WO2012152598A1 - Matériaux semi-conducteurs à base de pérylène halogéné - Google Patents
Matériaux semi-conducteurs à base de pérylène halogéné Download PDFInfo
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- WO2012152598A1 WO2012152598A1 PCT/EP2012/057729 EP2012057729W WO2012152598A1 WO 2012152598 A1 WO2012152598 A1 WO 2012152598A1 EP 2012057729 W EP2012057729 W EP 2012057729W WO 2012152598 A1 WO2012152598 A1 WO 2012152598A1
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 37
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000001424 substituent group Chemical group 0.000 claims description 172
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 19
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- 238000002360 preparation method Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 229910052796 boron Inorganic materials 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 229910052723 transition metal Inorganic materials 0.000 claims description 8
- 150000003624 transition metals Chemical class 0.000 claims description 8
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 2
- -1 tetracarboxylic diimide compound Chemical class 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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- PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 description 7
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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 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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- 238000000151 deposition Methods 0.000 description 5
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
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- 239000000370 acceptor Substances 0.000 description 3
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- MLIYPCQSOXNTLJ-UHFFFAOYSA-N carbon monoxide;ruthenium dihydride;triphenylphosphane Chemical compound [RuH2].[O+]#[C-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MLIYPCQSOXNTLJ-UHFFFAOYSA-N 0.000 description 3
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- 235000019341 magnesium sulphate Nutrition 0.000 description 3
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 3
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 229910052715 tantalum Inorganic materials 0.000 description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 3
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- 125000003846 1,2-diazepinyl group Chemical group 0.000 description 2
- NAZODJSYHDYJGP-UHFFFAOYSA-N 7,18-bis[2,6-di(propan-2-yl)phenyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C(=O)C=1C2=C3C4=CC=1)C(=O)C2=CC=C3C(C=C1)=C2C4=CC=C3C(=O)N(C=4C(=CC=CC=4C(C)C)C(C)C)C(=O)C1=C23 NAZODJSYHDYJGP-UHFFFAOYSA-N 0.000 description 2
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
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- NQRACBRRMUBSDA-UHFFFAOYSA-N 17-azahexacyclo[10.9.2.02,7.03,19.08,23.015,22]tricosa-1(21),2(7),3,5,8,10,12(23),13,15(22),19-decaene-16,18-dione Chemical compound C12=CC=C3C=CC=C4C5=CC=CC=6C(=CC=C(C1=C34)C56)C(NC2=O)=O NQRACBRRMUBSDA-UHFFFAOYSA-N 0.000 description 1
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- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 150000008056 dicarboxyimides Chemical class 0.000 description 1
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001548 drop coating Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005945 imidazopyridyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000005969 isothiazolinyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000003971 isoxazolinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000005644 linolenyl group Chemical group 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 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 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000001117 oleyl 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])/C([H])=C([H])\C([H])([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 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003551 oxepanyl group Chemical group 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 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
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000005458 thianyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001583 thiepanyl group Chemical group 0.000 description 1
- 125000003777 thiepinyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Definitions
- Organic semiconducting materials can be used in electronic devices such as organic photo- voltaic (OPV) cells, organic field-effect transistors (OFETs) and organic light emitting diodes (OLEDs).
- OCV organic photo- voltaic
- OFETs organic field-effect transistors
- OLEDs organic light emitting diodes
- the organic semiconducting material-based devices show high charge carrier mobility and high stability, in particular towards oxi- dation, under ambient conditions.
- the organic semiconducting materials are compatible with liquid processing techniques as liquid processing techniques are convenient from the point of proc- essability, and thus allow the production of low cost organic semiconducting material-based electronic devices.
- liquid processing techniques are also compatible with plastic substrates, and thus allow the production of light weight and flexible organic semiconducting material-based electronic devices.
- Perylene bisimide-based organic semiconducting materials suitable for use in electronic devices are known in the art.
- Ar 1 is a first aromatic core and is a divalent, trivalent or tetravalent radical of a long list of formulae, including
- EC is a first end capping group and is a monovalent radical of a long list of formulae, n is an integer of 2 to 4
- Z is NH or CH 2
- OFET organic thin film transistor
- the organic semiconductor film is formed of pentacene.
- the organic acceptor film is formed of at least one electron withdrawing material selected from a long list of compounds, including N,N'-bis(di-feri-butyphenyl)-3,4,9,10-perylenedicarboximide.
- US 7,326,956 B2 describes a thin film transitor comprising a layer of organic semiconductor material comprising tetracarboxylic diimide perylene-based compound having attached to each of the imide nitrogen atoms a carbocyclic or heterocyclic aromatic ring system substituted with one or more fluorine containing groups.
- the fluorine-containing N,N'-diaryl perylene-based tetracarboxylic diimide compound is represented by the following structure:
- a 1 and A 2 are independently carbocyclic and/or heterocyclic aromatic ring systems comprising at least one aromatic ring in which one or more hydrogen atoms are substituted with at least one fluorine-containing group.
- the perylene nucleus can be optionally substituted with up to eight independently selected X groups, wherein n is an integer from 0 to 8.
- the X substituent groups on the perylene can include a long list of substituents, including halogens such as fluorine or chlorine.
- each R 1 to R 8 can be independently selected from H, an electron-withdrawing substituent and a moiety comprising such substituent.
- Electron-withdrawing substitutents include a long list of substituents, including cyano.
- R 9 and R 10 are independently selected from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, polycyclic aryl and/or substi- tuted polycyclic aryl moieties.
- WO 2005/124453 describes perylenetetracarboxylic diimide charge-transfer materials, for example a perylenetetracarboxylic diimide charge-transfer material having formula
- Y in each instance can be independently selected from H, CN, acceptors, donors and a polymerizable group; and X in each instance can be independently selected from a large group of listed compounds.
- WO 2008/063609 describes a compound having the following formula
- A, B, I, D, E, F, G and H are independently selected from a group of substituents, including, CH and CR a , wherein R a can be selected from a list of substituents, including halogen.
- A, B, I, D, E, F, G and H can be independently CH, C-Br or C-CN.
- WO 2009/098252 describes semiconducting compounds having formula
- R 1 and R 2 at each occurrence independently are selected from a large list of groups, including H, Ci-30-alkyl and C2-3o-alkenyl; and R 3 , R 4 , R 5 and R 6 are independently H or an electron-withdrawing group.
- R 3 , R 4 , R 5 and R 6 can be independently from each other H, F, CI, Br, I or CN.
- WO 2009/144205 describes bispolycyclic rylene-based semiconducting compounds, which can be prepared from a compound of formula
- LG is a leaving group, including CI, Br or I,
- ⁇ -1 can be
- A, B, I, D, E, F, G and H are independently selected from a group of substituents, in eluding, CH and CR a , wherein R a can be selected from a list of substituents, including halogen.
- the object is solved by the compound of claim 1 , the process of claim 5, and the electronic de- vice of claim 6.
- the perylene-based semiconducting compound of the present invention is of formula 1
- R 1 and R 2 are independently from each other selected from the group consisting of H, Ci-30-alkyl optionally substituted with 1 to 30 substituents R a , C2-3o-alkenyl optionally substituted with
- -O-COR 3 -S-Ci-3o-alkyl optionally substituted with 1 to 30 substituents R', -SO 2 -Ci- 30 -alkyl optionally substituted with 1 to 30 substituents R', -NH 2 , -NHR 3 , -NR 3 R 4 , -[NR 3 R 4 R 5 ] + , -NH-COR 3 , -COOH, -COOR 3 , -CONH 2 , -CONHR 3 , -CONR 3 R 4 , -CO-H, -COR 3 , Ci-30-alkyl optionally substituted with 1 to 30 substituents R', C 2- 3o-alkenyl optionally substituted with 1 to 30 substituents R', C 2- 3o-alkynyl optionally substituted with 1 to 30 substituents R',
- R 3 , R 4 and R 5 at each occurrence are independently from each other selected from the group consisting of Ci-30-alkyl optionally substituted with 1 to 30 substituents R', C 2- 3o-alkenyl optionally substituted with 1 to 30 substituents R', C 2- 3o-alkynyl optionally substituted with 1 to 30 substituents R', C3-io-cycloalkyl optionally substituted with 1 to
- R 6 , R 7 and R 8 at each occurrence are independently from each other selected from the group consisting of Ci-30-alkyl, C 2- 3o-alkenyl, C 2- 3o-alkynyl, C3-io-cycloalkyl, C5-io-cycloalkenyl, 3-14 membered cycloheteroalkyl, C6-i4-aryl and 5-14 membered heteroaryl,
- X is -CI, -Br or -I.
- Ci-io-alkyl and Ci-30-alkyl can be branched or unbranched.
- Examples of Ci-10-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, fert-butyl, n-pentyl, neopentyl, isopentyl, n-(1 -ethyl)propyl, n-hexyl, n-heptyl, n-octyl, n-(2-ethyl)hexyl, n-nonyl and n-decyl.
- C3-8-alkyl examples include n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, fert-butyl, n-pentyl, neopentyl, isopentyl, n-(1 -ethyl)propyl, n-hexyl, n-heptyl, n-octyl and n-(2-ethyl)hexyl.
- Ci-30-alkyl examples are Ci-10-alkyl, and n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and n-icosyl (C 20 ), n-docosyl (C 22 ), n-tetracosyl (C 2 4), n-hexacosyl (C 2 6), n-octacosyl (C 2 s) and n-triacontyl (C30).
- C3- 2 5-alkyl branched at the C attached to the N of formula I are isopropyl, sec-butyl, n-(1 -methyl)propyl, n-(1 - ethyl)propyl, n-(1 -methyl)butyl, n-(1 -ethyl)butyl, n-(1 -propyl)butyl, n-(1 -methyl)pentyl, n-(1 - ethyl)pentyl, n-(1 -propyl)pentyl, n-(1 -butyl)pentyl, n-(1 -butyl)hexyl, n-(1 -pentyl)hexyl, n-(1 -pentyl)hexyl, n-(1 - hexyl)heptyl, n-(1 -heptyl)oc
- C2-3o-alkenyl can be branched or unbranched.
- Examples of C2-3o-alkenyl are vinyl, propenyl, cis- 2-butenyl, frans-2-butenyl, 3-butenyl, c/s-2-pentenyl, frans-2-pentenyl, c/s-3-pentenyl, trans- 3-pentenyl, 4-pentenyl, 2-methyl-3-butenyl, hexenyl, heptenyl, octenyl, nonenyl and docenyl, linoleyl (ds), linolenyl (Cis), oleyl (Cis), arachidonyl (C20), and erucyl (C22).
- C2-3o-alkynyl can be branched or unbranched.
- Examples of C2-3o-alkynyl are ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl and decynyl, undecynyl, do- decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptade- cynyl, octadecynyl, nonadecynyl and icosynyl (C20).
- C3-io-cycloalkyl are preferably monocyclic C3-io-cycloalkyls such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, but include also polycyclic
- C3-io-cycloalkyls such as decalinyl, norbornyl and adamantyl.
- Cs-io-cycloalkenyl are preferably monocyclic Cs-io-cycloalkenyls such as cyclopen- tenyl, cyclohexenyl, cyclohexadienyl and cycloheptatrienyl, but include also polycyclic
- Examples of 3-14 membered cycloheteroalkyi are monocyclic 3-8 membered cycloheteroalkyi and polycyclic, for example bicyclic 7-12 membered cycloheteroalkyi.
- Examples of monocyclic 3-8 membered cycloheteroalkyi are monocyclic 5 membered cycloheteroalkyi containing one heteroatom such as pyrrolidinyl, 1 -pyrrolinyl, 2-pyrrolinyl, 3-pyrrolinyl, tetrahydrofuryl, 2,3-dihydrofuryl, tetrahydrothiophenyl and 2,3-dihydrothiophenyl, monocyclic
- cycloheteroalkyi containing one heteroatom such as piperidyl, piperidino, tetrahy- dropyranyl, pyranyl, thianyl and thiopyranyl, monocyclic 6 membered cycloheteroalkyi containing two heteroatoms such as piperazinyl, morpholinyl and morpholino and thiazinyl, monocyclic 7 membered cycloheteroalkyi containing one hereoatom such as azepanyl, azepinyl, oxepanyl, thiepanyl, thiapanyl, thiepinyl, and monocyclic 7 membered cycloheteroalkyi containing two hereoatom such as 1 ,2-diazepinyl and 1 ,3-thiazepinyl.
- C6-i4-aryl can be monocyclic or polycyclic.
- Examples of C6-i4-aryl are monocyclic C6-aryl such as phenyl, bicyclic Cg-io-aryl such as 1 -naphthyl, 2-naphthyl, indenyl, indanyl and tetrahy- dronaphthyl, and tricyclic Ci2-i4-aryl such as anthryl, phenanthryl, fluorenyl and s-indacenyl.
- 5-14 membered heteroaryl can be monocyclic 5-8 membered heteroaryl, or polycyclic 7-14 membered heteroaryl, for example bicyclic 7-12 membered or tricyclic 9-14 membered heteroaryl.
- monocyclic 5-8 membered heteroaryl examples include monocyclic 5 membered heteroaryl con- taining one heteroatom such as pyrrolyl, furyl and thiophenyl, monocyclic 5 membered heteroaryl containing two heteroatoms such as imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, monocyclic 5 membered heteroaryl containing three heteroatoms such as
- 1 ,2,3-triazolyl, 1 ,2,4-triazolyl and oxadiazolyl monocyclic 5 membered heteroaryl containing four heteroatoms such as tetrazolyl, monocyclic 6 membered heteroaryl containing one heteroa- torn such as pyridyl, monocyclic 6 membered heteroaryl containing two heteroatoms such as pyrazinyl, pyrimidinyl and pyridazinyl, monocyclic 6 membered heteroaryl containing three heteroatoms such as 1 ,2,3-triazinyl, 1 ,2,4-triazinyl and 1 ,3,5-triazinyl, monocyclic 7 membered heteroaryl containing one heteroatom such as azepinyl, and monocyclic 7 membered heteroaryl containing two heteroatoms such as 1 ,2-diazepinyl.
- monocyclic 5 membered heteroaryl containing four heteroatoms such as
- bicyclic 7-12 membered heteroaryl examples include bicyclic 9 membered heteroaryl containing one heteroatom such as indolyl, isoindolyl, indolizinyl, indolinyl, benzofuryl, isobenzofuryl, ben- zothiophenyl and isobenzothiophenyl, bicyclic 9 membered heteroaryl containing two heteroatoms such as indazolyl, benzimidazolyl, benzimidazolinyl, benzoxazolyl, benzisooxazolyl, benzthiazolyl, benzisothiazolyl, furopyridyl and thienopyridyl, bicyclic 9 membered heteroaryl containing three heteroatoms such as benzotriazolyl, benzoxadiazolyl, oxazolopyridyl, isooxa- zolopyridyl, thiazolopyridyl, iso
- tricyclic 9-14 membered heteroaryls examples include dibenzofuryl, acridinyl, phenoxazinyl, 7H- cyclopenta[1 ,2-b:3,4-b']dithiophenyl and 4H-cyclopenta[2,1 -b:3,4-b']dithiophenyl.
- halogen examples are -F, -CI, -Br and -I.
- Ci-30-alkoxy are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, fert-butoxy, n-pentoxy, neopentoxy, isopentoxy, hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, n-dodecoxy, n-tridecoxy, n-tetradecoxy, n-pentadecoxy, n-hexadecoxy, n-heptadecoxy, n-octadecoxy and n-nonadecoxy.
- Examples of C2-5-alkylene are ethylene, propylene, butylene and pentylene.
- C2-5-alkylene are ethylene, prop
- R 1 and R 2 are independently from each other selected from the group consisting of H, Ci-30-alkyl optionally substituted with 1 to 30 substituents R a , C2-3o-alkenyl optionally substituted with 1 to 30 substituents R a , C3-io-cycloalkyl optionally substituted with 1 to 10 substituents R b , and C6-i4-aryl optionally substituted with 1 to 8 substituents R c , wherein
- R 3 , R 4 and R 5 at each occurrence are independently from each other selected from the group consisting of Ci-30-alkyl optionally substituted with 1 to 30 substituents R', C2-3o-alkenyl optionally substituted with 1 to 30 substituents R', C3-io-cycloalkyl optionally substituted with 1 to 10 substituents R", and C6-i4-aryl optionally substituted with 1 to 8 substituents R iH ,
- R 6 , R 7 and R 8 at each occurrence are independently from each other selected from the group consisting of Ci -3 o-alkyl, C 2-3 o-alkenyl, C 3- io-cycloalkyl, and C6-i4-aryl, and
- X is -CI, -Br or I.
- R 1 and R 2 are independently from each other Ci -3 o-alkyl optionally substituted with 1 to 30 substituents R a , wherein
- R 3 , R 4 and R 5 at each occurrence are independently from each other selected from the group consisting of Ci-30-alkyl optionally substituted with 1 to 30 substituents R', C2-3o-alkenyl optionally substituted with 1 to 30 substituents R', C3-io-cycloalkyl optionally substituted with 1 to 10 substituents R", and C6-i4-aryl optionally substituted with 1 to 8 substituents R iH ,
- R 6 , R 7 and R 8 at each occurrence are independently from each other selected from the group consisting of Ci -3 o-alkyl, C 2-3 o-alkenyl, C 3- io-cycloalkyl, and C6-i4-aryl, and
- X is -CI, -Br or -I. Most preferably,
- R 1 and R 2 are independently from each other C 3-2 5-alkyl branched at the C attached to the N of formula 1 and
- X is -CI, -Br or -I. Particular preferred are the compounds of formulae
- R 1 and R 2 are as defined above, which process comprises the steps of
- R 1 and R 2 are as defined above, and L is a linking group
- L is preferably C2-5-alkylene, which can be optionally substituted with 1 to 6 Ci-10-alkyl groups. More preferably L is ethylene or propylene and is substituted with 2 to 4 methyl groups.
- the transition metal-containing catalyst can be an iridium-containing catalyst such as
- the first step can be performed in the presence of a base such as di-feri-butylbipyridine. If the transition metal- containing catalyst is an iridium-containing catalyst, the first step is usually performed in a suitable organic solvent such as tetrahydrofuran or 1 ,4-dioxane. If the transition metal-containing catalyst is an iridium-containing catalyst, the first step is usually performed at elevated temperatures, such as at temperatures from 60 to 1 10 °C. In principal, if the transition metal-containing catalyst is an iridium-containing catalyst, the first step can be performed in analogy to the method described by C. W. Liskey; X. Liao; J. F.
- the first step is usu- ally performed in a suitable organic solvent such as toluene, pinacolone and mesitylene or mixtures thereof. If the transition metal-containing catalyst is ruthenium-containing catalyst, the first step is usually performed at elevated temperatures, such as at temperatures from 120 to 160 °C.
- the Cl-source source can be Cu(ll)Cl2.
- the Br-source source can be Cu(ll)Br2.
- the l-source source can be Nal in combination with chloroamine T.
- the second step is usually performed in a suitable solvent such as water, methanol, THF and dioxane, or mixtures thereof.
- the second step is usually performed at elevated temperatures, such as at temperatures from 40 to 140 °C.
- the second step is preferably performed at elevated temperatures, such as at temperatures from 80 to 140 °C.
- the second step is preferably performed at elevated temperatures, such as at temperatures from 40 to 80 °C.
- the compounds of formulae (4) and (1 ) can be isolated by methods known in the art, such as column chromatography.
- the compound of formula (2) can be obtained by methods known in the art, for example as described in the subsection titled "Synthesis" of F. Wurthner, Chem. Commun., 2004, 1564-1579.
- an electronic device comprising the compound of formula (1 ) as semiconducting material.
- the electronic device is an organic field effect transistor (OFET).
- an organic field effect transistor comprises a dielectric layer, a semiconducting layer and a substrate.
- an organic field effect transistor usually comprises a gate electrode and source/drain electrodes.
- An organic field effect transistor can have various designs. The most common design of an organic field-effect transistor is the bottom-gate design. Examples of bottom-gate designs are shown in Figures 1.
- top-gate design Another design of an organic field-effect transistor is the top-gate design. Examples of top-gate designs are shown in Figure 2.
- the semiconducting layer comprises the semiconducting material of the present invention.
- the semiconducting layer can have a thickness of 5 to 500 nm, preferably of 10 to 100 nm, more preferably of 20 to 50 nm.
- the dielectric layer comprises a dielectric material.
- the dielectric material can be silicon dioxide, or, an organic polymer such as polystyrene (PS), poly(methylmethacrylate) (PMMA), poly(4-vinylphenol) (PVP), polyvinyl alcohol) (PVA), benzocyclobutene (BCB), or polyimide (PI).
- PS polystyrene
- PMMA poly(methylmethacrylate)
- PVP poly(4-vinylphenol)
- PVA polyvinyl alcohol
- BCB benzocyclobutene
- PI polyimide
- the dielectric layer can have a thickness of 10 to 2000 nm, preferably of 50 to 1000 nm, more preferably of 100 to 800 nm
- the source/drain electrodes can be made from any suitable source/drain material, for example gold (Au) or tantalum (Ta).
- the source/drain electrodes can have a thickness of 1 to 100 nm, preferably from 5 to 50 nm.
- the gate electrode can be made from any suitable gate material such as highly doped silicon, aluminium (Al), tungsten (W), indium tin oxide, gold (Au) and/or tantalum (Ta).
- the gate elec- trode can have a thickness of 1 to 200 nm, preferably from 5 to 100 nm.
- the substrate can be any suitable substrate such as glass, or a plastic substrate such as poly- ethersulfone, polycarbonate, polysulfone, polyethylene terephthalate (PET) and polyethylene naphthalate (PEN).
- a combination of the gate electrode and the dielectric layer can also function as substrate.
- the organic field effect transistor can be prepared by methods known in the art.
- a bottom-gate organic field effect transistor can be prepared as follows:
- the gate electrode can be formed by depositing the gate material, for example highly doped silicon, on one side of the dielectric layer made of a suitable dielectric material, for example si- licium dioxide.
- the other side of the dielectric layer can be optionally treated with a suitable reagent, for example with hexamethyldisilazane (HMDS).
- Source/drain electrodes can be deposited on this side (the side which is optionally treated with a suitable reagent) of the dielectric layer for example by vapour deposition of a suitable source/drain material, for example tantalum (Ta) and/or gold (Au).
- the source/drain electrodes can then be covered with the semiconducting layer by solution processing, for example drop coating, a solution of the semiconducting material of the present invention in s suitable solvent, for example in chloroform. Also part of the invention is the use of the compound of formula (1 ) as semiconducting material.
- the advantage of the semiconducting materials of the present invention is the high solubility of these materials in solvents suitable for solution processing.
- the semiconducting materials of the present invention show acceptable to high charge carrier mobility.
- the semiconducting materials are stable, in particular towards oxidation, under ambient conditions.
- A/,A/'-Bis(1 -heptyloctyl) perylene-3,4:9,10-tetracarboxylic acid bisimide (2b) (100 mg, 0.12 mmol) and bispinacolonediboronate (3a) (250 mg, 0.99 mmol) are mixed together and dissolved in 1 ml. anhydrous mesitylene and 1 ml. anhydrous pinacolone. Argon is bubbled through the solution for 30 minutes.
- RuH2(CO)(PPh3)3 23 mg, 0,03 mmol
- thermoly grown silicon dioxide (thickness: 200 nm) is used as dielectric layer.
- the gate electrode is formed by depositing highly doped silicon on one side of the dielectric layer.
- the other side of the dielectric layer is treated with hexamethyldisilazane (HMDS) by vapour deposition of hexamethyldisilazane.
- HMDS hexamethyldisilazane
- the contact angle of the surface of the HMPS-treated side of the dielectric layer is 93.2 ⁇ 1.3°.
- Source/drain electrodes (Ta (thickness: 10 nm) covered by Au (thick- ness: 40 nm)) are deposited on the HMPS-treated side of the dielectric layer by vapour deposition.
- the source/drain electrodes are then covered with the semiconducting layer (thickness: ca.
- the drain current ISD [A] in relation to the gate voltage VSG [V] (top transfer curve) and the drain current ISD 0 5 [ ⁇ ° 5 ] in relation to the gate voltage VSG [V] (bottom transfer curve) for the bottom- gate organic field effect transistor of example 6 comprising compound 1c as semiconducting material at a drain voltage VSD of 100 V is determined in a nitrogen filled glove box (O2 content: 0.1 ppm, H 2 0 content: 0.0 ppm, pressure: 1 120 Pa, temperature: 17 °C) using a Keithley 4200 machine is shown. The results are shown in Figure 4.
- the drain current ISD in relation to the drain voltage VSD (output curve) for the bottom-gate organic field effect transistor of example 6 comprising compound 1c as semiconducting material at a gate voltage VSG of 100 V (first and top curve), 90 V (second curve), 80 V (third curve), 70 V (fourth curve) and 0 V (fifth and bottom curve) is determined in a nitrogen filled glove box (O2 content: 0.1 ppm, H2O content: 0.0 ppm, pressure: 1 120 Pa, temperature: 17 °C) using a Keithley 4200 machine is shown. The results are shown in Figure 5.
- drain current ISD [A] in relation to the gate voltage VSG [V] (top transfer curve) and the drain current ISD 0 5 [ ⁇ ° 5 ] in relation to the gate voltage VSG [V] (bottom transfer curve) for the bottom- gate, organic field effect transistor of example 6 comprising compound 1 b as semiconducting material at a drain voltage VSD of 100 V is determined in a nitrogen filled glove box (O2 content: 0.1 ppm, H 2 0 content: 0.0 ppm, pressure: 1 120 Pa, temperature: 17 °C) using a Keithley 4200 machine is shown. The results are shown in Figure 6.
- the drain current ISD in relation to the drain voltage VSD (output curve) for the bottom-gate organic field effect transistor of example 6 comprising compound 1 b as semiconducting material at a gate voltage VSG of 100 V (first and top curve), 90 V (second curve), 80 V (third curve) and 0 V (fourth and bottom curve) is determined in a nitrogen filled glove box (O2 content: 0.1 ppm, H2O content: 0.0 ppm, pressure: 1 120 Pa, temperature: 17 °C) using a Keithley 4200 machine is shown. The results are shown in Figure 7.
- the average values and the 90% confidence interval (in parentheses) of the charge carrier mobilities ⁇ 53 ⁇ [cmWs], the ION/IOFF ratios and the switch-on voltages Vso [V] for the bottom-gate organic field effect transistors of example 6 comprising compound 1 b, respectively, 1c, as semi- conducting material are given in table 1.
- the switch-on voltage Vso [V] is the gate voltage VSG [V] where the drain current ISD [A] starts to increase (out of the off-state).
- A/,A/'-Bis-octyl-2,5,8,1 1 -tetrakis[4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-y]perylene-3,4:9,10- tetracarboxylic acid bisimide (0.68 mg, 0.61 mmol) and copper(ll) bromide (1 ,62 g, 7.3 mmol) are suspended in a mixture of dioxane (10 mL), methanol (3 ml) and water (3 ml) and heated at 120°C for 12 hours. The reaction mixture is then poured into HCI (1 .0 M) and the solid so obtained filtered.
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Abstract
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EP12717702.0A EP2707455A1 (fr) | 2011-05-11 | 2012-04-27 | Matériaux semi-conducteurs à base de pérylène halogéné |
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Cited By (4)
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US9583719B2 (en) | 2011-08-12 | 2017-02-28 | Basf Se | Carbazolocarbazol-bis(dicarboximides) and their use as semiconductors |
WO2019170481A1 (fr) | 2018-03-07 | 2019-09-12 | Basf Se | Procédé de formation de motifs pour préparer des transistors à effet de champ organiques à grille supérieure et à contact inférieur |
WO2019170719A1 (fr) | 2018-03-08 | 2019-09-12 | Basf Se | Transistor à effet de champ organique comprenant des nanotubes de carbone simple paroi semi-conducteurs et un matériau semi-conducteur organique |
WO2020001865A1 (fr) | 2018-06-26 | 2020-01-02 | Basf Se | Polymère à base d'éther vinylique utilisé comme diélectrique |
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WO2018185599A1 (fr) * | 2017-04-04 | 2018-10-11 | 株式会社半導体エネルギー研究所 | Procédé d'analyse d'éléments à semi-conducteur organique |
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US9583719B2 (en) | 2011-08-12 | 2017-02-28 | Basf Se | Carbazolocarbazol-bis(dicarboximides) and their use as semiconductors |
WO2019170481A1 (fr) | 2018-03-07 | 2019-09-12 | Basf Se | Procédé de formation de motifs pour préparer des transistors à effet de champ organiques à grille supérieure et à contact inférieur |
US11296290B2 (en) | 2018-03-07 | 2022-04-05 | Clap Co., Ltd. | Patterning method for preparing top-gate, bottom-contact organic field effect transistors |
US11690236B2 (en) | 2018-03-07 | 2023-06-27 | Clap Co., Ltd. | Patterning method for preparing top-gate, bottom-contact organic field effect transistors |
WO2019170719A1 (fr) | 2018-03-08 | 2019-09-12 | Basf Se | Transistor à effet de champ organique comprenant des nanotubes de carbone simple paroi semi-conducteurs et un matériau semi-conducteur organique |
WO2020001865A1 (fr) | 2018-06-26 | 2020-01-02 | Basf Se | Polymère à base d'éther vinylique utilisé comme diélectrique |
Also Published As
Publication number | Publication date |
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KR20140021014A (ko) | 2014-02-19 |
JP2014519490A (ja) | 2014-08-14 |
CN103732720B (zh) | 2016-02-17 |
JP5744323B2 (ja) | 2015-07-08 |
EP2707455A1 (fr) | 2014-03-19 |
TWI598349B (zh) | 2017-09-11 |
CN103732720A (zh) | 2014-04-16 |
TW201302748A (zh) | 2013-01-16 |
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