KR20070119317A - 티아졸로티아졸 유도체 및 이를 이용한 유기 전자 소자 - Google Patents
티아졸로티아졸 유도체 및 이를 이용한 유기 전자 소자 Download PDFInfo
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- KR20070119317A KR20070119317A KR1020060053801A KR20060053801A KR20070119317A KR 20070119317 A KR20070119317 A KR 20070119317A KR 1020060053801 A KR1020060053801 A KR 1020060053801A KR 20060053801 A KR20060053801 A KR 20060053801A KR 20070119317 A KR20070119317 A KR 20070119317A
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- BDEOXDSSZJCZPE-UHFFFAOYSA-N [1,3]thiazolo[4,5-d][1,3]thiazole Chemical class N1=CSC2=C1N=CS2 BDEOXDSSZJCZPE-UHFFFAOYSA-N 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 16
- 125000002015 acyclic group Chemical group 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 239000000126 substance Substances 0.000 claims description 71
- 239000010410 layer Substances 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 239000011368 organic material Substances 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000002560 nitrile group Chemical group 0.000 claims description 15
- -1 iodine, nitrile group Compound Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000005462 imide group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000004185 ester group Chemical group 0.000 claims description 11
- 125000001033 ether group Chemical group 0.000 claims description 11
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000007970 thio esters Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 description 39
- 239000000243 solution Substances 0.000 description 29
- 239000000463 material Substances 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 239000010409 thin film Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 230000032258 transport Effects 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HRJHHVGEPWHNHN-UHFFFAOYSA-N 5-(3-dodecylthiophen-2-yl)-[1,3]thiazolo[4,5-d][1,3]thiazole Chemical compound C(CCCCCCCCCCC)C1=C(SC=C1)C=1SC2=C(N=1)N=CS2 HRJHHVGEPWHNHN-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 238000012856 packing Methods 0.000 description 5
- 0 *c1c(-c2nc([s]c(-c([s]3)c(*)cc3Br)n3)c3[s]2)[s]c(Br)c1 Chemical compound *c1c(-c2nc([s]c(-c([s]3)c(*)cc3Br)n3)c3[s]2)[s]c(Br)c1 0.000 description 4
- NJPMFDNZCLKTHE-UHFFFAOYSA-N 2-dodecylthiophene Chemical compound CCCCCCCCCCCCC1=CC=CS1 NJPMFDNZCLKTHE-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 3
- IMILVTHOOISGRW-UHFFFAOYSA-N 2-bromo-3-dodecylthiophene Chemical compound CCCCCCCCCCCCC=1C=CSC=1Br IMILVTHOOISGRW-UHFFFAOYSA-N 0.000 description 3
- HKFGSESJCHINGM-UHFFFAOYSA-N 3-dodecylthiophene-2-carbaldehyde Chemical compound CCCCCCCCCCCCC=1C=CSC=1C=O HKFGSESJCHINGM-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000002094 self assembled monolayer Substances 0.000 description 2
- 239000013545 self-assembled monolayer Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 1
- RFKWIEFTBMACPZ-UHFFFAOYSA-N 3-dodecylthiophene Chemical compound CCCCCCCCCCCCC=1C=CSC=1 RFKWIEFTBMACPZ-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- SHYKYJZWHFTVGF-UHFFFAOYSA-N C(CCCCCCCCCCC)C1=CSC=C1.C(CCCCCCCCCCC)C1=CSC=C1 Chemical compound C(CCCCCCCCCCC)C1=CSC=C1.C(CCCCCCCCCCC)C1=CSC=C1 SHYKYJZWHFTVGF-UHFFFAOYSA-N 0.000 description 1
- ANBHUERGQJMRPV-UHFFFAOYSA-N C(CCCCCCCCCCC)C1=CSC=C1.C(CCCCCCCCCCC)C1=CSC=C1.C(CCCCCCCCCCC)C1=CSC=C1 Chemical compound C(CCCCCCCCCCC)C1=CSC=C1.C(CCCCCCCCCCC)C1=CSC=C1.C(CCCCCCCCCCC)C1=CSC=C1 ANBHUERGQJMRPV-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 238000005577 Kumada cross-coupling reaction Methods 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- ZBQUMMFUJLOTQC-UHFFFAOYSA-L dichloronickel;3-diphenylphosphanylpropyl(diphenyl)phosphane Chemical compound Cl[Ni]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 ZBQUMMFUJLOTQC-UHFFFAOYSA-L 0.000 description 1
- OAEGRYMCJYIXQT-UHFFFAOYSA-N dithiooxamide Chemical compound NC(=S)C(N)=S OAEGRYMCJYIXQT-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 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
- 238000005191 phase separation Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/32—Polythiazoles; Polythiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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Abstract
Description
Claims (20)
- 하기 화학식 1의 화합물:[화학식 1]상기 식에서, 0<x≤1의 실수, 0≤y<1의 실수, 0≤z<1의 실수, x+y+z=1이고,n은 1 내지 1000의 정수이고,Ar 및 Ar′는 서로 같거나 상이하고, 독립적으로 공액구조를 갖는 2가의 고리 또는 비고리 탄화수소기 또는 공액구조를 갖는 2가 헤테로고리기이며,A와 B는 서로 같거나 상이하고, 독립적으로 공액구조를 갖는 2가의 고리 또는 비고리 탄화수소기, 공액구조를 갖는 2가의 헤테로고리기, 또는 하기 비환식(acyclic group)기이고,상기 식에서 R′및 R″는 서로 같거나 상이하고, 독립적으로 수소원자; 할로겐원자; 직쇄, 분지쇄 혹은 고리형의 알킬기; 직쇄, 분지쇄 혹은 고리형의 알콕시기; 티오알콕시기; 니트릴기; 니트로기; 아미노기; 치환 혹은 비치환된 아릴기 또 는 헤테로아릴기이며, 점선 부분은 화학식 1의 주쇄에 연결되는 부분이다.
- 청구항 1에 있어서, 상기 Ar 또는 Ar′는 공액 구조를 갖는 아릴렌기 또는 헤테로아릴렌기인 것인 화합물.
- 청구항 1에 있어서, 상기 A 또는 B는 방향족기(Ar″)인 것인 화합물.
- 청구항 3에 있어서, 상기 방향족기 (Ar″)는 하기의 화학식으로 표현되는 기들 중에서 선택되는 것인 화합물:여기서, X는 O, S, Se, NR3, SiR3R4 혹은 CR3R4 기이고, 여기서 R3과 R4는 서로 같거나 상이하고, 독립적으로 수소원자, 직쇄, 분지쇄 혹은 고리형의 알킬기 또는 아릴기이며 이들은 서로 연결되어 고리를 형성하여도 좋으며,R1 및 R2는 서로 같거나 상이하고, 독립적으로 수소원자, 히드록시기, 할로겐원자, 니트릴기, 니트로기, 에스터기, 에테르기, 아미노기, 이미드기, 실란기, 티오에스터기, 탄소수 1~20개의 치환 또는 비치환의 직쇄, 분지쇄 혹은 고리형의 알킬기 , 탄소수 1~20개의 치환 또는 비치환 직쇄, 분지쇄 혹은 고리형의 알콕시기, 탄소수 1~20개의 치환 또는 비치환의 직쇄, 분지쇄 혹은 고리형의 티오알콕시기이고, 치환 또는 비치환된 아릴기, 또한는 치환 또는 비치환의 헤테로 아릴기이며,R1 및/또는 R2에 포함되는 서로 인접하지 않은 2이상의 탄소원자는 O, S, NH, -NRO-, SiROROO-, -CO-, -COO-, -OCO-, -OCOO-, -S-CO-, -CO-S-, -CH=CH-, 치환 또는 비치환된 아릴기 또는 치환 또는 비치환된 헤테로아릴기에 의해 연결될 수 있으며, 여기서 Ro와 Roo는 서로 같거나 상이하고, 독립적으로 수소 , 아릴 또는 탄소수 1~12인 알킬기이고,R1과 R2는 서로 연결되어 고리를 이룰 수 있다.
- 청구항 4에 있어서, 상기 R1 또는 R2가 탄소수 1~20개의 치환된 알킬기, 알콕시기 또는 티오알콕시기인 경우, 이들은 하나 이상의 불소, 염소, 브롬, 요오드, 및 니트릴기로 이루어진 군에서 선택되는 1이상의 치환기에 의해 치환된 것인 화합물.
- 청구항 4에 있어서, 상기 R1 또는 R2가 치환된 아릴기 또는 헤테로아릴기인 경우, 이들은 할로겐기, 니트릴기, 히드록시기, 알킬기, 알콕시기, 비닐기, 아세틸렌기, 티오알콕시기, 니트로기, 아미드기, 이미드기, 에스터기, 에테르기, 아미노기 또는및 실란기로 이루어진 군에서 선택되는 1이상의 치환기에 의해 치환된 것인 화합물.
- 청구항 1에 있어서, 상기 화학식 1이 하기 화학식 2인 것인 화합물[화학식 2]상기 화학식 2에서 R5 내지 R8은 서로 같거나 상이하고, 독립적으로 수소원자, 히드록시기, 할로겐원자, 니트릴기, 니트로기, 에스터기, 에테르기, 아미노기, 이미드기, 실란기, 티오에스터기, 탄소수 1~20개의 치환 또는 비치환의 직쇄, 분지쇄 혹은 고리형의 알킬기, 탄소수 1~20개의 치환 또는 비치환의 직쇄, 분지쇄 혹은 고리형의 알콕시기, 탄소수 1~20개의 치환 또는 비치환의 직쇄, 분지쇄 혹은 고리형의 티오알콕시기, 치환 또는 비치환된 아릴기, 혹은 치환 또는 비치환된 헤테로 아릴기이고,R5 내지 R8에 포함되는 서로 인접하지 않은 2 이상의 탄소 원자는 O, S, NH, -NRO-, SiROROO-, -CO-, -COO-, -OCO-, -OCOO-, -S-CO-, -CO-S-, -CH=CH-, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환 헤테로아릴기에 의해 연결될 수 있고, 여기서 Ro와 Roo는 서로 같거나 상이하고 독립적으로 수소, 아릴 또는 탄소수 1~12인 알킬기이며,R5 내지 R8 중 2 이상이 서로 연결되어 고리를 이루어도 좋고,n, x, y, z, A, B는 화학식 1에서 정의한 것과 같다.
- 청구항 8에 있어서, 상기 R5 내지 R8 중 어느 하나 이상이 탄소수 1~20개의 치환된 알킬기, 알콕시기 또는 티오알콕시기인 경우, 이들에 치환된 수소원자는 불소, 염소, 브롬, 요오드, 니트릴기로 이루어진 군에서 선택되는 1이상의 치환기에 의해 치환된 것인 화합물.
- 청구항 8에 있어서, 상기 R5 내지 R8 중 어느 하나 이상이 치환된 아릴기 또는 헤테로아릴기인 경우, 이들은 할로겐기, 니트릴기, 히드록시기, 알킬기, 알콕시기, 비닐기, 아세틸렌기, 티오알콕시기, 니트로기, 아미드기, 이미드기, 에스터기, 에테르기, 아미노기 또는 실란기로 이루어진 군에서 선택되는 1이상의 치환기 에 의해 치환된 것인 화합물.
- 청구항 1에 있어서, 상기 화학식 1의 화합물은 하기 화학식 R-1 내지 R-5 및, S-16 내지 S-31 및 S-34 내지 S-41 중에서 선택되는 것인 화합물:화학식 R-1 화학식R-2화학식 R-3화학식 R-4화학식 R-5화학식 S-16화학식 S-17화학식 S-18화학식 S-19화학식 S-20화학식 S-21화학식 S-22화학식 S-23화학식 S-24화학식 S-25 화학식 S-26화학식 S-27 화학식 S-28화학식 S-29화학식 S-30화학식 S-31화학식 S-34화학식 S-35화학식 S-36화학식 S-37화학식 S-38화학식 S-39화학식 S-40화학식 S-41상기 식들에 있어서, R 내지 R""'는 서로 같거나 상이하고, 독립적으로 수소원자, 산소원자, 할로겐원자, 니트릴기, 니트로기, 에스터기, 에테르기, 아미노기, 이미드기, 실란기, 티오에스터기, 탄소수 1~20개의 치환 또는 비치환의 직쇄, 분지쇄 혹은 고리형의 알킬기, 탄소수 1~20개의 치환 또는 비치환 직쇄, 분지쇄 혹은 고리형의 알콕시기, 탄소수 1~20개의 치환 또는 비치환의 직쇄, 분지쇄 혹은 고리형의 티오알콕시기, 치환 또는 비치환된 아릴기, 또한 치환 또는 비치환의 헤테로아릴기이다
- 2 이상의 전극 및 2개의 전극 사이에 배치된 1층 이상의 유기물층을 포함하는 유기 전자 소자로서, 상기 유기물층 중 1층 이상이 청구항 1 내지 청구항 16 중 어느 한 항의 화합물을 포함하는 것인 유기 전자 소자.
- 청구항 17에 있어서, 상기 유기 전자 소자는 유기 발광 소자로서, 제1 전극, 1층 이상의 유기물층 및 제2 전극을 순차적으로 적층된 형태로 포함하는 구조를 갖고, 상기 유기물층 중 1층 이상은 청구항 1 내지 청구항 16 중 어느 한 항의 화합물을 포함하는 것인 유기 전자 소자.
- 청구항 17에 있어서, 상기 유기 전자 소자는 유기 트랜지스터로서, 게이트 전극, 절연층, 1층 이상의 유기물층, 소스전극 및 드레인 전극을 포함하는 구조를 갖고, 상기 유기물층 중 1층 이상은 청구항 1 내지 청구항 16 중 어느 한 항의 화합물을 포함하는 것인 유기 전자 소자.
- 청구항 17에 있어서, 상기 유기 전자 소자는 유기 태양 전지로서, 양극, 전자도너층, 전자억셉터층 및 음극을 순차적으로 적층된 형태로 포함하는 구조를 갖고, 상기 전자도너층 및/또는 전자억셉터층은 청구항 1 내지 청구항 16 중 어느 한 항의 화합물을 포함하는 것인 유기 전자 소자.
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US (1) | US8304555B2 (ko) |
EP (1) | EP2027187B1 (ko) |
JP (1) | JP5220005B2 (ko) |
KR (1) | KR100890145B1 (ko) |
WO (1) | WO2007145482A1 (ko) |
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KR101052357B1 (ko) * | 2009-01-22 | 2011-07-27 | 한국화학연구원 | 신규한 폴리티오펜 유도체 및 이를 이용한 유기박막트랜지스터 |
KR101142206B1 (ko) * | 2009-12-03 | 2012-05-08 | 한국화학연구원 | 디티오펜-티아졸로티아졸기가 함유된 전도성 고분자, 그를 이용한 유기 광전자 소자 및 그를 채용한 유기 태양전지 |
WO2013089323A1 (ko) * | 2011-12-15 | 2013-06-20 | 경상대학교산학협력단 | 신규한 다이케토피를로피롤 중합체 및 이를 이용한 유기 전자 소자 |
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US7781673B2 (en) | 2005-07-14 | 2010-08-24 | Konarka Technologies, Inc. | Polymers with low band gaps and high charge mobility |
US20070181179A1 (en) | 2005-12-21 | 2007-08-09 | Konarka Technologies, Inc. | Tandem photovoltaic cells |
US8008421B2 (en) | 2006-10-11 | 2011-08-30 | Konarka Technologies, Inc. | Photovoltaic cell with silole-containing polymer |
US8008424B2 (en) | 2006-10-11 | 2011-08-30 | Konarka Technologies, Inc. | Photovoltaic cell with thiazole-containing polymer |
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KR100934534B1 (ko) * | 2007-11-30 | 2009-12-29 | 광주과학기술원 | 티아졸계 유기 반도체 화합물 및 이를 이용한 유기박막트랜지스터 |
CN102348737A (zh) * | 2009-03-17 | 2012-02-08 | 住友化学株式会社 | 化合物及使用该化合物的元件 |
CN102348759B (zh) * | 2009-03-17 | 2013-07-10 | 住友化学株式会社 | 组合物及使用它的元件 |
JP5347690B2 (ja) * | 2009-04-30 | 2013-11-20 | 富士ゼロックス株式会社 | 有機電界発光素子、及び表示媒体 |
KR20120101412A (ko) * | 2009-10-28 | 2012-09-13 | 유니버시티 오브 워싱톤 | 티아졸로티아졸 또는 벤조비스티아졸을 포함하는 공중합체 반도체, 또는 벤조비스옥사졸 전자수용체 소단위, 및 전자공여체 소단위, 그리고 트랜지스터와 태양전지에서 이들의 용도 |
JP5788489B2 (ja) | 2011-03-03 | 2015-09-30 | Jx日鉱日石エネルギー株式会社 | 重合体および光電変換素子 |
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JP6245761B2 (ja) * | 2014-09-18 | 2017-12-13 | Jxtgエネルギー株式会社 | 高分子化合物、有機半導体及び光電変換素子 |
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KR100914383B1 (ko) * | 2006-06-20 | 2009-08-28 | 주식회사 엘지화학 | 폴리헤테로고리 화합물, 이를 이용한 유기 전자 소자 및 이유기 전자 소자를 포함하는 전자 장치 |
KR100960492B1 (ko) * | 2007-02-13 | 2010-06-01 | 주식회사 엘지화학 | 유기 트랜지스터 및 이의 제조방법 |
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- 2007-06-15 EP EP07746940.1A patent/EP2027187B1/en active Active
- 2007-06-15 WO PCT/KR2007/002906 patent/WO2007145482A1/en active Application Filing
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101052357B1 (ko) * | 2009-01-22 | 2011-07-27 | 한국화학연구원 | 신규한 폴리티오펜 유도체 및 이를 이용한 유기박막트랜지스터 |
KR101142206B1 (ko) * | 2009-12-03 | 2012-05-08 | 한국화학연구원 | 디티오펜-티아졸로티아졸기가 함유된 전도성 고분자, 그를 이용한 유기 광전자 소자 및 그를 채용한 유기 태양전지 |
WO2013089323A1 (ko) * | 2011-12-15 | 2013-06-20 | 경상대학교산학협력단 | 신규한 다이케토피를로피롤 중합체 및 이를 이용한 유기 전자 소자 |
Also Published As
Publication number | Publication date |
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US8304555B2 (en) | 2012-11-06 |
KR100890145B1 (ko) | 2009-03-20 |
JP5220005B2 (ja) | 2013-06-26 |
EP2027187A4 (en) | 2010-08-11 |
EP2027187B1 (en) | 2016-03-30 |
JP2009541501A (ja) | 2009-11-26 |
EP2027187A1 (en) | 2009-02-25 |
WO2007145482A1 (en) | 2007-12-21 |
US20100236631A1 (en) | 2010-09-23 |
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