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WO1996024648A1 - Polymere de type cristal liquide - Google Patents

Polymere de type cristal liquide Download PDF

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Publication number
WO1996024648A1
WO1996024648A1 PCT/SE1996/000152 SE9600152W WO9624648A1 WO 1996024648 A1 WO1996024648 A1 WO 1996024648A1 SE 9600152 W SE9600152 W SE 9600152W WO 9624648 A1 WO9624648 A1 WO 9624648A1
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WIPO (PCT)
Prior art keywords
monomers
electron
cross
polar
linking
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English (en)
Inventor
Sven Torbjörn LAGERWALL
Bo Anders Hult
Carl Fredrik Sahlen
Olof Mikael TROLLSÅS
David Hermann
Lachezar Komitov
Per Rudquist
Bengt Stebler
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Priority to EP96903288A priority Critical patent/EP0830440A1/fr
Priority to JP8524205A priority patent/JPH10513278A/ja
Publication of WO1996024648A1 publication Critical patent/WO1996024648A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—Polymers
    • 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
    • G02F1/35—Non-linear optics
    • G02F1/355—Non-linear optics characterised by the materials used
    • G02F1/361—Organic materials
    • G02F1/3615—Organic materials containing polymers

Definitions

  • the present invention relates to a material in the form of a polymer having a chiral tilted smectic structure which can be used, for example, for optical components on printed-circuit boards.
  • NLO non-linear optical
  • the electronics industry demands components which operate in the wavelength range of 600-1550 nm so that they are suitable for fibre optics.
  • the components should withstand temperatures from -40 to 200°C, and they should be stable for at least 10 years. According to the American military standard, the components should withstand continuous use at 125°C.
  • WO 92/20058 describes surface-stabilized ferro- electric liquid crystals which are used to obtain a monomer whose polymerization in sufficiently thin layers (approximately 2 ⁇ m) between electrode-coated glass plates can be reversed in an electri field. These monomers suffer from the disadvantage that they depend on the glass plates, with their surface conditioning, and on the electric field, for maintenance of the polar alignment.
  • the object of the present invention is to supply a novel type of polymer material which permanently exhibits non-linear optical activity, and to supply a process for producing this material.
  • This material is to be mechanically and thermally stable over wide temperature ranges and easy to machine and handle.
  • an organic polymer having a fixed polar structure which is characterized in that it consists of a densely cross-linked polymerization product of monomers, for which monomers it holds that a) at least a part of the starting monomers exhibit a tilted smectic phase, b) at least a part of the starting monomers have one or more chiral centres, c) at least a part of the starting monomers are provided with one or more electron-donating and/or electron- accepting groups so that an electric dipole moment or a non-n ⁇ rror-symmetrical polarizability exists transversely to the longitudinal direction of the monomers, and d) the monomers are provided with polymerizable groups which are intended for cross-linking and which are in the form of acrylate, methacrylate, styrene or other polymerizable groups which are intended for cross-linking, with these polymerizable groups intended for cross-linking being present in the monomers
  • a preferred embodiment of the invention is an organic polymer having a fixed polar alignment which is characterized in that the monomers exhibit a structure selected from among the following: A) compounds of the formula I,
  • Another embodiment of the invention is an organic polymer having a fixed polar structure which is characterized in that it includes a monomer which is in tilted smectic phase and which has, at both ends, polymerizable groups intended for cross- linking, together with a monomer which has a polymerizable group at one end, and which has one or more chiral centres, with at least one of the monomers being provided with one or more electron-donating and/or electron-accepting groups.
  • Still another embodiment of the invention is an organic polymer having a fixed polar structure which is characterized in that only one type of monomer which fulfils points a)-d) is included in the polymer.
  • the invention also relates to a process for producing an organic polymer having a fixed polar structure, wherein the monomers in the tilted smectic phase are aligned in a polar order by an external electrical field, and subsequently cross-linked at the selected polymerizable groups by photopolymerization to fix the polar alignment permanently.
  • the invention also relates to the use of the polymer material in optical components.
  • a smectic liquid-crystalline phase is understood to mean a liquid-crystalline phase having a layered structure.
  • the longitudinal axis of the molecules which are aligned in parallel forms an angle with the normal of the layer, the so-called tilt angle. This angle should be as large as possible in order to achieve the best non-linear optical properties of the material.
  • a pyroelectric material is understood to mean a material which has a macroscopic polar order, which material consequently exhibits a permanent macroscopic polarization different from zero in its thermodynamic equilibrium state. The electric polarization of the material is a function of temperature.
  • a ferroelectric material is understood to mean a material which has a macroscopic polar order and whose polarization can be reversed using an external electric field, when the external electric field reverses direction.
  • Antiferroelectric materials thus form a subclass of ferroelectric materials.
  • Antiferroelectric and ferroelectric liquid crystals can both be made to change the molecular orientation and thus the direction of polarisation according to the direction of an applied external electrical field, while for pyroelectric liquid crystals the orientation is fixed.
  • Both pyroelectric, ferroelectric and antiferroelectric liquid crystals belong to the family of tilted smectic liquid crystals, which among themselves display several different variants.
  • ferroelectric, antiferroelectric and pyroelectric materials see also R ⁇ mpp Chemie Lexikon, ninth edition, pages 1331 and 3702, respectively. This literature citation is hereby incorporated by reference.
  • Molecular hyperpolarizability is understood to mean a molecular parameter which appears in a material composed of molecules having non-linear optical properties. See also WO 92/20058.
  • a strong hyperpolarizability implies a capacity for strong polari- zation, which can be achieved by the monomers being provided with electron-donating and/or electron-accepting groups.
  • An electron-donating or, respectively, an electron-accepting group is a group which has the capacity to donate electron density or, respectively, positive charge density to, preferably, an aromatic ring.
  • Dense cross-linking is understood to mean a high degree of cross-linking.
  • the expression "at least a part of for describing the monomers is understood to mean a sufficient quantity for achieving the property which is sought by means of adding that particular monomer.
  • the expression is also understood to mean a part of one and the same monomer. All the sought-after proper-ties can be present in a single monomer.
  • That the polymer material according to the invention is macroscopically polar means that the material as a whole has a polar axis, i.e. that either a polarization is present which is different from zero or the polarizability is different in two opposite directions, i.e. that the polarizability does not exhibit mirror symmetry. This implies that the material is helix-free and that the polarization is uniform with regard to direction and size. Furthermore, the polarization is permanent and does not alter time.
  • That the polymer material according to the invention is processable means that it can be machined and shaped for manufacturing components.
  • Optical components are, according to the invention, understood to mean, in particular, components which are intended to be used on printed-circuit boards, in optical communication, for telecommunication, for optoelectronics, for controlling the refractive index using an electric field, for producing frequency doubling, for controlling and guiding optical waves, for regulating the colour of light, for acting as a circuit breaker, and the like.
  • Fig. 1 shows the reactions for synthesizing a bifunctional monomer according to Example 1 below
  • Fig. 2 shows the reactions for synthesizing a monofunctional chiral monomer having an electron-accepting group according to Example 3
  • Fig. 3 shows a phase diagram for different mixtures of the monomers ⁇ according to Example 1 and K) according to Example 3, in which i denotes isotropic phase, sA*, sC* and sE*, respectively, denote chiral smectic A phase, C phase and E phase, respectively, and c denotes crystalline phase,
  • Fig. 4 shows how LI/I depends on the angle of rotation a and the external electrical field which is applied to the polymer material.
  • the polymer material according to the invention places a number of specific demands on the monomer system employed, i.e. the mixture of monomers.
  • the system must be chiral and have a tilted smectic phase (in order to make the system ferroelectric) so that it can be aligned in a polar manner, be cross-linkable so that a stabilized material can be formed, and at the same time be designed for non-linear optics, i.e. be hyperpolarizable. While all these properties are desirable, they are difficult to achieve in one monomer. For this reason, the system is designed as a mixture of two or more monomers, with a copolymer being obtained on polymerization. However, it is theoretically possible to meet all the demands using one and the same monomer.
  • the resulting mixture then acquires a chiral tilted smectic phase.
  • three of the properties can be introduced into one monomer, and four or five other monomers can then be added in order to obtain a strong fourth property. It is also possible to conceive of up to 20 or 30 monomers in the mixture. For example, a chiral tilted smectic phase may be desired which exists over a wider temperature range. If each individual monomer has a chiral tilted smectic phase which exists over a fairly narrow temperature range, a mixture which has a phase over a wider range can be obtained if many different monomers are mixed together.
  • the temperature interval over which the tilted smectic phase exists should be at least approximately 10°C. See Figure 3.
  • liquid-crystalline phases having titled molecules with respect to the layers can be used in place of smectic C, i.e. smectic F, smectic I, smectic G, smectic H, smectic J, smectic K, or combinations of these phases, and with the C phase.
  • smectic C i.e. smectic F, smectic I, smectic G, smectic H, smectic J, smectic K, or combinations of these phases, and with the C phase.
  • These phases differ from each other as a result of the molecular packing within the smectic layers differing.
  • the smectic C phase is that which is most used due to the fact that it has the lowest viscosity and is the easiest to predict before carrying out the synthesis.
  • the monomer syntheses for the purpose of the invention are unique. However, it is possible to conceive of a large number of molecular elements which can be combined so as to meet the four demands which are placed on the monomers: that they exhibit a tilted smectic phase, are chiral, are polar and are cross-linkable, with the different elements being responsible for one or more properties. Consequently, the choice of monomer is not crucial as long as the four demands are met. All known and conceivable monomers and monomeric elements can be used.
  • the monomers can be provided with electron-donating and/or electron-accepting groups.
  • the aim is to have as strong dipole as possible, for example -N0 2 in combination with -NH 2 .
  • electron-donating groups are -CN, -N0 2 , -S0 2 R, -CH(CN) 2 and -CHO and examples of electron- donating groups which can be used are -OH, -SH, -NH 2 , -NR 2 , -OR or -SR, with R representing an alkyl, aryl, alkylaryl or arylalkyl group or a fluorinated variant of any one of these.
  • Monomers which have a polymerizable group intended for cross-linking in the form of an acrylate, meth-acrylate, styrene or other suitable polymerizable group intended for cross-linking, at one end or at both ends of the monomers are here termed mono-functional and bifunctional monomers, respectively.
  • the monofunctional monomers will have a free end while bifunctional monomers are polymerized at both ends and therefor act as cross-linkers.
  • the crosslinks may also connect the molecules in such a way that the hyperpolarizable groups will be extended over several monomers transversely or longitudinally.
  • the aim of the monomer synthesis was first to produce bifunctional liquid- crystalline compounds exhibiting the sc phase.
  • the intention of the bifimctionality of the monomers is to provide the possibility of cross-linking of the material and thermally stabilize the structure.
  • the aim was to produce chiral liquid- crystalline monomers which behave in a ferroelectric manner when they are mixed with the first-mentioned type of monomer.
  • Example 1 Two examples of monomer syntheses in accordance with the invention are given in Examples 1 and 3 below.
  • Example 1 two cross-linkable compounds were prepared which exhibited a smectic C phase and which differed from each other in that one possessed acrylate groups and the other methacrylate groups as polymerizable groups:
  • Example 3 two chiral monomers were prepared which were provided with a dipole group. They differed from each other in that the polymerizable group was an acrylate group in the one case and a methacrylate group in the other:
  • the compounds were chemically characterized by means of 1H NMR on a 250 MHz Bruker, and, if necessary, by means of FTIR on a Perkin-Elmer 1760X. The purity was measured by means of HPLC, Varian.
  • Potassium hydroxide (4.90 g, 74.31 mmol) was then added in order to effect alkaline hydrolysis of the ester.
  • the potassium salt which formed precipitated and was filtered from the solution.
  • the salt was dissolved in a mixture of 30 ml of acetic acid and 30 ml of ethanol and the whole was stirred at 120°C for one hour.
  • the final product a white crystalline powder, pre-cipitated when the solution was cooled, and was filtered off.
  • the reaction was monitored by FTIR, with the carbonyl peak of the salt at 1628 cm “1 shifting to 1669 cm "1 for the acid. Yield: 6.00 g (66%) of 3.
  • the organic phase was separated off an washed three times with water, dried using magnesium sulphate and evaporated.
  • the product was purified by column chromatography (silica gel, hexane/EtOAc as eluent).
  • the final product 6 was in the form of white crystals.
  • Example 1 Compounds in Example 1 were subjected to thermal cha-racterization on a Perl ⁇ n-Elmer DSC-7 using a heating cooling speed of 10°C/min.
  • DSC denotes differen- tial scanning calo-rimetry.
  • Hot-stage microscopy using polarized light (Leitz Ortholux POL BKII equipped with a Mettlel FP82 Hot Stage and an FP80 central processor) was employed for the thermal and mor-phological characterizations. Patterns from small-angl X-ray scattering (SAXS) of the different liquid-crystalline phases were registered with a Statton camera, which was equipped with a resistive oven, using Cu KI radiation from a Philips PW 1830 generator.
  • SAXS small-angl X-ray scattering
  • the Sc phases in Table 1 are in a thermodynamically stable state since they occur both during heating and cooling.
  • Example 3 A further two monomers according to the invention were prepared in steps
  • a polymer according to the invention was prepared from the monomers from Examples 1 and 3 in the following manner.
  • Cells were produced from two glass plates having electrodes of indium tin oxide (ITO) coated with a 1000 A layer of SiO.
  • ITO indium tin oxide
  • the inner side of the glass plates was covered with a aligning layer of spun-on and longitudinally brushed polyimide, which orientes the liquid-crystal molecules along the glass surface.
  • the cell having a distance of 2 ⁇ m between the plates and the d mensions of approximately 1x2 cm, was supplied with the monomer mixture by means of capillary filling at a temperature corresponding t smectic A* phase. Isotropic phase can also be used.
  • the aligning layer ensured that a book-shelf structure in smectic A* phase was automatically obtained, which structure w then retained after transition to smectic C* phase.
  • the degree of orientation can be monitored in a pola-rization microscope since total extinction is obtained when the optic axis is parallel or perpendicular to the polarizer. It is also possible to orient the sample by means of shearing in smectic A* phase prior to illumination with UV light.
  • the electric field was maintained and, once good orientation of the monomer mixture had been achieved, the cell was illuminated with UV light from an OSRAM Ultra- Vitalux lamp, for instance during 20 minutes with a 300 W lamp, as a result of which the polar alignment was fixed permanently by means of photo-induced poly-merization of the structure. Consequently, the alignment remains after the voltage has been switched off and it is not possible, either, to reverse the orientation in the material by reversing the field. It is also not possible, after the polymerization, to see any phase transitions when the temperature is raised or lo-wered (20-150°C). Thus, the uniform book-shelf structure was locked in place by the polymerization.
  • the photopolymerization allows the mesophase of the monomer prior to polymerization to be selected appropriately, since the temperature can be chosen at will. Another great ad-vantage is that tailor-made components can be produced using a light mask which screens off the UV light during photo-lithography of the monomer mixture such that the polymerized area assumes a certain desired form. Other polymerization pro ⁇ cedures can also be used provided that the polymerization can be carried out at a temperature at which an appropriate mesophase exists.
  • the layer can also be made to be thicker than 2 ⁇ m, for example 5 ⁇ m, which is an important advance in relation to previously known materials.
  • Polymer networks of the S A *, S c * and S E * types were formed by both polyp 0) and poly( ⁇ ), depending on the poly-merization temperature.
  • the structures of the liquid-crystal-line-like polymer networks of poly(l ⁇ ) were confirmed by X-ray investigations.
  • the thermal stability of the alignment wasomme-gated by infrared dichroism in accordance with the procedure of F. Sahlen et al., Polymer, in press 1996.
  • the dichroic ratio was calculated and the normalized dichroic ratio was plotted against the temperature. It was observed that the alignment de-creased somewhat with increasing temperature but was restored again completely on cooling.
  • the final thermal stability of the polymer network was approximately 360°C; the polymer decomposes above this tempe-rature.
  • the electronics industry requires that, for soldering onto printed-circuit boards, the material which is employed should withstand at least 250°C; previously known non-linear optical materials do not meet this criterion.
  • the polymeric film which is formed is a thermoset plastic which is one single network exhibiting dense cross-linking.
  • Components can potentially be mass- produced from the po-lymer which has been prepared. They can be manufactured both as machinable thin films and as bulk material.
  • An alternative to machining is to use a light mask to screen off the UV light du-ring photolithography of the monomer mixture so that the poly-merized area assumes a certain desired form.
  • the Pockels effect was measured in order to determine the non-linear optical properties of the material.
  • the Pockels effect, or the linear electrooptical effect signifies that the refractive index is altered by the influence of an applied external electri- cal field.
  • the procedure using crossed polari-zers was used. The method and the apparatus are described in the article by C.P.J.M. van der Vorst and C. J.M. van Weerdenburg, Nonlinear Optical Properties of Organic Materials III, 1990, SPIE Vol. 1337, 246-257.
  • the apparatus principally consisted of the following components.
  • a 10 mW, 632.8 nm HeNe laser (Melles Griot) was used to generate a laser beam which was passed through a polarizing prism which was rotated 45° to the left, seen from the laser.
  • the polarized laser beam was passed through the sample at an angle ⁇ , the so-called angle of rotation, with 90° corresponding to the laser beam impinging perpendicularly to the surface of the sample.
  • the sample was located between the same glass plates which were used during the polymerization in Example 4.
  • the beam was then passed through a Soleil-Babinet compensator (wavelength range 250-3500 nm, phase retardation 0-2S ⁇ l% at 546 nm and 0-lS ⁇ 0.5% at 1000 nm) and after that through a polarizing prism which was rotated 45° to the right, seen from the laser.
  • the polarizing prisms had an extinction of ⁇ 10 "5 (Melles Griot).
  • the intensity I of the beam was measured with a detector having a Si photo-diode (Melles Griot). In front of the detector, a filter was located which transmitted 632.8 nm, FWHM 3 ⁇ 0.6 nm (Melles Griot).
  • Figure 4 shows a graph in which ⁇ l/I is plotted against the angle of rotation ⁇ for different strengths of the electric field which is applied over the material.
  • ⁇ l/I is given as a normalized value, i.e. the highest value is set at 1 and remaining values are calculated relative to this value. At its highest, the absolute value of the signal was approximately 10 "5 . It is evident from the graph that ⁇ l/I is proportional to the strength of the electric field and that ⁇ l/I varies with the angle of rotation. This is explained by the external electric field modulating the refractive index of the material, as a result of which the intensity I is modulated due to the non-linear optical properties of the material.
  • Figure 4 consequently demonstrates that a non-linear response can be obtained in accordance with the invention.
  • the material has been stable as regards the measured values shown in Figure 4 for more than two months, i.e. up until today.
  • the measured results showed that the material from Example 4 exhibited non-linear optical activity.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Liquid Crystal Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un polymère organique dont la structure polaire fixe présente la caractéristique d'être constituée d'un produit de polymérisation de monomères densément réticulé. Concernant ces monomères, a) une partie au moins de ces monomères présente une phase smectique inclinée, b) une partie au moins de ces monomères comporte un ou plusieurs centres chiraux, c) une partie au moins de ces monomères est pourvue d'un ou plusieurs groupes donneurs d'électrons et/ou d'un ou plusieurs groupes accepteurs d'électrons de façon qu'un axe polaire existe transversalement à l'axe longitudinal des monomères, et d) les monomères comportent des groupes polymérisables, destinés à la réticulation et appartenant au groupe des acrylates, méthacrylates, styrènes et autres groupes polymérisables permettant la réticulation. L'invention concerne également un procédé de production du matériau polymère et l'utilisation de celui-ci dans des composants optiques.
PCT/SE1996/000152 1995-02-08 1996-02-08 Polymere de type cristal liquide Ceased WO1996024648A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP96903288A EP0830440A1 (fr) 1995-02-08 1996-02-08 Polymere de type cristal liquide
JP8524205A JPH10513278A (ja) 1995-02-08 1996-02-08 液晶重合体材料

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9500458A SE505409C2 (sv) 1995-02-08 1995-02-08 Polär organisk polymer med tiltad vätskekristallin struktur, förfarande för framstälning därav samt användning därav
SE9500458-6 1995-02-08

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WO1996024648A1 true WO1996024648A1 (fr) 1996-08-15

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JP6133977B2 (ja) * 2012-06-12 2017-05-24 エルジー・ケム・リミテッド 重合性液晶化合物、これを含む液晶組成物及び光学異方体
JP7743216B2 (ja) * 2021-07-01 2025-09-24 住友化学株式会社 エーテル化合物の製造方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0501563A1 (fr) * 1991-02-26 1992-09-02 Koninklijke Philips Electronics N.V. Dispositif pour doubler la fréquence d'une onde lumineuse
WO1992020058A2 (fr) * 1991-04-24 1992-11-12 University Research Corporation Cristaux liquides ferroelectriques pour applications en optique non lineaire

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0501563A1 (fr) * 1991-02-26 1992-09-02 Koninklijke Philips Electronics N.V. Dispositif pour doubler la fréquence d'une onde lumineuse
WO1992020058A2 (fr) * 1991-04-24 1992-11-12 University Research Corporation Cristaux liquides ferroelectriques pour applications en optique non lineaire

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
STN INTERNATIONAL, File CAPLUS, CAPLUS Accession No. 1993:148136, KOZLOVSKY M.V. et al., "Chiral Smectic Side-Chain Copolymers and Their Properties"; & CRYST. RES. TECHNOL., (1992), 27(8), 1141-5. *
STN INTERNATIONAL, File CAPLUS, CAPLUS Accession No. 1994:324302, ANDERSSON H. et al., "Synthesis and Photopolymerization of Bifunctional Liquid Crystalline Vinyl Ether Monomers"; & MOL. CRYST. LIQ. CRYST. SCI. TECHNOL., Sect. A (1994), 243, 313-21. *

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SE505409C2 (sv) 1997-08-25
JPH10513278A (ja) 1998-12-15
SE9500458L (sv) 1996-08-09
SE9500458D0 (sv) 1995-02-08
EP0830440A1 (fr) 1998-03-25

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