KR100491944B1 - 이미드 고리 함유 측쇄기를 갖는 액정배향막용 폴리아믹산유도체 - Google Patents
이미드 고리 함유 측쇄기를 갖는 액정배향막용 폴리아믹산유도체 Download PDFInfo
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- KR100491944B1 KR100491944B1 KR10-2002-0077802A KR20020077802A KR100491944B1 KR 100491944 B1 KR100491944 B1 KR 100491944B1 KR 20020077802 A KR20020077802 A KR 20020077802A KR 100491944 B1 KR100491944 B1 KR 100491944B1
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- polyamic acid
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- 238000000034 method Methods 0.000 title claims abstract description 4
- 229920001721 polyimide Polymers 0.000 title abstract description 18
- 125000005462 imide group Chemical group 0.000 title abstract description 7
- 239000004642 Polyimide Substances 0.000 title description 8
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 49
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims 1
- 238000006358 imidation reaction Methods 0.000 claims 1
- 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 abstract description 25
- 150000004984 aromatic diamines Chemical class 0.000 abstract description 10
- 150000004985 diamines Chemical class 0.000 abstract description 10
- 239000009719 polyimide resin Substances 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 abstract description 6
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- -1 aromatic tetracarboxylic acid Chemical class 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 16
- 239000010408 film Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000003949 imides Chemical group 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- MHALQPUFCVTXKV-UHFFFAOYSA-N 3-hex-1-enyloxolane-2,5-dione Chemical compound CCCCC=CC1CC(=O)OC1=O MHALQPUFCVTXKV-UHFFFAOYSA-N 0.000 description 7
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 7
- 239000006184 cosolvent Substances 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- WVOLTBSCXRRQFR-SJORKVTESA-N Cannabidiolic acid Natural products OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-SJORKVTESA-N 0.000 description 6
- WVOLTBSCXRRQFR-DLBZAZTESA-M cannabidiolate Chemical compound OC1=C(C([O-])=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-M 0.000 description 6
- 229960002317 succinimide Drugs 0.000 description 6
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 6
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 210000002858 crystal cell Anatomy 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- MHNMEERHZSPWFL-NSOVKSMOSA-N 4-[(1s)-1-amino-1-(3-methylimidazol-4-yl)ethyl]-2-[3-[(3s)-3-ethyl-1-methyl-2-oxoazepan-3-yl]phenoxy]benzonitrile Chemical compound C=1C=CC(OC=2C(=CC=C(C=2)[C@](C)(N)C=2N(C=NC=2)C)C#N)=CC=1[C@]1(CC)CCCCN(C)C1=O MHNMEERHZSPWFL-NSOVKSMOSA-N 0.000 description 3
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- BZUNJUAMQZRJIP-UHFFFAOYSA-N CPDA Natural products OCCCCCCCCCCCCCCC(O)=O BZUNJUAMQZRJIP-UHFFFAOYSA-N 0.000 description 2
- 101150059231 CPI1 gene Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 101150002418 cpi-2 gene Proteins 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GISJHCLTIVIGLX-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methoxy]pyridin-2-yl]-2-(2,6-difluorophenyl)acetamide Chemical compound FC1=CC=CC(F)=C1CC(=O)NC1=CC(OCC=2C=CC(Cl)=CC=2)=CC=N1 GISJHCLTIVIGLX-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- MPBZUKLDHPOCLS-UHFFFAOYSA-N 3,5-dinitroaniline Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 MPBZUKLDHPOCLS-UHFFFAOYSA-N 0.000 description 1
- UYCICMIUKYEYEU-ZHACJKMWSA-N 3-[(e)-dodec-2-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCC\C=C\CC1CC(=O)OC1=O UYCICMIUKYEYEU-ZHACJKMWSA-N 0.000 description 1
- UWERUIGPWOVNGG-UHFFFAOYSA-N 3-dec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCC=CC1CC(=O)OC1=O UWERUIGPWOVNGG-UHFFFAOYSA-N 0.000 description 1
- RSPWVGZWUBNLQU-UHFFFAOYSA-N 3-hexadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCC=CC1CC(=O)OC1=O RSPWVGZWUBNLQU-UHFFFAOYSA-N 0.000 description 1
- FLISWPFVWWWNNP-UHFFFAOYSA-N 3-oct-1-enyloxolane-2,5-dione Chemical compound CCCCCCC=CC1CC(=O)OC1=O FLISWPFVWWWNNP-UHFFFAOYSA-N 0.000 description 1
- KAYAKFYASWYOEB-UHFFFAOYSA-N 3-octadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CC1CC(=O)OC1=O KAYAKFYASWYOEB-UHFFFAOYSA-N 0.000 description 1
- URVNZJUYUMEJFZ-UHFFFAOYSA-N 3-tetradec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCC=CC1CC(=O)OC1=O URVNZJUYUMEJFZ-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
- BZWUYTRSEXHNEX-UHFFFAOYSA-N 6-(1,1,1,3,3,3-hexafluoropropan-2-yl)cyclohexa-2,4-diene-1,1-diamine Chemical compound NC1(C(C=CC=C1)C(C(F)(F)F)C(F)(F)F)N BZWUYTRSEXHNEX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- 239000003779 heat-resistant material Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Classifications
-
- 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
- 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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nonlinear Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
구 분 | 폴리아믹산중합체 | 폴리이미드 유도체 | ||||
폴리아믹산 | 고유점도*) (dL/g) | 폴리이미드 | 유리전이온도(℃) | 표면장력(dyne/cm) | 연필경도 | |
실시예 15 | DPAA-1 | 0.94 | DPI-1 | 331 | 45 | 4H |
실시예 16 | DPAA-2 | 0.72 | DPI-2 | 318 | 43 | 3H |
실시예 17 | DPAA-3 | 0.85 | DPI-3 | 305 | 39 | 3H |
실시예 18 | CPAA-1 | 0.92 | CPI-1 | 270 | 34 | 5H |
실시예 19 | CPAA-2 | 0.87 | CPI-2 | 265 | 32 | 4H |
실시예 20 | CPAA-3 | 0.91 | CPI-3 | 260 | 30 | 4H |
비교예 1 | DPAA-0 | 1.15 | DPI-0 | 330 | 50 | B |
비교예 2 | CPAA-0 | 1.30 | CPI-0 | 275 | 41 | HB |
*)NMP을 용매로 하여 0.5 g/dL의 농도로 30 ℃에서 측정. |
구 분 | 배향막 | 선경사각 (°) | VHR(%) (상온) |
실시예 15 | DPI-1 | 89.0 | 98 |
실시예 16 | DPI-2 | 89.8 | 98 |
실시예 17 | DPI-3 | 89.9 | 98 |
실시예 18 | CPI-1 | 88.0 | 99 |
실시예 19 | CPI-2 | 88.0 | 99 |
실시예 20 | CPI-3 | 89.5 | 99 |
비교예 1 | DPI-0 | 2.0 | 98 |
비교예 2 | CPI-0 | 2.5 | 99 |
Claims (8)
- 다음 화학식 1로 표시되는 것임을 특징으로 하는 액정배향막용 폴리아믹산 유도체;[화학식 1]상기 화학식 1에서 :은 , , , , , , , , , 및 중에서 선택된 1종 또는 2종 이상의 4가기로서, 반드시 (a), (b), (c), (d) 및 (e) 중에서 선택된 1종 또는 2종 이상의 4가기를 포함하며;는 , , , , , , , ,, , 및중에서 선택된 1종 또는 2종 이상의 2가기로서, 반드시 (f)를 포함하며; n은 1 내지 300 범위의 자연수이고 m 은 1 내지 30 범위의 자연수를 나타낸다.
- 제 1 항에 있어서, 상기 화학식 1로 표시되는 폴리아믹산 유도체의 고유점도가 0.3 내지 1.5 dL/g의 범위인 것을 특징으로 하는 액정배향막용 폴리아믹산 유도체.
- 제 1 항에 있어서, 상기 화학식 1로 표시되는 폴리아믹산 유도체의 분자량이 10,000 내지 150,000 g/mol의 범위인 것을 특징으로 하는 액정배향막용 폴리아믹산 유도체.
- 제 1 항에 있어서, 상기 화학식 1로 표시되는 폴리아믹산 유도체의 유리전이온도가 230 내지 400 ℃의 범위인 것을 특징으로 하는 액정배향막용 폴리아믹산 유도체.
- 제 1 항에 있어서, 상기 화학식 1로 표시되는 폴리아믹산 유도체의 선경사각(pretilt angle)이 85 내지 89.9°범위인 것을 특징으로 하는 액정배향막용 폴리아믹산 유도체.
- 제 1 항에 있어서, 상기 화학식 1로 표시되는 폴리아믹산 유도체는 디메틸아세트아미드, 디메틸포름아미드, N-메틸-2-피롤리돈, 테트라히드로푸란, 클로로포름, 아세톤, 에틸아세테이트 및 감마-부티로락톤 중에서 선택된 용매에 대해 용해특성을 가지는 것을 특징으로 하는 액정배향막용 폴리아믹산 유도체.
- 제 1 항에 있어서, 상기 화학식 1로 표시되는 폴리아믹산 유도체의 이미드화 온도범위가 200 ∼ 300 ℃인 것을 특징으로 하는 액정배향막용 폴리아믹산 유도체.
- 다음 화학식 2로 표시되는 것임을 특징으로 하는 액정배향막용 폴리아믹산 제조용 단량체.[화학식 2]여기서, m은 1 내지 30 범위의 자연수를 나타낸다.
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KR100552989B1 (ko) * | 2004-02-12 | 2006-02-17 | 한국화학연구원 | 전유기 박막트랜지스터 절연체용 감광성 폴리아믹산 및이로부터 제조된 폴리이미드 수지 |
KR100552135B1 (ko) * | 2004-06-14 | 2006-02-14 | 한국화학연구원 | 액정배향막 조성물 |
KR100552134B1 (ko) * | 2004-06-14 | 2006-02-14 | 한국화학연구원 | 알킬숙시닉이미드 측쇄가 도입된 지방족 고리계 가용성폴리이미드 수지 |
KR100622026B1 (ko) * | 2004-10-29 | 2006-09-19 | 한국화학연구원 | 가용성 폴리이미드 수지를 함유한 절연막 및 이를 이용한전유기 박막 트랜지스터 |
KR100559264B1 (ko) * | 2004-10-29 | 2006-03-15 | 한국화학연구원 | 저극성 폴리아믹산 수지를 함유하는 수직배향형 조성물 및이를 이용한 액정 배향막과 액정 셀 |
KR100782436B1 (ko) * | 2005-12-30 | 2007-12-05 | 제일모직주식회사 | 액정 배향제 |
KR100782437B1 (ko) * | 2005-12-30 | 2007-12-05 | 제일모직주식회사 | 액정 배향제 |
JP5077558B2 (ja) * | 2007-02-15 | 2012-11-21 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
JP5071659B2 (ja) * | 2007-02-22 | 2012-11-14 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
JP5105071B2 (ja) * | 2007-02-27 | 2012-12-19 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
JP5013105B2 (ja) * | 2007-03-06 | 2012-08-29 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
KR100802576B1 (ko) * | 2007-06-20 | 2008-02-13 | 한국화학연구원 | 낮은 선경사각을 갖는 액정배향막용 폴리아믹산 조성물 및이로부터 제조된 가용성 폴리이미드 수지 |
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CN102102019A (zh) | 2009-12-16 | 2011-06-22 | 第一毛织株式会社 | 液晶光取向剂、液晶光取向层及其液晶显示器装置 |
CN102559205B (zh) * | 2010-12-29 | 2014-07-30 | 第一毛织株式会社 | 液晶取向剂、使用其制造的液晶取向膜和液晶显示器 |
KR101333711B1 (ko) * | 2010-12-29 | 2013-11-27 | 제일모직주식회사 | 액정 배향제, 이를 이용하여 제조한 액정 배향막 및 상기 액정 배향막을 포함하는 액정표시소자 |
KR101444190B1 (ko) | 2011-12-19 | 2014-09-26 | 제일모직 주식회사 | 액정 배향제, 이를 이용한 액정 배향막 및 상기 액정 배향막을 포함하는 액정표시소자 |
KR101990286B1 (ko) | 2015-12-18 | 2019-06-18 | 주식회사 엘지화학 | 수직 배향막 |
KR102097284B1 (ko) * | 2019-11-19 | 2020-04-06 | 솔루텍 주식회사 | 구내교환기 및 안내서버를 이용한 메시지 제공 방법 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61271286A (ja) * | 1985-05-28 | 1986-12-01 | Mitsui Toatsu Chem Inc | ポリイミドオリゴマー、及びそのオリゴマーを含有してなる耐熱性接着剤 |
EP0721010A1 (en) * | 1994-12-30 | 1996-07-10 | Chevron Chemical Company | Fuel compositions containing aryl succinimides |
US6238752B1 (en) * | 1998-07-29 | 2001-05-29 | Chisso Corporation | Diamino compounds, polyamic acids, polyimides, liquid crystal aligning films using said polyimide films and liquid crystal display devices using said aligning films |
KR100310092B1 (ko) * | 1998-11-18 | 2001-11-07 | 윤종용 | 광통신용 폴리이미드, 그 제조방법 및 그것을 이용한 다층 폴리이미드막의 형성방법 |
KR20020055837A (ko) * | 2000-12-29 | 2002-07-10 | 안복현 | 폴리아믹산 수지 조성물 |
KR100358075B1 (ko) * | 1999-11-30 | 2003-01-24 | 한국화학연구원 | 고경도 투명 지방족 폴리이미드계 나노 복합 소재 |
-
2002
- 2002-12-09 KR KR10-2002-0077802A patent/KR100491944B1/ko not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61271286A (ja) * | 1985-05-28 | 1986-12-01 | Mitsui Toatsu Chem Inc | ポリイミドオリゴマー、及びそのオリゴマーを含有してなる耐熱性接着剤 |
EP0721010A1 (en) * | 1994-12-30 | 1996-07-10 | Chevron Chemical Company | Fuel compositions containing aryl succinimides |
US6238752B1 (en) * | 1998-07-29 | 2001-05-29 | Chisso Corporation | Diamino compounds, polyamic acids, polyimides, liquid crystal aligning films using said polyimide films and liquid crystal display devices using said aligning films |
KR100310092B1 (ko) * | 1998-11-18 | 2001-11-07 | 윤종용 | 광통신용 폴리이미드, 그 제조방법 및 그것을 이용한 다층 폴리이미드막의 형성방법 |
KR100358075B1 (ko) * | 1999-11-30 | 2003-01-24 | 한국화학연구원 | 고경도 투명 지방족 폴리이미드계 나노 복합 소재 |
KR20020055837A (ko) * | 2000-12-29 | 2002-07-10 | 안복현 | 폴리아믹산 수지 조성물 |
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