B (zh) | 2006-10-25 | 2007-10-22 | 缩合多环芳香族化合物及其制造方法和用途 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8232546B2 (zh) |
EP (1) | EP2098527B1 (zh) |
JP (1) | JP4958119B2 (zh) |
KR (1) | KR101177970B1 (zh) |
CN (1) | CN101528753B (zh) |
TW (1) | TWI363760B (zh) |
WO (1) | WO2008050726A1 (zh) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101798310A (zh) * | 2010-03-05 | 2010-08-11 | 中国科学院长春应用化学研究所 | 一种有机半导体材料及使用该材料的有机薄膜晶体管 |
CN102596889A (zh) * | 2009-09-11 | 2012-07-18 | 株式会社理光 | 含有离去取代基的化合物、有机半导体材料、含有该材料的有机半导体膜、含有该膜的有机电子器件、制备膜状产品的方法、π-电子共轭的化合物和制备该π-电子共轭的化合物的方法 |
CN103391942A (zh) * | 2011-02-25 | 2013-11-13 | 国立大学法人广岛大学 | 新型杂环化合物、制造其中间体的方法及其用途 |
CN103717606A (zh) * | 2011-08-05 | 2014-04-09 | 帝人株式会社 | 稠合多环芳香族化合物、芳香族聚合物及芳香族化合物的合成方法 |
CN104584251A (zh) * | 2012-08-15 | 2015-04-29 | 帝人株式会社 | 有机半导体溶液和有机半导体膜 |
CN104903329A (zh) * | 2012-08-24 | 2015-09-09 | 日本化药株式会社 | 生产芳族化合物的方法 |
CN104956508A (zh) * | 2013-01-22 | 2015-09-30 | 日本化药株式会社 | 溶液工艺用有机半导体材料和有机半导体设备 |
CN105493303A (zh) * | 2013-08-28 | 2016-04-13 | 斯马特凯姆有限公司 | 聚合物有机半导体组合物 |
CN105837597A (zh) * | 2015-01-29 | 2016-08-10 | 三星电子株式会社 | 稠合多环杂芳族化合物、包括所述化合物的有机薄膜和包括有机薄膜的电子器件 |
KR20170046399A (ko) * | 2015-10-21 | 2017-05-02 | 삼성전자주식회사 | 헤테로아센 화합물의 중간체 및 이를 이용한 헤테로아센 화합물의 합성 방법 |
US9796727B2 (en) | 2009-02-27 | 2017-10-24 | Nippon Kayaku Kabushiki Kaisha | Field effect transistor |
KR20180051260A (ko) * | 2016-11-08 | 2018-05-16 | 삼성전자주식회사 | 축합 헤테로방향족 화합물의 합성 방법, 축합 헤테로방향족 화합물 및 그 중간체 및 합성 방법 |
US10686145B2 (en) | 2017-07-28 | 2020-06-16 | Samsung Electronics Co., Ltd. | Organic compound, organic thin film, and electronic device |
Families Citing this family (55)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009129943A (ja) * | 2007-11-20 | 2009-06-11 | Mitsubishi Electric Corp | 窒化物半導体装置とその製造方法 |
JP5481850B2 (ja) * | 2008-01-23 | 2014-04-23 | 東ソー株式会社 | ヘテロアセン誘導体、その前駆化合物及びそれらの製造方法 |
JP5288372B2 (ja) * | 2008-06-19 | 2013-09-11 | 国立大学法人広島大学 | 芳香族化合物の誘導体とそれらの中間体の製造方法 |
JP2010083785A (ja) * | 2008-09-30 | 2010-04-15 | Chisso Corp | 平面性の高い分子構造を有する化合物およびこれを用いた有機トランジスタ |
US7872258B2 (en) * | 2008-11-19 | 2011-01-18 | Xerox Corporation | Organic thin-film transistors |
JP5467676B2 (ja) * | 2009-05-26 | 2014-04-09 | 日本化薬株式会社 | 芳香族化合物の製造方法 |
JP5390959B2 (ja) * | 2009-06-30 | 2014-01-15 | ウシオケミックス株式会社 | スルホン構造を有する有機半導体化合物 |
KR101068575B1 (ko) * | 2009-07-03 | 2011-09-30 | 주식회사 하이닉스반도체 | 반도체 장치 및 그 제조방법 |
JP2011162510A (ja) * | 2010-02-12 | 2011-08-25 | Teijin Ltd | 新規なα−ジケトン化合物、及び有機半導体デバイス |
KR101604513B1 (ko) * | 2009-08-28 | 2016-03-17 | 데이진 가부시키가이샤 | 신규한 부가 화합물, 축합 다고리 방향족 화합물의 정제 및 제조 방법, 유기 반도체막 형성용 용액, 및 신규한 α-디케톤 화합물 |
JP2011148743A (ja) * | 2010-01-22 | 2011-08-04 | Teijin Ltd | 縮合多環芳香族化合物の精製及び製造方法 |
JP5269825B2 (ja) * | 2009-08-28 | 2013-08-21 | 帝人株式会社 | 新規な付加化合物、及び有機半導体デバイス |
JP5733553B2 (ja) * | 2010-01-12 | 2015-06-10 | 株式会社リコー | 置換基脱離化合物および有機半導体材料およびその膜およびそれを用いた有機トランジスタ |
JP5478189B2 (ja) * | 2009-10-16 | 2014-04-23 | 学校法人東海大学 | 大気安定性に優れた有機トランジスタ |
US8968887B2 (en) * | 2010-04-28 | 2015-03-03 | Universal Display Corporation | Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings |
JP2011256144A (ja) * | 2010-06-10 | 2011-12-22 | Yamamoto Chem Inc | チオフェン化合物の製造方法 |
JP5765559B2 (ja) * | 2010-06-15 | 2015-08-19 | 株式会社リコー | 置換基脱離化合物とそれから得られる有機半導体材料、それを用いた有機電子デバイス、有機薄膜トランジスタおよびディスプレイ装置 |
JP5263250B2 (ja) * | 2010-09-24 | 2013-08-14 | 株式会社デンソー | 化合物、有機半導体材料、及び半導体デバイス |
KR101736971B1 (ko) | 2010-10-01 | 2017-05-30 | 삼성전자주식회사 | 그래핀 전자 소자 및 제조방법 |
JP5761841B2 (ja) * | 2010-10-27 | 2015-08-12 | 日本化薬株式会社 | フェノール性水酸基含有芳香族ポリアミド樹脂を含有する絶縁層を有する有機半導体素子並びにその製造方法 |
KR101813179B1 (ko) | 2011-06-10 | 2017-12-29 | 삼성전자주식회사 | 복층의 게이트 절연층을 구비한 그래핀 전자 소자 |
EP2755978A1 (en) * | 2011-09-12 | 2014-07-23 | Polyera Corporation | Compounds having semiconducting properties and related compositions and devices |
US8658805B2 (en) | 2011-11-07 | 2014-02-25 | Samsung Electronics Co., Ltd. | Fused polyheteroaromatic compound, organic thin film including the compound, and electronic device including the organic thin film |
EP2818464A4 (en) | 2012-02-22 | 2015-11-18 | Jnc Corp | NOVEL CHALCO-CONTAINING ORGANIC COMPOUND AND USE THEREOF |
GB201203159D0 (en) | 2012-02-23 | 2012-04-11 | Smartkem Ltd | Organic semiconductor compositions |
JP5958988B2 (ja) | 2012-03-16 | 2016-08-02 | Jnc株式会社 | 有機半導体薄膜、有機半導体素子および有機電界効果トランジスタ |
US9133156B2 (en) | 2012-07-06 | 2015-09-15 | Sejong University Industry Academy Cooperation Foundation | Method for preparing selenyl-substituted aromatic aldehyde compounds |
EP2886546B1 (en) | 2012-08-14 | 2018-10-10 | Nippon Kayaku Kabushiki Kaisha | Heterocyclic compound and use thereof |
US10089930B2 (en) | 2012-11-05 | 2018-10-02 | University Of Florida Research Foundation, Incorporated | Brightness compensation in a display |
WO2014085410A1 (en) * | 2012-11-30 | 2014-06-05 | University Of Florida Research Foundation, Inc. | Ambipolar vertical field effect transistor |
WO2014094954A1 (en) * | 2012-12-18 | 2014-06-26 | Merck Patent Gmbh | Indenophenanthrene based compounds |
WO2014136436A1 (ja) * | 2013-03-04 | 2014-09-12 | 出光興産株式会社 | 有機薄膜トランジスタ及びその製造方法 |
CN105102462B (zh) | 2013-03-05 | 2018-02-02 | 捷恩智株式会社 | 含有氧族元素的有机化合物、其制造方法以及用途 |
KR101493032B1 (ko) * | 2013-12-10 | 2015-02-17 | 세종대학교산학협력단 | 셀레닐-치환된 방향족 알데하이드계 화합물의 신규 제조 방법 |
WO2015129877A1 (ja) * | 2014-02-28 | 2015-09-03 | 国立大学法人 奈良先端科学技術大学院大学 | 熱電変換材料および熱電変換素子 |
US10522771B2 (en) | 2014-12-01 | 2019-12-31 | Samsung Electronics Co., Ltd. | Composition, electronic device, and thin film transistor |
JP2016113434A (ja) * | 2014-12-18 | 2016-06-23 | 住友化学株式会社 | 化合物、該化合物と高分子化合物を含む組成物、該化合物を含む有機薄膜および有機半導体素子 |
WO2016180535A1 (en) | 2015-05-12 | 2016-11-17 | Pixium Vision Sa | Photosensitive pixel structure with wrapped resistor |
KR102407114B1 (ko) | 2015-05-29 | 2022-06-08 | 삼성전자주식회사 | 절연액, 절연체, 박막 트랜지스터 및 전자 소자 |
US10230059B2 (en) | 2015-06-19 | 2019-03-12 | Samsung Electronics Co., Ltd. | Organic compound and organic thin film and electronic device |
EP3313503B1 (en) | 2015-06-24 | 2022-08-31 | Pixium Vision SA | Photosensitive pixel structure with increased light absorption and photosensitive implant |
KR102380151B1 (ko) | 2015-08-31 | 2022-03-28 | 삼성전자주식회사 | 박막 트랜지스터, 및 이를 포함하는 전자 장치 |
KR102459389B1 (ko) | 2015-09-08 | 2022-10-25 | 삼성전자주식회사 | 축합다환 헤테로방향족 화합물, 이를 포함하는 유기 박막 및 상기 유기 박막을 포함하는 전자 소자 |
EP3144032A1 (en) * | 2015-09-15 | 2017-03-22 | Pixium Vision SA | Photosensitive pixel structure with front side coating |
KR102520104B1 (ko) | 2015-10-12 | 2023-04-07 | 삼성전자주식회사 | 축합다환 헤테로방향족 화합물, 이를 포함하는 유기 박막 및 상기 유기 박막을 포함하는 전자 소자 |
US10056563B2 (en) | 2016-04-08 | 2018-08-21 | Samsung Electronics Co., Ltd. | Synthetic method of fused heteroaromatic compound and fused heteroaromatic compound, and intermediate thereof |
JP6910880B2 (ja) * | 2016-08-03 | 2021-07-28 | 日本化薬株式会社 | 有機光電変換素子、有機光電変換素子用材料及びこれらを用いた有機撮像素子 |
EP3427790A1 (en) | 2017-07-14 | 2019-01-16 | Pixium Vision SA | Photosensitive array |
KR102464890B1 (ko) | 2017-10-18 | 2022-11-07 | 삼성전자주식회사 | 축합다환 헤테로방향족 화합물, 유기 박막 및 전자 소자 |
WO2020045597A1 (ja) * | 2018-08-31 | 2020-03-05 | 国立大学法人 東京大学 | カルコゲン含有有機化合物、有機半導体材料、有機半導体膜、及び有機電界効果トランジスタ |
KR20200061888A (ko) | 2018-11-26 | 2020-06-03 | 삼성전자주식회사 | 화합물, 유기 박막, 박막 트랜지스터 및 전자 소자 |
KR102684640B1 (ko) | 2018-12-03 | 2024-07-11 | 삼성전자주식회사 | 유기 박막, 유기 박막 트랜지스터 및 전자 소자 |
KR20220063189A (ko) | 2019-09-17 | 2022-05-17 | 닛뽄 가야쿠 가부시키가이샤 | 축합 다환 방향족 화합물 |
TW202136272A (zh) | 2019-12-10 | 2021-10-01 | 日商日本化藥股份有限公司 | 縮合多環芳香族化合物 |
WO2023189381A1 (ja) * | 2022-03-30 | 2023-10-05 | ソニーグループ株式会社 | 発光素子および電子機器 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3377494B2 (ja) | 2000-03-13 | 2003-02-17 | 科学技術振興事業団 | ポリチオフェンラダー化合物とその製造法 |
EP1138328A1 (en) * | 2000-03-29 | 2001-10-04 | Eli Lilly And Company Limited | Naphthalene derivatives as CNS drugs |
JP4177286B2 (ja) * | 2004-05-11 | 2008-11-05 | 独立行政法人科学技術振興機構 | 新規なアントラセン誘導体 |
JP2006031893A (ja) | 2004-07-21 | 2006-02-02 | Matsushita Electric Ind Co Ltd | 光ディスク装置 |
JP2006077888A (ja) | 2004-09-09 | 2006-03-23 | Nsk Warner Kk | クラッチハブ |
CN101111497B (zh) | 2004-09-14 | 2013-10-30 | 康宁股份有限公司 | 稠合噻吩及其制备方法和用途 |
JP2006199909A (ja) | 2004-12-20 | 2006-08-03 | Seiko Epson Corp | 導電性材料用組成物、導電性材料、導電層、電子デバイスおよび電子機器 |
WO2006077888A1 (ja) * | 2005-01-19 | 2006-07-27 | National University Of Corporation Hiroshima University | 新規な縮合多環芳香族化合物およびその利用 |
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 |
KR20080100982A (ko) * | 2007-05-15 | 2008-11-21 | 삼성전자주식회사 | 헤테로아센 화합물, 이를 포함하는 유기 박막 및 상기박막을 포함하는 전자 소자 |
-
2007
- 2007-10-22 KR KR1020097010362A patent/KR101177970B1/ko active IP Right Grant
- 2007-10-22 US US12/312,083 patent/US8232546B2/en active Active
- 2007-10-22 JP JP2008540982A patent/JP4958119B2/ja active Active
- 2007-10-22 EP EP07830303.9A patent/EP2098527B1/en active Active
- 2007-10-22 WO PCT/JP2007/070569 patent/WO2008050726A1/ja active Search and Examination
- 2007-10-22 CN CN200780039700XA patent/CN101528753B/zh active Active
- 2007-10-23 TW TW096139747A patent/TWI363760B/zh active
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9796727B2 (en) | 2009-02-27 | 2017-10-24 | Nippon Kayaku Kabushiki Kaisha | Field effect transistor |
US9224959B2 (en) | 2009-09-11 | 2015-12-29 | Ricoh Company, Ltd. | Method for producing a pi-electron conjugated compound |
US9123896B2 (en) | 2009-09-11 | 2015-09-01 | Ricoh Company, Ltd. | Organic electronic device containing an organic semiconductor material film which contains a leaving substituent-containing compound |
US8680296B2 (en) | 2009-09-11 | 2014-03-25 | Ricoh Company, Ltd. | Leaving substituent-containing compound, products produced using the same, and methods for producing the products |
CN102596889A (zh) * | 2009-09-11 | 2012-07-18 | 株式会社理光 | 含有离去取代基的化合物、有机半导体材料、含有该材料的有机半导体膜、含有该膜的有机电子器件、制备膜状产品的方法、π-电子共轭的化合物和制备该π-电子共轭的化合物的方法 |
CN102596889B (zh) * | 2009-09-11 | 2016-01-20 | 株式会社理光 | 含有离去取代基的化合物及其在有机电子产品中的应用 |
CN101798310A (zh) * | 2010-03-05 | 2010-08-11 | 中国科学院长春应用化学研究所 | 一种有机半导体材料及使用该材料的有机薄膜晶体管 |
CN103391942B (zh) * | 2011-02-25 | 2015-11-25 | 日本化药株式会社 | 新型杂环化合物、制造其中间体的方法及其用途 |
CN104650110A (zh) * | 2011-02-25 | 2015-05-27 | 日本化药株式会社 | 新型杂环化合物、制造其中间体的方法及其用途 |
US9018630B2 (en) | 2011-02-25 | 2015-04-28 | Nippon Kayaku Kabushiki Kaisha | Heterocyclic dinaphtho thieno thiophene (DNTT) compounds for use as organic semiconductor thin films in field effect transistors and related methods |
CN103391942A (zh) * | 2011-02-25 | 2013-11-13 | 国立大学法人广岛大学 | 新型杂环化合物、制造其中间体的方法及其用途 |
CN104650110B (zh) * | 2011-02-25 | 2017-04-12 | 日本化药株式会社 | 新型杂环化合物、制造其中间体的方法及其用途 |
CN103717606A (zh) * | 2011-08-05 | 2014-04-09 | 帝人株式会社 | 稠合多环芳香族化合物、芳香族聚合物及芳香族化合物的合成方法 |
CN104584251A (zh) * | 2012-08-15 | 2015-04-29 | 帝人株式会社 | 有机半导体溶液和有机半导体膜 |
CN104903329A (zh) * | 2012-08-24 | 2015-09-09 | 日本化药株式会社 | 生产芳族化合物的方法 |
CN104956508A (zh) * | 2013-01-22 | 2015-09-30 | 日本化药株式会社 | 溶液工艺用有机半导体材料和有机半导体设备 |
CN104956508B (zh) * | 2013-01-22 | 2017-07-21 | 日本化药株式会社 | 溶液工艺用有机半导体材料和有机半导体设备 |
CN105493303A (zh) * | 2013-08-28 | 2016-04-13 | 斯马特凯姆有限公司 | 聚合物有机半导体组合物 |
CN105493303B (zh) * | 2013-08-28 | 2019-02-22 | 斯马特凯姆有限公司 | 聚合物有机半导体组合物 |
CN105837597A (zh) * | 2015-01-29 | 2016-08-10 | 三星电子株式会社 | 稠合多环杂芳族化合物、包括所述化合物的有机薄膜和包括有机薄膜的电子器件 |
CN105837597B (zh) * | 2015-01-29 | 2019-08-16 | 三星电子株式会社 | 稠合多环杂芳族化合物、包括所述化合物的有机薄膜和包括有机薄膜的电子器件 |
US10559764B2 (en) | 2015-01-29 | 2020-02-11 | Samsung Electronics Co., Ltd. | Fused polycyclic heteroaromatic compound, organic thin film including compound and electronic device including organic thin film |
KR20170046399A (ko) * | 2015-10-21 | 2017-05-02 | 삼성전자주식회사 | 헤테로아센 화합물의 중간체 및 이를 이용한 헤테로아센 화합물의 합성 방법 |
CN106967045A (zh) * | 2015-10-21 | 2017-07-21 | 三星电子株式会社 | 杂并苯化合物的中间体、使用其的杂并苯化合物的合成方法和包括杂并苯化合物的电子器件 |
KR102453744B1 (ko) | 2015-10-21 | 2022-10-11 | 삼성전자주식회사 | 헤테로아센 화합물의 중간체 및 이를 이용한 헤테로아센 화합물의 합성 방법 |
KR20180051260A (ko) * | 2016-11-08 | 2018-05-16 | 삼성전자주식회사 | 축합 헤테로방향족 화합물의 합성 방법, 축합 헤테로방향족 화합물 및 그 중간체 및 합성 방법 |
CN108069987A (zh) * | 2016-11-08 | 2018-05-25 | 三星电子株式会社 | 稠合杂芳族化合物的制造方法、稠合杂芳族化合物、电子器件、中间体及其制造方法 |
CN108069987B (zh) * | 2016-11-08 | 2022-03-22 | 三星电子株式会社 | 稠合杂芳族化合物的制造方法、稠合杂芳族化合物、电子器件、中间体及其制造方法 |
KR102677490B1 (ko) | 2016-11-08 | 2024-06-20 | 삼성전자주식회사 | 축합 헤테로방향족 화합물의 합성 방법, 축합 헤테로방향족 화합물 및 그 중간체 및 합성 방법 |
US10686145B2 (en) | 2017-07-28 | 2020-06-16 | Samsung Electronics Co., Ltd. | Organic compound, organic thin film, and electronic device |
Also Published As
Publication number | Publication date |
---|---|
EP2098527B1 (en) | 2016-03-30 |
KR20090074248A (ko) | 2009-07-06 |
JP4958119B2 (ja) | 2012-06-20 |
KR101177970B1 (ko) | 2012-08-28 |
CN101528753B (zh) | 2012-05-23 |
US8232546B2 (en) | 2012-07-31 |
TWI363760B (en) | 2012-05-11 |
TW200838866A (en) | 2008-10-01 |
EP2098527A4 (en) | 2012-05-23 |
EP2098527A1 (en) | 2009-09-09 |
US20100065826A1 (en) | 2010-03-18 |
WO2008050726A1 (fr) | 2008-05-02 |
JPWO2008050726A1 (ja) | 2010-02-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101528753B (zh) | 缩合多环芳香族化合物及其制造方法和用途 | |
JP4945757B2 (ja) | 新規な縮合多環芳香族化合物およびその利用 | |
CN101389634B (zh) | 含氟化合物及其制造方法、含氟聚合物、有机薄膜、以及有机薄膜元件 | |
KR101556095B1 (ko) | 신규의 헤테로고리 화합물 및 그 이용 | |
EP2894685B1 (en) | Benzothienobenzothiophene derivative, organic semiconductor material, and organic transistor | |
EP2818464A1 (en) | Novel chalcogen-containing organic compound and use thereof | |
EP2966077A1 (en) | Chalcogen-containing organic compound and use therefor | |
TW201829410A (zh) | 有機薄膜電晶體、有機半導體膜、化合物、有機薄膜電晶體用組成物及有機薄膜電晶體的製造方法 | |
CN104650110A (zh) | 新型杂环化合物、制造其中间体的方法及其用途 | |
JP2014531435A (ja) | 半導体特性を有する化合物、ならびに関連する組成物およびデバイス | |
CN102333780A (zh) | 场效应晶体管 | |
KR20100016583A (ko) | 치환 펜타센의 제조 방법 | |
CN102209720A (zh) | 新型化合物及有机半导体材料 | |
KR101763054B1 (ko) | 유기 박막 트랜지스터, 유기 반도체 박막 및 유기 반도체 재료 | |
JP2010258214A (ja) | バンドギャップが広いことを特徴とする有機半導体化合物 | |
JP5897050B2 (ja) | 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料 | |
JP6656508B2 (ja) | ベンゾチエノベンゾチオフェン誘導体、有機半導体材料、及び有機トランジスタ | |
Dong et al. | Asymmetrical [1] Benzothieno [3, 2-b][1] benzothiophene (BTBT) derivatives for organic thin-film and single-crystal transistors | |
KR101956970B1 (ko) | 티에노[2,3c]피롤-디온 유도체 및 유기 반도체에 대한 이들의 용도 | |
US20130146858A1 (en) | SEMICONDUCTORS BASED ON SUBSTITUTED [1]BENZOTHIENO[3,2-b][1]-BENZOTHIOPHENES | |
JP5141154B2 (ja) | [1]ベンゾカルコゲノ[3,2−b][1]ベンゾカルコゲノフェン骨格を有する化合物およびこれを用いた有機トランジスタ | |
JP6247568B2 (ja) | 有機薄膜トランジスタ、非発光性有機半導体デバイス用有機半導体材料およびその応用 | |
TW201238971A (en) | Dinaphtho[2,3-a:2',3'-h]phenazines and their use as organic semiconductors | |
TW201841923A (zh) | 有機半導體及其製造方法 | |
JP6413863B2 (ja) | 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 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Free format text: FORMER OWNER: NIPPON KAYAKU KABUSHIKI KAISHA Effective date: 20140307 Owner name: NIPPON KAYAKU KABUSHIKI KAISHA Free format text: FORMER OWNER: NAT UNIVERSITY OF CORP. HIROSHI Effective date: 20140307 |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20140307 Address after: Tokyo, Japan Patentee after: Nippon Kayaku K. K. Address before: Hiroshima Japan Patentee before: Nat University of Corp. Hiroshi Patentee before: Nippon Kayaku K. K. |