JP5380296B2 - ジイミド系半導体材料ならびにジイミド系半導体材料を調製および使用する方法 - Google Patents
ジイミド系半導体材料ならびにジイミド系半導体材料を調製および使用する方法 Download PDFInfo
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- JP5380296B2 JP5380296B2 JP2009537237A JP2009537237A JP5380296B2 JP 5380296 B2 JP5380296 B2 JP 5380296B2 JP 2009537237 A JP2009537237 A JP 2009537237A JP 2009537237 A JP2009537237 A JP 2009537237A JP 5380296 B2 JP5380296 B2 JP 5380296B2
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- bis
- dicarboxamide
- mmol
- alkyl
- Prior art date
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- 239000004065 semiconductor Substances 0.000 title claims description 77
- 239000000463 material Substances 0.000 title description 33
- 238000000034 method Methods 0.000 title description 23
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 title description 9
- 229910000071 diazene Inorganic materials 0.000 title description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 377
- -1 2-ethylpropyl group Chemical group 0.000 claims description 217
- 150000001875 compounds Chemical class 0.000 claims description 133
- 239000000203 mixture Substances 0.000 claims description 69
- 239000010409 thin film Substances 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 19
- 230000005669 field effect Effects 0.000 claims description 16
- 238000000151 deposition Methods 0.000 claims description 14
- 239000002131 composite material Substances 0.000 claims description 13
- 239000003989 dielectric material Substances 0.000 claims description 13
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
- 125000004051 hexyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000007639 printing Methods 0.000 claims description 9
- 238000005266 casting Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 125000000484 butyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 claims description 6
- 238000004528 spin coating Methods 0.000 claims description 6
- 125000003187 heptyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 238000007740 vapor deposition Methods 0.000 claims description 5
- 238000003618 dip coating Methods 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
- 125000000217 alkyl group Chemical group 0.000 description 95
- 125000004093 cyano group Chemical group *C#N 0.000 description 95
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 91
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 72
- 238000002360 preparation method Methods 0.000 description 72
- 239000007787 solid Substances 0.000 description 67
- 125000003118 aryl group Chemical group 0.000 description 62
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 56
- 239000000243 solution Substances 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 46
- 238000001816 cooling Methods 0.000 description 39
- 238000001914 filtration Methods 0.000 description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
- 235000019260 propionic acid Nutrition 0.000 description 36
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- 238000000921 elemental analysis Methods 0.000 description 33
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 30
- 239000012043 crude product Substances 0.000 description 28
- 125000001188 haloalkyl group Chemical group 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- 239000000741 silica gel Substances 0.000 description 27
- 238000004587 chromatography analysis Methods 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 125000001246 bromo group Chemical group Br* 0.000 description 24
- 238000010992 reflux Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000010408 film Substances 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 22
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 125000003545 alkoxy group Chemical group 0.000 description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 239000000725 suspension Substances 0.000 description 18
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 125000003342 alkenyl group Chemical group 0.000 description 14
- 229910052736 halogen Inorganic materials 0.000 description 14
- 150000002367 halogens Chemical class 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 150000003949 imides Chemical group 0.000 description 10
- 238000013508 migration Methods 0.000 description 10
- 230000005012 migration Effects 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000000547 substituted alkyl group Chemical group 0.000 description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000008186 active pharmaceutical agent Substances 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- BUZRUIZTMOKRPB-UHFFFAOYSA-N carboxycarbamic acid Chemical compound OC(=O)NC(O)=O BUZRUIZTMOKRPB-UHFFFAOYSA-N 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000002347 octyl group Chemical class [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 8
- 239000012071 phase Substances 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 7
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 239000003990 capacitor Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 229910052760 oxygen Chemical group 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- BEKHDAJTCOSDPJ-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-phenylbenzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=CC=CC=C1 BEKHDAJTCOSDPJ-UHFFFAOYSA-N 0.000 description 6
- GBGZXMZYCHOINO-UHFFFAOYSA-N 1,2,4,5-tetrafluoro-3-octyl-6-phenylbenzene Chemical group FC1=C(F)C(CCCCCCCC)=C(F)C(F)=C1C1=CC=CC=C1 GBGZXMZYCHOINO-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 238000007306 functionalization reaction Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 6
- CTYWTKRLLXDAKN-UHFFFAOYSA-N 1,2,4,5-tetrafluoro-3-(4-octylphenyl)benzene Chemical group C1=CC(CCCCCCCC)=CC=C1C1=C(F)C(F)=CC(F)=C1F CTYWTKRLLXDAKN-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000002800 charge carrier Substances 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 230000000295 complement effect Effects 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 229910001867 inorganic solvent Inorganic materials 0.000 description 5
- 239000003049 inorganic solvent Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000011669 selenium Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 4
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 4
- FKZUJUAMRZCCRX-UHFFFAOYSA-N 1-iodo-4-octylbenzene Chemical compound CCCCCCCCC1=CC=C(I)C=C1 FKZUJUAMRZCCRX-UHFFFAOYSA-N 0.000 description 4
- 0 Cc1ccc(*)cc1 Chemical compound Cc1ccc(*)cc1 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 125000003493 decenyl group Chemical group [H]C([*])=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 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 239000001301 oxygen Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- 238000004736 wide-angle X-ray diffraction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IQLIIURHJFOWCJ-UHFFFAOYSA-N 4-(2,3,4,5,6-pentafluorophenyl)aniline Chemical group C1=CC(N)=CC=C1C1=C(F)C(F)=C(F)C(F)=C1F IQLIIURHJFOWCJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
- 125000005841 biaryl group Chemical group 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000002508 contact lithography Methods 0.000 description 3
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 3
- 125000002704 decyl 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])* 0.000 description 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 239000012212 insulator Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- SCCCFNJTCDSLCY-UHFFFAOYSA-N 1-iodo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C=C1 SCCCFNJTCDSLCY-UHFFFAOYSA-N 0.000 description 2
- BNOMVHZDJIXZAA-UHFFFAOYSA-N 2-methylhexan-1-amine Chemical compound CCCCC(C)CN BNOMVHZDJIXZAA-UHFFFAOYSA-N 0.000 description 2
- PZYFAYMXLISRGL-UHFFFAOYSA-N 2-methylhexanenitrile Chemical compound CCCCC(C)C#N PZYFAYMXLISRGL-UHFFFAOYSA-N 0.000 description 2
- UFMXUNXYYDTTSW-UHFFFAOYSA-N 3,7-dimethyloct-6-en-1-amine Chemical compound NCCC(C)CCC=C(C)C UFMXUNXYYDTTSW-UHFFFAOYSA-N 0.000 description 2
- BDVBGIPKWZCKRY-UHFFFAOYSA-N 4-(2,3,5,6-tetrafluoro-4-octylphenyl)aniline Chemical group FC1=C(F)C(CCCCCCCC)=C(F)C(F)=C1C1=CC=C(N)C=C1 BDVBGIPKWZCKRY-UHFFFAOYSA-N 0.000 description 2
- ZHJCCVURMXEYJC-UHFFFAOYSA-N 4-(4-octylphenyl)aniline Chemical group C1=CC(CCCCCCCC)=CC=C1C1=CC=C(N)C=C1 ZHJCCVURMXEYJC-UHFFFAOYSA-N 0.000 description 2
- NBGBULBQONOCAX-HNNXBMFYSA-N 4-[(3s)-3,7-dimethyloct-6-enoxy]benzonitrile Chemical compound CC(C)=CCC[C@H](C)CCOC1=CC=C(C#N)C=C1 NBGBULBQONOCAX-HNNXBMFYSA-N 0.000 description 2
- DBTDKIHUSDAJJJ-AWEZNQCLSA-N 4-[(3s)-3,7-dimethyloct-6-enyl]aniline Chemical compound CC(C)=CCC[C@H](C)CCC1=CC=C(N)C=C1 DBTDKIHUSDAJJJ-AWEZNQCLSA-N 0.000 description 2
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- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
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- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
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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
- H10K85/60—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
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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]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Thin Film Transistor (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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| US60/859,761 | 2006-11-17 | ||
| PCT/US2007/024189 WO2008063609A2 (en) | 2006-11-17 | 2007-11-19 | Diimide-based semiconductor materials and methods of preparing and using the same |
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| US7569693B2 (en) * | 2006-06-12 | 2009-08-04 | Northwestern University | Naphthalene-based semiconductor materials and methods of preparing and use thereof |
| US7947837B2 (en) * | 2006-10-25 | 2011-05-24 | Polyera Corporation | Organic semiconductor materials and methods of preparing and use thereof |
| US7892454B2 (en) * | 2006-11-17 | 2011-02-22 | Polyera Corporation | Acene-based organic semiconductor materials and methods of preparing and using the same |
| CN101622253B (zh) * | 2007-01-08 | 2015-04-29 | 破立纪元有限公司 | 用于制备基于芳烃-双（二羧酰亚胺）的半导体材料的方法和用于制备它们的相关中间体 |
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| KR101638199B1 (ko) * | 2008-02-05 | 2016-07-08 | 바스프 에스이 | 페릴렌 반도체 및 이의 제조 방법 및 용도 |
| EP2240528B1 (en) * | 2008-02-05 | 2017-04-12 | Basf Se | Semiconductor materials prepared from rylene-( -acceptor) copolymers |
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| CN103764787A (zh) | 2011-08-12 | 2014-04-30 | 巴斯夫欧洲公司 | 氟化苝基半导体材料 |
| CN104221177B (zh) | 2012-02-07 | 2017-03-29 | 飞利斯有限公司 | 可光固化聚合材料及相关电子装置 |
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| US7579619B2 (en) | 2005-04-20 | 2009-08-25 | Eastman Kodak Company | N,N′-di(arylalkyl)-substituted naphthalene-based tetracarboxylic diimide compounds as n-type semiconductor materials for thin film transistors |
| US7371492B2 (en) * | 2005-07-28 | 2008-05-13 | Eastman Kodak Company | Vinyl polymer photoconductive elements |
| US7629605B2 (en) | 2005-10-31 | 2009-12-08 | Eastman Kodak Company | N-type semiconductor materials for thin film transistors |
| US7422777B2 (en) | 2005-11-22 | 2008-09-09 | Eastman Kodak Company | N,N′-dicycloalkyl-substituted naphthalene-based tetracarboxylic diimide compounds as n-type semiconductor materials for thin film transistors |
| DE102005061997A1 (de) | 2005-12-23 | 2007-07-05 | Basf Ag | Naphthalintetracarbonsäurederivate und deren Verwendung |
| WO2007093643A1 (de) | 2006-02-17 | 2007-08-23 | Basf Se | Fluorierte rylentetracarbonsäurederivate und deren verwendung |
| US7569693B2 (en) | 2006-06-12 | 2009-08-04 | Northwestern University | Naphthalene-based semiconductor materials and methods of preparing and use thereof |
| US7947837B2 (en) | 2006-10-25 | 2011-05-24 | Polyera Corporation | Organic semiconductor materials and methods of preparing and use thereof |
| US7892454B2 (en) | 2006-11-17 | 2011-02-22 | Polyera Corporation | Acene-based organic semiconductor materials and methods of preparing and using the same |
| US7804087B2 (en) | 2006-12-07 | 2010-09-28 | Eastman Kodak Company | Configurationally controlled N,N'-Dicycloalkyl-substituted naphthalene-based tetracarboxylic diimide compounds as N-type semiconductor materials for thin film transistors |
| CN101622253B (zh) | 2007-01-08 | 2015-04-29 | 破立纪元有限公司 | 用于制备基于芳烃-双（二羧酰亚胺）的半导体材料的方法和用于制备它们的相关中间体 |
| WO2008091670A2 (en) | 2007-01-24 | 2008-07-31 | Polyera Corporation | Organic semiconductor materials and precursors thereof |
-
2007
- 2007-11-19 EP EP07862121.6A patent/EP2086974B1/en not_active Not-in-force
- 2007-11-19 US US11/986,019 patent/US7902363B2/en active Active
- 2007-11-19 JP JP2009537237A patent/JP5380296B2/ja not_active Expired - Fee Related
- 2007-11-19 WO PCT/US2007/024189 patent/WO2008063609A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008063609A2 (en) | 2008-05-29 |
| JP2010510228A (ja) | 2010-04-02 |
| EP2086974B1 (en) | 2013-07-24 |
| WO2008063609A3 (en) | 2008-09-12 |
| US20080185577A1 (en) | 2008-08-07 |
| EP2086974A2 (en) | 2009-08-12 |
| US7902363B2 (en) | 2011-03-08 |
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