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WO1996003674A1 - Element de guide d'ondes optique pouvant etre blanchi - Google Patents

Element de guide d'ondes optique pouvant etre blanchi Download PDF

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Publication number
WO1996003674A1
WO1996003674A1 PCT/EP1995/002880 EP9502880W WO9603674A1 WO 1996003674 A1 WO1996003674 A1 WO 1996003674A1 EP 9502880 W EP9502880 W EP 9502880W WO 9603674 A1 WO9603674 A1 WO 9603674A1
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WO
WIPO (PCT)
Prior art keywords
guiding layer
formula
optical waveguide
group
polymeric
Prior art date
Application number
PCT/EP1995/002880
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English (en)
Inventor
Marcus Charles Johannes Marie Donckers
Bernhardus Henricus Maria Hams
Ulfert Elle Wiersum
Tjerk Oedse Boonstra
Original Assignee
Akzo Nobel N.V.
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 Akzo Nobel N.V. filed Critical Akzo Nobel N.V.
Publication of WO1996003674A1 publication Critical patent/WO1996003674A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/675—Low-molecular-weight compounds
    • C08G18/677—Low-molecular-weight compounds containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups
    • C08G18/678—Low-molecular-weight compounds containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/045—Aromatic polycarbonates containing aliphatic unsaturation
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/045—Light guides
    • G02B1/046—Light guides characterised by the core material
    • 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

Definitions

  • the invention is in the field of optical waveguides.
  • Such waveguides generally are built up such that light can propagate within the confinement of a waveguiding material surrounded by a material having a lower refractive index than the waveguiding material.
  • the invention is directed to optical waveguide components having a layered structure comprising a polymeric guiding layer sandwiched between two deflection layers of lower refractive index than the guiding layer, wherein the guiding layer polymer comprises moieties susceptible to a change of refractive index when subjected to appropriate irradiation.
  • the wave confinement in vertical direction i.e., perpendicular to the layers
  • waveguide channels can be laterally defined by selectively changing the refractive index of the guiding layer polymer.
  • the refractive index change in most cases amounts to a decrease, and the irradiation process is referred to as a bleaching process.
  • the moieties susceptible to the refractive index change thus render the guiding layer polymer photobleachable, and the waveguide channels can be created by irradiating the material surrounding the desired confinement region.
  • the invention especially is also directed to bleachable optical waveguide components that can be made electro- optically active, i.e. non-linear optical (NLO) polymers.
  • NLO non-linear optical
  • Bleachable optical waveguide components of the type referred to above have been disclosed in US 5,142,605 (and corresponding EP 358 476), which disclosure is hereby incorporated by reference into this description for all purposes. While suitable results can be achieved with the components disclosed herein, and these components can be made electro-optically active, other materials are being sought, and improvements are still desired. It is an object of the present invention to provide new and useful bleachable optical waveguide components.
  • the invention seeks to provide such components as are capable of more efficient definition of lateral wave confinements (channels) than prior art components, i.e., that require a lower bleaching dose and/or in which suitable waveguide channels can be defined through a faster process.
  • the invention also seeks to provide bleachable components that can be rendered electro-optically active at the same time, and which yield better e/o characteristics than prior art components of the type in which waveguide channels are defined by bleaching.
  • the invention consists therein that, in an optical waveguide component as described above, the moieties that are susceptible to a change of refractive index when subjected to appropriate irradiation include a structure that satisfies the following chemical formula:
  • Rl R2 wherein n is 0,1 or 2, and R ⁇ and R* may be the same or different, and represent hydrogen, a C ⁇ . ⁇ alkyl group, notably a methyl, ethyl, or propyl group, or a functional group through which the polymer can be crosslinked, such as hydroxy, epoxy.
  • Said structure is preferably incorporated in the form of a side group, pendant from a polymeric backbone.
  • the polymeric backbone can, in principle, be of any type, including polyurethanes, polycarbonates, polyimides, polyesters, and polyacrylates.
  • the polymeric backbone may be cross-linked.
  • Preferred backbones are polyurethanes, polycarbonates, and polyimides.
  • NLO polymers comprising the above moiety have been described before. See EP 363 237, WO 91/13116, US 5 187 234, WO
  • the optical waveguide component of the present invention can be made electro-op - cally active.
  • E/O-active, or NLO materials are known.
  • non-linear charge polarization occurs under the influence of an external electric field.
  • Non-linear electric polar. Sc'.ion may give rise to several optically non-linear phenomena such as frequency doubling and Pockels effect.
  • Obtaining the desired NLO effect in polymeric materials macroscopically requires that first the groups present in such a material, mostly hyperpolarisable side groups, be aligned (poled).
  • Such poling is usually effected by exposing the polymeric material to electric (dc) voltage, the so-called poling field, with such heating as will render the polymeric chains sufficiently mobile for orientation.
  • an electron donor and an electron acceptor should be attached to the ethenyl dimethylcyclohexenylidene structure so as to form a Dn-A group in which the rr-system comprises the ethenyl dimethylcyclohexenylidene structure.
  • Donor groups for such Dn-A-systems can be those known in the art as "+M” groups, i.e., functional groups which are electron-donating by the resonance effect, see J. March Advanced Organic Chemistry, thir edition (1985), pages 237-238.
  • “+M” groups are -0", -S " , a ino groups including -NR2, NHR, and NH2, amido groups i attached via nitrogen (-NHC0R), alkoxy groups, hydroxyl groups, este groups if attached via the alcoholic oxygen (-0C0R), thiol ethers (-SR), mercapto groups (-SH), halogen (Br, I, Cl , F) , alkyl and aryl groups.
  • R is used to indicate alkyl groups i general. These include methyl, ethyl, propyl, butyl, pentyl hexyl , and larger groups. Included are all isomers. Such groups can be attached via any carbon atom in the alkyl chain.
  • Acceptor groups can be described analogously as "-M” groups. Some examples are nitrogen, cyano, carboxylic acid, carboxylic ester if attached via carboxylic carbon (-C0OR), amido if attached via carboxylic carbon (-CONH2, -CONHR, CONR2), aldehydo (-CH0), keto (-C0R), sulfonyl (-SC R), sulfonate (-SO2OR), nitroso, and aryl (which is capable of both kinds of resonance effects).
  • Suitable acceptor groups include barbiturates and thiobarbiturates, i.e. groups satisfying one of the following formulae:
  • the donor side has to be appropriately functionalized.
  • a diol function is employed, e.g. as in Formula II: (Formula II)
  • diol groups i.e., the groups forming the moiety
  • the preferred donor groups are alkoxy and amino groups.
  • the preferred acceptor groups are cyano and nitro groups, with dicyano having the highest preference.
  • the following structure is preferred for the bleachable NLO moieties: CN
  • the bleachable moiety according to the invention preferably is incorporated into a polyurethane by reacting a di isocyanate, preferably isophorone diisocyanate, with the diol [3-[2- [4- [bis (2-hydroxyethyl) amino] phenyl ] ethenyl ] 5,5-dimethyl-2-cyclo hexene-1-ylidene]- propane dinitrile, i.e., a diol satisfing the following chemical formula:
  • R* and R* have the meaning given above.
  • Other preferred diol moieties include dihydroxypyrrolidine and dihydroxydithiaful vene groups.
  • diols may be incorporated into the monomer mixture to enhance the polyurethane 's properties, such as Tg, mechanical strength, etc.
  • diols having a thermally or photochemically cross- linkable group e.g., an allyl group, epoxy group, or isocyanate group.
  • the invention also pertains to cross-linkable and already cross-linked polyurethanes obtained from a monomer mixture comprising a diol according to formula II and diisocyanates, with there being a cross-linkable group either in the monomer mixture as an additional compound or inthe diisocyanate.
  • Polyimides incorporating the above moiety are preferably prepared by reacting a tetracarboxylic dianhydride with a diamine of the following formula:
  • Ri and R* have the meaning given above
  • Ar stands for a substituted or unsubstituted aromatic ring such as phenylene, naphthylidene, tolylene, and the like.
  • a tetracarboxylic acid for the reaction with the diamine, and thereafter to effect ring closure of the resulting polyamic acid.
  • Preferred tetracarboxylic acids are pyromellitic acid, benzophenon tetracarboxylic acid, 2,2-isopropylidene di(phthalic acid), and particularly hexafluoro 2,2-isopropylidene di(phthalic acid).
  • the corresponding dianhydrides are preferred over the free acids.
  • the polyimides prepared from the diamine of Formula VI and a tetracarboxylic acid or the dianhydride thereof exhibit int.al. the following advantageous properties: they allow excellent definition of the waveguide channels, are stable at high temperatures (above 200 C C and higher), and have a high electro-optical coefficient upon poling. In these respects the instant polyimides are an improvement over known NLO polyimides such as those described in WO 91/03001.
  • P stands for -Cl , 0-R, an imidazole group or -O-Ph
  • Q stands for -Cl, 0-R, an imidazole group or -O-Ph
  • R stands for an alkylene group having 1-6 carbon atoms
  • Ph stands for phenyl
  • A stands for -Ph-, halogenated -Ph-, -Ph-C(CH3)2 ⁇ Ph-, -Ph-C(CF 3 ) 2 -Ph, -Ph-C(S0 2 )2-Ph-.
  • a cycloalkylene group having 1-24 carbon atoms, a halo substituted cycloalkylene group having 1-24 carbon atoms, an arylene group having 1-20 carbon atoms, or a naphthalene group is an integer from 0 to 5, with the A-groups being the same or different.
  • this compound is a bischloroformate of bisphenol-A or hexafluorobisphenol-A.
  • the resulting polycarbonates display excellent bleaching and e/o properties, have relatively high Tgs of above 150°C, and low optical attenuation (low loss of propagating light).
  • diols may be incorporated into the monomer mixture to enhance the polycarbonate's properties, such as Tg, mechanical strength, etc.
  • diols having a thermally or photochemically cross- linkable group e.g., an allyl group, epoxy group, or isocyanate group.
  • diols according to formula II use may be made of compounds according to formula VII containing a thermally or photoche ically cross-linkable group, e.g., an allyl group, epoxy group, or isocyanate group.
  • the invention also pertains to cross-linkable and already cross-linked polycarbonates obtained from a monomer mixture comprising a diol according to formula II and a compound according to formula VII, with there being a cross-linkable group either in the monomer mixture as an additional compound, or in a compound according to formula VII.
  • the polycarbonates can be obtained by reacting diols according to Formula II in a basic solvent such as pyridine or THF containing a tertiary amine with an equivalent amount of a compound according to Formula VII.
  • a quantity of chain stopper may be added, e.g., phenol.
  • Comp. Pol. Sci . The Synthesis, Characterization, Reactions and Applications of Polymers Vol. 5 (Pergamon Press), Chapter 20, pp. 345-356.
  • the making of polymeric layered waveguide components in general is known to the man skilled in the art.
  • the consecutive layers may be coated onto a substrate in the form of, say, a polymer solution, preferably by means of spin coating, and then evaporating the solvent.
  • the waveguide channels are defined laterally by a process comprising the steps of providing a layered planar waveguide component with a mask selectively covering portions thereof and then irradiating it through said mask so as to change the refractive index of the portions of the waveguiding material not covered.
  • the process generally involves the following steps:
  • an electro-optically active waveguide it is possible to refrain from removing the metal mask, as it can be used as an electrode.
  • the metal layer is removed as redundant.
  • the bleaching wavelength for the optical waveguide components according to the invention depends on the electron- donor and -acceptor groups chosen. It is preferably within the charge- transfer absorption region of the side-group. For most materials this will be within a range of from 350 to 750 nm. For the preferred structure of Formula IV, this range is 400-550 nm.
  • the bleaching wavelength for this side group is preferably of from 490-500, ⁇ max being 493 nm.
  • the guiding layer may not be necessary for the guiding layer to be bleached throughout the entire layer thickness. What is essential is that in the area of the desired channels the light guided through the guiding layer experiences an effective index of refraction that is sufficiently higher than the refractive index of the surrounding material. In the case of a relatively low local refractive index change, a greater bleaching depth will generally be needed to obtain the desired effective index change than in the case of a relatively high local refractive index change.
  • the invention also pertains to polymeric optical waveguide devices comprising a polymeric optical waveguide having a layered structure as indicated above, wherein the guiding layer comprises a pattern of waveguide channels having a higher refractive index than the surrounding polymeric material, the pattern being formed by photobleaching the surrounding material, wherein the guiding layer consists essentially of a polymer comprising moieties according to Formula I.
  • the guiding layer polymer comprises these moieties as pendant side groups.
  • a polyurethane having side groups in accordance with Formula V was prepared as follows. To 14 ml of DMF (dimethyl formamide) were added 3.77 g of [3-[2-[4-[bis (2-hydroxyethyl ) amino] phenyl] ethenyl] 5,5-dimethy1-2-cyclohexene-l-ylidene]-propane dinitrile (the diol of Formula V), and 2.22 g of isophorone diisocyanate. The reaction mixture was stirred at 100°C for 18 hours, cooled down to room temperature, precipitated in methanol , filtrated and dried. A polyurethane having an MW of 44000 and a Tg of 151°C resulted.
  • a three-layer planar waveguiding structure was prepared by successively spin coating and curing a bottom cladding (deflection layer) with a thickness of 3.47 ⁇ m, a core layer (guiding layer) with a thickness of 1.81 ⁇ m, and a top cladding (deflection layer) with a thickness of 3.42 ⁇ m.
  • a polished Si wafer was used as substrate.
  • Th bottom and top claddings were spin cast from a solution of HEMA/styrene copolymer and Desmodur N3390 in cyclopentanone. The inde of refraction at 1300 nm of the resulting cladding layers wa determined from prism coupling measurements to be 1.552.
  • the core layer was spin cast from a solution of the above polyurethane in cyclopentanone.
  • the refractive index of the unpoled core layer at 1300 nm was measured to be 1.654.
  • the bottom and core layers were both cured for 90 minutes on a hot stage at 140°C.
  • the top cladding was cured at the same temperature for 150 minutes. After the curing of the top cladding, a 100-nm thick Au layer was vacuum deposited on top of the waveguiding structure.
  • a voltage of -1080 V was applied to the Au top electrode and the optoboard was heated to 135°C, enabling the pendant side groups of the guiding layer polyurethane to align themselves along the applied field. After 10 minutes at 135°C, the component was cooled to 122°C in 4 minutes, at which temperature it was kept for another 4 minutes. Subsequently, the component was cooled to room temperature in a few minutes and the applied voltage was removed.
  • the Au film was patterned into a mask for photobleaching of the core.
  • a photoresist layer was spin coated on top of the Au film and baked for 2 minutes at 90°C. After exposure of the photoresist through a mask containing the desired waveguide pattern, the photoresist was developed and the uncovered regions of the Au layer were removed using a wet-etching process. Only the Au above the channel waveguides to be defined was retained. The uncovered areas were photobleached through irradiation with light of a wavelength of 420(+20)nm and an intensity of 15 mW/cm 2 .
  • two sections each containing 20 directional couplers with a coupling length varying from 96/03674 PCI7EP95/02880
  • the Au mask was stripped and a new 100-nm thick Au layer was vacuum deposited on top of the optoboard.
  • This Au film was patterned according to the procedure outlined above so as to provide electrodes above the branches of the Mach-Zehnder interferometers.
  • the change in the effective index of refraction of the exposed areas with respect of that of the unexposed channels was derived from the experimentally determined beat length of the directional couplers.
  • the irradiation doses of 36 J/cm 2 and 54 J/cm 2 were found to result in a lowering of the effective index of refraction at 1300 nm of 0.0044 and 0.0056 respectively.
  • the electro-optic activity at 1300 nm was assessed by measuring V ⁇ L for the Mach-Zehnder interferometers, which was found to be 16.9 Vcm.
  • L is the length of the electrodes above the arms of the MZI.
  • a polyurethane having side groups derived from 4-di-(2-hydroxyethyl)amino-4'-nitrostilbene was prepared in accordance with Example 8 of EP 350 112. This polymer was chosen for comparison as up to now it has given optimal results in respect of waveguide channel formation and electro-optical activity.
  • a three-layer plana waveguiding structure was prepared and poled, the bottom claddin having a thickness of 3.22 ⁇ m, the core having a thickness of 1.66 ⁇ m and the top cladding having a thickness of 3.23 ⁇ m.
  • the unpoled cor layer had a refractive index at 1300 nm of 1.622.
  • Bleaching was conducted choosing such irradiation time that th accumulated irradiation dose amounted to 252 J/cm 2 .
  • 2 directional couplers with a coupling length varying from 1 mm to 20 m and a number of Mach-Zehnder interferometers were patterned in th three-layer polymeric structure.
  • the change in the effective index of refraction of the exposed areas with respect of that of the unexposed channels was derived from th experimentally determined beat length of the directional couplers. Th irradiation dose of 252 J/cm 2 was found to result in a lowering of th effective index of refraction of 0.005 at 1300 nm.
  • the electro-optic activity at 1300 nm was assessed by measuring V ⁇ - L for the Mach- Zehnder interferometers, which was found to be 23.4 Vcm.
  • L is the length of the electrodes above the arms of the MZI.
  • a polycarbonate having side groups in accordance with formula V was prepared as follows. To 19.4 g of [3-[2-[4-[bis (2-hydroxyethyl ) amino] phenyl] ethenyl] 5,5-dimethyl-2-cyclohexene-l-ylidene]-propane dinitrile (the diol of Formula V) and 40.0 g of hexafluorotetrabromobisphenol A bischloroformate in 400 ml of THF (tetrahydrofuran) there was added dropwise in one hour 8.3 ml of pyridine, at 0°C. The reaction mixture was allowed to heat up to 20 C C. After 18 hours of stirring, the reaction product was precipitated in ethanol . M.W.: 23000, Tg was measured to be 167-175°C.
  • a successfully bleached electro-optically active layered waveguide component was made following the procedure described in Example 1, using o-xylene instead of cyclopentanone for spincoating the top cladding.
  • a polycarbonate having a molecular weight of 16000 and a Tg of 141°C was prepared using 2,97 g of hexafluoro bisphenol-A bischloroformate, 2.43 g of the diol of Formula V, 1.04 ml of pyridine, and 30 ml of THF.
  • a successfully bleached electro-optically active layered waveguide component was made following the procedure described in Example 1, again using o-xylene for spincoating the top cladding.
  • a polyimide was prepared by reacting 4.12 g (8.25 mmoles) of the above diamine with 3.33 g (7.5 mmoles) of hexafluoro isopropylidene 2,2-di (phthalic anhydride) and 0.15 g (1.5 mmoles) of maleic anhydride in 70 ml of dimethyl aceta ide. The reaction was conducted at 20 C C overnight. Thereafter 10 ml of toluene were added, followed by 16 hours of stirring at reflux temperature (employing a Dean-Stark apparatus to drive off water, and affect imide ring closure).
  • a successfully bleached electro-optically active layered waveguide component was made following the procedure described in Example 1.

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

Abstract

L'invention concerne un élément de guide d'ondes optique présentant une structure en couches comprenant une couche de guidage polymérique placée entre deux couches de déviation à indice de réfraction inférieur à la couche de guidage. La couche de guidage polymérique comprend des fractions qui sont sensibles à une modification de l'indice de réfraction provoquée par un rayonnement approprié. La couche de guidage polymérique est rendue photoblanchissable. Selon l'invention, lesdites fractions comprennent une structure répondant à la formule suivante (I), dans laquelle n représente 0, 1 ou 2, et R1 et R2 peuvent être identiques ou différents, et représentent hydrogène, un groupe alkyle C1-6, en l'occurence un groupe méthyle, éthyle, ou propyle, ou bien un groupe fonctionnel permettant la réticulation du polymère, tel qu'isocyanate, hydroxy ou époxy. On a découvert que ces structures permettent d'obtenir de manière inattendue des propriétés de blanchiment bénéfiques.
PCT/EP1995/002880 1994-07-22 1995-07-19 Element de guide d'ondes optique pouvant etre blanchi WO1996003674A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP94202145.2 1994-07-22
EP94202145 1994-07-22
EP94202319 1994-08-16
EP94202319.3 1994-08-16

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5908916A (en) * 1995-03-13 1999-06-01 Akzo Nobel N.V. Cross-linked or cross-linkable optical polycarbonates and optical components comprising said optical polycarbonates
JP2016006079A (ja) * 2009-08-24 2016-01-14 国立研究開発法人情報通信研究機構 ２次非線形光学化合物及びそれを含む非線形光学素子
CN114478318A (zh) * 2022-01-26 2022-05-13 河南应用技术职业学院 二腈异佛尔酮衍生物、其制备方法及应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0350112A1 (fr) * 1988-07-04 1990-01-10 Akzo Nobel N.V. Polyuréthanes préparés à partir de diols optiquement actifs
EP0359648A1 (fr) * 1988-09-16 1990-03-21 Flamel Technologies Polyuréthannes, actifs en optique non linéaire et matériaux les contenant dispositif optique les contenant et procédés de fabrication de ces composés et matériaux
EP0363237A2 (fr) * 1988-09-16 1990-04-11 Flamel Technologies Polymères et matériaux les contenant, actifs en optique non linéaire, procédé de fabrication de ces polymères et matériaux et dispositif optoélectrique les contenant
US5142605A (en) * 1988-09-08 1992-08-25 Barr & Stroud Limited Integrated optic components

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0350112A1 (fr) * 1988-07-04 1990-01-10 Akzo Nobel N.V. Polyuréthanes préparés à partir de diols optiquement actifs
US5142605A (en) * 1988-09-08 1992-08-25 Barr & Stroud Limited Integrated optic components
EP0359648A1 (fr) * 1988-09-16 1990-03-21 Flamel Technologies Polyuréthannes, actifs en optique non linéaire et matériaux les contenant dispositif optique les contenant et procédés de fabrication de ces composés et matériaux
EP0363237A2 (fr) * 1988-09-16 1990-04-11 Flamel Technologies Polymères et matériaux les contenant, actifs en optique non linéaire, procédé de fabrication de ces polymères et matériaux et dispositif optoélectrique les contenant
US4985528A (en) * 1988-09-16 1991-01-15 Rhone-Poulenc Chimie Novel nonlinearly optically active polyurethanes

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5908916A (en) * 1995-03-13 1999-06-01 Akzo Nobel N.V. Cross-linked or cross-linkable optical polycarbonates and optical components comprising said optical polycarbonates
JP2016006079A (ja) * 2009-08-24 2016-01-14 国立研究開発法人情報通信研究機構 ２次非線形光学化合物及びそれを含む非線形光学素子
US9977150B2 (en) 2009-08-24 2018-05-22 National Institute Of Information And Communications Technology Second-order nonlinear optical compound and nonlinear optical element comprising the same
US10754064B2 (en) 2009-08-24 2020-08-25 National Institute Of Information And Communications Technology Second-order nonlinear optical compound and nonlinear optical element comprising the same
CN114478318A (zh) * 2022-01-26 2022-05-13 河南应用技术职业学院 二腈异佛尔酮衍生物、其制备方法及应用
CN114478318B (zh) * 2022-01-26 2023-08-18 河南应用技术职业学院 二腈异佛尔酮衍生物、其制备方法及应用

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