Classifications

• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
  • C08F210/02—Ethene
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
  • C08F232/02—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
  • C08F232/04—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having one carbon-to-carbon double bond
• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
  • C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F4/00—Polymerisation catalysts
  • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
  • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
  • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
  • C08F4/62—Refractory metals or compounds thereof
  • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
  • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
  • C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound

Definitions

• the present invention relates to optical components.
• Cyclic olefin copolymers are used as optical components such as optical lenses because they have excellent optical performance.
• Examples of the technique relating to the cyclic olefin-based copolymer used for the optical component include those described in Patent Document 1 (Japanese Unexamined Patent Publication No. 2015-199939).
• Patent Document 1 discloses a cyclic olefin resin composition containing a cyclic olefin copolymer and a diglycerin fatty acid ester. Patent Document 1 describes that when such a cyclic olefin resin composition is used, a molded product having excellent optical performance and further suppressing deterioration of optical performance under high temperature and high humidity conditions can be obtained.
• Cyclic olefin copolymers are widely used in optical components such as camera lenses because of their excellent optical properties and mechanical properties.
• the optical component containing the cyclic olefin copolymer is exposed to a high temperature environment for a long time, the refractive index may change and the optical performance may deteriorate. I found that there is.
• the present invention has been made in view of the above circumstances, and provides an optical component having a high refractive index and excellent long-term reliability of optical performance in a high temperature environment.
• the cyclic olefin copolymer (A) is The structural unit (a) derived from at least one olefin represented by the following general formula (I) and A structural unit (b) derived from at least one cyclic olefin represented by the following general formula (II) and It has a structural unit (c) derived from at least one cyclic olefin represented by the following general formula (III), and has.
• An optical component in which the content of the structural unit (a) is 50 mol% or less when the total content of the structural unit (a), the structural unit (b) and the structural unit (c) is 100 mol%.
• R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms.
• R 1 to R 8 are independently hydrogen atoms, halogen atoms or hydrocarbon groups having 4 or less carbon atoms, and R 5 to R 8 are bonded to each other to form a single ring.
• n is 0 or 1
• m is 0 or a positive integer
• n + m is a positive integer
• q is 0 or 1
• a and R b are independently hydrogen atoms, halogen atoms or hydrocarbon groups, and R 15 to R 18 may be bonded to each other to form a monocyclic or polycyclic ring, and the monocyclic or polycyclic ring or polycycle may be formed.
• the ring may have a double bond and may form an alkylidene group with R 15 and R 16 or with R 17 and R 18).
• Tg glass transition point
• An optical component in which the ratio ((b) / (c)) of the content of the structural unit (b) to the content of the structural unit (c) in the cyclic olefin copolymer (A) is 2 or more. .. [4] In the optical component according to any one of the above [1] to [3].
• the structural unit (b) in the cyclic olefin copolymer (A) contains a repeating unit derived from bicyclo [2.2.1] -2-heptene, and is contained in the cyclic olefin copolymer (A).
• the above-mentioned structural unit (c) is tetracyclo [4.4.0.1 2,5 . 1 7, 10 ] -3- An optical component containing a repeating unit derived from dodecene. [5] In the optical component according to any one of the above [1] to [4], An optical component in which the structural unit (a) in the cyclic olefin copolymer (A) contains a repeating unit derived from ethylene.
• optical component In the optical component according to any one of the above [1] to [5], An optical component that is an f ⁇ lens, an imaging lens, a sensor lens, a prism, or a light guide plate. [7] In the optical component according to any one of the above [1] to [6]. Optical components that are in-vehicle camera lenses or camera lenses for mobile devices.
• an optical component having a high refractive index and excellent long-term reliability of optical performance in a high temperature environment.
• the optical component according to the present embodiment is an optical component containing the cyclic olefin copolymer (A), and the cyclic olefin copolymer (A) is at least one kind represented by the following general formula (I).
• the structural unit (c) derived from the cyclic olefin When the structural unit (c) derived from the cyclic olefin is provided and the total content of the structural unit (a), the structural unit (b) and the structural unit (c) is 100 mol%, the structural unit (a) ) Is 50 mol% or less.
• R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms.
• R 1 to R 8 are independently hydrogen atoms, halogen atoms or hydrocarbon groups having 4 or less carbon atoms, and R 5 to R 8 are bonded to each other to form a single ring. it may also be, and may be monocyclic has have a double bond, or may form a R 5 and by the R 6, or alkylidene group and R 7 and R 8.
• n is 0 or 1
• m is 0 or a positive integer
• n + m is a positive integer
• q is 0 or 1
• a and R b are independently hydrogen atoms, halogen atoms or hydrocarbon groups
• R 15 to R 18 may be bonded to each other to form a monocyclic or polycyclic ring, and the monocyclic or polycyclic ring or polycycle may be formed.
• the ring may have a double bond and may form an alkylidene group with R 15 and R 16 or with R 17 and R 18).
• the refractive index of an optical component containing a cyclic olefin-based copolymer changes and the optical performance deteriorates when exposed to a high temperature environment for a long time. ..
• the present inventors have diligently studied to solve the above problems.
• a cyclic olefin system having the above-mentioned structural unit (c) derived from at least one cyclic olefin represented by the general formula (III), and the content of the above-mentioned structural unit (a) being 50 mol% or less. It has been found that the optical component using the copolymer (A) has a high refractive index, the refractive index does not easily decrease even when exposed to a high temperature environment for a long time, and the optical performance is excellent in long-term reliability.
• the present embodiment it is possible to realize an optical component having a high refractive index and excellent long-term reliability of optical performance in a high temperature environment.
• the lower limit of the content of the cyclic olefin copolymer (A) in the optical component according to the present embodiment is preferably 50% by mass or more, more preferably 70% by mass, when the entire optical component is 100% by mass. Above, it is more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly preferably 95% by mass or more. When the content of the cyclic olefin copolymer (A) in the optical component according to the present embodiment is at least the above lower limit value, the optical performance can be further improved.
• the upper limit of the content of the cyclic olefin copolymer (A) in the optical component according to the present embodiment is not particularly limited, but is, for example, 100% by mass or less.
• the optical component according to this embodiment contains the cyclic olefin copolymer (A), it has excellent optical performance. Therefore, it can be suitably used as an optical component in an optical system that needs to identify an image with high accuracy.
• Optical components are components used in optical system equipment and the like, and specific examples thereof include sensor lenses, pickup lenses, projector lenses, prisms, f ⁇ lenses, imaging lenses, light guide plates, etc., which are lenses used for various sensors. Therefore, from the viewpoint of the effect according to the present embodiment, it can be suitably used for an f ⁇ lens, an imaging lens, a sensor lens, a prism or a light guide plate.
• an optical component containing a cyclic olefin copolymer (A) having a glass transition point in the range of 140 ° C. or higher satisfies moisture heat resistance while having high heat resistance. Therefore, optical components containing the cyclic olefin copolymer (A) having a glass transition point in the range of 140 ° C. or higher have heat resistance of in-vehicle camera lenses and camera lenses for mobile devices (mobile phones, smartphones, tablets, etc.). It can be particularly preferably used for the required optical components.
• the in-vehicle camera lens and the camera lens for a portable device include a view camera lens, a sensing camera lens, a lens for light convergence of a head-up display, and a lens for light diffusion of a head-up display.
• the optical component according to the present embodiment may be combined with a second optical component different from the above optical component.
• the second optical component is not particularly limited, and for example, an optical component composed of at least one resin selected from a polycarbonate resin and a polyester resin can be used.
• the cyclic olefin copolymer (A) has a structural unit (a) derived from at least one olefin represented by the general formula (I) and at least one cyclic represented by the general formula (II). It has a structural unit (b) derived from an olefin and a structural unit (c) derived from at least one cyclic olefin represented by the above general formula (III).
• R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms.
• the olefin monomer for forming the structural unit (a) include ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methyl-1-pentene, 3-methyl-1-pentene, and 3 -Ethyl-1-pentene, 4-methyl-1-pentene, 4-methyl-1-hexene, 4,4-dimethyl-1-hexene, 4,4-dimethyl-1-pentene, 4-ethyl-1-hexene , 3-Ethyl-1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene and the like.
• ethylene or propylene is preferable, and ethylene is particularly preferable, from the viewpoint of obtaining an optical component having more excellent heat resistance, mechanical properties and optical properties.
• One type of olefin monomer for forming the structural unit (a) may be used alone, or two or more types may be used in combination.
• the structural unit (a) when the total content of the structural unit (a), the structural unit (b) and the structural unit (c) is 100 mol%, the structural unit (a)
• the content of is 50 mol% or less, preferably 49 mol% or less, more preferably 48 mol% or less, and preferably 35 mol% or more, more preferably, from the viewpoint of improving the heat resistance of the optical component. It is preferably 40 mol% or more.
• the content of the structural unit (a) can be measured by 13 C-NMR.
• R 1 to R 8 are independently hydrogen atoms, halogen atoms, or hydrocarbon groups having 4 or less carbon atoms.
• the halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
• the hydrocarbon group having 4 or less carbon atoms include an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group and an isobutyl group, and a cycloalkyl group such as a cyclopropyl group.
• R 5 to R 8 may be bonded to each other to form a single ring, and the mono ring may have a double bond, and R 5 and R 6 or R 7 and the same. in the R 8 may form an alkylidene group.
• the single ring formed here is illustrated below.
• the carbon atoms numbered 1 or 2 form an alicyclic structure to which R 5 (R 6 ) or R 7 (R 8) is bonded in the general formula (II). It is a carbon atom.
• R 5 (R 6 ) or R 7 (R 8) is bonded in the general formula (II). It is a carbon atom.
• the alkylidene group include an ethylidene group, a propyridene group, and an isopropylidene group.
• Examples of the cyclic olefin monomer for forming the structural unit (b) include bicyclo [2.2.1] -2-heptene (also referred to as norbornene) and bicyclo [2.2.1] having 11 or less carbon atoms. ] Hept-2-ene derivative, tricyclo [4.3.0.1 2,5 ] -3-decene derivative, tricyclo [4.4.0.1 2,5 ] -3-undecene and the like can be mentioned. Among these, bicyclo [2.2.1] -2-heptene is preferable. As the cyclic olefin monomer for forming the structural unit (b), one type may be used alone, or two or more types may be used in combination.
• the structural unit (b) when the total content of the structural unit (a), the structural unit (b) and the structural unit (c) is 100 mol%, the structural unit (b)
• the content of is preferably 25 mol% or more and 64 mol% or less, and more preferably 30 mol% or more and 60 mol% from the viewpoint of improving the long-term reliability of optical performance in a high temperature environment and the balance between refractive index and heat resistance. Below, it is more preferably 35 mol% or more and 55 mol% or less, and particularly preferably 40 mol% or more and 55 mol% or less.
• the content of the structural unit (b) can be measured by 13 C-NMR.
• n is 0 or 1
• m is 0 or a positive integer
• n + m is a positive integer
• q is 0 or 1.
• Ra and R b independently represent the following atoms or hydrocarbon groups, and when q is 0, the respective bonds are bonded to form a 5-membered ring.
• R 1 to R 18 and Ra and R b are independently hydrogen atoms, halogen atoms or hydrocarbon groups, respectively.
• the halogen atom is the same as the halogen atom in the above general formula (II).
• examples of the hydrocarbon group include an alkyl group having 1 to 20 carbon atoms and a cycloalkyl group having 3 to 15 carbon atoms, respectively. More specifically, examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an amyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group and an octadecyl group, and examples of the cycloalkyl group include a cycloalkyl group. Cyclohexyl groups can be mentioned. These groups may be substituted with halogen atoms.
• R 15 and R 16 are, the R 17 and R 18 are, the R 15 and R 17 are, the R 16 and R 18 are, and the R 15 and R 18, or, R 16 and R 17 may be coupled (jointly with each other) to form a monocyclic or polycyclic, and the monocyclic or polycyclic thus formed has a double bond. You may be doing it.
• the monocyclic or polycyclic ring formed here is exemplified below.
• the carbon atoms numbered 1 or 2 form an alicyclic structure to which R 15 (R 16 ) or R 17 (R 18) is bonded in the general formula (III). It is a carbon atom.
• an alkylidene group may be formed by R 15 and R 16 or by R 17 and R 18.
• Examples of such an alkylidene group usually include an alkylidene group having 2 to 20 carbon atoms, and specific examples thereof include an ethylidene group, a propylidene group and an isopropylidene group.
• Examples of the cyclic olefin monomer for forming the structural unit (c) include tetracyclo [4.4.0.1 2,5 . 17,10 ] -3-dodecene (also called tetracyclododecene), tricyclo [4.3.0.1 2,5 ] -3-decene derivative with 12 or more carbon atoms, tricyclo [4.3.0] .1 2,5 ] -3-Undecene derivative, tetracyclo [4.4.0.1 2,5 . 1 7, 10 ] -3-dodecene derivative, pentacyclo [6.6.1.1 3,6 . 0 2,7 .
• cyclic olefin monomer for forming the structural unit (c) one type may be used alone, or two or more types may be used in combination.
• the structural unit (c) when the total content of the structural unit (a), the structural unit (b) and the structural unit (c) is 100 mol%, the structural unit (c)
• the content of the above is preferably 1 mol% or more and 25 mol% or less, more preferably 3 mol% or more and 20 mol% or less, from the viewpoint of facilitating the maintenance of a high refractive index of the optical component.
• the content of the structural unit (c) can be measured by 13 C-NMR.
• the ratio ((b) / (c)) of the content of the structural unit (b) to the content of the structural unit (c) is 2 or more. It is preferably present, and more preferably 3 or more.
• (b) / (c) is at least the above lower limit value, an optical component having a higher refractive index and a longer-term reliability of optical performance in a high temperature environment can be obtained.
• the upper limit of (b) / (c) is not particularly limited, but is preferably 13 or less, for example.
• the cyclic olefin monomer for forming the structural unit (b) and the cyclic olefin monomer for forming the structural unit (c) are, for example, a Diels-Alder reaction of cyclopentadiene and olefins having a corresponding structure. Manufactured by.
• the cyclic olefin copolymer (A) contains a structural unit derived from another copolymerizable monomer, if necessary, as long as the object of the present invention is not impaired. May be good.
• examples of such other monomers include cyclic olefin monomers for forming the structural unit (b) and cyclic olefins other than the cyclic olefin monomer for forming the structural unit (c), and examples thereof include cyclobutene, cyclopentene, and the like.
• Cyclohexene, 3,4-dimethylcyclohexene, 3-methylcyclohexene, 2- (2-methylbutyl) -1-cyclohexene, 3a, 5,6,7a-tetrahydro-4,7-methano-1H-indene and the like can be mentioned. These may be used alone or in combination. Further, other olefins such as styrene and ⁇ -methylstyrene are also mentioned.
• the cyclic olefin copolymer (A) according to the present embodiment does not substantially contain a gel-like crosslinked polymer and has a substantially linear structure which may have a branched structure. Is preferable. It can be confirmed that the copolymer has a substantially linear structure by dissolving the copolymer in an organic solvent and containing no insoluble matter. For example, when measuring the ultimate viscosity [ ⁇ ] as described later, it can be confirmed by completely dissolving the copolymer in decalin at 135 ° C.
• the cyclic olefin copolymer (A) has a limit viscosity ([ ⁇ ]) measured in decalin at 135 ° C., preferably 0.1 to 2.0 dl / g, more preferably. Is 0.15 to 1.7 dl / g.
• the copolymerization type of the cyclic olefin copolymer (A) according to the present embodiment is not particularly limited, and examples thereof include random copolymers and block copolymers.
• the cyclic olefin copolymer (A) according to the present embodiment from the viewpoint of being excellent in optical properties such as transparency, refractive index and birefringence, and being able to obtain highly accurate optical components. It is preferable to use a random copolymer.
• the structural unit (b) contains a repeating unit derived from bicyclo [2.2.1] -2-heptene, and the cyclic olefin copolymer (A).
• the structural unit (c) in) is tetracyclo [4.4.0.1 2,5 . It is preferable to include repeating units derived from 17 and 10] -3-dodecene.
• Examples of the cyclic olefin copolymer (A) according to the present embodiment include ethylene, bicyclo [2.2.1] -2-heptene, and tetracyclo [4.4.0.1 2,5 .
• a random copolymer with 17 and 10 ] -3-dodecene is preferred.
• one type of cyclic olefin copolymer (A) may be used alone, or two or more types may be used in combination.
• the cyclic olefin copolymer (A) according to the present embodiment is, for example, JP-A-60-168708, JP-A-61-12816, JP-A-61-115912, JP-A-61-
• JP-A-60-168708 JP-A-61-12816, JP-A-61-115912
• JP-A-61- By appropriately selecting the conditions according to the methods of JP-A-115916, JP-A-61-272118, JP-A-61-272216, JP-A-62-252406, JP-A-62-252407, etc. Can be manufactured.
• the glass transition point (Tg) of the cyclic olefin copolymer (A) according to the present embodiment is preferably 140 ° C. or higher, more preferably 143 ° C. or higher, and even more preferably 145 ° C. or higher. , 150 ° C. or higher is even more preferable.
• the glass transition point (Tg) of the cyclic olefin copolymer (A) is within the above range, it is even better when used as an optical component that requires heat resistance, such as an in-vehicle camera lens or a camera lens for a portable device. Heat resistance can be obtained.
• the upper limit of the glass transition point (Tg) of the cyclic olefin copolymer (A) according to the present embodiment is not particularly limited, but from the viewpoint of moldability, 180 ° C. or lower is preferable, and 170 ° C. or lower is more preferable.
• the glass transition point (Tg) of the cyclic olefin copolymer (A) according to the present embodiment can be measured using a differential scanning calorimeter (DSC).
• DSC differential scanning calorimeter
• the optical component according to the present embodiment contains an additive known as an optional component as an optional component within a range that does not impair the good physical characteristics of the optical component according to the present embodiment. Can be done.
• Additives include, for example, hydrophilic stabilizers, hydrophilic agents, antioxidants, secondary antioxidants, lubricants, mold release agents, antifogging agents, weatherproof stabilizers, light stabilizers, UV absorbers, antistatic agents.
• the hydrophilic stabilizer is preferably a fatty acid ester of a fatty acid and a polyhydric alcohol. Fatty acid esters with fatty acids and polyhydric alcohols having one or more ether groups are more preferred.
• the optical component according to the present embodiment can be produced by molding a cyclic olefin resin composition containing the cyclic olefin copolymer (A) into a predetermined shape.
• the method for obtaining the optical component by molding the cyclic olefin resin composition is not particularly limited, and a known method can be used.
• extrusion molding, injection molding, inflation molding, blow molding, extrusion blow molding, injection blow molding, press molding, vacuum molding, powder slush molding, calendar molding, foam molding and the like can be applied. Is. Among these, the injection molding method is preferable from the viewpoint of moldability and productivity.
• the molding conditions are appropriately selected depending on the purpose of use or the molding method.
• the resin temperature in injection molding is usually 150 ° C. to 400 ° C., preferably 200 ° C. to 350 ° C., more preferably 230 ° C. to 330 ° C. It is appropriately selected in the range.
• the cyclic olefin copolymer (A) and other components added as necessary are mixed with a known kneading device such as an extruder and a Banbury mixer.
• a known kneading device such as an extruder and a Banbury mixer.
• Method of melting and kneading a method of dissolving the cyclic olefin copolymer (A) and other components added as necessary in a common solvent and then evaporating the solvent; a cyclic olefin copolymer in a poor solvent. It can be obtained by a method of adding and precipitating a solution of the coalescence (A) and other components added as needed;
• the decalcified polymerization solution was added to a beaker containing about 4 times the volume of acetone with respect to the polymerization solution under stirring to precipitate a copolymer, and the precipitated copolymer was separated from the filtrate by filtration.
• the obtained polymer containing the solvent was dried under reduced pressure at 130 ° C. for 10 hours, 2.72 g of a white powdery ethylene / tetracyclododecene / norbornene copolymer was obtained. From the above, a cyclic olefin copolymer (P-1) was obtained.
• Glass transition point (Tg) The glass transition point (Tg) of the cyclic olefin copolymer was measured under an N 2 (nitrogen) atmosphere using DSC-6220 manufactured by Shimadzu Science Co., Ltd. The cyclic olefin copolymer was heated from room temperature to 200 ° C. at a heating rate of 10 ° C./min and then held for 5 minutes, and then cooled to ⁇ 20 ° C. at a temperature decreasing rate of 10 ° C./min and then held for 5 minutes. .. Then, the glass transition point (Tg) of the cyclic olefin copolymer was determined from the endothermic curve when the temperature was raised to 200 ° C. at a heating rate of 10 ° C./min.
• Example 1 Using an injection molding machine (ROBOSHOT ⁇ -S30iA manufactured by FANUC), a cyclic olefin resin (P-1) is injection-molded under the conditions of a cylinder temperature of 275 ° C. and a mold temperature of 125 ° C., and 65 mm ⁇ 35 mm ⁇ thickness 3 mmt. The injection-molded sheet of was produced. Each of the following evaluations was performed on the obtained injection-molded sheet. The results obtained are shown in Table 1.
• Refractive index The refractive index (refractive index) of an injection-molded sheet of 30 mm ⁇ 30 mm ⁇ thickness 2.0 mm molded with a microcompound according to ASTM D542 using a refractive index meter (KPR200 manufactured by Shimadzu Science Co., Ltd.) at a wavelength of 589 nm. nd) was measured.
• the refractive index (nd) of the injection-molded sheet at a wavelength of 589 nm was measured before and after the heat resistance test described below.
• Examples 2 to 8 and Comparative Examples 1 to 4 An injection molded sheet was prepared in the same manner as in Example 1 except that the type of the cyclic olefin copolymer was changed to the polymer shown in Table 1, and the heat resistance test temperature in the heat resistance test was set to the temperature shown in Table 1. Was evaluated in the same manner as in Example 1. The results obtained are shown in Table 1, respectively.

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