WO2008013427A1 - Organic tfts and method for fabricating the same - Google Patents
Organic tfts and method for fabricating the same Download PDFInfo
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- WO2008013427A1 WO2008013427A1 PCT/KR2007/003630 KR2007003630W WO2008013427A1 WO 2008013427 A1 WO2008013427 A1 WO 2008013427A1 KR 2007003630 W KR2007003630 W KR 2007003630W WO 2008013427 A1 WO2008013427 A1 WO 2008013427A1
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- Prior art keywords
- group
- ether
- formula
- ester
- independently
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 40
- 239000010409 thin film Substances 0.000 claims abstract description 92
- 239000004065 semiconductor Substances 0.000 claims abstract description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 77
- 239000001257 hydrogen Substances 0.000 claims abstract description 77
- 239000000126 substance Substances 0.000 claims abstract description 58
- 125000000524 functional group Chemical group 0.000 claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 claims abstract description 37
- 230000008569 process Effects 0.000 claims abstract description 31
- -1 anthryl ether Chemical compound 0.000 claims description 88
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 59
- 125000003277 amino group Chemical group 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 125000001033 ether group Chemical group 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000004185 ester group Chemical group 0.000 claims description 48
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 48
- 150000007970 thio esters Chemical group 0.000 claims description 46
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 43
- 125000000879 imine group Chemical group 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 125000002560 nitrile group Chemical group 0.000 claims description 39
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 14
- 125000003158 alcohol group Chemical group 0.000 claims description 12
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 238000001771 vacuum deposition Methods 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 150000003568 thioethers Chemical class 0.000 claims description 6
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 claims description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 4
- GPAAEZIXSQCCES-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxymethoxymethoxy)ethane Chemical compound COCCOCOCOCCOC GPAAEZIXSQCCES-UHFFFAOYSA-N 0.000 claims description 4
- ARARQWKFKMWCDL-UHFFFAOYSA-N 1-nitro-2-[(2-nitrophenyl)methoxymethyl]benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1COCC1=CC=CC=C1[N+]([O-])=O ARARQWKFKMWCDL-UHFFFAOYSA-N 0.000 claims description 4
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 4
- ZQVMXWDQXLWKLE-UHFFFAOYSA-N 4-methoxy-2-(4-methoxyoxan-2-yl)oxyoxane Chemical compound C1C(OC)CCOC1OC1OCCC(OC)C1 ZQVMXWDQXLWKLE-UHFFFAOYSA-N 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 4
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005462 imide group Chemical group 0.000 claims description 4
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 claims description 4
- OJGGXQRRIZICIT-UHFFFAOYSA-N methoxysulfanyl(methoxysulfanylmethoxy)methane Chemical compound COSCOCSOC OJGGXQRRIZICIT-UHFFFAOYSA-N 0.000 claims description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 4
- 150000004250 monothioacetals Chemical class 0.000 claims description 4
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000101 thioether group Chemical group 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 3
- IEPBPSSCIZTJIF-UHFFFAOYSA-N bis(2,2,2-trichloroethyl) carbonate Chemical compound ClC(Cl)(Cl)COC(=O)OCC(Cl)(Cl)Cl IEPBPSSCIZTJIF-UHFFFAOYSA-N 0.000 claims description 3
- ACBQROXDOHKANW-UHFFFAOYSA-N bis(4-nitrophenyl) carbonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 ACBQROXDOHKANW-UHFFFAOYSA-N 0.000 claims description 3
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims description 3
- PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 claims description 3
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229940066528 trichloroacetate Drugs 0.000 claims description 3
- FTVXFBJENACRRL-UHFFFAOYSA-N (1-hydroxypiperidin-2-yl) carbamate Chemical compound NC(=O)OC1CCCCN1O FTVXFBJENACRRL-UHFFFAOYSA-N 0.000 claims description 2
- KLWCNEYVHPBUNM-UHFFFAOYSA-N (1-methylcyclobutyl) carbamate Chemical compound NC(=O)OC1(C)CCC1 KLWCNEYVHPBUNM-UHFFFAOYSA-N 0.000 claims description 2
- LZZRHUUMSXNYBI-UHFFFAOYSA-N (2,4-dichlorophenyl)methyl carbamate Chemical compound NC(=O)OCC1=CC=C(Cl)C=C1Cl LZZRHUUMSXNYBI-UHFFFAOYSA-N 0.000 claims description 2
- AWOKSNNHYRGYIA-UHFFFAOYSA-N (4,5-dimethoxy-2-nitrophenyl)methyl carbamate Chemical compound COC1=CC(COC(N)=O)=C([N+]([O-])=O)C=C1OC AWOKSNNHYRGYIA-UHFFFAOYSA-N 0.000 claims description 2
- FPBOSUGVPBRYCA-UHFFFAOYSA-N (4-nitrophenyl)methyl carbamate Chemical compound NC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 FPBOSUGVPBRYCA-UHFFFAOYSA-N 0.000 claims description 2
- TTXKLVVJWALEOY-UHFFFAOYSA-N 1,2-benzoxazol-5-ylmethyl carbamate Chemical compound NC(=O)OCC1=CC=C2ON=CC2=C1 TTXKLVVJWALEOY-UHFFFAOYSA-N 0.000 claims description 2
- 150000000093 1,3-dioxanes Chemical class 0.000 claims description 2
- 150000004889 1,3-dithianes Chemical class 0.000 claims description 2
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims description 2
- WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical class C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 claims description 2
- GAHRWPUTGHCERR-UHFFFAOYSA-N 1-[bis(2-chloroethoxy)methoxy-(2-chloroethoxy)methoxy]-2-chloroethane Chemical compound ClCCOC(OCCCl)OC(OCCCl)OCCCl GAHRWPUTGHCERR-UHFFFAOYSA-N 0.000 claims description 2
- FJANNOJSTOGZHK-UHFFFAOYSA-N 1-adamantyl carbamate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)N)C3 FJANNOJSTOGZHK-UHFFFAOYSA-N 0.000 claims description 2
- ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 claims description 2
- PPJVXZVTPWQOQS-UHFFFAOYSA-N 1-ethoxy-1-(1-ethoxyethoxy)ethane Chemical compound CCOC(C)OC(C)OCC PPJVXZVTPWQOQS-UHFFFAOYSA-N 0.000 claims description 2
- IGHQOFUUDYGVMD-UHFFFAOYSA-N 1-methoxy-4-[[(4-methoxyphenyl)-diphenylmethoxy]-diphenylmethyl]benzene Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OC(C=1C=CC(OC)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IGHQOFUUDYGVMD-UHFFFAOYSA-N 0.000 claims description 2
- SPXOTSHWBDUUMT-UHFFFAOYSA-N 138-42-1 Chemical class OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-N 0.000 claims description 2
- QPLJYAKLSCXZSF-UHFFFAOYSA-N 2,2,2-trichloroethyl carbamate Chemical compound NC(=O)OCC(Cl)(Cl)Cl QPLJYAKLSCXZSF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 2
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 claims description 2
- YFEXZJKJPFNYKB-UHFFFAOYSA-N 2-(oxolan-2-yloxy)oxolane Chemical compound C1CCOC1OC1OCCC1 YFEXZJKJPFNYKB-UHFFFAOYSA-N 0.000 claims description 2
- GBWMWHHLQDBPFP-UHFFFAOYSA-N 2-(thian-2-yloxy)thiane Chemical compound S1CCCCC1OC1SCCCC1 GBWMWHHLQDBPFP-UHFFFAOYSA-N 0.000 claims description 2
- JMTBNBFBHBCERV-UHFFFAOYSA-N 2-(thiolan-2-yloxy)thiolane Chemical compound C1CCSC1OC1SCCC1 JMTBNBFBHBCERV-UHFFFAOYSA-N 0.000 claims description 2
- DTCYSRAEJHGSNY-UHFFFAOYSA-N 2-methoxy-2-(2-methoxypropan-2-yloxy)propane Chemical compound COC(C)(C)OC(C)(C)OC DTCYSRAEJHGSNY-UHFFFAOYSA-N 0.000 claims description 2
- SDJNOBUNFYNROE-UHFFFAOYSA-N 2-methylbut-3-yn-2-yl carbamate Chemical compound C#CC(C)(C)OC(N)=O SDJNOBUNFYNROE-UHFFFAOYSA-N 0.000 claims description 2
- 150000000499 3-oxazolines Chemical class 0.000 claims description 2
- UBARRNXCKBFUEN-UHFFFAOYSA-N 4,5-diphenyl-5h-1,3-oxazol-2-one Chemical compound N=1C(=O)OC(C=2C=CC=CC=2)C=1C1=CC=CC=C1 UBARRNXCKBFUEN-UHFFFAOYSA-N 0.000 claims description 2
- DVRKZTKTNYRYLF-UHFFFAOYSA-N 9-methoxyanthracene Chemical compound C1=CC=C2C(OC)=C(C=CC=C3)C3=CC2=C1 DVRKZTKTNYRYLF-UHFFFAOYSA-N 0.000 claims description 2
- ZZOKVYOCRSMTSS-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl carbamate Chemical compound C1=CC=C2C(COC(=O)N)C3=CC=CC=C3C2=C1 ZZOKVYOCRSMTSS-UHFFFAOYSA-N 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical class CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003047 N-acetyl group Chemical group 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- LXKLUWFIBVXFGX-QPJJXVBHSA-N [(e)-3-phenylprop-2-enyl] carbamate Chemical compound NC(=O)OC\C=C\C1=CC=CC=C1 LXKLUWFIBVXFGX-QPJJXVBHSA-N 0.000 claims description 2
- DSLOWNUUMZVCAC-UHFFFAOYSA-N [dimethyl(propan-2-yl)silyl]oxy-dimethyl-propan-2-ylsilane Chemical compound CC(C)[Si](C)(C)O[Si](C)(C)C(C)C DSLOWNUUMZVCAC-UHFFFAOYSA-N 0.000 claims description 2
- XXFXTBNFFMQVKJ-UHFFFAOYSA-N [diphenyl(trityloxy)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XXFXTBNFFMQVKJ-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001241 acetals Chemical class 0.000 claims description 2
- DQEFBVRIBYYPLE-UHFFFAOYSA-N anthracen-9-ylmethyl carbamate Chemical compound C1=CC=C2C(COC(=O)N)=C(C=CC=C3)C3=CC2=C1 DQEFBVRIBYYPLE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005002 aryl methyl group Chemical group 0.000 claims description 2
- 125000003609 aryl vinyl group Chemical group 0.000 claims description 2
- DUXANUSOCMOJSI-UHFFFAOYSA-N benzhydryl carbamate Chemical compound C=1C=CC=CC=1C(OC(=O)N)C1=CC=CC=C1 DUXANUSOCMOJSI-UHFFFAOYSA-N 0.000 claims description 2
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 2
- AWHNUHMUCGRKRA-UHFFFAOYSA-N benzylsulfonylmethylbenzene Chemical class C=1C=CC=CC=1CS(=O)(=O)CC1=CC=CC=C1 AWHNUHMUCGRKRA-UHFFFAOYSA-N 0.000 claims description 2
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- LWABFMLTBBNLTA-UHFFFAOYSA-N cyclobutyl carbamate Chemical compound NC(=O)OC1CCC1 LWABFMLTBBNLTA-UHFFFAOYSA-N 0.000 claims description 2
- OCDXZFSOHJRGIL-UHFFFAOYSA-N cyclohexyloxycyclohexane Chemical compound C1CCCCC1OC1CCCCC1 OCDXZFSOHJRGIL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005520 diaryliodonium group Chemical group 0.000 claims description 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N diethyl disulphide Natural products CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 claims description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 238000000059 patterning Methods 0.000 claims description 2
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 2
- RWUGBYOALBYTGU-UHFFFAOYSA-N pyridin-4-ylmethyl carbamate Chemical compound NC(=O)OCC1=CC=NC=C1 RWUGBYOALBYTGU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- FLCPORVHXQFBHT-UHFFFAOYSA-N quinolin-8-yl carbamate Chemical compound C1=CN=C2C(OC(=O)N)=CC=CC2=C1 FLCPORVHXQFBHT-UHFFFAOYSA-N 0.000 claims description 2
- 150000003871 sulfonates Chemical class 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- KJTULOVPMGUBJS-UHFFFAOYSA-N tert-butyl-[tert-butyl(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)O[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 KJTULOVPMGUBJS-UHFFFAOYSA-N 0.000 claims description 2
- LGSAOJLQTXCYHF-UHFFFAOYSA-N tri(propan-2-yl)-tri(propan-2-yl)silyloxysilane Chemical compound CC(C)[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)C(C)C LGSAOJLQTXCYHF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 claims description 2
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 claims description 2
- CALZWRITFOWNNV-UHFFFAOYSA-N 2-(2-phenylselanylethoxy)ethylselanylbenzene Chemical compound C=1C=CC=CC=1[Se]CCOCC[Se]C1=CC=CC=C1 CALZWRITFOWNNV-UHFFFAOYSA-N 0.000 claims 1
- JTSSUEWTRDWHGY-UHFFFAOYSA-N 4-(pyridin-4-ylmethoxymethyl)pyridine Chemical compound C=1C=NC=CC=1COCC1=CC=NC=C1 JTSSUEWTRDWHGY-UHFFFAOYSA-N 0.000 claims 1
- NTCIAFWCCFAZLW-UHFFFAOYSA-N 5,5-dibromo-1,3-dioxane Chemical class BrC1(Br)COCOC1 NTCIAFWCCFAZLW-UHFFFAOYSA-N 0.000 claims 1
- 238000012856 packing Methods 0.000 abstract description 8
- 230000003993 interaction Effects 0.000 abstract description 7
- 239000000243 solution Substances 0.000 description 20
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000005669 field effect Effects 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 239000010408 film Substances 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical class [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000012212 insulator Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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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
- H10K85/615—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
- 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
-
- 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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Definitions
- a thin film type field-effect transistor is a basic structure in micro-electronics.
- the FET includes three electrodes such as source electrodes, drain electrodes, and gate electrodes, an insulating layer, and a semiconductor layer.
- the semiconductor layer is a conductive channel between the source electrode and the drain electrode, the FET functions as a capacitor.
- the concentration of charge carrier is controlled by using voltage applied through the gate electrode, and thus the flow of electric charges between the source electrode and the drain electrode can be controlled by using voltage applied through the gate electrode.
- organic semiconductor substances are used in the FETs
- electronic devices may be manufactured by using a printing method such as screen printing, ink-jet printing, and micro-contact printing.
- a printing method such as screen printing, ink-jet printing, and micro-contact printing.
- an organic semiconductor substance may be used at a very low substrate temperature and no or little vacuum. Therefore, in respects to electronic devices, such as FETs, using an organic semiconductor substance, the manufacturing is easily achieved and manufacturing cost is low as compared to the case of when the inorganic semiconductor substance is used.
- Organic substances such as small molecules, polymers, and oligomers as that are used as organic semiconductor substances of FETs have been studied since the year 1980s. With respect to this, performance such as charge carrier mobility of the FETs is increased from 10 ⁇ 5 cmWs to 1 cnf/Vs (J. M. Shaw, P. F. Seidler, IBM J. Res. & Dev. , Vol. 45, 3 (2001)). Performance of the current organic transistor is higher than that of the amorphous silicon transistor. Thus, the organic transistor may be used in electronic papers, smart cards, memory devices, and display devices.
- a basic function of a field-effect transistor is to control the amount of current flowing between a source and a drain by using voltage appl ied to a gate.
- an organic semiconductor layer has crystal Unity.
- Most of known semiconductor substances that are used in an organic semiconductor layer have crystal Unity resulting from bonding force of van der Waals' force between organic semiconductor substance molecules.
- the van der Waals' force is very weak bonding force, which prevents desirable crystal Unity from being ensured or desirable organic films from being formed.
- the present invention provides anorganic thin film transistor that comprises an organic semiconductor layer containing an organic semiconductor substance having a functional group that can form a hydrogen bond.
- the present invention provides a method of manufacturing an organic thin film transistor, which comprises forming a gate electrode, an insulating layer, a source electrode, a drain electrode, and an organic semiconductor layer, wherein an organic semiconductor layer is formed by using a compound having a functional group that can form a hydrogen bond.
- the present invention provides a method of manufacturing an organic thin film transistor, which comprises forming a gate electrode, an insulating layer, a source electrode, a drain electrode, and an organic semiconductor layer wherein the organic semiconductor layer is formed by using a process that comprises forming a thin film by using the organic semiconductor substance in which a substituent group which is to be removed by using heat treatment or light treatment is added to the functional group of the organic semiconductor substance that can form the hydrogen bond, and then performing the heat treatment or the light treatment.
- the present invention provides an electronic device including the organic thin film transistor. [Advantageous Effects]
- an organic thin film transistor of the present invention According to a method of manufacturing an organic thin film transistor of the present invention, a solution process can be performed and an organic semiconductor layer that has strong bonding force due to hydrogen bonding and excellent crystal Unity can be formed. Therefore, an organic thin film transistor having high field effect mobility can be manufactured using the same.
- FIG.1 is a sectional view illustrating a bottom contact structure of an organic thin film transistor (101: substrate and gate, 102: source electrode, 103: drain electrode, 104: insulating layer (gate insulator), and 105: organic semiconductor layer);
- FIG. 2 is a sectional view illustrating a top contact structure of the organic thin film transistor (101: substrate and gate, 102: source electrode, 103: drain electrode, 104: insulating layer (gate insulator), and 105: organic semiconductor layer);
- FIG.3 illustrates an output curve when a compound of Formula 1 is deposited in a vacuum to form an organic semiconductor layer in the organic thin film transistor structure of FIG. 1
- FIG.4 illustrates an output curve when a compound of Formula 4 is subjected to spin coating to form an organic semiconductor layer in the organic thin film transistor structure of FIG. 1;
- FIG.5 is a UV-VIS spectrum of a thin film comprising the compound of Formula 4 which is prepared by using a solution process before and after heat treatment;
- FIG.6 is a graph illustrating the thermogravimetric analysis (TGA) results of the compound of Formula 4. [Best Mode]
- an organic semiconductor substance that is used to manufacture an organic thin film transistor is subjected to a packing process using interaction due to van der Waals 1 energy. Therefore, attraction force between molecules is not strong, thus bonding force between the molecules is weak, and the molecules are not sufficiently close to each other, so that movement of carriers between the molecules is not desirable on the transistor. Furthermore, air or moisture easily moves from the external into the semiconductor layer due to the undesirable packing between the molecules, thus reducing stability of devices.
- the organic semiconductor layer is formed by using a compound that can form a hydrogen bond having bonding force which is stronger than that of a van der Waals' bond between the molecules of the organic semiconductor substance in manufacturing the organic thin film transistor.
- hydrogen that is bonded to an atom having high electronegativity such as 0, N, S, and F interacts with unshared electron pairs of atoms such as 0, N, S, and F of adjacent other molecules to form a hydrogen bond.
- the hydrogen atom Since the electronegativity of each of 0, N, S, F and the like is much higher than that of a hydrogen atom, the hydrogen atom partially has a positive charge, and negative charges are partially generated in the atoms such as O, N, S, andF.
- the hydrogen atoms partially having the positive charge strongly attract the atoms having the negative charge such as oxygen, nitrogen, sulfur, and fluorine.
- packing is sufficiently performed between the molecules so that the different types of molecules are very close to each other, and the molecules are regularly arranged.
- the packing between the molecules reduces the distance between the molecules to desirably move carriers in the semiconductor layer.
- the organic semiconductor having the hydrogen bond can increase stability of electronic devices in respects to air or moisture.
- the organic semiconductor layer may be formed by using the compound having the functional group that can form the hydrogen bond according to a process known in the related art.
- examples of the process of forming the semiconductor layer during manufacturing of the organic thin film transistor include a vacuum deposition process and a solution coating process.
- the vacuum deposition process requires high temperatures and vacuum, which is difficult to form the layer having large area. Furthermore, equipment cost is relatively high and the process is relatively complicated.
- the solution coating process such as a spin coating process, an inkjet printing process, a dip coating process, a roll coating process, and a screen printing process can form the thin film layer having large area and be performed at normal temperature and pressure, thus reducing manufacturing cost.
- the present invention provides a method of forming an organic semiconductor layer by using a vacuum deposition process, wherein the organic semiconductor layer is formed by using the organic semiconductor substance containing the functional group that can form the hydrogen bond to increase packing between the molecules and crystal Unity, or a method of forming an organic semiconductor layer by using a solution process using anorganic semiconductor substance in which a bulky substituent is added to the functional group that can form the hydrogen bond to allow the organic solvent to easily penetrate the substance, thus increasing solubility of the organic semiconductor substance.
- the organic semiconductor layer of the organic thin fi Im transistor according to the present invention may be formed by using the organic semiconductor substance having the functional group that can form the hydrogen bond.
- the substituent group that is removed due to heat or light is added to the functional group of the compound, in which the functional group is bonded to a N, 0, S, or F atom and forms the hydrogen bond, so as to remove the hydrogen bond, thus reducing the interaction between the molecules.
- the substituent group can increase solubility, for example, the substituent group is bulky, solubility of the compound is increased, accordingly, the compound can be easily prepared in a solution form.
- the solution is used to form the thin film according to the solution coating process.
- the thin film is subjected to heat or light treatment to remove the substituent group, thereby producing the organic semiconductor substance which is capable of forming the hydrogen bond and has strong bonding force. Therefore, in the method of manufacturing the organic thin film transistor according to the present invention, even though the thin film is formed by using the solution process, the thin film has excellent packing between the molecules, crystal Unity, and stability to moisture or air due to the hydrogen bond.
- any type of compound may be used as the organic semiconductor substance having the functional group that can form the hydrogen bond as long as the compound can form the hydrogen bond and be used as a semiconductor substance.
- a detailed description will be given of examples of the compound that is used in the present invention, which are set forth to illustrate but are not to be construed to limit the present invention.
- the functional group may be a functional group of any one compound of compounds represented by Formulas 1,2, and 3.
- the compounds which are represented by Formulas 1 to 3, all have a ketone group and a NH group that can form a hydrogen bond.
- the groups form hydrogen bonds as shown in the following Structural formula 1 or 2, incurring strong interaction.
- the compounds having strong bonding force or the organic semiconductor substances containing the compounds may be used to form the organic semiconductor layer by using vacuum deposition.
- Ar and Ar 1 are each independently selected from the group consisting of an aryl group and ahetero aryl group, and may be subst ituted by an alkyl group, an alkoxy group, an acetyl group, a thioalkoxy group, an imine group, an ether group, an ester group, a nitrile group, an amino group, a thioester group, a nitro group or the like.
- Ar and Ar' are each independently selected from the group consisting of an aryl group and ahetero aryl group, and may be substituted by an alkyl group, an alkoxy group, an acetyl group, a thioalkoxy group, an imine group, an ether group, a nitrile group, an amino group, an ester group, a nitro group or the like.
- the compounds, which are represented by Formulas 4 and 5 do not form a hydrogen bond due to a very bulky substituent group. Thus, bonding force between the molecules is reduced and solubility is significantly increased, accordingly, the compounds can be prepared in a solution form. Therefore, the compounds can be used to form a thin film by using a solution process.
- the hydrogen atom is substituted by a t-butoxy carbonyl group and the bonds between the molecules may be broken due to heat or light treatment to form the substances of Formulas 1 and 3 again.
- Reaction Schemes 1 and 2 will explain the substitution of the compound represented by Formula 1 by the t-butoxy carbonyl group and the conversion of the substituted compound into the compound having the hydrogen bond due to heat.
- Reaction schemes are set forth to illustrate, but are not to be construed to limit the present invention.
- the product of Reaction Scheme 1 has solubi 1 ity that is much higher than that of quinacridone used as a starting substance.
- the product can be obtained in a solution form.
- the product is used to produce the solution and the thin film is formed by using the solution according to the solution process.
- the substituent t-butoxy carbonyl group may be decomposed into carbon dioxide and isopropene due to heat to be completely removed, and a quinacridone compound is produced again.
- the organic semiconductor substance in which other type of substituent group is added to the functional group of the organic semiconductor substance that can form the hydrogen bond, can convert into the compound that can form the hydrogen bond by light treatment as well as heat treatment.
- a photo acid generator PAG
- the photo acid generator is a substance that is used to perform patterning by using a photolithography process.
- the compound containing the t-butoxy carbonyl group or the like and the photo acid generator are mixed with each other to form the thin film and the thin film is then exposed to light by using a photomask, an acid is generated at an exposed portion of the thin film to remove the subst ituent group such as the t-butoxy carbonyl group.
- the hydrogen bond is regenerated and a difference in solubility of the thin film occurs due to the hydrogen bond. Therefore, the thin film can be patterned due to the difference in solubility.
- the compound, in which the other type of substituent group is added to the functional group forming the hydrogen bond is mixed with the photo acid generator to form the thin film and the thin film is then exposed to light to form the organic semiconductor layer including the compound that forms the hydrogen bond.
- the light treatment using the photo acid generator is useful to form patterned electronic devices.
- the content of the photo acid generator is not limited, but preferably less than 10% in respects to the organic semiconductor compound.
- Examples of the photo acid generator include, but are not limited to diaryliodonium salts, triarylsulfonium salts, imido sulfonates, 4-nitrobenzenesulfonic acid derivatives, disulphone compounds, sulfonyl substituted diazomethanes, and dibenzyl sulfones aryl-bis-trichloromethyl-s-triazine. They are decomposed due to light to generate protic acids.
- examples of the substituent group that is used instead of the functional group forming the hydrogen bond include, but are not limited to t-butoxy carbonyl which is the substituent group of the compounds represented by Formulas 4 and 5.
- an alcohol group, a phenol group, a catechol group, a carbonyl group, a thiol group, an amine group or the like that forms a hydrogen bond may be protected by using an ether bond, an ester bond, a thioether bond, a thioester bond, an amide bond or the like.
- the temperature and time of the heat treatment are not limited but selected according to the type of substituent groups.
- the temperature is preferably in the range of 20 to 350°C and the time is preferably in the range of 1 min to 2 hours. More preferably, the treatment is performed at the temperature of 150°C or less for 30 min or less.
- the exposure time is not limited but preferably less than 30 min.
- ultraviolet rays or visible rays are used as a light source.
- the wavelength thereof is not limited, but preferably in the range of 180 to 700 nm which is typically used.
- the heat treatment may be additionally performed.
- the temperature of the heat treatment is relatively low as compared to the case of when only the heat treatment is performed.
- examples of the substituent group that substitute for the alcohol group include methyl ether, methoxymethyl ether, methoxythiomethyl ether, 2-methoxyethoxymethyl ether, bis(2-chloroethoxy)methyl ether, tetrahydropyranyl ether, 4-methoxytetrahydropyranyl ether, tetrahydrothiopyranyl ether, 4-methoxytetrahydropyranyl ether, 4-methoxythetrahydrothiopyranyl ether, tetrahydrofuranyl ether, tetrahydrothiofuranyl ether, 1-ethoxyethyl ether, 1-methyl-l-methoxyethyl ether, 2-( ⁇ henylselenyl)ethyl ether, t-butyl ether, allyl ether, benzyl ether, o-nitrobenzyl ether, triphenylmethyl ether
- the functional group forming the hydrogen bond is an alcohol group
- substituent group that substitute for the alcohol group include trichloroacetate ester, methyl carbonate, 2,2,2-trichloroethyl carbonate, allyl carbonate, p-nitrophenyl carbonate, benzyl carbonate, s-benzyl thiocarbonate, nitrate ester, and 2,4-dinitrophenylsulfenate ester.
- the functional group forming the hydrogen bond is an alcohol group
- substituent group that substitute for the alcohol group include nitrate ester and 2,4-dinitrophenylsulfenate ester.
- examples of the substituent group that substitute for the phenol group or the catechol group include methyl ether, methoxymethyl ether, 2-methoxyethoxymethyl ether, methoxythiomethyl ether, penacyl ether, allyl ether, cyclohexyl ether, t-butyl ether, benzyl ether, o-nitrobenzyl ether, 9-anthrylmethyl ether, 4- ⁇ icolyl ether, t-butyldimethylsilyl ether, aryl acetate, aryl pivaloate, aryl benzoate, aryl 9-fluorenecarboxylate, aryl methyl carbonate, aryl 2,2,2-
- examples of the substituent group that substitute for the carbonyl group include dimethyl acetal and ketal , bis(2,2,2-trichloroethyl) acetal and ketal, 1,3-dioxanes, 5-methylene-l,3-dioxanes, 5,5-dibromo-l,3-dioxanes, 1,3—dioxo1anes, 4-bromomethy1-1,3—dioxo1anes,
- examples of the substituent group that substitute for the thiol group include s-benzyl thioether, s-p-methoxybenzyl thioether, s-p-nitrobenzyl thioether, s-4-picolyl thioether, s-2-picolyl N-oxide thioether, s-9-anthrylmethyl thioether, s-diphenylmethyl thioether, s-di(p-methoxyphenyl)methyl dithioether, s-triphenylmethyl thioether, s-2,4-dinitrophenyl thioether, s-t-butyl thioether, s-isobutoxymethyl monothioacetal , s-2-tetrahydropiranyl monothioacetal , s-acetamidomethyl aminothioacetal , s-cyanomethyl thioether,
- examples of the substituent group that substitute for the amine group include methyl carbamate, 9-fluorenylmethyl carbamate, 2,2,2-trichloroethyl carbamate, 2-trimethylsilylethyl carbamate, 1,1-dimethylpropynyl carbamate, 1-methyl-l-phenylethyl catbamate, l-methyl-l-(4-biphenylyl)ethyl carbamate, l,l-dimethyl-2-haloethyl carbamate, l,l-dimethyl-2-cyanoethyl carbamate, t-butyl carbamate, cyclobutyl carbamate, 1-methylcyclobutyl carbamate, 1-adamantyl carbamate, vinyl carbamate, al IyI carbamate, cinnamyl carbamate, 8-quinolyl carbamate, N-hydroxypiperidinyl carbamate
- the functional group forming the hydrogen bond is the amine group
- the substituent group that substitute for the amine group include l,l-dimethyl-2-haloethyl carbamate, l,l-dimethyl-2-cyanoethyl carbamate, t-butyl carbamate, and (N-(N'-acetylmethiony1)) .
- the functional group forming the hydrogen bond is the amine group
- substituent group that substitute for the amine group include l,l-dimethyl-2-haloethyl carbamate and t-butyl carbamate.
- the functional group forming the hydrogen bond is the amine group
- most preferable examples of the substituent group include t-butyl carbamate.
- the compound having the functional group that forms the hydrogen bond protected by the above-mentioned substituent group may be used as the organic semiconductor substance in itself.
- preferable examples of the compound having the functional group that forms the hydrogen bond include a compound containing thiophene derivatives, acene derivatives, and porphyrinic derivatives having organic semiconductor properties.
- the compounds represented by Formulas 6 to 16 may be used to improve the organic semiconductor properties. The following examples are set forth to illustrate, but are not to be construed to limit the present invention.
- n andm are each independently 0 or a positive integer
- R and R 1 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
- n and m are in the range of 0 to 10.
- n and n 1 are each independently 0 or a positive integer
- m is a positive integer
- R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
- n and n' are each independently in the range of 0 to 10 and m is in the range of 1 to 100.
- n andm are each independently 0 or a positive integer
- Rl to R18 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialky1si 1y1 acetyl group, an ether group, an amino group, an imine group, an ester group, a nitrile group, a thioalkoxy group, a thioester group, a vinyl group, an aryl group, and a hetero group.
- n and m are each independently in the range of 0 to 3.
- n andm are each independently 0 or a positive integer
- R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
- n and m are each independently in the range of 0 to 10.
- n and m are each independently 0 or a positive integer
- Rl to R18 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
- n and m are each independently in the range of 0 to 3.
- n is 0 or a positive integer.
- n is in the range of 0 to 10.
- n O or a positive integer
- Rl to R8 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, anitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
- n is in the range of 0 to 3.
- n is 0 or a positive integer
- m is a positive integer
- Rl to R8 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
- n is in the range of 0 to 3 and m is in the range of 1 to 100.
- n and m are each independently 0 or a positive integer
- R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ester group, an ether group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
- n and m are in the range of 0 to 10.
- n and m are each independently 0 or a positive integer
- Rl to R18 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
- n and m are each independently in the range of 0 to 3.
- R and R' are each independently any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to
- A is a connection group and any one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an ether group having 1 to 20 carbon atoms, a thioether group, an aryl group, a hetero aryl group, a vinyl group, and an acetyl group, n is a positive integer and preferably in the range of 1 to 10, 1 and m are each independently 0 or a positive integer and preferably in the range of 0 to 10, and k is a positive integer and preferably in the range of 1 to 100.
- the compounds representd by Formulas 6 to 16 may form monomer compounds or polymer compounds.
- the thiophene derivatives or the acene derivatives may be substituted by an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, a hetero group, etc.
- the alkyl group, the alkoxy group, the ether group, the ester group, the thioalkoxy group, the vinyl group, the aryl group, and the hetero group that are used in the present invention may be each an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an ether group having 1 to 20 carbon atoms, an ester group having 1 to 20 carbon atoms, a thioalkoxy group having 1 to 20 carbon atoms, a thioester group having 1 to 20 carbon atoms, a vinyl group having 2 to 20 carbon atoms, an aryl group having 6 to 60 carbon atoms and preferably 6 to 16 carbon atoms, and a heterocyclic compound having 4 to 60 carbon atoms and preferably 4 to 12 carbon atoms.
- the organic thin film transistor according to the present invention may be manufactured by using a material, a structure, and a process that are known in the related art, except the above-mentioned material and process.
- the OTFT according to the present invention includes an organic semiconductor layer, a gate electrode, a gate insulating film, a source electrode, and a drain electrode.
- the organic thin film transistor may further include a substrate on a lower surface of the gate electrode.
- FIGS. 1 and 2 illustrate the structure of the organic thin film transistor according to the present invention.
- the organic thin film transistor of FIG.1 is provided herein for purpose of illustration only and is not intended to be limiting unless otherwise specified, and the organic thin film transistor of the present invention may have various types of structures without departing from the spirit of the present invention.
- Examples of the substrate include, but are not limited to flexible materials such as plastics and papers and inorganic material such as silicon and glass.
- the gate electrode may be made of a conductive substance.
- Illustrating, but non-limiting examples of the conductive substance include carbon, aluminium, vanadium, chrome, copper, zinc, silver, gold, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, tin, lead, similar metals, alloys of the metals, p- or n-doped silicon, zinc oxides, indium oxides, indium tin oxides (ITO), indium zinc oxides, and similar tin oxides, mixtures of oxides and metals such as tin oxide indium-based complex compounds, ZnO:Al and Sn(VSb, and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-l,2-dioxy)thiophene] , polypyrrole, and polyaniline.
- the gate insulating film may be made of the insulating substance.
- Illustrating, but non-limiting examples of the insulating substance include silicon oxides, silicon nitrides, and plastic insulators such as polyimide, poly(2-vinylpyridine), poly(4-vinylphenol), and polymethylmethacrylate.
- Examples of the material used to manufacture the source, drain, and gate electrodes include, but are not limited to metal such as gold (Au), platinum (Pt), silver (Ag), palladium (Pd), aluminium (Al), nickel (Ni), and chrome (Cr), conductive metal oxides such as indium tin oxides, indium zinc oxides, and nickel oxides, and conductive polymers such as polyaniline, polypyrrole, and polyethylenedioxythiophene.
- the present invention provides an electronic device that includes the organic thin film transistor. Examples of the electronic device include electronic papers, smart cards, memory devices, and display devices.
- FIG.6 illustrates the thermogravimetric analysis (TGA) results of the compound of Formula 4, and it can be seen that the substituent suppressing the hydrogen bond is removed due to heat at 200°C or less.
- the n-type dopped silicon wafer having low resistance was used as the gate electrode, and the gate insulating film that was made of SiU2 and had a thickness of 3000 A was layered thereon by using a heat oxidation process.
- gold was applied to a thickness of 500 A by using a photol ithography process to form a source-drain electrode having a channel length of 10 ⁇ m and a channel width of 300 ⁇ m.
- the substrate was subjected to surface treatment by using a UV-ozone plasma, HMDS (hexamethyldisilazane) was applied thereon by spin coating at 3000 rpm for 30 sec, and baking was performed at 120"C for 2 min.
- HMDS hexamethyldisilazane
- quinacridone represented by Formula 1 was deposited in a vacuum at a rate of 0.3 A/s to produce a channel substance in a thickness of 500 A.
- the organic thin film transistor which was manufactured by using the above-mentioned procedure had field effect mobility of 7.94 x 10 ⁇ 5 cmVVs. This is shown in FIG.3.
- the n ⁇ type doped silicon wafer having low resistance was used as the gate electrode, and the gate insulating film that was made of Si ⁇ 2 and had a thickness of 3000 A was layered thereon by using a heat oxidation process.
- gold was applied to a thickness of 500 A by using a photo1ithographyprocess to form a source-drain electrode having a channel length of 10 ⁇ m and a channel width of 300 ⁇ m.
- the substrate was subjected to surface treatment by using a UV-ozone plasma, HMDS (hexamethyldisilazane) was applied thereon by spin coating at 3000 rpm for 30 sec, and baking was performed at 120°C for 2 min.
- HMDS hexamethyldisilazane
- the solution that was prepared by dissolving the compound represented by Formula 4 of Preparation Example 1 in tetrachloroethane to have a concentration of 2 w/w% was applied by spin coating at 1500 rpm for 20 sec and drying was performed at 50 ° C for 1 min and at 180°C for 2 min to manufacture the organic thin film transistor.
- the organic thin film transistor which was manufactured by using the above-mentioned procedure had field effect mobility of 1.84 x 10 ⁇ 5 cmVVs. This is shown in FIG. 4.
- the field effect mobility of the organic thin film transistor that was manufactured by using the organic semiconductor layer formed through the solution process were relatively lower than that of the organic thin film transistor that was manufactured by using the semiconductor layer formed through the vacuum deposition, but a difference in properties was not significant. Therefore, it can be seen that the organic thin film transistor can be efficiently manufactured by regenerating the hydrogen bond.
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Abstract
The present invention relates to an organic thin film transistor that includes an organic semiconductor layer containing an organic semiconductor substance having a functional group that can form a hydrogen bond, and a method of manufacturing the same. In the organic thin film transistor, a semiconductor substance having a functional group that can form a hydrogen bond is used as an organic semiconductor substance, thus improving a packing property due to maximized interaction between the molecules. Since an organic semiconductor layer is formed by using a solution process, manufacturing cost is reduced.
Description
[DESCRIPTION] [Invention Title]
ORGANIC TFTS AND METHOD FOR FABRICATING THE SAME [Technical Field] The present invention relates to an organic thin film transistor and a method for fabricating the same. This application claims priority from Korea Patent Application No. 10-2006-70933 filed on July 27, 2006 in the KIPO, the disclosure of which is incorporated herein by reference in its entirety. [Background Art]
A thin film type field-effect transistor (FET) is a basic structure in micro-electronics. The FET includes three electrodes such as source electrodes, drain electrodes, and gate electrodes, an insulating layer, and a semiconductor layer. In the FET, if the semiconductor layer is a conductive channel between the source electrode and the drain electrode, the FET functions as a capacitor. In the channel, the concentration of charge carrier is controlled by using voltage applied through the gate electrode, and thus the flow of electric charges between the source electrode and the drain electrode can be controlled by using voltage applied through the gate electrode.
Currently, a concern for development of FETs using organic semiiicionductor substances is growing. If the organic semiconductor substances are used in the FETs, electronic devices may be manufactured by using a printing method such as screen printing, ink-jet printing, and micro-contact printing. Unlike a known inorganic semiconductor substance, an organic semiconductor substance may be used at a very low substrate temperature and no or little vacuum. Therefore, in respects to electronic devices, such as FETs, using an organic semiconductor substance, the manufacturing is easily achieved and manufacturing cost is low as compared to the case of when the inorganic semiconductor substance is used.
Organic substances such as small molecules, polymers, and oligomers as that are used as organic semiconductor substances of FETs have been studied since the year 1980s. With respect to this, performance such as charge carrier mobility of the FETs is increased from 10~5 cmWs to 1 cnf/Vs (J. M. Shaw, P. F. Seidler, IBM J. Res. & Dev. , Vol. 45, 3 (2001)). Performance of the current organic transistor is higher than that of the amorphous silicon transistor. Thus, the organic transistor may be used in electronic papers, smart cards, memory devices, and display devices.
A basic function of a field-effect transistor is to control the amount of current flowing between a source and a drain by using voltage appl ied to a gate. In order to achieve this, resistance of a semiconductor layer needs to significantly change according to the gate voltage. Therefore, in order to satisfy the need, it is considered to be preferable that an organic semiconductor layer has crystal Unity. Most of known semiconductor substances that are used in an organic semiconductor layer have crystal Unity resulting from bonding force of van der Waals' force between organic semiconductor substance molecules. However, the van der Waals' force is very weak bonding force, which prevents desirable crystal Unity from being ensured or desirable organic films from being formed.
When the organic semiconductor substances are used in electronic devices, organic substances need to have electric charges in operation. However, since the organic substances having the electric charges are vulnerable to moisture and air, it is difficult to manufacture stable devices that are suitable for the commercial purpose. [Disclosure] [Technical Problem] The present inventors found that when an organic semiconductor
layer of an organic thin film transistor is made of an organic semiconductor substance having a functional group that can form a hydrogen bond, a packing propertybetweenmolecules can be improved due to maximized interaction between the molecules. Therefore, it is an object of the present invention to provide an organic thin film transistor using an organic semiconductor substance having a functional group that can form a hydrogen bond and a method for fabricating the same. [Technical Solution]
The present invention provides anorganic thin film transistor that comprises an organic semiconductor layer containing an organic semiconductor substance having a functional group that can form a hydrogen bond.
Furthermore, the present invention provides a method of manufacturing an organic thin film transistor, which comprises forming a gate electrode, an insulating layer, a source electrode, a drain electrode, and an organic semiconductor layer, wherein an organic semiconductor layer is formed by using a compound having a functional group that can form a hydrogen bond.
Furthermore, the present invention provides a method of manufacturing an organic thin film transistor, which comprises forming
a gate electrode, an insulating layer, a source electrode, a drain electrode, and an organic semiconductor layer wherein the organic semiconductor layer is formed by using a process that comprises forming a thin film by using the organic semiconductor substance in which a substituent group which is to be removed by using heat treatment or light treatment is added to the functional group of the organic semiconductor substance that can form the hydrogen bond, and then performing the heat treatment or the light treatment.
Furthermore, the present invention provides an electronic device including the organic thin film transistor. [Advantageous Effects]
According to a method of manufacturing an organic thin film transistor of the present invention, a solution process can be performed and an organic semiconductor layer that has strong bonding force due to hydrogen bonding and excellent crystal Unity can be formed. Therefore, an organic thin film transistor having high field effect mobility can be manufactured using the same. [Description of Drawings]
FIG.1 is a sectional view illustrating a bottom contact structure of an organic thin film transistor (101: substrate and gate, 102: source
electrode, 103: drain electrode, 104: insulating layer (gate insulator), and 105: organic semiconductor layer);
FIG. 2 is a sectional view illustrating a top contact structure of the organic thin film transistor (101: substrate and gate, 102: source electrode, 103: drain electrode, 104: insulating layer (gate insulator), and 105: organic semiconductor layer);
FIG.3 illustrates an output curve when a compound of Formula 1 is deposited in a vacuum to form an organic semiconductor layer in the organic thin film transistor structure of FIG. 1; FIG.4 illustrates an output curve when a compound of Formula 4 is subjected to spin coating to form an organic semiconductor layer in the organic thin film transistor structure of FIG. 1;
FIG.5 is a UV-VIS spectrum of a thin film comprising the compound of Formula 4 which is prepared by using a solution process before and after heat treatment; and
FIG.6 is a graph illustrating the thermogravimetric analysis (TGA) results of the compound of Formula 4. [Best Mode]
A detailed description of the present invention will be given hereinafter.
Generally, an organic semiconductor substance that is used to manufacture an organic thin film transistor is subjected to a packing process using interaction due to van der Waals1 energy. Therefore, attraction force between molecules is not strong, thus bonding force between the molecules is weak, and the molecules are not sufficiently close to each other, so that movement of carriers between the molecules is not desirable on the transistor. Furthermore, air or moisture easily moves from the external into the semiconductor layer due to the undesirable packing between the molecules, thus reducing stability of devices. In order to avoid the above-mentioned disadvantages, in the present invention, the organic semiconductor layer is formed by using a compound that can form a hydrogen bond having bonding force which is stronger than that of a van der Waals' bond between the molecules of the organic semiconductor substance in manufacturing the organic thin film transistor. Generally, hydrogen that is bonded to an atom having high electronegativity such as 0, N, S, and F interacts with unshared electron pairs of atoms such as 0, N, S, and F of adjacent other molecules to form a hydrogen bond. Since the electronegativity of each of 0, N, S, F and the like is much higher than that of a hydrogen atom, the hydrogen atom
partially has a positive charge, and negative charges are partially generated in the atoms such as O, N, S, andF. The hydrogen atoms partially having the positive charge strongly attract the atoms having the negative charge such as oxygen, nitrogen, sulfur, and fluorine. Thus, packing is sufficiently performed between the molecules so that the different types of molecules are very close to each other, and the molecules are regularly arranged. The packing between the molecules reduces the distance between the molecules to desirably move carriers in the semiconductor layer. Furthermore, the organic semiconductor having the hydrogen bond can increase stability of electronic devices in respects to air or moisture.
In the organic thin film transistor according to the present invention, the organic semiconductor layer may be formed by using the compound having the functional group that can form the hydrogen bond according to a process known in the related art. In general, examples of the process of forming the semiconductor layer during manufacturing of the organic thin film transistor include a vacuum deposition process and a solution coating process. The vacuum deposition process requires high temperatures and vacuum, which is difficult to form the layer having large area. Furthermore, equipment
cost is relatively high and the process is relatively complicated. However, the solution coating process such as a spin coating process, an inkjet printing process, a dip coating process, a roll coating process, and a screen printing process can form the thin film layer having large area and be performed at normal temperature and pressure, thus reducing manufacturing cost.
However, in a compound having strong interaction between the molecules, penetration of an organic solvent into the molecules of the compound is interrupted, thus reducing solubility of the compound. Therefore, in order to use an advantage of the hydrogen bonds between the organic semiconductor substances during the manufacturing of the organic thin film transistor, the present invention provides a method of forming an organic semiconductor layer by using a vacuum deposition process, wherein the organic semiconductor layer is formed by using the organic semiconductor substance containing the functional group that can form the hydrogen bond to increase packing between the molecules and crystal Unity, or a method of forming an organic semiconductor layer by using a solution process using anorganic semiconductor substance in which a bulky substituent is added to the functional group that can form the
hydrogen bond to allow the organic solvent to easily penetrate the substance, thus increasing solubility of the organic semiconductor substance.
In detai 1 , the organic semiconductor layer of the organic thin fi Im transistor according to the present invention may be formed by using the organic semiconductor substance having the functional group that can form the hydrogen bond.
That is, the substituent group that is removed due to heat or light is added to the functional group of the compound, in which the functional group is bonded to a N, 0, S, or F atom and forms the hydrogen bond, so as to remove the hydrogen bond, thus reducing the interaction between the molecules. In particular, if the substituent group can increase solubility, for example, the substituent group is bulky, solubility of the compound is increased, accordingly, the compound can be easily prepared in a solution form. The solution is used to form the thin film according to the solution coating process. Subsequently, the thin film is subjected to heat or light treatment to remove the substituent group, thereby producing the organic semiconductor substance which is capable of forming the hydrogen bond and has strong bonding force. Therefore,
in the method of manufacturing the organic thin film transistor according to the present invention, even though the thin film is formed by using the solution process, the thin film has excellent packing between the molecules, crystal Unity, and stability to moisture or air due to the hydrogen bond.
In the present invention, any type of compound may be used as the organic semiconductor substance having the functional group that can form the hydrogen bond as long as the compound can form the hydrogen bond and be used as a semiconductor substance. Hereinafter, a detailed description will be given of examples of the compound that is used in the present invention, which are set forth to illustrate but are not to be construed to limit the present invention.
In the organic semiconductor substance having the functional group that can form a hydrogen bond, the functional group may be a functional group of any one compound of compounds represented by Formulas 1,2, and 3.
The compounds, which are represented by Formulas 1 to 3, all have a ketone group and a NH group that can form a hydrogen bond. The groups form hydrogen bonds as shown in the following Structural formula 1 or 2,
incurring strong interaction. Thus, the compounds having strong bonding force or the organic semiconductor substances containing the compounds may be used to form the organic semiconductor layer by using vacuum deposition.
[Formula 1]
[Formula 2]
[Formula 3]
For Formula 3, preferably, Ar and Ar1 are each independently
selected from the group consisting of an aryl group and ahetero aryl group, and may be subst ituted by an alkyl group, an alkoxy group, an acetyl group, a thioalkoxy group, an imine group, an ether group, an ester group, a nitrile group, an amino group, a thioester group, a nitro group or the like.
Structural formula 1>
Structural formula 2>
In the compound that forms the hydrogen bond, when a hydrogen atom forming the hydrogen bond is substituted by a bulky substituent group such as a t-butoxycarbony1 group, the compound of Formula 4 or 5 that cannot
form a hydrogen bond is obtained.
[Formula 4]
[Formula 5]
For Formula 5, preferably, Ar and Ar' are each independently selected from the group consisting of an aryl group and ahetero aryl group, and may be substituted by an alkyl group, an alkoxy group, an acetyl group, a thioalkoxy group, an imine group, an ether group, a nitrile group, an amino group, an ester group, a nitro group or the like.
The compounds, which are represented by Formulas 4 and 5, do not form a hydrogen bond due to a very bulky substituent group. Thus, bonding force between the molecules is reduced and solubility is significantly
increased, accordingly, the compounds can be prepared in a solution form. Therefore, the compounds can be used to form a thin film by using a solution process. In the compounds represented by Formulas 4 and 5, the hydrogen atom is substituted by a t-butoxy carbonyl group and the bonds between the molecules may be broken due to heat or light treatment to form the substances of Formulas 1 and 3 again.
In detail, Reaction Schemes 1 and 2 will explain the substitution of the compound represented by Formula 1 by the t-butoxy carbonyl group and the conversion of the substituted compound into the compound having the hydrogen bond due to heat. However, Reaction schemes are set forth to illustrate, but are not to be construed to limit the present invention.
<Reaction Scheme 1>
<Reaction Scheme 2>
CO,
The product of Reaction Scheme 1 has solubi 1 ity that is much higher than that of quinacridone used as a starting substance. Thus, the product can be obtained in a solution form. The product is used to produce the solution and the thin film is formed by using the solution according to the solution process. Additionally, the substituent t-butoxy carbonyl group may be decomposed into carbon dioxide and isopropene due to heat to be completely removed, and a quinacridone compound is produced again.
The organic semiconductor substance, in which other type of substituent group is added to the functional group of the organic semiconductor substance that can form the hydrogen bond, can convert into the compound that can form the hydrogen bond by light treatment as well as heat treatment. Thus, in order to use the light treatment, it is preferable to use a photo acid generator (PAG) in conjunction with the compound, in which other type of substituent group is added to the functional group that can form the hydrogen bond, during the formation of the thin film. Generally, the photo acid generator is a substance that
is used to perform patterning by using a photolithography process. In detail , if the compound containing the t-butoxy carbonyl group or the like and the photo acid generator are mixed with each other to form the thin film and the thin film is then exposed to light by using a photomask, an acid is generated at an exposed portion of the thin film to remove the subst ituent group such as the t-butoxy carbonyl group. Thus, the hydrogen bond is regenerated and a difference in solubility of the thin film occurs due to the hydrogen bond. Therefore, the thin film can be patterned due to the difference in solubility. In the present invention, the compound, in which the other type of substituent group is added to the functional group forming the hydrogen bond, is mixed with the photo acid generator to form the thin film and the thin film is then exposed to light to form the organic semiconductor layer including the compound that forms the hydrogen bond. The light treatment using the photo acid generator is useful to form patterned electronic devices. The content of the photo acid generator is not limited, but preferably less than 10% in respects to the organic semiconductor compound.
Examples of the photo acid generator include, but are not limited
to diaryliodonium salts, triarylsulfonium salts, imido sulfonates, 4-nitrobenzenesulfonic acid derivatives, disulphone compounds, sulfonyl substituted diazomethanes, and dibenzyl sulfones aryl-bis-trichloromethyl-s-triazine. They are decomposed due to light to generate protic acids.
The reformation of molecules having the hydrogen bond by using heat or light is frequently used in protection and deprotection of the functional group in an organic chemical reaction field. In this connection, examples of the substituent group that is used instead of the functional group forming the hydrogen bond include, but are not limited to t-butoxy carbonyl which is the substituent group of the compounds represented by Formulas 4 and 5. In general, an alcohol group, a phenol group, a catechol group, a carbonyl group, a thiol group, an amine group or the like that forms a hydrogen bond may be protected by using an ether bond, an ester bond, a thioether bond, a thioester bond, an amide bond or the like.
When the hydrogen bonding occurs again by heat or light treating the substituents, the temperature and time of the heat treatment are not limited but selected according to the type of substituent groups. For
example, the temperature is preferably in the range of 20 to 350°C and the time is preferably in the range of 1 min to 2 hours. More preferably, the treatment is performed at the temperature of 150°C or less for 30 min or less. During the light treatment, the exposure time is not limited but preferably less than 30 min.
In addition, if the photo acid generator is used, ultraviolet rays or visible rays are used as a light source. The wavelength thereof is not limited, but preferably in the range of 180 to 700 nm which is typically used.
Further, in the case of when the light treatment is performed by using the photo acid generator, the heat treatment may be additionally performed. In this case, the temperature of the heat treatment is relatively low as compared to the case of when only the heat treatment is performed.
The substituent groups that are useful for the functional groups forming the hydrogen bond will be described below.
If the functional group forming the hydrogen bond is an alcohol group, examples of the substituent group that substitute for the alcohol
group include methyl ether, methoxymethyl ether, methoxythiomethyl ether, 2-methoxyethoxymethyl ether, bis(2-chloroethoxy)methyl ether, tetrahydropyranyl ether, 4-methoxytetrahydropyranyl ether, tetrahydrothiopyranyl ether, 4-methoxytetrahydropyranyl ether, 4-methoxythetrahydrothiopyranyl ether, tetrahydrofuranyl ether, tetrahydrothiofuranyl ether, 1-ethoxyethyl ether, 1-methyl-l-methoxyethyl ether, 2-(ρhenylselenyl)ethyl ether, t-butyl ether, allyl ether, benzyl ether, o-nitrobenzyl ether, triphenylmethyl ether, a-naphthyldiphenylmethyl ether, p-methoxyphenyldiphenylmethyl ether, 9-(9-ρhenyl-10-oxo)anthryl ether, trimethylsilyl ether, isopropyldimethylsilyl ether, t-butyldimethylsilyl ether, t-butyldiphenylsilyl ether, tribenzylsilyl ether, triisopropylsilyl ether, formate ester, acetate ester, trichloroacetate ester, phenoxyacetate ester, isobutyrate ester, pivaloate ester, adamantoate ester, benzoate ester, 2,4,6-trimethylbenzoate ester, methyl carbonate, 2,2,2-trichloroethyl carbonate, allyl carbonate, p-nitrophenyl carbonate, benzyl carbonate, s-benzyl thiocarbonate, N-phenyl carbonate, nitrate ester, 2,4-dinitrophenylsulfenate ester, etc.
If the functional group forming the hydrogen bond is an alcohol
group, preferable examples of the substituent group that substitute for the alcohol group include trichloroacetate ester, methyl carbonate, 2,2,2-trichloroethyl carbonate, allyl carbonate, p-nitrophenyl carbonate, benzyl carbonate, s-benzyl thiocarbonate, nitrate ester, and 2,4-dinitrophenylsulfenate ester.
If the functional group forming the hydrogen bond is an alcohol group, more preferable examples of the substituent group that substitute for the alcohol group include nitrate ester and 2,4-dinitrophenylsulfenate ester. If the functional group forming the hydrogen bond is the phenol group or the catechol group, examples of the substituent group that substitute for the phenol group or the catechol group include methyl ether, methoxymethyl ether, 2-methoxyethoxymethyl ether, methoxythiomethyl ether, penacyl ether, allyl ether, cyclohexyl ether, t-butyl ether, benzyl ether, o-nitrobenzyl ether, 9-anthrylmethyl ether, 4-ρicolyl ether, t-butyldimethylsilyl ether, aryl acetate, aryl pivaloate, aryl benzoate, aryl 9-fluorenecarboxylate, aryl methyl carbonate, aryl 2,2,2-trichloroethyl carbonate, aryl vinyl carbonate, aryl benzyl carbonate, aryl methanesulfonate, methylenedioxy derivatives, acetonide
derivatives, diphenylmethylenedioxy derivatives, cyclic borate, and cyclic carbonate.
If the functional group forming the hydrogen bond is carbonyl , examples of the substituent group that substitute for the carbonyl group include dimethyl acetal and ketal , bis(2,2,2-trichloroethyl) acetal and ketal, 1,3-dioxanes, 5-methylene-l,3-dioxanes, 5,5-dibromo-l,3-dioxanes, 1,3—dioxo1anes, 4-bromomethy1-1,3—dioxo1anes,
4-o-nitrophenyl-l,3-dioxolanes, S,S'-dimethyl acetal and ketal, 1,3-dithianes, 1,3-dithiolane, 1,3-oxathiolanes, o-trimethylsilyl cyanohydrins, N,N-dimethylhydrazones, 2,4-dinitrophenylhydrazones, o-phenylthiomethyl oximes, substituted methylene derivatives, bismethylenedioxy derivatives, methyl ester, methoxymethyl ester, methylthiomethyl ester, tetrahydropiranyl ester, benzyloxymethyl ester, penacyl ester, N-phthalimidomethyl ester, 2,2,2-trichloroethyl ester, 2-haloethyl ester, 2-(p-toluenesulfonyl)ethyl ester, t-butyl ester, cinnamyl ester, benzyl ester, triphenylmethyl ester, bis(o-nitrophenyl)methyl ester, 9-anthrylmethyl ester, 2-(9,10-dioxo)anthrylmethyl ester, piperonyl ester, trimethylsilyl ester, t-butyldimethylsilyl ester, s-t-butyl ester, 2-alkyl-l,3-oxazolines,
N,N-dimethylamide, N-7-nitroindoylamide, hydrazide, N-phenylhydrazide, and N,N'-diisopropylhydrizide.
If the functional group forming the hydrogen bond is the thiol group, examples of the substituent group that substitute for the thiol group include s-benzyl thioether, s-p-methoxybenzyl thioether, s-p-nitrobenzyl thioether, s-4-picolyl thioether, s-2-picolyl N-oxide thioether, s-9-anthrylmethyl thioether, s-diphenylmethyl thioether, s-di(p-methoxyphenyl)methyl dithioether, s-triphenylmethyl thioether, s-2,4-dinitrophenyl thioether, s-t-butyl thioether, s-isobutoxymethyl monothioacetal , s-2-tetrahydropiranyl monothioacetal , s-acetamidomethyl aminothioacetal , s-cyanomethyl thioether, s-2-nitro-l-phenylethyl thioether, s-2,2-bis(carboethoxy)ethyl thioether, s-benzoyl derivatives, s-(N-ethylcarbamate), and s-ethyl disulfide.
If the functional group forming the hydrogen bond is the amine group, examples of the substituent group that substitute for the amine group include methyl carbamate, 9-fluorenylmethyl carbamate, 2,2,2-trichloroethyl carbamate, 2-trimethylsilylethyl carbamate, 1,1-dimethylpropynyl carbamate, 1-methyl-l-phenylethyl catbamate, l-methyl-l-(4-biphenylyl)ethyl carbamate, l,l-dimethyl-2-haloethyl
carbamate, l,l-dimethyl-2-cyanoethyl carbamate, t-butyl carbamate, cyclobutyl carbamate, 1-methylcyclobutyl carbamate, 1-adamantyl carbamate, vinyl carbamate, al IyI carbamate, cinnamyl carbamate, 8-quinolyl carbamate, N-hydroxypiperidinyl carbamate, 4,5-diphenyl-3-oxazoline-2-one, benzyl carbamate, p-nitrobenzyl carbamate, 3,4-dimethoxy-6-nitrobenzyl carbamate, 2,4-dichlorobenzyl carbamate, 5-benzisoxazolylmethyl carbamate, 9-anthrylmethyl carbamate, diphenylmethyl carbamate, isonicotinyl carbamate, s-benzyl carbamate, N-(N'-phenylaminothiocarbonyl) derivatives, N-formyl , N-acetyl , N-chloroacetyl , N-trichloroacetyl , N-trifluoroacetyl , N-o-nitrophenylacetyl, N-o-nitrophenoxyacetyl , N-acetoacetyl , N-3-pheny1propiony1 , N-3-(p-hydroxypheny1 )propiony1 ,
N-2-methyl-2-(o-nitrophenoxy)propionyl , N-2-methyl-2-(o-phenylazophenoxy)propionyl , N-4-chlorobutyryl , N-o-nitrocinnamoyl, N-picolinoyl , N-(N'-acetylmethionyl , N-benzoyl , N-phthaloyl, N-dithiasuccinoyl , N-allyl, N-phenacyl , N-3-acetoxypropyl , quaternary ammonium salt, N-methoxymethyl , N-benzyloxymethyl , N-pivaloyloxymethyl , N-tetrahydropyranyl , N-2,4-dinitrophenyl , N-benzyl , N-o-nitrobenzyl , N-di(p-methoxyphenyl)methyl , N-triphenylmethyl ,
N-(p-methoxyphenyl) diphenylmethyl , N-diphenyl-4-pyridylmethyl , N-2-picolyl N'-oxide, N,N'-isopropylidene, N-benzylidene, N-p-nitrobenzylidene, N-salicylidene,
N-Cδ.δ-dimethyl-S-oxo-l-cyclohexenyl, N-nitro, N-oxide, N-diphenylphosphinyl , N-dimethylthiophosphinyl , N-benzenesulfenyl , N-o-nitrobenzenesulfenyl , N-2,4,6-trimethylbenzenesulfonyl , N-toluenesulfonyl , N-benzylsulfonyl , N-trifluoromethylsulfonyl , and N-phenacyl sulfonyl.
If the functional group forming the hydrogen bond is the amine group, preferable examples of the substituent group that substitute for the amine group include l,l-dimethyl-2-haloethyl carbamate, l,l-dimethyl-2-cyanoethyl carbamate, t-butyl carbamate, and (N-(N'-acetylmethiony1)) .
If the functional group forming the hydrogen bond is the amine group, more preferable examples of the substituent group that substitute for the amine group include l,l-dimethyl-2-haloethyl carbamate and t-butyl carbamate.
If the functional group forming the hydrogen bond is the amine group, most preferable examples of the substituent group include t-butyl
carbamate.
The compound having the functional group that forms the hydrogen bond protected by the above-mentioned substituent group may be used as the organic semiconductor substance in itself. Furthermore, preferable examples of the compound having the functional group that forms the hydrogen bond include a compound containing thiophene derivatives, acene derivatives, and porphyrinic derivatives having organic semiconductor properties. In detail, the compounds represented by Formulas 6 to 16 may be used to improve the organic semiconductor properties. The following examples are set forth to illustrate, but are not to be construed to limit the present invention.
[Formula 6]
For Formula 6, n andm are each independently 0 or a positive integer, and R and R1 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group,
an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group. Preferably, n and m are in the range of 0 to 10.
.Formula 7]
For Formula 7, n and n1 are each independently 0 or a positive integer, m is a positive integer, and R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group. Preferably, n and n' are each independently in the range of 0 to 10 and m is in the range of 1 to 100. [Formula 8]
For Formula 8, n andm are each independently 0 or a positive integer,
and Rl to R18 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialky1si 1y1 acetyl group, an ether group, an amino group, an imine group, an ester group, a nitrile group, a thioalkoxy group, a thioester group, a vinyl group, an aryl group, and a hetero group. Preferably, n and m are each independently in the range of 0 to 3.
[Formula 9]
For formula 9, n andm are each independently 0 or a positive integer, and R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group. Preferably, n and m are each independently in the range of 0 to 10.
[Formula 10]
For Formula 10, n and m are each independently 0 or a positive integer, and Rl to R18 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group. Preferably, n and m are each independently in the range of 0 to 3.
[Formula 11]
For Formula 11, n is 0 or a positive integer. Preferably, n is in the range of 0 to 10.
[Formula 12]
For Formula 12, n is O or a positive integer, and Rl to R8 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, anitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group. Preferably, n is in the range of 0 to 3. [Formula 13]
For Formula 13, n is 0 or a positive integer, m is a positive integer, and Rl to R8 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group,
a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group. Preferably, n is in the range of 0 to 3 and m is in the range of 1 to 100. [Formula 14]
For Formula 14, n and m are each independently 0 or a positive integer, and R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ester group, an ether group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group. Preferably, n and m are in the range of 0 to 10. [Formula 15]
For Formula 15, n and m are each independently 0 or a positive
integer, and Rl to R18 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group. Preferably, n and m are each independently in the range of 0 to 3. [Formula 16]
For Formula 16, R and R' are each independently any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to
20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group, a nitrile group, a nitro group, an ester group, an ether group, an imide group, an amide group, a thioester group, an aryl group, and a hetero aryl group, and A is a connection group and any one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an ether group having 1 to 20 carbon atoms, a thioether group, an aryl group,
a hetero aryl group, a vinyl group, and an acetyl group, n is a positive integer and preferably in the range of 1 to 10, 1 and m are each independently 0 or a positive integer and preferably in the range of 0 to 10, and k is a positive integer and preferably in the range of 1 to 100.
The compounds representd by Formulas 6 to 16 may form monomer compounds or polymer compounds.
Furthermore, in the above-mentioned compounds, the thiophene derivatives or the acene derivatives may be substituted by an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, a hetero group, etc.
In addition, the alkyl group, the alkoxy group, the ether group, the ester group, the thioalkoxy group, the vinyl group, the aryl group, and the hetero group that are used in the present invention may be each an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an ether group having 1 to 20 carbon atoms, an ester group having 1 to 20 carbon atoms, a thioalkoxy group having 1 to 20 carbon atoms, a thioester group having 1 to 20 carbon atoms, a vinyl group having 2 to
20 carbon atoms, an aryl group having 6 to 60 carbon atoms and preferably 6 to 16 carbon atoms, and a heterocyclic compound having 4 to 60 carbon atoms and preferably 4 to 12 carbon atoms.
The organic thin film transistor according to the present invention may be manufactured by using a material, a structure, and a process that are known in the related art, except the above-mentioned material and process. The OTFT according to the present invention includes an organic semiconductor layer, a gate electrode, a gate insulating film, a source electrode, and a drain electrode. In addition, the organic thin film transistor may further include a substrate on a lower surface of the gate electrode.
FIGS. 1 and 2 illustrate the structure of the organic thin film transistor according to the present invention. However, the organic thin film transistor of FIG.1 is provided herein for purpose of illustration only and is not intended to be limiting unless otherwise specified, and the organic thin film transistor of the present invention may have various types of structures without departing from the spirit of the present invention.
Examples of the substrate include, but are not limited to flexible
materials such as plastics and papers and inorganic material such as silicon and glass.
The gate electrode may be made of a conductive substance.
Illustrating, but non-limiting examples of the conductive substance include carbon, aluminium, vanadium, chrome, copper, zinc, silver, gold, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, tin, lead, similar metals, alloys of the metals, p- or n-doped silicon, zinc oxides, indium oxides, indium tin oxides (ITO), indium zinc oxides, and similar tin oxides, mixtures of oxides and metals such as tin oxide indium-based complex compounds, ZnO:Al and Sn(VSb, and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-l,2-dioxy)thiophene] , polypyrrole, and polyaniline.
The gate insulating film may be made of the insulating substance.
Illustrating, but non-limiting examples of the insulating substance include silicon oxides, silicon nitrides, and plastic insulators such as polyimide, poly(2-vinylpyridine), poly(4-vinylphenol), and polymethylmethacrylate.
Examples of the material used to manufacture the source, drain, and gate electrodes include, but are not limited to metal such as gold
(Au), platinum (Pt), silver (Ag), palladium (Pd), aluminium (Al), nickel (Ni), and chrome (Cr), conductive metal oxides such as indium tin oxides, indium zinc oxides, and nickel oxides, and conductive polymers such as polyaniline, polypyrrole, and polyethylenedioxythiophene. Furthermore, the present invention provides an electronic device that includes the organic thin film transistor. Examples of the electronic device include electronic papers, smart cards, memory devices, and display devices.
[Mode for Invention] Hereinafter, the present invention will be described in detail in light of Examples. The present invention may, however, be embodied in many different forms and should not be construed as being limited to the Examples set forth herein. Rather, these Examples are provided such that this disclosure will be thorough and complete and will fully convey the concept of the present invention to those skilled in the art.
PREPARATION EXAMPLE 1> Synthesis of the compound represented by Formula 4
After quinacridone (2.388 g, 7.65 mmol) and
4-dimethylamino-pyridine (0.476 g, 3.90 mmol, and 0.51 eq) were added to anhydrous THF (77 ml) in a nitrogen atmosphere, di-tert-butyldicarbonate
(4.174 g, 19.13 mmol, 2.5 eq) was added thereto at normal temperature for 1 hour three times so that the total amount was 4.174 g. After agitation was performed for one day, the solvent was vaporized at reduced pressure and the resulting mixture was washed in 5% sodium bicarbonate aqueous solution and distilled water. The impurity was subjected to column separation by using aCføC^ solvent to obtain yellow powder of the compound represented by Formula 4. GC/MS: [M+H]+ = 513
FIG.6 illustrates the thermogravimetric analysis (TGA) results of the compound of Formula 4, and it can be seen that the substituent suppressing the hydrogen bond is removed due to heat at 200°C or less.
EXPERIMENTAL EXAMPLE 1> Manufacturing of the organic thin film transistor by using vacuum deposition
The n-type dopped silicon wafer having low resistance was used as the gate electrode, and the gate insulating film that was made of SiU2 and had a thickness of 3000 A was layered thereon by using a heat oxidation process. Next, gold was applied to a thickness of 500 A by using a photol ithography process to form a source-drain electrode having a channel length of 10 μm and a channel width of 300 μm. The substrate was subjected to surface treatment by using a UV-ozone plasma, HMDS
(hexamethyldisilazane) was applied thereon by spin coating at 3000 rpm for 30 sec, and baking was performed at 120"C for 2 min. Subsequently, quinacridone represented by Formula 1 was deposited in a vacuum at a rate of 0.3 A/s to produce a channel substance in a thickness of 500 A. The organic thin film transistor which was manufactured by using the above-mentioned procedure had field effect mobility of 7.94 x 10~5 cmVVs. This is shown in FIG.3.
Even though quinacridone that was represented by Formula 1 had a relatively high band gap, the desirable field effect was ensured. Thus, it could be seen that the thin film having strong interaction between the molecules due to the hydrogen bond was formed.
EXPERIMENTAL EXAMPLE 2> Manufacturing of the organic thin film transistor by using the solution process
The n~type doped silicon wafer having low resistance was used as the gate electrode, and the gate insulating film that was made of Siθ2 and had a thickness of 3000 A was layered thereon by using a heat oxidation process. Next, gold was applied to a thickness of 500 A by using a photo1ithographyprocess to form a source-drain electrode having a channel length of 10 μm and a channel width of 300 μm. The substrate was subjected
to surface treatment by using a UV-ozone plasma, HMDS (hexamethyldisilazane) was applied thereon by spin coating at 3000 rpm for 30 sec, and baking was performed at 120°C for 2 min. The solution that was prepared by dissolving the compound represented by Formula 4 of Preparation Example 1 in tetrachloroethane to have a concentration of 2 w/w% was applied by spin coating at 1500 rpm for 20 sec and drying was performed at 50°C for 1 min and at 180°C for 2 min to manufacture the organic thin film transistor.
The organic thin film transistor which was manufactured by using the above-mentioned procedure had field effect mobility of 1.84 x 10~5 cmVVs. This is shown in FIG. 4.
Additionally, in order to confirm whether the substituent is removed and the substance capable of forming the hydrogen bond is regenerated by heat treatment, absorbance spectra of the thin film that was formed on a glass substrate by using the solution comprising the compound prepared in Preparation Example 1 (dotted line) and the thin film that was obtained by the heat treatment of Experimental Example 2 (full line) were measured, and the results are shown in FIG.5. From the results, it can be seen that the substituent is removed and the compound of Formula
1 is regenerated due to the heat treatment.
The field effect mobility of the organic thin film transistor that was manufactured by using the organic semiconductor layer formed through the solution process were relatively lower than that of the organic thin film transistor that was manufactured by using the semiconductor layer formed through the vacuum deposition, but a difference in properties was not significant. Therefore, it can be seen that the organic thin film transistor can be efficiently manufactured by regenerating the hydrogen bond.
Claims
[CLAIMS] [Claim 1]
An organic thin film transistor comprising: an organic semiconductor layer including an organic semiconductor substance having a functional group that can form a hydrogen bond.
[Claim 2]
The organic thin film transistor according to claim 1, wherein the organic semiconductor layer is formed by using the organic semiconductor substance having the functional group that can form the hydrogen bond.
[Claim 3]
The organic thin film transistor according to claim 2, wherein the organic semiconductor layer is formed by using a vacuum deposition process or solution coating process.
[Claim 4] The organic thin film transistor according to claim 1, wherein the organic semiconductor layer is formed by using a process that comprises forming a thin film by using an organic semiconductor substance in which a substituent group which is to be removed by using heat treatment or 1 ight treatment is added to the functional group of the organic semiconductor
substance that can form the hydrogen bond, and then performing the heat treatment or the light treatment.
[Claim 5]
The organic thin film transistor according to claim 4, wherein the thin film is formed by using a solution coating process. [Claim 6]
The organic thin film transistor according to claim 1, wherein the functional group that can form the hydrogen bond is selected from the group consisting of an alcohol group, a phenol group, a catechol group, a carbony1 group, a thiol group, and an amine group. [Claim 7]
The organic thin film transistor according to claim 1, wherein the organic semiconductor substance having the functional group that can form the hydrogen bond is any one selected from the group consisting of compounds represented by Formulas 1 to 3 and 6 to 16. [Formula 1]
[Formula 3]
[Formula 6]
for Formula 6, n andm are each independently 0 or a positive integer,
and R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group,
[Formula 7]
for Formula 7, n and n' are each independently 0 or a positive integer, m is a positive integer, and R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group,
[Formula 8]
for Formulaδ, n andm are each independently0 or a positive integer, and Rl to R18 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group,
[Formula 9]
[Formula 10]
[Formula 11]
[Formula 12]
[Formula 13]
[Formula 14]
for Formula 14, n and m are each independently 0 or a positive integer, and R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group,
[Formula 15]
[Formula 16]
for Formula 16, R and R' are each independently any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to
20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group, a nitrile group, a nitro group, an ether group, an ester group, an imide group, an amide group, a thioester group, an aryl group, and a hetero aryl group, A is a connection group and any one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an ether group having 1 to 20 carbon atoms, a thioether group, an aryl group, a hetero aryl group, a vinyl group, and an acetyl group, n is a positive
integer, 1 and m are each independently 0 or a positive integer, and k is a positive integer. [Claim 8]
A method of manufacturing an organic thin film transistor, which comprises forming a gate electrode, an insulating layer, a source electrode, a drain electrode, and an organic semiconductor layer, wherein an organic semiconductor layer is formed by using a compound having a functional group that can form a hydrogen bond. [Claim 9] The method of manufacturing an organic thin film transistor according to claim 8, wherein the organic semiconductor layer is formed by using a vacuum deposition process or a solution coating process. [Claim 10]
The method of manufacturing an organic thin film transistor according to claim 8, wherein the functional group that can form the hydrogen bond is selected from the group consisting of an alcohol group, a phenol group, a catechol group, a carbonyl group, a thiol group, and an amine group. [Claim 11]
The method of manufacturing an organic thin film transistor according to claim 8, wherein the compound having the functional group that can form the hydrogen bond is any one selected from the group consisting of compounds represented by Formulas 1 to 3 and 6 to 16.
[Formula 1]
[Formula 2]
[Formula 3]
[Formula 6]
for Formula 6, n andm are each independently 0 or a positive integer, and R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group,
[Formula 7]
[Formula 8]
[Formula 9]
[Formula 10]
[Formula 11]
[Formula 12]
[Formula 13]
[Formula 14]
for Formula 14, n and m are each independently 0 or a positive integer, and R and R1 are each independently any one selected from the
group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group,
[Formula 15]
for Formula 16, R and R' are each independently any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to
20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group, a nitrile group, a nitro group, an ether group, an ester group, an imide group, an amide group, a thioester group, an aryl group, and a hetero aryl group, A is a connection group and any one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an ether group having 1 to 20 carbon atoms, a thioether group, an aryl group, a hetero aryl group, a vinyl group, and an acetyl group, n is a positive integer, 1 and m are each independently 0 or a positive integer, and k is a positive integer.
[Claim 12]
A method of manufacturing an organic thin film transistor, which comprises forming a gate electrode, an insulating layer, a source electrode, a drain electrode, and an organic semiconductor layer, wherein
the organic semiconductor layer is formed byusing a process that comprises forming a thin film by using an organic semiconductor substance in which a substituent group which is to be removed by using heat treatment or light treatment is added to the functional group of an organic semiconductor substance that can form the hydrogen bond, and then performing the heat treatment or the light treatment. [Claim 13]
The method of manufacturing an organic thin film transistor according to claim 12, wherein the thin film for forming the organic semiconductor layer is formed by using a solution coating process. [Claim 14]
The method of manufacturing an organic thin film transistor according to claim 12, wherein the functional group that can form the hydrogen bond is selected from the group consisting of an alcohol group, a phenol group, a catechol group, a carbonyl group, a thiol group, and an amine group. [Claim 15]
The method of manufacturing an organic thin film transistor according to claim 12, wherein the organic semiconductor substance having
the functional group that can form the hydrogen bond is any one selected from the group consisting of compounds represented by Formulas 1 to 3 and
6 to 16.
[Formula 1]
[Formula 2]
[Formula 3]
[Formula 6]
for Formula 6, n andmare each independently 0 or a positive integer, and R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group,
[Formula 7]
for Formula 7, n and n' are each independently 0 or a positive integer, m is a positive integer, and R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group,
an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group,
[Formula 8]
[Formula 9]
[Formula 10]
[Formula 11]
for Formula 11, n is 0 or a positive integer, [Formula 12]
[Formula 13]
for Formula 13, n is 0 or a positive integer, m is a positive integer, and Rl to R8 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialky1si IyI acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group,
[Formula 14]
for Formula 14, n and m are each independently 0 or a positive integer, and R and R1 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy
group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group,
[Formula 15]
for Formula 16, R and R' are each independently any one selected
from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group, a nitrile group, a nitro group, an ether group, an ester group, an imide group, an amide group, a thioester group, an aryl group, and a hetero aryl group, A is a connection group and any one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an ether group having 1 to 20 carbon atoms, a thioether group, an aryl group, a hetero aryl group, a vinyl group, and an acetyl group, n is a positive integer, 1 and m are each independently 0 or a positive integer, and k is a positive integer. [Claim 16]
The method of manufacturing an organic thin film transistor according to any one of claims 12 to 15, wherein when the functional group that can form the hydrogen bond is the alcohol group, the substituent group that substitute for the alcohol group is selected from the group consisting of methyl ether, methoxymethyl ether, methoxythiomethyl ether, 2-methoxyethoxymethyl ether, bis(2-chloroethoxy)methyl ether, tetrahydropyranyl ether, 4-methoxytetrahydropyranyl ether, tetrahydrothiopyranyl ether, 4-methoxytetrahydropyranyl ether,
4-methoxythetrahydrothiopyranyl ether, tetrahydrofuranyl ether, tetrahydrothiofuranyl ether, 1-ethoxyethyl ether, 1-methyl-l-methoxyethyl ether, 2-(phenylselenyl)ethyl ether, t-butyl ether, allyl ether, benzyl ether, o-nitrobenzyl ether, triphenylmethyl ether, a-naphthyldiphenylmethyl ether, p-methoxyphenyldiphenylmethyl ether, 9-(9-phenyl-10-oxo)anthryl ether, trimethylsilyl ether, isopropyldimethylsilyl ether, t-butyldimethylsilyl ether, t-butyldiphenylsilyl ether, tribenzylsilyl ether, triisopropylsilyl ether, formate ester, acetate ester, trichloroacetate ester, phenoxyacetate ester, isobutyrate ester, pivaloate ester, adamantoate ester, benzoate ester, 2,4,6-trimethylbenzoate ester, methyl carbonate, 2,2,2-trichloroethyl carbonate, allyl carbonate, p-nitrophenyl carbonate, benzyl carbonate, s-benzyl thiocarbonate, N-phenyl carbonate, nitrate ester, and 2,4-dinitrophenylsulfenate ester. [Claim 17]
The method of manufacturing an organic thin film transistor according to any one of claims 12 to 15, wherein when the functional group that can form the hydrogen bond is the phenol group or the catechol group, the substituent group that substitute for the phenol group or the catechol
group is selected from the group consisting of methyl ether, methoxymethyl ether, 2-methoxyethoxymethyl ether, methoxythiomethyl ether, penacyl ether, allyl ether, cyclohexyl ether, t-butyl ether, benzyl ether, o-nitrobenzyl ether, 9-anthrylmethyl ether, 4-picolyl ether, t-butyldimethylsilyl ether, aryl acetate, aryl pivaloate, aryl benzoate, aryl 9-fluorenecarboxylate, aryl methyl carbonate, aryl 2,2,2-trichloroethyl carbonate, aryl vinyl carbonate, aryl benzyl carbonate, aryl methanesulfonate, methylenedioxy derivatives, acetonide derivatives, diphenylmethylenedioxy derivatives, cyclic borate, and cyclic carbonate. [Claim 18]
The method of manufacturing an organic thin film transistor according to any one of claims 12 to 15, wherein when the functional group that can form the hydrogen bond is the carbonyl group, the substituent group that substitute for the carbonyl group is selected from the group consist ing of dimethyl acetal andketal, bis(2,2,2-trichloroethyl) acetal and ketal, 1,3-dioxanes, 5-methylene-l,3-dioxanes, 5,5-dibromo-1,3-dioxanes, 1,3-dioxo1anes, 4-bromomethy1-1,3-dioxo1anes, 4-o-nitrophenyl-l,3-dioxolanes, S,S'-dimethyl acetal and ketal,
1,3-dithianes, 1,3-dithiolane, 1,3-oxathiolanes, o-trimethylsilyl cyanohydrins, N,N-dimethylhydrazones, 2,4-dinitrophenylhydrazones, o-phenylthiomethyl oximes, substituted methylene derivatives, bismethylenedioxy derivatives, methyl ester, methoxymethyl ester, methylthiomethyl ester, tetrahydropiranyl ester, benzyloxymethyl ester, penacyl ester, N-phthalimidomethyl ester, 2,2,2-trichloroethyl ester, 2-haloethyl ester, 2-(p-toluenesulfonyl)ethyl ester, t-butyl ester, cinnamyl ester, benzyl ester, triphenylmethyl ester, bis(o-nitrophenyl)methyl ester, 9-anthrylmethyl ester, 2-(9,10-dioxo)anthrylmethyl ester, piperonyl ester, trimethylsilyl ester, t-butyldimethylsilyl ester, s-t-butyl ester, 2-aIky1-1,3-oxazolines, N,N-dimethylamide, N-7-nitroindoylamide, hydrazide, N-phenylhydrazide, and N,N'-diisopropylhydrizide. [Claim 19] The method of manufacturing an organic thin film transistor according to any one of claims 12 to 15, wherein when the functional group that can form the hydrogen bond is the thiol group, the substituent group that substitute for the thiol group is selected from the group consisting of s-benzyl thioether, s-p-methoxybenzyl thioether, s-p-nitrobenzyl
thioether, s-4-picolyl thioether, s-2-picolyl N-oxide thioether, s-9-anthrylmethyl thioether, s-diphenylmethyl thioether, s-di(p-methoxyphenyl)methyl dithioether, s-triphenylmethyl thioether, s-2,4-dinitrophenyl thioether, s-t-butyl thioether, s-isobutoxymethyl monothioacetal , s-2-tetrahydropiranyl monothioacetal , s-acetamidomethyl aminothioacetal , s-cyanomethyl thioether, s-2-nitro-l-phenylethyl thioether, s-2,2-bis(carboethoxy)ethyl thioether, s-benzoyl derivatives, s-(N-ethylcarbamate), and s-ethyl disulfide. [Claim 20] The method of manufacturing an organic thin film transistor according to any one of claims 12 to 15, wherein when the functional group that can form the hydrogen bond is the amine group, the substituent group that substitute for the amine group is selected from the group consisting of methyl carbamate, 9-fluorenylmethyl carbamate, 2,2,2-trichloroethyl carbamate, 2-trimethylsiIyIethyl carbamate, 1,1-dimethylpropynyl carbamate, 1-methyl-l-phenylethyl catbamate, l-methyl-l-(4-biphenylyl)ethyl carbamate, l,l-dimethyl-2-haloethyl carbamate, l,l-dimethyl-2-cyanoethyl carbamate, t-butyl carbamate, cyclobutyl carbamate, 1-methylcyclobutyl carbamate, 1-adamantyl
carbamate, vinyl carbamate, alIyI carbamate, cinnamyl carbamate, 8-quinolyl carbamate, N-hydroxypiperidinyl carbamate, 4,5-diphenyl-3-oxazoline-2-one, benzyl carbamate, p-nitrobenzyl carbamate, 3,4-dimethoxy-6-nitrobenzyl carbamate, 2,4-dichlorobenzyl carbamate, 5-benzisoxazolylmethyl carbamate, 9-anthrylmethyl carbamate, diphenylmethyl carbamate, isonicotinyl carbamate, s-benzyl carbamate, N-(N'-phenylaminothiocarbonyl) derivatives, N-formyl , N-acetyl , N-chloroacetyl, N-trichloroacetyl , N-trifluoroacetyl , N-o-nitrophenylacetyl , N-o-nitrophenoxyacetyl , N-acetoacetyl , N-3-phenylpropionyl, N-3-(p-hydroxyphenyl)propionyl ,
N-2-methyl-2-(o-nitrophenoxy)propionyl,
N-2-methyl-2-(o-phenylazophenoxy)propionyl , N-4-chlorobutyryl , N-o-nitrocinnamoyl , N-picolinoyl , N-(N'-acetylmethionyl , N-benzoyl , N-phthaloyl, N-dithiasuccinoyl , N-allyl, N-phenacyl , N-3-acetoxypropyl , quaternary ammonium salt, N-methoxymethyl , N-benzyloxymethyl , N-pivaloyloxymethyl , N-tetrahydropyranyl , N-2,4-dinitrophenyl , N-benzyl , N-o-nitrobenzyl , N-di (p-methoxyphenyl )methyl , N-triphenylmethyl , N-(p-methoxypheny1 ) dipheny1methy1 , N-dipheny1-4-pyridy1methy1 , N-2-picolyl N'-oxide, N,N'-isopropylidene, N-benzyl idene,
N-p-nitrobenzyl idene, N-sal icyl idene,
N-Cδ.δ-dimethyl-S-oxo-l-cyclohexenyl , N-nitro, N-oxide, N-diphenylphosphinyl , N-dimethylthiophosphinyl , N-benzenesulfenyl , N-o-nitrobenzenesulfenyl , N-2,4,6-trimethylbenzenesulfonyl , N-toluenesulfonyl , N-benzylsulfonyl , N-trifluoromethylsulfonyl , and N-phenacyl sulfonyl. [Claim 21]
The method of manufacturing an organic thin film transistor according to any one of claims 12 to 15, wherein the heat treatment is performed at 20 to 350°C. [Claim 22]
The method of manufacturing an organic thin film transistor according to any one of claims 12 to 15, wherein the light treatment is performed by using light of 180 to 700 run. [Claim 23]
The method of manufacturing an organic thin film transistor according to claim 12, wherein when the thin film is formed by using the organic semiconductor substance in which a substituent group which is to be removed by using heat treatment or light treatment is added to the
functional group of the organic semiconductor substance that can form the hydrogen bond, a photo acid generator is added. [Claim 24]
The method of manufacturing an organic thin film transistor according to claim 12, wherein when the thin film is formed by using the organic semiconductor substance in which a substituent group which is to be removed by using heat treatment or light treatment is added to the functional group of the organic semiconductor substance that can form the hydrogen bond, a photo acid generator is added and heat and light are simultaneously or sequentially treated. [Claim 25]
The method of manufacturing an organic thin film transistor according to claim 23, wherein the photo acid generator is any one selected from the group consisting of diaryliodonium salts, triarylsulfonium salts, imido sulfonates, 4-nitrobenzenesulfonic acid derivatives, disulphone compounds, sulfonyl substituted diazomethanes, and dibenzyl sulfones aryl-bis-trichloromethyl-s-triazine. [Claim 26]
An electronic paper comprising the organic thin film transistor
according to any one of claims 1 to 7. [Claim 27]
A smart card comprising the organic thin film transistor according to any one of claims 1 to 7. [Claim 28]
A display device comprising the organic thin film transistor according to any one of claims 1 to 7. [Claim 29]
A memory device comprising the organic thin film transistor according to any one of claims 1 to 7. [Claim 30]
The method of manufacturing an organic thin film transistor according to claim 23 or 24, wherein patterning of a device is selectively performed at only a portion which is patterned by using the light treatment.
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| KR1020060070933A KR100918362B1 (en) | 2006-07-27 | 2006-07-27 | Organic tfts and method for fabricating the same |
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Cited By (4)
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|---|---|---|---|---|
| WO2011150137A3 (en) * | 2010-05-28 | 2012-01-12 | Corning Incorporated | Enhanced transistors employing photoactive organic materials and methods of manufacturing same |
| WO2012041849A1 (en) | 2010-09-29 | 2012-04-05 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
| CN103430293A (en) * | 2011-03-30 | 2013-12-04 | 索尼公司 | Method for producing organic transistor, organic transistor, method for producing semiconductor device, semiconductor device, and electronic apparatus |
| US8946376B2 (en) | 2010-09-29 | 2015-02-03 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101100647B1 (en) * | 2009-06-24 | 2012-01-03 | 포항공과대학교 산학협력단 | Method for preparing a polymer gate dielectric |
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| US6555840B1 (en) * | 1999-02-16 | 2003-04-29 | Sharp Kabushiki Kaisha | Charge-transport structures |
| US6753245B2 (en) * | 2000-06-29 | 2004-06-22 | Board Of Trustees, The University Of Illinois | Organometallic compounds and their use as precursors for forming films and powders of metal or metal derivatives |
| US7005672B2 (en) * | 2002-10-17 | 2006-02-28 | Xerox Corporation | Thin film transistor with a semiconductor layer that includes a gelable self-organizable polymer |
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| JP2005085945A (en) | 2003-09-08 | 2005-03-31 | Canon Inc | Field effect type organic transistor and its manufacturing method |
| US7746418B2 (en) * | 2003-10-30 | 2010-06-29 | Panasonic Corporation | Conductive thin film and thin film transistor |
| KR101304697B1 (en) * | 2006-06-07 | 2013-09-06 | 삼성전자주식회사 | Organic semiconductor materials using stacking-inducing compounds, composition comprising the materials, organic semiconductor thin film using the composition and organic electronic device employing the thin film |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6555840B1 (en) * | 1999-02-16 | 2003-04-29 | Sharp Kabushiki Kaisha | Charge-transport structures |
| US6753245B2 (en) * | 2000-06-29 | 2004-06-22 | Board Of Trustees, The University Of Illinois | Organometallic compounds and their use as precursors for forming films and powders of metal or metal derivatives |
| US7005672B2 (en) * | 2002-10-17 | 2006-02-28 | Xerox Corporation | Thin film transistor with a semiconductor layer that includes a gelable self-organizable polymer |
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| WO2011150137A3 (en) * | 2010-05-28 | 2012-01-12 | Corning Incorporated | Enhanced transistors employing photoactive organic materials and methods of manufacturing same |
| JP2013531884A (en) * | 2010-05-28 | 2013-08-08 | コーニング インコーポレイテッド | Reinforced semiconductor device using photoactive organic material and method for manufacturing the same |
| US8877546B2 (en) | 2010-05-28 | 2014-11-04 | Corning Incorporated | Enhanced semiconductor devices employing photoactive organic materials and methods of manufacturing same |
| WO2012041849A1 (en) | 2010-09-29 | 2012-04-05 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
| JP2014501695A (en) * | 2010-09-29 | 2014-01-23 | ビーエーエスエフ ソシエタス・ヨーロピア | Diketopyrrolopyrrole semiconductor |
| US8946376B2 (en) | 2010-09-29 | 2015-02-03 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
| CN103430293A (en) * | 2011-03-30 | 2013-12-04 | 索尼公司 | Method for producing organic transistor, organic transistor, method for producing semiconductor device, semiconductor device, and electronic apparatus |
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| KR100918362B1 (en) | 2009-09-22 |
| KR20080010644A (en) | 2008-01-31 |
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