JP6319581B2 - 液晶配向剤、液晶配向膜及び液晶表示素子 - Google Patents
液晶配向剤、液晶配向膜及び液晶表示素子 Download PDFInfo
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- JP6319581B2 JP6319581B2 JP2014529518A JP2014529518A JP6319581B2 JP 6319581 B2 JP6319581 B2 JP 6319581B2 JP 2014529518 A JP2014529518 A JP 2014529518A JP 2014529518 A JP2014529518 A JP 2014529518A JP 6319581 B2 JP6319581 B2 JP 6319581B2
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- liquid crystal
- bis
- aminophenyl
- polyamic acid
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 184
- 239000003795 chemical substances by application Substances 0.000 title claims description 53
- 229920005575 poly(amic acid) Polymers 0.000 claims description 73
- 150000004985 diamines Chemical class 0.000 claims description 58
- 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 54
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 50
- 229920001721 polyimide Polymers 0.000 claims description 44
- 239000004642 Polyimide Substances 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 40
- -1 4-aminobenzoyloxy Chemical group 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 27
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 4
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 3
- XIIAYQZJNBULGD-UHFFFAOYSA-N (5alpha)-cholestane Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XIIAYQZJNBULGD-UHFFFAOYSA-N 0.000 claims 6
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims 6
- XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 claims 6
- 229940064734 aminobenzoate Drugs 0.000 claims 5
- 239000000178 monomer Substances 0.000 claims 4
- BXXXLNALTXSMEJ-UHFFFAOYSA-N 4-n-(4-aminophenyl)-4-n-(4-methylphenyl)benzene-1,4-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 BXXXLNALTXSMEJ-UHFFFAOYSA-N 0.000 claims 2
- 150000004986 phenylenediamines Chemical class 0.000 claims 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims 1
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- 238000000034 method Methods 0.000 description 33
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- 125000000217 alkyl group Chemical group 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 19
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- 125000004432 carbon atom Chemical group C* 0.000 description 16
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- 229910052731 fluorine Inorganic materials 0.000 description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 12
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- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- IPLONMMJNGTUAI-UHFFFAOYSA-M lithium;bromide;hydrate Chemical compound [Li+].O.[Br-] IPLONMMJNGTUAI-UHFFFAOYSA-M 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- VNRDAMBPFDPXSM-UHFFFAOYSA-N n'-[2-(3-triethoxysilylpropylamino)ethyl]ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCNCCN VNRDAMBPFDPXSM-UHFFFAOYSA-N 0.000 description 1
- NHBRUUFBSBSTHM-UHFFFAOYSA-N n'-[2-(3-trimethoxysilylpropylamino)ethyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCN NHBRUUFBSBSTHM-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- ILRLVKWBBFWKTN-UHFFFAOYSA-N n-benzyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCC1=CC=CC=C1 ILRLVKWBBFWKTN-UHFFFAOYSA-N 0.000 description 1
- CLYWMXVFAMGARU-UHFFFAOYSA-N n-benzyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCC1=CC=CC=C1 CLYWMXVFAMGARU-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- OKBVMLGZPNDWJK-UHFFFAOYSA-N naphthalene-1,4-diamine Chemical compound C1=CC=C2C(N)=CC=C(N)C2=C1 OKBVMLGZPNDWJK-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 1
- HBJPJUGOYJOSLR-UHFFFAOYSA-N naphthalene-2,7-diamine Chemical compound C1=CC(N)=CC2=CC(N)=CC=C21 HBJPJUGOYJOSLR-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- JCMFJIHDWDKYIL-UHFFFAOYSA-N propyl 3-methoxypropanoate Chemical compound CCCOC(=O)CCOC JCMFJIHDWDKYIL-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229940032159 propylene carbonate Drugs 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- JREWFSHZWRKNBM-UHFFFAOYSA-N pyridine-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1=CN=C(C(O)=O)C(C(O)=O)=C1C(O)=O JREWFSHZWRKNBM-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000002345 steroid group Chemical group 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 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
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
-
- 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
- C08G73/1075—Partially aromatic polyimides
-
- 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
- C08G73/14—Polyamide-imides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on 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 C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133723—Polyimide, polyamide-imide
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/59—Stability
- C08G2261/594—Stability against light, i.e. electromagnetic radiation
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- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Liquid Crystal (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明の液晶配向剤は、上記式(1)で表されるテトラカルボン酸二無水物とジアミン成分とを重合反応させることにより得られるポリアミック酸、及び、このポリアミック酸をイミド化して得られるポリイミドから選択される少なくとも一種の重合体と、溶剤とを含有するものである。なお、液晶配向剤とは液晶配向膜を作製するための溶液であり、液晶配向膜とは液晶を所定の方向に配向させるための膜である。
また、本発明の液晶配向剤が含有する溶剤は、上記ポリイミドや、ポリアミック酸を溶解することができるものであれば、特に限定はされず、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチル−2−ピロリドン、N−メチルカプロラクタム、2−ピロリドン、N−エチル−2−ピロリドン、N−ビニルピロリドン、ジメチルスルホキシド、テトラメチル尿素、ピリジン、ジメチルスルホン、ヘキサメチルスルホキシド、γ−ブチロラクトン、1,3−ジメチル−イミダゾリジノン、エチルアミルケトン、メチルノニルケトン、メチルエチルケトン、メチルイソアミルケトン、メチルイソプロピルケトン、シクロヘキサノン、エチレンカーボネート、プロピレンカーボネート、ジグライムおよび4−ヒドロキシ−4−メチル−2−ペンタノンなどの有機溶媒が挙げられる。これらは単独で使用しても、混合して使用してもよい。
本発明の液晶配向剤は、重合体成分が、上記式(1)で表されるテトラカルボン酸二無水物とジアミン成分とを重合反応させることにより得られるポリアミック酸及びこのポリアミック酸をイミド化して得られるポリイミドから選択される少なくとも一種の重合体のみであってもよく、上記式(1)で表されるテトラカルボン酸二無水物とジアミン成分とを重合反応させることにより得られるポリアミック酸及びこのポリアミック酸をイミド化して得られるポリイミドから選択される少なくとも一種の重合体にそれ以外の他の重合体が混合されていてもよい。その際、上記式(1)で表されるテトラカルボン酸二無水物とジアミン成分とを重合反応させることにより得られるポリアミック酸及びこのポリアミック酸をイミド化して得られるポリイミドから選択される少なくとも一種の重合体の総量に対して、それ以外の他の重合体の含有量は0.5〜15質量%、好ましくは1.0〜10質量%である。それ以外の他の重合体としては、上記式(1)で表されるテトラカルボン酸二無水物を含まないテトラカルボン酸二無水物成分とジアミン成分とから得られるポリアミック酸や、ポリイミドが挙げられる。さらには、ポリアミック酸およびポリイミド以外の重合体、具体的には、ポリアミック酸エステル、アクリルポリマー、メタクリルポリマー、ポリスチレンまたはポリアミドなども挙げられる。
本発明の液晶配向剤は、基板上に塗布、焼成した後、ラビング処理や光照射などで配向処理をして、液晶配向膜として用いることができる。また、垂直配向用途などの場合では配向処理なしでも液晶配向膜として用いることができる。この際に用いる基板としては、透明性の高い基板であれば特に限定されず、ガラス基板の他、アクリル基板やポリカーボネート基板などのプラスチック基板なども用いることができる。プロセスの簡素化の観点からは、液晶駆動のためのITO(Indium Tin Oxide)電極などが形成された基板を用いることが好ましい。また、反射型の液晶表示素子では、片側の基板のみにならばシリコンウェハなどの不透明な基板も使用でき、この場合の電極としてはアルミなどの光を反射する材料も使用できる。
PPHT:下記式で示されるN,N’−ビス(1,2−シクロヘキサンジカルボン酸無水物−4−イル)カルボニル−1,4−フェニレンジアミン
PSHT:下記式で示されるN,N’−ビス(1,2−シクロヘキサンジカルボン酸無水物−4−イル)カルボニル−3,3’−ジアミノジフェニルスルホン
CBDA:1,2,3,4−シクロブタンテトラカルボン酸二無水物
TDA:3,4−ジカルボキシ−1,2,3,4−テトラヒドロ−1−ナフタレンコハク酸二無水物
BAPU:1,3−ビス(4−アミノフェニチル)ウレア
DDM:4,4’−ジアミノジフェニルメタン
DADA:N,N−ジアリル−2,4−ジアミノアニリン
APC16:1,3−ジアミノ−4−ヘキサデシルオキシベンゼン
APC18:1,3−ジアミノ−4−オクタデシルオキシベンゼン
p−PDA:p−フェニレンジアミン
NMP:N−メチル−2−ピロリドン
BCS:2−ブトキシエタノール
<分子量の測定>
ポリアミック酸およびポリイミドの分子量は、該ポリアミック酸やポリイミドをGPC(常温ゲル浸透クロマトグラフィー)装置によって測定し、ポリエチレングリコール、ポリエチレンオキシド換算値として数平均分子量と重量平均分子量を算出した。
GPC装置:Shodex社製(GPC−101)
カラム:Shodex社製(KD803、KD805の直列)
カラム温度:50℃
溶離液:N,N−ジメチルホルムアミド(添加剤として、臭化リチウム−水和物(LiBr・H2O)が30ミリモル/L、リン酸・無水結晶(o−リン酸)が30ミリモル/L、テトラヒドロフラン(THF)が10ml/L)
流速:1.0ml/分
検量線作製用標準サンプル:東ソー社製 TSK 標準ポリエチレンオキサイド(分子量約900000、150000、100000、30000)、および、ポリマーラボラトリー社製ポリエチレングリコール(分子量約12000、4000、1000)。
ポリイミドのイミド化率は次のようにして測定した。
ポリイミド粉末20mgをNMRサンプル管に入れ、重水素化ジメチルスルホキシド(DMSO−d6、0.05%TMS(テトラメチルシラン)混合品)0.53mlを添加し、完全に溶解させた。この溶液を日本電子データム社製NMR測定器(JNM−ECA500)にて500MHzのプロトンNMRを測定した。イミド化率は、イミド化前後で変化しない構造に由来するプロトンを基準プロトンとして決め、このプロトンのピーク積算値と、9.5ppm〜10.0ppm付近に現れるアミック酸のNH基に由来するプロトンピーク積算値とを用い次式によって求めた。
イミド化率(%)=(1−α・x/y)×100
上記式において、xはアミック酸のNH基由来のプロトンピーク積算値、yは基準プロトンのピーク積算値、αはポリアミック酸(イミド化率が0%)の場合におけるアミック酸のNH基プロトン一個に対する基準プロトンの個数割合である。
テトラカルボン酸二無水物成分として、PPHTを1.33g、ジアミン成分として、p−PDAを0.32g用い、NMP14.93g中、室温で18時間反応させ、ポリアミック酸(PAA−1)の固形分濃度10wt%の溶液を得た。
表2に示す組成にした以外は上記合成例1と同様の方法を用いて、合成例2〜10のポリアミック酸(PAA−2〜PAA−10)の溶液を得た。
合成例1で得られたポリアミック酸(PAA−1)の溶液15.1gに、NMPを12.59g加えて希釈し、固形分濃度6wt%のポリアミック酸溶液を調製した。このポリアミック酸溶液に無水酢酸2.95gとピリジン1.37gを加え、50℃で3時間反応させてイミド化した。得られたポリイミド溶液を室温程度まで冷却後、メタノール150g中に投入し、沈殿した固形物を回収した。さらに、この固形物をメタノールで2回洗浄した後、100℃で減圧乾燥して、ポリイミド(SPI−1)の黄土色粉末を得た。ポリイミド(SPI−1)のイミド化率を測定した結果、79%であった。
表3に示す組成にした以外は上記合成例11と同様の方法を用いて、合成例12〜18のポリイミド(SPI−2〜SPI−8)の粉末を得た。
上記合成例1にて得られたポリマー(ポリアミック酸PAA−1)の溶液3.25gに、NMP3.25gを加え、室温で3時間攪拌した。攪拌終了時点でポリアミック酸は完全に溶解していた。さらにこの溶液にBCS1.63gを加え、室温で1時間攪拌し、固形分濃度が4.0wt%のポリマー溶液(A1)を得た。このポリマー溶液は、そのまま液晶配向膜を形成するための液晶配向剤となる。
表4に示す組成にした以外は、実施例1と同様の方法を用いて、実施例2〜7のポリマー溶液(A2〜A7)、及び、比較例1〜2のポリマー溶液(B1〜B2)を得た。
上記合成例11にて得られたポリマー(ポリイミドSPI−1)0.50gに、NMP7.53gを加え、室温で3時間攪拌した。攪拌終了時点でポリイミドは完全に溶解していた。さらにこの溶液にBCS2.01gを加え、室温で1時間攪拌し、固形分濃度が5.0wt%、のポリマー溶液(A8)を得た。このポリマー溶液は、そのまま液晶配向膜を形成するための液晶配向剤となる。
表5に示す組成にした以外は、実施例8と同様の方法を用いて、実施例9〜13のポリマー溶液(A9〜A13)、及び、比較例3〜4のポリマー溶液(B3〜B4)を得た。なお、いずれの実施例9〜13においても、実施例8と同様に、攪拌終了時点でポリイミドは完全に溶解していた。
実施例1で得られたポリマー溶液(A1)すなわち液晶配向剤(A1)を1.0μmのフィルターで濾過した後、透明電極付きガラス基板上にスピンコートし、80℃のホットプレート上で80秒間乾燥後、230℃で10分間焼成して膜厚100nmの塗膜(ポリイミド膜)を得た。このポリイミド膜をレーヨン布でラビング(ロール径120mm、回転数1000rpm、移動速度50mm/sec、押し込み量0.3mm)した後、純水中にて1分間超音波照射を行い、80℃で10分間乾燥して、液晶配向膜を形成した。このような液晶配向膜付き基板を2枚用意し、一方の基板の液晶配向膜面に6μmのスペーサを設置した後、2枚の基板のラビング方向が直交するようにして組み合わせ、液晶注入口を残して周囲をシールし、セルギャップが6μmの空セルを作製した。このセルに液晶(MLC−2003(C080)、メルク・ジャパン社製)を常温で真空注入し、注入口を封止して、液晶が90度ツイスト配向した液晶セルを得た。
電圧保持率の評価は、得られた液晶セルに、90℃の温度下で4Vの電圧を60μs間印加し、16.67ms後の電圧を測定し、電圧がどのくらい保持できているか、すなわち、初期値からの変動を電圧保持率として計算した。なお、電圧保持率の測定には、東陽テクニカ社製の電圧保持率測定装置VHR−1を使用した。この評価結果(表6において「初期」と記載する。)を表6に示す。
得られた液晶セルについて、120℃で1時間加熱した後、プレチルト角の測定を行った。プレチルト角はAxo Metrix社の「Axo Scan」にて、ミュラーマトリクス法を用いて測定した。結果を表6に示す。
実施例1〜13及び比較例1〜4で得られた各液晶配向剤(ポリマー溶液)を、Cr基板上にそれぞれ約0.1ml滴下し、温度23℃、湿度55%の環境に放置した。この液滴の端近傍付近を10分毎に顕微鏡で観察した。尚、観察は100倍の倍率で行った。凝集物が発生した時間が10分以下のものを×、10分超1時間未満を△、1時間以上3時間未満を○、3時間以上を◎として評価した。評価結果を表6に示す。
Claims (3)
- 下記式(1)で表されるテトラカルボン酸二無水物とジアミン成分とを重合反応させることにより得られるポリアミック酸をイミド化して得られるポリイミドから選択される少なくとも一種の重合体(ただし、モノマーが下記式(t−1−1)で表されるテトラカルボン酸二無水物、4−アミノフェニル−4’−アミノベンゾエート(BAAB)、3,6−ビス(4−アミノベンゾイルオキシ)コレスタン(NCDA)、テトラデカノキシ−2,4−ジアミノベンゼン(TETRAMIN)、及び4,4’−[4,4’−プロパン−1,3−ジイルビス(ピペリジン−1,4−ジイル)]ジアニリン(BISP)であるポリアミック酸;モノマーが下記式(t−1−1)で表されるテトラカルボン酸二無水物、4−アミノフェニル−4’−アミノベンゾエート(BAAB)、3,6−ビス(4−アミノベンゾイルオキシ)コレスタン(NCDA)、テトラデカノキシ−2,4−ジアミノベンゼン(TETRAMIN)、4,4’−[4,4’−プロパン−1,3−ジイルビス(ピペリジン−1,4−ジイル)]ジアニリン(BISP)、及びN,N−ビス(4−アミノフェニル)−p−メチルフェニルアミン(DADPA−ToL)であるポリアミック酸;モノマーが下記式(t−1−1)で表されるテトラカルボン酸二無水物、ピロメリット酸二無水物(PMDA)、4−アミノフェニル−4’−アミノベンゾエート(BAAB)、3,6−ビス(4−アミノベンゾイルオキシ)コレスタン(NCDA)、テトラデカノキシ−2,4−ジアミノベンゼン(TETRAMIN)、及び4,4’−[4,4’−プロパン−1,3−ジイルビス(ピペリジン−1,4−ジイル)]ジアニリン(BISP)であるポリアミック酸;モノマーが下記式(t−1−1)で表されるテトラカルボン酸二無水物、ピロメリット酸二無水物(PMDA)、4−アミノフェニル−4’−アミノベンゾエート(BAAB)、3,6−ビス(4−アミノベンゾイルオキシ)コレスタン(NCDA)、テトラデカノキシ−2,4−ジアミノベンゼン(TETRAMIN)、4,4’−[4,4’−プロパン−1,3−ジイルビス(ピペリジン−1,4−ジイル)]ジアニリン(BISP)、及びN,N−ビス(4−アミノフェニル)−p−メチルフェニルアミン(DADPA−ToL)であるポリアミック酸;モノマーが下記式(t−1−1)で表されるテトラカルボン酸二無水物、4−アミノフェニル−4’−アミノベンゾエート(BAAB)、3,6−ビス(4−アミノベンゾイルオキシ)コレスタン(NCDA)、テトラデカノキシ−2,4−ジアミノベンゼン(TETRAMIN)、N,N−ビス(4−アミノフェニル)−p−メチルフェニルアミン(DADPA−ToL)、及びp−フェニレンジアミン(PDA)であるポリイミド;モノマーが下記式(t−1−1)で表されるテトラカルボン酸二無水物、ピロメリット酸二無水物(PMDA)、4−アミノフェニル−4’−アミノベンゾエート(BAAB)、3,6−ビス(4−アミノベンゾイルオキシ)コレスタン(NCDA)、テトラデカノキシ−2,4−ジアミノベンゼン(TETRAMIN)、N,N−ビス(4−アミノフェニル)−p−メチルフェニルアミン(DADPA−ToL)、及びp−フェニレンジアミン(PDA)であるポリイミド;を除く)と、溶剤とを含有することを特徴とする液晶配向剤。
- 請求項1に記載する液晶配向剤を用いて得られることを特徴とする液晶配向膜。
- 請求項2に記載する液晶配向膜を具備することを特徴とする液晶表示素子。
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