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EP0600064A1 - Polymeres pour optique non lineaire - Google Patents

Polymeres pour optique non lineaire

Info

Publication number
EP0600064A1
EP0600064A1 EP93912946A EP93912946A EP0600064A1 EP 0600064 A1 EP0600064 A1 EP 0600064A1 EP 93912946 A EP93912946 A EP 93912946A EP 93912946 A EP93912946 A EP 93912946A EP 0600064 A1 EP0600064 A1 EP 0600064A1
Authority
EP
European Patent Office
Prior art keywords
methyl
polymers
nlo
units
phenyl
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.)
Withdrawn
Application number
EP93912946A
Other languages
German (de)
English (en)
Inventor
Rolf-Peter Herr
Martin Schadt
Klaus Schmitt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of EP0600064A1 publication Critical patent/EP0600064A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • G02F1/3617—Organic materials containing polymers having the non-linear optical group in a side chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • C08F220/365—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate containing further carboxylic moieties

Definitions

  • the invention is concerned with polymers for the production of polymer layers having optical non-linear properties in selectively defined and optionally shaped areas, which areas are separate from those areas having a centro-symmetrical structure or areas having other optical non-linear properties.
  • organic and polymeric materials having large delocalized ⁇ -electron systems can have non-linear optical coefficients which are larger than in inorganic materials.
  • organic and polymeric materials can be varied readily and, accordingly, desirable secondary properties such as mechanical and chemical stability, optical absorption etc. can be adjusted without negatively influencing the non-linearity.
  • Thin films of organic or polymeric materials having a large non- linearity of the second order have a great application potential in the field of optical communication, laser technology, electrooptics etc.
  • nlo chromophores having several (2- 4) reactive substituents, which function as cross-linkers of an epoxide system (M. Eich, J. Appl. Phys. ££, 3241, 1989).
  • epoxides the cross-linking reaction takes place under the influence of an electric field and leads to a partial dipolar-orientated network which remains after disconnecting the field, since the dipolar arrangement is chemically fixed.
  • Structuring is only possible by introducing structured polarizing electrodes.
  • This is associated with a series of disadvantages.
  • the limits of the polarized region become diffuse by virtue of unavoidably occurring electrical stray fields on the periphery of the electrodes. This is not acceptable for many applications, e.g. strip wave guides, of periodic structures from polarized and non-polarized regions. More ⁇ over, for most applications the electrode layers must again be removed laboriously in further process steps.
  • the invention now provides stable nlo-active polymers, as well as materials for the manufacture of such polymers, which no longer have the aforementioned disadvantages or which only have these to a lesser extent.
  • the invention is concerned with nlo-active polymers of the general formula
  • M a , M , Mc signify monomer units for homo- or copolymers
  • x, y, z indicate mole fractions of the copolymers, whereby in each case 0 ⁇ x ⁇ l; 0 ⁇ y ⁇ l and 0 ⁇ z ⁇ 1
  • Sa, Sb, Sc represent spacer units
  • F denotes a nlo-active chromophore having an adsorption in the region of 300 nm to 700 nm
  • Z a , Zb represent molecule units which are photochemically dimerizable
  • n is a magnitude of 4-1000000
  • s is 1, 2 or 3
  • nlo-active chromophores (F) are bonded via a spacer (Sa) to the monomer unit (Ma) and themselves, again via a spacer, carry one or more photochemically dimerizable groups (Z a ) which serve for the photochemical cross-linkage of the polymer.
  • the bonding of the nlo-active chromophores on the one hand via the monomer unit to the polymer chain and on the other hand via the dimerizing unit into the network provides several advantages.
  • the concentration of the nlo-active chromophore can be varied in the polymer in a practically unlimited manner and the bonding of the chromophore at both ends of the molecule in the network provides for an effective restraint of the mobility, which guarantees long-term the stability of the nlo-active polymer layer.
  • the monomer units M a , Mb and M c for the formation of homo ⁇ polymers or copolymers have, in the scope of the present invention, the structures which are usual in polymer chemistry.
  • Such monomer units are, for example, acrylate, methacrylate, chloroacrylate, phenylacryl- ate, acryloxyphenyl, acrylamide, methacrylamide, chloroacrylamide, phenylacrylamide, vinyl ethers, styrene derivatives, vinyl esters, maleic acid derivatives, fumaric acid derivatives, siloxanes, epoxides and the like.
  • Acrylate, methacrylate, chloroacrylate, acrylamide, methacryl ⁇ amide, chloroacrylamide, styrene derivatives, siloxanes and the like are preferred monomer units.
  • copolymers there are to be understood not only statistical but also alternating copolymers. Statistical copolymers are preferably used. Homopolymers embrace linear and cyclic polymers such as, for example, cyclic polysiloxanes.
  • the spacer units S a and S bind the nlo-active chromophore (F) with the monomer unit (M a ), and, respectively, the dimerization unit (Zb) with the monomer unit (Mb).
  • the spacer S c links the nlo-active chromophore (F) with the dimerization unit (Z a ), whereby the nlo-active chromophore (F) can carry one or more dimerization units (Z a ) and correspondingly one or more spacers (Sc).
  • spacer units are known per se.
  • the term "spacer units" Sa, Sb and Sc signifies, for example, a n-alkylene chain with 1 to 10, preferably with 1 to 4, carbon atoms, a cyclo-alkylene group with 3 to 8 carbon atoms or phenylene, which can be substituted with -CN, -NO2 or halogen, or carbonate, an ester group, an ether group and the like, or a combination of such groups.
  • the spacer units Sa or S c can also be integrated into the nlo-active chromophore (F).
  • Examples of preferred spacer units are methylene, 1,2-ethylene, 1,3-propylene, 1,4-butylene, cyclo-butane-l,3-diyl, cyclo-pen- tane-l,2-diyl, cyclo-pentane-l,3-diyl, cyclo-hexane-l,3-diyl, cyclo-hexane- 1,4-diyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, ethyleneoxycar- bonyl, ethylenecarboxyl and the like.
  • spacer units which are integrated into the nlo-active chromophore (F) - i.e. form a part of the compound (F) - are e.g. piperidine, pyrrolidine or indole.
  • nlo-active chromophore denoted by (F) can be any compound which absorbs in the visible region of light and which is stable under the photo-chemical cross-linkage conditions, nlo-active chromophores (F) having an absorption in the region of 300 nm to 700 nm of general formula II are preferred in the scope of the present invention:
  • Ca denotes an electron acceptor Cd denotes an electron donor
  • Ar a , Arb denote phenylene, pyrimidine, pyridine, naphthyl, imidazole, oxazole, thiazole, benzoxazole or benzothiazole; 5 Arc denotes phenylene, pyrimidine, pyridine, naphthyl, 1-benzazine, 2-benzazine, 1,2-benzodiazine, 2,3-benzodiazine, 1,3-benzodiazine, 1,4-benzodiazine, 1,2,3,4-tetrahydro-l-benzazine, indole or dihydroindole; 0 m, r denote 1, 2 or 3 p, q denote 0 or 1.
  • the compounds of formula II are aniline derivatives of general formula II-A, diazo derivatives of general formula II-B or bis-diazo 15 derivatives of general formula II-C:
  • the compounds of formula II always contain at least one electron acceptor (Ca) and at least one electron donor (Cd), which in each case are separated from one another by the conjugated aromatic system.
  • Electron donors signify in the scope of the present invention dialkylamines, cyclic alkylamines, arylalkylamines, diarylamines, alkoxy groups or thioalkyl groups and the like.
  • Examples of preferred electron donor groups are dimethylamine, diethylamine, dipropyl-
  • the electron donor (Cd) can also be fused to the conjugated aromatic system; this is the case, for example, when Ar c signifies indole, dihydroindole or 1,2,3,4-tetrahydro-l-benzazine.
  • the compounds of formula II are in each case linked via a spacer Sa with the monomer unit (M a ) and via one or more spacers (Sc) with one or more dimerizable units (Z a ).
  • These spacers (S a or S c ) can be bonded either to one of the rings Ar a ,b or c or to a donor or to an acceptor group. However, they can also form part of the donor or the acceptor group.
  • Combined donor-spacer groups can be, for example, piperidine, pyrrolidine, alkoxy groups and the like. Examples of combined acceptor-spacer groups are alkylsulphonate, N-diphenyl- sulphonamide, N-dialkylsulphonamide and the like.
  • aniline derivatives of general formula II-A are examples of aniline derivatives of general formula II-A.
  • R2 signifies alkyl with 1 to 4 carbon atoms, aryl or a further Sc group
  • R ⁇ a represents dialkylamine, cycloamine, alkylaryl- amine or diarylamine
  • Sa, Sc signifies alkylene or -COOalkylene.
  • the spacer groups Sa and Sc can be optionally interchanged in formulae II-l to II-4, i.e. the nlo-active chromophore (F) can be bonded at the donor site or at the acceptor site with the monomer M a .
  • the spacer group (Sa or Sc) forms part of the donor group which is bonded directly to the monomer (M a ) or to the dimerization unit (Z a ).
  • the compounds of formula II-5 to 11-19 are examples of preferred diazo compounds of general formula II-B.
  • Rl, R2, Sa and Sc are as defined above;
  • R ⁇ represents alkoxy, thioalkyl, dialkylamine, cycloamine, alkylarylamine or diarylamine;
  • R ⁇ signifies hydrogen, halogen -N ⁇ 2, -CN or alkyl;
  • R5 and ⁇ represent hydrogen, halogen, -N ⁇ 2 or -CN; and
  • ------ signifies a single bond or a double bond.
  • Compounds of the general formulae are examples of preferred bis-diazo compounds of formula II-C:
  • the spacer groups (Sa and Sc) can be optionally interchanged and therefore the nlo-active chromophore (F) can be linked either at the donor site or at the acceptor site with the monomer (M a ).
  • the electron donors or the electron acceptors can be free functional groups or can be linked with one of the spacers Sa or Sc.
  • nlo-active chromophores (F) having free donor groups are compounds of the formulae II-4, II-8, 11-13, 11-16 to 11-19, II-23, ⁇ -26 and 11-29 to 11-32.
  • nlo-active chromophores having donor groups linked with one of the spacers are the aforementioned compounds of general formulae II-l, II-5, II-9 to 11-12, 11-15, 11-20, 11-24, 11-25 and 11-28.
  • nlo-active chromophores having fused cyclic donor groups on ring Ar c are compounds of the general formulae II-9, 11-10; 11-15, 11-24, 11-25 and 11-28.
  • nlo-active chromophores having free acceptor groups are compounds of general formulae II-l to 11-10 and 11-13 to 11-32.
  • Compounds of general formulae II-2, II-3, II-6, II-7, 11-14, 11-21, 11-22 and 11-27 are examples of compounds in which the spacer forms part of the donor group.
  • the dimerization units Z a and Zb are molecule units which can undergo a photochemical [2 + 2] cycloaddition, which leads to the cross- linkage of the polymer and accordingly to its stabilization.
  • the dimerizable units are, however, not, or only to a very small extent, incorporated into the chain under the polymerization conditions.
  • Such dimerizable units are in the scope of the present invention, for example, compounds of general formulae III and IV:
  • ring A signifies benzene, pyridine, pyrimidine or furan
  • R7,R8,R9 signifies H, alkyl, alkoxy, dialkylamine, cyclo- alkylamine, alkoxycarbonyl, alkyl-COO, carboxyl, -CN, halogen, -N ⁇ 2, whereby R 7 and R 8 or R 8 and R 9 together can also signify -O(CH2)lO-; 1 signifies 1 or 2; RlO signifies hydroxy, alkoxy, aryl, aryloxy, aryloxy- alkyl, aryloxycarbonyl, phenyl-COO-alkoxy; 0 signifies 1 or 2, whereby the bonding to the spacer units Sb and, respectively, S c can be effected via the residues R 7 , R 8 , R 9 , R 10 .
  • alkyl signifies a straight-chain or branched alkyl group with 1 to 10 carbon atoms, preferably a straight-chain alkyl group with 1 to 4 carbon atoms, such as, for example, methyl, ethyl, propyl or butyl.
  • alkoxy and alkoxycarbonyl denote an ether and, respectively, an ester in which the alkyl residue is as defined above. Such residues are methoxy, ethoxy, propyloxy, butyl- oxy, methoxycarbonyl, ethoxycarbonyl, propyloxycarbonyl or butyloxycarbonyl.
  • aryl denotes phenyl or naphthyl which is unsubstituted or substituted with halogen, -N ⁇ 2, -CN, alkyl or alkoxy.
  • Cinnamic acid and chalcone derivatives of general formula III as well as coumarin derivatives of formula IV are particularly suitable for the photochemical cross-linkage of the polymer.
  • Such preferred dimerization units are, for example:
  • R 7 , R 8 , R 9 and RlO are as defined above; and H signifies -OH, alkoxy or halogen.
  • the polymers of formula I are distinguished by the fact that they are accessible in a simple manner.
  • the monomers are constructed from the individual components, i.e. from the dimerizable unit of formula III or IV, the spacers (S a , Sb and, respectively, S c ), the nlo- active chromophores II and the polymerizable units (M a or Mb).
  • the formation of the polymers is then effected in a manner known per se.
  • the polymerization can be effected, for example, in the melt or in solution with the exclusion of oxygen in the presence of a radical initiator which can generate radicals thermally, photochemically or by a redox-reaction.
  • the reaction can be effected in a temperature range of -10°C to 120°C, preferably in a range of 20°C to 100°C.
  • a solution of the polymer material obtained can be prepared, which is centrifuged in a spin-coating apparatus on to a carrier coated with an electrode so that homogeneous layers of 0.5-5 ⁇ m thickness result, nlo-active chromophores can subsequently be adjusted dipolarly e.g. using a so-called Corona-Poling apparatus under a high electric field strength.
  • the region to be cross-linked can be exposed to e.g. a mercury-high pressure lamp, a xenon lamp or a pulsed UV-laser. The exposure duration depends on the capacity of the individual lamps and can vary from a few minutes to several hours.
  • the cross-linkage can, however, also be effected by irradiating the homogeneous layer using filters which e.g. let through only the radiation which is suitable for the cross-linkage reaction.
  • Preferred monomers are:
  • the mixture was stirred at room temperature for 3.5 hours, filtered, concentrated and diluted with 200 ml of dichloromethane.
  • the solution was washed with 100 ml of 5% acetic acid and subsequently 3 times with 100 ml of water each time, dried over sodium sulphate, filtered and concentrated.
  • the resulting precipi ⁇ tate was filtered off, washed with 60 ml of an ice-cold 5% aqueous hexa- fluorophosphoric acid solution and subsequently with 120 ml of ice-cold diethyl ether. After drying in a vacuum at room temperature there were obtained 11.9 g of 5-diazonium-hexafluorophosphato-2-nitrobenzoic acid as yellowish-white crystals.
  • reaction vessel was opened and the solution was diluted with 10 ml of tetrahydrofuran while stirring. Subsequently, the diluted solution was added dropwise to 800 ml of diethyl ether while stirring at room temperature. The separated polymer was filtered off, dried, dissolved in 40 ml of dichloro- methane and this solution was added dropwise to 800 ml of diethyl ether. This procedure was repeated twice.
  • N,N'-dicyclohexylurea was filtered off, the filtrate was diluted with a further 100 ml of dichloromethane, washed with 50 ml of 5% acetic acid and subsequently three times with 100 ml of water each time. After drying the solution over sod um sulphate and evaporation of the solvent the residue was recrystallized from a mixture of 80 ml of ethanol and 2 ml of tetrahydrofuran.
  • reaction vessel was opened and the solution was diluted with 15 ml of tetrahydrofuran while stirring. Subsequently, the diluted solution was added dropwise to 800 ml of diethyl ether while stirring at room temperature. The separated polymer was filtered off, dried, dissolved in 50 ml of dichloromethane and this solution was added dropwise to 800 ml of diethyl ether. This procedure was repeated twice.
  • copolymers can be manufactured analogously: D) Poly[l-[2-[methyl-4-[(E)-3-[2-[4-[(E)-2-methoxycarbonyl-vinyl]- phenoxy]-ethoxy-carbonyl]-4-nitro-phenylazo]-phenyl-amino]-ethoxy- carbonyl]-l-methyl-ethylene-co-l-[2-[4-[(E)-2-methoxycarbonyl-vinyl]- phenoxy]-ethoxycarbonyl]-l-methyl-ethylene] (1:9)
  • the 4-N-methyl-aminobenzoic acid (2-methyl-acryloyloxy)-ethyl ester used as the starting material was prepared as follows:

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  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Polymères pour optique non linéaire répondant à la formule générale (I) et servant à produire des couches polymères présentant des propriétés optiques non linéaires dans des zones définies de manière sélective et éventuellement mises en forme, ces zones étant distinctes des zones à structure centro-symétrique ou des zones présentant des propriétés optiques non linéaires différentes. Dans la formule (I), Ma, Mb et Mc représentent des motifs monomères pour des homopolymères ou copolymères; x, y et z représentent des fractions molaires des copolymères: dans chaque cas 0 < x 1, 0 y < 1 et 0 z < 1; Sa, Sb et Sc représentent des motifs d'écartement; F représente un chromophore à activité optique non linéaire présentant une adsorption comprise entre 300 et 700 nm; Za et Zb représentent des motifs moléculaires dimérisables par voie photochimique; n est une grandeur comprise entre 4 et 1000000; et s est 1, 2 ou 3. Lesdits polymères sont caractérisés en ce que les chromophores (F) à activité optique non linéaire sont liés au motif monomère (Ma) par l'intermédiaire d'un motif d'écartement (Sa), et portent eux-mêmes, également par l'intermédiaire d'un motif d'écartement, un ou plusieurs groupes (Za) dimérisables par voie photochimique et destinés à la réticulation photochimique du polymère.
EP93912946A 1992-06-19 1993-06-11 Polymeres pour optique non lineaire Withdrawn EP0600064A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH1946/92 1992-06-19
CH194692 1992-06-19
PCT/EP1993/001476 WO1994000797A1 (fr) 1992-06-19 1993-06-11 Polymeres pour optique non lineaire

Publications (1)

Publication Number Publication Date
EP0600064A1 true EP0600064A1 (fr) 1994-06-08

Family

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Family Applications (1)

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EP93912946A Withdrawn EP0600064A1 (fr) 1992-06-19 1993-06-11 Polymeres pour optique non lineaire

Country Status (3)

Country Link
EP (1) EP0600064A1 (fr)
JP (1) JPH06509889A (fr)
WO (1) WO1994000797A1 (fr)

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* Cited by examiner, † Cited by third party
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WO2012019704A1 (fr) * 2010-08-07 2012-02-16 Merck Patent Gmbh Particules pour écrans d'affichage électrophorétiques
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WO2019003682A1 (fr) * 2017-06-30 2019-01-03 富士フイルム株式会社 Copolymère photo-alignable, fil photo-aligné, stratifié optique et dispositif d'affichage d'image
WO2019225632A1 (fr) * 2018-05-25 2019-11-28 富士フイルム株式会社 Copolymère photo-alignable, film de photo-alignement et stratifié optique
CN113544554B (zh) * 2019-03-07 2023-06-20 富士胶片株式会社 偏振元件及图像显示装置
JP7299647B2 (ja) * 2020-02-07 2023-06-28 国立研究開発法人物質・材料研究機構 高分子化合物、高分子化合物の製造方法、接着剤組成物、硬化物、接着剤組成物の製造方法および接着力の調整方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3926872A1 (de) * 1989-08-16 1991-02-21 Merck Patent Gmbh Photovernetzte polymere fuer die nichtlineare optik
FR2659340A1 (en) * 1990-03-06 1991-09-13 Thomson Csf Photocrosslinkable polymer usable in nonlinear optics
EP0477665B1 (fr) * 1990-09-24 1994-11-23 Siemens Aktiengesellschaft Résines époxy réticulées à propriétés optiques non linéaires
FR2668158B1 (fr) * 1990-10-22 1994-05-06 Thomson Csf Polymere reticulable pour applications en optique non lineaire.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9400797A1 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9939555B2 (en) 2011-05-31 2018-04-10 Dic Corporation Cinnamic acid derivative, polymer thereof, and liquid crystal alignment layer comprising cured product thereof
JPWO2020175620A1 (fr) * 2019-02-28 2020-09-03

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WO1994000797A1 (fr) 1994-01-06

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