WO2005043630A1 - 有機薄膜トランジスタ - Google Patents
有機薄膜トランジスタ Download PDFInfo
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- WO2005043630A1 WO2005043630A1 PCT/JP2004/016293 JP2004016293W WO2005043630A1 WO 2005043630 A1 WO2005043630 A1 WO 2005043630A1 JP 2004016293 W JP2004016293 W JP 2004016293W WO 2005043630 A1 WO2005043630 A1 WO 2005043630A1
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- carbon atoms
- film transistor
- thin film
- organic thin
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- 239000010409 thin film Substances 0.000 title claims abstract description 59
- -1 nitrogen-containing heterocyclic compound Chemical class 0.000 claims abstract description 80
- 239000004065 semiconductor Substances 0.000 claims abstract description 31
- 239000000758 substrate Substances 0.000 claims abstract description 27
- 125000001424 substituent group Chemical group 0.000 claims description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000012212 insulator Substances 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 101
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 48
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 34
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 21
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 18
- 239000010408 film Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- 125000003342 alkenyl group Chemical group 0.000 description 15
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 15
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 12
- 239000010931 gold Substances 0.000 description 12
- 150000003852 triazoles Chemical class 0.000 description 12
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 11
- 230000005669 field effect Effects 0.000 description 11
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000010586 diagram Methods 0.000 description 8
- 238000001771 vacuum deposition Methods 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 125000005013 aryl ether group Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000003172 aldehyde group Chemical group 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 125000005401 siloxanyl group Chemical group 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229910052581 Si3N4 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001350 alkyl halides Chemical group 0.000 description 3
- 229910021417 amorphous silicon Inorganic materials 0.000 description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002605 large molecules Chemical class 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 3
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 150000004832 aryl thioethers Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 229910002115 bismuth titanate Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 2
- 239000001989 lithium alloy Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000010955 niobium Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 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 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- IDQBJILTOGBZCR-UHFFFAOYSA-N 1-butoxypropan-1-ol Chemical compound CCCCOC(O)CC IDQBJILTOGBZCR-UHFFFAOYSA-N 0.000 description 1
- JLBXCKSMESLGTJ-UHFFFAOYSA-N 1-ethoxypropan-1-ol Chemical compound CCOC(O)CC JLBXCKSMESLGTJ-UHFFFAOYSA-N 0.000 description 1
- SVIZHJGLXNKEHP-UHFFFAOYSA-N 1-heptoxyethanol Chemical compound CCCCCCCOC(C)O SVIZHJGLXNKEHP-UHFFFAOYSA-N 0.000 description 1
- OYTCWIBDTYOGCL-UHFFFAOYSA-N 1-heptoxypropan-1-ol Chemical compound CCCCCCCOC(O)CC OYTCWIBDTYOGCL-UHFFFAOYSA-N 0.000 description 1
- QACWCDDNEROCPA-UHFFFAOYSA-N 1-pentoxyethanol Chemical compound CCCCCOC(C)O QACWCDDNEROCPA-UHFFFAOYSA-N 0.000 description 1
- HRDPFSGJSQGPIW-UHFFFAOYSA-N 1-pentoxypropan-1-ol Chemical compound CCCCCOC(O)CC HRDPFSGJSQGPIW-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000257465 Echinoidea Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- 229910000733 Li alloy Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002377 Polythiazyl Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- PQCCZSBUXOQGIU-UHFFFAOYSA-N [La].[Pb] Chemical compound [La].[Pb] PQCCZSBUXOQGIU-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- VNSWULZVUKFJHK-UHFFFAOYSA-N [Sr].[Bi] Chemical compound [Sr].[Bi] VNSWULZVUKFJHK-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 229910052454 barium strontium titanate Inorganic materials 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- XWUPANOEJRYEPL-UHFFFAOYSA-N barium(2+);oxygen(2-);titanium(4+);zirconium(4+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ti+4].[Zr+4].[Ba+2] XWUPANOEJRYEPL-UHFFFAOYSA-N 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229910000416 bismuth oxide Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000005234 chemical deposition Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
- IUBGCAIAAJMNJS-UHFFFAOYSA-J dimagnesium;tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Mg+2].[Mg+2] IUBGCAIAAJMNJS-UHFFFAOYSA-J 0.000 description 1
- NKZSPGSOXYXWQA-UHFFFAOYSA-N dioxido(oxo)titanium;lead(2+) Chemical compound [Pb+2].[O-][Ti]([O-])=O NKZSPGSOXYXWQA-UHFFFAOYSA-N 0.000 description 1
- IVUXZQJWTQMSQN-UHFFFAOYSA-N distrontium;oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Sr+2].[Sr+2].[Ta+5].[Ta+5] IVUXZQJWTQMSQN-UHFFFAOYSA-N 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004870 electrical engineering Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical group C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000006390 lc 2 Substances 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 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
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 229910014031 strontium zirconium oxide Inorganic materials 0.000 description 1
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940100050 virazole Drugs 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/191—Deposition of organic active material characterised by provisions for the orientation or alignment of the layer to be deposited
-
- 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
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
-
- 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
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
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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]
- H10K10/464—Lateral top-gate IGFETs comprising only a single gate
-
- 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
Definitions
- the present invention relates to an organic thin film transistor having an organic semiconductor layer, and more particularly to an organic thin film transistor that includes a compound having high electron mobility and can operate at high speed.
- TFTs Thin film transistors are widely used as switching elements for display in liquid crystal display devices and the like.
- the cross-sectional structure of a typical conventional TFT as shown in c figure shown in FIG. 8, TFT may have a gate electrode and an insulator layer in this order on the substrate, on the insulator layer, the predetermined distance It has a source electrode and a drain electrode formed by opening.
- a semiconductor layer is formed on the insulator layer including the partial surfaces of both electrodes and exposed between the electrodes.
- the semiconductor layer forms a channel region, and the on / off operation is performed by controlling the current flowing between the source electrode and the drain electrode by the voltage applied to the gate electrode.
- FET field effect transistor
- CMOS complementary metal-oxide-semiconductor
- this TFT has been fabricated using amorphous or polycrystalline silicon.
- the CVD equipment used to fabricate TFTs using such silicon is very expensive, and the increase in the size of display devices using TFII is accompanied by a significant increase in manufacturing costs.
- the process of forming amorphous or polycrystalline silicon is performed at an extremely high temperature, the types of materials that can be used as substrates are limited, so that lightweight resin substrates and the like cannot be used. There was a problem that it could not be used.
- TFII using organic materials instead of amorphous or polycrystalline silicon has been proposed.
- Vacuum evaporation and coating methods are known as film forming methods used when forming TF ⁇ with an organic substance. This makes it possible to increase the size of the film, and the process temperature required during film formation can be made relatively low. For this reason, TF III using organic substances has the advantage that there are few restrictions on the selection of materials used for the substrate, and its practical application is expected, and TF ⁇ ⁇ using organic substances is actively reported.
- F. Ebisawa et al. Journal of Applied Physics, Vol. 54, pp. 325, 1983, A. Assadi et al., Applied Physics Letter, Vol. 53, pp. 195 1988, G.
- a polymer such as a conjugated polymer monothiophene (JP-A-8-228034, JP-A-8-228035, JP-A-9-232589) JP-A-10-125924 and JP-A-10-190001), metal phthalocyanine compounds (JP-A-2000-174277, etc.), condensed aromatic hydrocarbons such as pentacene (JP-A-5-55568) And Japanese Patent Application Laid-Open No. 2001-94107) are used alone or in a mixture with other compounds.
- the gazette only discloses fluorinated phthalocyanine ( On the other hand, there is an organic electroluminescence (EL) rater as a device using electron conduction in the same way, but an organic EL element is generally used. 1 0 0 ⁇ m whereas the flowing of the following 1 0 6 V / 'forcibly charge over more strong electric field cm in the direction of film thickness of the ultrathin film, several mu m or more in the case of the organic TFT It must flow a distance of 1 0 5 charges at a high speed VZ cm below electric field, organic matter itself, further conducting necessary That Do not.
- EL organic electroluminescence
- the on / Z-off ratio referred to here is the current flowing between the source and drain when the gate voltage is applied (on), and the current flowing between the source and drain when the gate voltage is not applied (off).
- the on-current is the current value (saturation current) when the current flowing between the source and drain is saturated, usually increasing the gate voltage. Disclosure of the invention
- the present invention has been made to solve the above-mentioned problem, and an object of the present invention is to provide an organic thin-film transistor having a high response speed (drive speed) and a high on-z-off ratio.
- the present inventors have conducted intensive studies to achieve the above object, and as a result, the use of a nitrogen-containing heterocyclic compound having a specific structure as a material for an organic semiconductor layer of an organic thin film transistor has resulted in a response speed ( (Drive speed) can be increased, and the present invention has been completed.
- the organic semiconductor layer comprises a nitrogen-containing heterocyclic compound in which a 5-membered ring having a nitrogen atom at a condensed site and a 5-membered or 6-membered ring are condensed.
- FIG. 1 is a diagram showing an example of the element configuration of the organic thin film transistor of the present invention.
- FIG. 2 is a diagram showing an example of the element configuration of the organic thin film transistor of the present invention.
- FIG. 3 is a diagram showing an example of the element configuration of the organic thin film transistor of the present invention.
- FIG. 4 is a diagram showing an example of the element configuration of the organic thin film transistor of the present invention.
- FIG. 5 is a diagram showing an example of the element configuration of the organic thin film transistor of the present invention.
- FIG. 6 is a diagram showing an example of the element configuration of the organic thin film transistor of the present invention.
- FIG. 7 is a diagram showing an element configuration of an organic thin-film transistor and a circuit configuration using the same in Example 1 of the present invention.
- FIG. 8 is a diagram showing an example of the element configuration of a typical conventional transistor. BEST MODE FOR CARRYING OUT THE INVENTION
- the organic thin-film transistor of the present invention is provided with at least three terminals of a gate electrode, a source electrode, and a drain electrode, an insulator layer, and an organic semiconductor layer on a substrate, and applies a current between a source and a drain to a gate electrode.
- the organic semiconductor layer contains a nitrogen-containing heterocyclic compound in which a 5-membered ring having a nitrogen atom at a condensed site and a 5-membered or 6-membered ring are condensed.
- the nitrogen-containing heterocyclic compound is preferably a compound represented by any one of the following general formulas (I) to (VII).
- R ⁇ , R 12 and R 13 each independently represent a hydrogen atom or a substituent, and c Z represents a group of atoms forming a 5-membered ring or a 6-membered ring.
- R 21 and R 22 each independently represent a hydrogen atom or a substituent.
- Z represents an atomic group forming a 5- or 6-membered ring.
- R 31 and R 32 each independently represent a hydrogen atom or a substituent.
- Z represents an atomic group forming a 5- or 6-membered ring.
- R 41 and R 42 each independently represent a hydrogen atom or a substituent.
- Z represents an atom group forming a 5- or 6-membered ring.
- R 51 represents a hydrogen atom or a substituent.
- Z 5 represents a group of atoms forming a 5- or 6-membered ring.
- R 61 represents a hydrogen atom or a substituent.
- Z 6 represents an atom group forming a 5- or 6-membered ring.
- R 71 represents a hydrogen atom or a substituent.
- ⁇ represents an atom group forming a 5- or 6-membered ring.
- alkyl group (preferably having 1 to 80 carbon atoms, more preferably having 1 to 40 carbon atoms, particularly preferably having 1 to 12 carbon atoms, for example, methyl, 'ethyl, iso-propyl) Tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 20 carbon atoms).
- an acyl group preferably C1 to C20, It preferably has 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include acetyl, benzoyl, formyl, and vivaloyl.
- An alkoxycarbonyl group (preferably having 2 to 0 carbon atoms, more preferably having 2 to 16 carbon atoms, and particularly preferably having 2 to 12 carbon atoms. Xycarbol, ethoxycarbonyl and the like. ), Aryloxycarbonyl group (preferably having 7 to 20 carbon atoms, more preferably having 7 to 16 carbon atoms, particularly preferably having 7 to 10 carbon atoms, and examples thereof include phenyloxycarbonyl).
- An acyloxy group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 16 carbon atoms, particularly preferably having 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy.
- An acylamino group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 16 carbon atoms, particularly preferably having 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino).
- An alkoxycarbonylamino group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 16 carbon atoms, particularly preferably having 2 to 12 carbon atoms, for example, methoxycarbonyl)
- an aryloxycarbonylamino group (preferably having 7 to 20 carbon atoms, more preferably having 7 to 16 carbon atoms, particularly preferably having 7 to 12 carbon atoms, For example, phenyloxycarbonylamino, etc.), a sulfonylamino group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 16 carbon atoms, and particularly preferably having 1 to 12 carbon atoms).
- methanesulfonylamino, benzenesulfonylamino, etc.), and a sulfamoyl group (preferably having 0 to 20 carbon atoms, more preferably having 0 to 16 carbon atoms, and particularly preferably having 0 to 16 carbon atoms).
- a carbamoyl group preferably having 1 carbon atom
- a sulfonyl group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 16 carbon atoms, particularly preferably having 1 to 12 carbon atoms, and examples include mesyl and tosyl.)
- a sulfinyl group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 16 carbon atoms, particularly preferably having 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl); Laid group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 16 carbon atoms, particularly preferably having 1 to 12 carbon atoms, and examples thereof include ureido, methylureide, and phenyl peridode.
- a phosphate amide group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 16 carbon atoms, particularly preferably having 1 to 12 carbon atoms, for example, getyl phosphate amide) , Phenyl Acid amides, etc.), hydroxy group, mercapto group, halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, A hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, a heterocyclic group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms, and For example, nitrogen atom, oxygen atom, sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl, furyl ', piperidyl, morpholino, benzoxazolyl
- substituents include an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an acyl group, an alkoxyl group, an aryloxy group, an acyloxy group, an alkoxycarbonyl group, and an aryloxycarbonyl group.
- Examples of the 5- or 6-membered ring formed by the atom group of the general formula (I) include pyrrole, pyrazole, imidazole, triazole, thiazole, thiadiazol, and oxazole.
- Triazole and triazine and more preferably triazole.
- Rizole and triazine more preferably imidazole and triazole '.
- Examples of the 5- or 6-membered ring formed by the atom group of DZs include pyrrole, pyrazolyl, imidazole, triazole, thiazole, thiadiazole, oxazolo , Oxaziazole, triazine, pyrimidine, pyridin, pyrazine, pyridazine and the like, preferably pyrrole, pyrazole, imidazole, triazole, more preferably pyrrole, Pyrazole and triazole, more preferably pyrrole and pyrazole.
- the 5-membered or 6-membered ring formed by the group of atoms of Z 4 in the general formula (IV) for example, Pyrrolidine, pyrazol, imidazole, triazole, thiazo-noreth, thiadiazol, oxazol, oxaziazol, triazine, pyrimidine ', pyridin, pyrazine, pyridazine and the like.
- pyrrole pyrazole, imidazole and triazole
- Is a 5- or 6-membered ring atomic group of Z 5 is formed of the general formula (V), for example, pyrrole ', pyrazole one Ruru Lee Midazo Ichiru, thiazole, Okisazo Ichiru', preparative Riaji down, Pyrimidine, pyridine, pyrazine, pyridazine and the like, preferably pyrrolidine, pyrazole, imidazole, pyrimidine, pyrazine, pyridazine, and more preferably pyrrole, virazole, pyrimidine, pyridazine. And more preferably pyrrol or pyrazole.
- Examples of the 5- or 6-membered ring formed by the atom group of ⁇ in the general formula (VI) include, for example, pyrrolyl ', imidazole, thiazolyl, oxazolyl, pyrimidine, pyridine, Pyrazine, pyridazine and the like, preferably pyrrol, imidazole, pyrimidine, pyrazine 'and pyridazine, more preferably pyrrole, pyrimidine, pyrazine and pyridazine, and even more preferably pyrrolidine. And pyrimidine.
- Examples of the 5- or 6-membered ring formed by the group of ⁇ atoms of the general formula (VI I) include pyrrole ', imidazole, thiazol', oxazole, pyrimidine, pyridine, Pyrazine, pyridazine and the like, preferably pyrrole, imidazole, pyrimidine, pyrazine and pyridazine, more preferably pyrrole, pyrimidine, virazine and pyridazine, more preferably pyrrole and pyridazine. It is a mijin.
- the 5- or 6-membered ring formed by to ⁇ 7 may have a substituent,
- examples similar to those described for Ru, R 12 , R 13 , R 21 , R 22 , R 31 , R 32 , R 41 , R 42 , R si R 61 and R 71 may be mentioned. And preferred substituents as well.
- the compound represented by the general formula (I) is preferably a compound represented by any of the following general formulas (Ia) to (If), and (Ia) to (I — c). ) Is more preferably a compound represented by any one of the above.
- R i fl and R LF2 each independently represent a hydrogen atom or a substituent.
- R lal , R lbl , R lcl , R lc2 , R idi, R ld2 , R lel and R le2 each independently include Ru, it is the same as those described in R 12 and R 13, and preferred examples thereof are also the same.
- R la2, R i b2, R , R ld3, R i s3, are a substituent you express R and R LF2, each independently, for example, an alkyl group (preferably a carbon number 1-2 0, More preferably, it has 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms.
- alkenyl group preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, and particularly preferably having 2 to 8 carbon atoms.
- Alkynyl group preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably carbon Numbers 2 to 8, for example, propargyl , 3-pentynyl, etc.
- aryl group preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, particularly preferably having 6 to 12 carbon atoms, for example, phenyl, p-methylphenyl, naphthyl, etc.
- an acyl group preferably having 1 to 20 carbon atoms, more preferably having 1 to 16 carbon atoms, particularly preferably having 1 to 12 carbon atoms, for example, acetyl and benzoyl
- Formyl, bivaloyl, etc. an alkoxycarbonyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 16 carbon atoms, particularly preferably having 2 to 12 carbon atoms
- An aryloxycarbonyl group (preferably having 7 to 20 carbon atoms, more preferably having 7 to 16 carbon atoms, particularly preferably having 7 to 10 carbon atoms, and examples thereof include phenyloxycarbonyl).
- a sulfamoyl group (preferably having 0 to 20 carbon atoms, more preferably having 0 to 16 carbon atoms, particularly preferably having 0 to 12 carbon atoms, for example, sulfamoinole, methinoresnorefamoi Nole, dimethinoresnorefamoinole, pheninoresnolepuamoyl, etc.), and a carbamoyl group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 16 carbon atoms, particularly preferably having 1 to 16 carbon atoms).
- 1 to 12 and include, for example, canoleno moinole, methyl canolebamoinole, jetinore canoleno moinole, fenirulcanole bamoyl, etc.), sulfonyl (Preferably 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, mesyl, tosyl and the like.), A sulfinyl group (preferably Has 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl and benzenesulfinyl.), A heterocyclic group ( It preferably has 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms.
- hetero atom examples include a nitrogen atom, an oxygen atom, and a sulfur atom, and specifically, for example, imidazolyl, pyridyl, and quino.
- Ryl furyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, etc.), and the like.
- R lal, R lbl, R, R lc 2, R is preferably set to, and R l d2, R le, a hydrogen atom, an alkyl group, an alkenyl group, Ariru group, alkoxides aryloxycarbonyl group, Shiano group, aromatic Is a heterocyclic group.
- Rla2 , Rlb2 , R, R, R, R and R are preferable. More preferably, they are a hydrogen atom, an alkyl group, an aryl group, and an aromatic heterocyclic group.
- the compound represented by the general formula (II) is preferably a compound represented by any of the following general formulas (II-a) to (II-f), and (II-a) to (II-c) It is more preferable that the compound is represented by any one of the above.
- R 21 and R 22 are the same as described above, and specific examples and preferred examples are also the same.
- R 2f i ⁇ Pi R 2 f 2 each independently represents a hydrogen atom or a substituent.
- R 2e i and R 2e2 are each independently the same as those described in the general formula (I), and preferred examples are also the same.
- R 2. 3 is a R 2 fi and substituents you express by R 2 f 2, independently, as those described in R la2 of the general formula (I one a) 'is the same, the preferred examples are also Is the same.
- R 2 ol and R 2 preferably a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an alkoxycarbonyl group, a cyano group
- the compound represented by the general formula (III) is more preferably a compound represented by the following general formulas (III-a) to (III-c).
- R 31 and R 32 are the same as above, and specific examples and And preferred examples are also the same.
- R 3al, R 3a2 and R 3Ia3 each independently represent a hydrogen atom or a substituent.
- R 3al is an example of the substituents represented by R 3a2 and R 3a3, each independent, is similar to that described in R u of the formula (I), preferred examples are also same as It is.
- R 3al as the R 3a2 and R 3a3 is preferably a hydrogen atom, an alkyl group, an alkenyl group, Ariru group, an alkoxycarbonyl group, Shiano group, terrorist the aromatic heterocyclic group.
- R 31 and R 32 are the same as described above, and specific examples and preferred examples are also the same.
- R 3bl ⁇ R 3 b4 each independently represent a hydrogen atom or a substituent, it is a substituent, for example, an alkyl group, a cycloalkyl group, Ararukiru group, an alkenyl Group, cycloalkenyl group, alkynyl group, hydroxyl group, menolecapto group, alkoxyl group, alkylthio group, arylether group, arylthioether group, aryl group, heterocyclic group, halogen atom , Haloalkane residue, haloalkene residue, haloalkyne residue, cyano group, aldehyde group, carboxylic group, carboxyl group, ester group, carbamoyl group, amino group, nitrite A mouth group, a silyl group, a siloxanyl group, and the like, and may form a ring structure with an adjacent substituent.
- the general formula (III-b) is preferably represented by the following general formula (III-c),
- R 31 and R 3bl to R 3b4 are the same as described above.
- to R 3c5 each independently represent a hydrogen atom or a substituent;
- the substituent include an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxyl group, an alkylthio group, an aryl ether group, and an arylthio group.
- the compound represented by the general formula (IV) is preferably a compound represented by any of the following general formulas (IV-a) to (IV-g), and (IV-a) to (IV-b). ) No More preferably, the compound is represented by the formula:
- R 4 and R 12 are the same as described above, and the specific examples and preferred examples are also the same.
- R 4al, R 4b i, Ri b2, R 4cl is an example of R 4c2, R 4 dl ⁇ Pi R substituent you express in 4d2, independently, described in the the general formula (I) It is the same as the above, and the preferred example is also the same.
- R 4b3 , R 4c3 , R 4d3 , R 4el and R are each independently the same as those described for R la in the general formula (Ia), and are preferred.
- the example is the same.
- R 4a i, R -ib!, R, R 4d i and R 4d2 are preferably a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an alkoxyl group, a cyano group, It is an aromatic heterocyclic group.
- R 4b3 , R, R 4d3 , R 4o i and R 4 are a hydrogen atom, an alkyl group, an aryl group and an aromatic heterocyclic group.
- X 4a is represented by CR 4a2 (R 4a3 ) or NR 4a4 , and R 4a2 and R 4a3 each independently represent a hydrogen atom or a substituent, and Are each independently the same as described in the above for formula (I), and the preferred examples are also the same.
- R 4a4 represents a hydrogen atom or a substituent, and the substituent is represented by the formula (I) — Same as that described for R la2 in a), and the preferred examples are also the same.
- R "and R42 are the same as described above, and specific examples and preferred examples are also the same.
- R 4f l ⁇ R. Lf4 each independently represent a hydrogen atom or a substituent, it is a substituted group, alkyl group, cycloalkyl group, Araru kill group, an alkenyl group , Cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxyl group, alkylthio group, aryl ether group, arylthioether group, aryl group, heterocyclic group, halogen atom,. ', Loalkane residue, c Roalkene residue, octa-alkyne residue, cyano group, aldehyde group, carbonyl group.
- R. lsl ⁇ ! 4s5 each independently represents a hydrogen atom or a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, and an alkoxyl group.
- the compound represented by the formula is preferably a compound represented by any of the following general formulas (Va) to (Ve), and is preferably represented by any of (Va) to (Vb). More preferably, the compound is
- R 51 is the same as defined above, specific examples and preferred examples are also the same.
- R 5al , Rsbi, R 5b2 , R 5cl , R 5c2 , Rsdi and R Sd2 are each independently the same as those described in the general formula (I). And the preferred examples are also the same.
- R 5b3 , R so3, Rs, Rsoi and R 5e2 are each independently the same as those described for R la2 in formula (Ia), and are preferred.
- the columns are the same.
- R 5b3 and R 5 . 3 , Rsds, Rssl, and R5e2 are preferably a hydrogen atom, an alkyl group, an aryl group, or an aromatic heterocyclic group.
- X 5a is represented by CR 5a2 (R 5a3 ) or N,
- R 5a2 and R 5n3 each independently represent a hydrogen atom or a substituent, and the substituents are each independently the same as those described in the general formula (I), and the preferred examples are also the same.
- R5a4 represents a hydrogen atom or a substituent, and the substituent is the same as that described for Rla2 in Formula (Ia), and the preferred examples are also the same.
- the compound represented by the general formula (VI) is more preferably a compound represented by the following general formula (VI-a).
- R 61 is the same as described above, and specific examples and preferred examples are also the same.
- F al , R ea2 , Re a3 and R6 a4 each independently represent a hydrogen atom or a substituent, and examples of the substituent include those represented by the general formula (I )), And the preferred examples are also the same.
- the compound represented by the general formula (VII) is preferably a compound represented by any of the following general formulas (VII-a) to (VII-d).
- R R R and R each independently represent a hydrogen atom or a substituent.
- R 7c3 is a substituent represented by R 7c3, are the same as those explained in R la2 of the general formula (I one a), and preferred examples thereof are also the same.
- R vbi R and R 7d3 are preferably a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an alkoxycarbonyl group, a cyano group, or an aromatic heterocyclic group.
- X 7b are each independently represented by CR 7a2 (R 7a3 ) or NR 4 , R 7a2 and R 7a3 each independently represent a hydrogen atom or a substituent,
- the substituents are each independently the same as described in the above for formula (I), and preferred examples are also the same.
- R 4 represents a hydrogen atom or a substituent.
- the heterocyclic compound of the present invention may be a low molecular weight compound, and a high molecular weight compound having a ⁇ group connected to the poly main chain (preferably a weight average molecular weight of 100,500,000, particularly Preferably 500,000, more preferably 100,000,000) or a high molecular weight compound having the compound of the present invention in the main chain. (Preferably a weight average molecular weight of 100 to 500,000, particularly preferably 500 to 200,000, more preferably 100 to 100) 0 0).
- a high molecular weight compound it may be a homopolymer or a copolymer with another monomer.
- the compound having ffl in the present invention is preferably a low molecular weight compound.
- the compound of the present invention can be synthesized by various synthetic methods.
- the compounds can be synthesized with reference to the methods described in JP-A Nos. 4-174204 and 5-313.
- the element configuration of the organic thin film transistor of the present invention is such that a gate electrode, a source electrode, and a drain electrode are provided on a substrate, and an insulator layer and an organic semiconductor layer are provided.
- the thin film transistor is not limited as long as it is controlled by applying a voltage to the electrode, and may have a known element configuration.
- the organic thin film transistor of the present invention has a field effect transistor. It has a star (FET: Field Effect Transistor) structure.
- the organic thin-film transistor is separated from the organic semiconductor layer (organic compound layer) by a predetermined distance from a source electrode and a source electrode, and a source electrode and a drain electrode formed so as to face each other at a predetermined distance.
- a gate electrode formed by applying a voltage to the gate electrode to control a current flowing between the source and drain electrodes.
- the distance between the source electrode and the drain electrode is determined depending on the use of the organic thin film transistor of the present invention, and is usually 0.1 ⁇ m to 1 mm, preferably 1 ⁇ ! ⁇ 100 ⁇ , more preferably 5 ⁇ ! ⁇ 1 ⁇ ⁇ ⁇ ⁇ ⁇ .
- the organic thin film transistor of the element A has a gate electrode (layer) and an insulator layer on a substrate in this order.
- a pair of source / drain electrodes formed at predetermined intervals on the insulator layer, and an organic semiconductor layer is formed thereon.
- the organic semiconductor layer forms a channel region, and the on / off operation is performed by controlling the current flowing between the source electrode and the drain electrode by the voltage applied to the gate electrode.
- the substrate in the organic thin-film transistor of the present invention has a structure of the organic thin-film transistor.
- inorganic materials such as metal oxides and nitrides, plastics (PET, PES, PC), metal substrates, or composites or laminates of these A body or the like can also be used.
- PET plastics
- PES PES
- PC metal substrates
- composites or laminates of these A body or the like can also be used.
- the substrate may not be used.
- a silicon (Si) wafer is often used as a substrate material.
- Si itself can be used as a gate electrode and a substrate.
- by oxidizing the surface of the S i it is also possible to form the S i ⁇ 2 utilizing as an insulating layer (in this case, when the element A as an example, by sea urchin shown in FIG. 6, the substrate A metal layer such as Au is often formed on the Si substrate serving as the gate electrode as an electrode for connecting lead wires.
- Examples of the material of the gate electrode, the source electrode, and the drain electrode in the organic thin film transistor of the present invention include chrome (Cr), titanium (Ti), copper (Cu), and aluminum (A1). ), Molybdenum (Mo), tungsten (W), nickel (Ni), gold (Au), palladium (Pd), indium, platinum (Pt), silver (Ag), tin (Sn) ), Magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and other metals and alloys, as well as indium tin oxide alloys (ITO ), Heavily doped silicon, tin oxide (NESA), conductive polyaline, conductive polypyrrole, conductive polythiazyl, conductive polymer, etc., and combinations thereof.
- the thickness of the gate electrode, the source electrode and the drain electrode is preferably 30 to 500 nm, respectively.
- the material of the insulator layer in the organic thin film transistor of the present invention include silicon oxide, silicon nitride, titanium oxide, barium oxide, strontium oxide, zirconium oxide, and lead oxide. , Lanthanum oxide, fluorinated oxide, magnesium oxide, bismuth oxide, tantalum oxide, niobium oxide, and the like.
- silicon dioxide barium strontium titanate, barium titanate zirconate, and zirconium.
- silicon nitride based compounds such as Si 3 N 4 , Si XN y (x, y> 0), and Si ON x are also preferable.
- the insulator layer may also be formed of a precursor containing an alkoxide metal, and a solution of this precursor is coated on a substrate, for example, and the insulator is formed by performing a chemical solution treatment including a heat treatment. A layer is formed.
- the metal in the alkoxide metal is selected from, for example, transition metals, lanthanides, and main group elements.
- the metal is selected from the group consisting of Norium (Ba), Strontium (Sr), and Titanium ( T i), bismuth (B i), tantalum (T a), dinolecon (Z r), iron (F e), nickel (N i), manganese (M n), lead (P b), lanthanum ( L a), lithium (L i), sodium (N a), potassium (K), norevidium (R b), cesium (C s), fransium (F r) beryllium (B e) magnesium ( Mg), calcium (Ca), niobium (Nb), thallium (T1), mercury (Hg), copper (Cu), cobalt (Co), rhodium (Rh), scandium (S c) and yttrium (Y).
- alkoxide in the alkoxide metal examples include meta Alcohols, including ethanol, propanol, isopanol, butanol, and isobutanol, methoxyethanol ', ethoxyethanol, propoxyethanol', butoxyethanol, pentoxyethanol, heptoxyethanol, and methoxyethanol.
- alkoxy alcohols including., Ethoxypropanol, propoxypropanol, butoxypropanol, pentoxypropanol, and heptoxypropanol.
- the insulator layer when the insulator layer is formed of the above-described material, a depletion layer is easily generated in the insulator layer, and the threshold voltage for transistor operation can be reduced. Also, among the above materials, in particular, when an insulator layer is formed of silicon nitride such as Si 3 N 4 , Si XN y (x, y> 0), and Si ON x, a depletion layer is generated. As a result, the threshold voltage for transistor operation can be further reduced.
- the thickness of the insulator layer is preferably from 10 to 150 nm. Usually, for example, the insulator layer is formed by means such as vacuum deposition, sputtering, thermal CVD, thermal oxidation, and anodic oxidation. You.
- the thickness of the organic semiconductor layer in the organic thin film transistor of the present invention is not particularly limited, it is usually in the range of several nm to 1 ⁇ m, and preferably in the range of 10 nm to 250 nm.
- the method for forming the organic semiconductor layer is not particularly limited, and known methods can be applied. Examples thereof include molecular beam deposition (MBE), vacuum deposition, chemical vapor deposition, and deposition of a solution in which a material is dissolved in a solvent.
- the organic semiconductor layer is formed of the material of the organic semiconductor layer as described above by means of a combination thereof.
- the method for forming the organic thin film transistor of the present invention is not particularly limited, and may be a known method. According to the method, a series of device fabrication steps from substrate loading, gate electrode formation, insulator layer formation, organic semiconductor layer formation, source electrode formation, and drain electrode formation can be performed without exposure to the atmosphere. This is preferable because the element performance can be prevented from being hindered by moisture, oxygen, or the like in the atmosphere due to contact with the element.
- the steps after the organic semiconductor layer formation are not exposed to the air at all, and immediately before the organic semiconductor layer formation, the surface on which the organic semiconductor layer is laminated (For example, in the case of element A, the surface where the source electrode and drain electrode are partially laminated on the insulating layer) is cleaned and activated by ultraviolet irradiation, ultraviolet.z ozone irradiation, oxygen plasma, argon plasma, etc. It is desirable to stack semiconductor layers.
- the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
- An organic thin film transistor was manufactured according to the following procedure. First, the surface of an Si substrate (also used as a P-type specific resistance 1 ⁇ cm gate electrode) was oxidized by a thermal oxidation method, and a 40-nm-thick thermal oxide film was formed on the substrate to form an insulator layer. Furthermore, after completely removing the SiO 2 film formed on one side of the substrate by dry etching, a chromium film was formed to a thickness of 20 nm by a sputtering method, and then gold (Au) was further formed thereon. 100 nm Suno,). The film was formed by a cutter and used as an extraction electrode.
- a 150 nm-thick gold film is formed on this insulator film through a metal mask, so that the source electrode and the drain electrode that are not in contact with each other are spaced apart by a distance (channel length L) of 100 nm. It was formed to have a thickness of 0 ⁇ m. At this time, the film was formed so that the width of the source electrode and the drain electrode (channel width W) was 4 mm. Subsequently, the compound (1) was formed as an organic semiconductor layer having a thickness of 150 nm by a vacuum evaporation method through another metal mask to produce an organic thin film transistor (see FIG. 7). The obtained organic thin film transistor, in the circuit configuration shown in FIG.
- Example 1 as a material of the organic semiconductor layer, the first organic thin film transistor obtained c was prepared an organic thin film transistor in the same manner except for using the compound described in Table instead of the compound (1), carried out As in Example 1, a gate voltage V of +40 V. Table 1 shows the results of measuring the on / off ratio of the current between the source and drain electrodes and calculating the field effect mobility ⁇ of electrons. Table 1
- Chromium was deposited to a thickness of 100 nm on a glass substrate having a thickness of 1 mm by a vacuum evaporation method, and this was used as a gate electrode.
- SiO 2 was formed as an insulator layer having a thickness of 300 nm on the gate electrode by sputtering.
- a gold (Au) film having a thickness of 150 ⁇ m is formed on this insulating layer through a metal mask, so that a source electrode and a drain electrode which are not in contact with each other are spaced apart (channel length).
- the compound (77) was formed as an organic semiconductor layer having a thickness of 150 nm by a vacuum evaporation method to produce an organic thin film transistor (see FIG. 1).
- the obtained organic thin film transistor in the same circuit configuration as that in Example 1, by applying a gate voltage V c of + 4 0 V, shed current by applying a voltage between the source one drain.
- V c gate voltage
- the on / off ratio of the current between the source and drain electrodes in the current saturation region was measured to be 3.1 X 10 s .
- X 1 0- 3 cm 2 / V s was calculated electron field effect mobility mu.
- the source electrode and the drain electrode that are not in contact with each other can be separated by a distance (channel length L) of 1 nm. It was formed so that its width (channel width W) was 4 mm. Then, through another metal mask, compound by vacuum vapor deposition (1 4 9) as the 1 5 0 nm thickness of the organic semiconductor layer was formed, the aluminum oxide used. Then sputtering (A 1 2 O 3 ) was deposited to a thickness of 200 nm to form an insulator layer. Most Later, the gate electrode (A1) was sputtered using another mask to produce an organic thin-film transistor (see Fig. 3).
- the obtained organic thin film transistor in the same circuit configuration as that in Example 1, by applying a gate voltage V c of + 4 0 V, shed current by applying a voltage between the source one drain. As a result, was 3. 8 X 1 0 8 was measured O emissions. Z off ratio of the current between the source one drain electrode in the current saturation region. In addition, calculation of electron field-effect mobility mu 2. was 1 X 1 0- 2 cm 2 / V s.
- a t- compound (309) using a polyethylene terephthalate film having a thickness of 20 Oym as a substrate was dissolved in toluene at 3% by mass, and a film was formed on the substrate by a spin-coating method, and a nitrogen atmosphere was used. It was dried at 120 ° C. below.
- gold (Au) with a thickness of 150 nm through a metal mask using a vacuum evaporation apparatus, the source electrode and the drain electrode that are not in contact with each other are separated by a distance (channel length L). 10 ⁇ ⁇ , and the width (channel width W) was formed to be 4 mm.
- polyethylene was vacuum deposited using a vacuum deposition method to form an insulator layer.
- A1 was vacuum-deposited on it to form a gate electrode (see Fig. 4).
- the obtained organic thin film transistor in the same circuit configuration as that in Example 1, by applying a gate voltage V G of + 4 0 V, shed current by applying a voltage between the source one drain.
- V G gate voltage
- the on / off ratio of the current between the source and drain electrodes in the current saturation region was measured and found to be 4.3 ⁇ 10 6 .
- the field effect mobility ⁇ of the electrons was calculated, it was 8.6 ⁇ 10 4 cm 2 / Vs.
- Example 1 instead, except for using Kisade force Furuoro copper lid port Shianina one preparative (F 16 P c C u) to the to produce an organic thin film transistor data in the same manner (see FIG. 7 of the compound (1) ).
- the obtained organic thin film transistor in the same circuit configuration as that in Example 1, by applying a gate voltage V c of + 4 0 V, shed current by applying a voltage between the source one drain.
- V c gate voltage
- the on / off ratio of the current between the source and the drain electrode in the current saturation region was measured and found to be 1.2 ⁇ 10 3 .
- Was calculated electron field-effect mobility mu 1. Was 3 X 1 0 one 3 cm 2 / V s. Industrial applicability
- the organic thin film transistor of the present invention has a high response speed (driving speed), and is ON / OFF, by using a heterocyclic compound having a specific structure having high electron mobility as a material of the organic semiconductor layer.
- the ratio is large and the performance as a transistor is high.
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
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- Thin Film Transistor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims
Priority Applications (3)
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DE602004021278T DE602004021278D1 (de) | 2003-10-31 | 2004-10-27 | Organischer dünnfilm-transistor |
US10/577,325 US7714319B2 (en) | 2003-10-31 | 2004-10-27 | Organic thin film transistor |
EP04793326A EP1679747B1 (en) | 2003-10-31 | 2004-10-27 | Organic thin film transistor |
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JP2003372558A JP4795634B2 (ja) | 2003-10-31 | 2003-10-31 | 有機薄膜トランジスタ |
JP2003-372558 | 2003-10-31 |
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WO2005043630A1 true WO2005043630A1 (ja) | 2005-05-12 |
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PCT/JP2004/016293 WO2005043630A1 (ja) | 2003-10-31 | 2004-10-27 | 有機薄膜トランジスタ |
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US (1) | US7714319B2 (ja) |
EP (1) | EP1679747B1 (ja) |
JP (1) | JP4795634B2 (ja) |
KR (1) | KR20060113682A (ja) |
CN (1) | CN100454581C (ja) |
DE (1) | DE602004021278D1 (ja) |
WO (1) | WO2005043630A1 (ja) |
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Cited By (16)
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US8088928B2 (en) | 2005-08-04 | 2012-01-03 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
US8093401B2 (en) | 2005-08-04 | 2012-01-10 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
WO2007034282A3 (en) * | 2005-09-19 | 2007-05-18 | Pfizer Prod Inc | Diaryl-imidazole compounds condensed with a heterocycle as c3a receptor antagonists |
WO2007034282A2 (en) * | 2005-09-19 | 2007-03-29 | Pfizer Products Inc. | Diaryl-imidazole compounds condensed with a heterocycle as c3a receptor antagonists |
WO2008059714A1 (fr) * | 2006-11-17 | 2008-05-22 | Nihon Medi-Physics Co., Ltd. | Composés inédits présentant une affinité pour la substance amyloïde |
JPWO2008059714A1 (ja) * | 2006-11-17 | 2010-03-04 | 日本メジフィジックス株式会社 | 新規アミロイド親和性化合物 |
US7893086B2 (en) | 2007-06-20 | 2011-02-22 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
WO2009057577A1 (ja) * | 2007-10-30 | 2009-05-07 | Nihon Medi-Physics Co., Ltd. | 新規アミロイド親和性化合物の使用及び製造方法 |
JP2009242293A (ja) * | 2008-03-31 | 2009-10-22 | Semiconductor Energy Lab Co Ltd | 金属錯体、発光素子、発光装置及び電子機器 |
US8343997B2 (en) | 2008-12-19 | 2013-01-01 | Sirtris Pharmaceuticals, Inc. | Thiazolopyridine sirtuin modulating compounds |
US8492401B2 (en) | 2008-12-19 | 2013-07-23 | Glaxosmithkline Llc | Thiazolopyridine sirtuin modulating compounds |
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Also Published As
Publication number | Publication date |
---|---|
US20070120111A1 (en) | 2007-05-31 |
KR20060113682A (ko) | 2006-11-02 |
US7714319B2 (en) | 2010-05-11 |
EP1679747A1 (en) | 2006-07-12 |
EP1679747A4 (en) | 2008-07-09 |
EP1679747B1 (en) | 2009-05-27 |
CN1902761A (zh) | 2007-01-24 |
DE602004021278D1 (de) | 2009-07-09 |
JP4795634B2 (ja) | 2011-10-19 |
JP2005136317A (ja) | 2005-05-26 |
CN100454581C (zh) | 2009-01-21 |
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