CN109423308A - Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element - Google Patents
Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element Download PDFInfo
- Publication number
- CN109423308A CN109423308A CN201810946503.6A CN201810946503A CN109423308A CN 109423308 A CN109423308 A CN 109423308A CN 201810946503 A CN201810946503 A CN 201810946503A CN 109423308 A CN109423308 A CN 109423308A
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- Prior art keywords
- liquid crystal
- carbon number
- formula
- polymer
- aligning agent
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- 125000000217 alkyl group Chemical group 0.000 claims description 18
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- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- JWXLCQHWBFHMOI-NIQMUPOESA-N bis[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] carbonate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C(C1)[C@]2(C)CC[C@@H]1OC(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 JWXLCQHWBFHMOI-NIQMUPOESA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- 239000001405 butyl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- DWQUPUUWCRSMLZ-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1(CCCCC1)C1=CC=CC=C1.C1(=CC=CC=C1)C1CCCCC1 DWQUPUUWCRSMLZ-UHFFFAOYSA-N 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical class [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 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
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- CBLAIDIBZHTGLV-UHFFFAOYSA-N dodecane-2,11-diamine Chemical compound CC(N)CCCCCCCCC(C)N CBLAIDIBZHTGLV-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000005685 electric field effect Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- HFKBPAKZRASAGX-UHFFFAOYSA-N ethane-1,1,1,2-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)(C(O)=O)C(O)=O HFKBPAKZRASAGX-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940035423 ethyl ether Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MVUXVDIFQSGECB-UHFFFAOYSA-N ethyl n-(3-triethoxysilylpropyl)carbamate Chemical compound CCOC(=O)NCCC[Si](OCC)(OCC)OCC MVUXVDIFQSGECB-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 229910052738 indium 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
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- IIYFAKIEWZDVMP-UHFFFAOYSA-N linear paraffin C13 Natural products CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DKJCSMHIPYRALV-UHFFFAOYSA-N methoxymethyl propanoate Chemical compound CCC(=O)OCOC DKJCSMHIPYRALV-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
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 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
- 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 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- VQXBKCWOCJSIRT-UHFFFAOYSA-N octadecane-1,12-diamine Chemical compound CCCCCCC(N)CCCCCCCCCCCN VQXBKCWOCJSIRT-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 208000007578 phototoxic dermatitis Diseases 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-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
- IOXGEAHHEGTLMQ-UHFFFAOYSA-N pyridazine Chemical class C1=CC=NN=C1.C1=CC=NN=C1 IOXGEAHHEGTLMQ-UHFFFAOYSA-N 0.000 description 1
- YMXFJTUQQVLJEN-UHFFFAOYSA-N pyrimidine Chemical class C1=CN=CN=C1.C1=CN=CN=C1 YMXFJTUQQVLJEN-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- YIBXWXOYFGZLRU-UHFFFAOYSA-N syringic aldehyde Natural products CC12CCC(C3(CCC(=O)C(C)(C)C3CC=3)C)C=3C1(C)CCC2C1COC(C)(C)C(O)C(O)C1 YIBXWXOYFGZLRU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
-
- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use 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 C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Manufacturing & Machinery (AREA)
- Mathematical Physics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Liquid Crystal (AREA)
Abstract
The invention provides a liquid crystal alignment agent, a liquid crystal alignment film and a liquid crystal display element. The liquid crystal aligning agent comprises a polymer (A) having a specific diamine compound (B-1), a solvent (B), and an additive (C) containing a specific carboxylic acid compound (C-1). The liquid crystal alignment film is prepared from the liquid crystal alignment agent, and the liquid crystal display element comprising the liquid crystal alignment film has good charge elimination light resistance.
Description
Technical field
The invention relates to a kind of crystal aligning agent, liquid crystal orienting film and liquid crystal display elements, especially with regard to one kind
Using the crystal aligning agent, the good liquid crystal display element of light resistance is eliminated so that charge is made.
Background technique
For the liquid crystal display element of LCD TV, liquid crystal display etc., control liquid crystal usually is internally provided in element
The liquid crystal orienting film of ordered state.The industrial most common method is to be rubbed with the cloth such as cotton, nylon, polyester material along a direction at present
It wipes formation and is formed by film surface on the electrode substrate, by polyamic acid and/or by the polyimides of its imidizate, carry out institute
The friction treatment of meaning and this liquid crystal orienting film is made.
It is the method for being industrially relatively easy to production that film surface, which is carried out friction treatment, in the process of alignment of liquid crystal orienting film.
However, rubbing as high-effectization to liquid crystal display element, high-fineness, the requirement of enlargement are higher and higher
When processing, by the damage of orientation film surface, flying dust, because being influenced caused by mechanical force and electrostatic force and in orientation process face
On various problem such as inhomogeneities become more significant.
As the method for replacing friction treatment, it is currently known and assigns LCD alignment using because the ultraviolet light of polarisation irradiates
The light alignment method of energy.The LCD alignment processing of so-called light alignment method is to utilize photoisomerization on reaction mechanism such as
(photoisomerization) substance that reacts, using photo-crosslinking (photocrosslink) reaction substance, utilize light point
Solve the substance etc. of reaction.Furthermore Japanese Laid-Open Patent Publication 9-297313 bulletin proposes, light alignment method has the rouge of cyclobutane etc. using main chain
The polyimide film of ring construction.When using polyimides as light orientation alignment film, because of the heat resistance of alignment film thus
Higher than other kinds of alignment film, therefore have an optimistic view of the application of such alignment film.
Light alignment method is the method for not friction matching processing, and industrially not only having can be manufactured using simple processing procedure
The advantages of, in transverse electric field effect technology (In-Plane-Switching；IPS) driving method and boundary electric field switch wide viewing angle
Technology (Fringe Field Switching；FFS) in the liquid crystal display element of driving method, compared to using friction treatment method
Resulting liquid crystal orienting film, when liquid crystal orienting film resulting using above-mentioned light alignment method, it is expected to promote pair of liquid crystal display element
Than degree and viewing angle characteristic, therefore light alignment method is the LCD alignment processing method to attract attention with prospect.
However, still having charge elimination when being applied to liquid crystal display element by liquid crystal orienting film obtained by light alignment method
The bad problem of light resistance, that is, the savings charge of liquid crystal orienting film liquid crystal display element obtained after irradiation eliminate it is slow
Slowly, the problem of causing residual charge excessively high, and then generating ghost.It can be seen from the above, in order to meet current light orientation IPS type liquid crystal
The requirement of display dealer provides a kind of crystal aligning agent that can be formed charge and eliminate the good liquid crystal display element of light resistance, is
The art person makes great efforts the target of research.
Summary of the invention
The liquid crystal that the good liquid crystal display element of charge elimination light resistance can be formed the purpose of the present invention is to provide one kind is matched
To agent.
One aspect of the present invention is to provide a kind of crystal aligning agent, it includes polymer (A), solvent (B) and add
Agent (C).
It it is another aspect of the invention to provide a kind of liquid crystal orienting film, is formed by above-mentioned crystal aligning agent.
Another aspect of the present invention is to provide a kind of liquid crystal display element, and it includes above-mentioned liquid crystal orienting films.
Crystal aligning agent
Polymer (A)
Polymer (A) of the invention is to react gained with diamines component (b) by tetracarboxylic dianhydride's component (a).
The preferred embodiment of above-mentioned polymer (A) is that polyamic acid polymer, polyimide polymer, polyimides system are embedding
Section co-polymer or these combination.Wherein, the preferred embodiment of polyimides system block copolymer is polyamic acid block
Co-polymer, polyimide block co-polymer, polyamic acid-polyimide block co-polymer, or in which combination.
Tetracarboxylic dianhydride's component (a)
Tetracarboxylic dianhydride's compound (a-1)
Tetracarboxylic dianhydride's component (a) of the invention can include at least tetracarboxylic dianhydride's compound (a-1), have such as following formula
(3) structure shown in.
In above formula (3), E1、E2、E3And E4It is each independently hydrogen atom, the alkyl that carbon number is 1 to 6, carbon number are 2 to 6
Alkenyl or alkynyl or phenyl, and E1、E2、E3And E4It can be identical or different.
In E1、E2、E3And E4In the case where with steric hindrance structure, the LCD alignment of crystal aligning agent will cause not
It is good.Therefore, E1、E2、E3And E4Preferably hydrogen atom, methyl or ethyl, wherein being again more preferably with methyl.
The specific example of tetracarboxylic dianhydride's compound (a-1) of structure shown in above formula (3) may be, for example, following formula (3-1) to formula
(3-5) compound represented.It is preferable with formula (3-1) and formula (3-2) for LCD alignment, and is more with formula (3-2)
It is good.
Total usage amount based on tetracarboxylic dianhydride's component (a) is 100 moles, the use of tetracarboxylic dianhydride's compound (a-1)
Amount is 20 to 100 moles, and preferably 30 to 90 moles, be so more preferably with 40 to 80 moles.
Other tetracarboxylic dianhydride's compounds (a-2)
Tetracarboxylic dianhydride's component (a) according to the present invention can further include other tetracarboxylic dianhydride's compounds (a-2).Its
His tetracarboxylic dianhydride's compound (a-2) preferred embodiment is (1) aliphatic tetracarboxylic dianhydride compound, (2) Alicyclic tetracarboxylic acid
The tetracarboxylic dianhydride's chemical combination of dianhydride compound, (3) aromatic tetracarboxylic dianhydride compound or (4) with formula (4-1) to formula (4-6)
Object etc..
(1) aliphatic tetracarboxylic dianhydride compound according to the present invention is including but not limited to ethane tetracarboxylic dianhydride or butane
Aliphatic tetracarboxylic dianhydride's compound of tetracarboxylic dianhydride etc..
(2) Alicyclic tetracarboxylic acid dianhydride compound according to the present invention is including but not limited to 1,2,3,4- cyclobutane tetrabasic carboxylic acid
Dianhydride, 1,2- dimethyl -1,2,3,4- cyclobutane tetracarboxylic dianhydride, 1,3- dimethyl -1,2,3,4- cyclobutane tetracarboxylic dianhydride,
The chloro- 1,2,3,4- cyclobutane tetracarboxylic dianhydride of 1,3- bis-, 1,2,3,4- tetramethyl -1,2,3,4- cyclobutane tetracarboxylic dianhydride, 1,
2,3,4- pentamethylene tetracarboxylic dianhydride, 1,2,4,5- cyclopentanetetracarboxylic dianhydride, 3,3', 4,4'- dicyclohexyl tetracarboxylic dianhydride,
Cis- 3,7- dibutyl suberyl -1,5- diene -1,2,5,6- tetracarboxylic dianhydride, 2,3,5- tricarboxylic cyclopentyl acetic acid dianhydride or
The Alicyclic tetracarboxylic acid dianhydride compound of two rings [2.2.2]-octyl- 7- alkene -2,3,5,6- tetracarboxylic dianhydride etc..
The concrete example of (3) aromatic tetracarboxylic dianhydride compound according to the present invention may include, but are not limited to 3,4- dicarboxyl
Base -1,2,3,4- naphthane -1- amber acid dianhydride, the equal tetracarboxylic dianhydride of benzene, 2,2', 3,3'- benzophenone tetracarboxylic dianhydride, 3,
3', 4,4'- benzophenone tetracarboxylic dianhydride, 3,3', 4,4'- biphenyl sulfone tetracarboxylic dianhydride, 1,4,5,8- naphthalene tetracarboxylic acid dianhydride, 2,
3,6,7- naphthalene tetracarboxylic acid dianhydride, 3,3'-4,4'- diphenylethane tetracarboxylic dianhydride, 3,3', 4,4'- dimethyl diphenyl silane
Tetracarboxylic dianhydride, 3,3', 4,4'- tetraphenyl silane tetracarboxylic dianhydride, 1,2,3,4- furans tetracarboxylic dianhydride, 2,3,3', 4'- bis-
Phenylate tetracarboxylic dianhydride, 3,3', bis- (3,4- di carboxyl phenyloxy) diphenyl sulfides two of 4,4'- diphenyl ether tetracarboxylic dianhydride, 4,4'-
Acid anhydride, 2,3,3', 4'- diphenyl sulfide tetracarboxylic dianhydride, 3,3', 4,4'- diphenyl sulfide tetracarboxylic dianhydride, bis- (the 3,4- dicarboxyls of 4,4'-
Phenoxyl) diphenyl sulfone dianhydride, 4,4'- bis- (3,4- di carboxyl phenyloxy) diphenyl propane dianhydrides, 3,3', the different Asia of 4,4'- perfluor
Two phthalic acid dianhydride of propyl, 2,2', 3,3'- biphenyltetracaboxylic dianhydride, 2,3,3', 4'- biphenyltetracaboxylic dianhydride, 3,3',
4,4'- biphenyltetracaboxylic dianhydride, bis- (phthalic acid) phosphniline oxide dianhydrides, bis- (the triphenylbenzene diacid) two of p- phenylene-
Bis- (triphenylbenzene diacid) dianhydrides of acid anhydride, m- phenylene -, bis- (triphenylbenzene diacid) -4,4'- diphenyl ether dianhydrides, bis- (triphens
Base phthalic acid) -4,4'- diphenyl methane dianhydride, ethylene glycol-bis- (dehydration trimellitates), propylene glycol-is bis- (is dehydrated inclined benzene three
Acid esters), 1,4- butanediol-bis- (dehydration trimellitate), 1,6-HD-bis- (dehydration trimellitates), 1,8- ethohexadiol-
Bis- (dehydration trimellitates), bis- (4- hydroxyphenyl) propane-of 2,2- bis- (dehydration trimellitates), 2,3,4,5- tetrahydrofuran four
Carboxylic acid dianhydride, 1,3,3a, 4,5,9b- hexahydro -5- (two side oxygroup -3- furyl of tetrahydro -2,5-)-naphtho- [1,2-c]-furans -
1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -5- methyl -5- (two side oxygroup -3- furyl of tetrahydro -2,5-)-naphtho- [1,2-
C]-furans -1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -5- ethyl -5- (two side oxygroup -3- furyl of tetrahydro -2,5-)-naphthalene
And [1,2-c]-furans -1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -7- methyl -5- (two side oxygroup -3- furans of tetrahydro -2,5-
Base)-naphtho- [1,2-c]-furans -1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -7- ethyl -5- (two side oxygroup of tetrahydro -2,5- -
3- furyl)-naphtho- [1,2-c]-furans -1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -8- methyl -5- (tetrahydro -2,5- two
Side oxygroup -3- furyl)-naphtho- [1,2-c]-furans -1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -8- ethyl -5- (tetrahydro -
Bis- side oxygroup -3- furyl of 2,5-)-naphtho- [1,2-c]-furans -1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -5,8- diformazan
Base -5- (two side oxygroup -3- furyl of tetrahydro -2,5-)-naphtho- [1,2-c]-furans -1,3- diketone, 5- (bis- side oxygroup four of 2,5-
Hydrogen furyl) -3- methyl -3- cyclohexene -1,2- dicarboxylic acid dianhydride etc..
Tetracarboxylic dianhydride's compound shown in (4) formula (4-1) to formula (4-6) according to the present invention, is described below in detail.
In formula (4-5), A1Indicate the bivalent group containing aromatic rings；R indicates 1 to 2 integer；A2And A3It can be identical
Or it is different, and each can represent hydrogen atom or alkyl.Preferably, tetracarboxylic dianhydride's compound as shown in formula (4-5) can be selected from
In such as following formula (4-5-1) to formula (4-5-3) compound represented.
In formula (4-6), A4Represent the bivalent group containing aromatic rings；A5And A6Can be to be identical or different, and respectively generation
Table hydrogen atom or alkyl.Preferably, tetracarboxylic dianhydride's compound as shown in formula (4-6) can be selected from such as following formula (4-6-1) institute
The compound shown.
Above-mentioned tetracarboxylic dianhydride's component (a) individually a kind of can use or mix a variety of uses.
Total usage amount based on tetracarboxylic dianhydride's component (a) is 100 moles, other tetracarboxylic dianhydride's compounds (a-2)
Usage amount is 0~80 to mole, and preferably 10 to 70 moles, be so more preferably with 20 to 60 moles.
Usage amount based on diamines component (b) is 100 moles, and tetracarboxylic dianhydride's component (a) usage amount range is 20 to 200
Mole；Preferably 30 to 120 moles.
Diamines component (b)
Diamine compound (b-1)
Diamines component (b) of the invention includes at least the diamine compound (b-1) of the structure with following formula (1).
In formula (1), L1Respectively independently indicate the alkoxy, acetamide that alkyl, carbon number that carbon number is 1 to 10 are 1 to 10
Base, fluorine atom, chlorine atom or bromine atom；L2It is respectively independent to indicate that carbon number is 1 to 3 alkyl；X representative-O- ,-S- ,-CO- ,-C
(CH3)2-、-C(CF3)2Or the alkylidene that carbon number is 1 to 3；And m respectively independently indicates 0 to 3 integer；N indicates 0 to 4
Integer.
In one embodiment, the X of above formula (1) is preferably-O- ,-S- or-CO-.
Specifically, the diamine compound (b-1) of the above-mentioned structure with following formula (1) may be, for example, following formula (1-1) to formula
(1-27) compound represented.
Total usage amount based on diamines component (b) is 100 moles, and the usage amount of diamine compound (b-1) is rubbed for 2 to 20
You, preferably 3 to 15 moles, so with 4 to 10 moles for more preferably.
If diamine compound (b-1) is not used in crystal aligning agent, then the charge for being formed by liquid crystal display element disappears
Except light resistance is bad.
In addition, the charge elimination that can further promote obtained liquid crystal display element is resistance to if X is-O- ,-S- or-CO-
Photosensitiveness.
Other diamine compounds (b-2)
Diamines component (b) of the invention can further include other diamine compounds (b-2).
Other diamine compounds (b-2) may include, but are not limited to 1,2- diaminoethanes, 1,3- diaminopropanes, 1,4- bis-
Butylamine, 1,5- 1,5-DAP, 1,6- diamino hexane, 1,7- diaminoheptane, 1,8- diamino-octane, 1,9- diamino
Base nonane, 1,10- diamino decane, 4,4'- diaminoheptane, 1,3- diamino -2,2- dimethylpropane, 1,6- diamino -
2,5- dimethylhexane, 1,7- diamino -2,5- dimethyl heptane, 1,7- diamino -4,4- dimethyl heptane, 1,7- diamino
Base -3- methyl heptane, 1,9- diamino -5- methylnonane, 2,11- diamino dodecane, 1,12- diamino octadecane, 1,2-
Bis- (3- amino propoxyl group) ethane, 4,4'- diamino-dicyclohexyl methane, 4,4'- diamino -3,3'- dimethyidicyclohexyl
Amine, 1,3- diaminocyclohexane, 1,4- diaminocyclohexane, isophorone diamine, tetrahydro bicyclopentadiene diamines, tricyclic
(6.2.1.02,7)-endecatylene dimethyl-p-phenylenediamine, 4,4' methylene bis (cyclo-hexylamine), 4,4'- diamino-diphenyl first
Alkane, 4,4'- diamino-diphenyl ethane, 4,4'- diamino diphenyl sulfone, 4,4'- diaminobenzene formailide, 4,4'- diamino
Base diphenyl ether, 3,4'- diamino-diphenyl ether, 1,5- diaminonaphthalene, 5- amino -1- (4'- aminophenyl) -1,3,3- front three
Base hydrogen indenes, 6- amino -1- (4'- aminophenyl) -1,3,3- trimethyl hydrogen indenes, hexahydro -4,7- first bridge time hydrogen indenyl dimethylene
Bis- [4- (the 4- of diamines, 3,3'- diaminobenzophenone, 3,4'- diaminobenzophenone, 4,4'- diaminobenzophenone, 2,2-
Amino-benzene oxygen) phenyl] propane, bis- [4- (4- amino-benzene oxygen) phenyl] hexafluoropropane of 2,2-, 2,2- bis- (4- aminophenyls)
Bis- [4- (4- amino-benzene oxygen) phenyl] sulfones of hexafluoropropane, 2,2-, bis- (4- amino-benzene oxygen) hexamethylenes of 1,4-, the bis- (4- of 1,5-
Amino-benzene oxygen methylene) adamantane, bis- (4- amino-benzene oxygen) benzene of 1,4-, bis- (4- amino-benzene oxygen) benzene of 1,3-, 1,3- be bis-
Bis- (4- the aminophenyl) -10- hydrogen anthracenes of (3- amino-benzene oxygen) benzene, 9,9-, bis- (4- aminophenyl) anthracene [9,10-bis (4- of 9,10-
Aminophenyl) anthracene], bis- (4- aminophenyl) Fluorene, 4,4'- methylene-bis- (the 2- chlorine of 2,7- diamino Fluorene, 9,9-
Aniline), 4,4'- (p- phenylene isopropylidene) dianil, 4,4'- (m- phenylene isopropylidene) dianil, 2,2'- it is bis-
[4- (4- amino -2- 4-trifluoromethylphenopendant) phenyl] hexafluoropropane, 4,4'- bis- [(4- amino -2- trifluoromethyl) phenoxy groups] -
Octafluorobiphenyl, 5- [4- (4- pentane butylcyclohexyl) cyclohexyl] phenylmethylene -1,3- diaminobenzene { 5- [4- (4-n-
Pentylcyclohexyl) cyclohexyl] phenylmethylene-1,3-diaminobenzene, the bis- [4- (4- of 1,1-
Amino-benzene oxygen) phenyl] -4- (4- ethylphenyl) hexamethylene { 1,1-bis [4- (4-aminophenoxy) phenyl] -4- (4-
Ethyl phenyl) cyclohexane } or other diamine compounds as shown in following formula (5-1) to formula (5-29).
In formula (5-1), X6It represents And X7Represent group containing steroid, trifluoromethyl, fluorine-based, carbon number as 2 to 30 alkyl or spread out
It is born from the univalent perssad of the nitrogen atoms cyclic structure such as pyridine, pyrimidine, triazine, piperidines and piperazine.
Other diamine compounds shown in above formula (5-1) preferably can be 2,4- diamino-phenyl Ethyl formate (2,4-
Diaminophenyl ethyl formate), 3,5- diamino-phenyl Ethyl formate (3,5-diaminophenyl ethyl
Formate), 2,4- diamino-phenyl propyl formate (2,4-diaminophenyl propyl formate), 3,5- diamino
Phenyl propyl formate (3,5-diaminophenyl propyl formate), 1- dodecyloxy -2,4- diaminobenzene (1-
Dodecoxy-2,4-diamino-benzene), 1- hexadecane epoxide -2,4- diaminobenzene (1-hexadecoxy-2,4-
Diaminobenzene), 1- octadecane epoxide -2,4- diaminobenzene (1-octadecoxy-2,4-diaminobenzene) or
Other diamine compounds shown in following formula (5-1-1) to formula (5-1-6).
In formula (5-2), X8It represents X9And X10Indicate time aliphatic ring, secondary aromatic ring or secondary heterocyclic group, and X11Represent carbon
Fluoroalkyloxy that fluoroalkyl that alkoxy that alkyl that number is 3 to 18, carbon number are 3 to 18, carbon number are 1 to 5, carbon number are 1 to 5,
Cyano or halogen atom.
Other diamine compounds shown in above formula (5-2) preferably can be for as shown in following formula (5-2-1) to formula (5-2-13)
Diamine compound:
In formula (5-2-10) into formula (5-2-13), s can represent 3 to 12 integer.
In formula (5-3), X12Represent hydrogen atom, carbon number as 1 to 5 acyl group, carbon number as 1 to 5 alkyl, carbon number be 1 to 5
Alkoxy or halogen.X13For integer of 1 to 3.Work as X13When greater than 1, multiple X12It can be identical or different.
Diamine compound shown in above-mentioned formula (5-3) is preferably selected from (1) X13Be 1: p-phenylenediamine, m- phenylenediamine,
Ortho-phenylene diamine or 2,5- diaminotoluene etc.；(2)X13For 2:4,4'- benzidine, 2,2'- dimethyl -4,4'- diamino
Biphenyl, 3,3'- dimethyl -4,4'- benzidine, 3,3'- dimethoxy-4 ', 4'- benzidine, 2,2'- bis- chloro- 4,
4'- benzidine, the chloro- 4,4'- benzidine of 3,3'- bis-, 2,2', the chloro- 4,4'- benzidine of 5,5'- tetra-, 2,2'-
Two chloro- 4,4'- diamino -5,5'- dimethoxy-biphenyls or bis- (trifluoromethyl) biphenyl of 4,4'- diamino -2,2'- etc.；(3)X13
For 3:1, bis- (4'- aminophenyl) benzene of 4- etc. are more preferably selected from p-phenylenediamine, 2,5- diaminotoluene, 4,4'- diamino
Biphenyl, 3,3'- dimethoxy-4 ', 4'- benzidine or bis- (4'- aminophenyl) benzene of 1,4-.
In formula (5-4), X14Represent 1 to 5 integer.The formula (5-4) is preferably selected from 4,4'- diamino-diphenyl sulphur
Ether.
In formula (5-5), X15And X17It can be identical or different, and respectively represent bivalent organic group, X16Representative is derived from
The bivalent group of the nitrogen atoms cyclic structure such as pyridine, pyrimidine, triazine, piperidines and piperazine.
In formula (5-6), X18、X19、X20And X21It respectively can be identical or different, and carbon number can be represented as 1 to 12 hydrocarbon
Base.X22Represent integer of 1 to 3, and X23Represent integer of 1 to 20.
In formula (5-7), X24Representative-O- or secondary cyclohexyl, X25Representative-CH2, X26Represent phenylene or secondary hexamethylene
Base, and X27Represent hydrogen atom or heptyl.
Diamine compound shown in above-mentioned formula (5-7) is preferably selected from two as shown in following formula (5-7-1) and formula (5-7-2)
Amine compounds.
Other diamine compounds shown in formula (5-8) to formula (5-29) are as follows:
In formula (5-16) into formula (5-19), X28The alkoxy that the alkyl or carbon number for being 1 to 10 with carbon number are 1 to 10 be compared with
It is good.In formula (5-20) into formula (5-24), X29The alkoxy that the alkyl or carbon number for being 1 to 10 with hydrogen atom, carbon number are 1 to 10 is
Preferably.
Other diamine compounds (b-2) preferably may include, but are not limited to 1,2- diaminoethanes, two hexamethylene of 4,4'- diamino
Methylmethane, 4,4'- diaminodiphenyl-methane, 4,4'- diamino-diphenyl ether, 5- [4- (4- pentane butylcyclohexyl) hexamethylene
Base] phenylmethylene -1,3- diaminobenzene, bis- [4- (4- amino-benzene oxygen) phenyl] -4- (4- ethylphenyl) hexamethylenes of 1,1-,
2,4- diamino-phenyl Ethyl formate, p-phenylenediamine, m- phenylenediamine, ortho-phenylene diamine, formula (5-1-1), formula (5-1-2), formula
Compound represented by (5-1-5), formula (5-2-1), formula (5-2-11), formula (5-7-1), formula (5-25) or formula (5-28).
Diamine compound in diamines component (b) above-mentioned can the individually a kind of or a variety of uses of mixing.
Total usage amount based on diamines component (b) is 100 moles, the usage amounts of other diamine compounds (b-2) be 80 to
98 moles, preferably 85 to 97 moles, so with 90 to 96 moles for more preferably.
The manufacturing method of polymer (A)
The preparation of polyamic acid polymer according to the present invention can be general method, preferably, the polyamic acid polymerize
It will include that tetracarboxylic dianhydride's component (a) and the mixture of diamines component (b) are dissolved in solvent that the preparation method of object, which comprises the steps of:,
In, polycondensation reaction is carried out under the conditions of 0 DEG C to 100 DEG C of temperature and is reacted 1 hour to 24 hours, then again by above-mentioned reaction
Polyamic acid polymer can be obtained in such a way that evaporator carries out vacuum distillation in solution, or above-mentioned reaction solution is poured into
In a large amount of lean solvent, a precipitate is obtained, then the precipitate is dried via the mode that is dried under reduced pressure, can be obtained
To polyamic acid polymer.
Can be identical or different with the solvent in following crystal aligning agents for the solvent in polycondensation reaction, and it is anti-for polycondensation
Solvent in answering is not particularly limited, as long as can dissolve reactant and product.Preferably, solvent includes but unlimited
In (1) non-proton system's polar solvent, such as: n-methyl-2-pyrrolidone (N-methyl-2-pyrrolidinone；NMP),N,
N- dimethyl acetamide, N,N-dimethylformamide, dimethyl sulfoxide, gamma-butyrolacton, 4-methyl urea or hexamethyl tricresyl phosphate
Non-proton system's polar solvent of amine etc.；(2) phenol system solvent, such as: the phenol system of m-cresol, dimethlbenzene, phenol or halogenated phenols etc.
Solvent.Usage amount based on mixture is 100 parts by weight, and the usage amount for the solvent in polycondensation reaction is preferably 200 weight
Part to 2000 parts by weight, more preferably 300 parts by weight to 1800 parts by weight.
Particularly, in polycondensation reaction, solvent can and with suitable lean solvent, wherein lean solvent not will cause polyamic acid
Polymer is precipitated.Lean solvent individually a kind of use or can mix a variety of uses, and it includes but be not limited to (1) alcohols, example
Such as: methanol, ethyl alcohol, isopropanol, cyclohexanol, ethylene glycol, propylene glycol, 1,4- butanediol or triethylene glycol alcohols；(2) ketone
Class, such as: the ketone of acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), cyclohexanone etc.；(3) esters, such as: methyl acetate, vinegar
The esters of acetoacetic ester, butyl acetate, diethy-aceto oxalate, diethyl malonate or glycol ethyl ether acetate etc.；(4) ethers,
Such as: Anaesthetie Ether, Ethylene glycol methyl ether, glycol ethyl ether, ethylene glycol n-propyl ether, ethylene glycol isopropyl ether, ethylene glycol
The ethers of n-butyl ether, ethylene glycol dimethyl ether or diethylene glycol dimethyl ether etc.；(5) halogenated hydrocarbons, such as: methylene chloride,
The halogenated hydrocarbons of 1,2- dichloroethanes, 1,4- dichloroetane, trichloroethanes, chlorobenzene or o-dichlorobenzene etc.；(6) hydro carbons, such as:
Any combination of the hydro carbons of tetrahydrofuran, hexane, heptane, octane, benzene, toluene or dimethylbenzene etc. or above-mentioned solvent.Based on diamines
The usage amount of component (b) is 100 parts by weight, and the dosage of lean solvent is preferably 0 parts by weight to 60 parts by weight, more preferably 0 parts by weight
To 50 parts by weight.
The preparation of polyimide polymer according to the present invention can be general method, preferably, polyimide polymer
Preparation method first a mixture is dissolved in solution, wherein mixture includes tetracarboxylic dianhydride's component (a) and diamines component
(b), and polymerization reaction is carried out, to form polyamic acid polymer.Then, in the presence of dehydrating agent and catalyst, further
Heating, and dehydration closed-loop reaction is carried out, so that the amide acid functional group in polyamic acid polymer turns via dehydration closed-loop reaction
Become acid imide functional group (i.e. imidizate), and obtains polyimide polymer.
Can be identical as the solvent in following crystal aligning agents for the solvent in dehydration closed-loop reaction, therefore do not repeat separately.Base
It is 100 parts by weight in the usage amount of polyamic acid polymer, the usage amount for the solvent in dehydration closed-loop reaction is preferably 200
Parts by weight are to 2000 parts by weight, more preferably 300 parts by weight to 1800 parts by weight.
For the degree of imidisation for obtaining preferable polyamic acid polymer, the operation temperature of dehydration closed-loop reaction is preferably
40 DEG C to 200 DEG C, more preferably 40 DEG C to 150 DEG C.If the operation temperature of dehydration closed-loop reaction be lower than 40 DEG C, imidizate it is anti-
Not exclusively, and the degree of imidisation of polyamic acid polymer should be reduced.However, if the operation temperature of dehydration closed-loop reaction is higher than
At 200 DEG C, the weight average molecular weight of resulting polyimide polymer is relatively low.
It can be selected from anhydride compound for the dehydrating agent in dehydration closed-loop reaction, specifically for example: acetic anhydride, propionic acid
The anhydride compound of acid anhydride or trifluoro-acetic anhydride etc..It is 1 mole based on polyamic acid polymer, the usage amount of dehydrating agent is 0.01
Mole to 20 moles.It can be selected from (1) pyridine compounds and their for the catalyst in dehydration closed-loop reaction, such as: pyridine, front three
The pyridine compounds and their of yl pyridines or lutidines etc.；(2) three-level aminated compounds, such as: the tertiary amine of triethylamine etc.
Class compound.Usage amount based on dehydrating agent is 1 mole, and the usage amount of catalyst is 0.5 mole to 10 moles.
The preferred embodiment of polyimides system according to the present invention block copolymer be polyamic acid block copolymer,
Polyimide block co-polymer, polyamic acid-polyimide block co-polymer or these any combination.
The preparation of polyimides system according to the present invention block copolymer can be general method, preferably, polyamides is sub-
One starting material is first dissolved in solvent by the preparation method of amine system block copolymer, and carries out polycondensation reaction, wherein described rise
Beginning object includes above-mentioned at least one polyamic acid polymer and/or above-mentioned at least one polyimide polymer, and can be into
It include one step tetracarboxylic dianhydride's component (a) and diamines component (b).
Tetracarboxylic dianhydride's component (a) in the starting material with diamines component (b) is polymerize with the above-mentioned polyamic acid for preparing
Tetracarboxylic dianhydride's component (a) used in object is identical as diamines component (b), and for the solvent in polycondensation reaction can with it is following
Solvent in crystal aligning agent is identical, does not repeat separately herein.
Usage amount based on starting material is 100 parts by weight, and the usage amount for the solvent in polycondensation reaction is preferably 200 weights
Part is measured to 2000 parts by weight, more preferably 300 parts by weight to 1800 parts by weight.The operation temperature of polycondensation reaction is preferably 0 DEG C to 200
DEG C, more preferably 0 DEG C to 100 DEG C.
Preferably, starting material is including but not limited to (1) two kind of polyamic acid polymer that terminal groups are different and structure is different；
(2) two kinds of polyimide polymers that terminal groups are different and structure is different；(3) polyamic acid that terminal groups are different and structure is different
Polymer and polyimide polymer；(4) polyamic acid polymer, tetracarboxylic dianhydride's compound and diamine compound, wherein four
Carboxylic acid dianhydride compound and diamine compound at least one of with form tetrabasic carboxylic acid two used in polyamic acid polymer
The structure of acid anhydride component (a) and diamines component (b) is different；(5) polyimide polymer, tetracarboxylic dianhydride's compound and two amine compounds
Object, wherein at least one of tetracarboxylic dianhydride's compound and diamine compound are made with polyimide polymer is formed
The structure of tetracarboxylic dianhydride's component (a) and diamines component (b) is different；(6) polyamic acid polymer, polyimides polymerization
Object, tetracarboxylic dianhydride's compound and diamine compound, wherein at least one of tetracarboxylic dianhydride's compound and diamines and formation
The structure phase of tetracarboxylic dianhydride's component (a) used in polyamic acid polymer or polyimide polymer and diamines component (b)
It is different；(7) two kinds of different polyamic acid polymers of structure, tetracarboxylic dianhydride's compound and diamine compound；(8) two kinds of structure phases
Different polyimide polymer, tetracarboxylic dianhydride's compound and diamine compound；(9) two kinds of terminal groups are anhydride group and structure phase
Different polyamic acid polymer and diamine compound；(10) two kinds of terminal groups are amino and the different polyamic acid polymerization of structure
Object and tetracarboxylic dianhydride's compound；(11) two kinds of terminal groups are anhydride group and the different polyimide polymer and two of structure
Amine compounds；(12) two kinds of terminal groups are amino and the different polyimide polymer and tetracarboxylic dianhydride's compound of structure.
Do not influencing within the scope of effect of the invention, preferably, the polyamic acid polymer, the polyimide polymer with
And the polyimides system block copolymer can be the end modified type polymer first carried out after molecular-weight adjusting.By using
The polymer of end modified type can improve the coating performance of crystal aligning agent.The mode for preparing the end modified type polymer can
By while polyamic acid polymer carries out polycondensation reaction, monofunctional compounds are added and are made, mono-functionalization
Object is closed including but not limited to (1) unitary acid anhydrides, such as: maleic anhydride, phthalic anhydride, itaconic anhydride, positive decyl succinic acid
The unitary acid anhydrides of acid anhydride, dodecyl succinic anhydride, n-tetradecane base succinic anhydride or N-hexadecyl succinic anhydride etc.；(2)
Monoamine compound, such as: aniline, cyclohexylamine, n-butylamine, n-amylamine, n-hexylamine, positive heptyl amice, n-octyl amine, positive nonyl amine, n-Decylamine,
N-undecane amine, n-dodecane amine, n-tridecane amine, n-tetradecane amine, n-pentadecane amine, hexadecane amine, n-heptadecane amine,
The monoamine compound of n-octadecane amine or n-eicosane amine etc.；(3) monoisocyanate compound, such as: phenyl isocyanate is different
The monoisocyanate compound of cyanic acid naphthalene ester etc..
The weight average that polymer (A) of the invention converts according to measured by gel permeation chromatography through polystyrene
Molecular weight is 10,000 to 90,000, preferably 12,000 to 75,000, more preferably 15,000 to 60,000.
Solvent (B)
Solvent used in crystal aligning agent of the invention is not particularly limited, as long as soluble polymeric object (A)
It is reacted with any other composition and not generated with it, preferably with solvent used in aforementioned synthesizing polyamides acid,
Meanwhile also can and with used lean solvent when synthesizing the polyamic acid.
The concrete example of solvent (B) include but is not limited to n-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone,
NMP), gamma-butyrolacton, butyrolactam, 4- hydroxy-4-methyl-2-pentanone, ethylene glycol single methyl ether, butyl lactate, acetic acid
Butyl ester, methoxy methyl propionate, ethoxyl ethyl propionate, Ethylene glycol methyl ether, glycol ethyl ether, ethylene glycol n-propyl ether,
Ethylene glycol isopropyl ether, ethylene glycol n-butyl ether (ethylene glycol n-butyl ether), ethylene glycol dimethyl ether,
Ethylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethyl two
Alcohol list ethylether, diethylene glycol monomethyl ether acetic acid esters, diethylene glycol monoethyl ether acetic acid esters or N,N-dimethylformamide or
DMAC N,N' dimethyl acetamide (N, N-dimethyl acetamide) etc..Solvent (B) can be used alone or combine a variety of next
It uses.
Usage amount based on polymer (A) is 100 parts by weight, and the usage amount of solvent (B) is 800 to 4000 parts by weight, compared with
Good is 900 to 3500 parts by weight, and more preferably 1000 to 3000 parts by weight.
Additive (C)
Carboxylic acid compound (c-1)
Carboxylic acid compound (c-1) is included at least in the additive (C) of crystal aligning agent of the invention.
Carboxylic acid compound (c-1) has the structure as shown in following formula (2).
In formula (2), R1The alkylidene for being 1 to 6 for singly-bound or carbon number；R2To R6Be each independently hydrogen atom, hydroxyl ,-
Naphthenic base that alkynyl that alkenyl that alkyl that Y-COOH, carbon number are 1 to 6, carbon number are 2 to 6, carbon number are 2 to 6, carbon number are 3 to 7,
Aryl, COOR of the carbon number for 6 to 127、OR8Or two adjacent R2To R6Group ring is collectively formed；Y is singly-bound or carbon number is 1
To 6 alkylidene；And R7And R8The respectively alkyl of carbon number 1 to 20.
In a preferable example, the R of carboxylic acid compound (c-1)2To R6In an at least group be hydroxyl so that made
The liquid crystal display element obtained can have preferable charge to eliminate light resistance.
In another preferable example, it is based on the R of carboxylic acid compound (c-1)2To R6In an at least group be hydroxyl, on
It is ortho position or contraposition that at least one of hydroxyl, which is stated, with carboxylic acid group, so that obtained liquid crystal display element can have more preferably charge
Eliminate light resistance.
In another preferable example, the R of carboxylic acid compound (c-1)1For singly-bound, so that obtained liquid crystal display element
There can be more preferably charge to eliminate light resistance.
Specifically, carboxylic acid compound (c-1) may include but be not limited to compound as follows.
In a preferable example, carboxylic acid compound (c-1) may include 2- hexyl -6- hydroxybenzoic acid, salicylic acid, 4- hydroxyl
Base benzoic acid, 6- cresotinic acid, 3- cresotinic acid, thymotic acid, 2,3- dihydroxy benzoic acid, 3,4- dihydroxy
Benzoic acid, 1,4- dihydroxy benzoic acid, 3- methoxysalicylic acid, 4- methoxysalicylic acid, vanillic acid, gallic acid, 2,
3,4- trihydroxy benzoic acid, 2,3,6- trihydroxy benzoic acid, 2,4,5- trihydroxy benzoic acid, 3-O- methyl gallic acid
Or syringic acid.
Above-mentioned cited carboxylic acid compound (c-1) may be used alone or in combination a variety of uses.
Usage amount based on polymer (A) is 100 parts by weight, and the usage amount of carboxylic acid compound (c-1) is 3 parts by weight to 30
Parts by weight, preferably 4 parts by weight are so more preferably with 5 parts by weight to 20 parts by weight to 25 parts by weight.If being free of in crystal aligning agent
Carboxylic acid compound (c-1), then the charge elimination light resistance for being formed by liquid crystal display element are bad.
Other additives (c-2)
It influencing within the scope of effect of the invention, additive (C) is selectively included other additives (c-2), and
Other additives (c-2) are epoxide or the silane compound with functional groups etc..The work of other additives (c-2)
With being adhesion for improving the liquid crystal orienting film and substrate surface.Other additives (c-2) can individually it is a kind of use or
Person mixes a variety of uses.
Epoxide above-mentioned may include, but are not limited to ethylene glycol bisglycidyl ethers, polyethylene glycol diepoxy propyl
Ether, propylene glycol bisglycidyl ethers, tripropylene glycol bisglycidyl ethers, polypropylene glycol bisglycidyl ethers, two ring of neopentyl glycol
Oxygen propyl group ether, 1,6-HD bisglycidyl ethers, glycerine bisglycidyl ethers, 2,2- dibromoneopentyl glycol diepoxy propyl
Ether, tetra- glycidyl -2,4- hexylene glycol of 1,3,5,6-, N, N, N', tetra- glycidyl of N'--m-xylenedimaine, 1,3- it is bis- (N,
N- diepoxy propylcarbamic methyl) hexamethylene, N, N, N', tetra- glycidyl -4,4'- diaminodiphenyl-methane of N'-, N, N- ring
The p- glycidoxy aniline of oxygen propyl group-, 3- (N- allyl-N- glycidyl) TSL 8330,3- (N, N-
Diepoxy propyl) TSL 8330 etc..
Usage amount based on polymer (A) be 100 parts by weight, the usage amount of epoxide be generally 40 parts by weight with
Under, preferably 0.1 parts by weight to 30 parts by weight.
The above-mentioned silane compound with functional groups may include, but are not limited to 3- TSL 8330,3-
Aminopropyltriethoxywerene werene, 2- TSL 8330,2- aminopropyltriethoxywerene werene, N- (2- amino
Ethyl) -3- TSL 8330, N- (2- amino-ethyl) -3- aminopropylmethyldimethoxysilane, 3- urea groups
Propyl trimethoxy silicane (3-ureidopropyltrimethoxysilane), 3- ureidopropyltriethoxysilane, N- second
Epoxide carbonyl -3- TSL 8330, N- ethoxy carbonyl -3-aminopropyltriethoxysilane, tri- ethoxy of N-
Base silane base propyl second triamine, N- trimethoxysilylpropyl second triamine, 10- trimethoxy silane base -1,4 three times three times,
Tri- a word used for translation decane of 7-, three a word used for translation decane of 10- triethoxysilicane alkyl -1,4,7-, two a word used for translation nonyl acetic acid of 9- trimethoxy silane base -3,6-
Ester, two a word used for translation nonyl acetate of 9- triethoxysilicane alkyl -3,6-, N- benzyl -3- TSL 8330, N- benzene first
Base -3-aminopropyltriethoxysilane, N- phenyl -3- TSL 8330, three second of N- phenyl -3- aminopropyl
Bis- three second of (ethylene oxide) -3- aminopropyl of bis- (the ethylene oxide) -3- TSL 8330s of oxysilane, N-, N-
Oxysilane etc..
Usage amount based on polymer (A) be 100 parts by weight, the usage amount of silane compound be generally 10 parts by weight with
Under, preferably 0.5 parts by weight to 10 parts by weight.
Usage amount based on polymer (A) is 100 parts by weight, and the usage amount of additive (C) can be 3 parts by weight to 50 weight
Part, preferably 4 parts by weight to 40 parts by weight.
The preparation method of crystal aligning agent
The preparation method of crystal aligning agent of the invention is not particularly limited, and general mixed method can be used, such as first
Tetracarboxylic dianhydride's component (a) and diamines component (b) are uniformly mixed, a polymer (A) is formed with reaction.Then, by polymer
(A) solvent (B) and additive (C) is added under conditions of being 0 DEG C to 200 DEG C in temperature, dissolution is continued stirring until with agitating device
?.Preferably, solvent (B) is added in polymer (A) and additive (C) at a temperature of 20 DEG C to 60 DEG C.
The forming method of liquid crystal orienting film
Liquid crystal orienting film of the invention is that the above-mentioned crystal aligning agent that is formed by is coated on substrate, and through drying and dries
Film prepared by roasting.
The substrate that crystal aligning agent of the invention is coated with is selected from transparent material, wherein transparent material includes but unlimited
In alkali-free glass, soda-lime glass, hard glass (Pai Lesi glass), quartz glass, polyethylene pair for liquid crystal display device
Phthalic acid ester, polybutylene terepthatlate, polyether sulfone, polycarbonate etc., the ITO electrode of preferably usable liquid crystal drive
Person on substrate is had been formed on, to simplify processing procedure.Furthermore for the reflection LCD of only single sided substrate, substrate
The opaque materials such as Silicon Wafer can be used, the material of the meeting reflected light such as aluminium can be used to be formed for electrode in this case.
The coating method of crystal aligning agent of the invention can be such as method of spin coating, print process, ink-jet method.
Arbitrary temperature and time may be selected in crystal aligning agent of the invention, drying and baking processing procedure after being coated.
In general, the organic solvent contained for sufficiently removal, need to carry out drying in 1 minute to 10 minutes at 50 DEG C to 120 DEG C.It
Afterwards, baking in 5 minutes to 120 minutes is carried out at 150 DEG C to 300 DEG C.Coating thickness after baking does not have special limitation, but
Excessively thin film will cause the Reliability deterioration of liquid crystal display, therefore above-mentioned coating thickness is advisable with 5nm to 300nm, and with
10nm to 200nm is preferable.
Although crystal aligning agent of the invention can carry out known friction directional process, light orientation processing method is being used
Better effect when situation.
The concrete example of light orientation processing method can be such as: by the surface of aforementioned film, with towards the radioactive ray of specific direction polarisation
Irradiation, then optionally 150 DEG C to 250 DEG C at a temperature of heated, to assign above-mentioned film LCD alignment energy.Its
In, the ultraviolet light or visible light of the usable wavelength with 100nm to 800nm are 100nm as above-mentioned radioactive ray, and with wavelength
Ultraviolet light to 400nm is preferable, and with wavelength be 200nm to 400nm person be more preferably.It, can furthermore in order to improve LCD alignment
While heating applies ilm substrate at 50 DEG C to 250 DEG C, is irradiated with radioactive ray and apply ilm substrate.The exposure of aforementioned radioactive ray is preferable
For 1mJ/cm2To 10,000mJ/cm2, and with 100mJ/cm2To 5,000mJ/cm2For more preferably.Liquid obtained in the manner described above
Brilliant alignment film can make liquid crystal molecule with certain orientation steadily by orientation.
The manufacturing method of liquid crystal display element
The present invention provides a kind of liquid crystal display element again, and it includes liquid crystal orienting films above-mentioned.
The production method of liquid crystal display element is therefore, simply just to be stated below well known to the art person.
Refering to fig. 1, the preferred embodiment of liquid crystal display element 100 of the present invention is comprising first unit 110, second unit
120 and liquid crystal cells 130, wherein second unit 120 and first unit 110 are spaced relatively, and the setting of liquid crystal cells 130 is first
Between unit 110 and second unit 120.
First unit 110 includes first substrate 112, electrode 114 and the first liquid crystal orienting film 116, and wherein electrode 114 is with comb
The patterned mode of flute profile is formed in the surface of first substrate 112, and the first liquid crystal orienting film 116 is formed in the table of electrode 114
Face.
Second unit 120 includes the second substrate 122 and the second liquid crystal orienting film 126, wherein 126 shape of the second liquid crystal orienting film
At on the surface of the second substrate 122.
First substrate 112 and the second substrate 122 are selected from transparent material etc., wherein transparent material including but not limited to
Alkali-free glass, soda-lime glass, hard glass (Pai Lesi glass), quartz glass, polyethylene for liquid crystal display device is to benzene
Dicarboxylic acid esters, polybutylene terepthatlate, polyether sulfone, polycarbonate etc..The material of electrode 114 is selected from tin oxide
(SnO2), indium oxide-tin oxide (In2O3-SnO2) etc. transparent electrode；Or the metal electrodes such as chromium.
First liquid crystal orienting film 116 and the second liquid crystal orienting film 126 are respectively above-mentioned liquid crystal orienting film, its role is to
Liquid crystal cells 130 are made to form pre-tilt angle, and liquid crystal cells 130 can be driven by the parallel electric field that electrode 114 generates.
Liquid crystal used in liquid crystal cells 130 can be independent or mixes a variety of uses, and liquid crystal is including but not limited to diaminobenzene
Class liquid crystal, pyridazine (pyridazine) class liquid crystal, schiff base (shiff base) class liquid crystal, azoxy (azoxy) class
Liquid crystal, biphenyls liquid crystal, cyclohexylbenzene class liquid crystal, biphenyl (biphenyl) class liquid crystal, cyclohexylbenzene
(phenylcyclohexane) class liquid crystal, ester (ester) class liquid crystal, terphenyl (terphenyl), biphenyl hexamethylene
(biphenylcyclohexane) class liquid crystal, pyrimidine (pyrimidine) class liquid crystal, dioxane (dioxane) class liquid crystal, double
Cyclooctane (bicyclooctane) class liquid crystal, cubane (cubane) class liquid crystal etc., and visual demand is added again as chlorination gallbladder is solid
Alcohol (cholesteryl chloride), Cholesteryl pelargonate (cholesteryl nonanoate), cholesterol carbonic ester
The cholesterol liquid crystal of (cholesteryl carbonate) etc., or with trade name " C-15 ", " CB-15 " (Merck & Co., Inc.
Manufacture) chirality (chiral) agent etc., or decyloxy benzylidene-lures by force amino-2-methyl butyl cinnamate etc.
Electrically (ferroelectric) class liquid crystal.
Liquid crystal display element made by crystal aligning agent of the invention be suitable for various nematic liquid crystal, as TN, STN,
The liquid crystal display element of TFT, VA, IPS etc..In addition, also can be used according to selected liquid crystal and electrically or instead lure electricity by force in strong lure
The different liquid crystal display elements such as property.Liquid crystal display element in above-mentioned liquid crystal display element, especially suitable for IPS type.
It hereby is described in detail the present invention with following Examples, does not mean that present invention is limited only by disclosed in these examples only
Content.
Detailed description of the invention
For above and other purpose, feature, advantage and embodiment of the invention can be clearer and more comprehensible, appended attached drawing it is detailed
Carefully it is described as follows:
[Fig. 1] is painted the structural schematic diagram of liquid crystal display element described in an embodiment according to the present invention；
Wherein, symbol description:
100: liquid crystal display element 110: first unit
112: 114: the first conductive film of first substrate
116: the first liquid crystal orienting films 120: second unit
122: 126: the second liquid crystal orienting film of the second substrate
130: liquid crystal cells.
Specific embodiment
Synthetic polymer (A)
Synthesis example A-1-1
Nitrogen inlet, blender, condenser pipe and thermometer are set on 500 milliliters of a volume of four cervical vertebra bottles, and imported
Nitrogen.Then, the diamine compound (b-1-1), 4.86 grams as shown in formula (1-2) of 1.64 grams (0.005 mole) is added
The p-phenylenediamine (b-2-1) and 80 grams of n-methyl-2-pyrrolidone (hereinafter referred to as NMP) of (0.045 mole), and in room temperature
Lower stirring is extremely dissolved.Then, be added 9.81 grams (0.05 mole) such as formula (3-1) compound represented (a-1-1) and 20 grams
NMP, and react 2 hours at room temperature.After reaction, reaction solution is poured into 1500 milliliters of water, polymer is precipitated,
Resulting polymer is filtered, and the step of cleaning and filtering is repeated three times with methanol.Later, product is placed in vacuum drying oven
In, and be dried with temperature 60 C, it can obtain polymer (A-1-1), formula is as shown in table 1.
Synthesis example A-1-2 to A-1-10 and synthesis Comparative examples A ' -1-1
Synthesis example A-1-2 to A-1-10 and synthesis Comparative examples A ' -1-1 use the polymer (A-1-1) with synthesis example A-1-1
The identical preparation method of production method, the difference is that synthesis example A-1-2 to A-1-10 and synthesis Comparative examples A ' -1-1 change
Become the type and usage amount of raw material in polymer, formula as shown in table 1, does not repeat separately herein.
Synthesis example A-1-11
Polymer A-1-11 is prepared with the step identical as synthesis example A-1-1, wherein the type of ingredient and its usage amount phase
Together, only different place is: after mixing tetracarboxylic dianhydride's component and diamines component, the 3- methoxysalicylic of 0.49g is added
Sour (such as abbreviation C-1-1 of table 2).
Synthesis example A-2-1
Nitrogen inlet, blender, heater, condenser pipe and thermometer are set on 500 milliliters of a volume of four cervical vertebra bottles,
And import nitrogen.Then, the diamine compound (b-1-4), 5.3 as shown in formula (1-15) of 0.39 gram (0.001 mole) is added
The p-phenylenediamine (b-2-1) and 80 grams of NMP of gram (0.049 mole), and at room temperature stirring to dissolving.Then, 9.81 are added
Gram (0.05 mole) such as formula (3-1) compound represented (a-1-1) and 20 grams of NMP.After reacting 6 hours at room temperature.Reaction
After, 97 grams of NMP, 2.55 grams of acetic anhydride and 19.75 grams of pyridine is added into reaction solution above-mentioned, is warming up to 60
DEG C, and persistently stir 2 hours, to carry out imidization reaction.After reaction, reaction solution is poured into 1500 milliliters of water
In, polymer is precipitated, resulting polymer is filtered, and the step of cleaning and filtering is repeated three times with methanol.Later, will
Product is placed in vacuum drying oven, and is dried with temperature 60 C, can be obtained polymer (A-2-1), and formula is as shown in table 1.
Synthesis example A-2-2 to A-2-4 and synthesis Comparative examples A ' -2-1
Synthesis example A-2-2 to A-2-4 and synthesis Comparative examples A ' -2-1 use the polymer (A-2-1) with synthesis example A-2-1
The identical preparation method of constituent, the difference is that synthesis example A-2-2 to A-2-7 and synthesis Comparative examples A ' -2-1 change polymerization
In reaction temperature and the reaction time of the type Yu usage amount and dehydration closed-loop reaction of raw material in object, formula is as shown in table 1, herein
It does not repeat separately.
Embodiment 1
Prepare crystal aligning agent
Weigh the polymer (A-1-1) of the synthesis example A-1-1 of 100 parts by weight, the NMP of 1050 parts by weight and 3 parts by weight
3- methoxysalicylic acid, and be stirred at room temperature, it can be prepared by the crystal aligning agent of embodiment 1.
Prepare liquid crystal orienting film and liquid crystal display element
On the glass substrate by aforementioned obtained crystal aligning agent rotary coating, picture wherein is formed on the glass substrate
Plain electrode, wherein the pixel electrode be with a pair of of ITO electrode (electrode is wide: 10 μm, electrode gap: 10 μm, electrode height:
IPS driving electrode 50nm), this to ITO electrode be respectively provided with veteranellinae shape shape and mutual veteranellinae shape part be with
It separates and the mode that is engaged configures.Later, the glass substrate of crystal aligning agent is coated with dry 5 in 80 DEG C of heating plate
After minute, toasted 60 minutes in 250 DEG C of heated air circulation type baking oven, to form film thickness as the film of 100nm.
Pass through a polarizer, the ultraviolet light for being 254nm to coated surface illumination wavelength, the base for having liquid crystal orienting film is made
Plate.Next, similarly, forming film on opposite substrate and bestowing orientation processing, the opposite substrate is not have electrode shape
At but have height for the glass substrate of 4 μm of column spacer.
Above-mentioned two substrates are one group, printing and sealing agent in one wherein, and another one with liquid crystal orienting film to face
And alignment direction is both 0 ° of mode, bonding, after-hardening sealant empty structure cell is made.By this negative crystal born of the same parents to depressurize
Injection method injects liquid crystal MLC-2041 (Merck corporation), and seals inlet, as the liquid crystal display element of embodiment 1.
It is evaluated evaluation method is stated after the liquid crystal display element of embodiment 1, the results are shown in Table 2.
Embodiment 2 to 20 and comparative example 1 to 7
Embodiment 2 to 20 and comparative example 1 to 7 use preparation method identical with the crystal aligning agent of embodiment 1, difference
It is in and changes the type and usage amount of raw material in crystal aligning agent, formula and evaluation in embodiment 2 to 20 and comparative example 1 to 7
As a result it is not repeated separately herein as shown in table 2 and table 3 respectively.
Evaluation method
Charge eliminates light resistance
By using obtained by embodiment 1 to 20 and comparative example 1 to 7 through ultraviolet light orientation that illumination wavelength is 254nm
Liquid crystal display element is applied 30 minutes with 3 volts of DC voltage respectively, then with electric measurement board (TOYO
Corporation system, model Model 6254) savings voltage (V of the measurement liquid crystal display element after voltage releasingR1) and voltage
15 minutes savings voltage (V after releasingR2), savings charge, which is calculated, through lower formula (I) eliminates the gradient (VS), and according to following benchmark
It carries out evaluation charge and eliminates light resistance.Wherein, the savings charge elimination gradient after the ultraviolet light of illumination wavelength 254nm is higher, table
It is better to show that the charge of the liquid crystal display element eliminates light resistance:
It puts aside charge and eliminates the gradient
※: 75% < VS。
◎: 70% < VS≤ 75%.
Zero: 65% < VS≤ 70%.
△: 60% < VS≤ 65%.
×: VS≤ 60%.
According to table 2 and table 3, if specific diamine compound (b-1) Lai Hecheng is not used in polymer (A) in crystal aligning agent
When, it is bad that the charge of obtained liquid crystal display element eliminates light resistance.Also, if being not added with carboxylic acid compound in crystal aligning agent
(c-1) or above-mentioned carboxylic acid compound (c-1) is to come adder, obtained liquid crystal display member in polymer (A) synthesis phase
It is bad that the charge of part eliminates light resistance.
Furthermore, it when the X of used diamine compound (b-1) is-O- ,-S- or-CO-, can further be promoted
The charge of liquid crystal display element eliminates light resistance.
In addition, can further promote liquid crystal display member when having at least one hydroxyl on the phenyl ring of carboxylic acid compound (c-1)
The charge of part eliminates light resistance.Furthermore when on the phenyl ring of carboxylic acid compound (c-1) hydroxyl and carboxylic acid group be ortho position or contraposition
When, the charge that can further promote liquid crystal display element eliminates light resistance.
Although the present invention is disclosed above with several embodiments, however, it is not to limit the invention, belonging to the present invention
Any tool usually intellectual in technical field, without departing from the spirit and scope of the present invention, when can make various change with
Retouching, therefore protection scope of the present invention should be defined by the scope of the appended claims.
Claims (9)
1. a kind of crystal aligning agent, it is characterised in that include:
Polymer (A) is to react gained with diamines component (b) by tetracarboxylic dianhydride's component (a)；
Solvent (B)；And
Additive (C),
Wherein the diamines component (b) includes the diamine compound (b-1) of at least one structure with formula (1), and described is added
Adding agent (C) includes the carboxylic acid compound (c-1) of the structure as shown in following formula (2):
In formula (1), L1Respectively independently indicate the alkoxy that alkyl, carbon number that carbon number is 1 to 10 are 1 to 10, acetamido, fluorine
Atom, chlorine atom or bromine atom；L2It is respectively independent to indicate that carbon number is 1 to 3 alkyl；X representative-O- ,-S- ,-CO- ,-C
(CH3)2-、-C(CF3)2Or the alkylidene that carbon number is 1 to 3；And m respectively independently indicates 0 to 3 integer；N indicates 0 to 4
Integer,
In formula (2), R1The alkylidene for being 1 to 6 for singly-bound or carbon number；R2To R6It is each independently hydrogen atom, hydroxyl ,-Y-
Naphthenic base that alkynyl that alkenyl that alkyl that COOH, carbon number are 1 to 6, carbon number are 2 to 6, carbon number are 2 to 6, carbon number are 3 to 7, carbon
Aryl, COOR of the number for 6 to 127、OR8Or two adjacent R2To R6Group ring is collectively formed；Y is singly-bound or carbon number is 1 to 6
Alkylidene；And R7And R8The respectively alkyl of carbon number 1 to 20.
2. crystal aligning agent as described in claim 1, it is characterised in that X representative-O- ,-S- or-CO-.
3. crystal aligning agent as described in claim 1, it is characterised in that in the carboxylic acid compound (c-1), R2To R6In extremely
A few group is hydroxyl.
4. crystal aligning agent as claimed in claim 3, it is characterised in that at least one of described hydroxyl is ortho position with carboxylic acid group
Or contraposition.
5. crystal aligning agent as described in claim 1, it is characterised in that the usage amount based on the diamines component (b) is 100
Mole, the usage amount of the diamine compound (b-1) with formula (1) is 2 moles to 20 moles.
6. crystal aligning agent as described in claim 1, it is characterised in that the usage amount based on the polymer (A) is 100 weights
Part is measured, the usage amount of the carboxylic acid compound (c-1) is 3 parts by weight to 30 parts by weight.
7. crystal aligning agent as described in claim 1, it is characterised in that the usage amount based on the polymer (A) is 100 weights
Part is measured, the usage amount of the solvent (B) is 800 parts by weight to 4000 parts by weight, and the usage amount of the additive (C) is 3 weights
Part is measured to 50 parts by weight.
8. a kind of liquid crystal orienting film, it is characterised in that it is by crystal aligning agent institute according to any one of claims 1 to 7 shape
At.
9. a kind of liquid crystal display element, it is characterised in that include liquid crystal orienting film according to claim 8.
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| TW106129381A TW201912768A (en) | 2017-08-29 | 2017-08-29 | Liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element |
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| CN112852446A (en) * | 2019-11-27 | 2021-05-28 | 奇美实业股份有限公司 | Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element |
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|---|---|---|---|---|
| CN112852446A (en) * | 2019-11-27 | 2021-05-28 | 奇美实业股份有限公司 | Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element |
| CN112852446B (en) * | 2019-11-27 | 2023-11-17 | 奇美实业股份有限公司 | Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element |
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| Publication number | Publication date |
|---|---|
| TW201912768A (en) | 2019-04-01 |
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