KR100918362B1 - Organic tfts and method for fabricating the same - Google Patents
Organic tfts and method for fabricating the same Download PDFInfo
- Publication number
- KR100918362B1 KR100918362B1 KR1020060070933A KR20060070933A KR100918362B1 KR 100918362 B1 KR100918362 B1 KR 100918362B1 KR 1020060070933 A KR1020060070933 A KR 1020060070933A KR 20060070933 A KR20060070933 A KR 20060070933A KR 100918362 B1 KR100918362 B1 KR 100918362B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- ether
- formula
- ester
- independently
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 239000010409 thin film Substances 0.000 claims abstract description 88
- 239000004065 semiconductor Substances 0.000 claims abstract description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 83
- 239000001257 hydrogen Substances 0.000 claims abstract description 83
- 125000000524 functional group Chemical group 0.000 claims abstract description 74
- 239000000463 material Substances 0.000 claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 claims abstract description 28
- -1 bis (2-chloroethoxy) methyl Chemical group 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 125000003277 amino group Chemical group 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000001033 ether group Chemical group 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 47
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 46
- 150000007970 thio esters Chemical group 0.000 claims description 46
- 125000004185 ester group Chemical group 0.000 claims description 45
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 45
- 125000000879 imine group Chemical group 0.000 claims description 42
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 41
- 125000005842 heteroatom Chemical group 0.000 claims description 37
- 125000002560 nitrile group Chemical group 0.000 claims description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000002825 nitriles Chemical class 0.000 claims description 11
- 125000003158 alcohol group Chemical group 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 150000003568 thioethers Chemical class 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- 238000001771 vacuum deposition Methods 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 6
- 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 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 5
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 5
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 claims description 5
- 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 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
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 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
- HXNHJWLEAMYJJI-UHFFFAOYSA-N ethyl ethylsulfanylformate Chemical compound CCOC(=O)SCC HXNHJWLEAMYJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005462 imide group Chemical group 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
- 125000000101 thioether group Chemical group 0.000 claims description 4
- FTVXFBJENACRRL-UHFFFAOYSA-N (1-hydroxypiperidin-2-yl) carbamate Chemical compound NC(=O)OC1CCCCN1O FTVXFBJENACRRL-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- UXWLHPWCZJEEDL-UHFFFAOYSA-N 4-(2-nitrophenyl)-1,3-dioxolane Chemical compound [O-][N+](=O)C1=CC=CC=C1C1OCOC1 UXWLHPWCZJEEDL-UHFFFAOYSA-N 0.000 claims description 3
- BLAURXPHWHQJKX-UHFFFAOYSA-N 4-(bromomethyl)-1,3-dioxolane Chemical class BrCC1COCO1 BLAURXPHWHQJKX-UHFFFAOYSA-N 0.000 claims description 3
- JLECSPKJBGOVBW-UHFFFAOYSA-N 5-methylidene-1,3-dioxane Chemical class C=C1COCOC1 JLECSPKJBGOVBW-UHFFFAOYSA-N 0.000 claims description 3
- 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 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
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 3
- 150000004250 monothioacetals Chemical class 0.000 claims description 3
- KWBIXTIBYFUAGV-UHFFFAOYSA-M n-ethylcarbamate Chemical compound CCNC([O-])=O KWBIXTIBYFUAGV-UHFFFAOYSA-M 0.000 claims description 3
- 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 3
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 claims description 3
- 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
- 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
- 125000006091 1,3-dioxolane group 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
- 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
- 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
- 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
- UCZSGRLQZLKLCQ-UHFFFAOYSA-N 2-phenylpropan-2-yl carbamate Chemical compound NC(=O)OC(C)(C)C1=CC=CC=C1 UCZSGRLQZLKLCQ-UHFFFAOYSA-N 0.000 claims description 2
- JTSSUEWTRDWHGY-UHFFFAOYSA-N 4-(pyridin-4-ylmethoxymethyl)pyridine Chemical compound C=1C=NC=CC=1COCC1=CC=NC=C1 JTSSUEWTRDWHGY-UHFFFAOYSA-N 0.000 claims description 2
- NTCIAFWCCFAZLW-UHFFFAOYSA-N 5,5-dibromo-1,3-dioxane Chemical class BrC1(Br)COCOC1 NTCIAFWCCFAZLW-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
- 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
- 125000003047 N-acetyl group Chemical group 0.000 claims description 2
- 150000001204 N-oxides Chemical class 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
- 150000001241 acetals Chemical class 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 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
- 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
- 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
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004675 formic acid derivatives Chemical class 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
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 2
- OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical compound NC(=O)OCC=C OCAAZRFBJBEVPS-UHFFFAOYSA-N 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 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
- 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 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 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NHZLLKNRTDIFAD-UHFFFAOYSA-N 2,5-dihydro-1,3-oxazole Chemical compound C1OCN=C1 NHZLLKNRTDIFAD-UHFFFAOYSA-N 0.000 claims 1
- QWYTUBPAXJYCTH-UHFFFAOYSA-N 2-trimethylsilylethyl carbamate Chemical compound C[Si](C)(C)CCOC(N)=O QWYTUBPAXJYCTH-UHFFFAOYSA-N 0.000 claims 1
- GDXXYJRQFQZYNL-UHFFFAOYSA-N 9h-fluoren-1-ylmethyl carbamate Chemical compound C1C2=CC=CC=C2C2=C1C(COC(=O)N)=CC=C2 GDXXYJRQFQZYNL-UHFFFAOYSA-N 0.000 claims 1
- GWNPLMHMFJEYCI-UHFFFAOYSA-N C(N)(OC(C#C)(C)C)=O.C(N)(OC(C#C)(C)C)=O Chemical compound C(N)(OC(C#C)(C)C)=O.C(N)(OC(C#C)(C)C)=O GWNPLMHMFJEYCI-UHFFFAOYSA-N 0.000 claims 1
- OHVUGENQIOPKLB-UHFFFAOYSA-N C(N)(OC(C1=CC=CC=C1)C1=CC=CC=C1)=O.C(N)(OC(C1=CC=CC=C1)C1=CC=CC=C1)=O Chemical compound C(N)(OC(C1=CC=CC=C1)C1=CC=CC=C1)=O.C(N)(OC(C1=CC=CC=C1)C1=CC=CC=C1)=O OHVUGENQIOPKLB-UHFFFAOYSA-N 0.000 claims 1
- TTZMAVUZTGCPIL-UHFFFAOYSA-N C(N)(OC(CC#N)(C)C)=O.C(N)(OC(CC#N)(C)C)=O Chemical compound C(N)(OC(CC#N)(C)C)=O.C(N)(OC(CC#N)(C)C)=O TTZMAVUZTGCPIL-UHFFFAOYSA-N 0.000 claims 1
- WZQAXNDIEIIJTJ-UHFFFAOYSA-N C(N)(OC1=NC2=CC=CC=C2C=C1)=O.C(N)(OC=1C=CC=C2C=CC=NC12)=O Chemical compound C(N)(OC1=NC2=CC=CC=C2C=C1)=O.C(N)(OC=1C=CC=C2C=CC=NC12)=O WZQAXNDIEIIJTJ-UHFFFAOYSA-N 0.000 claims 1
- GWGOERUQRKOZKN-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NC(OC1C1=CC=CC=C1)=O.C1(=CC=CC=C1)C1=NC(OC1C1=CC=CC=C1)=O Chemical compound C1(=CC=CC=C1)C1=NC(OC1C1=CC=CC=C1)=O.C1(=CC=CC=C1)C1=NC(OC1C1=CC=CC=C1)=O GWGOERUQRKOZKN-UHFFFAOYSA-N 0.000 claims 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 239000012955 diaryliodonium Substances 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 1
- GRKWHXNAHIMNJD-UHFFFAOYSA-N methoxysulfanyloxymethane Chemical compound COSOC GRKWHXNAHIMNJD-UHFFFAOYSA-N 0.000 claims 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims 1
- XQYMIMUDVJCMLU-UHFFFAOYSA-N phenoxyperoxybenzene Chemical compound C=1C=CC=CC=1OOOC1=CC=CC=C1 XQYMIMUDVJCMLU-UHFFFAOYSA-N 0.000 claims 1
- 125000005547 pivalate group Chemical group 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- RWUGBYOALBYTGU-UHFFFAOYSA-N pyridin-4-ylmethyl carbamate Chemical compound NC(=O)OCC1=CC=NC=C1 RWUGBYOALBYTGU-UHFFFAOYSA-N 0.000 claims 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical class OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 14
- 238000012856 packing Methods 0.000 abstract description 7
- 230000009878 intermolecular interaction Effects 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 17
- 239000010408 film Substances 0.000 description 8
- 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
- 230000001965 increasing effect Effects 0.000 description 7
- 230000005669 field effect Effects 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 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 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 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 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 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
- 239000011651 chromium Substances 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000012212 insulator Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 238000000206 photolithography Methods 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
- 239000002904 solvent Substances 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- AFCTUKSQTSHXEZ-UHFFFAOYSA-N (1-cyano-2-methylpropan-2-yl) carbamate Chemical compound N#CCC(C)(C)OC(N)=O AFCTUKSQTSHXEZ-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-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
- 229910004298 SiO 2 Inorganic materials 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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 229940066528 trichloroacetate Drugs 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- BSRPNTQISRBMQP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethylperoxymethoxy)ethane Chemical compound COCCOCOOCCOC BSRPNTQISRBMQP-UHFFFAOYSA-N 0.000 description 1
- DQNSKXYRRRCKGH-UHFFFAOYSA-N 1-methoxy-4-methylsulfanylbenzene Chemical compound COC1=CC=C(SC)C=C1 DQNSKXYRRRCKGH-UHFFFAOYSA-N 0.000 description 1
- SDJNOBUNFYNROE-UHFFFAOYSA-N 2-methylbut-3-yn-2-yl carbamate Chemical compound C#CC(C)(C)OC(N)=O SDJNOBUNFYNROE-UHFFFAOYSA-N 0.000 description 1
- ZRVBMNHMJLBKSY-UHFFFAOYSA-N 2-phenacyloxy-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)COCC(=O)C1=CC=CC=C1 ZRVBMNHMJLBKSY-UHFFFAOYSA-N 0.000 description 1
- 150000000499 3-oxazolines Chemical class 0.000 description 1
- 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 description 1
- 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 description 1
- BPKOOYZZEUQWIB-UHFFFAOYSA-N CC1=CSC=C1.CC1=CSC=C1 Chemical compound CC1=CSC=C1.CC1=CSC=C1 BPKOOYZZEUQWIB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- RLNUQRYBHCRIQG-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(CNC(O)=O)C=C1.C(N)(OCC1=CC=C(C=C1)[N+](=O)[O-])=O Chemical compound [N+](=O)([O-])C1=CC=C(CNC(O)=O)C=C1.C(N)(OCC1=CC=C(C=C1)[N+](=O)[O-])=O RLNUQRYBHCRIQG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- DUXANUSOCMOJSI-UHFFFAOYSA-N benzhydryl carbamate Chemical compound C=1C=CC=CC=1C(OC(=O)N)C1=CC=CC=C1 DUXANUSOCMOJSI-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005685 electric field effect Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 238000000813 microcontact printing Methods 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000885 poly(2-vinylpyridine) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- FLCPORVHXQFBHT-UHFFFAOYSA-N quinolin-8-yl carbamate Chemical compound C1=CN=C2C(OC(=O)N)=CC=CC2=C1 FLCPORVHXQFBHT-UHFFFAOYSA-N 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
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
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Thin Film Transistor (AREA)
Abstract
본 발명은 수소결합을 할 수 있는 작용기를 포함하는 유기 반도체 물질로 이루어진 유기 반도체층을 포함하는 유기 박막 트랜지스터 및 이의 제조방법에 관한 것이다. 본 발명의 유기 박막 트랜지스터는 유기 반도체 물질로서 수소결합을 할 수 있는 작용기를 가진 반도체 물질을 사용함으로써 분자간 상호작용을 최대화하여 분자간 패킹 특성을 향상시킬 수 있다. 또한, 용액 공정에 의해 유기 반도체층을 형성할 수 있어, 공정단가를 낮출 수 있다. The present invention relates to an organic thin film transistor including an organic semiconductor layer made of an organic semiconductor material including a functional group capable of hydrogen bonding, and a method of manufacturing the same. The organic thin film transistor of the present invention can improve intermolecular packing characteristics by maximizing intermolecular interaction by using a semiconductor material having a functional group capable of hydrogen bonding as an organic semiconductor material. Moreover, an organic-semiconductor layer can be formed by a solution process, and process cost can be reduced.
수소결합, 유기 반도체, 유기 박막 트랜지스터 Hydrogen Bond, Organic Semiconductor, Organic Thin Film Transistor
Description
도 1은 유기 박막 트랜지스터의 하부 콘택트(bottom contact) 구조를 예시한 단면도이다(101: 기판 겸 게이트, 102: 소스(source) 전극, 103: 드레인(drain) 전극, 104: 절연층(gate insulator), 105: 유기 반도체층(organic semiconductor layer)).1 is a cross-sectional view illustrating a bottom contact structure of an organic thin film transistor (101: substrate and gate, 102: source electrode, 103: drain electrode, 104: gate insulator) 105: organic semiconductor layer).
도 2는 유기 박막 트랜지스터의 상부 콘택트(top contact) 구조를 예시한 단면도이다(101: 기판 겸 게이트, 102: 소스(source) 전극, 103: 드레인(drain) 전극, 104: 절연층(gate insulator), 105: 유기 반도체층(organic semiconductor layer)).2 is a cross-sectional view illustrating a top contact structure of an organic thin film transistor (101: substrate and gate, 102: source electrode, 103: drain electrode, 104: gate insulator) 105: organic semiconductor layer).
도 3은 도 1의 유기 박막 트랜지스터 구조에 있어서, 화학식 1의 화합물을 진공 증착하여 유기 반도체층을 형성한 경우의 출력 곡선(output curve)이다.FIG. 3 is an output curve when the organic semiconductor layer is formed by vacuum deposition of the compound of
도 4는 도 1의 유기 박막 트랜지스터 구조에 있어서, 화학식 4의 화합물을 스핀 코팅하여 유기 반도체층을 형성한 경우의 출력 곡선(output curve)이다.FIG. 4 is an output curve when the organic semiconductor layer is formed by spin coating the compound of Chemical Formula 4 in the organic thin film transistor structure of FIG. 1.
도 5는 용액 공정으로 얻어진 화학식 4의 화합물의 열처리 전과 열처리 후의 박막에 대한 UV-VIS스펙트럼이다.5 is a UV-VIS spectrum of the thin film before and after the heat treatment of the compound of the formula (4) obtained by the solution process.
도 6은 화학식 4의 화합물의 열분석(TGA, thermogravimetric analysis) 그래 프이다.FIG. 6 is a thermogravimetric analysis (TGA) graph of the compound of Formula 4. FIG.
본 발명은 유기 박막 트랜지스터 및 이의 제조방법에 관한 것이다.The present invention relates to an organic thin film transistor and a method of manufacturing the same.
박막형태의 전계효과 트랜지스터(field-effect transistor; FET)는 마이크로 전자공학에서 기본적인 구조체이다. FET는 소스 전극, 드레인 전극 및 게이트 전극인 세 개의 전극, 절연층 및 반도체층을 갖는다. 이러한 FET에서, 반도체층이 두 개의 전극인 소스 전극과 드레인 전극 사이의 도전성 채널일 때, 커패시터(capacitor)로 작용한다. 상기 채널에서, 전하 캐리어(charge carrier)의 농도는 게이트 전극을 통하여 인가되는 전압에 의하여 조정되며, 그 결과 소스 전극과 드레인 전극 사이의 전기 전하의 흐름은 상기 게이트 전극을 통하여 인가되는 전압에 의하여 조절될 수 있다.Thin-film field-effect transistors (FETs) are fundamental structures in microelectronics. The FET has three electrodes, a source electrode, a drain electrode, and a gate electrode, an insulating layer, and a semiconductor layer. In this FET, when the semiconductor layer is a conductive channel between two electrodes, the source electrode and the drain electrode, it acts as a capacitor. In the channel, the concentration of charge carriers is adjusted by the voltage applied through the gate electrode, so that the flow of electrical charge between the source and drain electrodes is controlled by the voltage applied through the gate electrode. Can be.
최근, 유기 반도체성 물질을 사용하는 FET의 발전에 대하여 관심이 높아지고 있다. 유기 반도체성 물질을 FET에 사용하는 경우, 스크린 프린팅(screen-printing), 잉크젯 프린팅(ink-jet printing) 및 마이크로접촉 프린팅(micro-contact printing)과 같은 프린팅 방법에 의하여 전자 소자를 제조할 수 있다. 또한, 이러한 유기 반도체성 물질은 통상적인 무기 반도체성 물질과 달리 훨씬 낮은 기판온도 및 진공이 필요 없거나 거의 없는 상태에서 공정이 진행될 수 있다. 따라서, FET를 포함하여 유기 반도체성 물질을 사용하는 전자 소자는, 무기 반도체성 물질을 사용하는 경우와 비교하여, 그 제조가 매우 유연하고 비용이 적게 들 수 있다.In recent years, there has been increasing interest in the development of FETs using organic semiconducting materials. When organic semiconducting materials are used in FETs, electronic devices can be manufactured by printing methods such as screen-printing, ink-jet printing, and micro-contact printing. . In addition, the organic semiconducting material can be processed in a state where a much lower substrate temperature and vacuum are required or little, unlike conventional inorganic semiconducting materials. Therefore, the electronic device using the organic semiconducting material, including the FET, can be very flexible and inexpensive to manufacture compared with the case of using the inorganic semiconducting material.
1980년대 이후에는, 작은 분자, 고분자 및 올리고머와 같은 여러 가지 형태의 유기 물질들이 FET에서의 유기 반도체성 물질로서 테스트되었다. 이러한 분야에서의 연구결과, FET에서 전하 캐리어의 이동성(charge carrier mobility) 관점에서 볼 때 유기 FET의 성능(performance)은 10-5 ㎠/Vs 에서 1 ㎠/Vs까지 상승되었다(J. M. Shaw, P. F. Seidler, IBM J. Res. & Dev., Vol. 45, 3 (2001)). 유기 트랜지스터의 성능은 현재 무정형 실리콘 트랜지스터(amorphous silicon transistor)의 성능을 능가할 정도이며, 그 결과 이러한 유기 트랜지스터는 전자종이(E-paper), 스마트 카드(smart card), 메모리 소자 및 디스플레이 장치에까지 적용될 수 있다.Since the 1980s, various types of organic materials such as small molecules, polymers and oligomers have been tested as organic semiconducting materials in FETs. Research in this field has shown that the performance of organic FETs has increased from 10 -5 cm 2 / Vs to 1 cm 2 / Vs in terms of charge carrier mobility in FETs (JM Shaw, PF Seidler). , IBM J. Res. & Dev., Vol. 45, 3 (2001)). The performance of organic transistors far exceeds that of current amorphous silicon transistors, and as a result, these organic transistors can be applied to e-paper, smart cards, memory devices and display devices. Can be.
전계효과 트랜지스터의 기본적인 기능은 게이트에 인가된 전압에 의해서 소스와 드레인 사이에 흐르는 전류의 양을 제어하는 것이다. 이러한 작용을 하기 위해서 게이트 전압에 따라 반도체층의 저항이 큰 폭으로 변화하여야 한다. 이런 조건을 만족하기 위하여 유기 반도체층은 결정성을 가지는 것이 유리하다고 알려져 있다. 지금까지의 유기 반도체층에 쓰이는 반도체 물질은 유기 반도체 물질 간의 반데르발스의 힘(van der Waals' force)에 의한 결합력을 이용하여 결정성을 보이는 경우가 대부분이었다. 그러나, 반데르발스의 힘은 그 결합력이 매우 약하여 결정성 또는 좋은 유기막 형성에 걸림돌로 작용하고 있다,The basic function of a field effect transistor is to control the amount of current flowing between the source and drain by the voltage applied to the gate. In order to do this, the resistance of the semiconductor layer must be changed greatly according to the gate voltage. In order to satisfy such conditions, it is known that the organic semiconductor layer has an advantageous crystallinity. Up to now, the semiconductor materials used in the organic semiconductor layers have been mostly crystallized using the bonding force of van der Waals' force between the organic semiconductor materials. However, van der Waals' strength is so weak that it is a barrier to crystalline or good organic film formation.
또한, 이런 유기 반도체 물질을 전자소자에 사용하는 경우, 유기물이 작동 중에 전하를 띠어야 하는데, 전하를 띤 상태에서 수분과 공기에 취약하기 때문에 상업적으로 사용하기 위한 안정된 소자를 구현하기 힘들다는 문제가 있다.In addition, when the organic semiconductor material is used in an electronic device, the organic material must be charged during operation, and it is difficult to implement a stable device for commercial use because it is vulnerable to moisture and air in the charged state. have.
본 발명자들은 유기 박막 트랜지스터의 유기 반도체층을 수소결합을 할 수 있는 작용기를 갖는 유기 반도체 물질로 형성하는 경우 분자간 상호작용을 최대화하여 분자간 패킹 특성을 향상시킬 수 있다는 사실을 밝혀 내었다. 이에 본 발명은 수소결합을 할 수 있는 작용기를 갖는 유기 반도체 물질을 이용한 유기 박막 트랜지스터 및 이의 제조방법을 제공하는 것을 목적으로 한다.The inventors have found that when the organic semiconductor layer of the organic thin film transistor is formed of an organic semiconductor material having a functional group capable of hydrogen bonding, the intermolecular interaction can be maximized to improve the intermolecular packing property. Accordingly, an object of the present invention is to provide an organic thin film transistor using an organic semiconductor material having a functional group capable of hydrogen bonding and a method of manufacturing the same.
본 발명은 수소결합을 할 수 있는 작용기를 갖는 유기 반도체 물질로 이루어진 유기 반도체층을 포함하는 유기 박막 트랜지스터를 제공한다.The present invention provides an organic thin film transistor including an organic semiconductor layer made of an organic semiconductor material having a functional group capable of hydrogen bonding.
또한, 본 발명은 게이트 전극, 절연층, 소스 전극, 드레인 전극 및 유기 반도체층을 각각 형성하는 단계를 포함하는 유기 박막 트랜지스터의 제조방법에 있어서, 상기 유기 반도체층을 수소결합을 할 수 있는 작용기를 갖는 화합물을 이용하여 형성하는 것을 특징으로 하는 유기 박막 트랜지스터의 제조방법을 제공한다.In addition, the present invention is a method of manufacturing an organic thin film transistor comprising the step of forming a gate electrode, an insulating layer, a source electrode, a drain electrode and an organic semiconductor layer, each functional group capable of hydrogen bonding the organic semiconductor layer It provides using the compound which has, The manufacturing method of the organic thin film transistor characterized by the above-mentioned.
또한, 본 발명은 게이트 전극, 절연층, 소스 전극, 드레인 전극 및 유기 반도체층을 각각 형성하는 단계를 포함하는 유기 박막 트랜지스터의 제조방법에 있어서, 상기 유기 반도체층을 수소결합을 할 수 있는 작용기를 포함하는 유기 반도체 물질에서 수소결합을 이루는 작용기에 열처리 또는 광처리에 의해 제거되는 치환기가 도입된 유기 반도체 물질을 이용하여 박막을 형성한 후 열처리 또는 광처리 하 는 단계를 포함하는 방법에 의하여 형성하는 것을 특징으로 하는 유기 박막 트랜지스터의 제조방법을 제공한다.In addition, the present invention is a method of manufacturing an organic thin film transistor comprising the step of forming a gate electrode, an insulating layer, a source electrode, a drain electrode and an organic semiconductor layer, each functional group capable of hydrogen bonding the organic semiconductor layer Forming a thin film using an organic semiconductor material in which a substituent is removed by heat treatment or light treatment to the functional group forming a hydrogen bond in the organic semiconductor material comprising the step of forming a thin film by heat treatment or light treatment A manufacturing method of an organic thin film transistor is provided.
또한, 본 발명은 상기 유기 박막 트랜지스터를 포함하는 전자장치를 제공한다.In addition, the present invention provides an electronic device including the organic thin film transistor.
이하, 본 발명에 대해 구체적으로 설명한다.EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated concretely.
일반적으로 유기 박막 트랜지스터를 제작하는데 사용되는 유기 반도체 물질은 반데르발스 에너지에 의한 상호작용만으로 패킹을 이루기 때문에 분자간 인력이 충분히 강하지 않으며, 이로 인해 분자간 결합력이 약하고 분자간 거리가 충분히 가까워지지 못하므로 트랜지스터 상에서 분자간 캐리어의 이동이 충분히 높지 못한 단점을 가지고 있다. 또한, 분자간 패킹이 충분하지 못하여 외부로부터 공기나 수분이 반도체층 내로 유입되기가 쉬우므로 이로 인해 소자의 안정성이 저하되는 경향을 보인다.In general, the organic semiconductor materials used to fabricate organic thin film transistors are packed only by interactions with van der Waals energy, so that the intermolecular attraction is not strong enough. As a result, the intermolecular bonding force is weak and the intermolecular distance is not close enough. It has the disadvantage that the mobility of the intermolecular carriers is not high enough. In addition, since the intermolecular packing is not sufficient, air or moisture is easily introduced into the semiconductor layer from the outside, and thus, the stability of the device tends to be lowered.
이러한 단점을 해결하기 위해, 본 발명은 유기 박막 트랜지스터를 제작함에 있어 유기 반도체 물질간의 결합력이 약한 반데르발스 결합보다 결합력이 강한 수소결합을 할 수 있는 화합물을 이용해서 유기 반도체층을 형성하는 것을 특징으로 한다. 일반적으로, 수소결합은 O, N, S, F 등과 같이 전기음성도가 큰 원자에 결합되어 있는 수소가 이웃한 다른 분자의 O, N, S, F 등의 원자의 비공유 전자쌍과 상호작용을 함으로써 생성된다. 이러한 O, N, S, F 등의 전기음성도는 수소 원자의 전기음성도보다 상당히 크므로, 수소 원자에는 부분적으로 양전하가 생성되고, O, N, S, F 등의 원자에는 부분적 음전하가 생성된다. 이러한 부분적 양전하를 띤 수 소원자가 인접한 음전하를 띤 산소, 질소, 황, 불소 등의 원자와 강한 인력을 나타내게 되므로 두 분자 사이의 거리가 매우 가깝게 패킹되며 일정하게 배열하기 쉽다. 이러한 분자간 패킹은 분자간 거리를 감소시킴으로써 반도체층 내의 캐리어 이동을 원활하게 할 수 있다. 또한, 수소결합에 의한 유기 반도체는 공기나 수분에 의한 전자 소자의 안정성을 증가시킬 수 있다. In order to solve this drawback, the present invention is characterized in that the organic semiconductor layer is formed by using a compound capable of hydrogen bonding stronger than van der Waals bonds weak bonding force between organic semiconductor materials in manufacturing an organic thin film transistor It is done. In general, hydrogen bonding is achieved by the interaction of hydrogen, which is bound to an electronegative atom such as O, N, S, or F, with an unshared pair of electrons, such as O, N, S, or F, of an adjacent molecule. Is generated. Since the electronegativity of O, N, S, F, etc. is considerably greater than the electronegativity of hydrogen atoms, partial charges are generated at the hydrogen atoms, and partial negative charges are generated at the atoms, such as O, N, S, and F. do. Since these partially positively charged hydrogen atoms exhibit strong attractive forces with adjacent negatively charged oxygen, nitrogen, sulfur, and fluorine atoms, the distance between the two molecules is very close to packing and is easy to arrange uniformly. Such intermolecular packing can facilitate carrier movement within the semiconductor layer by reducing the intermolecular distance. In addition, the organic semiconductor by hydrogen bonding can increase the stability of the electronic device by air or moisture.
본 발명에 따른 유기 박막 트랜지스터에 있어서, 상기 유기 반도체층은 수소결합을 할 수 있는 작용기를 갖는 화합물을 이용하여 당 기술분야에 알려진 방법으로 형성할 수 있다.In the organic thin film transistor according to the present invention, the organic semiconductor layer may be formed by a method known in the art using a compound having a functional group capable of hydrogen bonding.
통상적으로 유기 박막 트랜지스터의 제조시 반도체층을 형성하는 방법으로는 진공 증착법과 용액 도포법으로 나눌 수 있다. 구체적으로, 진공 증착법은 고온과 높은 진공도를 요구하므로 대면적화가 어려우며, 장비의 가격이 상대적으로 높고 공정이 비교적 복잡하다. 반면, 스핀 코팅법, 잉크젯 프린팅법, 딥코팅법, 롤코팅법, 스크린 프린팅법 등으로 대표되는 용액 도포법은 대면적의 박막형성이 가능하며 상온 상압하에서의 공정이 가능하므로 공정 단가를 낮출 수 있다는 장점이 있다.In general, a method of forming a semiconductor layer in manufacturing an organic thin film transistor may be classified into a vacuum deposition method and a solution coating method. Specifically, the vacuum deposition method requires high temperature and high degree of vacuum, making it difficult to large area, relatively expensive equipment, and relatively complicated process. On the other hand, the solution coating method represented by spin coating method, inkjet printing method, dip coating method, roll coating method, screen printing method, etc. is able to form a large area thin film and process at room temperature and atmospheric pressure, thereby lowering the process cost. There is an advantage.
그런데, 강한 분자간 상호작용을 갖는 화합물들은 분자 내로 유기 용매의 침투를 어렵게 하여 물질의 용해도가 낮은 경향이 있다.However, compounds having strong intermolecular interactions tend to make the penetration of organic solvents into molecules difficult, so that the solubility of the material is low.
따라서, 본 발명은 유기 박막 트랜지스터를 제작함에 있어 유기 반도체 물질간 수소결합의 장점을 이용하기 위하여, 수소결합이 가능한 작용기를 포함하는 유기 반도체 물질로 유기 반도체층을 형성함으로써 분자간 패킹과 결정화도를 높이 되, 진공 증착법을 이용하여 유기 반도체 층을 형성하거나, 분자 내로 유기 용매의 침투를 쉽게 하도록 수소 결합을 이루는 작용기에 벌키한 치환체를 도입함으로써 유기 반도체 물질의 용해도를 높게 하여, 상기 유기 반도체층을 용액 공정으로 형성하는 방법을 제공한다.Therefore, in order to take advantage of hydrogen bonding between organic semiconductor materials in fabricating an organic thin film transistor, an organic semiconductor layer is formed of an organic semiconductor material including a functional group capable of hydrogen bonding, thereby increasing intermolecular packing and crystallinity. Forming a semiconductor layer by vacuum deposition, or introducing a bulky substituent to a functional group that forms a hydrogen bond to facilitate penetration of the organic solvent into a molecule, thereby increasing the solubility of the organic semiconductor material, and It provides a method of forming.
구체적으로, 본 발명에 따른 유기 박막 트랜지스터의 유기 반도체층은 수소결합을 할 수 있는 작용기를 갖는 유기 반도체 물질에 의해 형성될 수 있다.Specifically, the organic semiconductor layer of the organic thin film transistor according to the present invention may be formed of an organic semiconductor material having a functional group capable of hydrogen bonding.
즉, N, O, S, F 원자 등에 결합되어 수소결합을 이루는 작용기를 포함하는 화합물의 상기 작용기에 열 또는 광(光)에 의해 제거될 수 있는 치환기를 도입하여 수소결합을 제거함으로써 분자간 상호작용을 약화시킨다. 특히, 상기 치환기가 용매에 대한 용해도를 증가시킬 수 있는 치환기, 예컨대 벌키(bulky)한 치환기인 경우, 상기 화합물의 용해도는 증가하여 용이하게 용액으로 제조될 수 있으므로, 제조된 용액을 이용하여 용액 도포법에 의해 박막을 형성할 수 있다. 이어서, 형성된 박막을 열 또는 광처리하여 상기 치환기를 제거함으로써 다시 수소결합을 형성할 수 있는 결합력이 강한 유기 반도체 물질이 생성된다. 따라서, 전술한 본 발명에 따른 유기 박막 트랜지스터의 제조방법은 용액 공정에 의해 박막을 형성하면서도 결과적으로 형성된 막이 수소결합에 의해 분자간 패킹과 결정화도가 높은 동시에 수분이나 공기에 대한 안정성을 우수하게 한다.That is, intermolecular interaction by removing a hydrogen bond by introducing a substituent which can be removed by heat or light into the functional group of the compound including a functional group bonded to N, O, S, F atoms or the like to form a hydrogen bond Weakens. In particular, when the substituent is a substituent capable of increasing solubility in a solvent, such as a bulky substituent, the solubility of the compound can be increased and easily prepared into a solution, so that the solution is applied using the prepared solution. A thin film can be formed by the method. Subsequently, the formed thin film is thermally or light-treated to remove the substituents, thereby forming an organic semiconductor material having a strong bonding force capable of forming hydrogen bonds again. Therefore, the above-described method for manufacturing an organic thin film transistor according to the present invention, while forming a thin film by a solution process, the resulting film has a high degree of intermolecular packing and crystallinity by hydrogen bonding and at the same time excellent stability to moisture or air.
본 발명에서 수소결합을 할 수 있는 작용기를 갖는 유기 반도체 물질로는 전술한 작용원리에 의하여 수소결합이 가능하고 반도체 역할을 할 수 있는 화합물이라면 그 종류에 제한되지 않고 사용될 수 있다.As the organic semiconductor material having a functional group capable of hydrogen bonding in the present invention, any compound capable of hydrogen bonding and capable of acting as a semiconductor according to the above-described principles of operation may be used without limitation.
이하, 본 발명에서 사용될 수 있는 화합물을 상세히 설명하기 위해 하기의 예를 들어 설명하나, 이는 단지 이해를 돕기 위한 것으로 이러한 예들에 한정되는 것은 아니다.Hereinafter, the following examples will be described in detail to describe the compounds that can be used in the present invention, but these are merely for the purpose of understanding and are not limited to these examples.
상기 수소결합을 할 수 있는 작용기를 갖는 유기 반도체 물질에서 수소 결합을 하는 작용기는 하기 화학식 1, 화학식 2 및 화학식 3으로 표시되는 화합물 중에 어느 하나의 화합물에 표시된 작용기일 수 있다.The functional group capable of hydrogen bonding in the organic semiconductor material having a functional group capable of hydrogen bonding may be a functional group represented by any one compound among the compounds represented by the following
하기 화학식 1 내지 3으로 표시된 화합물은 모두 케톤기와 수소결합이 가능한 NH기를 포함한다. 이들은 하기 구조식 1 또는 2와 같이 각각 수소결합을 이루어 강력한 상호작용을 한다. 따라서, 결합력이 강한 이들 화합물 또는 이들을 포함하는 유기 반도체 물질은 진공 증착에 의해 유기 반도체층으로 형성될 수 있다.The compounds represented by the following
상기 화학식 3에 있어서, Ar 및 Ar'는 각각 독립적으로 아릴기 및 헤테로 아릴기로 이루어진 군에서 선택된 것이 바람직하며, 이들은 알킬기, 알콕시기, 아세틸기, 티오알콕시기, 이민기, 에스터기, 니트릴기, 아미노기, 에스터기, 니트로기 등에 의해 치환될 수 있다. In Formula 3, Ar and Ar 'are each independently selected from the group consisting of aryl group and hetero aryl group, these are alkyl group, alkoxy group, acetyl group, thioalkoxy group, imine group, ester group, nitrile group, amino group , Ester group, nitro group and the like can be substituted.
<구조식 1><
<구조식 2> <Formula 2>
상기 수소결합을 하는 화합물에서 수소결합을 이루는 수소 원자를 t-부톡시 카보닐(t-butoxycarbonyl)기와 같은 벌키한 치환기로 치환하면 하기 화학식 4 또는 화학식 5와 같은 화합물로서 수소결합을 이루지 못하게 된다.When a hydrogen atom forming a hydrogen bond is replaced with a bulky substituent such as a t-butoxycarbonyl group in the compound that bonds with hydrogen, the compound does not form a hydrogen bond as the compound of Formula 4 or Formula 5 below.
상기 화학식 5에 있어서, Ar 및 Ar'는 각각 독립적으로 아릴기 및 헤테로 아릴기로 이루어진 군에서 선택된 것이 바람직하며, 이들은 알킬기 알콕시기, 아세틸기, 티오알콕시기, 이민기, 에스터기, 니트릴기, 아미노기, 에스터기, 니트로기 등에 의해 치환될 수 있다.In Formula 5, Ar and Ar 'are each independently selected from the group consisting of aryl group and hetero aryl group, these are alkyl group alkoxy group, acetyl group, thioalkoxy group, imine group, ester group, nitrile group, amino group, It may be substituted by an ester group, a nitro group, etc.
따라서, 화학식 4 및 5로 표시된 화합물은 매우 벌키한 치환기가 도입되어 수소결합을 이루지 못하므로 분자간 결합력이 약해지고, 용해도가 매우 증가하게 되어, 용액으로 제조될 수 있으므로 용액 공정에 의해 박막의 형성이 가능하다. 위의 화학식 4 및 화학식 5로 표시된 화합물은 수소원자가 t-부톡시카보닐기로 치환 된 것으로 열 또는 광처리에 의해 분자결합이 깨어져 다시 화학식 1과 화학식 3의 물질을 다시 형성할 수 있다.Therefore, the compounds represented by the formulas (4) and (5) do not form hydrogen bonds due to the introduction of very bulky substituents, thereby weakening the intermolecular bonding strength and increasing the solubility, and thus may be prepared as a solution, thus forming a thin film by a solution process. Do. Compounds represented by Formula 4 and Formula 5 above are hydrogen atoms substituted with t-butoxycarbonyl group, and the molecular bonds may be broken by heat or light treatment, thereby forming the materials of
구체적으로, 상기 화학식 1로 표시되는 화합물이 t-부톡시카보닐기로 치환되고 열에 의해 다시 수소결합이 가능한 화합물로 환원되는 반응을 하기 반응식 1 및 2로 설명할 수 있다. 그러나 이는 이해를 돕기 위한 것일 뿐 이들에 한정되는 것은 아니다. Specifically, a reaction in which the compound represented by
상기 반응식 1의 생성물은 출발 물질인 퀴나크리돈에 비하여 용해도가 매우 높아 용액 제조가 가능하다. 따라서, 이 생성물로 용액을 제조하고, 이를 용액 공 정에 의해 박막을 형성할 수 있다. 또한, 이와 같이 치환된 t-부톡시카보닐기는 열에 의해 이산화탄소와 이소프로펜으로 분해되어 완전히 제거될 수 있으며 처음의 퀴나크리돈 화합물이 다시 생성된다.The product of
또한, 수소결합을 할 수 있는 작용기를 갖는 유기 반도체 물질에서 수소결합을 이루는 작용기에 다른 치환기가 도입된 화합물은 열처리뿐만 아니라 광처리에 의해서도 수소결합을 할 수 있는 화합물로 생성될 수 있다. 이와 같이, 광처리를 이용하기 위해서는 박막 형성시 수소결합을 이루는 작용기에 다른 치환기가 도입된 화합물과 함께 광산발생제(PAG, photo acid generator)를 사용하는 것이 바람직하다. 광산발생제는 일반적으로 포토리소그래피법에 의한 패터닝(patterning)에 사용되는 물질이다. 구체적으로 t-부톡시카보닐기 등을 포함하는 화합물과 광산발생제를 혼합하여 박막 형성 후, 이 박막을 포토마스크를 이용하여 노광하면 빛에 노출된 부분에서 산(acid)이 생성되고 이들이 치환체로 도입된 t-부톡시카보닐기 등의 치환기를 떼어주는 역할을 하여 수소 결합이 다시 생성되고, 다시 생성된 수소결합에 의해 용해도 차이가 생겨나서 이를 이용하여 박막을 패터닝하는 것이다. In addition, in an organic semiconductor material having a functional group capable of hydrogen bonding, a compound in which another substituent is introduced into a functional group forming a hydrogen bond may be formed as a compound capable of hydrogen bonding not only by heat treatment but also by light treatment. As such, in order to use the light treatment, it is preferable to use a photo acid generator (PAG) together with a compound in which another substituent is introduced into a functional group that forms a hydrogen bond when forming a thin film. Photoacid generators are generally materials used for patterning by photolithography. Specifically, a compound including a t-butoxycarbonyl group and a photoacid generator are mixed to form a thin film, and then the thin film is exposed using a photomask to generate acids in the light-exposed areas, and these are used as substituents. It serves to remove substituents such as t-butoxycarbonyl group introduced, hydrogen bonds are regenerated, solubility difference is generated by the hydrogen bonds again, and the thin film is patterned using them.
본 발명에 있어서는 상기 수소결합을 이루는 작용기에 다른 치환기가 도입된 화합물과 광산발생제를 혼합하여 박막을 형성하고 이 박막을 노광함으로써 수소결합을 하는 화합물로 이루어진 유기 반도체층을 형성할 수 있다. 이와 같이, 광산발생제를 이용한 광처리 방법은 패터닝된 전자 소자를 형성하기가 용이하다. 이때, 광산발생제의 함량은 유기 반도체 화합물에 대해 특별히 제한이 없으나, 10% 미만인 것이 바람직하다.In the present invention, a thin film is formed by mixing a compound having a different substituent introduced with a functional group forming a hydrogen bond with a photoacid generator to form a thin film, and the organic semiconductor layer made of a compound having a hydrogen bond can be formed by exposing the thin film. As such, the light treatment method using the photoacid generator is easy to form the patterned electronic device. In this case, the content of the photoacid generator is not particularly limited to the organic semiconductor compound, but is preferably less than 10%.
상기 광산발생제의 예로는 특별히 한정되지 않으나, 디아릴요오드늄염(diaryliodonium salt), 트리아릴설포늄염(triarylsulfonium salt), 이미도 설포네이트(imido sulfonates), 4-니트로벤젠설폰산 유도체(4-nitrobenzenesulfonic acid derivatives), 디설폰 화합물(disulphone compounds), 설포닐 치환 디아조메탄(sulfonyl substituted diazomethanes), 디벤질 설폰 아릴-비스-트리클로로메틸-s-트리아진(dibenzyl sulfones aryl-bis-trichloromethyl-s-triazine) 등이 있으며, 이들은 빛에 의해 깨어지면서 양자산(protic acid)를 형성한다.Examples of the photoacid generator include, but are not particularly limited to, diaryliodonium salt, triarylsulfonium salt, imido sulfonates, and 4-nitrobenzenesulfonic acid derivatives. acid derivatives, disulphone compounds, sulfonyl substituted diazomethanes, dibenzyl sulfones aryl-bis-trichloromethyl-s- triazine), which are broken by light to form protic acid.
상기 열 또는 광에 의한 수소결합 분자의 재형성은 흔히 유기 화학 반응에서 작용기의 프로텍션(protection)과 디프로텍션(deprotection)에서 사용되는 방법이다. 이때 수소결합을 이루는 작용기 대신에 치환되는 치환기는 상기 화학식 4 및 5로 표시된 화합물의 치환기인 t-부톡시카보닐 만으로 한정되는 것은 아니다. 일반적으로 수소결합을 이루는 알코올기, 페놀기, 카테콜기, 카보닐기, 티올기, 아민기 등은 에테르(ether) 결합, 에스터 (ester)결합, 티오에테르(thioether) 결합, 티오에스터(thioester) 결합, 아마이드(amide) 결합 등으로 프로텍션될 수 있다.Re-formation of hydrogen-bonded molecules by heat or light is often the method used in the protection and deprotection of functional groups in organic chemical reactions. In this case, the substituent substituted in place of the hydrogen bond functional group is not limited to t-butoxycarbonyl, which is a substituent of the compounds represented by Formulas 4 and 5. In general, the alcohol group, phenol group, catechol group, carbonyl group, thiol group, amine group, etc., which form hydrogen bonds, are ether (ether), ester (ester), thioether (thioether), thioester (thioester) It may be protected by an amide bond, and the like.
상기 치환체들을 열처리 또는 광처리에 의해 수소 결합을 다시 유도함에 있어서 열처리 온도나 시간에 특별히 제한은 없으며, 치환기들의 종류에 따라 선택할 수 있다. 예컨대, 온도는 20 ℃ 내지 350 ℃ 범위가 바람직하며, 시간은 1분 내지 2시간 이내에 처리되는 것이 바람직하다. 더 바람직하게는 150 ℃ 이내의 온도에서 처리되는 것이 바람직하며 시간은 30분 이내에 처리되는 것이 바람직하다. In inducing hydrogen bonds again by heat treatment or light treatment, the substituents are not particularly limited in heat treatment temperature or time, and may be selected according to the types of substituents. For example, the temperature is preferably in the range of 20 ° C to 350 ° C, and the time is preferably treated within 1 minute to 2 hours. More preferably, the treatment is preferably carried out at a temperature within 150 ° C. and the time is preferably treated within 30 minutes.
광처리를 수행함에 있어서, 노광 시간의 경우 특별히 제한을 두지 않으나 일 반적으로 30분 미만인 것이 바람직하다.In performing the light treatment, the exposure time is not particularly limited but is generally less than 30 minutes.
또한, 광산 발생제를 사용하는 경우에 광원은 자외선 또는 가시광선을 사용하며 그 파장에 특별히 제한을 두지 않으나 일반적으로 사용하는 180 nm 내지 700 nm가 바람직하다. In addition, in the case of using a photoacid generator, the light source uses ultraviolet rays or visible light, and the wavelength is not particularly limited, but 180 nm to 700 nm is generally used.
또한, 광산발생제를 사용하여 광처리를 하는 경우에도 열처리를 동반할 수 있으며 이 경우에 열처리 온도는 열처리만을 이용하는 것에 비해 상대적으로 낮은 온도를 이용할 수 있다. In addition, even when the light treatment using the photoacid generator may be accompanied by a heat treatment, in this case, the heat treatment temperature may be used relatively low temperature compared to using only the heat treatment.
하기에 각각의 수소결합 작용기에 적합한 치환기를 설명한다.The substituent suitable for each hydrogen bond functional group is demonstrated below.
수소결합을 이루는 작용기가 알코올기일 경우, 알코올기 대신에 치환되는 작용기는 메틸 에테르(methyl ether), 메톡시메틸 에테르(methoxymethyl ether), 메톡시티오메틸 에테르(methoxythiomethyl ether), 2-메톡시에톡시메틸 에테르(2-methoxyethoxymethyl ether), 비스(2-클로로에톡시)메틸 에테르(bis(2-chloroethoxy)methyl ether), 테트라히드로피라닐 에테르(tetrahydropyranyl ether), 4-메톡시테트라히드로피라닐 에테르(4-methoxytetrahydropyranyl ether), 테트라히드로티오피라닐 에테르(tetrahydrothiopyranyl ether), 4-메톡시테트라히드로피라닐 에테르(4-methoxytetrahydropyranyl ether), 4-메톡시테트라히드로티오피라닐 에테르(4-methoxythetrahydrothiopyranyl ether), 테트라히드로퓨라닐 에테르(tetrahydrofuranyl ether), 테트라히드로티오퓨라닐 에테르(tetrahydrothiofuranyl ether), 1-에톡시에틸 에테르(1-ethoxyethyl ether), 1-메틸-1-메톡시에틸 에테르(1-methyl-1-methoxyethyl ether), 2-(페닐셀레닐)에틸 에테르(2-(phenylselenyl)ethyl ether, t-부틸 에테르(t-butyl ether), 알릴 에테르(allyl ether), 벤질 에테르(benzyl ether), o-니트로벤질 에테르(o-nitrobenzyl ether), 트리페닐메틸 에테르(triphenylmethyl ether), a-나프틸디페닐메틸 에테르(a-naphthyldiphenylmethyl ether), p-메톡시페닐디페닐메틸 에테르(p-methoxyphenyldiphenylmethyl ether), 9-(9-페닐-10-옥소)안트릴 에테르(9-(9-phenyl-10-oxo)anthryl ether), 트리메틸실릴 에테르(trimethylsilyl ether), 이소프로필디메틸실릴 에테르(isopropyldimethylsilyl ether), t-부틸디메틸실릴 에테르(t-butyldimethylsilyl ether), t-부틸디페틸실릴 에테르(t-butyldiphenylsilyl ether), 트리벤질실릴 에테르(tribenzylsilyl ether), 트리이소프로필실릴 에테르(triisopropylsilyl ether), 포메이트 에스테르(formate ester), 아세테이트 에스테르(acetate ester), 트리클로로아세테이트 에스테르(trichloroacetate ester), 페녹시아세테이트 에스테르(phenoxyacetate ester), 이소부티레이트 에스테르(isobutyrate ester), 피발로에이트 에스테르(pivaloate ester), 아다만토에이트 에스테르(adamantoate ester), 벤조에이트 에스테르(benzoate ester), 2,4,6-트리메틸벤조에이트 에스테르(2,4,6-trimethylbenzoate ester), 메틸 카보네이트(methyl carbonate, 2,2,2-트리클로로에틸 카보네이트(2,2,2-trichloroethyl carbonate), 알릴 카보네이트(allyl carbonate), p-니트로페닐 카보네이트(p-nitrophenyl carbonate), 벤질 카보네이트(benzyl carbonate), s-벤질 티오카보네이트(s-benzyl thiocarbonate), N-페닐 카보네이트(N-phenyl carbonate), 니트레이트 에스테르(nitrate ester), 2,4-디니트로페닐 술페네이트 에스테르(2,4-dinitrophenylsulfenate ester) 등을 포함한다.When the hydrogen bonding functional group is an alcohol group, the functional group substituted in place of the alcohol group is methyl ether, methoxymethyl ether, methoxythiomethyl ether, 2-methoxyethoxy 2-methoxyethoxymethyl ether, bis (2-chloroethoxy) methyl ether, tetrahydropyranyl ether, 4-methoxytetrahydropyranyl ether ( 4-methoxytetrahydropyranyl ether, tetrahydrothiopyranyl ether, 4-methoxytetrahydropyranyl ether, 4-methoxythetrahydrothiopyranyl ether, Tetrahydrofuranyl ether, tetrahydrothiofuranyl ether, 1-ethoxyethyl ether, 1-methyl-1-me 1-methyl-1-methoxyethyl ether, 2- (phenylselenyl) ethyl ether, 2- (phenylselenyl) ethyl ether, t-butyl ether, allyl ether, Benzyl ether, o-nitrobenzyl ether, triphenylmethyl ether, a-naphthyldiphenylmethyl ether, p-methoxyphenyldiphenylmethyl P-methoxyphenyldiphenylmethyl ether, 9- (9-phenyl-10-oxo) anthryl ether (9- (9-phenyl-10-oxo) anthryl ether), trimethylsilyl ether, isopropyldimethylsilyl Isopropyldimethylsilyl ether, t-butyldimethylsilyl ether, t-butyldiphenylsilyl ether, t-butyldiphenylsilyl ether, tribenzylsilyl ether, triisopropylsilyl ether ), Formate esters, acetate esters er), trichloroacetate ester, phenoxyacetate ester, isobutyrate ester, pivaloate ester, adamantoate ester, benzoate Benzoate ester, 2,4,6-trimethylbenzoate ester, methyl carbonate, 2,2,2-trichloroethyl carbonate (2,2,2- trichloroethyl carbonate, allyl carbonate, p-nitrophenyl carbonate, benzyl carbonate, s-benzyl thiocarbonate, N-phenyl carbonate carbonate, nitrate ester, 2,4-dinitrophenylsulfenate ester, and the like.
바람직하게는, 수소결합을 이루는 작용기가 알코올기일 경우, 알코올기 대신에 치환되는 작용기는 트리클로로아세테이트 에스테르(trichloroacetate ester), 메틸 카보네이트(methyl carbonate), 2,2,2-트리클로로에틸 카보네이트(2,2,2-trichloroethyl carbonate), 알릴 카보네이트(allyl carbonate), p-니트로페닐 카보네이트(p-nitrophenyl carbonate), 벤질 카보네이트(benzyl carbonate), s-벤질 티오카보네이트(s-benzyl thiocarbonate), 니트레이트 에스테르(nitrate ester) 및 2,4-디니트로페닐설펜네이트 에스테르(2,4-dinitrophenylsulfenate ester)을 포함한다.Preferably, when the functional group forming a hydrogen bond is an alcohol group, the functional group substituted in place of the alcohol group is trichloroacetate ester, methyl carbonate, 2,2,2-trichloroethyl carbonate (2 , 2,2-trichloroethyl carbonate, allyl carbonate, p-nitrophenyl carbonate, benzyl carbonate, s-benzyl thiocarbonate, nitrate ester (nitrate ester) and 2,4-dinitrophenylsulfenate ester.
더 바람직하게는, 수소결합을 이루는 작용기가 알코올기일 경우, 알코올기 대신에 치환되는 작용기는 니트레이트 에스테르(nitrate ester) 및 2,4-디니트로페닐설펜네이트 에스테르(2,4-dinitrophenylsulfenate ester)를 포함한다.More preferably, when the hydrogen bonding functional group is an alcohol group, the functional group substituted in place of the alcohol group may include nitrate ester and 2,4-dinitrophenylsulfenate ester. Include.
수소결합을 이루는 작용기가 페놀기나 카테콜기일 경우, 페놀기나 카테콜기 대신에 치환되는 작용기는 메틸 에테르(methyl ether), 메톡시메틸 에테르(methoxymethyl ether), 2-메톡시에톡시메틸 에테르(2-methoxyethoxymethyl ether), 메톡시티오메틸 에테르(methoxythiomethyl ether), 페나실 에테르(penacyl ether), 알릴 에테르(allyl ether), 시클로헥실 에테르(cyclohexyl ether), t-부틸 에테르(t-butyl ether), 벤질 에테르(benzyl ether), o-니트로벤질 에테르(o-nitrobenzyl ether), 9-안트릴메틸 에테르(9-anthrylmethyl ether), 4-피콜릴 에테르(4-picolyl ether), t-부틸디메틸실릴 에테르(t-butyldimethylsilyl ether), 아 릴 아세테이트(aryl acetate), 아릴 피발로에이트(aryl pivaloate), 아릴 벤조에이트(aryl benzoate), 아릴 9-플루오렌카복실레이트(aryl 9-fluorenecarboxylate), 아릴 메틸 카보네이트(aryl methyl carbonate), 아릴 2,2,2-트리클로로에틸 카보네이트(aryl 2,2,2-trichloroethyl carbonate), 아릴 비닐 카보네이트(aryl vinyl carbonate), 아릴 벤질 카보네이트(aryl benzyl carbonate), 아릴 메탄술포네이트(aryl methanesulfonate), 메틸렌디옥시 유도체(methylenedioxy derivatives), 아세토나이드 유도체(acetonide derivatives), 디페닐메틸렌디옥시 유도체(diphenylmethylenedioxy derivatives), 시클릭 보레이트(cyclic borate), 시클릭 카보네이트(cyclic carbonate) 등을 포함한다. When the hydrogen bonding functional group is a phenol group or catechol group, the functional group substituted in place of the phenol group or catechol group is methyl ether, methoxymethyl ether, 2-methoxyethoxymethyl ether (2- methoxyethoxymethyl ether, methoxythiomethyl ether, phenacyl ether, allyl ether, cyclohexyl ether, t-butyl ether, benzyl ether (benzyl ether), o-nitrobenzyl ether, 9-anthrylmethyl ether, 4-picolyl ether, t-butyldimethylsilyl ether (t butyldimethylsilyl ether, aryl acetate, aryl pivaloate, aryl benzoate, aryl 9-fluorenecarboxylate, aryl methyl carbonate carbonate), aryl 2,2,2-trichloro Aryl 2,2,2-trichloroethyl carbonate, aryl vinyl carbonate, aryl benzyl carbonate, aryl methanesulfonate, methylenedioxy derivatives, Acetonide derivatives, diphenylmethylenedioxy derivatives, cyclic borates, cyclic carbonates, and the like.
수소결합을 이루는 작용기가 카보닐일 경우, 카보닐기 대신에 치환되는 작용기는 디메틸 아세탈과 케탈(dimethyl acetal and ketal), 비스(2,2,2-트리클로로에틸)아세탈과 케탈(bis(2,2,2-trichloroethyl acetal and ketal), 1,3-디옥센(1,3-dioxanes), 5-메틸렌-1,3-디옥센(5-methylene-1,3-dioxanes), 5,5,-디브로모-1,3-디옥센(5,5-dibromo-1,3-dioxanes), 1,3-디옥소랜(1,3-dioxolanes), 4-브로모메틸-1,3-디옥소랜(4-bromomethyl-1,3-dioxolanes), 4-o-니트로페닐-1,3-디옥소랜(4-o-nitrophenyl-1,3-dioxolanes), S,S'-디메틸 아세탈과 케탈(S,S'-dimethyl acetal and ketal), 1,3-디티안(1,3-dithianes), 1,3-디티올랜(1,3-dithiolane), 1,3-옥사티올랜(1,3-oxathiolanes), o-트리메틸실릴 시아노히드린(o-trimethylsilyl cyanohydrins), N,N-디메틸히드라존(N,N-dimethylhydrazones), 2,4-디니트로페닐히드라존(2,4-dinitrophenylhydrazones), o-페닐티오메틸 옥심(o-phenylthiomethyl oximes), 치환된 메틸렌 유도체(substituted methylene derivatives), 비스메틸렌디옥시 유도체(bismethylenedioxy derivatives), 메틸 에스테르(methyl ester), 메톡시메틸 에스테르(methoxymethyl ester), 메틸티오메틸 에스테르(methylthiomethyl ester), 테트라히드로피라닐 에스테르(tetrahydropiranyl ester), 벤질옥시메틸 에스테르(benzyloxymethyl ester), 페나실 에스테르(penacyl ester), N-프탈이미도메틸 에스테르(N-phthalimidomethyl ester), 2,2,2-트리클로로에틸 에스테르(2,2,2-trichloroethyl ester), 2-할로에틸 에스테르(2-haloethyl ester), 2-(p-톨루엔술포닐)에틸 에스테르(2-(p-toluenesulfonyl)ethyl ester), t-부틸 에스테르(t-butyl ester), 시나밀 에스테르(cinnamyl ester), 벤질 에스테르(benzy ester), 트리페닐메틸 에스테르(triphenylmethyl ester), 비스(o-니트로페닐)메틸 에스테르(bis(o-nitrophenylmethyl ester), 9-안트릴메틸 에스테르(9-anthrylmethyl ester), 2-(9,10-디옥소)안트릴메틸 에스테르(2-(9,10-dioxo)anthrylmethyl ester), 피페로닐 에스테르(piperonyl ester), 트리메틸실릴 에스테르(trimethylsilyl ester), t-부틸디메틸실릴 에스테르(t-butyldimethylsilyl ester), s-t-부틸 에스테르(s-t-butyl ester), 2-알킬-1,3-옥사졸린(2-alkyl-1,3-oxazolines), N,N-디메틸아미드(N,N-dimethylamide), N-7-니트로인도일아미드(N-7-nitroindoylamide), 히드라자이드(hydrazide), N-페닐히드라지드(N-phenylhydrazide), N,N'-디이소프로필히드라지드(N,N'-diisopropylhydrizide) 등을 포함한다. When the hydrogen bonding functional group is carbonyl, the functional group substituted in place of the carbonyl group is dimethyl acetal and ketal, bis (2,2,2-trichloroethyl) acetal and ketal (bis (2,2) , 2-trichloroethyl acetal and ketal), 1,3-dioxanes, 5-methylene-1,3-dioxanes, 5-methylene-1,3-dioxanes, 5,5,- Dibromo-1,3-dioxenes (5,5-dibromo-1,3-dioxanes), 1,3-dioxolanes, 4-bromomethyl-1,3-di With 4-bromomethyl-1,3-dioxolanes, 4-o-nitrophenyl-1,3-dioxolanes, S, S'-dimethyl acetal S, S'-dimethyl acetal and ketal, 1,3-dithianes, 1,3-dithiolane, 1,3-oxathiolane , 3-oxathiolanes), o-trimethylsilyl cyanohydrins, N, N-dimethylhydrazones, 2,4-dinitrophenylhydrazones ), o-phenylthiomethyl oximes, substitution Methylene derivatives, bismethylenedioxy derivatives, methyl esters, methoxymethyl esters, methoxymethyl esters, methylthiomethyl esters, tetrahydropiranyl esters esters, benzyloxymethyl esters, penacyl esters, N-phthalimidomethyl esters, 2,2,2-trichloroethyl esters (2,2,2- trichloroethyl ester, 2-haloethyl ester, 2- (p-toluenesulfonyl) ethyl ester, t-butyl ester, Cinnamic ester, benzyl ester, triphenylmethyl ester, o-nitrophenylmethyl ester, 9-antrylmethyl ester -anthrylmethyl ester), 2- (9,10 -Dioxo) anthrylmethyl ester (2- (9,10-dioxo) anthrylmethyl ester), piperonyl ester, trimethylsilyl ester, t-butyldimethylsilyl ester ), st-butyl ester, 2-alkyl-1,3-oxazolines, N, N-dimethylamide, N -7-nitroindoylamide, hydrazide, N-phenylhydrazide, N, N'-diisopropylhydrizide, etc. It includes.
수소결합을 이루는 작용기가 티올기일 경우, 티올기 대신에 치환되는 작용기 는 s-벤질 티오에테르(s-benzyl thioether), s-p-메톡시벤질 티오에테르(s-p-methoxybenzyl thioether), s-p-니트로벤질 티오에테르(s-p-nitrobenzyl thioether), s-4-피콜릴 티오에테르(s-4-picolyl thioether), s-2-피콜릴 N-옥사이드 티오에테르(s-2-picolyl N-oxide thioether), s-9-안트릴메틸 티오에테르(s-9-anthrylmethyl thioether), s-디페니메틸 티오에테르(s-diphenylmethyl thioether), s-디(p-메톡시페닐)메틸 티오에테르(s-di(p-methoxyphenyl)methyl dithioether), s-트리페닐메틸 티오에테르(s-triphenylmethyl thioether), s-2,4-디니트로페닐 티오에테르(s-2,4-dinitrophenyl thioether), s-t-부틸 티오에테르(s-t-butyl thioether), s-이소부톡시메틸 모노티오아세탈(s-isobutoxymethyl monothioacetal), s-2-테트라히드로피라닐 모노티오아세탈(s-2-tetrahydropiranyl monothioacetal), s-아세트아미도메틸 아미노티오아세탈(s-acetamidomethyl aminothioacetal), s-시아노메틸 티오에테르(s-cyanomethyl thioether), s-2-니트로-1-페닐에틸 티오에테르(s-2-nitro-1-phenylethyl thioether), s-2,2-비스(카보에톡시)에틸 티오에테르(s-2,2-bis(carboethoxy)ethyl thioether), s-벤조일 유도체(s-benzoyl derivatives), s-(N-에틸카바메이트)(s-(N-ethylcarbamate), s-에틸 디술피드(s-ethyl disulfide) 등를 포함한다.When the hydrogen bonding functional group is a thiol group, the functional group substituted in place of the thiol group is s-benzyl thioether, sp-methoxybenzyl thioether, sp-nitrobenzyl thioether (sp-nitrobenzyl thioether), s-4-picolyl thioether, s-2-picolyl N-oxide thioether, s-9 S-9-anthrylmethyl thioether, s-diphenylmethyl thioether, s-di (p-methoxyphenyl) methyl thioether (s-di (p-methoxyphenyl) methyl dithioether, s-triphenylmethyl thioether, s-2,4-dinitrophenyl thioether, st-butyl thioether thioether, s-isobutoxymethyl monothioacetal, s-2-tetrahydropyranyl monothioacetal, s-acet S-acetamidomethyl aminothioacetal, s-cyanomethyl thioether, s-2-nitro-1-phenylethyl thioether (s-2-nitro-1-phenylethyl thioether), s-2,2-bis (carboethoxy) ethyl thioether (s-2,2-bis (carboethoxy) ethyl thioether), s-benzoyl derivatives, s- (N-ethyl Carbamate) (s- (N-ethylcarbamate), s-ethyl disulfide, and the like).
수소결합을 이루는 작용기가 아민기일 경우, 아민기 대신에 치환되는 작용기는 메틸 카바메이트(methyl carbamate), 9-플로레닐메틸 카바메이트(9-fluorenylmethyl carbamate), 2,2,2-트리클로로에틸 카바메이트(2,2,2-trichloroethyl carbamate), 2-트리메틸실릴에틸 카바메이트(2-trimethylsilyl carbamate), 1,1-디메틸프로피닐 카바메이트(1,1-dimethylpropynyl carbamate), 1-메틸-1-페닐에틸 카바메이트(1-methyl-1-phenylethyl catbamate), 1-메틸-1-(4-비페닐릴)에틸 카바메이트(1-methyl-1-(4-biphenylyl)ethyl carbamate), 1,1-디메틸-2-할로에틸 카바메이트(1,1-dimethyl-2-haloethyl carbamate), 1,1-디메틸-2-시아노에틸 카바메이트(1,1-dimethyl-2-cyanoethyl carbamate), t-부틸 카바메이트(t-butyl carbamate), 시클로부틸 카바메이트(cyclobutyl carbamate), 1-메틸시클로부틸 카바메이트(1-methylcyclobutyl carbamate), 1-아다만틸 카바메이트(1-adamantyl carbamate), 비닐 카바메이트(vinyl carbamate), 알릴 카바메이트(allyl carbamate), 신나밀 카바메이트(cinnamyl carbamate), 8-퀴놀릴 카바메이트(8-quinolyl carbamate), N-히드록시피페리디닐 카바메이트(N-hydroxypiperidinyl carbamate), 4,5-디페닐-3-옥사졸린-2-온(4,5-diphenyl-3-oxazoline-2-one), 벤질 카바메이트(benzyl carbamate), p-니트로벤질 카바메이트(p-nitrobenzyl carbamate), 3,4-디메톡시-6-니트로벤질 카바메이트(3,4-dimethoxy-6-nitrobenzyl carbamate), 2,4-디클로로벤질 카바메이트(2,4-dichlorobenzyl carbamate), 5-벤즈이속사졸릴메틸 카바메이트(5-benzisoxazolylmethyl carbamate), 9-안트릴메틸 카바메이트(9-anthrylmethyl carbamate), 디페닐메틸 카바메이트(diphenylmethyl carbamate), 이소니코티닐 카바메이트(isonicotinyl carbamate), s-벤질 카바메이트(s-benzyl carbamate), N-(N'-페닐아미노티오카보닐)유도체(N-(N'-phenylaminothiocarbonyl) derivatice), N-포밀(N-formyl), N-아세틸(N-acetyl), N-클로로아세틸(N-chloroacetyl), N-트리클로로아세틸(N-trichloroacetyl), N-트리 플로로아세틸(N-trifluoroacetyl), N-o-니트로페닐아세틸(N-o-nitrophenylacetyl), N-o-니트로페녹시아세틸(N-o-nitrophenoxyacetyl), N-아세토아세틸(N-acetoacetyl), N-3-페닐프로피오닐(N-3-phenylpropionyl), N-3-(p-히드록시페닐)프로피오닐(N-3-(p-hydroxyphenyl)propionyl), N-2-메틸-2-(o-니트로페녹시)프로피오닐(N-2-methyl-2-(o-nitrophenoxy)propionyl), N-2-메틸-2-(o-페닐아조페녹시)프로피오닐(N-2-methyl-2-(o-phenylazophenoxy)propionyl), N-4-클로로부티릴(N-4-chlorobutyryl), N-o-니트로신나모일(N-o-nitrocinnamoyl), N-피코리노일(N-picolinoyl), N-(N'-아세틸메티오닐)(N-(N'-acetylmethionyl), N-벤조일(N-benzoyl), N-프탈로일(N-phthaloyl), N-디티아숙시노일(N-dithiasuccinoyl), N-알릴(N-allyl), N-페나실(N-phenacyl), N-3-아세톡시프로필(N-3-acetoxypropyl), 4가 암모늄 염(quaternary ammonium salt), N-메톡시메틸(N-methoxymethyl), N-벤질옥시메틸(N-benzyloxymethyl), N-피발로일옥시메틸(N-pivaloyloxymethyl), N-테트라히드로피라닐(N-tetrahydropyranyl), N-2,4-디니트로페닐(N-2,4-dinitrophenyl), N-벤질(N-benzyl), N-o-니트로벤질(N-o-nitrobenzyl), N-디(p-메톡시페닐)메틸(N-di(p-methoxyphenyl)methyl), N-트리페닐메틸(N-triphenylmethyl), N-(p-메톡시페닐)디페닐메틸(N-(p-methoxyphenyl)diphenylmethyl), N-디페닐-4-피리딜메틸(N-diphenyl-4-pyridylmethyl), N-2-피콜릴 N'-옥사이드(N-2-picolyl N'-oxide), N,N'-이소프로필리덴(N,N'-isopropylidene), N-벤질리덴(N-benzylidene), N-p-니트로벤질리덴(N-p-nitrobenzylidene), N-살리실리덴(N-salicylidene), N-(5,5-디메틸-3-옥소-1-시클로헥세닐)(N-(5,5-dimethyl-3-oxo-1-cyclohexenyl), N-니트로(N- nitro), N-옥사이드(N-oxide), N-디페닐포스피닐(N-diphenylphosphinyl), N-디메틸티오포스피닐(N-dimethylthiophosphinyl), N-벤젠술페닐(N-benzenesulfenyl), N-o-니트로벤젠술페닐(N-o-nitrobenzenesulfenyl), N-2,4,6-트리메틸벤젠술포닐(N-2,4,6-trimethylbenzenesulfonyl), N-톨루엔술포닐(N-toluenesulfonyl), N-벤질술포닐(N-benzylsulfonyl), N-트리플로로메틸술포닐(N-trifluoromethylsulfonyl), N-페나실술포닐(N-phenacyl sulfonyl) 등을 포함한다.When the hydrogen bonding functional group is an amine group, the functional group substituted in place of the amine group is methyl carbamate, 9-fluorenylmethyl carbamate, 2,2,2-trichloroethyl carba 2,2,2-trichloroethyl carbamate, 2-trimethylsilyl carbamate, 1,1-dimethylpropynyl carbamate, 1-methyl-1- Phenylethyl carbamate, 1-methyl-1- (4-biphenylyl) ethyl carbamate, 1,1 1,1-dimethyl-2-haloethyl carbamate, 1,1-dimethyl-2-cyanoethyl carbamate, t- T-butyl carbamate, cyclobutyl carbamate, 1-methylcyclobutyl carbamate, 1-adamantyl carbamate , Vinyl carbamate, allyl carbamate, cinnamyl carbamate, 8-quinolyl carbamate, N-hydroxypiperidinyl carbamate (N -hydroxypiperidinyl carbamate, 4,5-diphenyl-3-oxazoline-2-one, benzyl carbamate, p-nitrobenzyl carbamate (p-nitrobenzyl carbamate), 3,4-dimethoxy-6-nitrobenzyl carbamate, 2,4-dichlorobenzyl carbamate, 5-benzisoxazolylmethyl carbamate, 9-anthrylmethyl carbamate, diphenylmethyl carbamate, isicotinyl carbamate, sicotinyl carbamate, s S-benzyl carbamate, N- (N'-phenylaminothiocarbonyl) derivative (N- (N'-phenylaminothiocarbonyl) derivatice), N-formyl ( N-formyl, N-acetyl, N-chloroacetyl, N-trichloroacetyl, N-trifluoroacetyl, No-nitro No-nitrophenylacetyl, No-nitrophenoxyacetyl, N-acetoacetyl, N-3-phenylpropionyl, N-3- ( p-hydroxyphenyl) propionyl (N-3- (p-hydroxyphenyl) propionyl), N-2-methyl-2- (o-nitrophenoxy) propionyl (N-2-methyl-2- (o- nitrophenoxy) propionyl), N-2-methyl-2- (o-phenylazophenoxy) propionyl (N-2-methyl-2- (o-phenylazophenoxy) propionyl), N-4-chlorobutyryl (N -4-chlorobutyryl), No-nitrocinnamoyl, N-picolinoyl, N- (N'-acetylmethionyl) (N- (N'-acetylmethionyl), N- N-benzoyl, N-phthaloyl, N-dithiasuccinoyl, N-allyl, N-phenacyl, N -3-acetoxypropyl, tetravalent cancer Quaternary ammonium salt, N-methoxymethyl, N-benzyloxymethyl, N-pivaloyloxymethyl, N-tetrahydropyranyl ( N-tetrahydropyranyl), N-2,4-dinitrophenyl, N-benzyl, No-nitrobenzyl, N-di (p-meth) N-di (p-methoxyphenyl) methyl, N-triphenylmethyl, N- (p-methoxyphenyl) diphenylmethyl, N- (p-methoxyphenyl) diphenylmethyl, N-diphenyl-4-pyridylmethyl, N-2-picolyl N'-oxide, N, N'-isopropylidene (N, N'-isopropylidene), N-benzylidene, Np-nitrobenzylidene, N-salicylidene, N- (5,5-dimethyl -3-oxo-1-cyclohexenyl) (N- (5,5-dimethyl-3-oxo-1-cyclohexenyl), N-nitro, N-oxide, N- Diphenylphosphinyl (N-diphenylphosphinyl), N-dimethylthiophosphinyl (N-dimethylthiopho sphinyl), N-benzenesulfenyl, No-nitrobenzenesulfenyl, N-2,4,6-trimethylbenzenesulfonyl (N-2,4,6-trimethylbenzenesulfonyl), N-toluenesulfonyl, N-benzylsulfonyl, N-trifluoromethylsulfonyl, N-phenacyl sulfonyl and the like do.
바람직하게는, 수소결합을 이루는 작용기가 아민기일 경우, 아민기 대신에 치환되는 작용기는 1,1-디메틸-2-할로에틸 카바메이트(1,1-dimethyl-2-haloethyl carbamate), 1,1-디메틸-2-시아노에틸 카바메이트(1,1-dimethyl-2-cyanoethyl carbamate), t-부틸 카바메이트(t-butyl carbamate) 및 N-(N'-아세틸메티오닐(N-(N'-acetylmethionyl))을 포함한다.Preferably, when the functional group forming a hydrogen bond is an amine group, the functional group substituted in place of the amine group may be 1,1-dimethyl-2-haloethyl carbamate, 1,1 1,1-dimethyl-2-cyanoethyl carbamate, t-butyl carbamate and N- (N'-acetylmethionyl (N- (N ')) -acetylmethionyl)).
더 바람직하게는, 수소결합을 이루는 작용기가 아민기일 경우, 아민기 대신에 치환되는 작용기는 1,1-디메틸-2-할로에틸 카바메이트(1,1-dimethyl-2-haloethyl carbamate) 및 t-부틸 카바메이트(t-butyl carbamate)를 포함한다.More preferably, when the functional group forming a hydrogen bond is an amine group, the functional group substituted in place of the amine group is 1,1-dimethyl-2-haloethyl carbamate and t- T-butyl carbamate.
가장 바람직하게는 수소결합을 이루는 작용기가 아민기인 경우, 상기 작용기가 t-부틸 카바메이트(t-butyl carbamate)인 것이다.Most preferably, when the functional group forming a hydrogen bond is an amine group, the functional group is t-butyl carbamate.
상기와 같은 치환기로 프로텍션된 수소결합을 하는 작용기를 갖는 화합물은 그 물질 자체로도 유기 반도체 물질로서 사용될 수 있다.The compound having a functional group that is hydrogen bond protected with the above substituents can be used as an organic semiconductor material as the material itself.
또한, 수소결합을 하는 작용기를 갖는 화합물은 유기 반도체 성질을 가지는 것으로 잘 알려진 티오펜계 유도체, 아센계 유도체, 포피린계 유도체 등이 도입된 화합물이 바람직하며, 구체적으로 하기 화학식 6 내지 16으로 표시된 화합물이 될 수 있으며, 이들은 유기 반도체 특성을 더 좋게 할 수도 있다. 그러나, 하기의 예들은 이해를 돕기 위한 것으로 이들에 한정되는 것은 아니다. In addition, a compound having a functional group that bonds hydrogen is preferably a compound in which thiophene derivatives, acene derivatives, porphyrin derivatives and the like, which are well known to have organic semiconductor properties, are introduced. These may be, and they may make the organic semiconductor properties better. However, the following examples are provided to aid the understanding and are not limited to these.
상기 화학식 6에 있어서, n 및 m은 각각 독립적으로 0 또는 양의 정수이고, R 및 R'는 각각 독립적으로 알킬기, 알콕시기, 아세틸기, 이민기, 에테르기, 에스터기, 니트릴기, 티오알콕시기, 아미노기, 티오에스터기 비닐기, 아릴기, 헤테로기 등으로 이루어진 군으로부터 선택된 어느 하나이다. 바람직하게, n 및 m은 0 내지 10이다.In Formula 6, n and m are each independently 0 or a positive integer, and R and R 'are each independently an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group , Amino group, thioester group vinyl group, aryl group, hetero group and any one selected from the group consisting of. Preferably, n and m are 0 to 10.
상기 화학식 7에 있어서, n 및 n'는 각각 독립적으로 0 또는 양의 정수이고, m은 양의 정수이며, R 및 R'는 각각 독립적으로 알킬기, 알콕시기, 아세틸기, 이민기, 에테르기, 에스터기, 니트릴기, 티오알콕시기, 아미노기, 티오에스터기, 비닐 기, 아릴기, 헤테로기 등으로 이루어진 군으로부터 선택된 어느 하나이다. 바람직하게, n 및 n'는 각각 독립적으로 0 내지 10 이고, m은 1 내지 100이다.In 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 an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester Group, nitrile group, thioalkoxy group, amino group, thioester group, vinyl group, aryl group, hetero group and the like. Preferably, n and n 'are each independently 0 to 10 and m is 1 to 100.
상기 화학식 8에 있어서, n은 각각 독립적으로 0 또는 양의 정수이고, R1 내지 R18은 각각 독립적으로 알킬기, 알콕시기, 아세틸기, 트리알킬실릴아세틸기, 에테르기, 아미노기, 이민기, 에스터기, 니트릴기, 티오알콕시기, 티오에스터기, 비닐기, 아릴기, 헤테로기 등으로 이루어진 군으로부터 선택된 어느 하나이다. 바람직하게, n 및 m은 각각 독립적으로 0 내지 3이다.In Formula 8, n is each independently 0 or a positive integer, and R1 to R18 are each independently an alkyl group, an alkoxy group, an acetyl group, a trialkylsilylacetyl group, an ether group, an amino group, an imine group, an ester group, a nitrile Any one selected from the group consisting of a group, a thioalkoxy group, a thioester group, a vinyl group, an aryl group, a hetero group, and the like. Preferably, n and m are each independently 0-3.
상기 화학식 9에 있어서, n 및 m은 각각 독립적으로 0 또는 양의 정수이고, R 및 R'는 각각 독립적으로 알킬기, 알콕시기, 아세틸기, 이민기, 에테르기, 에스터기, 니트릴기, 티오알콕시기, 아미노기, 티오에스터기, 비닐기, 아릴기, 헤테로기 등으로 이루어진 군으로부터 선택된 어느 하나이다. 바람직하게, n 및 m은 각각 독립적으로 0 내지 10이다.In Formula 9, n and m are each independently 0 or a positive integer, and R and R 'are each independently 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 and the like. Preferably, n and m are each independently 0-10.
상기 화학식 10에 있어서, n 및 m은 각각 독립적으로 0 또는 양의 정수이고, R1 내지 R18은 각각 독립적으로 알킬기, 알콕시기, 아세틸기, 트리알킬실릴아세틸기, 이민기, 에테르기, 에스터기, 니트릴기, 티오알콕시기, 아미노기, 티오에스터기, 비닐기, 아릴기, 헤테로기 등으로 이루어진 군으로부터 선택된 어느 하나이다. 바람직하게, n 및 m은 각각 독립적으로 0 내지 3이다.In Formula 10, n and m are each independently 0 or a positive integer, R1 to R18 are each independently an alkyl group, an alkoxy group, an acetyl group, a trialkylsilylacetyl group, an imine group, an ether group, an ester group, a nitrile It is any one selected from the group consisting of a group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, a hetero group, and the like. Preferably, n and m are each independently 0-3.
상기 화학식 11에 있어서, n은 0 또는 양의 정수이다. 바람직하게, n은 0 내지 10이다.In Formula 11, n is 0 or a positive integer. Preferably, n is 0 to 10.
상기 화학식 12에 있어서, n은 0 또는 양의 정수이고, R1 내지 R8은 각각 독립적으로 알킬기, 알콕시기, 아세틸기, 트리알킬실릴아세틸기, 이민기, 에테르기, 에스터기, 니트릴기, 티오알콕시기, 아미노기, 티오에스터기, 비닐기, 아릴기, 헤테로기 등으로 이루어진 군으로부터 선택된 어느 하나이다. 바람직하게, n은 0 내지 3이다.In Formula 12, n is 0 or a positive integer, and R1 to R8 are each independently an alkyl group, an alkoxy group, an acetyl group, a trialkylsilylacetyl group, an imine group, an ether group, an ester group, a nitrile group, or a thioalkoxy group , An amino group, a thioester group, a vinyl group, an aryl group, a hetero group and the like. Preferably, n is 0-3.
상기 화학식 13에 있어서, n 은 0 또는 양의 정수이고, m은 양의 정수이고, R1 내지 R8은 각각 독립적으로 알킬기, 알콕시기, 아세틸기, 트리알킬실릴아세틸기, 이민기, 에테르기, 에스터기, 니트릴기, 티오알콕시기, 아미노기, 티오에스터기, 비닐기, 아릴기, 헤테로기 등으로 이루어진 군으로부터 선택된 어느 하나이다. 바람직하게, n은 0 내지 3이고, m은 1 내지 100이다.In Formula 13, n is 0 or a positive integer, m is a positive integer, R1 to R8 are each independently an alkyl group, an alkoxy group, an acetyl group, a trialkylsilylacetyl group, an imine group, an ether group, an ester group , Nitrile group, thioalkoxy group, amino group, thioester group, vinyl group, aryl group, hetero group and the like. Preferably, n is 0-3 and m is 1-100.
상기 화학식 14에 있어서, n 및 m은 각각 독립적으로 0 또는 양의 정수이고, R 및 R'는 각각 독립적으로 알킬기, 알콕시기, 아세틸기, 이민기, 에스터기, 에테르기, 니트릴기, 티오알콕시기, 아미노기, 티오에스터기, 비닐기, 아릴기, 헤테로기 등으로 이루어진 군으로부터 선택된 어느 하나이다. 바람직하게, n 및 m은 0 내지 10이다.In Formula 14, n and m are each independently 0 or a positive integer, and R and R 'are each independently 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, a hetero group and the like. Preferably, n and m are 0 to 10.
상기 화학식 15에 있어서, n 및 m은 각각 독립적으로 0 또는 양의 정수이고, R1 내지 R18은 각각 독립적으로 알킬기, 알콕시기, 아세틸기, 트리알킬실릴아세틸기, 이민기, 에테르기, 에스터기, 니트릴기, 티오알콕시기, 아미노기, 티오에스터기, 비닐기, 아릴기, 헤테로기 등으로 이루어진 군으로부터 선택된 어느 하나이다. 바람직하게, n 및 m은 각각 독립적으로 0 내지 3이다.In Formula 15, n and m are each independently 0 or a positive integer, R1 to R18 are each independently an alkyl group, an alkoxy group, an acetyl group, a trialkylsilylacetyl group, an imine group, an ether group, an ester group, a nitrile It is any one selected from the group consisting of a group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, a hetero group, and the like. Preferably, n and m are each independently 0-3.
상기 화학식 16에서, R 및 R'는 각각 독립적으로 수소원자, 탄소수 1~20의 알킬기, 탄소수 1~20의 알콕시기, 티오알콕시기, 니트릴기, 니트로기, 에스터기, 에테르기, 이미드기, 아미드기, 티오에스터기, 아릴기, 헤테로 아릴기 등에서 선택되는 어느 하나이고, A 는 연결기로서 탄소수 1~20의 알킬기, 탄소수 1~20의 에테르기, 티오에테르기, 아릴기, 헤테로 아릴기, 비닐기, 아세틸기 등에서 선택되는 어느 하나이다. n은 양의 정수이고 바람직하게는 1 내지 10 이며, l 과 m은 각각 독립적으로 0 또는 양의 정수이고 바람직하게 0 내지 10 이며, k는 양의 정수이고 바람직하게는 1 내지 100 이다. In Formula 16, R and R 'are each independently 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, a heteroaryl group, and the like, and A is 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 heteroaryl group, It is either selected from a vinyl group, an acetyl group, etc. n is a positive integer and preferably 1 to 10, l and m are each independently 0 or a positive integer and preferably 0 to 10, k is a positive integer and preferably 1 to 100.
상기 화학식 6 내지 16으로 표시된 화합물은 단량체 화합물뿐만 아니라 고분자 화합물을 형성할 수도 있다.The compounds represented by Chemical Formulas 6 to 16 may form a polymer compound as well as a monomer compound.
또한, 상기 화합물들에서 티오펜계 유도체나 아센계 유도체는 알킬기, 알콕시기, 아세틸기, 이민기, 에테르기, 에스터기, 니트릴기, 티오알콕시기, 아미노기, 티오에스터기, 비닐기, 아릴기, 헤테로기 등으로 치환될 수 있다.In the above compounds, the thiophene derivative or the acene derivative may be 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, It may be substituted with a hetero group or the like.
본 발명에 따른 유기 박막 트랜지스터는 유기 반도체층을 전술한 재료 및 방법으로 제작하는 것을 제외하고는 당 기술 분야에 알려진 재료, 구조 및 방법으로 제작 될 수 있다. 본 발명에 따른 OTFT는 유기 반도체층 이외에 게이트 전극, 게이트 절연막, 소스 전극 및 드레인 전극을 포함한다. 또한, 상기 유기 박막 트랜지스터는 게이트 전극의 하부에 기판을 추가로 포함할 수 있다. The organic thin film transistor according to the present invention may be manufactured by materials, structures, and methods known in the art, except that the organic semiconductor layer is manufactured by the aforementioned materials and methods. The OTFT according to the present invention includes a gate electrode, a gate insulating film, a source electrode and a drain electrode in addition to the organic semiconductor layer. In addition, the organic thin film transistor may further include a substrate under the gate electrode.
도 1 및 도 2는 본 발명에 따른 유기 박막 트랜지스터의 구조를 예시한 것이다. 그러나, 도 1의 유기 박막 트랜지스터는 하나의 예시이며, 본 발명의 목적을 해치지 않는 범위에서 본 발명의 유기 박막 트랜지스터는 다양한 구조를 가질 수 있다. 1 and 2 illustrate the structure of an organic thin film transistor according to the present invention. However, the organic thin film transistor of FIG. 1 is one example, and the organic thin film transistor of the present invention may have various structures within a range that does not impair the object of the present invention.
기판으로는 플라스틱, 종이 등과 같은 플렉시블한 재료를 사용할 수도 있고, 실리콘, 유리 등과 같은 무기 재료를 사용할 수 있으나 이에 한정되지는 않는다.As the substrate, a flexible material such as plastic or paper may be used, and an inorganic material such as silicon or glass may be used, but is not limited thereto.
게이트 전극은 도전성 물질을 사용할 수 있는데, 그러한 도전성 물질의 비제한적인 예로는 탄소, 알루미늄, 바나듐, 크롬, 구리, 아연, 은, 금, 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 주석, 납, 금속 유사물(similar metals) 및 상기 금속의 합금, p- 또는 n- 도프된(doped) 실리콘, 산화아연, 산화 인듐, 인듐 주석 산화물(ITO), 인듐 아연 산화물 및 주석 유사 산화물(similar tin oxide) 또는 주석 산화물 인듐계 복합 화합물(tin oxide indium-based complex compounds), ZnO:Al, SnO2:Sb 와 같은 산화물과 금속의 혼합물, 폴리(3-메틸티오펜)(poly(3-methylthiophene)), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜] (poly[3,4-(ethylene-1,2-dioxy) thiophene]), 폴리피롤(polypyrrole) 및 폴리아닐린(polyaniline)과 같은 도전성 고분자를 포함한다.The gate electrode may use a conductive material, and non-limiting examples of such conductive material include carbon, aluminum, vanadium, chromium, copper, zinc, silver, gold, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium , Gadolinium, tin, lead, metals and alloys of these metals, p- or n-doped silicon, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide and tin Pseudo tin oxide or tin oxide indium-based complex compounds, mixtures of oxides and metals such as ZnO: Al, SnO 2 : Sb, poly (3-methylthiophene) (3-methylthiophene)), poly [3,4- (ethylene-1,2-dioxy) thiophene] (poly [3,4- (ethylene-1,2-dioxy) thiophene]), polypyrrole And conductive polymers such as polyaniline.
게이트 절연막은 절연 물질을 사용할 수 있는데, 비제한적인 예로는 실리콘 산화물, 실리콘 질화물, 및 폴리이미드, 폴리(2-비닐피리딘), 폴리(4-비닐페놀), 폴리메틸 메타크릴레이트와 같은 플라스틱 절연체를 포함한다.The gate insulating film may use an insulating material, including, but not limited to, silicon oxide, silicon nitride, and plastic insulator such as polyimide, poly (2-vinylpyridine), poly (4-vinylphenol), polymethyl methacrylate, and the like. It includes.
소스, 드레인 및 게이트 전극으로는 금(Au), 백금(Pt), 은(Ag), 팔라듐(Pd), 알루미늄(Al), 니켈(Ni), 크롬(Cr) 등의 일반적으로 사용되는 금속, 또는 인듐주석산화물(indium tin oxide), 인듐아연산화물(indium zinc oxide), 니켈산화물(nickel oxide) 등의 전도성 금속 산화물, 또는 폴리아닐린(polyaniline), 폴리피롤(polypyrrole), 폴리에틸렌디옥시티오펜(polyethylenedioxythiophene) 등의 전도성 고분자 등을 사용할 수 있으나, 이들 예에만 한정되는 것은 아니다.As the source, drain, and gate electrodes, commonly used metals such as gold (Au), platinum (Pt), silver (Ag), palladium (Pd), aluminum (Al), nickel (Ni), chromium (Cr), Or conductive metal oxides such as indium tin oxide, indium zinc oxide, and nickel oxide, or polyaniline, polypyrrole, polyethylenedioxythiophene, or the like. Conductive polymers may be used, but the present invention is not limited thereto.
또한, 본 발명은 상기 유기 박막 트랜지스터를 포함하는 전자장치를 제공한다. 상기 전자장치에는 전자 종이, 스마트 카드, 메모리 소자, 디스플레이 장치 등이 있다.In addition, the present invention provides an electronic device including the organic thin film transistor. The electronic device includes an electronic paper, a smart card, a memory device, a display device, and the like.
이하, 본 발명의 실시예를 통해 본 발명에 대해 상세히 설명한다. 그러나, 본 발명의 실시예들은 여러 가지 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 상술하는 실시예들로 인하여 한정되는 식으로 해석되어서는 안된다. 본 발명의 실시예들은 본 발명을 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, the present invention will be described in detail through embodiments of the present invention. However, embodiments of the present invention may be modified in various forms, the scope of the present invention should not be construed in a way that is limited by the embodiments described below. Embodiments of the present invention are provided to more fully illustrate the present invention.
<제조예 1> 상기 화학식 4로 표시되는 화합물의 합성Preparation Example 1 Synthesis of Compound Represented by Formula 4
질소 분위기 하에서 퀴나크리돈(quinacridone, 2.388g, 7.65mmol)과 4-디메틸아미노-피리딘(4-dimethylamino-pyridine, 0.476g, 3.90mmol, 0.51eq)을 무수 THF(77ml)에 넣은 후, 상온에서 디-터트-부틸디카르보네이트(di-tert-butyldicarbonate, 4.174g, 19.13mmol, 2.5eq)를 1시간 동안 3번 나누어 첨가하였다. 하루 동안 저어준 후 용매를 감압 하에 증발시키고 5% 중탄산나트륨(sodium bicarbonate) 수용액과 증류수로 씻어주었다. 불순물을 CH2Cl2 용매로 컬럼 분리하여 노란색 분말의 상기 화학식 4로 표시되는 화합물을 얻었다. GC/MS: [M+H]+=513In a nitrogen atmosphere, quinacridone (2.388g, 7.65mmol) and 4-dimethylamino-pyridine (4-dimethylamino-pyridine, 0.476g, 3.90mmol, 0.51eq) were added to dry THF (77ml), and then at room temperature. Di-tert-butyldicarbonate (4.174 g, 19.13 mmol, 2.5 eq) was added in three portions for 1 hour. After stirring for one day, the solvent was evaporated under reduced pressure and washed with 5% sodium bicarbonate aqueous solution and distilled water. Impurities were column separated with a solvent of CH 2 Cl 2 to obtain a compound represented by Chemical Formula 4 as a yellow powder. GC / MS: [M + H] + = 513
이 물질에 대한 열분석(TGA)결과를 나타낸 도 6을 참조하면, 수소결합을 제한하는 치환체는 열에 의해, 특히 200 ℃ 이하에서 제거됨을 알 수 있다.Referring to FIG. 6, which shows the results of thermal analysis (TGA) for this material, it can be seen that substituents that limit hydrogen bonding are removed by heat, in particular below 200 ° C.
<실험예 1> 진공 증착에 의한 유기 박막 트랜지스터의 제작Experimental Example 1 Fabrication of Organic Thin Film Transistor by Vacuum Vapor Deposition
n-타입 도핑된 저저항 실리콘 웨이퍼를 게이트 전극으로 사용하고, 그 위에 열산화법을 이용하여 SiO2를 3000Å 두께인 게이트 절연막으로 적층하였다. 다음으로 채널 길이 10㎛, 채널 폭 300㎛인 소스-드레인 전극을 포토리소그래피 공정으로 금을 500Å 두께로 형성하였다. 제조된 기판은 UV-오존 플라즈마로 표면 처리하고 그 위에 HMDS(hexamethyldisilazane)를 30초 동안 3000rpm으로 스핀 코팅한 후, 120℃에서 2분간 베이킹 하였다. 그 위에 화학식 1로 표시되는 퀴나크리돈을 0.3Å/s의 속도로 진공 증착하여 두께 500Å의 채널 물질을 형성하였다.An n-type doped low-resistance silicon wafer was used as a gate electrode, and SiO 2 was laminated thereon with a gate insulating film having a thickness of 3000 Å by thermal oxidation. Next, a source-drain electrode having a channel length of 10 μm and a channel width of 300 μm was formed to have a thickness of 500 μm by a photolithography process. The prepared substrate was surface-treated with UV-ozone plasma, spin-coated HMDS (hexamethyldisilazane) at 3000 rpm for 30 seconds, and then baked at 120 ° C. for 2 minutes. Quinacridone represented by
이와 같이 제조된 유기 박막 트랜지스터는 7.94 × 10-5 ㎠/Vs의 전계 효과 이동도를 나타내었다. 이를 도 3에 나타내었다. The organic thin film transistor thus manufactured exhibited a field effect mobility of 7.94 × 10 −5 cm 2 / Vs. This is shown in FIG. 3.
화학식 1로 표시되는 퀴나크리돈은 비교적 큰 밴드갭을 가짐에도 불구하고 상기와 같은 전계효과를 나타내는 것으로부터 이들이 수소결합에 의해 분자간 작용이 큰 박막을 형성함을 알 수 있었다.Although quinacridone represented by the formula (1) has a relatively large band gap, the quinacridone exhibited the above electric field effect, and it was found that they form a thin film having a large intermolecular action by hydrogen bonding.
<실험예 2> 용액 공정에 의한 유기 박막 트랜지스터의 제작 Experimental Example 2 Fabrication of Organic Thin Film Transistor by Solution Process
n-타입 도핑된 저저항 실리콘 웨이퍼를 게이트 전극으로 사용하고 그 위에 열산화법을 이용하여 SiO2를 3000Å 두께인 게이트 절연막으로 적층하였다. 다음으로 채널 길이 10㎛, 채널 폭 300㎛인 소스-드레인 전극을 포토리소그래피 공정으로 금을 500Å 두께로 증착하였다. 제조된 기판은 UV-오존 플라즈마로 표면 처리하고 그 위에 HMDS(hexamethyldisilazane)를 30초 동안 3000rpm으로 스핀 코팅한 후, 120℃에서 2분간 베이킹 하였다. 그 위에 상기 제조예 1에 따라 제조된 화학식 4로 표시되는 화합물을 테트라클로로에탄(tetrachloroethane)에 2w/w% 농도로 녹여 제조한 용액을 1500rpm에서 20초동안 스핀 코팅하고 50 ℃에서 1분, 180 ℃에서 2분동안 건조하여 유기 박막 트랜지스터를 제조하였다. An n-type doped low-resistance silicon wafer was used as the gate electrode, and SiO 2 was deposited thereon by a gate insulating film having a thickness of 3000 Å by thermal oxidation. Next, a source-drain electrode having a channel length of 10 μm and a channel width of 300 μm was deposited with a thickness of 500 μm by a photolithography process. The prepared substrate was surface-treated with UV-ozone plasma, spin-coated HMDS (hexamethyldisilazane) at 3000 rpm for 30 seconds, and then baked at 120 ° C. for 2 minutes. A solution prepared by dissolving the compound represented by Chemical Formula 4 prepared according to Preparation Example 1 at a concentration of 2w / w% in tetrachloroethane was spin-coated at 1500 rpm for 20 seconds, followed by spinning at 50 ° C. for 1 minute, 180 Drying at 2 ° C. for 2 minutes yielded an organic thin film transistor.
상기와 같이 제조된 유기 박막 트랜지스터는 1.84 × 10-5 cm2/Vs의 전계 효과 이동도를 나타내었다. 이를 도 4에 나타내었다. The organic thin film transistor manufactured as described above exhibited a field effect mobility of 1.84 × 10 −5 cm 2 / Vs. This is shown in FIG. 4.
또한, 상기와 같은 열처리에 의해 치환체가 제거되고 수소 결합을 하는 물질이 재형성 되는지를 확인하기 위하여, 제조예 1에 따라 제조된 용액으로부터 유리기판 위에 박막을 제조하였을 때(점선)와 이를 실험예 2와 같은 방법으로 열처리하여 얻어진 박막(실선)의 흡수 스펙트럼을 측정하여 도 5에 나타내었다. 이 흡수 스 펙트럼으로부터 열처리에 의해 치환체가 제거되고 화학식 1의 화합물이 다시 생성되는 것을 알 수 있다.In addition, when the thin film was prepared on the glass substrate from the solution prepared according to Preparation Example 1 (dotted line) to confirm whether the substituent is removed and the hydrogen bonding material is reformed by the heat treatment as described above and the experimental example The absorption spectrum of the thin film (solid line) obtained by heat treatment in the same manner as in Example 2 was measured and shown in FIG. 5. It can be seen from this absorption spectrum that the substituents are removed by heat treatment and the compound of
상기와 같이 용액 공정에 의해 형성된 유기 반도체막으로부터 얻어진 유기 박막 트랜지스터의 특성이 진공 증착에 의해 형성된 반도체 막으로부터 얻어진 유기 박막 트랜지스터의 특성에 비해 상대적으로 낮은 전계효과이동도를 나타내었으나 그 차이가 크지 않은 것으로부터 상기와 같은 수소결합을 재형성함에 의한 유기 박막 트랜지스터의 제조방법이 유효함을 알 수 있다. As described above, the characteristics of the organic thin film transistor obtained from the organic semiconductor film formed by the solution process showed relatively low field effect mobility compared to the characteristics of the organic thin film transistor obtained from the semiconductor film formed by vacuum deposition. It can be seen from this that the method for producing an organic thin film transistor by reforming the hydrogen bond as described above is effective.
본 발명에 따른 유기 박막 트랜지스터의 제조방법은 용액 공정이 가능하면서, 최종적으로는 수소결합으로 인하여 강한 결합력을 갖는 결정성이 우수한 유기 반도체층을 형성할 수 있다. 따라서, 이를 이용한 높은 전계 효과 이동도를 갖는 유기 박막 트랜지스터를 제조할 수 있다.The method of manufacturing an organic thin film transistor according to the present invention can perform a solution process, and finally can form an organic semiconductor layer excellent in crystallinity having strong bonding force due to hydrogen bonding. Therefore, an organic thin film transistor having high field effect mobility using the same can be manufactured.
Claims (30)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020060070933A KR100918362B1 (en) | 2006-07-27 | 2006-07-27 | Organic tfts and method for fabricating the same |
| PCT/KR2007/003630 WO2008013427A1 (en) | 2006-07-27 | 2007-07-27 | Organic tfts and method for fabricating the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020060070933A KR100918362B1 (en) | 2006-07-27 | 2006-07-27 | Organic tfts and method for fabricating the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20080010644A KR20080010644A (en) | 2008-01-31 |
| KR100918362B1 true KR100918362B1 (en) | 2009-09-22 |
Family
ID=38981703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020060070933A KR100918362B1 (en) | 2006-07-27 | 2006-07-27 | Organic tfts and method for fabricating the same |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR100918362B1 (en) |
| WO (1) | WO2008013427A1 (en) |
Families Citing this family (5)
| 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 |
| US8877546B2 (en) * | 2010-05-28 | 2014-11-04 | Corning Incorporated | Enhanced semiconductor devices employing photoactive organic materials and methods of manufacturing same |
| JP5921554B2 (en) * | 2010-09-29 | 2016-05-24 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Diketopyrrolopyrrole semiconductor |
| US8946376B2 (en) | 2010-09-29 | 2015-02-03 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
| JP5807738B2 (en) * | 2011-03-30 | 2015-11-10 | ソニー株式会社 | Organic transistor manufacturing method, organic transistor, semiconductor device manufacturing method, semiconductor device, and electronic apparatus |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0794807A (en) * | 1993-07-27 | 1995-04-07 | Toshiba Corp | Amorphous organic thin film element, amorphous organic polymer compound and amorphous inorganic compound |
| JP2005085945A (en) | 2003-09-08 | 2005-03-31 | Canon Inc | Field effect type organic transistor and its manufacturing method |
| KR20060080238A (en) * | 2003-10-30 | 2006-07-07 | 마츠시타 덴끼 산교 가부시키가이샤 | Conductive thin film and thin-film transistor |
| KR20070117138A (en) * | 2006-06-07 | 2007-12-12 | 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2347013A (en) * | 1999-02-16 | 2000-08-23 | Sharp Kk | Charge-transport structures |
| US6777565B2 (en) * | 2000-06-29 | 2004-08-17 | Board Of Trustees, The University Of Illinois | Organometallic compounds and their use as precursors for forming films and powders of metal or metal derivatives |
| US6890868B2 (en) * | 2002-10-17 | 2005-05-10 | Xerox Corporation | Process for depositing gelable composition that includes dissolving gelable composition in liquid with agitating to disrupt gelling |
-
2006
- 2006-07-27 KR KR1020060070933A patent/KR100918362B1/en not_active IP Right Cessation
-
2007
- 2007-07-27 WO PCT/KR2007/003630 patent/WO2008013427A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0794807A (en) * | 1993-07-27 | 1995-04-07 | Toshiba Corp | Amorphous organic thin film element, amorphous organic polymer compound and amorphous inorganic compound |
| JP2005085945A (en) | 2003-09-08 | 2005-03-31 | Canon Inc | Field effect type organic transistor and its manufacturing method |
| KR20060080238A (en) * | 2003-10-30 | 2006-07-07 | 마츠시타 덴끼 산교 가부시키가이샤 | Conductive thin film and thin-film transistor |
| KR20070117138A (en) * | 2006-06-07 | 2007-12-12 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20080010644A (en) | 2008-01-31 |
| WO2008013427A1 (en) | 2008-01-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100918362B1 (en) | Organic tfts and method for fabricating the same | |
| KR101096981B1 (en) | New fused ring compound and organic electronic device using the same | |
| JP5202545B2 (en) | Organic transistor using thiazolothiazole derivative and method for producing the same | |
| JP5160078B2 (en) | Field effect transistor | |
| JP5335228B2 (en) | NOVEL COMPOUND AND METHOD FOR PRODUCING ORGANIC SEMICONDUCTOR DEVICE | |
| JP2004266157A (en) | Organic field-effect transistor and method for manufacturing the same | |
| JP2006206503A (en) | pi ELECTRON-BASED COMPOUND AND n-TYPE ORGANIC FIELD-EFFECT TRANSISTOR GIVEN BY USING THE SAME | |
| JP5569774B2 (en) | Tetrathiafulvalene derivative | |
| US7692021B2 (en) | NPN-type low molecular aromatic ring compounds and organic semiconductors and electronic devices incorporating such compounds | |
| Iyoda | Fully conjugated macrocycles composed of thiophenes, acetylenes, and ethylenes | |
| CN104641471A (en) | Coating materials for oxide thin film transistors | |
| WO2012070582A1 (en) | Conjugated compound, and organic thin film and organic thin film element using same | |
| JP2007042717A (en) | Tetrathiafulvalene derivative, tetraselenafulvalene derivative, and p-type organic field-effect transistor | |
| JP5426199B2 (en) | Branched compound, organic thin film and organic thin film element using the same | |
| JPWO2010098326A1 (en) | NOVEL COMPOUND, PROCESS FOR PRODUCING THE SAME, ORGANIC SEMICONDUCTOR MATERIAL AND ORGANIC SEMICONDUCTOR DEVICE | |
| KR100868863B1 (en) | New fused ring compound and organic electronic device using the same | |
| WO2015133471A1 (en) | Compound, polymer produced by polymerizing said compound, and organic semiconductor material and use thereof | |
| JP5438326B2 (en) | An organic transistor using an organic semiconductor material made of a compound having a thienothiophene skeleton for a semiconductor layer. | |
| CN110690347A (en) | Application of porphyrin material in organic storage | |
| CN110526923A (en) | A kind of Porphyrin Molecule of side chain modification and its application | |
| JP5196755B2 (en) | device | |
| JP5392706B2 (en) | Organic semiconductor material and organic thin film transistor | |
| JP4401836B2 (en) | Field effect transistor and manufacturing method thereof | |
| JP4878105B2 (en) | Method for manufacturing field effect transistor | |
| JP5578414B2 (en) | Organic transistor using tetrathiafulvalene derivative and method for producing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E90F | Notification of reason for final refusal | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20120710 Year of fee payment: 4 |
|
| LAPS | Lapse due to unpaid annual fee |