WO2008016000A1 - Matériau composite et élément optique - Google Patents

Matériau composite et élément optique Download PDF

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Publication number
WO2008016000A1
WO2008016000A1 PCT/JP2007/064870 JP2007064870W WO2008016000A1 WO 2008016000 A1 WO2008016000 A1 WO 2008016000A1 JP 2007064870 W JP2007064870 W JP 2007064870W WO 2008016000 A1 WO2008016000 A1 WO 2008016000A1
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WO
WIPO (PCT)
Prior art keywords
resin
compound
composite material
optical
optical element
Prior art date
Application number
PCT/JP2007/064870
Other languages
English (en)
Japanese (ja)
Inventor
Hiroaki Ando
Hideaki Wakamatsu
Original Assignee
Konica Minolta Opto, Inc.
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 Konica Minolta Opto, Inc. filed Critical Konica Minolta Opto, Inc.
Publication of WO2008016000A1 publication Critical patent/WO2008016000A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/01—Hydrocarbons

Definitions

  • the present invention relates to a composite material suitably used as an optical element material and an optical element formed thereby.
  • glass materials and resin materials are mainly used as materials constituting optical elements, and among them, resin materials are often used because they are inexpensive and have excellent moldability.
  • resin materials are often used because they are inexpensive and have excellent moldability.
  • a resin material applicable to optical elements for example, a copolymer of cyclic olefin and ⁇ -olefin (see Patent Document 1) is known.
  • the resin material has a high coefficient of linear expansion, the refractive index is changed by temperature change. Fluctuating to obtain optical stability.
  • Patent Document 2 a composite material in which an inorganic filler (fine particles) is mixed in a resin material can be expected to suppress the linear expansion coefficient and to stabilize the refractive index.
  • Patent Document 2 an organic-inorganic composite material using silica-based particles has been proposed in order to improve the high linear expansion coefficient, which is a drawback of resin materials.
  • Silica alone has a relatively low refractive index, but using a composite material eliminates the disadvantages of silica, which has a low refractive index, and broadens the range of applications as an optical material.
  • Patent Document 1 JP 2002-105131 A
  • Patent Document 2 Japanese Patent Laid-Open No. 2005-146042
  • the composite material has poor compatibility between the resin material and the inorganic filler and the inorganic filler is difficult to disperse in the resin material, the optical element itself is inferior in transparency (light transmittance is reduced).
  • Improving the transparency by increasing the affinity of the inorganic filler for the resin material requires a surface treatment, which increases costs and completely overcomes the transparency problem even if the surface treatment is applied. It does not lead to.
  • the moisture absorption rate increases and the installation environment It becomes difficult to stabilize the refractive index with respect to fluctuations in the range.
  • An object of the present invention is to improve the transparency and reduce the moisture absorption rate while suppressing the linear expansion coefficient.
  • the first aspect of the present invention provides:
  • the compound having an adamantyl group may be a compound having only an adamantane skeleton, a compound having an adamantane skeleton in the main chain, or a compound having an adamantane skeleton in the side chain. Also good.
  • the resin is preferably a cycloolefin resin.
  • the second aspect of the present invention is:
  • FIG. 1 is a schematic diagram showing an internal structure of an optical pickup device. Explanation of symbols
  • the composite material contains (1) a resin and (2) a compound having an adamantyl group.
  • (1) a resin and (2) a compound having an adamantyl group will be described, respectively, followed by (3) a method for producing a composite material, (4) properties of the composite material, and (5) a method for producing an optical element.
  • thermoplastic resin a thermosetting resin, a photocurable resin, or the like
  • the resin is thermoplastic due to the workability as an optical element and the molding cycle time.
  • An acrylic resin, a cyclic olefin resin, a polycarbonate resin, a polyester resin, a polyether resin, a polyamide resin, or a polyimide resin, which are preferable to be a hydrophobic resin, are particularly preferable from the viewpoint of low hygroscopicity.
  • a resin is preferred.
  • a silicon resin is preferably used as the curable resin which may be a curable resin such as a thermosetting resin or a photocurable resin.
  • the resin the compounds described in JP-A-2003-73559 can be listed, and preferred compounds are shown in Table 1 below. Of these resins, those having a moisture absorption rate of 0.5% or less are preferred, and those having a moisture absorption rate of 0.2% or less are more preferred.
  • the compounds having an adamantyl group include (2.1) a compound consisting only of an adamantane skeleton, (2.2) a compound having an adamantane skeleton in the main chain, and (2.3) having an adamantane skeleton in the side chain.
  • 1,3-dib mouth modamantane of the following formula (3) is used as a starting material
  • jetyl ether 1,3-Dehydroadamantane of the following formula (4) may be synthesized by reaction with potassium sodium alloy in a mixed solvent of HMPA and HMPA, and the 1,3-dehydroadamantane may be heated at 160 ° C.
  • R, R ′ is preferably a linear, branched or cyclic alkyl group.
  • N is an integer of 1 or more.
  • force-coupling polymerization As a method for synthesizing poly (1,3-adamantane) of the following formula (5) into which a substituent is introduced, force-coupling polymerization can be applied.
  • a novel monomer 3, 3 'in formula (6) below, 5'-dibutyl mouth 1, 5 '-dibutyl- 1, 1' biadamantane, 3, 3 'in formula (7) below, 5', jib mouth mode 5, 5 ', 7, 1'-Tetrabutyl-1, ⁇ 'Viadamantane may be synthesized and coupling polymerization using sodium metal in n-octane may be performed.
  • R is preferably a linear, branched or cyclic alkyl group! / ′.
  • N is an integer of 2 or more.
  • poly (1,3-adamantane) of the above formula (8) into which a substituent is introduced include poly (1,3, -adamantane) of the following formulas (9), (10), (11) Can be mentioned.
  • n is an integer of 1 or more.
  • an adamantane derivative may be synthesized as a main raw material.
  • n is an integer of 1 or more.
  • the compound having an adamantane skeleton in the side chain is a compound (copolymer) of the following formula (30).
  • R is a unit constituting the main chain of the compound
  • n is an integer of 1 or more.
  • examples of the compound corresponding to the “side chain” include compound forces S of the following formulas (3 ;!) to (40).
  • a polymerization method any method such as ordinary radical polymerization or canyon polymerization may be used.
  • the method for producing the composite material is to disperse the compound having an adamantyl group described in each item of “(2. 1 2. 3)” above in the resin! /.
  • the compound having an adamantyl group synthesized in the synthesis step and a resin (particularly a thermoplastic resin) are mixed, and the compound having an adamantyl group is dispersed in the resin.
  • a method for mixing the compound having an adamantyl group and the resin it is preferable to use a melt-kneading method from the viewpoint of reducing the amount of volatile substances used.
  • the compound having an adamantyl group and the resin may be added and kneaded all at once, or may be divided and added in stages.
  • a method of dividing addition a method of adding one component in several times, a method of adding one component at a time and adding other components stepwise, or a combination of these is used. I can do it.
  • the addition of the compound having an adamantyl group can be performed in a powder or agglomerated state. Force that can be added in a state where a compound having an adamantyl group is dispersed in a liquid. In this case, it is necessary to perform a devolatilization treatment after kneading, and the aggregated particles are previously formed into primary particles. It is preferable to add after being dispersed in.
  • melt-kneading method when a compound having an adamantyl group and a resin are kneaded in advance, components other than the resin (thermoplastic resin) that have not been added in advance are added and further melt kneaded. You can knead them! /, And you can add them in stages and knead them! /.
  • one kind of gas selected from the inert gases nitrogen, helium, neon, argon, krypton, and xenon, or a mixture of two or more kinds of gases is used. It is preferable to perform mixing in an atmosphere. However, even general gases such as carbon dioxide, ethylene gas, and hydrogen gas are not reactive to the material to be kneaded! /, If mixed with the inert gas described above, the gas is used.
  • general gases such as carbon dioxide, ethylene gas, and hydrogen gas are not reactive to the material to be kneaded! /, If mixed with the inert gas described above, the gas is
  • the melt-kneading method is used in the dispersion step, it is preferable to eliminate residual oxygen as much as possible in the reaction system in the melt-kneading apparatus.
  • the oxygen content is preferably 1% or less, and more preferably 0.2% or less. This is because the resin is deteriorated by the oxidation reaction with oxygen and coloration is likely to occur.
  • a closed kneading apparatus or a batch kneading apparatus such as a lab plast mill, a Brabender, a Banbury mixer, a kneader, and a roll can be cited.
  • a continuous melt kneading apparatus such as a single screw extruder or a twin screw extruder can be used.
  • a continuous melt-kneading apparatus such as an extruder, it is possible to add the components to be added step by step from the middle of the cylinder.
  • dispersion apparatus for the mixture various dispersion treatment machines such as a bead mill disperser, an ultrasonic disperser, a high-speed stirring disperser, and a high-pressure disperser can be applied. It can.
  • force S such as dinoreconia beads and glass beads, and zirconia beads are preferably used.
  • the diameter of the beads to be used is smaller, and the preferred diameter is in the range of 0.001 to 0.1 mm.
  • additives may be added alone or in combination as necessary in the composite material production process! /.
  • additives examples include antioxidants, light stabilizers, heat stabilizers, weather stabilizers, stabilizers such as ultraviolet absorbers and near infrared absorbers, resin modifiers such as lubricants and plasticizers, and soft polymers. And anti-clouding agents such as alcoholic compounds, coloring agents such as dyes and pigments, other antistatic agents, flame retardants and the like.
  • antioxidants include phenolic antioxidants, phosphorus antioxidants, and phenolic antioxidants. By blending these antioxidants, it is possible to prevent the coloring and strength of the lens from being deteriorated due to oxidative deterioration during molding without reducing transparency and heat resistance.
  • antioxidants can be used alone or in combination of two or more, and the blending amount thereof is appropriately selected within a range not impairing the object of the present invention. However, it is preferably within a range of 0.00;! To 20 parts by mass with respect to 100 parts by mass of the composite material, more preferably within a range of 0.01 to 10 parts by mass.
  • phenolic antioxidant conventionally known ones can be applied.
  • 2-tbutyl-6- (3-tbutyl-2-hydroxyl-5) described in JP-B-63-179953.
  • (Methylbenzyl) 4 methylphenyl acrylate, 2, 4 di-tert-aminol-6- (1- (3,5 di-tert-aminol-2-hydroxyphenyl) ethynole) phenyl acrylate, etc.
  • Octadecinole 1- (3,5 di-tert-butyl-4-hydroxyphenyl) propionate and other acrylate compounds described in Japanese Patent No.
  • Alkyl-substituted phenolic compounds such as propionate), 6- (4-hydroxy-3,5-di-tert-butylanilino) -1,2,4 bisoctylthio-1,3,5 triazine, 4 bisoctylthio-1,3,5-triazine, Examples include 2-azine thiol 4,6-bis (3,5-di-t-butyl-4-oxyanilino) -triazine group-containing phenolic compounds such as 1,3,5-triazine.
  • the phosphorus antioxidant is not particularly limited as long as it is a substance usually used in the general resin industry.
  • triphenyl phosphite diphenylisodecyl. Phosphite, phenyl diisodecyl phosphite, tris (noyulpheninole) phosphite, tris (dinouylfeninore) phosphite, tris (2,4 di-t-butylphenolophosphite), 10— (3,5 di t-butyl-4-hydroxybenzyl) 9, 10 dihydro-9 oxa 10-phosphaphenanthrene 10-oxide and other monophosphite compounds, 4, A'-butylidenebis (3-methyl-6-t butylphenol tri Decyl phosphite), 4, A′-isopropylidene monobis (phenyl didialkyl (C 12 -C 15 phosphite))
  • tris (noyulphenyl) phosphite tris (dinoylphenyl) phosphite, and tris (2,4 di-tert-butylphenyl) phosphite are particularly preferred.
  • iow antioxidants include dilauryl 3, 3 thiodipropionate, dimyristinole 3, 3'-thiodipropionate, distearyl 3, 3-thiodipropionate, lauryl stearyl 3, 3 —Chiodipropionate, pentaerythritol-tetrakis (/ 3 lauryl thiopropionate), 3, 9 bis (2 dodecylthioethyl) 2, 4, 8, 10—tetraoxaspiro [5, 5] undecane Etc.
  • amine-based antioxidants such as diphenylamine derivatives, nickel or zinc thiocarbamate, etc. can also be applied as antioxidants. It is.
  • a compound group having a minimum temperature at the glass transition temperature of 30 ° C or less may be blended as the cloudiness inhibitor.
  • examples of the light-resistant stabilizer include benzophenone-based light-resistant stabilizer, benzotriazole-based light-resistant stabilizer, hindered amine-based light-resistant stabilizer, and the like. From the viewpoint of properties and the like, it is preferable to use a hindered amine light-resistant stabilizer (hereinafter referred to as “HALS”). As such HALS, those having a low molecular weight, medium molecular weight and high molecular weight can be appropriately selected. However, when producing molded products from composite materials, low molecular weight or medium molecular weight HALS may be used. Particularly when a film-like molded body is produced, it is preferable to use high molecular weight HALS.
  • HALS hindered amine light-resistant stabilizer
  • HALS with a relatively small molecular weight includes LA-77 (Asahi Denka), Tinuvin765 (CSC), Tinuvinl23 (CSC), Tinuvin440 (CSC), Tinuvinl44 (CSC), HostavinN20 (Hoechst) Manufactured) and the like.
  • Examples of medium molecular weight HALS include LA-57 (Asahi Denka), LA-52 (Asahi Denka), LA-67 (Asahi Denka), LA-62 (Asahi Denka), and the like. It is done.
  • HALS with large molecular weights are LA-68 (Asahi Denka), LA-63 (Asahi Denka), Ho stavinN30 (Hoechst), Chimassorb944 (CSC), Chimassorb2020 (CSC), Chimassorbl l9 (CSC), Tinuvin622 (CSC), CyasorbUV-3346 (Cytec), CyasorbUV-3529 (Cytec), Uvasil299 (GLC), etc.
  • the light transmittance of the composite material produced as described above is preferably 50% or more, more preferably 70% or more, with respect to 405 nm light when the thickness is 3 mm. More preferably, it is 85% or more.
  • the Abbe number of the composite material it is preferable to use particles capable of obtaining anomalous force dispersibility in which various values can be selected by selecting a compound having an adamantyl group or a resin.
  • the composite material can be effectively used for achromatization, and its value may increase.
  • the water absorption rate of the composite material is preferably 2% or less, more preferably 1% or less in an environment of a temperature of 80 ° C and a relative humidity of 90%, more preferably 0.5%. It is most preferable that
  • the water absorption rate is expressed in mass% unless otherwise specified.
  • the water absorption rate can be measured from a change in mass when a pre-dried composite material is stored for a certain period of time under specific high temperature and high humidity conditions. This embodiment In the method, the water content when dried is measured by the Karl Fischer method, and the mass change is measured after the subsequent water absorption, thereby calculating the water absorption rate more accurately.
  • the composite material is preferably negative in the AMES test! /. This is because a positive result in the AMES test may impair the user's health, increase the environmental burden, and reduce the material stability.
  • the molding method is not particularly limited, but the melt molding method is preferable from the viewpoint of characteristics such as low birefringence, mechanical strength and dimensional accuracy in the molded product.
  • the melt molding method include press molding, extrusion molding, and injection molding. From the viewpoint of productivity, it is preferable to apply injection molding as the melt molding method.
  • injection molding as the melt molding method.
  • a molded product with a photocurable resin, cast polymerization or the like can be used.
  • the molding condition is a force that is appropriately selected according to the purpose of use or molding method.
  • the temperature of the composite material in injection molding an appropriate fluidity is imparted to the resin at the time of molding to reduce the distortion of the molded product.
  • the temperature is in the range of 150 ° C to 400 ° C from the viewpoints of preventing silver streaks due to thermal decomposition of the resin and effectively preventing yellowing of the molded product. More preferably, it is within the range of 200 ° C to 350 ° C, and particularly preferably within the range of 200 ° C to 330 ° C.
  • the molded product can be used in various forms such as a spherical shape, a rod shape, a plate shape, a cylindrical shape, a tubular shape, a tubular shape, a fibrous shape, a film or a sheet shape, and has a low birefringence, Since it is excellent in transparency, mechanical strength, heat resistance, low water absorption, etc., it can be applied to various optical components.
  • optical lens examples include an optical lens and an optical prism.
  • lenses include: camera imaging lenses; microscopes, endoscopes, telescope lenses, and other lenses; spectacle lenses and other light-transmissive lenses; CD, CD-ROM, WORM (write-once optical discs) ), MO (rewritable optical disk; magneto-optical disk), MD (laser scanning system lens such as mini-debeam printer f ⁇ lens, sensor lens, etc .; prism lens of camera lens system).
  • optical applications include light guide plates such as liquid crystal displays; optical films such as polarizing films, retardation films, and light diffusion films; light diffusion plates; optical cards; liquid crystal display element substrates.
  • optical element according to the present invention is also suitably used as various filters, gratings, optical fibers, flat optical waveguides, and the like.
  • the molded article is suitably used as an optical element such as a pickup lens requiring low birefringence or a laser scanning system lens.
  • optical pickup device 1 in which the optical element according to the present invention is used as the objective lens 7 will be described with reference to FIG.
  • FIG. 1 is a schematic diagram showing the internal structure of the optical pickup device 1.
  • the optical pickup device 1 includes a semiconductor laser oscillator 2 as a light source.
  • a semiconductor laser oscillator 2 As shown in FIG. 1, the optical pickup device 1 includes a semiconductor laser oscillator 2 as a light source.
  • the direction force away from the semiconductor laser oscillator 2 is collimator 3, beam splitter 4, 1/4 wavelength plate 5, aperture 6,
  • the objective lens 7 is sequentially arranged.
  • a sensor lens group 8 and a sensor 9 composed of two sets of lenses are sequentially disposed in a position close to the beam splitter 4 and in a direction perpendicular to the optical axis of the blue light described above.
  • the objective lens 7 as an optical element is disposed at a position facing the optical disc D, and collects the blue light emitted from the semiconductor laser oscillator 2 on one surface of the optical disc D. It is summer.
  • Such an objective lens 7 is provided with a two-dimensional actuator 10, and the objective lens 7 is movable on the optical axis by the operation of the two-dimensional actuator 10.
  • the optical pickup device 1 emits blue light from the semiconductor laser oscillator 2 at the time of recording information on the optical disc D or at the time of reproducing information recorded on the optical disc D. As shown in FIG. 1, the emitted blue light becomes a light beam L1, which is transmitted through the collimator 3 and collimated into infinite parallel light. Transparent. Further, after passing through the aperture 6 and the objective lens 7, a condensing spot is formed on the information recording surface D2 via the protective substrate D1 of the optical disc D.
  • the light that forms the focused spot is modulated by the information pits on the information recording surface D2 of the optical disc D and reflected by the information recording surface D2. Then, the reflected light becomes a light beam L 2, is sequentially transmitted through the objective lens 7 and the diaphragm 6, is changed in polarization direction by the quarter-wave plate 5, and is reflected by the beam splitter 4. After that, astigmatism is given through the sensor lens group 8 and received by the sensor 9, and finally converted into an electric signal by being photoelectrically converted by the sensor 9.
  • the numerical aperture NA required for the objective lens 7 varies depending on the thickness dimension of the protective substrate D1 and the size of the information pit in the optical disc D. In this embodiment, it is a high-density optical disc D, and its numerical aperture is set to 0.85.
  • the washed alumina was dried at 90 ° C to remove ethanol, and then calcined at 450 ° C.
  • the particle diameter was about 10 nm.
  • the alumina particles were referred to as “Compound 2”.
  • a dropping device, a thermometer, a nitrogen gas introduction tube, a stirring device, and a reflux condenser were installed in a 4-liter 4-separable flask, and 20 g of benzene was charged into the flask and heated at about 80 ° C.
  • the polymer was designated as “Compound 3”.
  • Cycloolefin resin (APEL5014 manufactured by Mitsui Chemicals) without kneading with the above compounds 1-4 As “Composite Material 5”.
  • the composite materials 1 to 5 were injection molded to obtain a molded sample for measurement (thickness 3 mm). These compacts were designated as “Samples !-5”.
  • Samples 1 and 3 have the same linear expansion coefficient as Sample 2. Suppressed linear expansion compared to Samples 4 and 5 It has an effect and is excellent in terms of light transmittance, moisture absorption, and refractive index. From the above, it can be seen that it is useful to include a compound having an adamantyl group in the resin.

Abstract

La présente invention concerne un élément optique offrant une meilleure transparence et une réduction de l'absorptivité d'humidité tout en éliminant un coefficient de dilatation thermique. Une lentille d'objectif est formée en tant qu'élément optique par moulage d'un matériau composite. Le matériau composite contient un composé comprenant un groupe adamantyle dans une résine.
PCT/JP2007/064870 2006-08-04 2007-07-30 Matériau composite et élément optique WO2008016000A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006212966 2006-08-04
JP2006-212966 2006-08-04

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WO2008016000A1 true WO2008016000A1 (fr) 2008-02-07

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000235102A (ja) * 1999-02-15 2000-08-29 Konica Corp 熱可塑性シリコーン系樹脂を含有する樹脂組成物からなる光学素子及び光学用レンズ
JP2001348492A (ja) * 2000-06-08 2001-12-18 Daicel Chem Ind Ltd 難燃性樹脂組成物
WO2003102069A1 (fr) * 2002-05-30 2003-12-11 Ciba Specialty Chemicals Holding Inc. Polypropylenes $g(b)-cristallins
JP2005290061A (ja) * 2004-03-31 2005-10-20 Sumitomo Bakelite Co Ltd 高分子組成物および架橋高分子
JP2006321987A (ja) * 2005-04-21 2006-11-30 Mitsubishi Chemicals Corp 樹脂組成物及び成形体

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000235102A (ja) * 1999-02-15 2000-08-29 Konica Corp 熱可塑性シリコーン系樹脂を含有する樹脂組成物からなる光学素子及び光学用レンズ
JP2001348492A (ja) * 2000-06-08 2001-12-18 Daicel Chem Ind Ltd 難燃性樹脂組成物
WO2003102069A1 (fr) * 2002-05-30 2003-12-11 Ciba Specialty Chemicals Holding Inc. Polypropylenes $g(b)-cristallins
JP2005290061A (ja) * 2004-03-31 2005-10-20 Sumitomo Bakelite Co Ltd 高分子組成物および架橋高分子
JP2006321987A (ja) * 2005-04-21 2006-11-30 Mitsubishi Chemicals Corp 樹脂組成物及び成形体

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