KR101443189B1 - 신규한 다이케토피롤로피롤 중합체 및 이를 이용한 유기 전자 소자 - Google Patents
신규한 다이케토피롤로피롤 중합체 및 이를 이용한 유기 전자 소자 Download PDFInfo
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- KR101443189B1 KR101443189B1 KR1020120145234A KR20120145234A KR101443189B1 KR 101443189 B1 KR101443189 B1 KR 101443189B1 KR 1020120145234 A KR1020120145234 A KR 1020120145234A KR 20120145234 A KR20120145234 A KR 20120145234A KR 101443189 B1 KR101443189 B1 KR 101443189B1
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- organic semiconductor
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- 229920000642 polymer Polymers 0.000 title claims abstract description 37
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000004065 semiconductor Substances 0.000 claims abstract description 71
- 239000010409 thin film Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- -1 hydroxy, amino Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
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- 0 CC(*)CN(C(c1ccc(C2=CC[C@](C(C#N)=CC(S)=CC=CC)S2)[s]1)=C(C1=C(c2ccc(**)[s]2)N2CC(*)*)C2=O)C1=O Chemical compound CC(*)CN(C(c1ccc(C2=CC[C@](C(C#N)=CC(S)=CC=CC)S2)[s]1)=C(C1=C(c2ccc(**)[s]2)N2CC(*)*)C2=O)C1=O 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
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- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
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- OUEXMRWLJGPETN-UHFFFAOYSA-N C[Sn](C1=CC=C([Se]1)C=CC=1[Se]C(=CC1)[Sn](C)(C)C)(C)C Chemical compound C[Sn](C1=CC=C([Se]1)C=CC=1[Se]C(=CC1)[Sn](C)(C)C)(C)C OUEXMRWLJGPETN-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
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- OXGIFJRJHHAWIW-UHFFFAOYSA-N 2-[(E)-2-selenophen-2-ylethenyl]selenophene Chemical compound [Se]1C(=CC=C1)C=CC=1[Se]C=CC1 OXGIFJRJHHAWIW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
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- 239000004033 plastic Substances 0.000 description 2
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 2
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- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VCAVNMJASGWLMY-UHFFFAOYSA-N 2,5-bis(2-dodecylhexadecyl)-1,4-dithiophen-2-ylpyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C(CCCCCCCCCCC)C(CN1C(C2=C(N(C(C2=C1C=1SC=CC1)=O)CC(CCCCCCCCCCCCCC)CCCCCCCCCCCC)C=1SC=CC1)=O)CCCCCCCCCCCCCC VCAVNMJASGWLMY-UHFFFAOYSA-N 0.000 description 1
- DEMBLPGWNXUBIQ-UHFFFAOYSA-N 2-dodecylhexadecan-1-ol Chemical compound CCCCCCCCCCCCCCC(CO)CCCCCCCCCCCC DEMBLPGWNXUBIQ-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
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- MPLZCMWJOGIPKC-UHFFFAOYSA-N Bc1ccc(C(N(CC(C)C)C(C2=C(c3ccc(B)[s]3)N3CC(C)C)=O)=C2C3=O)[s]1 Chemical compound Bc1ccc(C(N(CC(C)C)C(C2=C(c3ccc(B)[s]3)N3CC(C)C)=O)=C2C3=O)[s]1 MPLZCMWJOGIPKC-UHFFFAOYSA-N 0.000 description 1
- GKSPLPVZHDHUID-UHFFFAOYSA-N BrC1=CC=C(S1)C=1N(C(C2=CN(C(C21)=O)CC(CCCCCCCCCCCCCC)CCCCCCCCCCCC)=O)CC(CCCCCCCCCCCCCC)CCCCCCCCCCCC Chemical compound BrC1=CC=C(S1)C=1N(C(C2=CN(C(C21)=O)CC(CCCCCCCCCCCCCC)CCCCCCCCCCCC)=O)CC(CCCCCCCCCCCCCC)CCCCCCCCCCCC GKSPLPVZHDHUID-UHFFFAOYSA-N 0.000 description 1
- YBDUTDUOWRZIFI-UHFFFAOYSA-N BrCC(CCCCCCCCCCCC)CCCCCCCCCCCCCC.BrCC(CCCCCCCCCCCC)CCCCCCCCCCCCCC Chemical compound BrCC(CCCCCCCCCCCC)CCCCCCCCCCCCCC.BrCC(CCCCCCCCCCCC)CCCCCCCCCCCCCC YBDUTDUOWRZIFI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FXALPCMILKZBBM-UHFFFAOYSA-N C1=CNC(=O)C2=C1C(=O)NC2 Chemical compound C1=CNC(=O)C2=C1C(=O)NC2 FXALPCMILKZBBM-UHFFFAOYSA-N 0.000 description 1
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- WAJDEQBKZBXJMO-BPLSXZKWSA-N C[SnH](C)c1ccc(/C=C/c([s]2)ccc2[Sn](C)(C)C)[s]1 Chemical compound C[SnH](C)c1ccc(/C=C/c([s]2)ccc2[Sn](C)(C)C)[s]1 WAJDEQBKZBXJMO-BPLSXZKWSA-N 0.000 description 1
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- 229940126062 Compound A Drugs 0.000 description 1
- PAEYAKGINDQUCT-UHFFFAOYSA-N Ethyl 2-pyrrolecarboxylate Chemical compound CCOC(=O)C1=CC=CN1 PAEYAKGINDQUCT-UHFFFAOYSA-N 0.000 description 1
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- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 238000007707 calorimetry Methods 0.000 description 1
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- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
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- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
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- 150000007523 nucleic acids Chemical class 0.000 description 1
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- 108020004707 nucleic acids Proteins 0.000 description 1
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- BHDAVTMCXVRKAS-UHFFFAOYSA-N pyrrolidine-3,4-dione Chemical compound O=C1CNCC1=O BHDAVTMCXVRKAS-UHFFFAOYSA-N 0.000 description 1
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- 238000007650 screen-printing Methods 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- AGBORNIRMFZCGC-UHFFFAOYSA-N selenophene-2-carbaldehyde Chemical compound O=CC1=CC=C[se]1 AGBORNIRMFZCGC-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 230000002195 synergetic effect Effects 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- 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
- C08G61/124—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 nitrogen atom in the ring
-
- 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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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- 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]
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- H—ELECTRICITY
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