WO2015151688A1 - Composition de résine pour utilisation dans un composant optique et composant optique l'utilisant - Google Patents

Composition de résine pour utilisation dans un composant optique et composant optique l'utilisant Download PDF

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Publication number
WO2015151688A1
WO2015151688A1 PCT/JP2015/055986 JP2015055986W WO2015151688A1 WO 2015151688 A1 WO2015151688 A1 WO 2015151688A1 JP 2015055986 W JP2015055986 W JP 2015055986W WO 2015151688 A1 WO2015151688 A1 WO 2015151688A1
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Prior art keywords
resin composition
optical
optical component
refractive index
viscosity
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PCT/JP2015/055986
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English (en)
Japanese (ja)
Inventor
友紀子 肥後
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日東電工株式会社
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Publication date
Application filed by 日東電工株式会社 filed Critical 日東電工株式会社
Priority to CN201580005784.XA priority Critical patent/CN105934690A/zh
Priority to SG11201606212RA priority patent/SG11201606212RA/en
Publication of WO2015151688A1 publication Critical patent/WO2015151688A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses

Definitions

  • the present invention is a transparent resin for optical applications, has high transparency that allows optical signals to pass through with low loss, and has excellent transparency and heat resistance.
  • the present invention relates to a photocurable resin composition suitable for component materials and the like, and an optical component using the same.
  • an imaging device used in a mobile phone, a digital camera, and the like an optical lens for imaging is mounted.
  • optical glass or transparent plastic material is used as a lens material.
  • polyolefin materials are made of plastic lens materials because of optical transparency and ease of lens design. It has become mainstream.
  • mounting of an image pickup device on a printed circuit board has generally been a pin insertion type using a socket, or a method in which a lens unit is attached to an image sensor after mounting the image sensor on a printed circuit board by solder reflow.
  • solder reflow mounting of the imaging device itself on a printed circuit board for the purpose of cheaper mass production.
  • a resin material having a higher refractive index is required.
  • a raw material having a high refractive index for example, a material having a benzene ring in the skeleton is generally known to have a high refractive index, although it is useful for increasing the refractive index, it is known that, on the contrary, the transparency is lowered due to the light absorption of the aromatic ring, and the heat discoloration is poor.
  • high refractive materials have a rigid structure, most materials are solid at room temperature and have a high melting point.
  • fluorene skeleton epoxy resins known as high refractive index materials have been studied in various ways. However, since they are solid at room temperature and the viscosity of the material is high even after melting, the resin increases with the increase in the amount added due to higher refractive index. There is a concern that the viscosity becomes high and the handling property deteriorates.
  • biphenyl skeleton epoxy resins having a glycidyl group at the para position which are generally used, are also solid at room temperature and have a high melting point. is there. In response to this, countermeasures have been taken by blending a solvent blend or a liquid epoxy resin (Patent Documents 2 and 3).
  • the present invention has been made in view of such circumstances, and has a high refractive index after curing, which is suitable as an optical component material having excellent handling properties and high transparency and excellent heat resistance. It is an object of the present invention to provide a resin composition for optical parts that can be used and an optical part using the same.
  • the present invention is such that the resin composition for optical parts has a viscosity at 25 ° C. of 0.1 to 20 Pa ⁇ s, and the refractive index of the cured product of the resin composition for optical parts is 1.
  • the first gist is a resin composition for optical parts having an Abbe number of 20 to 40 in the range of .57 or more.
  • the second aspect of the present invention is an optical component comprising a cured product of the resin composition for optical components according to the first aspect.
  • the present inventor has found that the viscosity of the resin composition before curing, the cured product of the resin composition Focusing on the refractive index and the Abbe number, experiments were repeated for these preferred ranges.
  • the viscosity at 25 ° C. of the resin composition for optical parts is in the range of 0.1 to 20 Pa ⁇ s
  • the refractive index of the cured product of the resin composition for optical parts is 1.57 or more
  • the Abbe number is It has been found that the intended purpose can be achieved by the resin composition for optical parts in the range of 20 to 40, and the present invention has been achieved.
  • the resin composition for optical parts of the present invention can be used in a solvent-free system, it can be said that it does not generate voids or the like during molding and is good for use as an optical part.
  • the resin composition for optical parts of the present invention has excellent handling properties and the like without using an organic solvent as described above because the viscosity at 25 ° C. is in the range of 0.1 to 20 Pa ⁇ s. Since both of them exhibit the above viscosity, the problem that the organic solvent volatilizes during the photocuring and molding and a void is generated in the cured product can be solved.
  • the resin composition for optical components of the present invention can be photocured on a transparent substrate such as a glass plate, a high-quality hybrid lens can be produced by integrating with the transparent substrate. It is.
  • the cured product of the resin composition for optical components has a high refractive index and a low Abbe, it has high transparency, can suppress heat discoloration, and improves optical design in a thin film.
  • the resin composition for optical components of the present invention contains an epoxy resin represented by the following general formula (1), an effect as a viscosity adjusting component that lowers the viscosity can be expected while being highly refraction. become.
  • Resin composition for optical parts The resin composition for optical parts of the present invention (hereinafter sometimes simply referred to as “resin composition”) has a viscosity at 25 ° C. of the resin composition before curing in the range of 0.1 to 20 Pa ⁇ s,
  • the cured product of the resin composition has a refractive index of 1.57 or more and an Abbe number of 20 to 40.
  • the physical properties such as viscosity will be described later.
  • the resin composition for optical parts of the present invention having such physical properties can be obtained by appropriately combining, for example, various epoxy resins, a curing agent for epoxy resins, and other additives (such as oxetane resins). And the resin composition for optical components of this invention can be used by a solventless system as above-mentioned.
  • the epoxy resin can be appropriately selected from various epoxy resins from the viewpoint of desired viscosity, refractive index, and photocurability, but has a fluorene skeleton, a biphenyl skeleton, and a naphthalene skeleton for high bending.
  • An epoxy resin, a bisphenol type epoxy resin, or the like is used.
  • an epoxy resin that can be expected to have an effect as a viscosity adjusting component that lowers the viscosity while having a high refraction
  • a biphenyl skeleton epoxy resin having a glycidyl group at the ortho position of the benzene ring is preferable.
  • An epoxy resin represented by the general formula (1) is given. These may be used alone or in combination of two or more.
  • R 1 to R 8 are all H (hydrogen atom).
  • the epoxy resin represented by the general formula (1) preferably has an epoxy equivalent in the range of 100 to 500.
  • the epoxy resin represented by the general formula (1) preferably has a refractive index of 1.57 or more and a melting point of 90 ° C. or less, particularly preferably a refractive index of 1.58 or more and a melting point. It is 85 degrees C or less.
  • epoxy resin represented by the general formula (1) examples include OPP-G manufactured by Sanko Co., Ltd.
  • the content of the epoxy resin represented by the general formula (1) is preferably 5 to 75% by weight, particularly preferably 10 to 70% by weight, based on the total resin components in the optical component resin composition. It is. That is, if the content is too small, it may be difficult to obtain a target low-viscosity and high-refractive resin composition. If the content is too large, the brittleness of the resin composition tends to decrease. Because it is seen.
  • the fluorene type epoxy resin may be an epoxy resin having a fluorene skeleton, and various fluorene type epoxy resins can be appropriately selected from the viewpoint of desired viscosity, refractive index, and photocurability.
  • Specific examples include PG-100 and EG-200 manufactured by Osaka Gas Chemical Company. These may be used alone or in combination of two or more.
  • the content of the fluorene type epoxy resin is preferably less than 60% by weight, particularly preferably less than 50% by weight, based on all resin components in the resin composition for optical parts. That is, if the content is too large, the viscosity tends to be high and the handling property tends to be lacking.
  • the fluorene type epoxy resin preferably has a refractive index of 1.60 or more, and particularly preferably has a refractive index of 1.62 or more.
  • monofunctional or bifunctional epoxy resins other than the epoxy resin represented by the general formula (1) and the fluorene type epoxy resin, etc. can also be blended.
  • the epoxy resin include alicyclic epoxy and hydrogenated bisphenol type epoxy resin, and bisphenol A type epoxy resin and bisphenol F type epoxy resin are preferably used particularly for the purpose of increasing the refractive index. .
  • a curing agent that promotes the polymerization reaction of the epoxy resin such as a photopolymerization initiator, a thermal acid generator, an imidazole-based curing catalyst, or a curing aid is appropriately used depending on the application. used.
  • a photopolymerization initiator any photopolymerization initiator may be used as long as it is capable of initiating cationic polymerization.
  • Onium salts can be used. Specifically, aromatic sulfonium salts, aromatic iodonium salts, aromatic phosphonium salts, aromatic sulfoxonium salts, and the like can be used. Of these, aromatic sulfonium salts are preferred from the viewpoint of photocurability.
  • the content of the epoxy resin curing agent is preferably set to 0.05 to 3 parts by weight with respect to 100 parts by weight of the resin component of the optical component resin composition. Particularly preferred is 0.05 to 2 parts by weight. That is, if the content is too small, the curability tends to deteriorate, and if it is too large, the curability is improved but the transparency of the cured product tends to be impaired.
  • An oxetane resin can be added to the resin composition for an optical component of the present invention from the viewpoint of improving handling properties and curability.
  • an oxetane compound having one or more oxetane rings per molecule is used.
  • the content of the oxetane compound is preferably set to 5 to 40% by weight with respect to the total resin components in the resin composition for optical parts. That is, when there is too much content, the tendency for it to become difficult to obtain the desired high refractive index will be seen.
  • the resin composition for optical parts of the present invention can be blended with a photosensitizer such as anthracene or an acid proliferator for the purpose of enhancing curability.
  • a photosensitizer such as anthracene or an acid proliferator
  • flexibility imparting agents such as synthetic rubbers and silicone compounds, and additives such as antioxidants, antifoaming agents, various pigments, dyes, inorganic fillers, and the like are appropriately blended as necessary. can do.
  • addition of an organic solvent or the like for the purpose of improving handling properties is not preferable from the viewpoint of generation of voids during molding and deterioration of characteristics, and it is preferably designed as a solventless system.
  • the resin composition for an optical component of the present invention includes, for example, an epoxy resin represented by the general formula (1) and an epoxy resin such as a fluorene type epoxy resin, a curing agent for the epoxy resin, and other if necessary.
  • an epoxy resin represented by the general formula (1) an epoxy resin represented by the general formula (1)
  • an epoxy resin such as a fluorene type epoxy resin, a curing agent for the epoxy resin, and other if necessary.
  • additives oxetane compounds and the like
  • the thus obtained resin composition for optical parts of the present invention has all the following physical properties (1) to (3), which is a feature of the present invention.
  • Viscosity The resin composition for optical parts of the present invention has a viscosity at 25 ° C. in the range of 0.1 to 20 Pa ⁇ s, preferably in the range of 0.1 to 18 Pa ⁇ s. That is, if the viscosity is too low, it is difficult to control the amount of the solution when dropping, for example, by an ink jet method, and if the viscosity is too high, the handling property is inferior.
  • the viscosity of the resin composition for optical parts is measured, for example, with a standard rotor (1 ° 34 ′ ⁇ R24) using an E80 type viscometer (RE-80U) manufactured by Toki Sangyo Co., Ltd. under a temperature condition of 25 ° C. Can be measured.
  • the cured product has a refractive index of 1.57 or more, preferably in the range of 1.59 to 1.64. That is, if the refractive index of the cured product is too low, for example, when forming an optical lens or the like for a mobile device or the like, the lens becomes thick, which may make it difficult to reduce the height of the camera module.
  • the refractive index of the cured product is, for example, by pouring a resin composition (liquid resin) for optical components into a transparent mold having a predetermined size (for example, 1 ⁇ 1.5 ⁇ 0.5 cm), and ultraviolet (UV). After being irradiated and cured (for example, 10,000 mJ / cm 2 ), it is removed from the mold and subjected to heat treatment under predetermined conditions (for example, 150 ° C. ⁇ 1 hour). After polishing the surface of the molded product thus obtained using a grinder, the refractive index in a 25 ° C. environment can be measured using a refractometer (manufactured by Atago Co., Ltd.).
  • the cured product has an Abbe number in the range of 20 to 40, preferably in the range of 20 to 35. That is, if the Abbe number of the cured product is too small, the wavelength dependency of the resulting cured product increases, and there are concerns such as color bleeding depending on the application.
  • the Abbe number refers to the reverse dispersion ability in an optical component (cured body) such as a so-called optical lens.
  • an optical component cured body
  • a cured body of a resin composition for optical components It is a value measured by an Abbe refractometer at 25 ⁇ 10 ° C. using a test piece) and calculated by the following mathematical formula (x).
  • Abbe number ([refractive index at 589 nm] ⁇ 1) / ([refractive index at 486 nm] ⁇ [refractive index at 656 nm]) (x)
  • the measurement of the Abbe number of the cured product can be performed using, for example, a refractometer (for example, manufactured by Atago Co., Ltd.) after polishing the surface of the cured product (optical component or the like) with a grinder.
  • a refractometer for example, manufactured by Atago Co., Ltd.
  • the resin composition for optical parts of the present invention preferably has a viscosity at 40 ° C. in the range of 0.05 to 5.0 Pa ⁇ s, more preferably in the range of 0.05 to 4.5 Pa ⁇ s. is there. That is, when the viscosity is too low, for example, in the case of an ink jet method, the liquid amount tends to be difficult to control, and when the viscosity is too high, the handling property tends to be inferior.
  • the transmittance of the cured product at a wavelength of 400 nm is preferably 80% or more, more preferably 83% or more. That is, when the transmittance is too low, the transparency tends to be inferior.
  • the resin composition for optical parts of the present invention is used, for example, as follows. That is, the resin composition is potted on a transparent substrate such as glass, and a desired molding die is pressed onto the resin composition to fill the resin composition into the molding die, and light is irradiated there. It can be cured by doing so. Then, by removing the molding die from the molding die, a cured body (molded product) of the resin composition integrated on the transparent substrate can be obtained. Alternatively, the resin composition can be filled into a transparent mold that transmits light and photocured.
  • the resin composition for optical parts of the present invention can produce, for example, a hybrid lens by such a production method.
  • the resin composition for optical components of the present invention can be cured by itself in a molding die to be an optical component such as an optical lens.
  • the molded body (cured body) thus obtained may be removed from the mold and further subjected to heat treatment at a predetermined temperature as necessary.
  • the heat resistance stability of the cured product can be enhanced, and particularly in the case of a laminate with a transparent substrate, the adhesion between the substrate and the cured resin product can be enhanced.
  • a UV lamp or a single band lamp having a specific wavelength can be used as an apparatus, and a low pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a xenon lamp, or the like can be used as a light source. it can.
  • the irradiation amount is preferably 2000 to 200000 mJ / cm 2 . That is, if the irradiation amount is less than the above range, the desired cured product shape may not be obtained on the substrate due to insufficient curing, and if it exceeds the above range, photodegradation occurs due to excessive irradiation, and thereafter This is because it may be colored by heat treatment or the like, and transparency may be impaired.
  • the heat treatment conditions after the light irradiation are preferably 80 to 170 ° C. for about 1 hour.
  • the resin composition for optical components of the present invention can be molded into a sheet shape without depending on the molding die as described above.
  • the resin composition for optical parts of the present invention obtained as described above has an effect that a mechanical property which is small in discoloration and stable against heat stress is obtained even by heat during solder reflow. Therefore, it can be advantageously used when parts and the like mounted with the cured product of the present invention are collectively mounted by solder reflow.
  • the resin composition for an optical component of the present invention is used as a molding material (optical component material) for an optical component such as an optical lens by the manufacturing method as described above, and is light-cured for fixing an optical waveguide or an optical component. It can be used for mold adhesives.
  • R 1 to R 8 are all H (refractive index 1.59, melting point 50 ° C., epoxy equivalent 226 g / eq) [A-2]
  • R 5 is a phenyl group and R 8 is —O—Gly (Gly: glycidyl group), and other R 1 to R 7 are H (refractive index 1.62, melting point 70 ° C., Epoxy equivalent 165 g / eq)
  • R 3 is —O—Gly (Gly: glycidyl group), and other R 1 to R 8 are H (refractive index 1.585, melting point 40 ° C., epoxy equivalent 113 g / eq).
  • Triarylsulfonium salt photopolymerization initiator (photoacid generator) (50 wt% propylene carbonate solution) in which the anion component is Sb 6 ⁇ and the cation component is the following structural formula (2)
  • the Abbe number was calculated based on the above formula (x) in the Abbe measurement mode of the same apparatus (manufactured by Atago Co., Ltd.) as the refractive index measurement. As a result, an Abbe number of less than 20 or more than 40 was evaluated as x, and an Abbe number of 20 or more and 40 or less was evaluated as ⁇ .
  • the example product having a low viscosity and a high refractive index and a low Abbe obtained better results regarding transparency than the comparative example product. Therefore, by using the resin composition for optical parts of the example product, it becomes possible to provide an optical part such as an optical lens having a high refractive index and excellent heat discoloration. In addition, optical components using this resin composition have stable mechanical properties against heat stress without being discolored by heat during solder reflow. It can be used advantageously.
  • Comparative Examples 1 to 3 are inferior in handling properties because the viscosity at 25 ° C. is extremely high and the viscosity at 40 ° C. is also extremely high. It is clear that Comparative Examples 1 and 2 are particularly unsuitable as optical component materials because of their low transparency. Moreover, since the comparative example 4 product had the high Abbe number of the hardened
  • the resin composition for optical parts of the present invention can be a three-dimensional molded article (cured product) having a high refractive index while having high transparency, a molding material for optical parts such as optical lenses (materials for optical parts) ) And optical applications such as a photo-curing adhesive for fixing optical components.
  • the optical component using the resin composition for optical components of the present invention has high reliability, it can be used for optical components (optical products) such as optical lenses.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Eyeglasses (AREA)

Abstract

L'invention concerne une composition de résine pour utilisation dans un composant optique, qui présente une viscosité dans la plage de 0,1 à 20 Pa∙s à 25 °C et, de ce fait, excelle en termes de propriétés de manipulation et analogues, et comme ladite composition de résine présente une viscosité comprise dans ladite plage sans l'aide d'un solvant organique, on élimine des problèmes tels qu'une volatilisation de solvant organique pendant un durcissement à la lumière et un moulage et des vides formés dans la substance durcie. Cette composition de résine pour utilisation dans un composant optique peut être durcie à la lumière sur la partie supérieure d'un substrat transparent tel qu'une plaque de verre, en intégrant ladite composition de résine avec ledit substrat transparent et en rendant possible la fabrication d'une lentille hybride de haute qualité. La substance obtenue par durcissement de cette composition de résine pour utilisation dans un composant optique a un indice de réfraction élevé et un nombre Abbe faible et présente ainsi un degré élevé de transparence et une décoloration minimale par la chaleur, ce qui améliore les propriétés de conception optique d'une couche mince de ladite substance. En outre, par durcissement de cette composition de résine par elle-même, une lentille en plastique hautement résistante à la chaleur, par exemple, peut être fabriquée.
PCT/JP2015/055986 2014-03-31 2015-02-27 Composition de résine pour utilisation dans un composant optique et composant optique l'utilisant WO2015151688A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201580005784.XA CN105934690A (zh) 2014-03-31 2015-02-27 光学部件用树脂组合物及使用该树脂组合物制造的光学部件
SG11201606212RA SG11201606212RA (en) 2014-03-31 2015-02-27 Resin composition for optical component, and optical component produced by using the resin composition

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JP2014-071402 2014-03-31
JP2014071402A JP6418673B2 (ja) 2014-03-31 2014-03-31 光学部品用樹脂組成物およびそれを用いた光学部品

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JP (1) JP6418673B2 (fr)
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SG (1) SG11201606212RA (fr)
TW (1) TW201540765A (fr)
WO (1) WO2015151688A1 (fr)

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SG11201606212RA (en) 2016-10-28
TW201540765A (zh) 2015-11-01

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