CN106047373A - Liquid crystal aligning agent, liquid crystal aligning film, and liqud crystal element - Google Patents
Liquid crystal aligning agent, liquid crystal aligning film, and liqud crystal element Download PDFInfo
- Publication number
- CN106047373A CN106047373A CN201610141247.4A CN201610141247A CN106047373A CN 106047373 A CN106047373 A CN 106047373A CN 201610141247 A CN201610141247 A CN 201610141247A CN 106047373 A CN106047373 A CN 106047373A
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- formula
- aligning agent
- solvent
- weight
- 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
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 208
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 112
- 239000013078 crystal Substances 0.000 title abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 82
- 229920000642 polymer Polymers 0.000 claims abstract description 61
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 claims abstract description 11
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims abstract description 10
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 claims abstract description 8
- VGGNVBNNVSIGKG-UHFFFAOYSA-N n,n,2-trimethylaziridine-1-carboxamide Chemical compound CC1CN1C(=O)N(C)C VGGNVBNNVSIGKG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 6
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 claims abstract description 5
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims abstract description 5
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920005575 poly(amic acid) Polymers 0.000 claims description 87
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- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 42
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- 210000002858 crystal cell Anatomy 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000962 organic group Chemical group 0.000 claims description 7
- 238000010276 construction Methods 0.000 claims description 6
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
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- 238000006243 chemical reaction Methods 0.000 description 52
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- 239000004215 Carbon black (E152) Substances 0.000 description 5
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- 229930195733 hydrocarbon Natural products 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 4
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 4
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- 238000011156 evaluation Methods 0.000 description 4
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- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- SXCHDDWMFBETRA-UHFFFAOYSA-N oxazinan-3-one Chemical compound O=C1CCCON1 SXCHDDWMFBETRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000010422 painting Methods 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
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003229 sclerosing agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003755 zirconium compounds Chemical class 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
- 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
- C09K19/542—Macromolecular compounds
- C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal
-
- 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
-
- 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
Abstract
The invention provides a liquid crystal aligning agent, a liquid crystal aligning film, and a liqud crystal element. The aligning agent contains polymer and at least one type of specific solvent selected from the group which comprises a solvent with phosphorus atoms, N, N-dimethylpropyleneurea, tetrahydro-4H-pyran-4-ketone, tetramethylene sulfoxide, 3-methylcyclohexanone, 4-methylcyclohexanone, a composition represented by a formula (1), a composition represented by a formula (2), a composition represented by a formula (3) and a composition represented by a formula (10). According to the invention, the liquid crystal aligning agent which is not liable to swell a printing plate and is good in printing performance.
Description
Technical field
The present invention relates to a kind of aligning agent for liquid crystal, liquid crystal orientation film and liquid crystal cell.
Background technology
In the past, to develop electrode structure or physical property of liquid crystal molecule of being used etc. different for liquid crystal cell
Multiple type of drive, the most known twisted nematic (Twisted Nematic, TN) type or super twisted to
Row (Super Twisted Nematic, STN) type, vertical orientated (Vertical Alignment, VA)
Type, coplanar switch type (IPS (In-Plane Switching) type), fringing field switching (Fringe Field
Switching, FFS) type, optical-compensation bent (OCB (Optical Compensated Bend)
Type) etc. various liquid crystal cells.These liquid crystal cells have to make the liquid crystal of liquid crystal molecular orientation to take
To film.For the aspect that the various characteristics such as the affinity with regard to thermostability, mechanical strength and liquid crystal are good,
The materials'use polyamic acid of liquid crystal orientation film or polyimides etc..
About aligning agent for liquid crystal, make component of polymer be dissolved in solvent, aligning agent for liquid crystal is coated
Substrate also heats, and is consequently formed liquid crystal orientation film.Herein, the solvent of aligning agent for liquid crystal generally makes
With the high organic solvent of the dissolubility of polymer, such as METHYLPYRROLIDONE or gamma-butyrolacton etc. are non-
Protic polar solvent.It addition, in order to make to coat aligning agent for liquid crystal aligning agent for liquid crystal during substrate
Coating (printing) good, and with tables such as aprotic polar solvent and such as butyl cellosolves
Surface tension is than relatively low organic solvent (referring for example to patent documentation 1 or patent documentation 2).
As the method that aligning agent for liquid crystal is coated substrate, application spin-coating method or flexographic printing process, spray
The various method such as the method for the use of ink and water.Such as flexographic printing process generally uses following hectographic printing device to carry out, institute
State hectographic printing device and aligning agent for liquid crystal is coated the printing comprising the resins such as APR (registered trade mark)
Version, and utilize galley that aligning agent for liquid crystal is transferred on substrate (referring for example to patent documentation 3).
[prior art literature]
[patent documentation]
[patent documentation 1] Japanese Patent Laid-Open 2010-97188 publication
[patent documentation 2] Japanese Patent Laid-Open 2010-156934 publication
[patent documentation 3] Japanese Patent Laid-Open 2001-343649 publication
Summary of the invention
[problem that invention to be solved]
Using the coating improving aligning agent for liquid crystal, as purpose there is appearance in normally used butyl cellosolve
Easily make the tendency of APR resin swelling.Therefore, hectographic printing is being utilized will to comprise the liquid of butyl cellosolve
In the case of brilliant alignment agent coats substrate, have because repeating the coating to galley and galley is swollen
The worry that profit and printing reduce.It addition, as the solvent composition of aligning agent for liquid crystal, it is desirable to even if
It is carried out continuously polymer in the case of printing to be not easy to separate out to printer thus printing (prints continuously
Brush) good.
The present invention is in view of described problem forms, and one of purpose is difficult to make galley swelling for providing one
And the aligning agent for liquid crystal that printing is good.
[solving the means of problem]
Present inventor et al. has carried out actively grinding to realize the problem of prior art as above
Study carefully, it was found that by using specific organic solvent to can solve the problem that described problem as solvent, from
And complete the present invention.Specifically, the present invention following aligning agent for liquid crystal, liquid crystal is provided to take
To film and liquid crystal cell.
On the one hand the present invention's is wherein to provide a kind of aligning agent for liquid crystal, its contain component of polymer, with
And choosing freely has the solvent of phosphorus atoms, a N, N-dimethylpropylene urea, tetrahydrochysene-4H-pyrans-4-ketone,
Chemical combination represented by tetramethylene sulfoxide, 3-methyl cyclohexanone, 4-methyl cyclohexanone, following formula (1)
Compound represented by thing, following formula (2), the compound represented by following formula (3) and following formula
(10) at least one specific solvent in the group that the compound represented by is formed.
[changing 1]
(in formula (1), R4For hydrogen atom or the alkyl of carbon number 1～6；In formula (2), R5Former for hydrogen
Son or the alkyl of carbon number 1～6, R6Alkane diyl for carbon number 2～4；In formula (3), R7～R10Point
Not independently be the organic group of hydrogen atom or monovalence；In formula (10), R11～R13It is separately hydrogen
Atom or the alkyl of carbon number 1～3)
By described specific solvent being used as the solvent composition of aligning agent for liquid crystal, galley can be obtained and be difficult to
The aligning agent for liquid crystal of swelling.Even if it addition, polymer is not easy to analysis in the case of being carried out continuously printing
Go out to printer to make printing good.
A kind of liquid crystal orientation film formed by described aligning agent for liquid crystal of offer is provided.
It addition, another aspect is for providing a kind of liquid possessing the liquid crystal orientation film formed by described aligning agent for liquid crystal
Crystal cell.
The liquid crystal orientation film of the present invention is to use the aligning agent for liquid crystal comprising described specific solvent to be formed,
Therefore can form uniform film and film quality is good.It addition, using described aligning agent for liquid crystal to manufacture liquid
In the case of crystal cell, can reduce printing in a manufacturing process bad, result can realize the yield of product
Improve.
Detailed description of the invention
Hereinafter, to each composition contained in the aligning agent for liquid crystal of the present invention and optionally and arbitrarily allocate
Other compositions illustrate.
<component of polymer>
The aligning agent for liquid crystal of the present invention contains component of polymer.The main framing of polymer is not particularly limited,
Include, for example: polyamic acid, poly amic acid ester, polyimides, polysiloxane, polyester,
Polyamide, polybenzoxazole precursor, polybenzoxazole, cellulose derivative, polyacetals, polyphenyl second
Ene derivative, poly-(styrene-phenylmaleimide) derivant, poly-(methyl) acrylate etc. are main
Skeleton.Additionally, (methyl) acrylate refers to comprise acrylate and methacrylate.
For the aspect that effect is high is improved to printing with regard to specific solvent, in described polymer, liquid crystal
The component of polymer of alignment agent preferably select free polyamic acid, poly amic acid ester, polyimides and
At least one in the group that polysiloxane is formed.Additionally, when the preparation of aligning agent for liquid crystal,
Polymer can be used alone one, it is possible to is applied in combination two or more.
[polyamic acid]
Polyamic acid in the present invention such as can obtain by making tetracarboxylic dianhydride react with diamidogen
?.
(tetracarboxylic dianhydride)
Tetracarboxylic dianhydride for the synthesis of polyamic acid include, for example: aliphatic tetracarboxylic dianhydride,
Ester ring type tetracarboxylic dianhydride, aromatic tetracarboxylic acid's dianhydride etc..As the concrete example of these tetracarboxylic dianhydrides,
Aliphatic tetracarboxylic dianhydride include, for example 1,2,3,4-butane tetracarboxylic acid dianhydrides etc.；
Ester ring type tetracarboxylic dianhydride include, for example: 1,2,3,4-Tetramethylene. tetracarboxylic dianhydride, 1,3-dimethyl
-1,2,3,4-Tetramethylene. tetracarboxylic dianhydrides, 2,3,5-tricarboxylic cyclopentyl acetic acid dianhydrides, 1,3,3a, 4,5,9b-six
Hydrogen-5-(tetrahydrochysene-2,5-dioxo-3-furyl)-naphtho-[1,2-c] furan-1,3-diketone, 1,3,3a, 4,5,9b-six
Hydrogen-8-methyl-5-(tetrahydrochysene-2,5-dioxo-3-furyl)-naphtho-[1,2-c] furan-1,3-diketone, 3-oxa-are double
Ring [3.2.1] octane-2,4-diketone-6-volution-3 '-(oxolane-2 ', 5 '-diketone), 5-(2,5-dioxotetrahydro
-3-furyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, 3,5,6-tri-carboxyl-2-carboxymethyl group norborneols
Alkane-2:3,5:6-dianhydride, dicyclo [3.3.0] octane-2,4,6,8-tetrabasic carboxylic acid 2:4,6:8-dianhydride, 4,9-dioxa three
Ring [5.3.1.02,6] hendecane-3,5,8,10-tetrones, cyclopentanetetracarboxylic's dianhydride etc.；
Aromatic tetracarboxylic acid's dianhydride include, for example pyromellitic acid anhydride etc.；In addition, also can make
With the tetracarboxylic dianhydride described in Japanese Patent Laid-Open 2010-97188 publication.Additionally, tetrabasic carboxylic acid two
Acid anhydride can be used alone one or be applied in combination two or more.
Just can make the good aspect of electrical characteristics and to can further improve polymer phase specific molten for comprising
The dissolubility of the solvent of agent, can further improve the aspect improving effect of printing for, in synthesis
The tetracarboxylic dianhydride used preferably comprises ester ring type tetracarboxylic dianhydride.It addition, ester ring type tetracarboxylic acid
In acid dianhydride, preferably comprise choosing freely 2,3,5-tricarboxylic cyclopentyl acetic acid dianhydrides, 1,3,3a, 4,5,9b-
Hexahydro-5-(tetrahydrochysene-2,5-dioxo-3-furyl)-naphtho-[1,2-c] furan-1,3-diketone, 1,3,3a, 4,5,9b-
Hexahydro-8-methyl-5-(tetrahydrochysene-2,5-dioxo-3-furyl)-naphtho-[1,2-c] furan-1,3-diketone, dicyclo
[3.3.0] octane-2,4,6,8-tetrabasic carboxylic acid 2:4,6:8-dianhydride and 1,2,3,4-Tetramethylene. tetracarboxylic dianhydrides are formed
Group at least one, particularly preferably comprise choosing freely 2,3,5-tricarboxylic cyclopentyl acetic acid two
Acid anhydride, dicyclo [3.3.0] octane-2,4,6,8-tetrabasic carboxylic acid 2:4,6:8-dianhydride and 1,2,3,4-Tetramethylene. tetracarboxylic dianhydrides
At least one in the group formed.
Comprising choosing freely 2,3,5-tricarboxylic cyclopentyl acetic acid dianhydrides, dicyclo [3.3.0] octane-2,4,6,8-
Tetrabasic carboxylic acid 2:4,6:8-dianhydride and 1, at least in the group that 2,3,4-Tetramethylene. tetracarboxylic dianhydrides are formed
In the case of planting as tetracarboxylic dianhydride, the tetrabasic carboxylic acid two used in the synthesis relative to polyamic acid
The total amount of acid anhydride, preferably 10 moles more than % of the total content of these compounds, more preferably 20
Mole %～100 moles of %.
(diamidogen)
Diamidogen used in the synthesis of polyamic acid include, for example: aliphatic diamine, ester ring type two
Amine, aromatic diamine, diaminourea organosiloxane etc..As the concrete example of these diamidogen, aliphatic
Diamidogen include, for example: m-xylene diamine, 1,3-propane diamine, tetra-methylenedimine, five methylene diamine,
Hexamethylene diamine, 1, double (amino methyl) hexamethylene of 3-etc.；Ester ring type diamidogen include, for example Isosorbide-5-Nitrae-two
Aminocyclohexane, 4,4 '-di-2-ethylhexylphosphine oxide (cyclo-hexylamine) etc.；
Aromatic diamine include, for example: p-phenylenediamine, 4,4 '-diaminodiphenyl-methane, 4,4 '-diamino
Base diphenylsulfide, 1,5-diaminonaphthalene, 2,2 '-dimethyl-4,4 '-benzidine, 2,2 '-bis-(fluoroforms
Base)-4,4 '-benzidine, 4，4′-diaminodipohenyl ether, 1, double (4-amino-benzene oxygen) propane of 3-, 9,9-
Double (4-aminophenyl) fluorenes, 2, double [4-(4-amino-benzene oxygen) phenyl] HFC-236fa of 2-, 4,4 '-(to phenylene
Two isopropylidenes) dianil, Isosorbide-5-Nitrae-bis-(4-amino-benzene oxygen) benzene, DAP, 3,6-diaminourea
Carbazole, N, N '-bis-(4-aminophenyl)-benzidine, Isosorbide-5-Nitrae-bis--(4-aminophenyl)-piperazine, 1-(4-aminobenzene
Base)-2,3-dihydro-1,3,3-trimethyl-1H-indenes-5-amine, 1-(4-aminophenyl)-2,3-dihydro-1,3,3-trimethyls
-1H-indenes-6-amine, 3,5-diaminobenzoic acid, cholesteric alkyl oxy-3,5-diaminobenzene, cholesteryl oxygen
Base-3,5-diaminobenzene, cholesteric alkyl oxy-2,4-diaminobenzene, 3,5-diaminobenzoic acid cholesteric alkyl
Ester, 3,5-diaminobenzoic acid cholesteryl ester, 3,5-diaminobenzoic acid lanostane base ester, 3,6-
Double (4-amino benzoyl epoxide) cholestane, 4-(4 '-trifluoromethoxy benzoyloxy) cyclohexyl-3,5-
Diaminobenzoic acid ester, 1, double (4-((aminophenyl) methyl) phenyl)-4-heptylcyclohexane of 1-, 1,1-is double
(4-((aminophenyl) methyl) phenyl)-4-(4-heptyl cyclohexyl) hexamethylene, 2,4-diamino-N, N-bis-allyl
Base aniline, 4-aminobenzyl amine, N-[4-(2-amino-ethyl) phenyl] benzene-Isosorbide-5-Nitrae-diamidogen, N-[4-(amino first
Base) phenyl] benzene-Isosorbide-5-Nitrae-diamidogen, diamidogen containing cinnamic acid structure and following formula (D-1)
[changing 2]
(in formula (D-1), XIAnd XIIIt is separately singly-bound ,-O-, *-COO-, *-OCO-
Or *-NH-CO-(wherein, with associative key and the diamino-phenyl bond of " * "), RIAnd RIIRespectively
Independently be the alkane diyl of carbon number 1～3, a is 0 or 1, and b is the integer of 0～2, and c is 1～20
Integer, n is 0 or 1, and m is 0 or 1；Wherein, it is 0 during a and b difference, at XIFor *-NH-CO-
In the case of, n is 0)
Represented compound etc.；
Diaminourea organosiloxane include, for example 1, double (3-aminopropyl)-tetramethyl disiloxanes of 3-etc.；
In addition, it be also possible to use the diamidogen described in Japanese Patent Laid-Open 2010-97188 publication.Additionally,
These diamidogen can be used alone one or be applied in combination two or more.
The concrete example of the compound represented by described formula (D-1) include, for example following formula (D-1-1)～
Compound etc. represented by formula (D-1-4) difference.
[changing 3]
Diamidogen for the synthesis of polyamic acid preferably comprises 30 moles of % relative to whole diamidogen
Above aromatic diamine, more preferably comprises 50 moles of more than %, particularly preferably comprises 80
Mole more than %.
(synthesis of polyamic acid)
Polyamic acid optionally can adjust with molecular weight by making tetracarboxylic dianhydride as above and diamidogen
Agent is reacted together and is obtained.It is supplied to tetracarboxylic dianhydride and the diamidogen of the synthetic reaction of polyamic acid
Use ratio preferably relative to amino 1 equivalent of diamidogen, the anhydride group of tetracarboxylic dianhydride becomes
0.2 equivalent～the ratio of 2 equivalents.Molecular weight regulator include, for example: maleic anhydride, adjacent benzene
The single acid anhydride of the acid such as dicarboxylic acid anhydride, itaconic anhydride；The monoamine compounds such as aniline, cyclo-hexylamine, n-butylamine；
The monoisocyanate compound such as carbanil, naphthyl isocyanate etc..Relative to the tetrabasic carboxylic acid used
Total 100 weight portion of dianhydride and diamidogen, the use ratio of molecular weight regulator is preferably set to
Below 20 weight portions.
The synthetic reaction of polyamic acid is preferably carried out in organic solvent.Reaction temperature now is excellent
Choosing is-20 DEG C～150 DEG C, preferably 0.1 hour～24 hours response time.
Organic solvent used in reaction include, for example: aprotic polar solvent, phenol system solvent,
Alcohol, ketone, ester, ether, halogenated hydrocarbon, hydrocarbon etc..Particularly preferred organic solvent is preferably with being selected from
By METHYLPYRROLIDONE, N,N-dimethylacetamide, DMF, dimethyl Asia
Sulfone, gamma-butyrolacton, tetramethylurea, HMPA, metacresol, xylenol, halogenation phenol and
More than one in the group that specific solvent shown below is formed are as solvent, or use these molten
More than one of matchmaker are with other organic solvents (such as butyl cellosolve, diethylene glycol diethyl ether etc.)
Mixture.The usage amount (a) of organic solvent is preferably set to the total amount of tetracarboxylic dianhydride and diamidogen
B () becomes 0.1 weight %～the amount of 50 weight % relative to the total amount (a+b) of reaction solution.
Obtain the reaction solution dissolved by polyamic acid in the manner.Described reaction is molten
Liquid can be supplied directly to the preparation of aligning agent for liquid crystal, it is also possible to by polyamic acid contained in reaction solution
The preparation of aligning agent for liquid crystal it is available to after separation.
[polyimides]
Polyimides in the present invention such as can be by taking off the polyamic acid synthesized in this way
Water blockage ring and imidizate obtains.Polyimides can be to be had the polyamic acid as its precursor
Some amic acid structures all carry out the complete acid imide compound of dehydration closed-loop, it is also possible to be the most right
A part for amic acid structure carries out dehydration closed-loop and makes amic acid structure and imide ring structure and deposit
Part acid imide compound.The acid imide rate preferably more than 30% of the polyimides in the present invention,
More preferably 40%～99%, and then preferably 50%～99%.Described acid imide rate is relative
In the total of quantity of quantity and imide ring structure of the amic acid structure of polyimides, with percentage rate
Represent the ratio shared by the quantity of imide ring structure.Herein, a part for imide ring can also
It it is different imide ring.
The dehydration closed-loop of polyamic acid is carried out preferably with following methods: carry out polyamic acid
The method of heating；Or polyamic acid is dissolved in organic solvent, described solution adds dehydrant
And dehydration closed-loop catalyst and the method that optionally carries out heating.Wherein it is preferred that the side utilizing the latter
Method.
The solution of polyamic acid add in the method for dehydrant and dehydration closed-loop catalyst, dehydrant
Such as can use the anhydride such as acetic anhydride, propionic andydride, trifluoroacetic anhydride.Amide relative to polyamic acid
1 mole of acid structure, the usage amount of dehydrant is preferably set to 0.01 mole～20 moles.Dehydration
Ring-closing catalyst such as can use the tertiary amines such as pyridine, collidine, two picolins, triethylamine.
Relative to the dehydrant used 1 mole, O.01 the usage amount of dehydration closed-loop catalyst is preferably set to
Mole～10 moles.Organic solvent for dehydration closed-loop reaction can be enumerated as polyamic acid
The organic solvent of synthesis and the organic solvent that illustrates.The reaction temperature of dehydration closed-loop reaction is preferably
0 DEG C～180 DEG C, preferably 1.0 hours～120 hours response time.
Obtain the reaction solution containing polyimides in this way.Described reaction solution can directly provide
To the preparation of aligning agent for liquid crystal, it is also possible to autoreaction solution is removed dehydrant and dehydration closed-loop catalyst
After be available to the preparation of aligning agent for liquid crystal, it is also possible to be available to liquid crystal after being separated by polyimides and take
To the preparation of agent.These purification process can be carried out according to known method.In addition, polyamides is sub-
Amine can also be obtained by the imidizate of poly amic acid ester.
[poly amic acid ester]
Poly amic acid ester in the present invention such as may utilize following methods and obtains: [I] makes by described conjunction
Become the polyamic acid and esterifying agent (such as methanol or ethanol, DMF reacted and obtain
Diethyl acetal etc.) method that carries out reacting；[II] make tetrabasic carboxylic acid diester and diamidogen in organic solvent,
At suitable dehydration catalyst (such as 4-(4,6-dimethoxys-1,3,5-triazines-2-base)-4-methyl morpholine
Halogenide, phosphorus system condensing agent etc.) in the presence of carry out the method reacted；[III] makes tetrabasic carboxylic acid diester dihalo-
Compound and diamidogen are in organic solvent, at suitable alkali (such as pyridine, triethylamine, sodium hydroxide
Deng) in the presence of carry out the method etc. reacted.
Poly amic acid ester contained in aligning agent for liquid crystal can only have amic acid esters structure, it is also possible to is
Amic acid structure and amic acid esters structure the partial esterification thing deposited.Additionally, poly amic acid ester is dissolved
Reaction solution can be supplied directly to the preparation of aligning agent for liquid crystal, it is also possible to by institute in reaction solution
The poly amic acid ester contained is available to the preparation of aligning agent for liquid crystal after separating.
Polyamic acid, poly amic acid ester and the polyimides obtained in this way is preferably when by it
There is when making the solution of concentration 10 weight % the solution viscosity person of 10mPa s～800mPa s, more excellent
Choosing is the solution viscosity person with 15mPa s～500mPa s.Additionally, the solution of described polymer
Viscosity (mPa s) is to use E type rotating cylinder viscometer to the good solvent using described polymer at 25 DEG C
The polymer of concentration 10 weight % prepared by (such as gamma-butyrolacton, METHYLPYRROLIDONE etc.)
Solution be measured obtained by value.
Sub-about polyamic acid contained in the aligning agent for liquid crystal of the present invention, poly amic acid ester and polyamides
Amine, utilizes gel permeation chromatography (Gel Permeation Chromatography, GPC) to measure
The weight average molecular weight preferably 500～100,000 of polystyrene conversion, more preferably
1,000～50,000.
[polysiloxane]
Polysiloxane in the present invention such as can be by preferably fitting water-disintegrable silane compound
When organic solvent, water and catalyst in the presence of be hydrolyzed or hydrolytic condensation and obtain.
Water-disintegrable silane compound used in the synthesis of polysiloxane include, for example: four
Methoxy silane, tetraethoxysilane, MTMS, MTES, benzene
Base trimethoxy silane, phenyl triethoxysilane, trimethoxysilylpropyl succinic anhydrides, two
The alkoxysilane compound containing trialkylsilyl group in molecular structure such as methyl dimethoxysilane, dimethyldiethoxysilane；3-mercaptopropyi
Trimethoxy silane, 3-Mercaptopropyltriethoxysilane, mercapto methyl trimethoxy silane, sulfydryl first
Ethyl triethoxy silicane alkane, 3-ureido-propyl trimethoxy silane, 3-TSL 8330,3-
The alkane of the nitrogenous sulfur such as aminopropyltriethoxywerene werene, N-(3-Cyclohexylamino) propyl trimethoxy silicane
TMOS compound；3-glycidoxypropyltrimewasxysilane, 3-glycidoxypropyl
Triethoxysilane, 3-glycidoxypropyl dimethoxysilane, 2-(3,4-epoxycyclohexyl)
The silicon containing epoxy radicals such as ethyl triethoxysilane, 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane
Hydride compounds；3-(methyl) acryloxypropyl trimethoxy silane, 3-(methyl) acryloxy third
Ylmethyl dimethoxysilane, 3-(methyl) acryloxypropyl diethoxy silane, vinyl
Trimethoxy silane, to the alkoxy silane chemical combination containing unsaturated bond such as styryl trimethoxy silane
Thing etc..Hydrolysable silanes compound can be used alone the one in these silane compounds or be applied in combination
Two or more.Additionally, " (methyl) acryloxy " refers to comprise " acryloxy " and " methyl
Acryloxy ".
Described hydrolysis-condensation reaction is by making one or more of silane compound as described
Preferably react in the presence of suitable catalyst and organic solvent with water and carry out.When reaction, phase
For silane compound (total amount) 1 mole, the use ratio of water preferably 1 mole～30 is rubbed
You.The catalyst used include, for example: acid, alkali metal compound, organic base (such as three second
Base amine or tetramethyl ammonium hydroxide etc.), titanium compound, zirconium compounds etc..The usage amount of catalyst according to
The reaction conditions such as the kind of catalyst, temperature etc. and different, should suitably set, such as relative to
The total amount of silane compound, preferably 0.01 times mole～3 times moles.Used is organic molten
Matchmaker include, for example hydrocarbon, ketone, ester, ether, alcohol etc., in these organic solvents, it is preferred to use non-
Water solublity or the organic solvent of slightly water-soluble.Total relative to the silane compound used in reaction
100 weight portions, use ratio preferably 50 weight portion of organic solvent～1,000 weight portion.
Described hydrolysis-condensation reaction the most such as utilizes oil bath etc. to carry out heating to implement.Now,
Heating-up temperature is preferably set to less than 130 DEG C, is preferably set to heat time heating time 0.5 hour～12 little
Time.After the completion of reaction, can obtain by autoreaction liquid divides the organic solvent layer taken remove solvent
Polysiloxane.
It is being applied to TN type, STN type or the aligning agent for liquid crystal of vertical alignment-type liquid crystal display device
In the case of, liquid crystal aligning base can be imported on the side chain of polysiloxane or there is light orientation
The specific base such as the base of structure.Synthesis has the method for the polysiloxane of these specific bases on side chain
It is not particularly limited, include, for example following methods: to the silane compound containing epoxy radicals or containing ring
The silane compound of epoxide and the mixture of other silane compounds are hydrolyzed and are condensed and synthesize and have ring
The polysiloxane of epoxide, then make the polysiloxane containing epoxy radicals of gained with have described
The carboxylic acid of specific base carries out the method etc. reacted.Polysiloxane containing epoxy radicals and the reaction of carboxylic acid
Can carry out according to known method.
The weight average molecular weight utilizing polystyrene conversion that GPC measures of polysiloxane
(Mw) 500～100 preferably it are in, the scope of 000, preferred it is in 1,000～30,000
Scope, and then preferably 1,000～20,000.If the weight average molecular weight of polysiloxane
It is in described scope, then easily operates when manufacturing liquid crystal orientation film, and the liquid crystal orientation film of gained
There is the sufficient strength of materials and characteristic.
In the aligning agent for liquid crystal of the present invention, relative to the total amount of the component of polymer in aligning agent for liquid crystal,
Select in the group that free polyamic acid, poly amic acid ester, polyimides and polysiloxane are formed
Content ratio (containing being total amount in the case of two or more) preferably 50 weights of polymer
Amount more than %, more than more preferably 60 weight %.It addition, the most more preferably obtain the effect of the present invention
Fruit viewpoint for, component of polymer preferably comprise choosing free polyamic acid, poly amic acid ester and
At least one in the group that polyimides is formed.Relative to the component of polymer in aligning agent for liquid crystal
Total amount, the total of polyamic acid, poly amic acid ester and polyimides in aligning agent for liquid crystal contains
More than ratio preferably 40 weight %, more than more preferably 60 weight %.
<solvent>
The aligning agent for liquid crystal of the present invention is be dispersed or dissolved in solvent by component of polymer aqueous
Compositions.Described aligning agent for liquid crystal contains choosing freely to be had the solvent of phosphorus atoms and (hereinafter also referred to " contains
Phosphorus solvent "), N, N-dimethylpropylene urea, tetrahydrochysene-4H-pyrans-4-ketone, tetramethylene sulfoxide, 3-
Compound represented by methyl cyclohexanone, 4-methyl cyclohexanone, described formula (1), described formula (2) institute
Compound represented by the compound of expression, described formula (3) and the chemical combination represented by described formula (10)
At least one specific solvent in the group that thing is formed is as solvent.
[phosphorous solvent]
As long as the compound that phosphorous solvent has at least one phosphorus atoms in intramolecular then there is no limit especially
Fixed, preferably select free following formula (P-1)～formula (P-4) respectively represented by compound formed
Group at least one.
[changing 4]
(in formula (p-1)～formula (p-4), X1And Y1It is separately oxygen atom or sulphur atom；
R1For hydrogen atom or the alkyl of the monovalence of carbon number 1～10, R2For hydrogen atom or the organic group of monovalence；Its
In, R1With R2Can mutually bond and form ring；R3It is separately hydrogen atom or carbon number 1～6
Alkyl, is binding on two R of nitrogen-atoms3Can mutually bond and form the nitrogenous of monovalence together with nitrogen-atoms
Heterocyclic radical；Wherein, R1And R2It is asynchronously hydrogen atom, R2And R3It it is asynchronously hydrogen atom；m、n、
K and j is separately the integer of 1～3；In the case of m, n, k, j are 2 or 3, in formula
Multiple R1、R3May be the same or different each other, in the case of m, n, k, j are 1, in formula
Multiple R2May be the same or different each other)
Herein, in this manual, so-called " alkyl " be comprise chain alkyl, ester ring type alkyl and
The implication of aromatic hydrocarbyl.So-called " chain alkyl ", refers to not comprise on main chain circulus, and
It is the straight-chain alkyl and branch-like alkyl being only made up of chain structure.Wherein it is possible to be saturated,
Can also be unsaturated.So-called " ester ring type alkyl ", refers to only comprise the structure conduct of ester ring type hydrocarbon
Ring structure and without the alkyl of aromatic ring structure.Wherein, it is not necessary to only by the structure of ester ring type hydrocarbon
Constituted, also comprised the alkyl in one part with chain structure.So-called " aromatic hydrocarbyl ",
Refer to the alkyl comprising aromatic ring structure as ring structure.Wherein, it is not necessary to only by aromatic ring structure
Constituted, it is also possible in one part, comprise chain structure or the structure of ester ring type hydrocarbon.It addition,
In this specification, so-called " organic group ", refer to comprise the base of carbon atom, it is also possible to comprise in the structure
Hetero atom.
In described formula (p-1), R1The alkyl of monovalence of carbon number 1～10 include, for example: methyl,
The straight-chain such as ethyl, propyl group, butyl, amyl group, hexyl, heptyl, octyl group, nonyl, decyl or point
Prop up the alkyl of shape；The thiazolinyl such as vinyl, pi-allyl；The alkynyls such as acetenyl；Cyclopenta, cyclohexyl,
The cycloalkyl such as methylcyclohexyl；The aryl such as phenyl, tolyl, xylyl；Benzyl, phenethyl,
The aralkyl etc. such as styryl.In described base, R1The preferably alkyl of carbon number 1～3.
R2The organic group of monovalence include, for example: the alkyl of the monovalence of carbon number 1～10, at described hydrocarbon
Comprise the base containing heteroatomic base between the carbon-carbon bond of base, described alkyl forms with containing heteroatomic base bond
Base, at least one hydrogen atom of these bases be substituted base that base replaces, cyano group, formoxyl etc..
Herein, so-called containing heteroatomic base, refer to the base with more than heteroatomic bivalence, such as may be used
Enumerate :-O-,-CO-,-COO-,-CONRa-(RaFor hydrogen atom or the alkyl of carbon number 1～6, with
Under identical) ,-NRa-, the nitrogen-atoms of trivalent ,-NRaCONRa-、-OCONRa-、-S-、-COS-、
-OCOO-、-SO2-etc..Substituent group include, for example: halogen atom, nitro, cyano group, hydroxyl etc..
In described base, R2The preferably alkyl of carbon number 1～6 or the aryl of carbon number 6 or 7.
R3The alkyl of carbon number 1～6 can be that straight-chain is alternatively branch-like.Two R3Mutually bond and
The nitrogen heterocycle of monovalence formed can be enumerated and will be binding on nitrogen-atoms that described nitrogen heterocyclic ring had
Base etc. after hydrogen atom removing.Described nitrogenous heterocyclic concrete example include, for example pyridine ring, piperidine ring
Deng, it is possible to there is on these loop sections the such as substituent group such as halogen atom, alkyl.R3Preferably
The alkyl of carbon number 1～3, more preferably methyl.X1And Y1Preferably oxygen atom.m、n、k
And j preferably 2 or 3, more preferably 3.
For the higher aspect of improvement effect of printing, in described formula (p-1)～formula (p-4),
Phosphorous solvent is preferably selected from the compound represented by described formula (p-1) and described formula (p-3) institute table
At least one in the formed group of compound shown, represented by the most described formula (p-1)
Compound.
The preferred concrete example of phosphorous solvent include, for example following formula (p-1-1)～formula (p-1-7), formula
(p-3-1) compound etc. and represented by formula (p-3-2) difference.
[changing 5]
For the aspect that printing is better, in described compound, phosphorous solvent is particularly preferably
Described formula (p-1-1)～formula (p-1-4) and formula (p-3-1) respectively represented by compound.Additionally,
Phosphorous solvent can be used alone one or be applied in combination two or more.
[compound represented by described formula (1)]
In described formula (1), R4The alkyl of carbon number 1～6 include, for example methyl, ethyl, propyl group,
Butyl etc., these alkyl can be that straight-chain is alternatively branch-like.Compound represented by described formula (1)
Concrete example include, for example 4-formyl-morpholine, 4-acetylmorpholine etc., be wherein particularly preferably
4-formyl-morpholine.One or combination additionally, the compound represented by described formula (1) can be used alone
Use two or more.
[compound represented by described formula (2)]
In described formula (2), R5The illustration of alkyl of carbon number 1～6 can apply described formula (1)
R4Explanation.R6The alkane diyl of carbon number 2～4 include, for example ethylidene, glyceryl, fourth diyl,
These alkane diyls can be that straight-chain is alternatively branch-like.Compound represented by described formula (2) concrete
Example include, for example: 3-methyl-2-oxazolidone, 3-ethyl-2-oxazolidone, 3-isopropyl-2-azoles
Alkanone, N-methyl-2-piperazine alkanone (oxazinanone) etc., the most particularly preferably 3-methyl-2-
Oxazolidone.The one or the be applied in combination two additionally, compound represented by described formula (2) can be used alone
More than Zhong.
[compound represented by described formula (3)]
In described formula (3), R7～R10The organic group of monovalence include, for example: carbon number 1～10
Alkyl, comprise between the carbon-carbon bond of described alkyl the base containing heteroatomic base, described alkyl with containing miscellaneous former
The base of base bond of son, at least one hydrogen atom of these bases are substituted the base etc. that base replaces.
About the concrete example containing heteroatomic base and substituent group, the R in described formula (p-1) can be applied2Explanation.
Additionally, R7～R10May be the same or different each other.R7～R10Preferably hydrogen atom, carbon number 1～5
Alkyl or-CORb(RbFor hydrogen atom or the alkyl of carbon number 1～3).R7And R10One of which excellent
Choosing is-CORb。
The concrete example of the compound represented by described formula (3) include, for example 2 furan carboxyaldehyde, 3-furan
Formaldehyde, 5-methyl-2 furan carboxyaldehyde, 5-methyl-3-furtural, 4-methyl-2 furan carboxyaldehyde, 5-hydroxyl
Methyl-2 furan carboxyaldehyde etc., the most particularly preferably 5-methyl-2 furan carboxyaldehyde.Additionally, described formula
(3) compound represented by can be used alone one or be applied in combination two or more.
[compound represented by described formula (10)]
In described formula (10), R11～R13The alkyl of carbon number 1～3 include, for example methyl, ethyl,
N-pro-pyl, isopropyl, wherein it is preferred that methyl.The tool of the compound represented by described formula (10)
Style include, for example lactamide, N, N-dimethyl lactamide, N, N-diethyl lactamide, N-methyl
-N-propyl group lactamide, N-ethyl lactamide, N-isopropyl lactamide etc., be wherein particularly preferably
N, N-dimethyl lactamide.The one additionally, the compound represented by described formula (10) can be used alone
Or it is applied in combination two or more.
For the aspect that printing (particularly continuous printing) is better, in described compound,
Freely phosphorous solvent, N, N-dimethylpropylene urea, described formula is preferably selected as specific solvent
(1) in the group that the compound represented by and the compound represented by described formula (2) are formed extremely
Few one.The one or be used in combination of two or more additionally, specific solvent can be used alone.
[other solvents]
The aligning agent for liquid crystal of the present invention also can be containing the solvent beyond specific solvent (hereinafter also referred to as " its
His solvent ").The concrete example of other solvents include, for example: N-ethyl-2-pyrrolidone, N-(positive third
Base)-2-Pyrrolidone, N-isopropyl-2-Pyrrolidone, N-(normal-butyl)-2-Pyrrolidone, N-(tertiary fourth
Base)-2-Pyrrolidone, N-(n-pentyl)-2-Pyrrolidone, N-methoxy-propyl-2-Pyrrolidone, N-
Ethoxyethyl group-2-Pyrrolidone, N-methoxybutyl-2-Pyrrolidone, 3-butoxy-N, N-dimethyl
Propane amide, 3-methoxyl group-N, N-dimethylpropane amide, 3-hexyl epoxide-N, N-dimethylpropane acyl
Amine, isopropoxy-N-isopropyl-propionic acid amide., n-butoxy-N-isopropyl-propionic acid amide., 1,3-dimethyl-2-
Imidazolidinone, N, N '-dimethylpropylene urea, tetramethylurea, METHYLPYRROLIDONE, γ-Ding Nei
Ester, δ-valerolactone, gamma-valerolactone, γ-hexalactone, N, N-diethyl acetamide, butyrolactam, N, N-
Dimethylformamide, N,N-dimethylacetamide, glycol monoethyl ether, butyl lactate, butyl acetate,
Methoxy methyl propionate, ethoxyl ethyl propionate, ethylene glycol monomethyl ether, ethylene glycol, ethylene glycol-just
Propyl ether, ethylene glycol-diisopropyl ether, ethylene glycol-n-butyl ether (butyl cellosolve), glycol dimethyl ether, second
Glycol ether acetas, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether second
Acid esters, diethylene glycol monoethyl ether acetas, dipropylene glycol monomethyl ether (dipropylene glycol
Monomethyl ether, DPM), diisobutyl ketone, isoamyl propionate, isoamyl isobutyrate, carbon
Acid ethyl, propylene carbonate etc..Additionally, other solvents can be used alone a kind of described compound or
It is used in mixed way two or more.
About specific solvent, whole solvents contained in aligning agent for liquid crystal can be set to specific solvent,
Also a part can be set to specific solvent.Relative to total scale of construction of solvent contained in aligning agent for liquid crystal,
The content ratio (being its total amount in the case of use is two or more, the most identical) of specific solvent
Preferably 1 weight %～80 weight %, more preferably 5 weight %～70 weight %, and then preferably
Be 10 weight %～60 weight %, particularly preferably 20 weight %～60 weight %.
<other compositions>
The aligning agent for liquid crystal of the present invention contains component of polymer as described and solvent, the most also may be used
Containing other compositions.Other compositions described include, for example: has at least one epoxy radicals in intramolecular
Compound, functional silanes compound, photopolymerizable compound, surfactant, filler,
Defoamer, sensitizer, dispersant, antioxidant, contiguity auxiliary agent, antistatic additive, leveling agent, anti-
Microbial inoculum etc..The allotment ratio of these compositions can not hinder the present invention's according to the compound allocated
Set aptly in the range of effect.
Solid component concentration (the one-tenth beyond the solvent of aligning agent for liquid crystal in the aligning agent for liquid crystal of the present invention
The ratio that the total weight divided is shared in the gross weight of aligning agent for liquid crystal) consider viscosity, volatility etc.
And select aptly, preferably 1 weight %～the scope of 10 weight %.That is, the liquid crystal of the present invention
Alignment agent is by coating substrate surface in aftermentioned mode, and preferably heats, and is formed
As the film of liquid crystal orientation film or become the film of liquid crystal orientation film, but now, dense at solid constituent
Degree is less than in the case of 1 weight %, and the thickness of film becomes too small and becomes to be difficult to obtain good liquid crystal
Alignment films.On the other hand, in the case of solid component concentration is more than 10 weight %, the thickness of film
Become excessive and be difficult to obtain good liquid crystal orientation film, and the viscosity that there is aligning agent for liquid crystal increases
And make the tendency that coating characteristics reduces.
The scope of particularly preferred solid component concentration is according to institute when being coated on substrate by aligning agent for liquid crystal
Use method and different.Such as in the case of utilizing spin-coating method, particularly preferably solid constituent
Concentration is 1.5 weight %～the scope of 4.5 weight %.In the case of utilizing flexographic printing process, especially
Preferably solid component concentration is set to 3 weight %～the scope of 9 weight %, and thus solution is glued
Degree is set to 12mPa s～the scope of 50mPa s.In the case of utilizing ink-jet method, particularly preferably
Solid component concentration is set to 1 weight %～the scope of 5 weight %, and thus solution viscosity is set to 3
MPa s～the scope of 15mPa s.Prepare the temperature preferably 10 DEG C～50 DEG C during aligning agent for liquid crystal,
More preferably 20 DEG C～30 DEG C.
<liquid crystal orientation film and liquid crystal cell>
The liquid crystal orientation film of the present invention is to be formed by the aligning agent for liquid crystal prepared in this way.It addition,
The liquid crystal orientation film that the liquid crystal cell of the present invention possesses the described aligning agent for liquid crystal of use and formed.Liquid crystal cell
The drive pattern of the liquid crystal in part is not particularly limited, can be applicable to TN type, STN type, IPS type,
FFS type, VA type, multidomain vertical orientation (Multi-domain Vertical Alignment, MVA)
The multiple driving moulds such as type, polymer stabilizing orientation (Polymer sustained alignment, PSA) type
Formula.The liquid crystal cell of the present invention such as may utilize and comprises the following steps that the method for 1～step 3 manufactures.
About step 1, the substrate used according to desired drive pattern is different.Step 2 and step 3
In each drive pattern general.
[step 1: the formation of film]
First, substrate is coated with the aligning agent for liquid crystal of the present invention, then coated face is heated,
On substrate, thus form film.
(1-1) TN type, STN type, VA type, MVA type or the liquid crystal cell of PSA type are being manufactured
In the case of, the substrate that two pieces are provided with the nesa coating patterned is set to a pair, respectively
On the formation face of the transparent conductive film in substrate, utilize preferably flexographic printing process, spin-coating method,
Rolling method or ink jet printing method are respectively coated aligning agent for liquid crystal.Substrate such as can use: float glass (float
Glass), the glass such as soda-lime glass；Comprise polyethylene terephthalate, polybutylene terephthalate,
The transparency carrier of the plastics such as polyether sulfone, Merlon, poly-(ester ring type alkene).In one of them of substrate
Nesa coating set on face can use and comprise stannum oxide (SnO2) nesa (NESA) film (beautiful
PPG register of company of state trade mark), comprise indium oxide-tin oxide (IN2O3-SnO2) tin indium oxide
(Indium Tin Oxide, ITO) film etc..
After coating of liquid crystalline alignment agent, for the purpose of dropping liquid of preventing be coated with alignment agent etc., preferably
It is to implement preparation heating (prebake conditions).Prebake conditions temperature preferably 30 DEG C～200 DEG C, during prebake conditions
Between preferably 0.25 minute～10 minutes.Thereafter, for the purpose of solvent is removed completely, additionally regard
Need the amic acid structure being present in polymer to carry out hot-imide as purpose, and implement to forge
Burn (baking afterwards) step.Calcining heat (rear baking temperature) preferably 80 DEG C～300 DEG C now,
Post-bake times preferably 5 minutes～200 minutes.The thickness of the film formed in this way is preferred
It is 0.001 μm～1 μm, more preferably 0.005 μm～0.5 μm.
(1-2) in the case of manufacturing IPS type or FFS type liquid crystal display cells, be provided with comprise with
Nesa coating that interdigitated electrode structure is patterned or the electrode forming surface of the substrate of the electrode of metal film,
It is respectively coated aligning agent for liquid crystal, then to respectively with on one of them face of the opposite substrate being not provided with electrode
Coated face heats, and is consequently formed film.About the substrate now used and nesa coating
Heating condition after material, coating process, coating, thickness etc. are identical with described (1-1).Metal
Film such as can use the film comprising the metals such as chromium.
Under the either case of described (1-1) and (1-2), it is all to be taken by coating of liquid crystalline on substrate
After agent, remove organic solvent, and form liquid crystal orientation film or become the film of liquid crystal orientation film.
[step 2: alignment capability imparting processes]
In the case of the liquid crystal display cells manufacturing TN type, STN type, IPS type or FFS type, real
Execute the process that the film formed in described step 1 is given liquid crystal aligning ability.Thus, liquid crystal molecule
Alignment capability be imparted to film and become liquid crystal orientation film.Alignment capability imparting processes and such as can arrange
Lift: utilize the roller being wound with the cloth comprising the fibers such as nylon, artificial silk, cotton to film at certain orientation
On carry out the friction treatment of wiping, film is irradiated the light orientation process of the lonizing radiation of polarisation or non-polarized
Deng.On the other hand, in the case of manufacturing VA type liquid crystal display cells, can be by shape in described step 1
The film become uses directly as liquid crystal orientation film, it is possible to implement described film at alignment capability imparting
Reason.For the liquid crystal display cells of VA type, preferred liquid crystal orientation film can be preferably also used for PSA
The liquid crystal display cells of (Polymer sustained alignment) type.
[step 3: constructing of liquid crystal cells]
Prepare two pieces of substrates being formed with liquid crystal orientation film in this way, at two pieces of oppositely disposed bases
Configure liquid crystal between plate, thus manufacture liquid crystal cells.In order to manufacture liquid crystal cells, include, for example: (1)
By liquid crystal orientation film to in the way of across gap by oppositely disposed for two pieces of substrates, and use sealant will
The periphery laminating of two pieces of substrates, injects in the cell gap divided by substrate surface and sealant
After filling liquid crystal, the method that hand-hole is sealed；(2) it is being formed with the one of of liquid crystal orientation film
Commitment positions coating sealant on substrate, and then the set several positions on liquid crystal aligning face
After dropping liquid crystal, by liquid crystal orientation film to in the way of fit another block substrate, and by liquid crystal at base
The method (liquid crystal drip-injection (One Drop Fill, ODF) mode) etc. spread out on whole of plate.Right
Manufactured liquid crystal cells, it is generally desirable to and then be heated to used liquid crystal acquirement isotropic phase
Till temperature, then it is slowly cooled down to room temperature, thus removes flow orientation when liquid crystal is filled.
Sealant such as can use containing sclerosing agent and the ring of the alumina balls as sept (spacer)
Epoxy resins etc..Liquid crystal can enumerate nematic crystal and disc-like liquid crystal, wherein it is preferred that nematic crystal,
Such as can use: schiff bases (Schiff base) be liquid crystal, azoxy (azoxy) be liquid crystal, connection
Benzene series liquid crystal, Phenylcyclohexane system liquid crystal, ester system liquid crystal, terphenyl system liquid crystal, xenyl hexamethylene
It is liquid crystal, pyrimidine system liquid crystal, two methane series liquid crystal, double-octane system liquid crystal, cubane (cubane)
It it is liquid crystal etc..Additionally, it is possible in these liquid crystal, add such as cholesteryl liquid crystal (cholesteric liquid
Crystal), chiral agent, ferroelectric liquid crystals etc. and use.
In the case of manufacturing PSA type liquid crystal display cells, except injecting together with liquid crystal or dripping light
Beyond the aspect of polymerizable compound, by with described identical in the way of construct liquid crystal cells.Thereafter, exist
A pair substrate is had conduct electricity intermembranous applying direct current or exchange voltage state under to liquid crystal cells
Carry out light irradiation.It addition, using the aligning agent for liquid crystal shape on substrate comprising photopolymerizable compound
In the case of becoming film, it is also possible to construct liquid crystal cells with described identical mode, thereafter, Jing Guo
A pair substrate is had conduct electricity intermembranous applying direct current or exchange voltage state under to liquid crystal cells
Carry out the step of light irradiation to manufacture liquid crystal cell.
And, can be by obtaining the liquid crystal of the present invention at the outer surface of liquid crystal cells laminating Polarizer
Display element.The Polarizer of the outer surface fitting in liquid crystal cells can be enumerated: protects with cellulose acetate
Film clamping is referred to as the Polarizer of the light polarizing film of " H-film " or comprises itself Polarizer of H-film,
Described " H-film " is to make polyvinyl alcohol extend orientation while absorbing iodine and forming.
The liquid crystal cell of the present invention can be effectively applied to multiple device, such as, can be used for: clock and watch, just
Take type game machine, word processor, notes type personal computer, auto-navigation system, video camera,
Personal digital assistant (Personal DigitalAssistant, PDA), digital camera, mobile phone, intelligence hands
The various display devices of machine, various monitor, LCD TV etc. or light modulation film etc..It addition, use this
The aligning agent for liquid crystal of invention and the liquid crystal cell that formed also apply be applicable to phase retardation film.
[embodiment]
Hereinafter, according to embodiment, the present invention is specifically described further, but the present invention is not by this
A little embodiments limit.
The solution viscosity of each polymer solution in synthesis example, the acid imide rate of polyimides, weight
Mean molecule quantity and epoxide equivalent are to utilize following method to measure.
[solution viscosity (mPa s) of polymer solution] uses E type rotating cylinder viscometer, right at 25 DEG C
Use set solvent and be adjusted to the solution of polymer concentration 10 weight % and be measured.
The solution of polyimides is put into pure water by [the acid imide rate of polyimides], the most right
After the precipitation of gained is sufficiently carried out drying under reduced pressure, it is dissolved in deuterodimethylsulfoxide, with tetramethyl
Material on the basis of silane, at room temperature measures1H-nuclear magnetic resonance, NMR (1H-Nuclear Magnetic
Resonance,1H-NMR).According to gained1H-NMR spectrum, utilizes following numerical expression (1)
Obtain acid imide rate [%].
Acid imide rate [%]=(1-A1/A2×α)×100…(1)
(in numerical expression (1), A1For near chemical shift 10ppm occur by the proton of NH base
And the PeakArea come, A2For the PeakArea come by other protons, α be other protons relative to
The number ratio of one proton of the NH base in the precursor (polyamic acid) of polymer)
[weight average molecular weight Mw of polymer] is the gel permeation chromatography under conditions of below utilization
The polystyrene conversion value that method measures.
Tubing string: east Cao (Tosoh) (stock) manufactures, TSKgelGRCXLII
Solvent: oxolane
Temperature: 40 DEG C
Pressure: 68kgf/cm2
[epoxide equivalent] utilizes Japanese Industrial Standards (Japanese Industrial Standards, JIS) C 2105
Hydrochloric acid-methyl ethyl ketone method described in measures.
<synthesis of polymer>
[synthesis example 1: the synthesis of polyimides (PI-1)]
Using 2,3,5-tricarboxylic cyclopentyl acetic acid dianhydride (TCA) 22.4g (0.1 as tetracarboxylic dianhydride
Mole), as p-phenylenediamine (PDA) 8.6g (0.08 mole) and 3 of diamidogen, 5-diaminobenzene first
Acid cholesteric Arrcostab (HCDA) 10.5g (0.02 mole) is dissolved in METHYLPYRROLIDONE (NMP)
In 166g, at 60 DEG C, carry out reaction in 6 hours, it is thus achieved that the polyamic acid containing 20 weight % molten
Liquid.Divide the polyamic acid solution taking a small amount of gained, add NMP and make polyamic acid concentration 10 weight
Measuring the solution of %, solution viscosity obtained by mensuration is 90mPa s.
Then, in the polyamic acid solution of gained, add NMP and make polyamic acid concentration 7 weight
The solution of amount %, adds pyridine 11.9g and acetic anhydride 15.3g and carries out dehydration in 4 hours at 110 DEG C
Ring-closure reaction.After dehydration closed-loop reaction, utilize new NMP that intrasystem solvent is carried out solvent displacement
(this operation is utilized the pyridine used in dehydration closed-loop reaction and acetic anhydride to be removed outside system.With
Under identical), be derived from the polyimides (PI-1) of acid imide rate about 68% containing 26 weight %
Solution.Divide the polyimide solution taking a small amount of gained, add NMP and make polyimides concentration
The solution of 10 weight %, solution viscosity obtained by mensuration is 45mPa s.Then, reaction solution is noted
Enter to superfluous methanol, make product precipitate.Utilize methanol that described precipitate is carried out,
Under reduced pressure it is dried 15 hours with 40 DEG C, is derived from polyimides (PI-1).
[synthesis example 2: the synthesis of polyimides (PI-2)]
Using the TCA 22.5g (0.1 mole) as tetracarboxylic dianhydride, PDA 7.6g (0.07 as diamidogen
Mole), HCDA 5.2g (0.01 mole) and 4,4 '-diaminodiphenyl-methane (DDM) 4.0g
(0.02 mole) is dissolved in NMP 157g, carries out reaction in 6 hours, it is thus achieved that contain at 60 DEG C
The solution of the polyamic acid of 20 weight %.Point take the polyamic acid solution of a small amount of gained, add NMP and
Making the solution of polyamic acid concentration 10 weight %, solution viscosity obtained by mensuration is 110mPa s.
Then, in the polyamic acid solution of gained, add NMP and make polyamic acid concentration 7 weight
The solution of amount %, adds pyridine 16.6g and acetic anhydride 21.4g and carries out dehydration in 4 hours at 110 DEG C
Ring-closure reaction.After dehydration closed-loop reaction, utilize new NMP that intrasystem solvent is carried out solvent displacement,
It is derived from the solution of the polyimides (PI-2) of acid imide rate about 82% containing 26 weight %.
Divide the polyimide solution taking a small amount of gained, add NMP and make polyimides concentration 10 weight %
Solution, solution viscosity obtained by mensuration is 62mPa s.Then, reaction solution is injected into surplus
Methanol in, make product precipitate.Methanol is utilized described precipitate to be carried out, under reduced pressure
It is dried 15 hours with 40 DEG C, is derived from polyimides (PI-2).
[synthesis example 3: the synthesis of polyimides (PI-3)]
Using dicyclo [3.3.0] octane-2 as tetracarboxylic dianhydride, 4,6,8-tetrabasic carboxylic acid 2:4,6:8-dianhydride
(BODA) 24.9g (0.10 mole), PDA 8.6g (0.08 mole) and HCDA as diamidogen
10.4g (0.02 mole) is dissolved in NMP 176g, carries out reaction in 6 hours at 60 DEG C, it is thus achieved that
The solution of the polyamic acid containing 20 weight %.Divide the polyamic acid solution taking a small amount of gained, add NMP
And make the solution of polyamic acid concentration 10 weight %, solution viscosity obtained by mensuration is 103mPa s.
Then, in the polyamic acid solution of gained, add NMP and make polyamic acid concentration 7 weight
The solution of amount %, adds pyridine 11.9g and acetic anhydride 15.3g and carries out dehydration in 4 hours at 110 DEG C
Ring-closure reaction.After dehydration closed-loop reaction, utilize new NMP that intrasystem solvent is carried out solvent displacement,
It is derived from the solution of the polyimides (PI-3) of acid imide rate about 71% containing 26 weight %.
Divide the polyimide solution taking a small amount of gained, add NMP and make polyimides concentration 10 weight %
Solution, solution viscosity obtained by mensuration is 57mPa s.Then, reaction solution is injected into surplus
Methanol in, make product precipitate.Methanol is utilized described precipitate to be carried out, under reduced pressure
It is dried 15 hours with 40 DEG C, is derived from polyimides (PI-3).
[synthesis example 4: the synthesis of polyimides (PI-4)]
Using the TCA 110g (0.50 mole) and 1,3,3a as tetracarboxylic dianhydride, 4,5,9b-hexahydro-8-
Methyl-5-(tetrahydrochysene-2,5-dioxo-3-furyl) naphtho-[1,2-c] furan-1, (0.50 rubs 3-diketone 160g
You), as diamidogen PDA 91g (0.85 mole), 1, double (3-aminopropyl) tetramethyl two silica of 3-
(0.040 rubs cholestane 25g for alkane 25g (0.10 mole) and 3,6-double (4-amino benzoyl epoxide)
You) and aniline 14g (0.015 mole) as monoamine be dissolved in NMP 960g, at 60 DEG C
Under carry out 6 hours reaction, be derived from the solution containing polyamic acid.Divide the polyamides taking a small amount of gained
Amino acid solution, adds NMP and makes the solution of polyamic acid concentration 10 weight %, obtained by mensuration
Solution viscosity is 60mPa s.
Then, the polyamic acid solution of gained adds NMP 2,700g, and adds pyridine 390g
And acetic anhydride 410g and at 110 DEG C, carry out the reaction of 4 hours dehydration closed-loops.After dehydration closed-loop reaction,
Utilizing new gamma-butyrolacton that intrasystem solvent is carried out solvent displacement, be derived from about 2,500g contains
There is the solution of the polyimides (PI-4) of the acid imide rate about 95% of 15 weight %.Point take a small amount of
Described solution, adds NMP and makes the solution of polyimides concentration 10 weight %, obtained by mensuration
Solution viscosity is 70mPa s.Then, reaction solution is injected in the methanol of surplus, makes reaction produce
Thing precipitates.Utilize methanol that described precipitate is carried out, be under reduced pressure dried 15 hours with 40 DEG C,
It is derived from polyimides (PI-4).
[synthesis example 5: the synthesis of polyimides (PI-5)]
Using the TCA 22.4g (0.1 mole) as tetracarboxylic dianhydride, PDA 8.6g (0.08 as diamidogen
Mole), DDM 2.0g (0.01 mole) and 2,2 '-bis-(trifluoromethyl)-4,4 '-benzidine 3.2g
(0.01 mole) is dissolved in NMP 324g, carries out reaction in 4 hours, it is thus achieved that contain at 60 DEG C
The solution of the polyamic acid of 10 weight %.
Then, the polyamic acid solution of gained adds NMP 360g, and adds pyridine 39.5g
And acetic anhydride 30.6g and at 110 DEG C, carry out the reaction of 4 hours dehydration closed-loops.After dehydration closed-loop reaction,
Utilize new NMP that intrasystem solvent is carried out solvent displacement, it is thus achieved that the acyl containing 10 weight % is sub-
The solution of the polyimides (PI-5) of amination rate about 93%.Divide the polyamic acid solution taking a small amount of gained,
Solution viscosity obtained by mensuration is 30mPa s.Then, reaction solution is injected in the methanol of surplus,
Product is made to precipitate.Utilize methanol that described precipitate is carried out, be under reduced pressure dried with 40 DEG C
15 hours, it is derived from polyimides (PI-5).
[synthesis example 6: the synthesis of polyimides (PI-6)]
The diamidogen used is changed to 3,5-diaminobenzoic acid (3,5DAB) 0.08 mole and cholesteric
Alkyl oxy-2,4-diaminobenzene (HCODA) 0.02 mole, in addition, utilize and described synthesis
The method that example 1 is identical obtains polyamic acid solution.Divide the polyamic acid solution taking a small amount of gained, add
NMP and make the solution of polyamic acid concentration 10 weight %, solution viscosity obtained by mensuration is 80
mPa·s。
Then, the method identical with described synthesis example 1 is utilized to carry out imidizate, it is thus achieved that containing 26 weights
The solution of the polyimides (PI-6) of the acid imide rate about 65% of amount %.Divide the polyamides taking a small amount of gained
Imide liquor, adds NMP and makes the solution of polyimides concentration 10 weight %, obtained by mensuration
Solution viscosity is 40mPa s.Then, reaction solution is injected in the methanol of surplus, makes reaction produce
Thing precipitates.Utilize methanol that described precipitate is carried out, be under reduced pressure dried 15 hours with 40 DEG C,
It is derived from polyimides (PI-6).
[synthesis example 7: the synthesis of polyamic acid (PA-1)]
Using as tetracarboxylic dianhydride 1,2,3,4-Tetramethylene. tetracarboxylic dianhydride (CB) 200g (1.0 moles),
As the 2 of diamidogen, 2 '-dimethyl-4,4 '-benzidine 210g (1.0 moles) is dissolved in NMP 370g
And gamma-butyrolacton 3, in the mixed solvent of 300g, at 40 DEG C, carry out reaction in 3 hours, it is thus achieved that solid becomes
Divide concentration 10 weight %, the polyamic acid solution of solution viscosity 160mPa s.Then, by described poly-
Amic acid solution is injected in the methanol of surplus, and makes product precipitate.Utilize methanol to described heavy
Shallow lake thing is carried out, and is under reduced pressure dried 15 hours with 40 DEG C, is derived from polyamic acid (PA-1).
[synthesis example 8: the synthesis of polyamic acid (PA-2)]
The tetracarboxylic dianhydride used is set to pyromellitic acid anhydride (PMDA) 0.9 mole and CB 0.1
Mole, diamidogen is set to PDA 0.2 mole and 4，4′-diaminodipohenyl ether (DDE) 0.8 mole, except this
In addition, the method identical with described synthesis example 7 is utilized to obtain solid component concentration 10 weight %, solution
The polyamic acid solution of viscosity 170mPa s.Then, described polyamic acid solution is injected into surplus
In methanol, and product is made to precipitate.Methanol is utilized described precipitate to be carried out, under reduced pressure
It is dried 15 hours with 40 DEG C, is derived from polyamic acid (PA-2).
[synthesis example 9: the synthesis of polyamic acid (PA-3)]
Using the TCA7.0g (0.031 mole) as tetracarboxylic dianhydride, the following formula (R-1) as diamidogen
Represented compound 13g (being equivalent to 1 mole relative to 1 mole of TCA) is dissolved in NMP 80
In g, at 60 DEG C, carry out reaction in 4 hours, it is thus achieved that the polyamic acid (PA-3) containing 20 weight %
Solution.The solution viscosity of described polyamic acid solution is 2,000mPa s.Additionally, following formula (R-1)
Represented compound is based on the record of Japanese Patent Laid-Open 2011-100099 publication and synthesizes.Continue
And, described polyamic acid solution is injected in the methanol of surplus, and makes product precipitate.Utilize
Described precipitate is carried out by methanol, is under reduced pressure dried 15 hours with 40 DEG C, is derived from polyamides
Amino acid (PA-3).
[changing 6]
[synthesis example 10: the synthesis of polysiloxane (ASP-1)]
In the reaction vessel possessing blender, thermometer, addition funnel and reflux cooling pipe, put into
2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane (ECETS) 100.0g, methyl iso-butyl ketone (MIBK) 500
G and triethylamine 10.0g, at room temperature mixes.Then, addition funnel is utilized to spend 30 minutes
After dropping deionized water 100g, stirring under reflux, while carry out 6 hours instead at 80 DEG C
Should.After reaction terminates, organic layer is taken out, utilize 0.2 weight % aqueous ammonium nitrate solution to clean to cleaning
After water become neutrality till, the most under reduced pressure solvent and water are distilled and remove, thus with thickness
The form of transparency liquid obtains reactive polysiloxane (EPS-1).Described reactivity is gathered organic
Siloxanes (EPS-1) is carried out1H-NMR analyzes, and result is near chemical shift (δ)=3.2ppm
Obtain the peak value based on epoxy radicals of theoretical strength, thus confirm reaction does not produces the secondary anti-of epoxy radicals
Should.Weight average molecular weight Mw of the reactive polysiloxane of gained is 3,500, epoxide equivalent
For 180g/ mole.
Then, in the there-necked flask of 200mL, put into the reactive polysiloxane of 10.0g
(EPS-1), the methyl iso-butyl ketone (MIBK) 30.28g as solvent, the 4-12 as reactive compounds
Alkyl oxy benzoic acid 3.98g and UCAT 18X (trade name, general sieve in Sanya as catalyst
(San-Apro) (stock) manufactures) 0.10g, little is reacting at present with 100 DEG C of stirrings 48.Instead
After should terminating, the solution obtained adding ethyl acetate in the reactive mixture carries out three washings,
After using magnesium sulfate that organic layer is dried, solvent distillation is removed, is derived from the liquid crystal of 9.0g
Orientation polysiloxane (ASP-1).Weight average molecular weight Mw of the polymer of gained is
9,900。
[synthesis example 11: the synthesis of polysiloxane (PS1)]
In the reaction vessel possessing blender, thermometer, addition funnel and reflux cooling pipe, add
To styryl trimethoxy silane 31g, oxolane 70g, triethylamine 33g and deionized water
25g, at room temperature mixes.Then, stirring under reflux, while carry out 3 at 60 DEG C
Hour reaction.After reaction terminates, organic layer is taken out, add diethylene glycol diethyl ether 60g, carry out
Heating concentrates.It is concentrated into till solid component concentration becomes 30%, is derived from polysiloxane
(PS1) diethylene glycol diethyl ether solution.
[synthesis example 12, synthesis example 13]
Input raw material is set to as described in Table 1, in addition, utilizes identical with synthesis example 11
Synthetic method obtains polysiloxane (PS2) and the diethylene glycol two of polysiloxane (PS3)
Diethyl ether solution.Weight average molecular weight Mw of the polysiloxane of gained is shown in table 1 below in the lump
In.
[table 1]
Additionally, in table 1, the abbreviation of raw silicon hydride compounds is respectively following meanings.
STTMS: to styryl trimethoxy silane
ECETMS:2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane
PTMS: phenyltrimethoxysila,e
[embodiment 1]
<preparation of aligning agent for liquid crystal>
Use the polyimides (PI-1) as polymer, be added to the tripotassium phosphate as solvent
Ester (PTM), METHYLPYRROLIDONE (NMP) and butyl cellosolve (BC), make group of solvents
Become PTM: NMP: BC=20: 40: 40 (weight ratios), the solution of solid component concentration 6.5 weight %.
Described solution is filtered by the filter using aperture 1 μm, thus prepares aligning agent for liquid crystal (S-1).
Additionally, aligning agent for liquid crystal (S-1) is mainly used in the manufacture of the liquid crystal display cells of vertical orientating type.
<evaluation of the swelling characteristic of galley>
Described aligning agent for liquid crystal (S-1) is used to evaluate the swelling easness (swelling characteristic) of APR version.
APR version is the resin plate utilizing ultraviolet to irradiate subsclerotic aqueous photoresist and being formed, logical
Often use in the galley of liquid crystal orientation film printer.Contact with APR version making aligning agent for liquid crystal
In the case of APR version be difficult to swelling and refer to: when printing, aligning agent for liquid crystal is difficult to immerse to APR version
Printing is good.The evaluation of swelling characteristic is by APR version being impregnated in aligning agent for liquid crystal 1 day,
And the weight change measuring the APR version before and after dipping is carried out.Now, in the increasing of weight of APR version
Adding rate (swelling rate) less than in the case of 4%, APR version is difficult to swelling and is evaluated as good (zero),
In the case of increment rate is more than 4%, the easy swelling of APR version and be evaluated as bad (×).Its result,
In described embodiment, swelling rate is 3.5%, swelling characteristic " good (zero) ".Swelling rate is under use
State numerical expression (2) and calculate.
Swelling rate [%]=(W2-W1)/W1)×100…(2)
(in numerical expression (2), W1For the weight of the APR version before dipping, W2For the APR after dipping
The weight of version)
<evaluation of printing>
About the aligning agent for liquid crystal (S-1) of described middle preparation, to carrying out the printing to substrate continuously
In the case of printing (continuous printing) be evaluated.Evaluate and carry out as follows.First,
(Japan's description printer (stock) manufactures, En Gusiteluo (Angstrom) to use liquid crystal orientation film printer
Form " S40L-532 "), to be set to aligning agent for liquid crystal (S-1) the dripping quantity of anilox roll come and go 20
Drip the condition of (about 0.2g), be printed in glass substrate transparent of the transparency electrode that band comprises ito film
On electrode surface.About the printing to substrate, use new substrate with 1 minute interval, the most real
Execute 20 times.
Then, with 1 minute interval by aligning agent for liquid crystal (S-1) distribution (one way) in anilox roll,
When the time comes, carry out adding up to the operation (hereinafter referred to as dry run) making anilox roll contact of 10 times with galley
(the most not carrying out the printing to glass substrate).Additionally, described dry run is to exist wittingly
The operation implementing the printing of aligning agent for liquid crystal under harsh situation and carry out.
After the dry run of 10 times, glass substrate is then used formally to print.In formal printing,
After dry run, put into 5 pieces of substrates with 30 seconds intervals, at 80 DEG C, each substrate after printing is carried out
1 minute heating (prebake conditions) and by solvent remove, then carry out at 200 DEG C 10 minutes heating (after
Baking), form the film of thickness about 80nm.By utilizing the microscope of multiplying power 20 times to described painting
Film carries out observing and evaluating printing (continuous printing).About evaluation, by the 1st after dry run
Secondary formal printing not observed, the situation of the precipitation of polymer is set to continuous printing " good (zero) ",
The 1st formal printing after dry run will be observed the precipitation of polymer, but just implementing 5 times
Become not observe the situation of the precipitation of polymer during formula printing and be set to continuous printing " can (△) ",
It is set to print continuously by the situation still observing the precipitation of polymer after being repeated 5 formal printings
Brush " bad (×) ".Its result, continuous printing " good (zero) " in described embodiment.Additionally,
From experiment, in the aligning agent for liquid crystal that printing is good, polymer during putting into substrate continuously
Precipitation become good (disappearance).It addition, and then the number of times of dry run is changed to 15 times, 20 times, 25
Secondary, and respectively by with described identical in the way of evaluate the printing of aligning agent for liquid crystal as a result, described
In embodiment, when dry run is set to 15 times and 20 times for " good (zero) ", when 25 times being " can
(△)”。
[embodiment 2～embodiment 31 and comparative example 1～comparative example 5]
By the polymer used and the kind of solvent and composition respectively as described in table 2 below
As change, in addition, utilize the method identical with described embodiment 1 to prepare liquid crystal respectively and take
To agent (S-2)～aligning agent for liquid crystal (S-31) and aligning agent for liquid crystal (SR-1)～aligning agent for liquid crystal (SR-5).
It addition, about each aligning agent for liquid crystal, evaluate the swollen of galley in the way of identical with described embodiment 1
Profit characteristic and printing.The result these evaluated is shown in table 2 below.
[table 2]
In table 2, about using two kinds of polymer as component of polymer person (embodiment 18～embodiment
31), the use of each polymer phase total scale of construction 100 weight portion of polymer for being used is shown in the lump
Ratio (weight ratio).In each aligning agent for liquid crystal, (S-2)～(S-17), (SR-1)～(SR-5)
Being mainly used in the manufacture of the liquid crystal display cells of vertical orientating type, (S-18)～(S-23) is mainly used in
The manufacture of the liquid crystal display cells of TN type, (S-24) are mainly used in the system of the liquid crystal display cells of IPS
Make, and (S-29)～(S-31) is mainly used in utilizing the vertical alignment-type liquid crystal of optical alignment method to show unit
The manufacture of part, (S-25)～(S-28) is mainly used in the manufacture of the liquid crystal display cells of PSA mode.
In table 2, used in the preparation relative to aligning agent for liquid crystal of each compound of numeric representation of solvent composition
The allotment ratio (weight ratio) (the most identical about table 3 below～table 5) of total amount of solvent.Molten
The symbol of agent composition is respectively following meanings.
A: trimethyl phosphate
B: triethyl phosphate
C: hexamethyl phosphoric triamide
D:N-N-methyl-2-2-pyrrolidone N
E:N-ethyl-2-pyrrolidone
F: gamma-butyrolacton
G: gamma-valerolactone
H: δ-valerolactone
I:N, N-diethyl acetamide
J: butyl cellosolve
K: diethylene glycol diethyl ether
1: propylene glycol methyl ether acetate
[embodiment 32～embodiment 52]
By the polymer used and the kind of solvent and composition respectively as described in Table 3 below
As change, in addition, utilize the method identical with described embodiment 1 to prepare liquid crystal respectively and take
To agent (S-32)～aligning agent for liquid crystal (S-52).It addition, about each aligning agent for liquid crystal, with described
The mode that embodiment 1 is identical evaluates swelling characteristic and the printing of galley.The result that these are evaluated
It is shown in Table 3 below.
[table 3]
In table 3, about using two kinds of polymer as component of polymer person (embodiment 40～embodiment
43, embodiment 50～embodiment 52), illustrate that each polymer phase is for the polymer that used in the lump
The use ratio (weight ratio) of the total scale of construction 100 weight portion.It addition, in each aligning agent for liquid crystal, (S-32)～
(S-39), (S-44)～(S-49) be mainly used in the manufacture of liquid crystal display cells of vertical orientating type,
～(S-43), (S-50)～(S-52) is mainly used in the liquid crystal display cells of TN type (S-40)
Manufacture.In table 3, the symbol of solvent composition is respectively following meanings.D and j is identical with described table 2.
M:N, N-dimethylpropylene urea
N:4-formyl-morpholine
O:3-methyl-2-oxazolidone
P: tetrahydrochysene-4H-pyrans-4-ketone
R: tetramethylene sulfoxide
S:3-methyl cyclohexanone
T:4-methyl cyclohexanone
[embodiment 53～embodiment 56]
By the component of polymer used and the kind of solvent and composition respectively such as institute in table 4 below
Change as record, in addition, utilize the method identical with described embodiment 1 to prepare liquid respectively
Brilliant alignment agent (S-53)～aligning agent for liquid crystal (S-56).It addition, about each aligning agent for liquid crystal, with
The mode that described embodiment 1 is identical evaluates swelling characteristic and the printing of galley.These are evaluated
Result is shown in table 4 below.
[table 4]
In table 4, about using two kinds of polymer as component of polymer person (embodiment 55, embodiment
56), the use of each polymer phase total scale of construction 100 weight portion of polymer for being used is shown in the lump
Ratio (weight ratio).It addition, in each aligning agent for liquid crystal, (S-53), (S-54) are mainly used in vertically taking
To the manufacture of the liquid crystal display cells of type, (S-55), (S-56) are mainly used in the liquid crystal display of TN type
The manufacture of element.In table 4, the symbol of solvent composition is respectively following meanings.D and j and described table 2
Identical.
Q:5-methyl-2 furan carboxyaldehyde
U:N, N-dimethyl lactamide (compound represented by following formula (10-1))
[changing 7]
[embodiment 57～embodiment 60]
By the polymer used and the kind of solvent and composition respectively as described in table 5 below
As change, in addition, utilize the method identical with described embodiment 1 to prepare liquid crystal respectively and take
To agent (S-57)～aligning agent for liquid crystal (S-60).It addition, about each aligning agent for liquid crystal, with described
The mode that embodiment 1 is identical evaluates swelling characteristic and the printing of galley.The result that these are evaluated
It is shown in table 5 below.Additionally, in table 5, each polymer phase of numeric representation on component of polymer one hurdle
The use ratio (weight ratio) of total scale of construction 100 weight portion of polymer for being used.Solvent forms
Symbol (d, m, j) identical with described table 2 and table 3.
[table 5]
From described result, comprise aligning agent for liquid crystal (embodiment 1～the embodiment of described specific solvent
60) being all difficult to make galley swelling, continuous printing is the best.In contrast, without described specific
The swelling characteristic of the aligning agent for liquid crystal of the comparative example of solvent and continuous printing are the knot poorer than embodiment
Really.
Claims (6)
1. an aligning agent for liquid crystal, it contains:
Component of polymer, and
Choosing freely has the solvent of phosphorus atoms, a N, N-dimethylpropylene urea, tetrahydrochysene-4H-pyrans-4-ketone,
Chemical combination represented by tetramethylene sulfoxide, 3-methyl cyclohexanone, 4-methyl cyclohexanone, following formula (1)
Compound represented by thing, following formula (2), the compound represented by following formula (3) and following formula
(10) at least one specific solvent in the group that the compound represented by is formed,
In formula (1), R4For hydrogen atom or the alkyl of carbon number 1～6；In formula (2), R5For hydrogen atom
Or the alkyl of carbon number 1～6, R6Alkane diyl for carbon number 2～4；In formula (3), R7～R10Respectively
Independently be the organic group of hydrogen atom or monovalence；In formula (10), R11～R13It is separately that hydrogen is former
Son or the alkyl of carbon number 1～3.
Aligning agent for liquid crystal the most according to claim 1, wherein said there is phosphorus atoms solvent be
Select the compound represented by the compound represented by free following formula (p-1), following formula (p-2), under
State the compound represented by formula (p-3) and group that the compound represented by following formula (p-4) is formed
In at least one,
In formula (p-1)～formula (p-4), X1And Y1It is separately oxygen atom or sulphur atom；R1
For hydrogen atom or the alkyl of the monovalence of carbon number 1～10, R2For hydrogen atom or the organic group of monovalence；Wherein,
R1With R2Can mutually bond and form ring；R3It is separately hydrogen atom or the alkyl of carbon number 1～6,
It is binding on two R of nitrogen-atoms3Can mutually bond and form the nitrogen heterocyclic ring of monovalence together with nitrogen-atoms
Base；Wherein, R1And R2It is asynchronously hydrogen atom, R2And R3It it is asynchronously hydrogen atom；m、n、k
And j is separately the integer of 1～3；In the case of m, n, k, j are 2 or 3, in formula
Multiple R1、R3May be the same or different each other, in the case of m, n, k, j are 1, in formula
Multiple R2May be the same or different each other.
Aligning agent for liquid crystal the most according to claim 1 and 2, wherein said component of polymer contains
Select in the group that free polyamic acid, poly amic acid ester, polyimides and polysiloxane are formed
At least one polymer.
Aligning agent for liquid crystal the most according to claim 1 and 2, wherein relative in aligning agent for liquid crystal
Total scale of construction of solvent, the content ratio of described specific solvent is 1 weight %～80 weight %.
5. a liquid crystal orientation film, it uses liquid crystal according to any one of claim 1 to 4
Alignment agent and formed.
6. a liquid crystal cell, it possesses liquid crystal orientation film according to claim 5.
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| CN111448510A (en) * | 2018-01-25 | 2020-07-24 | Jsr株式会社 | Liquid crystal aligning agent, liquid crystal alignment film, liquid crystal element, and method for producing liquid crystal element |
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| JP7318787B2 (en) | 2023-08-01 |
| TW202014509A (en) | 2020-04-16 |
| JP2023014150A (en) | 2023-01-26 |
| JP6672815B2 (en) | 2020-03-25 |
| CN111849511A (en) | 2020-10-30 |
| TW202132548A (en) | 2021-09-01 |
| TWI801869B (en) | 2023-05-11 |
| TW201636382A (en) | 2016-10-16 |
| KR102454059B1 (en) | 2022-10-12 |
| CN106047373B (en) | 2020-10-09 |
| TW202330881A (en) | 2023-08-01 |
| JP2023143921A (en) | 2023-10-06 |
| JP2016200799A (en) | 2016-12-01 |
| JP2020095286A (en) | 2020-06-18 |
| TWI685514B (en) | 2020-02-21 |
| JP7188533B2 (en) | 2022-12-13 |
| CN116590027A (en) | 2023-08-15 |
| KR20160122636A (en) | 2016-10-24 |
| CN111849511B (en) | 2023-08-08 |
| JP2022017359A (en) | 2022-01-25 |
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