CN107422542A - A kind of method for the liquid crystal polymer brush regulation and control liquid crystal aligning constructed by random copolymerization - Google Patents
A kind of method for the liquid crystal polymer brush regulation and control liquid crystal aligning constructed by random copolymerization Download PDFInfo
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- CN107422542A CN107422542A CN201710372657.4A CN201710372657A CN107422542A CN 107422542 A CN107422542 A CN 107422542A CN 201710372657 A CN201710372657 A CN 201710372657A CN 107422542 A CN107422542 A CN 107422542A
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- liquid crystal
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- 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
Abstract
The invention discloses a kind of method for the liquid crystal polymer brush regulation and control liquid crystal aligning constructed by random copolymerization.First by liquid crystal monomer with it is a kind of containing can the monomer copolymerization of post-crosslinking reaction group obtain random copolymerization liquid crystal polymer, the liquid crystal random copolymer is spin-coated on to the substrate surface of reactive group modification using sol evenning machine, in copolymer can post-crosslinking reaction group be bonded with the reactive group in substrate, after annealing, that is, obtain vertical orientated liquid crystal copolymer film.The gained substrate of liquid crystal copolymer film will finally be scribbled liquid crystal cell is made with the cover glass of vertical orientated modification, you can the regulation and control to liquid crystal aligning are realized in liquid crystal cell.Compared to traditional block polymer brush by covalent bond realization and substrate suction-operated, the more smooth stabilization in interface that the liquid crystal copolymer brush contacts with liquid crystal, and possess more selectivity；The synthesis of liquid crystal monomer and polymer is more easy in the present invention, can be applied to the preparation of industrialized nano material.
Description
Technical field
The invention discloses a kind of method for the liquid crystal polymer brush regulation and control liquid crystal aligning constructed by random copolymerization, belong to
Field of material technology.
Background technology
The control of material surface performance is most important in many researchs and commercial technology field, for example, in biotechnology and
Advanced microelectronics science and technology aspect, and be a kind of feasible method of regulation surface property using polymer brush.Pass through polymer
The obtained patterning organic film of brush is in the control of cell growth, the preparation of biomimetic material, micro- reaction vessel and drug delivery
Have wide practical use Deng field.Polymer commonly used to prepare polymer brush has：Block copolymer and graft copolymer
Mainly include physical absorption, " grafting from " and " the methods of grafting to " Deng, its preparation method.Liquid crystal molecule
Be ordered among practical application the vital effect that serves, and the orientation of liquid crystal molecule have with substrate surface property it is close
The relation cut, its degree of orientation are heavily dependent on the surface action of substrate.In order to realize the regularly arranged of liquid crystal molecule,
Its interaction between liquid crystal molecule interface can be controlled by selecting suitable polymer brush.And it is based on rod shaped liquid crystal primitive
Polymer, it is possible to make liquid crystal molecule insert stand between the liquid crystal unit being vertically arranged, so as to realize the vertical of liquid crystal molecule
Arrangement.
The present invention attempt to it is a kind of containing can post-crosslinking reaction group liquid crystal random copolymer, to realize to liquid crystal molecule
The control of orientation.Due in copolymer can post-crosslinking reaction group can be with substrate reactive group (such as hydroxyl, amino) key
Close, liquid crystal random copolymer is firmly anchored in substrate, by change can post-crosslinking reaction group content, can regulate and control
Spacing between rod shaped liquid crystal primitive, so as to influence the oriented of liquid crystal molecule.For special liquid crystal unit (such as azo
Benzene), the orientation of liquid crystal molecule can be further regulated and controled by illumination.
The content of the invention
Regulate and control liquid crystal molecule it is an object of the invention to design and prepare a kind of liquid crystal random copolymer brush, and by it
Orientation.
The technical scheme is that：
A kind of method for the liquid crystal polymer brush regulation and control liquid crystal aligning constructed by random copolymerization, comprises the following steps：
(1) preparation of liquid crystal random copolymer, the liquid crystal random copolymer be by the primitive containing rod shaped liquid crystal monomer and
Containing can post-crosslinking reaction group monomer according to feed intake mass ratio 99: 1-5: 1 occur random copolymerization reaction be made；
(2) the liquid crystal random copolymer is dissolved in organic solvent, recycles sol evenning machine to be spin-coated on reactive group and repair
The substrate surface of decorations, in the liquid crystal random copolymer can post-crosslinking reaction group be bonded with substrate reactive group, it is described
Reactive group is hydroxyl or amino；
(3) substrate for scribbling liquid crystal random copolymer is made annealing treatment, that is, obtains vertical orientated liquid crystal and be total to
Homopolymer film, so as to form polymer brush；
(4) liquid crystal cell finally is made in the substrate with polymer brush and the cover glass of the vertical orientated modification in surface, utilized
The suction effect of capillary sucks liquid crystal between the liquid crystal cell space, and the liquid crystal molecule inserts the liquid crystal base for standing in and being vertically arranged
Between member, so as to realize vertical arrangement of the liquid crystal molecule in its mesomorphic range, that is, the regulation and control to liquid crystal aligning are realized.
Further, the structure of liquid crystal random copolymer described in step (1) is shown in formula I：
In Formulas I, x, y are integer,
A, B are one or both of Formula II：
D, E is one kind in alkyl, alkoxy, ester group, carbonyl；
M is one kind that can be in post-crosslinking reaction group in formula III：
R1、R2、R3、R4For one kind in hydrogen, alkyl, alkoxy；
One kind shown in expression IV in liquid crystal unit；
Further, liquid crystal random copolymer is dissolved in organic solvent with 0.05%-1% mass fraction described in step (2)
In.
Further, the organic solvent described in step (2) is can be organic molten compared with liquid crystal random copolymer described in good dissolving
Agent, such as chlorine benzene,toluene,xylene high boiling organic solvent.
Further, the annealing temperature of step (3) is more than random copolymer clearing point；
Further, the rate of temperature fall of the annealing of step (3) is 0.5-5 DEG C/min.
Further, when rod shaped liquid crystal primitive is azobenzene in liquid crystal copolymer described in step (1), its manufactured liquid is used
During brilliant box regulation and control liquid crystal aligning, the orientation of liquid crystal can be changed by the irradiation of light sources with different wavelengths, realize the tune to liquid crystal aligning
Control.
The beneficial effects of the present invention are：
(1) present invention quotes a kind of random copolymer brush containing liquid crystal unit to control the orientation of liquid crystal molecule, and this is random
Copolymer has excellent dissolubility and film forming；And realized and substrate suction-operated by covalent bond compared to traditional
Block polymer brush, the more smooth stabilization in interface that the liquid crystal copolymer brush contacts with liquid crystal, and possess more selectivity；
(2) by regulate and control the primitive containing rod shaped liquid crystal monomer and containing can post-crosslinking reaction group monomer the mass ratio that feeds intake
The preparation of Object LC random copolymer can be achieved, so as to obtain that there is the polymer brush of suitable rod shaped liquid crystal primitive spacing,
Liquid crystal monomer and polymer are readily synthesized, and can be applied to the preparation of industrialized nano material, for the control of surface property from now on
Development provides a simple and direct approach.
Brief description of the drawings
Fig. 1 is the nuclear-magnetism figure that monomeric charge mass ratio is the liquid crystal copolymer obtained by 20: 1 in embodiment 1；
Fig. 2 is the polarisation of 4 '-n-pentyl-[1,1 '-biphenyl] -4- nitriles (5CB) orientation in liquid crystal cell 1,2 in embodiment 1
Scheme (upper right corner is conoscopic figure)；
Fig. 3 is that 4 '-n-pentyl-[1,1 '-biphenyl] -4- nitriles (5CB) are interior through ultraviolet source in liquid crystal cell 1 in embodiment 1
Polarisation figure after the irradiation of (365nm) and visible light source (475nm) (upper right corner is conoscopic figure).
Embodiment
The present invention is described in further details with reference to specific embodiment, but the present invention is not limited thereto.
Embodiment 1
It is a kind of to be adjusted by the liquid crystal random copolymer (using cyclic acid anhydride as post-crosslinking reaction group) containing Azobenzene mesogen
The method for controlling liquid crystal molecule 4 '-n-pentyl-[1,1 '-biphenyl] -4- nitriles (5CB) orientation, comprises the following steps：
(1) preparation of the random copolymer containing Azobenzene mesogen：
Raw material：Maleic anhydride, pentamethyl-diethylenetriamine, cuprous bromide, alpha-brominated ethyl isobutyrate, petroleum ether, tetrahydrochysene
Furans (THF), chlorobenzene, aluminum oxide (Al2O3)。
Monomer 1 containing Azobenzene mesogen：6- [4 '-(4- phenoxy groups) is to butyl azobenzene] Hexyl 2-propenoate
(MAzo)
Monomer 2 containing naphthenic acid anhydride group：Maleic anhydride (MAH)
Catalyst：Cuprous bromide (CuBr)
Initiator：Alpha-brominated ethyl isobutyrate
Part：Pentamethyl-diethylenetriamine (PMDETA)
The alpha-brominated ethyl isobutyrate of initiator (3.700mg, 0.019mmol), monomer 1 are sequentially added in dry test tube
(0.200g, 0.490mmol) and monomer 2 (0.010g, 0.102mmol), catalyst CuBr (2.730mg, 0.019mmol), match somebody with somebody
Body PMDETA (3.280mg, 0.019mmol), the solution that chlorobenzene is made into 35% is then added ,-vacuumizing-is freezed and leads to nitrogen
Tube sealing after circulation three times, polymerization pipe is placed in 80 DEG C of constant temperature oil baths equipped with thermostat, after reacting a period of time, takes out glass
Glass pipe, is put into ice-water bath and cools down, and stops polymerization.Tube sealing is opened, polymer solution is passed through equipped with active Al2O3Pillar, so
Afterwards with substantial amounts of petroleum ether precipitation polymer, filter, wash, vacuum drying.
Obtain the random copolymer of structure shown as a formula V：
WhereinRepresent
Be respectively 20: 1,10: 1,5: 1,4: 1 comonomer 1 by adding mass ratio and monomer 2 prepared it is a series of
The random copolymer of different MAH contents.Fig. 1 is the core for the liquid crystal copolymer that synthesized monomeric charge mass ratio is 20: 1 gained
Magnetic chart.
(2) the random copolymer brush induction 5CB arrangements containing Azobenzene mesogen：
Random copolymer containing Azobenzene mesogen is dissolved in chlorobenzene with 0.1% mass fraction, is spun in substrate.
Then copolymer is made to be connected to substrate surface gained film progress vacuum heat.Then rinsed with dichloromethane on silicon chip not
The polymer connected, nitrogen drying silicon chip, anneals under the clearing point temperature of polymer, produces the polymer brush after orientation.
Liquid crystal cell is made with the cover glass of the vertical orientated modification in surface in the polymer brush substrate of gained after annealing, Fig. 2 is
5CB is in liquid crystal cell 1 (the monomeric charge mass ratio of random copolymer is 20: 1), (the monomeric charge matter of random copolymer of liquid crystal cell 2
Amount is than being 4: the polarisation figure (upper right corner is conoscopic figure) of orientation in 1), figure it is seen that 5CB does not have in liquid crystal cell 1 under polarisation
Birefringent phenomenon is occurred, and orthogonal black cross is showed in the case where boring light；Meanwhile appearance is double under polarisation in liquid crystal cell 2 by 5CB
Refraction effect, and in the case where boring light without orthogonal black cross.Illustrate that 5CB is arranged vertically in liquid crystal cell 1, and it is non-in liquid crystal cell 2
Vertical arrangement.It follows that if the content of Azobenzene mesogen is too low in copolymer, the polymer brush liquid crystal unit formed
Between distance it is excessive, it is impossible to induce 5CB to be arranged vertically.
(3) photoresponse behaviors of the 5CB on copolymer brush containing Azobenzene mesogen
Liquid crystal cell 1 is placed under 365nm ultraviolet source after irradiating 5s, liquid crystal cell birefringence occurs under polarisation and showed
As, and its black cross orthogonal in the case where boring light disappears, Fig. 3 (right side) is that 5CB ultraviolet sources in liquid crystal crystalline substance box 1 shine in embodiment 1
The polarisation figure (upper right corner is conoscopic figure) penetrated after 5s, from figure 3, it can be seen that 5CB vertical arrangement is destroyed.Continue to put in sample
In wavelength under the irradiation of 475nm light sources, the birefringent phenomenon of sample disappears, and has reappeared orthogonal black cross, can see
Go out, 5CB returns to the state of vertical arrangement.Said process illustrates the adjustable draining of copolymer brush containing Azobenzene mesogen
The orientation of brilliant small molecule.
Embodiment 2
A kind of liquid crystal random copolymer (using isocyanates as post-crosslinking reaction group) by the primitive containing biphenyl liquid crystal is adjusted
The method for controlling liquid crystal molecule 4 '-n-pentyl-[1,1 '-biphenyl] -4- nitriles (5CB) orientation, comprises the following steps：
(1) preparation of the random copolymer of the primitive containing biphenyl liquid crystal：
Raw material：Methylacryoyloxyethyl isocyanates (MOI), pentamethyl-diethylenetriamine, cuprous bromide are alpha-brominated different
Ethyl butyrate, petroleum ether, tetrahydrofuran (THF), chlorobenzene, aluminum oxide (Al2O3)。
Monomer 1 containing biphenyl liquid crystal primitive：6- [4 '-(4- phenoxy groups) is to butyl biphenyl] hexyl methacrylate
Monomer 2 containing isocyanate groups：Methylacryoyloxyethyl isocyanates (MOI)
Catalyst：Cuprous bromide (CuBr)
Initiator：Alpha-brominated ethyl isobutyrate
Part：Pentamethyl-diethylenetriamine (PMDETA)
The alpha-brominated ethyl isobutyrate of initiator (3.700mg, 0.019mmol), monomer 1 are sequentially added in dry test tube
(0.200g, 0.508mmol) and monomer 2 (0.010g, 0.065mmol), catalyst CuBr (2.730mg, 0.019mmol), match somebody with somebody
Body PMDETA (3.280mg, 0.019mmol), the solution that chlorobenzene is made into 35% is then added ,-vacuumizing-is freezed and leads to nitrogen
Tube sealing after circulation three times, polymerization pipe is placed in 80 DEG C of constant temperature oil baths equipped with thermostat, after reacting a period of time, takes out glass
Glass pipe, is put into ice-water bath and cools down, and stops polymerization.Tube sealing is opened, polymer solution is passed through equipped with active Al2O3Pillar, so
Afterwards with substantial amounts of petroleum ether precipitation polymer, filter, wash, vacuum drying.
Obtain random copolymer of the structure as shown in Formula IV.
WhereinRepresent
Be respectively 20: 1,10: 1,5: 1,4: 1 comonomer 1 by adding mass ratio and monomer 2 prepared it is a series of
The random copolymer of different MOI contents.
(2) the random copolymer brush induction 5CB arrangements of the primitive containing biphenyl liquid crystal：
The random copolymer of the primitive containing biphenyl liquid crystal is dissolved in chlorobenzene with 0.1% mass fraction, is spun in substrate.So
Copolymer is set to be connected to substrate surface gained film progress vacuum heat afterwards.Then rinsed on silicon chip with dichloromethane and do not connect
On polymer, nitrogen drying silicon chip, annealed under the clearing point temperature of polymer, produce orientation after polymer brush.
Liquid crystal cell 1,2 is made (respectively in the polymer brush substrate of gained after annealing and the cover glass of the vertical orientated modification in surface
The monomeric charge mass ratio of random copolymer is with embodiment 1 in liquid crystal cell), using the suction effect of capillary in liquid crystal cell space
Between suck nematic liquid crystal small molecule 5CB (4 '-n-pentyl-[1,1 '-biphenyl] -4- nitriles), existed by polarized light microscope observing 5CB
Orientation under polymer brush induction.
There is not birefringent phenomenon in liquid crystal cell 1 in 5CB under polarisation, and orthogonal black cross is showed in the case where boring light；
Meanwhile there is birefringent phenomenon in liquid crystal cell 2 in 5CB under polarisation, and in the case where boring light without orthogonal black cross.Illustrate 5CB in liquid
It is arranged vertically in brilliant box 1, and the non-perpendicular arrangement in liquid crystal cell 2.If it follows that in copolymer biphenyl liquid crystal primitive content
Too low, then the distance between the polymer brush liquid crystal unit formed is excessive, it is impossible to induces 5CB to be arranged vertically.
Claims (9)
1. a kind of method for the liquid crystal polymer brush regulation and control liquid crystal aligning constructed by random copolymerization, comprises the following steps：
(1) preparation of liquid crystal random copolymer, the liquid crystal random copolymer are by the monomer of the primitive containing rod shaped liquid crystal and containing can
The monomer of post-crosslinking reaction group occurs random copolymerization reaction according to the mass ratio 99: 1-5: 1 that feeds intake and is made；
(2) the liquid crystal random copolymer is dissolved in organic solvent, recycles sol evenning machine to be spin-coated on reactive group modification
Substrate surface, in the liquid crystal random copolymer can post-crosslinking reaction group be bonded with substrate reactive group, the reaction
Property group is hydroxyl or amino；
(3) substrate for scribbling liquid crystal random copolymer is made annealing treatment, that is, obtains vertical orientated liquid crystal copolymer
Film, so as to form polymer brush；
(4) liquid crystal cell finally is made in the substrate with polymer brush and the cover glass of the vertical orientated modification in surface, utilizes capillary
The suction effect of pipe sucks liquid crystal between the liquid crystal cell space, the liquid crystal molecule insert stand in the liquid crystal unit that is vertically arranged it
Between, so as to realize vertical arrangement of the liquid crystal molecule in its mesomorphic range, that is, realize the regulation and control to liquid crystal aligning.
2. it is as claimed in claim 1 it is a kind of regulate and control liquid crystal aligning method, it is characterised in that in the step (1) liquid crystal without
Advise the structure of copolymer shown in formula I：
In Formulas I, x, y are integer,
A, B is one or both of Formula II：
D, E is one kind in alkyl, alkoxy, ester group, carbonyl；
M is one kind that can be in post-crosslinking reaction group in formula III：
R1、R2、R3、R4For one kind in hydrogen, alkyl, alkoxy；
One kind shown in expression IV in liquid crystal unit；
A kind of 3. method of regulation and control liquid crystal aligning as claimed in claim 1 or 2, it is characterised in that liquid crystal in the step (2)
Random copolymer is dissolved in organic solvent with 0.05%-1% mass fraction.
4. it is as claimed in claim 3 it is a kind of regulate and control liquid crystal aligning method, it is characterised in that in the step (2) liquid crystal without
Rule copolymer is dissolved in organic solvent with 0.1% mass fraction.
5. the method for a kind of regulation and control liquid crystal aligning as claimed in claim 1 or 2, it is characterised in that organic in the step (2)
Solvent is one kind in chlorine benzene,toluene,xylene.
A kind of 6. method of regulation and control liquid crystal aligning as claimed in claim 1 or 2, it is characterised in that the annealing of the step (3)
Temperature is more than random copolymer clearing point；Rate of temperature fall is 0.5-5 DEG C/min.
7. the method for a kind of regulation and control liquid crystal aligning as claimed in claim 1 or 2, it is characterised in that contain rod in the step (1)
The monomer of shape liquid crystal unit and containing can post-crosslinking reaction group monomer according to the mass ratio that feeds intake for 20: 1.
A kind of 8. method of regulation and control liquid crystal aligning as claimed in claim 1 or 2, it is characterised in that liquid crystal in the step (1)
Polymeric ligands contain Azobenzene mesogen.
9. the method for a kind of regulation and control liquid crystal aligning as claimed in claim 8, it is characterised in that use liquid crystal cell regulation and control liquid
During crystalline substance orientation, under the irradiation of light sources with different wavelengths, the orientation of liquid crystal can change.
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| CN108485682A (en) * | 2018-04-28 | 2018-09-04 | 湘潭大学 | A method of passing through special rodlike molecule or its polymers modulate liquid crystal molecular orientation |
| CN109575335A (en) * | 2018-11-12 | 2019-04-05 | 湘潭大学 | A method of regulation nanostructure orientation |
| CN110568689A (en) * | 2019-09-05 | 2019-12-13 | 浙江大学 | Method for regulating orientation of liquid crystal element in colloidal liquid crystal |
| CN111690123A (en) * | 2020-05-09 | 2020-09-22 | 北京大学 | Long wedge-shaped side chain liquid crystal polymer and sub-ten nano structure light-induced orientation method |
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| CN104380187A (en) * | 2012-04-16 | 2015-02-25 | 拉谢扎·科米托夫 | Polymer for use in alignment layer |
| CN104672410A (en) * | 2013-09-06 | 2015-06-03 | 得克萨斯A&M大学系统 | Self-assembled structures, method of manufacture thereof and articles comprising the same |
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| CN101948562A (en) * | 2010-10-12 | 2011-01-19 | 复旦大学 | Photoresponse block liquid crystal polymer with crosslinkable property and preparation method thereof |
| CN104380187A (en) * | 2012-04-16 | 2015-02-25 | 拉谢扎·科米托夫 | Polymer for use in alignment layer |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108485682A (en) * | 2018-04-28 | 2018-09-04 | 湘潭大学 | A method of passing through special rodlike molecule or its polymers modulate liquid crystal molecular orientation |
| CN108485682B (en) * | 2018-04-28 | 2021-11-09 | 湘潭大学 | Method for regulating orientation of liquid crystal molecules through special rod-shaped molecules or polymers thereof |
| CN109575335A (en) * | 2018-11-12 | 2019-04-05 | 湘潭大学 | A method of regulation nanostructure orientation |
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| CN110568689A (en) * | 2019-09-05 | 2019-12-13 | 浙江大学 | Method for regulating orientation of liquid crystal element in colloidal liquid crystal |
| CN111690123A (en) * | 2020-05-09 | 2020-09-22 | 北京大学 | Long wedge-shaped side chain liquid crystal polymer and sub-ten nano structure light-induced orientation method |
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