KR101052356B1 - 유기절연막 및 이를 포함하는 유기박막트랜지스터 - Google Patents
유기절연막 및 이를 포함하는 유기박막트랜지스터 Download PDFInfo
- Publication number
- KR101052356B1 KR101052356B1 KR1020090032733A KR20090032733A KR101052356B1 KR 101052356 B1 KR101052356 B1 KR 101052356B1 KR 1020090032733 A KR1020090032733 A KR 1020090032733A KR 20090032733 A KR20090032733 A KR 20090032733A KR 101052356 B1 KR101052356 B1 KR 101052356B1
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- South Korea
- Prior art keywords
- organic
- thin film
- film transistor
- polyimide
- formula
- Prior art date
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- 239000010409 thin film Substances 0.000 title claims abstract description 102
- 239000010408 film Substances 0.000 title claims description 24
- 229920001721 polyimide Polymers 0.000 claims abstract description 50
- 239000004642 Polyimide Substances 0.000 claims abstract description 48
- 238000000016 photochemical curing Methods 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000000126 substance Substances 0.000 claims description 28
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 21
- -1 polyphenylenevinylene Polymers 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 239000010410 layer Substances 0.000 claims description 10
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000004528 spin coating Methods 0.000 claims description 7
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000007598 dipping method Methods 0.000 claims description 3
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- 239000002184 metal Substances 0.000 claims description 3
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- 230000015572 biosynthetic process Effects 0.000 claims description 2
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- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 claims description 2
- 229920000123 polythiophene Polymers 0.000 claims description 2
- 239000011241 protective layer Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000012212 insulator Substances 0.000 abstract description 56
- 229920000642 polymer Polymers 0.000 abstract description 42
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- 230000008569 process Effects 0.000 abstract description 19
- 239000003960 organic solvent Substances 0.000 abstract description 17
- 238000001723 curing Methods 0.000 abstract description 15
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- 230000000052 comparative effect Effects 0.000 description 11
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 10
- 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 10
- OHLQBRYVKXJYHZ-UHFFFAOYSA-N (3,5-diaminophenyl)methanol Chemical compound NC1=CC(N)=CC(CO)=C1 OHLQBRYVKXJYHZ-UHFFFAOYSA-N 0.000 description 9
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 9
- 239000013557 residual solvent Substances 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
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- 239000004372 Polyvinyl alcohol Substances 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 description 8
- 239000001518 benzyl (E)-3-phenylprop-2-enoate Substances 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- GPHYIQCSMDYRGJ-UHFFFAOYSA-N (3,5-dinitrophenyl)methanol Chemical compound OCC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 GPHYIQCSMDYRGJ-UHFFFAOYSA-N 0.000 description 6
- IDXLMUPIWAJBRO-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-3-methylcyclohexane-1,2-dicarboxylic acid Chemical compound C1C(C(O)=O)C(C(O)=O)C(C)CC1C1C(=O)OC(=O)C1 IDXLMUPIWAJBRO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- NGHOLYJTSCBCGC-UHFFFAOYSA-N cis-cinnamic acid benzyl ester Natural products C=1C=CC=CC=1C=CC(=O)OCC1=CC=CC=C1 NGHOLYJTSCBCGC-UHFFFAOYSA-N 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- FIELFBYURBDLHU-UHFFFAOYSA-N tert-butyl n-[3-(hydroxymethyl)-5-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(CO)=CC(NC(=O)OC(C)(C)C)=C1 FIELFBYURBDLHU-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000004695 Polyether sulfone Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
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- 239000010703 silicon Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000003746 surface roughness Effects 0.000 description 3
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004630 atomic force microscopy Methods 0.000 description 2
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- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
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- 125000006159 dianhydride group Chemical class 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
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- XLPYYBNLEUOIMD-UHFFFAOYSA-N (2-carbamoyloxyphenyl) carbamate Chemical compound NC(=O)OC1=CC=CC=C1OC(N)=O XLPYYBNLEUOIMD-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- GYFUIPAIOWWVFV-UHFFFAOYSA-N 1-phenoxycyclohexa-3,5-diene-1,3-diamine Chemical compound C1C(N)=CC=CC1(N)OC1=CC=CC=C1 GYFUIPAIOWWVFV-UHFFFAOYSA-N 0.000 description 1
- PHVRZIZNMSHECZ-UHFFFAOYSA-N 3-(4-phenylphenyl)prop-2-enoyl chloride Chemical compound C1=CC(C=CC(=O)Cl)=CC=C1C1=CC=CC=C1 PHVRZIZNMSHECZ-UHFFFAOYSA-N 0.000 description 1
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- OPIGLBSXOOGSLX-UHFFFAOYSA-N 3-naphthalen-1-ylprop-2-enoyl chloride Chemical compound C1=CC=C2C(C=CC(=O)Cl)=CC=CC2=C1 OPIGLBSXOOGSLX-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- NYQBRJSZBZNLAM-UHFFFAOYSA-N 4-phenoxycyclohexa-1,5-diene-1,4-diamine Chemical compound C1=CC(N)=CCC1(N)OC1=CC=CC=C1 NYQBRJSZBZNLAM-UHFFFAOYSA-N 0.000 description 1
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- GGDKNFCCHJCIIO-UHFFFAOYSA-N 6-(1-phenylpropoxy)cyclohexa-2,4-diene-1,1-diamine Chemical compound C=1C=CC=CC=1C(CC)OC1C=CC=CC1(N)N GGDKNFCCHJCIIO-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- 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]
- H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
- H10K10/471—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising only organic materials
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Abstract
Description
Claims (19)
- 하기 화학식 1, 화학식 2 및 화학식 3으로부터 선택되는 하나의 폴리이미드의 광 경화막인 유기절연막.[화학식 1][화학식 2][화학식 3]q는 0 내지 10의 정수이며; X1, X2, X3, X4 및 X5는 서로 독립적으로 수소, C1-C10의 알킬, 시아노 또는 할로겐 치환체이며;m, n 및 l의 합은 10 내지 3,000(m은 0을 포함)의 정수이다.
- 제 1 항에 있어서,상기 폴리이미드의 질량평균 분자량이 5,000 내지 1,000,000 g/mol의 범위를 갖는 유기절연막.
- 제 1 항에 있어서,상기 폴리이미드의 고유점도가 0.1 내지 1.5 dL/g 의 범위를 갖는 유기절연막.
- 제 1 항에 있어서,상기 폴리이미드의 절연 박막 형성 온도가 100 내지 300℃ 인 유기절연막.
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- 기판 상부에 게이트 전극, 유기절연막, 유기활성층, 소스/드레인 전극 및 보호층으로 구성된 유기박막트랜지스터에 있어서, 상기 유기절연막은 제 1 항 내지 제 4 항에서 선택되는 어느 한 항의 것으로 하는 유기박막트랜지스터.
- 제 14 항에 있어서,상기 유기절연막은 폴리이미드를 스핀코팅법, 잉크젯 프린팅법 및 딥핑법으로 이루어진 군으로부터 선택되는 방법에 의해 도포하고, 광 경화시키는 단계를 포함하여 형성된 것인 유기박막트랜지스터.
- 제 14 항에 있어서,상기 유기절연막의 두께는 30 내지 900 nm 범위로 형성하는 유기박막트랜지스터.
- 제 14 항에 있어서,상기 유기활성층은 펜타센, 금속 프탈로시아닌, 폴리티오펜, 폴리페닐렌비닐렌, C60, 페닐렌테트라카르복실산2무수물, 나프탈렌테투라카르복실산2무수물, 플루오르화 프탈로시아닌 및 이들의 유도체로 이루어진 군으로부터 선택되는 유기박막트랜지스터.
- 제 14 항에 있어서,유기박막트랜지스터의 전계이동도가 0.01 내지 10 ㎠/Vs의 범위인 유기박막트랜지스터.
- 제 14 항 내지 제 1 8 항에서 선택된 어느 한 항의 유기박막트랜지스터를 이용한 표시 소자.
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KR101372870B1 (ko) * | 2012-12-12 | 2014-03-12 | 한국화학연구원 | 광경화성 폴리이미드를 이용한 전극의 패터닝 방법 및 이를 통해 제조된 패턴 |
KR101446712B1 (ko) * | 2013-03-26 | 2014-10-07 | 한국화학연구원 | 고내열 폴리이미드 화합물, 이를 포함하는 유기절연체 조성물 및 이를 이용한 박막트랜지스터 |
KR102641038B1 (ko) | 2016-09-30 | 2024-02-27 | 티씨엘 차이나 스타 옵토일렉트로닉스 테크놀로지 컴퍼니 리미티드 | 표시 장치 및 표시 장치의 제조방법 |
KR102104801B1 (ko) * | 2017-11-14 | 2020-04-28 | 한국화학연구원 | 폴리이미드 중합체 및 이를 포함하는 광전 소자 |
KR102133942B1 (ko) * | 2019-01-21 | 2020-07-22 | 한국화학연구원 | 반응성 단량체를 함유하는 광전 기능 폴리이미드 중합체 조성물 및 이를 포함하는 광전 소자 |
CN113484386B (zh) * | 2021-05-21 | 2024-02-13 | 郑州轻工业大学 | 一种金属聚酞菁纳米材料的制备方法及其应用,适配体传感器及其制备方法 |
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