CN109207170A - 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
- CN109207170A CN109207170A CN201810683322.9A CN201810683322A CN109207170A CN 109207170 A CN109207170 A CN 109207170A CN 201810683322 A CN201810683322 A CN 201810683322A CN 109207170 A CN109207170 A CN 109207170A
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- CN
- China
- Prior art keywords
- liquid crystal
- compound
- crystal alignment
- bis
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 140
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 58
- -1 tetracarboxylic dianhydride compound Chemical class 0.000 claims abstract description 198
- 229920000642 polymer Polymers 0.000 claims abstract description 74
- 239000002904 solvent Substances 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 230000007547 defect Effects 0.000 abstract description 13
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 67
- 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 description 61
- 150000001875 compounds Chemical class 0.000 description 60
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 53
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 48
- 239000013078 crystal Substances 0.000 description 38
- 239000002585 base Substances 0.000 description 27
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- 230000015572 biosynthetic process Effects 0.000 description 23
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- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
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- 208000005156 Dehydration Diseases 0.000 description 16
- 230000018044 dehydration Effects 0.000 description 16
- 238000006297 dehydration reaction Methods 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 125000003368 amide group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 238000006068 polycondensation reaction Methods 0.000 description 9
- 239000001294 propane Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
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- 239000000654 additive Substances 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
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- 239000001273 butane Substances 0.000 description 5
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- 230000000694 effects Effects 0.000 description 5
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- 150000002148 esters Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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- 125000005591 trimellitate group Chemical group 0.000 description 5
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- 150000001412 amines Chemical class 0.000 description 4
- GGBJHURWWWLEQH-UHFFFAOYSA-N butylcyclohexane Chemical compound CCCCC1CCCCC1 GGBJHURWWWLEQH-UHFFFAOYSA-N 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000013519 translation Methods 0.000 description 4
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 3
- SXWIAEOZZQADEY-UHFFFAOYSA-N 1,3,5-triphenylbenzene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1 SXWIAEOZZQADEY-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- HYBVISCYJVVEDX-UHFFFAOYSA-N 4-(4-aminophenyl)-3-chloroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1Cl HYBVISCYJVVEDX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- RZJRJXONCZWCBN-UHFFFAOYSA-N alpha-octadecene Natural products CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- YVHAIVPPUIZFBA-UHFFFAOYSA-N cyclopentaneacetic acid Natural products OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 description 3
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
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- 150000002500 ions Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 3
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
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- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-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
- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical class OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-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
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- XWINCPYLXQTPQV-UHFFFAOYSA-N piperazine Chemical group C1CNCCN1.C1CNCCN1 XWINCPYLXQTPQV-UHFFFAOYSA-N 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 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
- 238000007761 roller coating Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005590 trimellitic acid group Chemical group 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-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
- 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
- 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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
-
- 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
- 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
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Abstract
The invention relates to 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) and a solvent (B). Wherein the polymer (A) is obtained by reacting a tetracarboxylic dianhydride compound (a) and a diamine compound (b). The liquid crystal alignment agent has specific viscosity, can prepare a liquid crystal alignment film with high Young modulus and a liquid crystal display element comprising the liquid crystal alignment film, and the prepared liquid crystal display element has no broken bright point defect.
Description
Technical field
The present invention is a kind of related crystal aligning agent, liquid crystal orienting film and liquid crystal display element, is especially to provide a kind of tool
There is the crystal aligning agent of particular viscosity, and its form the liquid crystal orienting film with high Young's modulus, and there is the liquid crystal to match
To the liquid crystal display element of film.
Background technique
In recent years, the exploitation of new liquid crystal display element flourishes, wherein such as industry develops a kind of liquid crystal display
Element drives liquid crystal by two electrodes are configured on single sided substrate in a manner of veteranellinae shape, and substrate surface is made to generate parallel electricity
, to control liquid crystal molecule.Above-mentioned liquid crystal display element is commonly referred to as transverse electric field effect type (IPS type), it is known that it has
Outstanding wide viewing angle characteristic.However, above-mentioned IPS type liquid crystal display element, which still has, generates asking for ghost because ion concentration is excessively high
Topic.
Japanese Patent Laid-Open 2009-175684 bulletin disclose a kind of low ion concentration liquid crystal orienting film and a kind of use
To prepare the diamine compound containing piperazine (piperazine) structure of liquid crystal orienting film.By using the diamines containing piperazine structure
Compound, obtained alignment film can improve the excessively high problem of ion concentration.
However, the Young's modulus (Young ' s Modulus) of liquid crystal orienting film obtained by above-mentioned crystal aligning agent is too low, when
When it is applied to liquid crystal display element, obtained liquid crystal display element tends to have the defect that a large amount of broken bright spots generate, and reduces it
Display quality.
It can be seen from the above, how to improve liquid crystal orienting film to meet the requirement of current IPS type liquid crystal display dealer
Young's modulus, the liquid crystal display element to eliminate broken fleck defect make great efforts the target studied as the art person.
Summary of the invention
Therefore, an aspect of the invention is to provide a kind of crystal aligning agent.This crystal aligning agent include polymer (A) and
Solvent (B).
Another aspect of the invention is to provide a kind of liquid crystal orienting film, and it includes above-mentioned crystal aligning agents.
Another aspect of the invention is to provide a kind of liquid crystal display element, with above-mentioned liquid crystal orienting film, and this
The defect that liquid crystal display element does not have broken bright spot to generate.
Above-mentioned aspect according to the present invention, proposes a kind of crystal aligning agent.This crystal aligning agent includes polymer (A) and molten
Agent (B), analysis states it below.
Polymer (A)
Polymer (A) of the invention is reacted with diamine compound (b) by tetracarboxylic dianhydride's compound (a) and is obtained.
The preferred embodiment of above-mentioned polymer (A) is that polyamic acid polymer, polyimide polymer, polyimides system are embedding
Section co-polymer or these combinations.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 a combination.
Tetracarboxylic dianhydride's compound (a)
Tetracarboxylic dianhydride's compound (a) of the invention may include tetracarboxylic dianhydride's compound (a- as shown in following formula (I)
1).Secondly, tetracarboxylic dianhydride's compound (a) is selectively included other tetracarboxylic dianhydride's compounds (a-2).
Tetracarboxylic dianhydride's compound (a-1)
Tetracarboxylic dianhydride's compound (a-1) has the structure as shown in formula (I):
In formula (I), R1、R2、R3、R4、R5And R6Separately selected from by halogen atom, be substituted or do not replace
Alkyl, the alkoxy for being substituted or not replacing and be substituted or the aromatic radical that does not replace composed by a group at least one；Z
Separately representative-CONH- ,-NHCO- ,-NHCO2,-OCONH- or-NHCONH-；H, i, j and k separately represent 0
To 4 integer；M and n separately represents 0 to 3 integer.
Halogen atom above-mentioned can be fluorine atom, chlorine atom, bromine atom or iodine atom etc..Preferably, the halogen atom can
For fluorine atom, chlorine atom or bromine atom.The alkyl for being substituted or not replacing can be methyl, ethyl, propyl, isopropyl or trifluoro
The alkyl that the carbon numbers such as methyl are 1 to 8.Preferably, the alkyl for being substituted or not replacing can be methyl, trifluoromethyl or isopropyl
Base.This is substituted or the alkoxy that does not replace can be the alkoxy that the carbon numbers such as methoxyl group, ethyoxyl or phenoxy group are 1 to 8.Preferably
Ground, which can be methoxyl group or phenoxy group.The aromatic radical for being substituted or not replacing can be benzene
The monocycle or fused-ring aromatic that the carbon numbers such as base, naphthalene or p- methoxyphenyl are 6 to 14.Preferably, this is substituted or not
Substituted aromatic radical can be phenyl.Preferably, the Z can be-CONH- or-NHCO-.
M and n above-mentioned preferably can separately represent 0 to 2 integer, and h, i, j and k above-mentioned preferably can be independently
Ground represents 0 to 2 integer.
In one embodiment, which may include as shown in following formula (I-1) to formula (I-8)
Tetracarboxylic dianhydride's compound.
Tetracarboxylic dianhydride's compound (a-1) above-mentioned individually a kind of can use or mix a variety of uses.
Total usage amount based on tetracarboxylic dianhydride's compound (a) is 100 moles, and tetracarboxylic dianhydride's compound (a-1's) makes
Dosage is 5 moles to 60 moles, preferably 10 moles to 55 moles, and more preferably 15 moles to 50 moles.
It is obtained if tetracarboxylic dianhydride's compound (a) of crystal aligning agent does not include tetracarboxylic dianhydride's compound (a-1)
Liquid crystal orienting film Young's modulus it is too low, be unable to improve the broken fleck defect of liquid crystal display element, and be difficult to promote display product
Matter.
Wherein, as the Z representative-CONH- or-NHCO- in tetracarboxylic dianhydride's compound (a-1) as shown in formula (I), institute
Liquid crystal orienting film obtained has compared with high Young's modulus, and can further improve the broken fleck defect of liquid crystal display element.
Other tetracarboxylic dianhydride's compounds (a-2)
In addition to tetracarboxylic dianhydride's compound (a-1) above-mentioned, in the range of not influencing effect, tetrabasic carboxylic acid of the invention
Dianhydride compound (a) is also selectively included other tetracarboxylic dianhydride's compounds (a-2).
The preferred embodiment of other tetracarboxylic dianhydride's compounds (a-2) is (1) aliphatic tetracarboxylic dianhydride compound, (2)
Alicyclic tetracarboxylic acid dianhydride compound, (3) aromatic tetracarboxylic dianhydride compound or (4) have such as formula (IV-1) to (IV-6) institute
Tetracarboxylic dianhydride's compound for the structure shown etc..
(1) aliphatic tetracarboxylic dianhydride's compound of the invention may include, but are not limited to ethane tetracarboxylic dianhydride or butane four
Aliphatic tetracarboxylic dianhydride's compound of carboxylic acid dianhydride etc..
(2) Alicyclic tetracarboxylic acid dianhydride compound of the invention may include, but are not limited to 1,2,3,4- cyclobutane tetrabasic carboxylic acids two
Acid anhydride, 1,2- dimethyl -1,2,3,4- cyclobutane tetracarboxylic dianhydrides, 1,3- dimethyl -1,2,3,4- cyclobutane tetracarboxylic dianhydrides, 1,
3- bis- chloro- 1,2,3,4- cyclobutane tetracarboxylic dianhydrides, 1,2,3,4- tetramethyls -1,2,3,4- cyclobutane tetracarboxylic dianhydrides, 1,2,
3,4- pentamethylene tetracarboxylic dianhydrides, 1,2,4,5- cyclopentanetetracarboxylic's dianhydrides, 3,3 ', 4,4 '-dicyclohexyl tetracarboxylic dianhydrides,
Cis- 3,7- dibutyl suberyl -1,5- diene -1,2,5,6- tetracarboxylic dianhydrides, 2,3,5- tricarboxylic cyclopentyl acetic acid dianhydrides or
Two rings [2.2.2]-octyl- 7- alkene -2,3, the Alicyclic tetracarboxylic acid dianhydride compound of 5,6- tetracarboxylic dianhydrides etc..
The concrete example of (3) aromatic tetracarboxylic dianhydride compound of the invention may include, but are not limited to dicarboxyl -1 3,4-,
2,3,4- naphthane -1- amber acid dianhydrides, the equal tetracarboxylic dianhydride of benzene, 2,2 ', 3,3 '-benzophenone tetracarboxylic dianhydrides, 3,3 ', 4,
4 '-benzophenone tetracarboxylic dianhydrides, 3,3 ', 4,4 '-biphenyl sulfone tetracarboxylic dianhydrides, Isosorbide-5-Nitrae, 5,8- naphthalene tetracarboxylic acid dianhydrides, 2,3,6,
7- naphthalene tetracarboxylic acid dianhydride, 3,3 ' -4,4 '-diphenylethane tetracarboxylic dianhydrides, 3,3 ', 4,4 '-dimethyl diphenyl silane tetracarboxylic acids
Acid dianhydride, 3,3 ', 4,4 '-tetraphenyl silane tetracarboxylic dianhydrides, 1,2,3,4- furans tetracarboxylic dianhydrides, 2,3,3 ', 4 '-diphenyl ether
Tetracarboxylic dianhydride, 3,3 ', 4,4 '-diphenyl ether tetracarboxylic dianhydrides, 4,4 '-bis- (3,4- di carboxyl phenyloxy) diphenyl ether dianhydrides,
2,3,3 ', 4 '-diphenyl sulfide tetracarboxylic dianhydrides, 3,3 ', 4,4 '-diphenyl sulfide tetracarboxylic dianhydrides, 4,4 '-bis- (3,4- dicarboxyls
Phenoxy group) diphenyl sulfone dianhydride, 4,4 '-bis- (3,4- di carboxyl phenyloxy) diphenyl propane dianhydrides, 3,3 ', 4,4 '-perfluors different sub- third
Two phthalic acid dianhydride of base, 2,2 ', 3,3 '-biphenyltetracaboxylic dianhydrides, 2,3,3 ', 4 '-biphenyltetracaboxylic dianhydrides, 3,3 ', 4,
4 '-biphenyltetracaboxylic dianhydrides, bis- (phthalic acid) phosphniline oxide dianhydrides, it is p- stretch bis- (triphenylbenzene diacid) dianhydrides of phenyl-,
It is m- to stretch bis- (triphenylbenzene diacid) dianhydrides of phenyl -, bis- (triphenylbenzene diacid) -4,4 '-diphenyl ether dianhydride, bis- (triphenylbenzenes
Diacid) -4,4 '-diphenyl methane dianhydrides, ethylene glycol-bis- (dehydration trimellitates), bis- (the dehydration trimellitic acids of propylene glycol -
Ester), 1,4-butanediol-bis- (dehydrations trimellitate), 1,6- hexylene glycol-bis- (dehydration trimellitate), 1,8- ethohexadiol-bis-
(dehydration trimellitate), bis- (4- hydroxyphenyl) propane-of 2,2- bis- (dehydration trimellitates), 2,3,4,5- tetrahydrofuran tetracarboxylic acids
Acid dianhydride, 1,3,3a, 4,5,9b- hexahydro -5- (bis- 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- (bis- 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- (bis- side oxygroup -3- furyl of tetrahydro -2,5-)-naphtho-
[1,2-c]-furans -1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -7- methyl -5- (bis- 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- (bis- side oxygroups of tetrahydro -2,5- -
3- furyl)-naphtho- [1,2-c]-furans -1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -8- methyl -5- (tetrahydros -2,5- bis-
Side oxygroup -3- furyl)-naphtho- [1,2-c]-furans -1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -8- ethyl -5- (tetrahydros -
2,5- bis- side oxygroup -3- furyls)-naphtho- [1,2-c]-furans -1,3- diketone, 1,3,3a, 4,5,9b- hexahydro -5,8- diformazans
Base -5- (bis- side oxygroup -3- furyl of tetrahydro -2,5-)-naphtho- [1,2-c]-furans -1,3- diketone, 5- (2,5- bis- side oxygroups four
Hydrogen furyl) -3- methyl -3- cyclohexene -1,2- dicarboxylic acid dianhydride etc..
(4) of the invention have tetracarboxylic dianhydride's compound difference of the structure as shown in formula (IV-1) to (IV-6) as follows
It is shown.
In formula (IV-5), X1 represents the bivalent group with aromatic rings, X2And X3Can be to be identical or different, and X2And X3
Hydrogen atom or alkyl can be separately represented, and r represents 1 to 2 integer.This has the structure as shown in formula (IV-5)
Tetracarboxylic dianhydride's compound is preferably the compound with the structure as shown in following formula (IV-5-1) to formula (IV-5-3).
In formula (IV-6), X4Represent the bivalent group with aromatic rings, X5And X6Can be to be identical or different, and X5And X6It can
Separately represent hydrogen atom or alkyl.There is tetracarboxylic dianhydride's compound of the structure as shown in formula (IV-6) to be preferably for this
Compound with the structure as shown in following formula (IV-6-1).
Preferably, tetracarboxylic dianhydride's compound (a-2) may include, but are not limited to 1,2,3,4- cyclobutane tetracarboxylic dianhydrides
(1,2,3,4-cyclobutane tetracarboxylic acid dianhydride), 1,2,3,4- pentamethylene tetrabasic carboxylic acids two
Acid anhydride, 2,3,5- tricarboxylic cyclopentyl acetic acid dianhydride (2,3,5-tri carboxycyclopentylacetic acid
Dianhydride), 1,2,4,5- cyclopentanetetracarboxylic's dianhydrides, 3,4- dicarboxyl -1,2,3,4- naphthane -1- amber acid dianhydrides,
The equal tetracarboxylic dianhydride of benzene (pyromellitic dianhydride), 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydrides or 3,3 ',
4,4 '-biphenyl sulfone tetracarboxylic dianhydrides etc..Tetracarboxylic dianhydride's compound (a-2) above-mentioned individually a kind of can use or mix a variety of
It uses.
Total usage amount based on diamine compound (b) is 100 moles, and the usage amount of tetracarboxylic dianhydride's compound (a) is 20
Mole to 200 moles, and preferably 30 moles to 120 moles.
Diamine compound (b)
Diamine compound (b) of the invention includes the diamine compound (b-1) as shown in following formula (II) and/or such as following formula
(III) diamine compound shown in (b-2).Secondly, the diamine compound (b) is selectively included other diamine compounds
(b-3)。
Diamine compound (b-1)
The diamine compound (b-1) has the structure as shown in following formula (II):
In formula (II), W1Represent replaced 3 grades of nitrogen-atoms and carbon number as 4 to 6 naphthenic base of stretching, and W2Represent carbon number
Alkyl is stretched for 1 to 5.
Wherein, which refers to that 3 bonds of nitrogen-atoms are bonded with the atom other than hydrogen atom.Preferably, this 3
Grade nitrogen-atoms represents the nitrogen-atoms with carbon atom bond.
Preferably, in formula (II), the W1It representsAnd W2Representing carbon number is 1 to 5
Stretch alkyl.
In a concrete example, the diamine compound (b-1) as shown in formula (II) has such as following formula (II-1) to formula (II-5)
Shown in structure diamine compound:
Diamine compound (b-1) above-mentioned individually a kind of can use or mix a variety of uses.
Total usage amount based on diamine compound (b) is 100 moles, the usage amount of diamine compound (b-1) be 3 moles extremely
45 moles, preferably 6 moles to 40 moles, and more preferably 9 moles to 35 moles.
If the diamine compound (b) of crystal aligning agent include as shown in formula (II) when diamine compound (b-1), it is obtained
Liquid crystal orienting film have compared with high Young's modulus, and can further improve the broken fleck defect of liquid crystal display element.
Diamine compound (b-2)
The diamine compound (b-2) has the structure as shown in following formula (III):
In formula (III), which represents 1 to 12 integer.
In one embodiment, the diamine compound (b-2) with the structure as shown in formula (III) may include having such as following formula
The diamine compound of structure shown in (III-1) to formula (III-3):
In formula (III-1) into formula (III-3), y can represent 1 to 12 integer.
The concrete example of the aforementioned diamine compound with the structure as shown in formula (III-1) can be two (4- amido phenoxy groups)
Methane, 1,2- bis- (4- amido phenoxy group) ethane, 1,3- bis- (4- amido phenoxy group) propane, Isosorbide-5-Nitrae-two (4- amido phenoxy group) fourth
Alkane, 1,5- bis- (4- amido phenoxy group) pentane, 1,6- bis- (4- amido phenoxy group) hexane, 1,7- bis- (4- amido phenoxy group) heptan
Alkane, 1,8- bis- (4- amido phenoxy group) octane, 1,9- bis- (4- amido phenoxy group) nonane, (the 4- amido phenoxy group) last of the ten Heavenly stems of 1,10- bis-
Any mixing of alkane or above compound.
The concrete example of the aforementioned diamine compound with the structure as shown in formula (III-2) can be two (2- amido phenoxy groups)
Methane, 1,2- bis- (2- amido phenoxy group) ethane, 1,3- bis- (2- amido phenoxy group) propane, Isosorbide-5-Nitrae-two (2- amido phenoxy group) fourth
Alkane, 1,5- bis- (2- amido phenoxy group) pentane, 1,6- bis- (2- amido phenoxy group) hexane, 1,7- bis- (2- amido phenoxy group) heptan
Alkane, 1,8- bis- (2- amido phenoxy group) octane, 1,9- bis- (2- amido phenoxy group) nonane, (the 2- amido phenoxy group) last of the ten Heavenly stems of 1,10- bis-
Any mixing of alkane or above compound.
The concrete example of the aforementioned diamine compound with the structure as shown in formula (III-3) can be two (3- amido phenoxy groups)
Methane, 1,2- bis- (3- amido phenoxy group) ethane, 1,3- bis- (3- amido phenoxy group) propane, Isosorbide-5-Nitrae-two (3- amido phenoxy group) fourth
Alkane, 1,5- bis- (3- amido phenoxy group) pentane, 1,6- bis- (3- amido phenoxy group) hexane, 1,7- bis- (3- amido phenoxy group) heptan
Alkane, 1,8- bis- (3- amido phenoxy group) octane, 1,9- bis- (3- amido phenoxy group) nonane, (the 3- amido phenoxy group) last of the ten Heavenly stems of 1,10- bis-
Any mixing of alkane or above compound.
Preferably, the concrete example of the diamine compound (b-2) with the structure as shown in formula (III) can be 1,3-, bis- (4-
Amido phenoxy group) propane, Isosorbide-5-Nitrae-two (4- amido phenoxy group) butane, 1,5- bis- (4- amido phenoxy group) pentane, (the 4- amine of 1,6- bis-
Phenoxyl) hexane, 1,7- bis- (4- amido phenoxy group) heptane, 1,8- bis- (4- amido phenoxy group) octane, (the 2- amido of 1,3- bis-
Phenoxy group) propane, Isosorbide-5-Nitrae-two (2- amido phenoxy group) butane, 1,5- bis- (2- amido phenoxy group) pentane, (the 2- amido benzene of 1,6- bis-
Oxygroup) hexane, 1,7- bis- (2- amido phenoxy group) heptane, 1,8- bis- (2- amido phenoxy group) octane, (the 3- amido benzene oxygen of 1,3- bis-
Base) propane, Isosorbide-5-Nitrae-two (3- amido phenoxy group) butane, 1,5- bis- (3- amido phenoxy group) pentane, (the 3- amido benzene oxygen of 1,6- bis-
Base) hexane, 1,7- bis- (3- amido phenoxy group) heptane or 1,8- bis- (3- amido phenoxy group) octane etc..Diamine compound above-mentioned
(b-2) it can individually a kind of use or mixing repetition kind use.
Total usage amount based on diamine compound (b) is 100 moles, and the usage amount of diamine compound (b-2) is 10 moles
To 95 moles, preferably 15 moles to 90 moles, and more preferably 20 moles to 85 moles.
If the diamine compound (b) of crystal aligning agent include as shown in formula (III) when diamine compound (b-2), it is made
The liquid crystal orienting film obtained has compared with high Young's modulus, and can further improve the broken fleck defect of liquid crystal display element.
If the diamine compound (b) of crystal aligning agent is simultaneously comprising the diamine compound (b-1) as shown in formula (II) and such as
Shown in formula (III) when diamine compound (b-2), obtained liquid crystal orienting film can have more high Young's modulus, and can be into one
Step improves the broken fleck defect of liquid crystal display element.
Other diamine compounds (b-3)
In addition to diamine compound above-mentioned (b-1) and/or diamine compound (b-2), in the range of not influencing effect,
Diamine compound (b) of the invention is also selectively included other diamine compounds (b-3).
Other diamine compounds (b-3) may include, but are not limited to 1,2- diamino-ethane, 1,3-, bis- amido propane, Isosorbide-5-Nitrae-two
Amido butane, 1,5- diaminopentane, 1,6- phenylenediamine, 1,7- diamines base heptane, 1,8-, bis- amido octane, 1,9- diamines
Base nonane, 1,10-, bis- amido decane, 4,4 '-diamines base heptanes, 1,3-, bis- amido -2,2- dimethylpropane, 1,6-, bis- amido -
2,5- dimethylhexanes, 1,7-, bis- amido -2,5- dimethyl heptane, 1,7-, bis- amido -4,4- dimethyl heptane, 1,7- diamines
Base -3- methyl heptane, 1,9-, bis- amido -5- methylnonane, 2,11-, bis- amido dodecane, 1,12-, bis- amido octadecane, 1,2-
Bis- (3- amido propoxyl group) ethane, 4,4 '-two amido dicyclohexyl methyl hydrides, 4,4 '-two amido -3,3 '-dimethyidicyclohexyls
Amine, 1,3- diamines butylcyclohexane, Isosorbide-5-Nitrae-diamines butylcyclohexane, isophorone diamine, tetrahydro bicyclopentadiene diamines, tricyclic
(6.2.1.02,7)-endecatylene dimethyl-p-phenylenediamine, 4,4 '-di-2-ethylhexylphosphine oxides (cyclo-hexylamine), 4,4 '-two aminodiphenylmethanes,
4,4 '-two amido diphenylethanes, 4,4 '-two amido diphenyl sulfones, 4,4 '-two amido benzanilides, 4,4 '-two amidos two
Phenyl ether, 3,4 '-two amido diphenyl ethers, 1,5-, bis- amido naphthalene, -1,3,3- trimethyl hydrogen of 5- amido -1- (4 '-aminocarbonyl phenyl)
Indenes, -1,3,3- trimethyl hydrogen indenes of 6- amido -1- (4 '-aminocarbonyl phenyl), hexahydro -4,7- first bridge stretch hydrogen indenyl dimethylene diamines,
Bis- [4- (the 4- amidos of 3,3 '-two aminobenzophenones, 3,4 '-two aminobenzophenones, 4,4 '-two aminobenzophenones, 2,2-
Phenoxy group) phenyl] propane, bis- [4- (the 4- amido phenoxy group) phenyl] hexafluoropropane of 2,2-, bis- (4- aminocarbonyl phenyl) hexafluoros of 2,2-
Bis- [4- (the 4- amido phenoxy group) phenyl] sulfones of propane, 2,2-, bis- (the 4- amido phenoxy group) benzene of Isosorbide-5-Nitrae-, bis- (the 4- amido benzene oxygen of 1,3-
Base) benzene, bis- (the 3- amido phenoxy group) benzene of 1,3-, bis- (4- the aminocarbonyl phenyl) -10- hydrogen anthracenes of 9,9-, bis- (4- aminocarbonyl phenyl) anthracenes of 9,10-
[9,10-bis (4-aminophenyl) anthracene], 2,7-, bis- amido Fluorene, 9,9- bis- (4- aminocarbonyl phenyl) Fluorene, 4,4 '-is sub-
Methyl-bis- (2- chloroanilines), 4,4 '-(p- to stretch phenyl isopropylidene) dianils, 4,4 '-(m- to stretch phenyl isopropylidene) double benzene
Amine, 2,2 '-bis- [4- (4- amido -2- 4-trifluoromethylphenopendant) phenyl] hexafluoropropane, 4,4 '-bis- [(4- amido -2- fluoroforms
Base) phenoxy group]-octafluorobiphenyl, bis- amido benzene { 5- of 5- [4- (4- pentane butylcyclohexyl) cyclohexyl] phenylmethylene -1,3-
[4- (4-n-pentylcyclohexyl) cyclohexyl] phenylmethylene-1,3-diaminobenzene }, 1,1-
Bis- [4- (4- amido phenoxy group) phenyl] -4- (4- ethylphenyl) hexamethylene { 1,1-bis [4- (4-aminophenoxy)
Phenyl] -4- (4-ethyl phenyl) cyclohexane } or other two aminations as shown in following formula (V-1) to formula (V-29)
Close object.
In formula (V-1), Y1Representative-O-, And Y2Represent the alkyl or derivative of group containing steroid, trifluoromethyl, fluorine-based, carbon number as 2 to 30
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 (V-1) preferably can be 2,4-, bis- aminocarbonyl phenyl Ethyl formate (2,4-
Diaminophenyl ethyl formate), 3,5-, bis- aminocarbonyl phenyl Ethyl formate (3,5-diaminophenyl ethyl
Formate), 2,4-, bis- aminocarbonyl phenyl propyl formate (2,4-diaminophenyl propyl formate), 3,5-, bis- amido
Phenyl propyl formate (3,5-diaminophenyl propyl formate), bis- amido benzene (1- of 1- dodecyloxy -2,4-
Dodecoxy-2,4-diamino-benzene), 1- hexadecane epoxide -2,4- bis- amido benzene (1-hexadecoxy-2,4-
Diaminobenzene), bis- amido benzene (1-octadecoxy-2,4-diaminobenzene) of 1- octadecane epoxide -2,4- or
Other diamine compounds shown in following formula (V-1-1) to formula (V-1-6).
In formula (V-2), Y3Representative-O-, Y4And Y5Expression stretches aliphatic ring, stretches aromatic ring or stretches heterocyclic group, and Y6Represent 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 (V-2) preferably can be for as shown in following formula (V-2-1) to formula (V-2-13)
Diamine compound:
In formula (V-2-10) into formula (V-2-13), s can represent 3 to 12 integer.
In formula (V-3), Y7Represent 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.Y8For integer of 1 to 3.Work as Y8When greater than 1, multiple Y7It can be identical or different.
Diamine compound shown in above-mentioned formula (V-3) is preferably selected from (1) Y8Be 1: p- diamines benzene, m- diamines benzene,
O- diamines benzene or 2, bis- carbaryl of 5- etc.；(2)Y8For 2:4,4 '-benzidines, 2,2 '-dimethyl -4,4 '-two amidos connection
Benzene, 3,3 '-dimethyl -4,4 '-benzidines, 3,3 '-dimethoxy-4 's, 4 '-benzidines, 2,2 '-two chloro- 4,4 ' -
Benzidine, 3,3 '-two chloro- 4,4 '-benzidines, 2,2 ', 5,5 '-four chloro- 4,4 '-benzidines, 2,2 '-two
Chloro- 4,4 '-two amido -5,5 '-dimethoxy-biphenyls or 4,4 '-two amido -2,2 '-bis- (trifluoromethyl) biphenyl etc.；(3)Y8For
Bis- (4 '-aminocarbonyl phenyl) benzene of 3:1,4- etc., more preferably be selected from p- diamines benzene, 2,5-, bis- carbaryl, 4,4 '-benzidines,
3,3 '-dimethoxy-4 's, 4 '-benzidines or bis- (4 '-aminocarbonyl phenyl) benzene of Isosorbide-5-Nitrae-.
In formula (V-4), Y9Represent 1 to 5 integer.The formula (V-4) is preferably selected from 4,4 '-two amido diphenyl sulphur
Ether.
In formula (V-5), Y10And Y12It can be identical or different, and respectively represent bivalent organic group, Y11Representative is derived from
The bivalent group of the nitrogen atoms cyclic structure such as pyridine, pyrimidine, triazine, piperidines and piperazine.
Diamine compound shown in formula (V-5) can be preferably the diamine compound as shown in following formula (V-5-1):
In formula (V-6), Y13、Y14、Y15And Y16It respectively can be identical or different, and carbon number can be represented as 1 to 12 hydrocarbon
Base.Y17Represent integer of 1 to 3, and Y18Represent integer of 1 to 20.
In formula (V-7), Y19Representative-O- stretches cyclohexyl, Y20Representative-CH2, Y21Representative stretches phenyl or stretches hexamethylene
Base, and Y22Represent hydrogen atom or heptyl.
Diamine compound shown in above-mentioned formula (V-7) is preferably selected from two as shown in following formula (V-7-1) and formula (V-7-2)
Amine compounds.
Other diamine compounds (b-3) shown in formula (V-8) to formula (V-29) are as follows:
In formula (V-16) into formula (V-19), Y23The 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 (V-20) into formula (V-24), Y24The 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-3) preferably may include, but are not limited to 1,2- diamino-ethane, 4,4 '-two amido, two hexamethylene
Methylmethane, 4,4 '-two aminodiphenylmethanes, 4,4 '-two amido diphenyl ethers, 5- [4- (4- pentane butylcyclohexyl) hexamethylene
Base] bis- amido benzene of phenylmethylene -1,3-, bis- [4- (4- amido phenoxy group) phenyl] -4- (4- ethylphenyl) hexamethylenes of 1,1-,
2,4- bis- aminocarbonyl phenyl Ethyl formates, p- diamines benzene, m- diamines benzene, o- diamines benzene, formula (V-1-1), formula (V-1-2), formula
(V-1-5), compound represented by formula (V-2-1), formula (V-2-11), formula (V-7-1), formula (V-25) or formula (V-28).
Other diamine compounds (b-3) above-mentioned can the individually a kind of or a variety of uses of mixing.
Total usage amount based on diamine compound (b) is 100 moles, and the usage amount of other diamine compounds (b-3) is rubbed for 0
You are to 97 moles, and preferably 0 mole to 94 moles, and more preferably 0 mole to 91 moles.
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 compound (a) and the mixture of diamine compound (b) are dissolved in that the preparation method of object, which comprises the steps of:,
In solvent, 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, it then again will be above-mentioned
Reaction solution polyamic acid polymer can be obtained in such a way that evaporator carries out vacuum distillation, or it is above-mentioned reaction is molten
Liquid pours into a large amount of lean solvent, obtains a precipitate, and then the precipitate is dried via the mode that is dried under reduced pressure,
Polyamic acid polymer can be obtained.
Can be identical or different with the solvent in following crystal aligning agents for the solvent in polycondensation reaction, and it is used for bunching
The solvent closed in reaction is not particularly limited, as long as can dissolve reactant and product.Preferably, solvent include but
It is not limited to (1) non-proton system's polar solvent, such as: n-methyl-2-pyrrolidone (N-methyl-2-pyrrolidinone；
NMP), n,N-dimethylacetamide, n,N-Dimethylformamide, dimethyl sulfoxide, gamma-butyrolacton, 4-methyl urea or pregnancy
Non-proton system's polar solvent of base phosphoric acid triamine etc.；(2) phenol system solvent, such as: m-cresol, dimethlbenzene, phenol or halogenated phenols
Deng phenol system solvent.Usage amount based on mixture is 100 parts by weight, and the usage amount for the solvent in polycondensation reaction is preferable
For 200 parts by weight to 2000 parts by weight, and more preferably 300 parts by weight are to 1800 parts by weight.
Particularly, in polycondensation reaction, solvent can and with suitable lean solvent, wherein lean solvent not will cause polyamide
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,
Such as: the alcohols of methanol, ethyl alcohol, isopropanol, cyclohexanol, ethylene glycol, propylene glycol, 1,4-butanediol or triethylene glycol etc.；(2) ketone
Class, such as: the ketone of acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK) or 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, Isosorbide-5-Nitrae-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 compound (b) is 100 parts by weight, and the usage amount of lean solvent is preferably 0 parts by weight to 60 parts by weight, and more preferably 0
Parts by weight are to 50 parts by weight.
The preparation of polyimide polymer of the invention can be general method, preferably, the system of polyimide polymer
One mixture is first dissolved in solution by Preparation Method, and wherein mixture includes tetracarboxylic dianhydride's compound (a) and diamine compound
(b), and polymerization reaction is carried out, to form polyamic acid polymer.Then, in the presence of dehydrating agent and catalyst, further plus
Heat, and dehydration closed-loop reaction is carried out, so that the amide acid functional group in polyamic acid polymer changes via dehydration closed-loop reaction
At acid imide functional group (i.e. imidizate), and obtain 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, and more preferably 300 parts by weight are 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, and more preferably 40 DEG C to 150 DEG C.If the operation temperature of dehydration closed-loop reaction is lower than 40 DEG C, imidizate
Reaction not exclusively, and reduces the degree of imidisation of polyamic acid polymer.However, if the operation temperature of dehydration closed-loop reaction is high
When 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, trimethyl
The pyridine compounds and their of pyridine or lutidines etc.；(2) three-level aminated compounds, such as: the three-level amine of triethylamine etc.
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 block copolymer of the invention is polyamic acid block copolymer, polyamides
Imines block copolymer, polyamic acid-polyimide block co-polymer or these any combination.
The preparation of polyimides system block copolymer of the invention can be general method, preferably, polyimides system
One starting material is first dissolved in solvent by the preparation method of block copolymer, and carries out polycondensation reaction, wherein the starting
Object includes above-mentioned at least one polyamic acid polymer and/or above-mentioned at least one polyimide polymer, and can be into one
Step ground includes tetracarboxylic dianhydride's compound (a) and diamine compound (b).
Tetracarboxylic dianhydride's compound (a) and diamine compound (b) in the starting material are to prepare polyamic acid with above-mentioned
Tetracarboxylic dianhydride's compound (a) used in polymer is identical as diamine compound (b), and for molten in polycondensation reaction
Agent can be identical as the solvent in following crystal aligning agents, 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
Parts by weight are to 2000 parts by weight, and more preferably 300 parts by weight are to 1800 parts by weight.The operation temperature of polycondensation reaction is preferably 0
DEG C to 200 DEG C, and 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 compound (a) and diamine compound (b) is different；(5) polyimide polymer, tetracarboxylic dianhydride's compound and diamines
Compound, wherein at least one of tetracarboxylic dianhydride's compound and diamine compound and formation polyimide polymer
The structure of used tetracarboxylic dianhydride's compound (a) and diamine compound (b) is different；(6) polyamic acid polymer, polyamides are sub-
Amine polymer, tetracarboxylic dianhydride's compound and diamine compound, wherein at least one of tetracarboxylic dianhydride's compound and diamines
With tetracarboxylic dianhydride's compound (a) and diamine compound used in formation polyamic acid polymer or polyimide polymer
(b) structure is different；(7) two kinds of different polyamic acid polymers of structure, tetracarboxylic dianhydride's compound and diamine compound；
(8) two kinds of different polyimide polymers of structure, tetracarboxylic dianhydride's compound and diamine compound；(9) two kinds of terminal groups are
Anhydride group and the different polyamic acid polymer and diamine compound of structure；(10) two kinds of terminal groups are amido and structure is different
Polyamic acid polymer and tetracarboxylic dianhydride's compound；(11) two kinds of terminal groups be anhydride group and structure it is different polyamides it is sub-
Amine polymer and diamine compound；(12) two kinds of terminal groups are amido and the different polyimide polymer and tetracarboxylic acid of structure
Acid dianhydride compounds.
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-functional
Compound may include, but are not limited to (1) unitary acid anhydrides, such as: maleic anhydride, phthalic anhydride, itaconic anhydride, positive decyl amber
The unitary acid anhydrides of amber acid anhydrides, 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, the positive last of the ten Heavenly stems
Amine, n-undecane amine, n-dodecane amine, n-tridecane amine, n-tetradecane amine, n-pentadecane amine, hexadecane amine, n-heptadecane
The monoamine compound of amine, n-octadecane amine or n-eicosane amine etc.；(3) monoisocyanate compound, such as: phenyl isocyanate or
The monoisocyanate compound of isocyanic 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, and more preferably 15,000 to 60,000.
Solvent (B)
The preferred embodiment of solvent (B) according to the present invention is nitrogen-N-methyl-2-2-pyrrolidone N, gamma-butyrolacton, γ-Ding Nei
Amide, 4- hydroxy-4-methyl-2-pentanone, ethylene glycol single methyl ether, butyl lactate, butyl acetate, methoxy methyl propionate, second
Oxygroup ethyl propionate, Ethylene glycol methyl ether, glycol ethyl ether, ethylene glycol n-propyl ether, ethylene glycol isopropyl ether, ethylene glycol are just
Butyl ether, ethylene glycol dimethyl ether, ethylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol (DEG)
Monomethyl ether, carbiphene, diethylene glycol monomethyl ether acetic acid esters, diethylene glycol monoethyl ether acetate, nitrogen, nitrogen-diformazan
Base formamide, nitrogen, nitrogen-dimethyl acetamide.The solvent individually a kind of can use or mix a variety of uses.
Usage amount based on the polymer (A) is 100 parts by weight, and the usage amount of solvent (B) can be 500 to 3,000 weight
Part, preferably 800 to 2,500 parts by weight, and more preferably 1,000 to 2,000 parts by weight.
Additive (C)
It is not influencing within the scope of effect of the invention, crystal aligning agent optionally adds additive (C), and additive
It (C) is epoxide or the silane compound with functional groups etc..The effect of additive (C) is for improving the liquid crystal
The adhesion of alignment film and substrate surface.Additive (C) individually a kind of can use or mix 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- hexylene glycol bisglycidyl ethers, glycerine bisglycidyl ethers, 2,2- dibromoneopentyl glycol diepoxy propyl
Ether, 1,3,5,6- tetra- glycidyl -2,4- hexylene glycols, N, N, N ',-four glycidyl of N '-m-xylenedimaine, 1,3- it is bis- (N,
N- diepoxy propyl aminomethyl) hexamethylene, N, N, N ',-four glycidyl -4 N ', 4 '-two aminodiphenylmethanes, 3- (N-
Allyl-N- glycidyl) aminocarbonyl propyl trimethoxy silane, 3- (N, N- diepoxy propyl) aminocarbonyl propyl trimethoxy silane
Deng.
Usage amount based on polymer (A) be 100 parts by weight, the usage amount of epoxide be generally 40 parts by weight with
Under, and preferably 0.1 parts by weight are to 30 parts by weight.
The above-mentioned silane compound with functional groups may include, but are not limited to 3- aminocarbonyl propyl trimethoxy silane, 3-
Aminocarbonyl propyl triethoxysilane, 2- aminocarbonyl propyl trimethoxy silane, 2- aminocarbonyl propyl triethoxysilane, N- (2- amido
Ethyl) -3- aminocarbonyl propyl trimethoxy silane, N- (2- amido ethyl) -3- aminocarbonyl propyl methyl dimethoxysilane, 3- urea groups
Propyl trimethoxy silicane (3-ureidopropyltrimethoxysilane), 3- ureidopropyltriethoxysilane, N- second
Epoxide carbonyl -3- aminocarbonyl propyl trimethoxy silane, N- ethoxy carbonyl -3- aminocarbonyl propyl triethoxysilane, tri- ethoxy of N-
Base silane base propyl three stretches second triamine, N- trimethoxysilylpropyl three stretches second triamine, 10- trimethoxy silane base-Isosorbide-5-Nitrae,
Tri- a word used for translation decane of 7-, 10- triethoxysilicane alkyl-Isosorbide-5-Nitrae, tri- a word used for translation decane of 7-, bis- a word used for translation nonyl acetic acid of 9- trimethoxy silane base -3,6-
Ester, bis- a word used for translation nonyl acetate of 9- triethoxysilicane alkyl -3,6-, N- benzyl -3- aminocarbonyl propyl trimethoxy silane, N- benzene first
Base -3- aminocarbonyl propyl triethoxysilane, N- phenyl -3- aminocarbonyl propyl trimethoxy silane, three second of N- phenyl -3- aminocarbonyl propyl
Bis- three second of (ethylene oxide) -3- aminocarbonyl propyl of bis- (the ethylene oxide) -3- aminocarbonyl propyl trimethoxy silanes 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, and preferably 0.5 parts by weight are to 10 parts by weight.
Usage amount based on polymer (A) be 100 parts by weight, the usage amount of additive (C) may generally be 50 parts by weight with
Under, and preferably 0.1 parts by weight are to 30 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 compound (a) and diamine compound (b) are uniformly mixed, a polymer (A) is formed with reaction.Then, will gather
It closes object (A) and solvent (B) is added under conditions of temperature is 0 DEG C to 200 DEG C, and be optionally added additive (C), with stirring
Device continues stirring until dissolution.Preferably, 20 DEG C to 60 DEG C at a temperature of, by solvent (B) be added to polymer composition
In object.
In general, the viscosity of crystal aligning agent of the invention can be 10cps to 90cps at 25 DEG C, preferably can be
15cps to 80cps, and more preferably 20cps to 70cps.
The preparation method of liquid crystal orienting film
The present invention also provides a kind of liquid crystal orienting film, as manufactured by crystal aligning agent above-mentioned.
Preferably, the preparation method of liquid crystal orienting film includes: above-mentioned crystal aligning agent is applied using roller coating method, rotation
The methods of cloth method, print process, ink-jet method (ink-jet), are coated on the surface of a substrate, form a precoated shet, then will be pre-
Coating is by heat treatment (pre-bake treatment) in advance, rear heat treatment (post-bake treatment) and matches
To processing (alignment treatment), liquid crystal orienting film of the invention can be prepared by.
The purpose heated in advance is to make the organic solvent in precoated shet to volatilize.Preferably, at heating in advance
The operating temperature range of reason is 30 DEG C to 120 DEG C, is more preferably 40 DEG C to 110 DEG C, and is more preferably 50 DEG C to 100 DEG C.
Above-mentioned orientation processing is not particularly limited, and the cloth that the fibers such as nylon, artificial silk, cotton class are made into can be used
Material is wrapped on roller, is rubbed with certain orientation and is carried out orientation.Above-mentioned orientation processing is well known to the art person, therefore not
Add to repeat again.
Heat treatment step purpose is to make the polymer in precoated shet to be further carried out dehydration closed-loop (acid imide afterwards
Change) reaction.Preferably, the operating temperature range heated afterwards is 150 DEG C to 300 DEG C, it is more preferably 180 DEG C to 280 DEG C, again
It is more preferably 200 DEG C to 250 DEG C.
The preparation 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 preparation method of liquid crystal display element is therefore, simply just to be stated below well known to the art person.
Referring to Fig. 1, it is the side view for being painted liquid crystal display element according to an embodiment of the invention.Liquid crystal of the present invention
The preferred embodiment of display element 100 includes first unit 110, second unit 120 and liquid crystal cells 130, wherein second unit
120 are spaced relatively with first unit 110, and liquid crystal cells 130 are arranged between first 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 may include 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 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 a kind of individually liquid crystal material or mixing plurality of liquid crystals material.Liquid crystal can
Including but not limited to two amido benzene class liquid crystal, pyridazine (pyridazine) class liquid crystal, schiff base (shiff base) class liquid crystal,
Azoxy (azoxy) class 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 or trade name " C-15 " of (cholesteryl carbonate) etc., " CB-15 " (Merck & Co., Inc.'s system
Make) electricity is lured by force to amido -2- methyl butyl cinnamate etc. to the palm (chiral) agent etc., or to decyloxy benzylidene -
Property (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.
Illustrate application of the invention following with several embodiments, however, it is not to limit the invention, the present invention
Has usually intellectual in technical field, without departing from the spirit and scope of the present invention, when can be used for a variety of modifications and variations.
Detailed description of the invention
In order to have more complete understanding to the embodiment of the present invention and its advantage, referring now to above explanation and cooperate phase
The schema answered.It must be stressed that various features not describe to scale and merely to diagram purpose.Correlative type content is said
It is bright as follows:
[Fig. 1] is the side view for being painted liquid crystal display element according to an embodiment of the invention.
[main element symbol description]
100: liquid crystal display element
110: first unit
112: first substrate
114: electrode
116: the first liquid crystal orienting films
120: second unit
122: the second substrate
126: the second liquid crystal orienting films
130: liquid crystal cells
Specific embodiment
Prepare polymer (A)
Be below prepared according to the 1st table synthesis example A-1-1 to A-1-20 and A-2-1 to A-2-4 and compared with synthesis example A ' -1-
The polymer (A) of 1 to A ' -1-4 and A ' -2-1 to A ' -2-2.
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 p- diamines benzene (b-3-1) of addition 0.541 gram (0.005 mole), 4, the 4 '-of 8.922 grams (0.045 mole)
Two aminodiphenylmethane (b-3-2) and 80 grams of n-methyl-2-pyrrolidone (hereinafter referred to as NMP), and be stirred at room temperature
To dissolution.Then, be added 1.815 grams (0.0025 mole) tetracarboxylic dianhydride's compound (a-1-1) as shown in formula (I-5),
10.361 grams (0.0475 mole) of the equal tetracarboxylic dianhydride of benzene (a-2-1) and 20 grams of NMP, and react 2 hours at room temperature.Instead
After answering, reaction solution is poured into 1500 milliliters of water, polymer is precipitated, filters resulting polymer, and with methanol
Repeat the step of cleaning and filtering three times.Later, product is placed in vacuum drying oven, and is dried with temperature 60 C,
It can be prepared by the polymer (A-1-1) of synthesis example A-1-1.
Synthesis example A-1-2 to A-1-20 and compare synthesis example A ' -1-1 to A ' -1-4
Synthesis example A-1-2 to A-1-20 and to compare synthesis example A ' -1-1 to A ' -1-4 be using poly- with synthesis example A-1-1
The identical preparation method of production method of object is closed, it is different to be in synthesis example A-1-2 to A-1-20 and compare synthesis example A ' -1-
1 to A ' -1-4 is the type and usage amount for changing raw material in polymer, and formula as shown in table 1 below, does not repeat separately herein.
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, be added 0.541 gram (0.005 mole) p- diamines benzene (b-3-1), 8.922 grams (0.045 mole)
4,4 '-two aminodiphenylmethanes (b-3-2) and 80 grams of NMP, and be stirred at room temperature to dissolution.Then, 1.815 grams are added
Tetracarboxylic dianhydride's compound (a-1-1) as shown in formula (I-5), 10.361 grams (0.0475 mole) of the benzene of (0.0025 mole)
Equal tetracarboxylic dianhydride (a-2-1) and 20 grams of NMP.After reacting 6 hours at room temperature, 97 grams of NMP, 2.55 grams of acetic anhydride is added
And 19.75 grams of pyridine, 60 DEG C are warming up to, and persistently stir 2 hours, to carry out imidization reaction.It after reaction, will be anti-
Answer solution to pour into 1500 milliliters of water, polymer is precipitated, filter resulting polymer, and with methanol repeat cleaning and
The step of filtering, is three times.Later, product is placed in vacuum drying oven, and is dried with temperature 60 C, can be prepared by synthesis example
The polymer (A-2-1) of A-2-1.
Synthesis example A-2-2 to A-2-4 and compare synthesis example A ' -2-1 to A ' -2-2
Synthesis example A-2-2 to A-2-4 and to compare synthesis example A ' -2-1 to A ' -2-2 polymerize using with synthesis example A-2-1
The identical preparation method of the production method of object is different to be in synthesis example A-2-2 to A-2-4 and compare synthesis example A ' -2-1 extremely
A ' -2-2 is the type and usage amount for changing raw material in polymer, and formula as shown in table 1 below, does not repeat separately herein.
Prepare crystal aligning agent
It is the crystal aligning agent that embodiment 1 to 24 and comparative example 1 to 8 are prepared according to the 2nd and 3 tables below.
Embodiment 1
Polymer (A-1-1) obtained by aforementioned synthesis example A-1-1 by 100 parts by weight adds to the N- first of 800 parts by weight
In base -2-Pyrrolidone (hereinafter referred to as B-1), and at room temperature, dissolution is continued stirring until with agitating device, can be prepared by reality
Apply the crystal aligning agent of example 1.Resulting crystal aligning agent is evaluated with following evaluation method, result as shown in the 2nd table,
The detection method of its medium viscosity and Young's modulus repeats after holding.
Embodiment 2 to 24 and comparative example 1 to 8
Embodiment 2 to 24 and comparative example 1 to 8 are using system identical with the production method of the crystal aligning agent of embodiment 1
Preparation Method, different being in embodiment 2 to 24 and comparative example 1 to 8 is to change the type and use of raw material in crystal aligning agent
Amount, formula and evaluation result are respectively as shown in the 2nd and 3 tables.
Evaluation method
1. viscosity
At 25 DEG C, using rotational viscometer (model DV-E, BROOKFIELD system), with the condition of 100rpm, measurement
The viscosity (unit cps) of crystal aligning agent obtained by previous embodiment 1 to embodiment 24 and comparative example 1 to comparative example 8.
2. Young's modulus
It, will be obtained by previous embodiment 1 to embodiment 24 and comparative example 1 to comparative example 8 using method of spin coating method
Crystal aligning agent is coated on the glass substrate, to form coating layer.Then, glass substrate is placed on hot plate, and with temperature
The condition that degree is 80 DEG C, the time is 2 minutes carries out pre-baked processing.Then, in circulation baking oven, with temperature be 235 DEG C, the time is
15 minutes conditions bake processing after carrying out.After handling using orientation, the liquid crystal orienting film of thickness 100nm can be made.Then, make
Institute is measured with nanometer indentation test machine (NanoIndenter, model: MTS NanoIndenter G200, Agilent corporation)
The Young's modulus (E, unit GPa) of liquid crystal orienting film is made.Wherein, the probe of nanometer indentation test machine is using triangular pyramidal
Diamond, and measurement frequency be 45MHz, give as security into depth be 20nm, and measuring temperature be 23 DEG C under conditions of measure.It is surveyed
The Young's modulus obtained is evaluated with following benchmark:
◎: E >=8GPa.
Zero: 8GPa > E >=6GPa.
△: 6GPa > E >=4GPa.
×: 4GPa > E.
Wherein, when the evaluation result of the Young's modulus of liquid crystal orienting film is ◎, liquid crystal obtained by this liquid crystal orienting film
Display element does not have any broken bright spot to generate；When the evaluation result of the Young's modulus of liquid crystal orienting film is zero, this LCD alignment
Only there is a little broken bright spot and generates in liquid crystal display element obtained by film；When the evaluation result of the Young's modulus of liquid crystal orienting film is
△ or × when, there are liquid crystal display element obtained by this liquid crystal orienting film a large amount of broken bright spots to generate, and under Young's modulus
Drop, the quantity that broken bright spot generates are more.
As the result of the 2nd table and the 3rd table it is found that when crystal aligning agent of the invention does not include the tetracarboxylic acid as shown in formula (I)
When acid dianhydride compounds (a-1), the Young's modulus of obtained liquid crystal orienting film is too low, and makes the liquid containing the liquid crystal orienting film
The defect that there are crystal display element a large amount of broken bright spots to generate.
It is obtained as the Z representative-CONH- or-NHCO- in tetracarboxylic dianhydride's compound (a-1) as shown in formula (I)
Liquid crystal orienting film have compared with high Young's modulus, and can further improve the broken fleck defect of liquid crystal display element.
Secondly, if the diamine compound (b) of polymer (A) include as shown in formula (II) when diamine compound (b-1), this
Liquid crystal orienting film obtained by crystal aligning agent has compared with high Young's modulus, and can further improve the broken bright of liquid crystal display element
Point defect.
Furthermore if the diamine compound (b) of polymer (A) include as shown in formula (III) when diamine compound (b-2),
Liquid crystal orienting film obtained by this crystal aligning agent has compared with high Young's modulus, and can further improve the broken of liquid crystal display element
Fleck defect.
Need to supplement, though the present invention with specific compound, form, reaction condition, manufacturing process, analysis method or spy
Instrument is determined as illustrating, and illustrates crystal aligning agent of the invention, liquid crystal orienting film and liquid crystal display element, only skill belonging to the present invention
Any tool usually intellectual in art field is it is found that the present invention is not limited thereto, without departing from the spirit and scope of the present invention,
Other compounds, composition, reaction item also can be used in crystal aligning agent, liquid crystal orienting film and liquid crystal display element of the invention
Part, manufacturing process, analysis method or instrument carry out.
Although the present invention is disclosed above with embodiment, however, it is not to limit the invention, the skill belonging to the present invention
Any tool usually intellectual in art field, without departing from the spirit and scope of the present invention, when various change and profit can be made
Decorations, therefore protection scope of the present invention is subject to view the application the scope of the patents institute defender.
Claims (12)
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| JP2020060755A (en) * | 2018-10-04 | 2020-04-16 | Jnc株式会社 | Liquid crystal aligning agent, liquid crystal alignment film, liquid crystal display element, tetracarboxylic dianhydride, polyamic acid and derivative thereof |
| JP2020112655A (en) * | 2019-01-10 | 2020-07-27 | Jnc株式会社 | Liquid crystal aligning agent for optical alignment, liquid crystal aligning film, and liquid crystal display element |
| CN117229506A (en) * | 2023-11-16 | 2023-12-15 | 山东华夏神舟新材料有限公司 | Polyamic acid, polyimide film and preparation method |
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| TWI710585B (en) | 2020-11-21 |
| CN109207170B (en) | 2021-12-10 |
| TW201905039A (en) | 2019-02-01 |
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