WO2013024840A1 - 高屈折率クラッド材料及び電気光学ポリマー光導波路 - Google Patents
高屈折率クラッド材料及び電気光学ポリマー光導波路 Download PDFInfo
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- WO2013024840A1 WO2013024840A1 PCT/JP2012/070627 JP2012070627W WO2013024840A1 WO 2013024840 A1 WO2013024840 A1 WO 2013024840A1 JP 2012070627 W JP2012070627 W JP 2012070627W WO 2013024840 A1 WO2013024840 A1 WO 2013024840A1
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Images
Classifications
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- 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
- G02B1/048—Light guides characterised by the cladding material
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- C—CHEMISTRY; METALLURGY
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- 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
- G02F1/061—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 electro-optical organic material
- G02F1/065—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 electro-optical organic material in an optical waveguide structure
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- 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
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- G02F1/35—Non-linear optics
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- 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
- G02F1/365—Non-linear optics in an optical waveguide structure
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- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
- C08G2261/3162—Arylamines
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
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- G—PHYSICS
- G02—OPTICS
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- 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
- G02F1/0009—Materials therefor
- G02F1/0018—Electro-optical materials
Definitions
- the present invention relates to an optical waveguide containing an organic nonlinear optical compound used for optical switches, optical information processing such as optical modulation, optical communication, and the like.
- Nonlinear optical materials such as lithium niobate and potassium dihydrogen phosphate have been widely used as nonlinear optical materials exhibiting this effect.
- Nonlinear optical materials have attracted attention, and studies for their practical use have been activated.
- polymer materials having extremely high electro-optic properties compared to conventional inorganic materials are highly expected for the realization of ultra-high speed modulation devices and low power consumption device technologies.
- These polymer materials uniformly disperse the organic nonlinear optical compound in the polymer matrix, or bind to the polymer side chain, and orient the compound molecules to develop the electro-optical characteristics.
- the nonlinear optical compound a push-pull type compound having an electron donating property for one of the ⁇ -conjugated chains and an electron attractive property for the other is used.
- a polymer material is applied on a substrate having an alignment film on the surface, and the substrate orientation of the alignment film is used, or a polymer material heated near or above the glass transition temperature is used.
- An electric field poling method for aligning by applying a voltage by a corona discharge of a pair of electrodes or air is known. Among these, the electric field poling method is preferable from the viewpoint of the simplicity of the apparatus and the high degree of orientation of the nonlinear optical compound.
- the optical waveguide required when using a nonlinear optical material in a light propagation type device is a laminated layer in which a polymer core containing a nonlinear optical compound and a cladding having a lower refractive index than the core are formed above and below or around the polymer core. Formed as a structure.
- the electrical resistivity of the core portion tends to decrease.
- the clad portion tends to have a relatively higher electrical resistivity than the core portion, and as a result, an efficient voltage cannot be applied to the core portion, and sufficient electro-optical characteristics cannot be exhibited.
- Patent Document 1 reports a method of adding a polymer compound having an alkylammonium group to the clad material to reduce the resistance value of the clad part and improve the poling efficiency.
- the inventors of the present invention incorporated a nonlinear optical compound that has been included only in the core portion so far into the cladding portion, so that the resistance value of the cladding can be reduced.
- the inventors have found that the resistance can be made extremely lower than the resistance value, and have completed the present invention.
- the present invention relates, as a first aspect, to a cladding material for an optical waveguide, characterized by containing a polymer compound having a triarylamine structure and a nonlinear optical compound.
- the present invention relates to the cladding material according to the first aspect, wherein the nonlinear optical compound is a compound having a tricyano-bonded furan ring.
- the compound which has the said tricyano bond furan ring is related with the clad material as described in a 2nd viewpoint which is a compound represented by following formula (1).
- R 1 and R 2 each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms).
- R 3 to R 6 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxy group, an alkoxy group having 1 to 10 carbon atoms, or an alkylcarbonyloxy group having 2 to 11 carbon atoms.
- the high molecular compound containing the said triarylamine structure is related with the clad material as described in a 1st viewpoint which has a repeating unit represented by Formula (2) or Formula (3).
- Ar 2 to Ar 4 each independently represents any divalent organic group represented by the following formulas (4) to (8),
- Z 1 and Z 2 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or any monovalent organic represented by the following formulas (9) to (12)
- R 15 to R 18 each independently represents a hydrogen atom, a carbon atom number of 1 to 5 represents an alkyl group, a hydroxyalkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom.
- R 19 to R 52 each independently represents a hydrogen atom, a carbon atom number of 1 to 5 represents an alkyl group, a
- Haloalkyl group, phenyl group, OR 77 , COR 77 , COOR 77 , or NR 77 R 78 group (in these formulas, R 77 and R 78 are each independently a hydrogen atom, an alkyl having 1 to 5 carbon atoms) Group, a hydroxyalkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or a phenyl group.)
- the said repeating unit is related with the clad material as described in a 4th viewpoint represented by Formula (13).
- the present invention relates to the cladding material according to the fifth aspect, wherein Z 1 is a monovalent organic group represented by the formula (9), and Z 2 is a hydrogen atom.
- Z 1 is a monovalent organic group represented by the formula (9)
- Z 2 is a hydrogen atom.
- an optical waveguide comprising a core and a clad having a refractive index smaller than that of the core surrounding the entire outer periphery thereof, wherein the clad is any one of the first aspect to the sixth aspect.
- the present invention relates to an optical waveguide made of a material.
- the present invention relates to the optical waveguide according to the seventh aspect, wherein the core includes a nonlinear optical compound having a tricyano-bonded furan ring represented by the formula (1) or a derivative thereof.
- R 1 and R 2 each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms).
- R 3 to R 6 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxy group, an alkoxy group having 1 to 10 carbon atoms, or an alkylcarbonyloxy group having 2 to 11 carbon atoms.
- the method for manufacturing an optical waveguide according to the eighth aspect comprising a core and a clad surrounding the core and having a smaller refractive index than the core, Forming a lower cladding using the cladding material according to any one of the first to sixth aspects; Forming a core containing a nonlinear optical compound having a tricyano-bonded furan ring represented by the formula (1) according to the eighth aspect or a derivative thereof on the lower clad; and Forming a top clad on the core using the clad material according to any one of the first aspect to the sixth aspect; Before and / or after the step of forming the upper clad, comprising a step of subjecting the nonlinear optical compound or derivative thereof contained in the core to a polarization orientation treatment,
- the present invention relates to a method for manufacturing the optical waveguide.
- the method for manufacturing an optical waveguide according to the eighth aspect comprising a core and a clad surrounding the core and having a refractive index smaller than that of the core, Forming a lower cladding using the cladding material according to any one of the first to sixth aspects; A resist layer that is sensitive to ultraviolet rays is formed on the lower clad, and the surface of the resist layer is irradiated and developed with ultraviolet light through a photomask to form a core mask pattern.
- the present invention relates to a method of manufacturing a ridge type optical waveguide.
- the eleventh aspect relates to the manufacturing method according to the ninth aspect or the tenth aspect, wherein the polarization orientation treatment is an electric field application treatment using an electrode.
- the polarization orientation treatment is an electric field application treatment using an electrode.
- the high molecular compound which has a repeating unit represented by Formula (2) or Formula (3).
- Ar 2 to Ar 4 each independently represents any divalent organic group represented by the following formulas (4) to (8), In 2), Z 1 and Z 2 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or any monovalent organic represented by the following formulas (9) to (12) Represents a group (provided that Z 1 and Z 2 do not simultaneously become the alkyl group), and in formula (3), R 15 to R 18 each independently represents a hydrogen atom (provided that R 15 to R 18 is not a hydrogen atom at the same time.) Or represents a hydroxyalkyl group having 1 to 5 carbon atoms.) (Wherein R 19 to R 52 each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an epoxy group, a carboxyl group, a hydroxy group, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom) Represents an atom.) (Wherein R 53 to R 76 are
- the present invention relates to the polymer compound according to the twelfth aspect, in which the repeating unit is represented by the formula (13). (In the formula, Z 1 and Z 2 represent the same meaning as described above.) As a fourteenth aspect, the present invention relates to the polymer compound according to the thirteenth aspect, wherein Z 1 is a monovalent organic group represented by the formula (9), and the Z 2 is a hydrogen atom.
- the clad material of the present invention has a very low resistivity, it can be used as a clad for an optical waveguide to form an optical waveguide capable of simply and efficiently applying an electric field to the core portion.
- FIG. 1 is a process diagram showing a manufacturing process of a ridge type optical waveguide manufactured in an example.
- FIG. 2 is a diagram showing a conceptual diagram of the shape of the ridge type optical waveguide manufactured in the example.
- the present invention is directed to a cladding material for an optical waveguide, which contains a polymer compound containing a triarylamine structure and a nonlinear optical compound.
- the present invention is also directed to an optical waveguide manufactured using the cladding material and a method of manufacturing the optical waveguide.
- the present invention will be described in more detail.
- the polymer compound containing a triarylamine structure used in the present invention is not particularly limited, but is preferably represented by the following formula (2) or formula (3) containing a triarylamine skeleton as a branch point. It is a high molecular compound which has a repeating unit.
- Ar 2 to Ar 4 each independently represents any divalent organic group represented by the formulas (4) to (8).
- R 19 to R 52 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an epoxy group, a carboxyl group, a hydroxy group, or 1 to 5 represents an alkoxy group or a halogen atom.
- the alkyl group having 1 to 5 carbon atoms may have a branched structure or a cyclic structure, and may be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, Examples thereof include an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a neopentyl group, and a cyclopentyl group.
- the alkoxy group having 1 to 5 carbon atoms may have a branched structure or a cyclic structure, and is a methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropoxy group, n-butoxy group, isobutoxy group.
- the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- Ar 2 to Ar 4 are preferably a substituted or unsubstituted phenylene group represented by the formula (4), and particularly preferably a phenylene group in which all of R 19 to R 22 represent hydrogen atoms.
- Z 1 and Z 2 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or any monovalent group represented by the following formulas (9) to (12) Represents an organic group. However, Z 1 and Z 2 do not simultaneously become the alkyl group. Examples of the alkyl group having 1 to 5 carbon atoms include the same groups as those described above for R 19 to R 52 .
- R 53 to R 76 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group having 1 to 5 carbon atoms, A haloalkyl group having 1 to 5 carbon atoms, a phenyl group, an OR 77 , COR 77 , COOR 77 , or NR 77 R 78 group;
- R 77 and R 78 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group having 1 to 5 carbon atoms, or a haloalkyl group having 1 to 5 carbon atoms.
- alkyl group having 1 to 5 carbon atoms examples include the same groups as those described above for R 19 to R 52 .
- the hydroxyalkyl group having 1 to 5 carbon atoms may have a branched structure or a cyclic structure, and is a hydroxymethyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, or a 1-hydroxypropan-2-yl. Group, 2-hydroxycyclopropyl group, 4-hydroxybutyl group, 5-hydroxypentyl group, 1-hydroxycyclopentyl group and the like.
- the haloalkyl group having 1 to 5 carbon atoms may have a branched structure or a cyclic structure, such as a fluoromethyl group, a trifluoromethyl group, a bromodifluoromethyl group, a 2-chloroethyl group, a 2-bromoethyl group, 1 , 1-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2, -tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl Group, 3-bromopropyl group, 2,2,3,3-tetrafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, 1,1,1,3,3,3- Hexafluoropropan-2-yl group, 3-bromo-2-methylpropyl group, 2,2,3,3-tetrafluorocyclopropyl
- Z 1 and Z 2 are each independently preferably a hydrogen atom, a 2-thienyl group, a 3-thienyl group, or a substituted or unsubstituted phenyl group represented by the formula (9).
- Z 1 and Z 2 Any one of 2 is a hydrogen atom and the other is a hydrogen atom, a 2-thienyl group, a 3-thienyl group, or a substituted or unsubstituted phenyl group represented by the formula (9), particularly any of R 53 to R 57
- One of these is more preferably a hydroxyalkoxyphenyl group of a hydroxyalkoxy group.
- R 15 to R 18 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group having 1 to 5 carbon atoms, or a 1 to 5 carbon atom.
- examples of the alkyl group having 1 to 5 carbon atoms, the alkoxy group having 1 to 5 carbon atoms, and the halogen atom include the same groups as those described above for R 19 to R 52 .
- Examples of the hydroxyalkyl group having 1 to 5 carbon atoms are the same as those described above for R 53 to R 76 .
- the polymer compound containing a triarylamine structure preferably has at least one repeating unit among the four structures represented by the following formula (14).
- the high molecular compound which has a repeating unit represented by the said Formula (2) or Formula (3) ie, the high molecular compound which preferably has a repeating unit represented by the said Formula (13), and said Formula (14)
- the high molecular compound which has at least 1 among the repeating units represented by these is also the object of this invention.
- the polymer compound targeted by the present invention is a polymer compound having a repeating unit represented by the formula (2) or formula (3), and the polymer compound is represented by the formula (2).
- Ar 2 to Ar 4 are each independently any divalent organic group represented by formulas (4) to (8) (formulas (4) to (8)).
- R 19 to R 52 each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an epoxy group, a carboxyl group, a hydroxy group, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom.
- Z 1 and Z 2 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or the above formulas (9) to (12).
- R 53 ⁇ R 76 are each independently, Atom (provided that, R 53 ⁇ R 57, R 58 ⁇ R 64, R 65 ⁇ R 67, or R 68 ⁇ R 76 are not hydrogen atoms at the same time.), Or hydroxy having 1-5 carbon atoms
- R 15 to R 18 are each independently a hydrogen atom (wherein R 15 to R 18 are not simultaneously hydrogen atoms), or a hydroxyalkyl having 1 to 5 carbon atoms.
- the average molecular weight of the polymer compound containing a triarylamine structure used in the present invention is not particularly limited, but the weight average molecular weight is preferably 1,000 to 2,000,000.
- the weight average molecular weight of the polymer compound is 1,000 or more, when used as a cladding material, the film quality when a thin film is formed can be made more uniform, and when it is 2,000,000 or less, the solvent It becomes easy to handle without significantly lowering its solubility in
- the weight average molecular weight is more preferably 2,000 to 1,000,000.
- the weight average molecular weight in this invention is a measured value by gel permeation chromatography (polystyrene conversion).
- the polymer compound can be obtained by polycondensation of a triarylamine compound and an aldehyde compound under acidic conditions.
- aldehyde compound used for the production of the polymer compound containing the triarylamine structure examples include formaldehyde, paraformaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, n-valeraldehyde, 2-methylbutyraldehyde, 3-methyl -2-Saturated aliphatic aldehydes such as butenal and hexylaldehyde; heterocyclic aldehydes such as thiophene aldehyde; benzaldehyde, tolylaldehyde, hydroxymethylbenzaldehyde, trifluoromethylbenzaldehyde, phenylbenzaldehyde, salicylaldehyde, anisaldehyde, (2 -Hydroxyethoxy) benzaldehyde, terephthalaldehyde, acetylbenzalde
- Examples of the acid catalyst used in the production of the polymer compound include mineral acids such as sulfuric acid, phosphoric acid and perchloric acid; organic sulfonic acids such as p-toluenesulfonic acid and p-toluenesulfonic acid monohydrate; Carboxylic acids such as formic acid and oxalic acid can be used.
- the amount of the acid catalyst used is variously selected depending on the kind thereof, but is usually 0.001 to 10,000 parts by mass, preferably 0.01 to 1,000 parts by mass with respect to 100 parts by mass of the triarylamine compound. Part, more preferably 0.1 to 100 parts by weight.
- the above condensation reaction can be carried out without a solvent, but is usually carried out using a solvent. Any solvent that does not inhibit the reaction can be used.
- cyclic ethers such as tetrahydrofuran (THF) and 1,4-dioxane; N, N-dimethylformamide (DMF), N, N— Amides such as dimethylacetamide (DMAc) and N-methyl-2-pyrrolidone (NMP); Ketones such as isobutyl methyl ketone and cyclohexanone; Halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene And aromatic hydrocarbons such as benzene, toluene and xylene. These solvents can be used alone or in combination of two or more. In particular, cyclic ethers are preferred.
- the reaction temperature during the condensation is usually 40 to 200 ° C.
- the reaction time is variously selected depending on the reaction temperature, but is usually about 30 minutes to 50 hours.
- the polymer compound obtained as described above has a weight average molecular weight of usually 1,000 to 2,000,000, preferably 2,000 to 1,000,000 as described above.
- the nonlinear optical compound used in the present invention is a ⁇ -conjugated compound having an electron-donating group at one end of the ⁇ -conjugated chain and an electron-withdrawing group at the other end, and preferably has a high molecular hyperpolarizability ⁇ .
- the electron donating group include a dialkylamino group
- examples of the electron withdrawing group include a cyano group, a nitro group, and a fluoroalkyl group.
- the nonlinear optical compound used in the present invention includes a nonlinear optical compound having a tricyano-bonded furan ring, and specifically, a compound represented by the following formula (1) is preferable.
- R 1 and R 2 each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an aryl having 6 to 10 carbon atoms.
- the alkyl group having 1 to 10 carbon atoms may have a branched structure or a cyclic structure, and includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, Isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, cyclopentyl, n-hexyl, cyclohexyl, n-octyl, n-decyl, 1-adamantyl, benzyl, A phenethyl group etc.
- Examples of the aryl group having 6 to 10 carbon atoms include phenyl group, tolyl group, xylyl group, and naphthyl group.
- Examples of the substituent include amino group; hydroxy group; alkoxycarbonyl group such as methoxycarbonyl group and tert-butoxycarbonyl group; trimethylsilyloxy group, tert-butyldimethylsilyloxy group, tert-butyldiphenylsilyloxy group, and triphenylsilyl.
- Silyloxy groups such as oxy groups; halogen atoms and the like.
- R 3 to R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxy group, an alkoxy group having 1 to 10 carbon atoms, or 2 to 2 carbon atoms.
- examples of the alkyl group having 1 to 10 carbon atoms include the same ones as described above.
- the alkoxy group having 1 to 10 carbon atoms may have a branched structure or a cyclic structure, and is a methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropoxy group, n-butoxy group, isobutoxy group.
- the alkylcarbonyloxy group having 2 to 11 carbon atoms may have a branched structure or a cyclic structure, and may be an acetoxy group, propionyloxy group, butyryloxy group, isobutyryloxy group, cyclopropanecarbonyloxy group, penta Noyloxy, 2-methylbutanoyloxy, 3-methylbutanoyloxy, pivaloyloxy, hexanoyloxy, 3,3-dimethylbutanoyloxy, cyclopentanecarbonyloxy, heptanoyloxy, cyclohexane
- Examples include carbonyloxy group, n-nonanoyloxy group, n-undecanoyloxy group, 1-adamantanecarbonyloxy group, phenylacetoxy group, 3-phenylpropanoyloxy group and the like.
- Examples of the aryloxy group having 6 to 10 carbon atoms include phenoxy group, naphthalen-2-yloxy group, furan-3-yloxy group, and thiophen-2-yloxy group.
- Examples of the arylcarbonyloxy group having 7 to 11 carbon atoms include benzoyloxy group, 1-naphthoyloxy group, furan-2-carbonyloxy group, thiophene-3-carbonyloxy group and the like.
- silyloxy group having an alkyl group having 1 to 6 carbon atoms and / or a phenyl group examples include silyloxy groups such as a trimethylsilyloxy group, a tert-butyldimethylsilyloxy group, a tert-butyldiphenylsilyloxy group, and a triphenylsilyloxy group. Is mentioned.
- halogen atom are the same as those described for R 19 to R 52 above.
- R 7 and R 8 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or a 6 to 10 carbon atom.
- Examples of the alkyl group having 1 to 5 carbon atoms include the same groups as those described above for R 19 to R 52 .
- Examples of the haloalkyl group having 1 to 5 carbon atoms include the same groups as those described above for R 53 to R 76 .
- the aryl group having 6 to 10 carbon atoms include the same groups as those described above for R 1 and R 2 .
- R 7 and R 8 a methyl group-methyl group, a methyl group-trifluoromethyl group, and a trifluoromethyl group-phenyl group are preferable.
- Ar 1 represents a divalent organic group represented by the following formula (Ar 1 -a) or formula (Ar 1 -b).
- R 9 to R 14 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aryl group having 6 to 10 carbon atoms.
- Specific examples of the alkyl group having 1 to 10 carbon atoms, the aryl group having 6 to 10 carbon atoms, and the substituent include those exemplified above.
- Non-patent Document 1 Chem. Mater. 2001, 13, 3043-3050.
- the molecular hyperpolarizability ⁇ can be further increased by converting the dialkylanilino site, which is an electron donating group in the above structure, into various structures (Non-Patent Document 2: J. Polym. Sci. Part). A. 2011, Vol. 49, p47).
- the blending ratio of the polymer compound containing a triarylamine structure and the nonlinear optical compound is appropriately adjusted so as to have a resistance value lower than the resistance value of the core described later.
- the compounding amount of the nonlinear optical compound is 0.1 to 50 parts by mass, more preferably 0.5 to 10 parts by mass with respect to 100 parts by mass of the molecular compound.
- a crosslinking agent, a surfactant, a leveling agent, an antioxidant, a light stabilizer and the like can be blended within a range that does not affect the performance of the optical waveguide as a clad material.
- isocyanates including blocked isocyanates.
- general-purpose isocyanates for example, Coronate (registered trademark) 2507, 2513, AP staple (manufactured by Nippon Polyurethane Industry Co., Ltd.), Takenate (registered trademark) B-882N, B-830, B -815N, B-842N, B-846N, B-870N, B-874N (Mitsui Chemicals, Inc.), Barnock (registered trademark) D-500, D-550, B3- 867 (above, manufactured by DIC Corporation), Duranate (registered trademark) MF-B60X, MF-K60X (above, manufactured by Asahi Kasei Chemicals Corporation), Elastron (registered trademark) BN-P17, BN-04, BN-08, BN-44, BN-45 (above, manufactured by Daiichi Kogy
- the optical waveguide of the present invention is an optical waveguide comprising a core and a clad having a refractive index smaller than that of the core surrounding the entire outer periphery, wherein the clad includes the above-described triarylamine structure and a nonlinear optical compound It is formed from the clad material containing these.
- the core may be formed of a material having a refractive index larger than that of the formed cladding.
- the core preferably contains an organic nonlinear optical compound exhibiting a second-order nonlinear optical effect in a form dispersed in a polymer matrix or in a form bound to a side chain of the polymer compound.
- the organic nonlinear optical compound is preferably a nonlinear optical compound having a tricyano-bonded furan ring represented by the formula (1), for example.
- the nonlinear optical compound When the nonlinear optical compound is dispersed in the polymer matrix, the nonlinear optical compound needs to be uniformly dispersed at a high concentration in the matrix. Therefore, the polymer matrix has high compatibility with the nonlinear optical compound. It is preferable to show. In view of being used as a core of an optical waveguide, it is preferable to have excellent transparency and moldability.
- a polymer matrix material include resins such as polymethyl methacrylate, polycarbonate, polystyrene, silicone resin, epoxy resin, polysulfone, polyethersulfone, and polyimide.
- a method for dispersing in a polymer matrix there is a method in which a nonlinear optical compound and a matrix material are dissolved in an organic solvent or the like at an appropriate ratio, and applied to a substrate and dried to form a thin film.
- the side chain of the polymer compound when the nonlinear optical compound is bonded to the side chain of the polymer compound, the side chain of the polymer compound must have a functional group capable of forming a covalent bond with the nonlinear optical compound,
- Such functional groups include isocyanate groups, hydroxy groups, carboxyl groups, epoxy groups, amino groups, allyl halide groups, acyl halide groups, and the like. These functional groups can form a covalent bond with a hydroxy group or the like of a nonlinear optical compound having a tricyano-bonded furan ring represented by the above formula (1).
- the core is bonded to the unit structure of the polymer matrix and the nonlinear polymer compound in order to adjust the content of the nonlinear optical compound.
- the unit structure of the polymer compound may be in the form of copolymerization.
- the blending ratio of the nonlinear optical compound in the core is appropriately adjusted in order to increase the electro-optical characteristics.
- the blending amount of the nonlinear optical compound is 1 to 1,000 masses per 100 parts by mass of the polymer compound. Part, more preferably 10 to 100 parts by weight.
- the optical waveguide of the present invention is Forming a lower cladding using the aforementioned cladding material; Forming a core containing a nonlinear optical compound having a tricyano-bonded furan ring represented by the formula (1) or a derivative thereof on the lower clad; and Forming an upper clad on the core using the clad material described above, Before and / or after the step of forming the upper cladding, the nonlinear optical compound or its derivative contained in the core is manufactured by polarization orientation treatment.
- the step (3) is carried out following the step (1) without going through the step (2).
- a thin film to be a lower clad is formed using the clad material.
- the above clad material is appropriately dissolved or dispersed in an organic solvent to form a varnish (film forming material), which is spin coated, blade coated, dip coated, roll coated, bar coated And a method of coating and drying on an appropriate substrate using a coating method such as a die coating method, an ink jet method, and a printing method (such as relief printing, relief printing, flat plate, and screen printing).
- a coating method such as a die coating method, an ink jet method, and a printing method (such as relief printing, relief printing, flat plate, and screen printing).
- the spin coating method is preferable.
- the method for drying the solvent is not particularly limited.
- the solvent may be evaporated in a suitable atmosphere, that is, in an inert gas such as air or nitrogen, in a vacuum, or the like using a hot plate or an oven. Thereby, a thin film having a uniform film formation surface can be obtained.
- the drying temperature is not particularly limited as long as the solvent can be evaporated, but the drying temperature is preferably 40 to 250 ° C.
- the organic solvent used for the film forming material is not particularly limited as long as it can dissolve and disperse the clad material.
- organic solvents include aromatic hydrocarbons such as toluene, p-xylene, o-xylene, m-xylene, ethylbenzene and styrene; aliphatic hydrocarbons such as n-hexane and n-heptane.
- Halogenated hydrocarbons such as chlorobenzene, orthodichlorobenzene, chloroform, dichloromethane, dibromomethane, 1,2-dichloroethane; acetone, ethyl methyl ketone, isopropyl methyl ketone, isobutyl methyl ketone, butyl methyl ketone, diacetone alcohol, diethyl Ketones such as ketone, cyclopentanone, cyclohexanone; esters such as ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, ethyl lactate, ⁇ -butyrolactone; N, N-dimethylformamide, N, N-dimethyl Amides such as cetamide, N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone; methanol, ethanol, propanol,
- the substrate for forming the lower clad is not particularly limited, but a substrate having excellent flatness is preferable.
- a metal substrate, a silicon substrate, a transparent substrate, etc. are mentioned, It can select suitably by the form of an optical waveguide.
- the metal substrate include gold, silver, copper, platinum, aluminum, chromium, and the like
- the transparent substrate include substrates such as glass and plastic (polyethylene terephthalate).
- a known electrode can be used as the electrode.
- the lower electrode may be a metal vapor deposition layer or a transparent electrode layer.
- Preferred examples of the metal to be deposited include gold, silver, copper, platinum, aluminum, and chromium.
- preferable examples of the transparent electrode layer include indium tin oxide (ITO), fluorine-doped tin oxide (FTO), antimony-doped tin oxide, and the like.
- a resist layer that is sensitive to ultraviolet rays is formed on the lower clad, and a mask pattern of the core is formed on the surface of the resist layer by a photolithography method in which ultraviolet light is irradiated and developed through a photomask.
- the resist layer is not particularly limited as long as it is a material capable of exposing and developing a micropattern by the photolithography method, and the solvent used in the process does not elute the lower clad, but it is a positive type or a negative type. Photoresist materials are preferred. A mercury lamp, KrF laser, ArF laser or the like is used as a light source for pattern formation.
- the core pattern is transferred to the lower clad by dry etching using a gas using the mask pattern of the core of the resist layer as a mask.
- dry etching reactive ion etching using a gas species appropriately selected from the etching characteristics of the resist and the lower cladding, usually CHF 3 , O 2 , Ar, CF 4, etc. is preferably used.
- the resist layer used for the mask is removed with a solvent.
- a core including a nonlinear optical compound having a tricyano-bonded furan ring represented by the formula (1) or a derivative thereof is formed on the lower clad on which the core pattern is formed.
- the nonlinear optical compound having a tricyano-bonded furan ring represented by the formula (1) and the polymer matrix material are mixed in an appropriate organic solvent at an appropriate ratio.
- a method of forming a thin film by dissolving and forming a varnish form on a substrate, or having a derivative of a nonlinear optical compound having a tricyano-bonded furan ring represented by the above formula (1) in the side chain A method of forming a thin film by dissolving a polymer compound in a suitable organic solvent to form a varnish and coating and drying on a substrate can be mentioned.
- the varnish application method drying conditions, and organic solvent, those mentioned in the above-mentioned ⁇ (1) Step of forming lower clad> can be used. Note that an organic solvent that does not dissolve the lower clad is selected so that the lower clad is not eluted when the core is formed.
- the polarization alignment treatment is performed by an electric field poling method in which an electric field is applied to the nonlinear optical compound contained in the core.
- the polarization alignment treatment is performed at a temperature near or above the glass transition temperature of the core, and the polarization of the nonlinear optical compound is aligned in the electric field application direction by applying an electric field, and the alignment is maintained even after the temperature is returned to room temperature.
- electro-optical characteristics can be imparted to the core and the optical waveguide.
- an electric field a method of applying a DC voltage between electrodes arranged above and below the laminated structure or a method using corona discharge to the core surface is used. Is preferred.
- the apparatus and conditions used for sample preparation and physical property analysis are as follows.
- GPC gel permeation chromatography
- Equipment HLC-8220GPC manufactured by Tosoh Corporation Column: Showa Denko KF-804L + KF-805L Column temperature: 40 ° C
- Solvent tetrahydrofuran (THF)
- Detector RI
- 1 H NMR spectrum apparatus JNM-ECA700 manufactured by JEOL Ltd.
- Solvent CDCl 3 Internal standard: Tetramethylsilane (3) Differential scanning calorimeter Device: DSC 204F1 Phoenix (registered trademark) manufactured by NETZSCH Temperature increase rate: 30 ° C / min Measurement temperature: 25-300 ° C (4) Spin coater: MS-A100 manufactured by Mikasa Co., Ltd. (5) Hot plate device: ND-2 manufactured by AS ONE Corporation (6) Refractive index device: Multi-angle of incidence spectroscopic ellipsometer VASE manufactured by JA Woollam Japan (7) Resistivity Power supply: HSA4052 manufactured by NF Circuit Design Block Co., Ltd. Measuring device: 8340A type digital super high resistance / micro ammeter manufactured by ADC Co., Ltd.
- Example 1 Synthesis of polymer compound (1) having triarylamine structure Triphenylamine [manufactured by Tokyo Chemical Industry Co., Ltd.] 8.52 g (34.7 mmol) in a 100 mL reaction flask in a nitrogen atmosphere, 4- (2-hydroxyethoxy) benzaldehyde [manufactured by Tokyo Chemical Industry Co., Ltd.] 11.54 g (69.5 mmol), p-toluenesulfonic acid monohydrate [manufactured by Junsei Chemical Co., Ltd.] 1.32 g (6.95 mmol) And 20 g of 1,4-dioxane was added and dissolved.
- the temperature was raised to 85 ° C., and stirring was performed to initiate polymerization. After reacting for 5 hours and 30 minutes, the solution was cooled to room temperature, and 60 g of tetrahydrofuran and 4.72 g (77.7 mmol) of 28 mass% ammonia aqueous solution were added and stirred. This reaction solution was dropped into 500 g of methanol to perform reprecipitation. The deposited pale yellow solid was vacuum-dried, dissolved in 67 g of tetrahydrofuran, and re-precipitated by dropping it into a mixed solution of 4.72 g of 28% by mass aqueous ammonia, 450 g of methanol, and 50 g of ion-exchanged water.
- the obtained colorless solid was dried to obtain 6.88 g of a polymer compound (1) having a repeating unit of the following [A].
- the polymer compound (1) had a weight average molecular weight Mw measured in terms of polystyrene by GPC of 32,800, and the degree of dispersion: Mw (weight average molecular weight) / Mn (number average molecular weight) was 3.70.
- Example 2 Synthesis of polymer compound (2) having triarylamine structure Triphenylamine [manufactured by Tokyo Chemical Industry Co., Ltd.] 10.0 g (40.8 mmol), 3- (2-hydroxyethoxy) benzaldehyde [manufactured by Tokyo Chemical Industry Co., Ltd.] 13.6 g (81.5 mmol), p-toluenesulfonic acid monohydrate [manufactured by Junsei Chemical Co., Ltd.] 0.78 g (4.08 mmol) And 24 g of 1,4-dioxane was added and dissolved. The temperature was raised to 85 ° C., and stirring was performed to initiate polymerization.
- the obtained colorless solid was dried to obtain 7.90 g of a polymer compound (2) having a repeating unit of the following [B].
- the polymer compound (2) had a weight average molecular weight Mw measured in terms of polystyrene by GPC of 17,000 and a dispersity: Mw / Mn of 2.54.
- the temperature was raised to 85 ° C., and stirring was performed to initiate polymerization. After reacting for 3 hours and 30 minutes, the solution was cooled to room temperature, and 63 g of tetrahydrofuran and 1.49 g (24.5 mmol) of 28 mass% ammonia aqueous solution were added and stirred. This reaction solution was dropped into 400 g of methanol to perform reprecipitation. The deposited pale yellow solid was vacuum-dried, dissolved in 63 g of tetrahydrofuran, and dropped into a mixed solution of 1.49 g of 28 mass% ammonia aqueous solution, 400 g of methanol, and 100 g of ion-exchanged water for reprecipitation.
- the obtained colorless solid was dried to obtain 5.58 g of a polymer compound (3) having the following two repeating units [C].
- the polymer compound (3) had a weight average molecular weight Mw of 12,600 and a dispersity: Mw / Mn of 2.10.
- the temperature was raised to 85 ° C., and stirring was performed to initiate polymerization. After reacting for 70 minutes, the solution was cooled to room temperature, 120 g of tetrahydrofuran, and 8.95 g (147 mmol) of 28 mass% aqueous ammonia solution were added and stirred. This reaction solution was added dropwise to 560 g of methanol to perform reprecipitation. The precipitated pale yellow solid was vacuum-dried, dissolved in 220 g of tetrahydrofuran, and dropped into a mixed solution of 28% by mass ammonia aqueous solution 8.95 g, methanol 400 g, and ion-exchanged water 200 g for reprecipitation.
- the obtained colorless solid was dried to obtain 17.6 g of a polymer compound (4) having the following two repeating units [D].
- the polymer compound (4) had a weight average molecular weight Mw of 28,000 and a dispersity: Mw / Mn of 4.14 as measured by polystyrene conversion by GPC.
- the mixture was stirred at 70 ° C. for 8 hours and allowed to cool to room temperature.
- the reaction solution was diluted by adding 43 g of tetrahydrofuran, this solution was added dropwise to 930 g of methanol to perform reprecipitation, and the resulting pale yellow solid was collected by filtration. This was dissolved again in 140 g of tetrahydrofuran, and added dropwise to 900 g of methanol for reprecipitation.
- the obtained pale yellow solid was vacuum-dried at 40 ° C. for 6 hours to obtain 23.4 g of a polymer compound (5) having the following two repeating units [E].
- the polymer compound (5) had a weight average molecular weight Mw of 22,400 and a degree of dispersion: Mw / Mn of 3.18, as measured by GPC based on polystyrene.
- the temperature was raised to 85 ° C., and stirring was performed to initiate polymerization. After reacting for 3 hours, the solution was cooled to room temperature, and 60 g of tetrahydrofuran and 2.98 g (49.2 mmol) of 28 mass% aqueous ammonia solution were added and stirred. This reaction solution was added dropwise to 440 g of methanol to perform reprecipitation. The precipitated pale yellow solid was vacuum-dried, dissolved in 60 g of THF, and re-precipitated by adding dropwise to a mixed solution of 2.98 g of 28% by mass aqueous ammonia, 400 g of methanol, and 100 g of ion-exchanged water.
- This polymer compound (6) had a weight average molecular weight Mw measured in terms of polystyrene by GPC of 63,000, and a degree of dispersion: Mw / Mn was 9.34.
- Example 5 ⁇ Crack resistance of polymer compound having triarylamine structure>
- the polymer compound (1) obtained in Example 1 was dissolved in cyclohexanone so as to be 20% by mass, and 2,4-tolylene diisocyanate so as to be 10% by mass with respect to the polymer compound (1). [Tokyo Chemical Industry Co., Ltd.] was added. A film was formed on a glass substrate by a spin coating method, and was cured by heat treatment at 150 ° C. for 10 minutes. The film thickness of the obtained film was 2.39 ⁇ m. When observed under a microscope, it was confirmed that a uniform film without cracks was obtained.
- Example 6 The polymer compound (2) obtained in Example 2 was dissolved in cyclohexanone so as to be 20% by mass, and 2,4-tolylene diisocyanate so as to be 10% by mass with respect to the polymer compound (2). [Tokyo Chemical Industry Co., Ltd.] was added. A film was formed on a glass substrate by a spin coating method, and was cured by heat treatment at 150 ° C. for 10 minutes. The film thickness of the obtained film was 3.00 ⁇ m. When observed under a microscope, it was confirmed that a uniform film without cracks was obtained.
- Example 7 The polymer compound (3) obtained in Example 3 was dissolved in cyclohexanone so as to be 20% by mass. This solution was formed on a glass substrate by spin coating and dried at 150 ° C. for 10 minutes. The film thickness of the obtained film was 2.51 ⁇ m. When observed under a microscope, it was confirmed that a uniform film without cracks was obtained.
- Example 8 The polymer compound (4) obtained in Example 4 was dissolved in cyclohexanone so as to be 20% by mass. This solution was formed on a glass substrate by spin coating and dried at 150 ° C. for 10 minutes. The film thickness of the obtained film was 2.28 ⁇ m. When observed under a microscope, it was confirmed that a uniform film without cracks was obtained.
- Comparative Example 1 The polymer compound (5) obtained in Comparative Synthesis Example 1 was dissolved in propylene glycol monomethyl ether acetate so as to be 30% by mass. This solution was formed on a glass substrate by spin coating and dried at 150 ° C. for 10 minutes. The film thickness of the obtained film was 4.81 ⁇ m. When observed under a microscope, the occurrence of cracks was confirmed.
- Comparative Example 2 The polymer compound (6) obtained in Comparative Synthesis Example 2 was dissolved in cyclohexanone so as to be 20% by mass. This solution was formed on a glass substrate by spin coating and dried at 150 ° C. for 10 minutes. The film thickness obtained was 2.37 ⁇ m. When observed under a microscope, the occurrence of cracks was confirmed.
- Example 9 ⁇ Measurement of resistance value of clad material> 0.51 g of the polymer compound (1) having a triarylamine structure obtained in Example 1 and 0.06 g of a blocked isocyanate [manufactured by Asahi Kasei Chemicals Corporation, Duranate (registered trademark) MF-K60X] were added to cyclopentanone 2 0.03 g of the nonlinear optical compound synthesized in Synthesis Example 1 was mixed with the solution dissolved in .4 g and stirred.
- a blocked isocyanate manufactured by Asahi Kasei Chemicals Corporation, Duranate (registered trademark) MF-K60X
- This solution was filtered through a filter having a pore size of 0.20 ⁇ m, and then spin-coated on an ITO glass substrate (film thickness 150 nm, surface resistance 10 ⁇ / ⁇ : manufactured by Mitani Vacuum Industries, Ltd.). Thereafter, it was heated on a hot plate at 150 ° C. for 30 minutes, and dried and crosslinked. The obtained cured film had a thickness of 1.7 ⁇ m.
- gold was deposited as a top electrode with a thickness of 100 nm by a sputtering method to obtain a resistance measurement sample (1).
- Example 3 A sample for resistance value measurement (2) was prepared in the same manner as in Example 9 except that the nonlinear optical compound was not blended. The obtained cured film had a thickness of 1.7 ⁇ m.
- Example 10 Production of clad / core laminated film 0.51 g of polymer compound (1) having a triarylamine structure obtained in Example 1 and blocked isocyanate [Duranate (registered trademark) manufactured by Asahi Kasei Chemicals Corporation] MF-K60X] 0.06 g dissolved in cyclopentanone 2.4 g was mixed with 0.03 g of the nonlinear optical compound synthesized in Synthesis Example 1 and stirred. This solution was filtered through a filter having a pore size of 0.20 ⁇ m and spin-coated on an ITO glass substrate. Thereafter, it was heated on a hot plate at 150 ° C. for 30 minutes, dried and crosslinked to form a clad.
- the electro-optic constant in this clad / core laminated film is determined using a semiconductor laser having a wavelength of 1.31 ⁇ m as a light source.
- a semiconductor laser having a wavelength of 1.31 ⁇ m as a light source.
- r1 is an actual electro-optic constant obtained in the clad / core laminated structure
- r2 is a thickness of a clad containing a nonlinear optical compound and a polymer compound (1) having a triarylamine structure.
- ridge type optical waveguide device was manufactured by the manufacturing process shown in FIG. First, a 5 nm chromium layer and then a 100 nm gold layer were formed on the silicon substrate 1 by vacuum deposition to form the lower electrode 2 (FIG. 1: (a)). On the lower electrode 2, the lower clad 3 was formed using the material used for the clad formation in the above ⁇ Measurement of electro-optic constant>.
- Example 1 0.51 g of the polymer compound (1) having a triarylamine structure obtained in Example 1 and 0.06 g of blocked isocyanate [manufactured by Asahi Kasei Chemicals Corporation, Duranate (registered trademark) MF-K60X] were added to cyclopenta 0.03 g of the nonlinear optical compound synthesized in Synthesis Example 1 is mixed with the solution dissolved in 2.4 g of non-mixed material and stirred. This solution is filtered through a filter having a pore size of 0.20 ⁇ m, and then spin-coated on the lower electrode 2. did. Thereafter, the mixture was heated on a hot plate at 150 ° C.
- FIG. 1: (a) Photoresist 4 [manufactured by Nippon Zeon Co., Ltd., ZPN1150-90] is formed on the clad 3 (FIG. 1: (b)), and exposed and developed through a 4 ⁇ m-wide linear mask to develop a ridge-type lead. A waveguide pattern was formed (FIG. 1: (c)). Using this resist pattern as a mask, the pattern was transferred to the lower cladding 3 by reactive ion etching using CHF 3 gas. The height of the ridge (indicated by H in the figure) at this time was about 500 nm (FIG. 1: (d)).
- the core is formed on the upper part using the material used for forming the core in the above ⁇ Measurement of electro-optic constant>. 5 was formed. That is, a solution obtained by dissolving 0.45 g of the polymer having the repeating unit shown in [H] obtained in Synthesis Example 2 in 2.6 g of cyclopentanone was spin-coated, and dried at 80 ° C. under reduced pressure for 6 hours. The core 5 was produced (FIG. 1: (f)). Furthermore, the upper clad 6 was formed on the core 5 with the same material and method as the lower clad 3 (FIG.
- a photoresist solvent acetone / ethanol mixed solvent
- the shape of the produced optical waveguide 8 (core / cladding) is shown in FIG.
- the lower electrode 2 and the upper electrode 7 are omitted.
- D1, D2, and D3 indicate the thickness of the lower cladding, the thickness of the core, and the thickness of the upper cladding, respectively
- H indicates the height of the ridge portion
- W indicates the waveguide width.
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Abstract
Description
第2観点として、前記非線形光学化合物が、トリシアノ結合フラン環を有する化合物である、第1観点に記載のクラッド材料に関する。
第3観点として、前記トリシアノ結合フラン環を有する化合物が、下記式(1)で表される化合物である、第2観点に記載のクラッド材料に関する。
第4観点として、前記トリアリールアミン構造を含む高分子化合物が、式(2)又は式(3)で表される繰り返し単位を有する、第1観点に記載のクラッド材料に関する。
第5観点として、前記繰り返し単位が式(13)で表される、第4観点に記載のクラッド材料に関する。
第6観点として、前記Z1が、前記式(9)で表される一価の有機基であり、前記Z2が水素原子である、第5観点に記載のクラッド材料に関する。
第7観点として、コアと、その外周全体を取り囲む前記コアよりも屈折率の小さいクラッドからなる光導波路であって、前記クラッドが第1観点乃至第6観点のうち何れか一項に記載のクラッド材料より形成されてなる、光導波路に関する。
第8観点として、前記コアが、式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物又はその誘導体を含む、第7観点に記載の光導波路に関する。
第9観点として、コアと、前記コアの周囲を取り囲み前記コアより屈折率の小さいクラッドとを有する第8観点に記載の光導波路の製造方法であって、
下部クラッドを第1観点乃至第6観点のうち何れか一項に記載のクラッド材料を用いて形成する工程、
前記下部クラッド上に第8観点に記載の式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物又はその誘導体を含むコアを形成する工程、及び、
前記コア上に第1観点乃至第6観点のうち何れか一項に記載のクラッド材料を用いて上部クラッドを形成する工程を含み、
上部クラッドを形成する工程の前及び/又は後に、前記コアに含まれる非線形光学化合物又はその誘導体を分極配向処理する工程を含む、
該光導波路を製造する方法に関する。
第10観点として、コアと、前記コアの周囲を取り囲み前記コアより屈折率の小さいクラッドとを有する第8観点に記載の光導波路の製造方法であって、
下部クラッドを第1観点乃至第6観点のうち何れか一項に記載のクラッド材料を用いて形成する工程、
前記下部クラッド上に、紫外線に対し感光性を有するレジスト層を形成し、前記レジスト層の表面に、フォトマスクを介して紫外光を照射・現像して、コアのマスクパターンを形成し、該マスクパターンをマスクとして前記下部クラッドにコアパターンを転写し、レジスト層を除去する工程、
下部クラッド上に第8観点に記載の式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物又はその誘導体を含むコアを形成する工程、及び、
前記コア上に第1観点乃至第6観点のうち何れか一項に記載のクラッド材料を用いて上部クラッドを形成する工程を含み、
上部クラッドを形成する工程の前及び/又は後に、前記コアに含まれる非線形光学化合物又はその誘導体を分極配向処理する工程を含む、
リッジ型光導波路を製造する方法に関する。
第11観点として、前記分極配向処理が、電極による電界印加処理であることを特徴とする、第9観点又は第10観点に記載の製造方法に関する。
第12観点として、式(2)又は式(3)で表される繰り返し単位を有する高分子化合物に関する。
第13観点として、前記繰り返し単位が式(13)で表される、第12観点に記載の高分子化合物に関する。
第14観点として、前記Z1が、前記式(9)で表される一価の有機基であり、前記Z2が水素原子である、第13観点に記載の高分子化合物に関する。
以下、本発明についてさらに詳しく説明する。
<トリアリールアミン構造を含む高分子化合物>
本発明において用いられる、トリアリールアミン構造を含む高分子化合物は特に限定されるものではないが、好ましくはトリアリールアミン骨格を分岐点として含有する下記式(2)又は式(3)で表される繰り返し単位を有する高分子化合物である。
ここで炭素原子数1~5のアルキル基としては、分岐構造、環状構造を有していても良く、メチル基、エチル基、n-プロピル基、イソプロピル基、シクロプロピル基、n-ブチル基、イソブチル基、sec-ブチル基、tert-ブチル基、n-ペンチル基、ネオペンチル基、シクロペンチル基等が挙げられる。
炭素原子数1~5のアルコキシ基としては、分岐構造、環状構造を有していても良く、メトキシ基、エトキシ基、n-プロポキシ基、イソプロポキシ基、シクロプロポキシ基、n-ブトキシ基、イソブトキシ基、sec-ブトキシ基、tert-ブトキシ基、n-ペンチルオキシ基、ネオペンチルオキシ基、シクロペンチルオキシ基等が挙げられる。
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。
ここで炭素原子数1~5のアルキル基としては、前記R19~R52にて挙げたものと同じものが挙げられる。
ここで炭素原子数1~5のアルキル基としては、前記R19~R52にて挙げたものと同じものが挙げられる。
炭素原子数1~5のヒドロキシアルキル基としては、分岐構造、環状構造を有していても良く、ヒドロキシメチル基、2-ヒドロキシエチル基、2-ヒドロキシプロピル基、1-ヒドロキシプロパン-2-イル基、2-ヒドロキシシクロプロピル基、4-ヒドロキシブチル基、5-ヒドロキシペンチル基、1-ヒドロキシシクロペンチル基等が挙げられる。
炭素原子数1~5のハロアルキル基としては、分岐構造、環状構造を有していても良く、フルオロメチル基、トリフルオロメチル基、ブロモジフルオロメチル基、2-クロロエチル基、2-ブロモエチル基、1,1-ジフルオロエチル基、2,2,2-トリフルオロエチル基、1,1,2,2,-テトラフルオロエチル基、2-クロロ-1,1,2-トリフルオロエチル基、ペンタフルオロエチル基、3-ブロモプロピル基、2,2,3,3-テトラフルオロプロピル基、1,1,2,3,3,3-ヘキサフルオロプロピル基、1,1,1,3,3,3-ヘキサフルオロプロパン-2-イル基、3-ブロモ-2-メチルプロピル基、2,2,3,3-テトラフルオロシクロプロピル基、4-ブロモブチル基、パーフルオロペンチル基、パーフルオロシクロペンチル基等が挙げられる。
ハロゲン原子としては、前記R19~R52にて挙げたものと同じものが挙げられる。
ここで炭素原子数1~5のアルキル基、炭素原子数1~5のアルコキシ基、及びハロゲン原子としては、前記R19~R52にて挙げたものと同じものが挙げられる。
炭素原子数1~5のヒドロキシアルキル基としては、前記R53~R76にて挙げたものと同じものが挙げられる。
具体的には、本発明の対象とする高分子化合物は、前記式(2)又は式(3)で表される繰り返し単位を有する高分子化合物であって、該高分子化合物は、式(2)及び式(3)中、Ar2~Ar4は、それぞれ独立して、前記式(4)~(8)で表される何れかの二価の有機基(式(4)~(8)中、R19~R52は、それぞれ独立して、水素原子、炭素原子数1~5のアルキル基、エポキシ基、カルボキシル基、ヒドロキシ基、炭素原子数1~5のアルコキシ基、又はハロゲン原子を表す。)を表し;式(2)中、Z1及びZ2は、それぞれ独立して、水素原子、炭素原子数1~5のアルキル基、又は前記式(9)~(12)で表される何れかの一価の有機基(式(9)~(12)中、R53~R76は、それぞれ独立して、水素原子(ただし、R53~R57、R58~R64、R65~R67、又はR68~R76が同時に水素原子となることはない。)、又は炭素原子数1~5のヒドロキシアルキル基、OR77、COR77、COOR77、又はNR77R78基(これらの式中、R77及びR78は、それぞれ独立して、水素原子(ただし、R77及びR78が同時に水素原子となることはない。)、又は炭素原子数1~5のヒドロキシアルキル基を表す。)を表す。)を表し(ただし、Z1及びZ2が同時に前記アルキル基となることはない。);式(3)中、R15~R18は、それぞれ独立して、水素原子(ただし、R15~R18が同時に水素原子となることはない。)、又は炭素原子数1~5のヒドロキシアルキル基を表すものである。
ここで、各基の具体例は前述したものが挙げられる。
尚、本発明における重量平均分子量とは、ゲル浸透クロマトグラフィー(ポリスチレン換算)による測定値である。
上記高分子化合物は、トリアリールアミン化合物と、アルデヒド化合物とを、酸性条件下で重縮合することによって得られる。
酸触媒の使用量は、その種類によって種々選択されるが、通常、トリアリールアミン化合物100質量部に対して、0.001~10,000質量部、好ましくは、0.01~1,000質量部、より好ましくは、0.1~100質量部である。
以上のようにして得られる高分子化合物の重量平均分子量は、前述のとおり、通常1,000~2,000,000、好ましくは2,000~1,000,000である。
本発明に用いられる非線形光学化合物は、π共役鎖の一方の端に電子供与性基、他方の端に電子吸引性基を有するπ共役系化合物であり、分子超分極率βの大きいものが望ましい。電子供与性基としてはジアルキルアミノ基、電子吸引性基としては、シアノ基、ニトロ基、フルオロアルキル基を挙げることができる。
中でも、本発明において用いられる非線形光学化合物としては、トリシアノ結合フラン環を有する非線形光学化合物が挙げられ、具体的には下記式(1)で表される化合物であることが好ましい。
ここで炭素原子数1~10のアルキル基としては、分岐構造、環状構造を有していても良く、メチル基、エチル基、n-プロピル基、イソプロピル基、シクロプロピル基、n-ブチル基、イソブチル基、sec-ブチル基、tert-ブチル基、n-ペンチル基、ネオペンチル基、シクロペンチル基、n-ヘキシル基、シクロヘキシル基、n-オクチル基、n-デシル基、1-アダマンチル基、ベンジル基、フェネチル基等が挙げられる。
炭素原子数6~10のアリール基としては、フェニル基、トリル基、キシリル基、ナフチル基等が挙げられる。
上記置換基としては、アミノ基;ヒドロキシ基;メトキシカルボニル基、tert-ブトキシカルボニル基等のアルコキシカルボニル基;トリメチルシリルオキシ基、tert-ブチルジメチルシリルオキシ基、tert-ブチルジフェニルシリルオキシ基、トリフェニルシリルオキシ基等のシリルオキシ基;ハロゲン原子などが挙げられる。
ここで炭素原子数1~10のアルキル基としては、前記と同じものが挙げられる。
炭素原子数1~10のアルコキシ基としては、分岐構造、環状構造を有していても良く、メトキシ基、エトキシ基、n-プロポキシ基、イソプロポキシ基、シクロプロポキシ基、n-ブトキシ基、イソブトキシ基、sec-ブトキシ基、tert-ブトキシ基、n-ペンチルオキシ基、ネオペンチルオキシ基、シクロペンチルオキシ基、n-ヘキシルオキシ基、シクロヘキシルオキシ基、n-オクチルオキシ基、n-デシルオキシ基、1-アダマンチルオキシ基、ベンジルオキシ基、フェネトキシ基等が挙げられる。
炭素原子数2~11のアルキルカルボニルオキシ基としては、分岐構造、環状構造を有していても良く、アセトキシ基、プロピオニルオキシ基、ブチリルオキシ基、イソブチリルオキシ基、シクロプロパンカルボニルオキシ基、ペンタノイルオキシ基、2-メチルブタノイルオキシ基、3-メチルブタノイルオキシ基、ピバロイルオキシ基、ヘキサノイルオキシ基、3,3-ジメチルブタノイルオキシ基、シクロペンタンカルボニルオキシ基、ヘプタノイルオキシ基、シクロヘキサンカルボニルオキシ基、n-ノナノイルオキシ基、n-ウンデカノイルオキシ基、1-アダマンタンカルボニルオキシ基、フェニルアセトキシ基、3-フェニルプロパノイルオキシ基等が挙げられる。
炭素原子数6~10のアリールオキシ基としては、フェノキシ基、ナフタレン-2-イルオキシ基、フラン-3-イルオキシ基、チオフェン-2-イルオキシ基等が挙げられる。
炭素原子数7~11のアリールカルボニルオキシ基としては、ベンゾイルオキシ基、1-ナフトイルオキシ基、フラン-2-カルボニルオキシ基、チオフェン-3-カルボニルオキシ基等が挙げられる。
炭素原子数1~6のアルキル基及び/又はフェニル基を有するシリルオキシ基としては、トリメチルシリルオキシ基、tert-ブチルジメチルシリルオキシ基、tert-ブチルジフェニルシリルオキシ基、トリフェニルシリルオキシ基等のシリルオキシ基が挙げられる。
ハロゲン原子としては、前記R19~R52にて挙げたものと同じものが挙げられる。
ここで炭素原子数1~5のアルキル基としては、前記R19~R52にて挙げたものと同じものが挙げられる。
炭素原子数1~5のハロアルキル基としては、前記R53~R76にて挙げたものと同じものが挙げられる。
炭素原子数6~10のアリール基としては、前記R1、R2にて挙げたものと同じものが挙げられる。
またR7、R8の具体的な組合せとしては、メチル基-メチル基、メチル基-トリフルオロメチル基、トリフルオロメチル基-フェニル基が好ましい。
なお、炭素原子数1~10のアルキル基、炭素原子数6~10のアリール基、並びに置換基の具体例は上記に例示したものが挙げられる。
本発明のクラッド材料において、トリアリールアミン構造を含む高分子化合物と非線形光学化合物との配合割合は、後述のコアの抵抗値よりも低い抵抗値となるように適宜調整されるが、通常、高分子化合物100質量部に対して、非線形光学化合物の配合量は0.1~50質量部であり、より好ましくは0.5~10質量部である。
本発明のクラッド材料には、光導波路のクラッド材料としての性能に影響を及ばさない範囲において、架橋剤、界面活性剤、レベリング剤、酸化防止剤、光安定化剤等を配合することができる。
汎用のイソシアネート類としては、例えば、コロネート(登録商標)2507、同2513、同APステープル(以上、日本ポリウレタン工業(株)製)、タケネート(登録商標)B-882N、同B-830、同B-815N、同B-842N、同B-846N、同B-870N、同B-874N(以上、三井化学(株)製)、バーノック(登録商標)D-500、同D-550、同B3-867(以上、DIC(株)製)、デュラネート(登録商標)MF-B60X、同MF-K60X(以上、旭化成ケミカルズ(株)製)、エラストロン(登録商標)BN-P17、同BN-04、同BN-08、同BN-44、同BN-45(以上、第一工業製薬(株)製)等が挙げられる。
これら架橋剤は、単独で用いても、2種以上を組合わせて用いても良い。
本発明の光導波路は、コアと、その外周全体を取り囲む前記コアよりも屈折率の小さいクラッドからなる光導波路であって、前記クラッドが前述のトリアリールアミン構造を含む高分子化合物と非線形光学化合物とを含有するクラッド材料より形成されてなることを特徴とするものである。
本発明の光導波路において、コアは、形成したクラッドの屈折率よりも大きな屈折率を有する材料で形成されていれば良い。
例えばコアは、二次の非線形光学効果を示す有機非線形光学化合物が、高分子マトリクス中に分散した形態で含まれてなるか、或いは高分子化合物の側鎖に結合した形態で含むものであることが好ましい。
上記有機非線形光学化合物としては、例えば前記式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物であることが好ましい。
こうした高分子マトリクス材料としては、例えば、ポリメタクリル酸メチル、ポリカーボネート、ポリスチレン、シリコーン系樹脂、エポキシ系樹脂、ポリスルホン、ポリエーテルスルホン、ポリイミド等の樹脂が挙げられる。
高分子マトリクス中に分散させる手法としては、非線形光学化合物とマトリクス材料を適切な比率で有機溶媒等に溶解させ、基板上に塗布・乾燥して薄膜を形成する方法が挙げられる。
これらの官能基は、上記前記式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物のヒドロキシ基等と共有結合を形成することが出来る。
なお、高分子化合物の側鎖に非線形光学化合物を結合させる場合、非線形光学化合物の含有量を調整するために、コアは、前述の高分子マトリクスの単位構造と、非線形高分子化合物を結合させた高分子化合物の単位構造とがいわば共重合してなる形態にあって良い。
本発明の光導波路は、
下部クラッドを前述のクラッド材料を用いて形成する工程、
前記下部クラッド上に前記式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物又はその誘導体を含むコアを形成する工程、及び、
前記コア上に前述のクラッド材料を用いて上部クラッドを形成する工程を含み、
上部クラッドを形成する工程の前及び/又は後に、前記コアに含まれる非線形光学化合物又はその誘導体を分極配向処理する工程を含みて、製造される。
(1)下部クラッドを前記クラッド材料を用いて形成する工程、
(2)前記下部クラッド上に、紫外線に対し感光性を有するレジスト層を形成し、前記レジスト層の表面に、フォトマスクを介して紫外光を照射・現像して、コアパターンを形成し、該コアパターンをマスクとして前記下部クラッドにコアパターンを転写し、レジスト層を除去する工程、
(3)下部クラッド上に前記式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物又はその誘導体を含むコアを形成する工程、及び、
(4)前記コア上に前記クラッド材料を用いて上部クラッドを形成する工程。
そして、(4)工程の前及び/又は後に、下記(5)工程を含む。
(5)前記コアに含まれる非線形光学化合物又はその誘導体を分極配向処理する工程。
以下、光導波路の製造方法について、詳述する。
まず前記クラッド材料を用いて、下部クラッドとなる薄膜を形成する。
具体的には、前述のクラッド材料を適宜有機溶媒に溶解又は分散させてワニス(膜形成材料)の形態とし、これをスピンコート法、ブレードコート法、ディップコート法、ロールコート法、バーコート法、ダイコート法、インクジェット法、印刷法(凸版、凸版、平板、スクリーン印刷等)等の塗布方法を用いて適当な基板上に塗布・乾燥する方法が挙げられる。上記塗布方法の中でもスピンコート法が好ましい。スピンコート法を用いる場合には、単時間で塗布することができるために、揮発性の高い溶液であっても利用でき、また、均一性の高い塗布を行うことができるという利点がある。
溶媒の乾燥法としては、特に限定されるものではなく、例えば、ホットプレートやオーブンを用いて、適切な雰囲気下、すなわち大気、窒素等の不活性ガス、真空中等で蒸発させれば良い。これにより、均一な成膜面を有する薄膜を得ることが可能である。乾燥温度は、溶媒を蒸発させることができれば特に限定されないが、40~250℃で行うことが好ましい。
このような有機溶媒の具体例としては、トルエン、p-キシレン、o-キシレン、m-キシレン、エチルベンゼン、スチレン等の芳香族炭化水素類;n-ヘキサン、n-ヘプタン等の脂肪族炭化水素類;クロロベンゼン、オルトジクロロベンゼン、クロロホルム、ジクロロメタン、ジブロモメタン、1,2-ジクロロエタン等のハロゲン化炭化水素類;アセトン、エチルメチルケトン、イソプロピルメチルケトン、イソブチルメチルケトン、ブチルメチルケトン、ジアセトンアルコール、ジエチルケトン、シクロペンタノン、シクロヘキサノン等のケトン類;酢酸エチル、酢酸プロピル、酢酸イソプロピル、酢酸ブチル、酢酸イソブチル、乳酸エチル、γ-ブチロラクトン等のエステル類;N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチル-2-ピロリドン、N-シクロヘキシル-2-ピロリドン等のアミド類;メタノール、エタノール、プロパノール、イソプロパノール、アリルアルコール、ブタノール、イソブタノール、tert-ブタノール、ペンタノール、2-メチルブタノール、2-メチル-2-ブタノール、シクロヘキサノール、2-メチルペンタノール、オクタノール、2-エチルヘキサノール、ベンジルアルコール、フルフリルアルコール、テトラヒドロフルフリルアルコール等のアルコール類;エチレングリコール、プロピレングリコール、ヘキシレングリコール、トリメチレングリコール、ジエチレングリコール、1,3-ブタンジオール、1,4-ブタンジオール、2,3-ブタンジオール等のグリコール類;ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン、1,4-ジオキサン、エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、トリエチレングリコールジメチルエーテル等のエーテル類;エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノイソプロピルエーテル、エチレングリコ-ルモノブチルエーテル、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテルアセテート、ブチレングリコールモノメチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノエチルエーテルアセテート、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル等のグリコールエーテル類;1,3-ジメチル-2-イミダゾリジノン;ジメチルスルホキシドなどが挙げられる。これらの有機溶媒は、単独で用いても、2種以上を組合わせて用いても良い。
次に、下部クラッド上に、紫外線に対し感光性を有するレジスト層を形成し、前記レジスト層の表面に、フォトマスクを介して紫外光を照射・現像するフォトリソグラフィー法によって、コアのマスクパターンを形成する。
ここでレジスト層としては、上記フォトリソグラフィー法によって微小パターンが感光・現像できる材料で、該工程で使用する溶媒が前記下部クラッドを溶出しない材料であれば特に限定されないが、ポジ型又はネガ型のフォトレジスト材料が好ましい。パターン形成の光源には、水銀ランプ、KrFレーザ、ArFレーザ等が用いられる。
次に、レジスト層のコアのマスクパターンをマスクとして、ガスを用いたドライエッチングをすることにより、下部クラッドにコアパターンを転写する。このドライエッチングには、レジストと下部クラッドのエッチング特性から適宜選択されるガス種、通常、CHF3、O2、Ar、CF4等を用いた反応性イオンエッチングが好ましく用いられる。
ドライエッチング後、マスクに用いたレジスト層を溶媒により除去する。
次に、コアパターンを形成した下部クラッド上に、前記式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物又はその誘導体を含むコアを形成する。
具体的には、前述の<コア>において説明したように、前記式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物と高分子マトリクス材料を、適切な比率で適当な有機溶媒に溶解させてワニスの形態とし、基板上に塗布・乾燥して薄膜を形成する方法、或いは、上記前記式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物の誘導体を側鎖に有する高分子化合物を適当な有機溶媒に溶解させてワニスの形態とし、基板上に塗布・乾燥して薄膜を形成する方法が挙げられる。
上記ワニスの塗布方法や乾燥条件、有機溶媒は前述の<(1)下部クラッドを形成する工程>で挙げたものを使用可能である。
なお、コア形成時に下部クラッドを溶出させないように、有機溶媒は下部クラッドを溶解しないものを選択する。
そして前記クラッド材料を用いて、<(1)下部クラッドを形成する工程>と同様に上部クラッドとなる薄膜を形成する。
上部クラッドを形成する前及び/又は後に、コアに含まれる非線形光学化合物に対して電界を印加する電界ポーリング法によって、分極配向処理を行う。分極配向処理は、コアのガラス転移温度付近又はそれ以上の温度において行われ、電界印加によって非線形光学化合物の分極を電界印加方向に配向させ、温度を常温に戻した後もその配向を保持することによって、コア及び光導波路に電気光学特性を付与することができる。
電界印加には、積層構造上下に配した電極間への直流電圧印加方法や、コア表面へのコロナ放電を利用した方法が用いられるが、配向処理の簡便さや均一性から、電極による電界印加処理が好ましい。
(1)GPC(ゲル浸透クロマトグラフィー)
装置:東ソー(株)製 HLC-8220GPC
カラム:昭和電工(株)製 KF-804L + KF-805L
カラム温度:40℃
溶媒:テトラヒドロフラン(THF)
検出器:RI
(2)1H NMRスペクトル
装置:日本電子(株)製 JNM-ECA700
溶媒:CDCl3
内部標準:テトラメチルシラン
(3)示差走査熱量計
装置:NETZSCH製 DSC 204F1 Phoenix(登録商標)
昇温速度:30℃/分
測定温度:25~300℃
(4)スピンコーター
装置:ミカサ(株)製 MS-A100
(5)ホットプレート
装置:アズワン(株)製 ND-2
(6)屈折率
装置:ジェー・エー・ウーラム・ジャパン製 多入射角分光エリプソメーターVASE
(7)抵抗率
電源装置:(株)エヌエフ回路設計ブロック製 HSA4052
測定装置:(株)エーディーシー製 8340A型デジタル超高抵抗/微小電流計
窒素雰囲気にて100mL反応フラスコにトリフェニルアミン[東京化成工業(株)製]8.52g(34.7mmol)、4-(2-ヒドロキシエトキシ)ベンズアルデヒド[東京化成工業(株)製]11.54g(69.5mmol)、p-トルエンスルホン酸一水和物[純正化学(株)製]1.32g(6.95mmol)を仕込み、1,4-ジオキサン20gを加えて溶解させた。85℃に昇温し、撹拌を行って重合を開始した。5時間30分間反応を行った後、溶液を室温まで冷却し、テトラヒドロフラン60g、28質量%アンモニア水溶液4.72g(77.7mmol)を加えて撹拌を行った。この反応液をメタノール500gに滴下して再沈殿を行った。析出した淡黄色固体を真空乾燥したのち、テトラヒドロフラン67gに溶解し、28質量%アンモニア水溶液4.72g、メタノール450g、及びイオン交換水50gの混合液に滴下して再沈殿を行った。得られた無色固体を乾燥して、下記[A]の繰り返し単位を有する高分子化合物(1)6.88gを得た。この高分子化合物(1)のGPCによるポリスチレン換算で測定される重量平均分子量Mwは32,800、分散度:Mw(重量平均分子量)/Mn(数平均分子量)は3.70であった。
窒素雰囲気にて100mL反応フラスコにトリフェニルアミン[東京化成工業(株)製]10.0g(40.8mmol)、3-(2-ヒドロキシエトキシ)ベンズアルデヒド[東京化成工業(株)製]13.6g(81.5mmol)、p-トルエンスルホン酸一水和物[純正化学(株)製]0.78g(4.08mmol)を仕込み、1,4-ジオキサン24gを加えて溶解させた。85℃に昇温し、撹拌を行って重合を開始した。3時間30分間反応を行った後、溶液を室温まで冷却し、テトラヒドロフラン70g、28質量%アンモニア水溶液9.90g(163mmol)を加えて撹拌を行った。この反応液をメタノール510gに滴下して再沈殿を行った。析出した淡黄色固体を真空乾燥したのち、テトラヒドロフラン60gに溶解し、28質量%アンモニア水溶液9.90g、メタノール450g、及びイオン交換水50gの混合液に滴下して再沈殿を行った。得られた無色固体を乾燥して、下記[B]の繰り返し単位を有する高分子化合物(2)7.90gを得た。この高分子化合物(2)のGPCによるポリスチレン換算で測定される重量平均分子量Mwは17,000、分散度:Mw/Mnは2.54であった。
窒素雰囲気にて100mL反応フラスコにジフェニルメチルアミン[東京化成工業(株)製]3.00g(16.4mmol)、トリフェニルアミン[東京化成工業(株)製]2.01g(8.19mmol)、4-(2-ヒドロキシエトキシ)ベンズアルデヒド[東京化成工業(株)製]8.16g(49.11mmol)、p-トルエンスルホン酸一水和物[純正化学(株)製]0.47g(2.46mmol)を仕込み、1,4-ジオキサン13gを加えて溶解させた。85℃に昇温し、撹拌を行って重合を開始した。3時間30分間反応を行った後、溶液を室温まで冷却し、テトラヒドロフラン63g、28質量%アンモニア水溶液1.49g(24.5mmol)を加えて撹拌を行った。この反応液をメタノール400gに滴下して再沈殿を行った。析出した淡黄色固体を真空乾燥したのち、テトラヒドロフラン63gに溶解し、28質量%アンモニア水溶液1.49g、メタノール400g、及びイオン交換水100gの混合液に滴下して再沈殿を行った。得られた無色固体を乾燥して、下記[C]の2種の繰り返し単位を有する高分子化合物(3)5.58gを得た。この高分子化合物(3)のGPCによるポリスチレン換算で測定される重量平均分子量Mwは12,600、分散度:Mw/Mnは2.10であった。
窒素雰囲気にて100mL反応フラスコにジフェニルメチルアミン[東京化成工業(株)製]9.00g(49.1mmol)、トリフェニルアミン[東京化成工業(株)製]6.02g(24.6mmol)、3-(2-ヒドロキシエトキシ)ベンズアルデヒド[東京化成工業(株)製]24.5g(147mmol)、p-トルエンスルホン酸一水和物[純正化学(株)製]1.40g(7.37mmol)を仕込み、1,4-ジオキサン39.5gを加えて溶解させた。85℃に昇温し、撹拌を行って重合を開始した。70分間反応を行った後、溶液を室温まで冷却し、テトラヒドロフラン120g、28質量%アンモニア水溶液8.95g(147mmol)を加えて撹拌を行った。この反応液をメタノール560gに滴下して再沈殿を行った。析出した淡黄色固体を真空乾燥したのち、テトラヒドロフラン220gに溶解し、28質量%アンモニア水溶液8.95g、メタノール400g、及びイオン交換水200gの混合液に滴下して再沈殿を行った。得られた無色固体を乾燥して、下記[D]の2種の繰り返し単位を有する高分子化合物(4)17.6gを得た。この高分子化合物(4)のGPCによるポリスチレン換算で測定される重量平均分子量Mwは28,000、分散度:Mw/Mnは4.14であった。
還流塔を付した300mLの反応フラスコに、ビニルナフタレン[新日鐵化学(株)製]37.0g(0.240mol)、メタクリル酸グリシジル[東京化成工業(株)製]8.53g(0.060mol)を入れ、ジメチルアセトアミド68gを加えて溶解させた。これに2,2’-アゾビスイソ絡酸ジメチル[和光純薬工業(株)製]1.11g(4.80 mmol)を加え、フラスコ内を窒素置換した。70℃にて8時間撹拌を行い、室温まで放冷した。反応溶液にテトラヒドロフラン43gを加えて希釈し、この溶液をメタノール930gに滴下して再沈殿を行い、得られた淡黄色固体を濾過により回収した。これをテトラヒドロフラン140gに再度溶解し、メタノール900gに滴下して再沈殿を行った。得られた淡黄色固体を40℃にて6時間真空乾燥して、下記[E]の2種の繰り返し単位を有する高分子化合物(5)23.4gを得た。この高分子化合物(5)のGPCによるポリスチレン換算で測定される重量平均分子量Mwは22,400、分散度:Mw/Mnは3.18であった。
窒素雰囲気にて50mL反応フラスコにジフェニルメチルアミン[東京化成工業(株)製]2.00g(10.9mmol)、トリフェニルアミン[東京化成工業(株)製]1.34g(5.46mmol)、ベンズアルデヒド[東京化成工業(株)製]3.47g(32.7mmol)、p-トルエンスルホン酸一水和物[純正化学(株)製]0.31g(1.64mmol)を仕込み、1,4-ジオキサン7gを加えて溶解させた。85℃に昇温し、撹拌を行って重合を開始した。3時間反応を行った後、溶液を室温まで冷却し、テトラヒドロフラン60g、28質量%アンモニア水溶液2.98g(49.2mmol)を加えて撹拌を行った。この反応液をメタノール440gに滴下して再沈殿を行った。析出した淡黄色固体を真空乾燥したのち、THF60gに溶解し、28質量%アンモニア水溶液2.98g、メタノール400g、及びイオン交換水100gの混合液に滴下して再沈殿を行った。得られた無色固体を乾燥して、下記[F]の2種の繰り返し単位を有する高分子化合物(6)2.96gを得た。この高分子化合物(6)のGPCによるポリスチレン換算で測定される重量平均分子量Mwは63,000、分散度:Mw/Mnは9.34であった。
トリシアノ結合フラン環を有する非線形光学化合物として、下記[G]に示す化合物を用いた。本化合物は、X.Zhangら、Tetrahedron.lett.,51,p5823(2010)に開示される方法に準じて合成した。
[実施例5]
実施例1で得られた高分子化合物(1)を、20質量%となるようにシクロヘキサノンに溶解し、高分子化合物(1)に対して10質量%となるように2,4-トリレンジイソシアネート[東京化成工業(株)製]を加えた。スピンコート法によりガラス基板に成膜し、150℃で10分間熱処理を行い硬化させた。得られた膜の膜厚は2.39μmであった。顕微鏡観察を行ったところ、クラックのない均一な膜が得られたことが確認された。
実施例2で得られた高分子化合物(2)を、20質量%となるようにシクロヘキサノンに溶解し、高分子化合物(2)に対して10質量%となるように2,4-トリレンジイソシアネート[東京化成工業(株)製]を加えた。スピンコート法によりガラス基板に成膜し、150℃で10分間熱処理を行い硬化させた。得られた膜の膜厚は3.00μmであった。顕微鏡観察を行ったところ、クラックのない均一な膜が得られたことが確認された。
実施例3で得られた高分子化合物(3)を、20質量%となるようにシクロヘキサノンに溶解させた。この溶液をガラス基板上にスピンコート法により成膜し、150℃で10分間乾燥した。得られた膜の膜厚は2.51μmであった。顕微鏡観察を行ったところ、クラックのない均一な膜が得られたことが確認された。
実施例4で得られた高分子化合物(4)を、20質量%となるようにシクロヘキサノンに溶解させた。この溶液をガラス基板上にスピンコート法により成膜し、150℃で10分間乾燥した。得られた膜の膜厚は2.28μmであった。顕微鏡観察を行ったところ、クラックのない均一な膜が得られたことが確認された。
比較合成例1で得られた高分子化合物(5)を、30質量%となるようにプロピレングリコールモノメチルエーテルアセテートに溶解させた。この溶液をガラス基板上にスピンコート法により成膜し、150℃で10分間乾燥した。得られた膜の膜厚は4.81μmであった。顕微鏡観察を行ったところ、クラックの発生が確認された。
比較合成例2で得られた高分子化合物(6)を、20質量%となるようにシクロヘキサノンに溶解させた。この溶液をガラス基板上にスピンコート法により成膜し、150℃で10分間乾燥した。得られた膜の膜厚は2.37μmであった。顕微鏡観察を行ったところ、クラックの発生が確認された。
高分子化合物(1)~(6)を10質量%となるようにシクロヘキサノンに溶解させた。この溶液をシリコン基板上にスピンコート法により成膜し、150℃で10分間乾燥した。得られた膜の633nmにおける屈折率を、分光エリプソメトリーにより測定した。得られた結果を表1に示す。
[実施例9]
実施例1で得られたトリアリールアミン構造を有する高分子化合物(1)0.51g及びブロックイソシアネート[旭化成ケミカルズ(株)製、デュラネート(登録商標)MF-K60X]0.06gをシクロペンタノン2.4gに溶解させた溶液に、合成例1で合成した非線形光学化合物0.03gを混合して撹拌した。この溶液を孔径0.20μmのフィルタで濾過後、ITOガラス基板(膜厚150nm、表面抵抗10Ω/□:三谷真空工業(株)製)上にスピンコートした。その後150℃のホットプレートで30分間加熱し、乾燥及び架橋を行った。得られた硬化膜の膜厚は1.7μmであった。この上に金をスパッタリング法により100nmの厚さで上部電極として成膜し、抵抗値測定用サンプル(1)とした。
非線形光学化合物を配合しなかった以外は実施例9と同様に操作し、抵抗値測定用サンプル(2)を併せて作製した。得られた硬化膜の膜厚は1.7μmであった。
表2に示すように、非線形光学化合物の添加により20℃及び130℃双方で抵抗率が大きく低下した。
クラッドの抵抗率の低下によるコアの電界配向処理への効果確認のため、クラッド上に電気光学特性を有するコアを積層して電界配向処理を施し、電気光学定数の測定を行った。
コアには、高分子化合物側鎖にトリシアノ結合フラン環を有する非線形光学化合物が結合した、下記[H]に示す繰り返し単位を有するポリマーを用いた。本ポリマーは、X.Piaoら、J.Polym.Sci.A,49,p47(2011)に開示される方法に準じて合成した。得られたポリマーのUV-Visスペクトルから求めたポリマー中の非線形光学化合物(下記[H]中のR部分)の割合は、40質量%であった。
実施例1で得られたトリアリールアミン構造を有する高分子化合物(1)0.51g及びブロックイソシアネート[旭化成ケミカルズ(株)製、デュラネート(登録商標)MF-K60X]0.06gをシクロペンタノン2.4gに溶解させた溶液に、合成例1で合成した非線形光学化合物0.03gを混合して撹拌した。この溶液を孔径0.20μmのフィルタで濾過後、ITOガラス基板にスピンコートした。その後150℃のホットプレートで30分間加熱し、乾燥及び架橋を行い、クラッドとした。
この上に、合成例2で得られた上記[H]に示す繰り返し単位を有するポリマー0.45gを、シクロペンタノン2.6gに溶解させた溶液をスピンコートし、減圧下、80℃で6時間乾燥させ、コアを作製した。
さらにコア上に、金をスパッタリング法により100nmの厚さで上部電極として成膜した。
今回用いた上記[H]に示す繰り返し単位を有するポリマーは、単体で100pm/Vの電気光学定数を示すため、表3に示す結果(r2=94pm/V)より、非線形光学化合物を導入したクラッドを用いることにより、積層構造においてもコアに効率的に電圧が印加されていることがわかる。
図1に示す作製プロセスによりリッジ型光導波路素子を作製した。
まずシリコン基板1上に5nmのクロム層、ひきつづき100nmの金層を真空蒸着により成膜し下部電極2とした(図1:(a))。
下部電極2上に、前記<電気光学定数の測定>にてクラッドの形成に用いた材料を用いて下部クラッド3を形成した。すなわち、実施例1で得られたトリアリールアミン構造を有する高分子化合物(1)0.51g及びブロックイソシアネート[旭化成ケミカルズ(株)製、デュラネート(登録商標)MF-K60X]0.06gをシクロペンタノン2.4gに溶解させた溶液に、合成例1で合成した非線形光学化合物0.03gを混合して撹拌し、この溶液を孔径0.20μmのフィルタで濾過後、下部電極2上にスピンコートした。その後150℃のホットプレートで30分間加熱し、乾燥及び架橋を行い、下部クラッド3を作製した(図1:(a))。
クラッド3の上にフォトレジスト4[日本ゼオン(株)製、ZPN1150-90]を成膜し(図1:(b))、4μm幅の直線状マスクを通し露光、現像することでリッジ型導波路パターンを形成した(図1:(c))。
このレジストパターンをマスクとして、CHF3ガスによる反応性イオンエッチングにより、下部クラッド3にパターンを転写した。このときのリッジ(図中、Hで表示)の高さは500nm程度とした(図1:(d))。
フォトレジストをフォトレジスト溶媒(アセトン/エタノール混合溶媒)にて除去後(図1:(e))、この上部に前記<電気光学定数の測定>にてコアの形成に用いた材料を用いてコア5を形成した。すなわち、合成例2で得られた上記[H]に示す繰り返し単位を有するポリマー0.45gをシクロペンタノン2.6gに溶解させた溶液をスピンコートし、減圧下、80℃で6時間乾燥させ、コア5を作製した(図1:(f))。
さらに、下部クラッド3と同じ材料、手法にて、コア5上に上部クラッド6を形成した(図1:(g))。
そして、上部クラッド6上に金を真空蒸着し、上部電極7として形成した(図1:(h))。
最後にシリコン基板を結晶面にそってへき開することで光入出射端面とし、リッジ型光導波路とした。
図2中、D1、D2、D3はそれぞれ下部クラッドの厚さ、コアの厚さ、上部クラッドの厚さを示し、Hはリッジ部の高さ、Wは導波路幅を示す。
2・・・下部電極
3・・・下部クラッド
4・・・フォトレジスト
5・・・コア
6・・・上部クラッド
7・・・上部電極
8・・・光導波路
D1・・・下部クラッドの厚さ
D2・・・コアの厚さ
D3・・・上部クラッドの厚さ
H・・・リッジ部の高さ
W・・・導波路幅
Claims (14)
- トリアリールアミン構造を含む高分子化合物と非線形光学化合物とを含有することを特徴とする、光導波路のクラッド材料。
- 前記非線形光学化合物が、トリシアノ結合フラン環を有する化合物である、請求項1に記載のクラッド材料。
- 前記トリシアノ結合フラン環を有する化合物が、下記式(1)で表される化合物である、請求項2に記載のクラッド材料。
- 前記トリアリールアミン構造を含む高分子化合物が、式(2)又は式(3)で表される繰り返し単位を有する、請求項1に記載のクラッド材料。
- 前記Z1が、前記式(9)で表される一価の有機基であり、前記Z2が水素原子である、請求項5に記載のクラッド材料。
- コアと、その外周全体を取り囲む前記コアよりも屈折率の小さいクラッドからなる光導波路であって、前記クラッドが請求項1乃至請求項6のうち何れか一項に記載のクラッド材料より形成されてなる、光導波路。
- 前記コアが、式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物又はその誘導体を含む、請求項7に記載の光導波路。
- コアと、前記コアの周囲を取り囲み前記コアより屈折率の小さいクラッドとを有する請求項8に記載の光導波路の製造方法であって、
下部クラッドを請求項1乃至請求項6のうち何れか一項に記載のクラッド材料を用いて形成する工程、
前記下部クラッド上に請求項8に記載の式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物又はその誘導体を含むコアを形成する工程、及び、
前記コア上に請求項1乃至請求項6のうち何れか一項に記載のクラッド材料を用いて上部クラッドを形成する工程を含み、
上部クラッドを形成する工程の前及び/又は後に、前記コアに含まれる非線形光学化合物又はその誘導体を分極配向処理する工程を含む、
該光導波路を製造する方法。 - コアと、前記コアの周囲を取り囲み前記コアより屈折率の小さいクラッドとを有する請求項8に記載の光導波路の製造方法であって、
下部クラッドを請求項1乃至請求項6のうち何れか一項に記載のクラッド材料を用いて形成する工程、
前記下部クラッド上に、紫外線に対し感光性を有するレジスト層を形成し、前記レジスト層の表面に、フォトマスクを介して紫外光を照射・現像して、コアのマスクパターンを形成し、該マスクパターンをマスクとして前記下部クラッドにコアパターンを転写し、レジスト層を除去する工程、
下部クラッド上に請求項8に記載の式(1)で表されるトリシアノ結合フラン環を有する非線形光学化合物又はその誘導体を含むコアを形成する工程、及び、
前記コア上に請求項1乃至請求項6のうち何れか一項に記載のクラッド材料を用いて上部クラッドを形成する工程を含み、
上部クラッドを形成する工程の前及び/又は後に、前記コアに含まれる非線形光学化合物又はその誘導体を分極配向処理する工程を含む、
リッジ型光導波路を製造する方法。 - 前記分極配向処理が、電極による電界印加処理であることを特徴とする、請求項9又は請求項10に記載の製造方法。
- 式(2)又は式(3)で表される繰り返し単位を有する高分子化合物。
- 前記Z1が、前記式(9)で表される一価の有機基であり、前記Z2が水素原子である、請求項13に記載の高分子化合物。
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