Cyclic olefin copolymer, cyclic olefin copolymer composition, molded article, and optical component

Abstract

The present invention provides a cyclic olefin copolymer which comprises a constituent unit (A) that is derived from an olefin monomer represented by formula (1) and a constituent unit (B) that is derived from at least one cyclic olefin monomer selected from the group consisting of a cyclic olefin monomer represented by formula (2) and a cyclic olefin monomer represented by formula (3), wherein: if the total content of the constituent unit (A) and the constituent unit (B) in the cyclic olefin copolymer is taken as 100% by mole, the content of the constituent unit (A) is 40% by mole to 70% by mole and the content of the constituent unit (B) is 30% by mole to 60% by mole; the weight average molecular weight (Mw) as determined by gel permeation chromatography (GPC) is 50,000 to 500,000; and the glass transition temperature (Tg) is 150°C or higher.

Description

[Technical Field]

[0001] The present invention relates to a cyclic olefin copolymer, a cyclic olefin copolymer composition, a molded article, and an optical component. [Background technology]

[0002] Glass is widely used as a material for optical components because it has the characteristics of high transparency, high refractive index, and extremely low birefringence. However, glass has drawbacks such as poor moldability and difficulty in reducing its weight, so recently polymeric materials, which are lightweight and have excellent moldability, have come to be used as materials for optical components. Examples of such polymeric materials include polymethyl methacrylate (PMMA) and polycarbonate (PC).

[0003] On the other hand, PMMA is preferable in that it has good transparency and low birefringence, but has the drawback of low heat resistance, prone to deformation such as warping after molding, and poor shape stability. Furthermore, while PC has a better refractive index and heat resistance than PMMA, it has the disadvantage of high birefringence. In optical components, high birefringence causes large aberrations, which causes abnormalities in the shape of the focused spot and reduces pickup performance.

[0004] Here, cyclic olefin copolymers have attracted attention as materials with low birefringence, and are used in optical lenses such as imaging lenses, fθ lenses, pickup lenses, etc. In particular, cyclic olefin copolymers used in optical lenses for head-mounted displays and the like are required to further reduce the influence of birefringence, since light passes through the same lens multiple times due to its design. As technologies relating to such cyclic olefin copolymers, there are, for example, inventions described in Patent Documents 1 to 3.

[0005] Patent Document 1 discloses a method for producing optical components, the method including: a step of molding an optical component molded body made of a resin (A) into a mold; a first heat treatment step of heat-treating the optical component molded body removed from the mold; a slow cooling step of slow cooling the optical component molded body after the first heat treatment step; and a second heat treatment step of further heat-treating the optical component molded body after the slow cooling step, wherein when the glass transition temperature of the resin (A) is Tg [°C], the heating temperature in the first heat treatment step is T1 [°C], and the heating temperature in the second heat treatment step is T2 [°C], the method for producing optical components satisfies the relationships Tg-15≦T1≦Tg-2 and T2≦Tg-20, and discloses that optical components with low birefringence can be obtained.

[0006] Patent Document 2 discloses that a retardation film made of an amorphous polyolefin copolymer (a) comprising ethylene units and norbornene units, (b) the norbornene units contain a double-chain moiety, the stereoregularity of the double-chain moiety is meso-type and racemo-type, the ratio of meso-type double-chain moiety / racemo-type double-chain moiety being 4 or more, and (c) having a glass transition temperature in the range of 100 to 180°C, has high moisture resistance and good dimensional stability, and can be incorporated into, for example, a liquid crystal display device and effectively used to improve the display quality of the liquid crystal, such as by improving the viewing angle, contrast, and color compensation.

[0007] Patent Document 3 discloses that a retardation film obtained by stretching a cyclic olefin copolymer containing a repeating unit derived from ethylene and a norbornene repeating unit, having a molecular weight distribution Mw / Mn in the range of 3.0 to 1.0 and a glass transition temperature in the range of 110°C to 175°C, has excellent birefringence, in-plane retardation and transparency. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Japanese Patent Publication No. 2020-185742 [Patent Document 2] International Publication No. 2006 / 030797 [Patent Document 3] Japanese Patent Application Laid-Open No. 2017-58487 Summary of the Invention [Problem to be solved by the invention]

[0009] For applications in optical components that require miniaturization and thinning, cyclic olefin copolymers are required to have a further reduction in birefringence while maintaining good moldability. According to the investigations of the present inventors, it has become clear that the inventions described in Patent Documents 1 to 3 have room for improvement in terms of the balance of moldability and low birefringence.

[0010] The present invention has been made in view of the above circumstances, and provides a cyclic olefin copolymer and a cyclic olefin copolymer composition which are capable of realizing a molded article having good moldability and low birefringence, as well as a molded article and an optical component having good moldability and low birefringence. [Means for solving the problem]

[0011] The present inventors have conducted extensive research to solve the above problems, and as a result have found that the balance of the moldability and low birefringence properties of a cyclic olefin copolymer can be improved by adjusting the ratio of olefin monomer-derived structural units and cyclic olefin monomer-derived structural units constituting the cyclic olefin copolymer and the weight-average molecular weight (Mw) within specific ranges, thereby completing the present invention. According to the present invention, there are provided the following cyclic olefin copolymer, cyclic olefin copolymer composition, molded article, and optical component.

[0012] [1] A structural unit (A) derived from an olefin monomer represented by the following formula (1), A structural unit (B) derived from at least one cyclic olefin monomer selected from the group consisting of a cyclic olefin monomer represented by the following formula (2) and a cyclic olefin monomer represented by the following formula (3), A cyclic olefin copolymer comprising: When the total content of the structural unit (A) and the structural unit (B) in the cyclic olefin copolymer is taken as 100 mol %, the content of the structural unit (A) is 40 mol % or more and 70 mol % or less, and the content of the structural unit (B) is 30 mol % or more and 60 mol % or less, The weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) is 50,000 or more and 500,000 or less, A cyclic olefin copolymer with a glass transition temperature (Tg) of 150°C or higher. [ka] (In the formula (1), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 28 carbon atoms. [ka] (In the formula (2), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, and R 61 ~R 78 and R a1 and R b1 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group; R 75 ~R 78 may be bonded to each other to form a monocyclic or polycyclic ring, and the monocyclic or polycyclic ring may have a double bond; R 75 and R 76 With or R 77 and R 78 and may form an alkylidene group.) [ka] (In the formula (3), x and d are integers of 0 or 1 or more, y and z are 0, 1, or 2, and R 81 ~R 99 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group; R 89 and R 90and the carbon atom to which R is bonded. 93 or the carbon atom to which R 91 may be bonded directly or via an alkylene group having 1 to 3 carbon atoms, and when y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic or polycyclic aromatic ring. [2] The weight average molecular weight (Mw) is 50,000 or more and 150,000 or less, The cyclic olefin copolymer according to [1], wherein the glass transition temperature (Tg) is 150°C or higher and 190°C or lower. [3] The cyclic olefin copolymer according to [1] or [2], which has a glass transition temperature (Tg) of 165°C or higher. [4] The cyclic olefin copolymer according to any one of [1] to [3], which has a molecular weight distribution (Mw / Mn) of 2.20 or more and 2.50 or less. [5] The cyclic olefin copolymer according to any one of [1] to [4], which has an intrinsic viscosity η [dl / g] (in decalin at 135° C.) of 0.60 dl / g or less. [6] The cyclic olefin copolymer according to any one of [1] to [5], wherein the cyclic olefin monomer constituting the structural unit (B) comprises at least one cyclic olefin monomer selected from the group consisting of tetracyclododecene, norbornene, and derivatives thereof. [7] The cyclic olefin copolymer according to any one of [1] to [6], wherein the olefin monomer constituting the structural unit (A) contains ethylene. [8] The cyclic olefin copolymer according to any one of [1] to [7], wherein when a press-molded body having a thickness of 0.1 mm is produced from the cyclic olefin copolymer and then uniaxially stretched, the birefringence of the uniaxially stretched press-molded body is 10 nm or less. [9] A cyclic olefin copolymer composition comprising the cyclic olefin copolymer according to any one of [1] to [8].

[10] The cyclic olefin copolymer according to any one of [1] to [8] or the cyclic olefin copolymer composition according to [9], which can be used for optical parts.

[11] A molded article comprising the cyclic olefin copolymer according to any one of [1] to [8] or the cyclic olefin copolymer composition according to [9] or

[10] .

[12] An optical component comprising the molded article according to

[11] .

[13] The optical component according to

[12] , which is a lens for a head-mounted display.

[14] Use of the optical component according to

[12] for a lens for a head-mounted display. [Effects of the Invention]

[0013] According to the present invention, it is possible to provide a cyclic olefin copolymer and a cyclic olefin copolymer composition which have good moldability and can realize a molded article with low birefringence, as well as a molded article and an optical component which have good moldability and low birefringence. DETAILED DESCRIPTION OF THE INVENTION

[0014] Hereinafter, the present invention will be described based on the embodiments. In the present embodiments, "A to B" indicating a numerical range means A or more and B or less unless otherwise specified. Furthermore, each of the monomers constituting the cyclic olefin copolymer of the present invention may be a monomer obtained from a fossil raw material, or may be a monomer obtained from an animal or plant raw material.

[0015] [Cyclic olefin copolymer] The cyclic olefin copolymer of the present invention is a cyclic olefin copolymer comprising a structural unit (A) derived from an olefin monomer represented by the following formula (1) and a structural unit (B) derived from at least one cyclic olefin monomer selected from the group consisting of a cyclic olefin monomer represented by the following formula (2) and a cyclic olefin monomer represented by the following formula (3), wherein, when the total content of the structural units (A) and (B) in the cyclic olefin copolymer is taken as 100 mol %, the content of the structural unit (A) is from 40 mol % to 70 mol % and the content of the structural unit (B) is from 30 mol % to 60 mol %, the weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) is from 50,000 to 500,000, and the glass transition temperature (Tg) is 150°C or higher.

[0016] [ka] In the formula (1), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 28 carbon atoms.

[0017] [ka] In the formula (2), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, and R 61 ~R 78 and R a1 and R b1 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group; R 75 ~R 78 may be bonded to each other to form a monocyclic or polycyclic ring, and the monocyclic or polycyclic ring may have a double bond; R 75 and R 76 With or R 77 and R 78 may form an alkylidene group.

[0018] [ka] In the formula (3), x and d are integers of 0 or 1 or more, y and z are 0, 1, or 2, and R 81 ~R 99 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group; R 89 and R 90 and the carbon atom to which R is bonded. 93 or the carbon atom to which R 91 may be bonded directly or via an alkylene group having 1 to 3 carbon atoms, and when y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic or polycyclic aromatic ring.

[0019] The cyclic olefin copolymer of the present invention has good moldability and can realize molded articles with low birefringence.

[0020] The reason why such an effect is obtained is presumed to be as follows. The birefringence of the cyclic olefin copolymer according to the present invention is believed to depend on the anisotropy of polarizability derived from each primary structure. Therefore, by copolymerizing the monomers of the structural unit (A) having positive birefringence and the structural unit (B) having negative birefringence at an appropriate composition ratio, it is believed that the positive and negative birefringence can be offset within the polymer molecule, thereby obtaining a cyclic olefin copolymer with low birefringence that is less likely to generate birefringence. On the other hand, as the content of the structural unit (B) increases, the glass transition temperature Tg of the cyclic olefin copolymer increases, and moldability tends to decrease. Therefore, by adjusting the weight average molecular weight (Mw) of the cyclic olefin copolymer according to the present invention to an appropriate range, the decrease in moldability can be suppressed. For the above reasons, it is believed that the cyclic olefin copolymer according to the present invention has good moldability and can give a molded article with low birefringence.

[0021] The olefin monomer, which is one of the copolymerization raw materials for the cyclic olefin copolymer according to the present invention, undergoes addition polymerization to form the structural unit (A), and an example thereof is the olefin monomer represented by the formula (1).

[0022] In the formula (1), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 28 carbon atoms. Examples of the olefin monomer represented by formula (1) include at least one selected from the group consisting of ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methyl-1-butene, 3-methyl-1-pentene, 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, and 1-eicosene. Among these, from the viewpoint of obtaining optical components having better heat resistance, mechanical properties, and optical properties, at least one selected from the group consisting of ethylene and propylene is preferred, and ethylene is more preferred.

[0023] The content of the structural unit (A) in the cyclic olefin copolymer according to the present invention, when the total content of the structural unit (A) and the structural unit (B) in the cyclic olefin copolymer is taken as 100 mol%, is 40 mol% or more, preferably 45 mol% or more, more preferably 50 mol% or more, and even more preferably 54 mol% or more, from the viewpoint of improving the performance balance between moldability and low birefringence, and from the same viewpoint is 70 mol% or less, preferably 65 mol% or less, more preferably 62 mol% or less, even more preferably 60 mol% or less, and even more preferably 58 mol% or less. The content of the structural unit (A) derived from the olefin monomer represented by the formula (1) is 13 It can be measured by C-NMR.

[0024] The cyclic olefin monomer, which is one of the copolymerization raw materials for the cyclic olefin copolymer according to the present invention, undergoes addition polymerization to form the structural unit (B), and examples thereof include the cyclic olefin monomer represented by the formula (2) and the cyclic olefin monomer represented by the formula (3).

[0025] In formula (2), u is 0 or 1, and is preferably 0. v is 0 or a positive integer, preferably an integer of 0 or more and 2 or less, more preferably 0 or 1, and even more preferably 1. w is 0 or 1, preferably 1. R 61 ~R 78 and R a1 and R b1 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group, preferably selected from the group consisting of a hydrogen atom and a hydrocarbon group, and more preferably a hydrogen atom. Examples of the hydrocarbon group include an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, and an aromatic hydrocarbon group having 6 to 20 carbon atoms, among which an alkyl group having 1 to 4 carbon atoms is preferred, a methyl group or an ethyl group is more preferred, and a methyl group is even more preferred. R 75 ~R 78 may be bonded to each other to form a monocyclic or polycyclic ring, and the monocyclic or polycyclic ring may have a double bond; R 75 and R 76 With or R 77 and R 78 may form an alkylidene group.

[0026] In the formula (3), x and d are integers of 0 or 1 or more, preferably 0 or 1, and more preferably 1. y and z are 0, 1 or 2, preferably 0 or 1, and more preferably 0. R 81 ~R 99are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group, preferably selected from the group consisting of a hydrogen atom and a hydrocarbon group, and more preferably a hydrogen atom. Examples of the hydrocarbon group include an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, and an aromatic hydrocarbon group having 6 to 20 carbon atoms, among which an alkyl group having 1 to 4 carbon atoms is preferred, a methyl group or an ethyl group is more preferred, and a methyl group is even more preferred. R 89 and R 90 and the carbon atom to which R is bonded. 93 or the carbon atom to which R 91 may be bonded directly or via an alkylene group having 1 to 3 carbon atoms, and when y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic or polycyclic aromatic ring.

[0027] Specific examples of the cyclic olefin monomer represented by the formula (2) or (3) include the compounds described in paragraphs 0037 to 0063 of WO 2006 / 118261.

[0028] Among the cyclic olefin monomers represented by the formula (2) or (3), the cyclic olefin monomer represented by the formula (2) is preferred. As the cyclic olefin monomer represented by the formula (2), from the viewpoint of further improving the balance of moldability and low birefringence, a tetracyclo[4.4.0.1 2,5 .1 7,10

[0033] The cyclohexene is at least one selected from the group consisting of tetracyclododecene, bicyclo[2.2.1]-3-dodecene (also referred to as "tetracyclododecene" in this specification), bicyclo[2.2.1]-2-heptene (also referred to as "norbornene" in this specification), and derivatives thereof, more preferably at least one selected from the group consisting of tetracyclododecene and norbornene, and even more preferably tetracyclododecene.

[0029] The content of the structural unit (B) in the cyclic olefin copolymer according to the present invention, when the total content of the structural unit (A) and the structural unit (B) in the cyclic olefin copolymer is taken as 100 mol%, is 30 mol% or more, preferably 35 mol% or more, more preferably 38 mol% or more, even more preferably 40 mol% or more, and even more preferably 42 mol% or more, from the viewpoint of improving the performance balance between moldability and low birefringence, and from the same viewpoint is 60 mol% or less, preferably 55 mol% or less, more preferably 50 mol% or less, and even more preferably 46 mol% or less. The content of the structural unit (B) derived from the cyclic olefin monomer represented by the formula (2) or (3) is 13 It can be measured by C-NMR.

[0030] Examples of the copolymer type of the cyclic olefin copolymer according to the present invention include random copolymers, block copolymers, etc. From the viewpoint of further improving the balance of performance such as moldability, low birefringence, transparency, and refractive index, the copolymer type of the cyclic olefin copolymer according to the present invention is preferably a random copolymer.

[0031] The cyclic olefin copolymer according to the present invention is a copolymer of ethylene and tetracyclo[4.4.0.1] from the viewpoint of further improving the balance of properties such as moldability, low birefringence, transparency, and refractive index. 2,5 .1 7,10 At least one selected from the group consisting of a random copolymer of ethylene and bicyclo[2.2.1]-3-dodecene and a random copolymer of ethylene and bicyclo[2.2.1]-2-heptene is preferred, and a random copolymer of ethylene and tetracyclo[4.4.0.1]-3-dodecene is preferred. 2,5 .1 7,10 A random copolymer with ]-3-dodecene is more preferred.

[0032] The total content of the structural unit (A) and the structural unit (B) in the cyclic olefin copolymer according to the present invention, when the total content of all structural units in the cyclic olefin copolymer is taken as 100 mol%, is preferably 80 mol% or more, more preferably 90 mol% or more, even more preferably 95 mol% or more, even more preferably 97 mol% or more, even more preferably 98 mol% or more, and even more preferably 99 mol% or more, from the viewpoint of further improving the performance balance between moldability and low birefringence, and from the same viewpoint, is preferably 100 mol% or less.

[0033] The cyclic olefin copolymer according to the present invention may be used alone or in combination of two or more.

[0034] The cyclic olefin copolymer according to the present invention can be produced by appropriately selecting the conditions according to the methods described in, for example, JP-A-60-168708, JP-A-61-120816, JP-A-61-115912, JP-A-61-115916, JP-A-61-271308, JP-A-61-272216, JP-A-62-252406, JP-A-62-252407, JP-A-2018-145349, International Public Relations 2015 / 122415, JP-A-2007-063409, JP-A-2-173112, etc.

[0035] The cyclic olefin copolymer according to the present invention is preferably produced using a predetermined catalyst, since it is easier to adjust the content of the structural unit (A) and the content of the structural unit (B) more preferably. Examples of the catalyst include half-metallocene titanium compounds, half-metallocene zirconium compounds, half-metallocene hafnium compounds, metallocene titanium compounds, metallocene zirconium compounds, and metallocene hafnium compounds. Among these, one or more compounds selected from the group consisting of half-metallocene titanium compounds having at least one of a cyclopentadienyl group and a pyrazolate group, half-metallocene zirconium compounds having at least one of a cyclopentadienyl group and a pyrazolate group, half-metallocene hafnium compounds having at least one of a cyclopentadienyl group and a pyrazolate group, metallocene titanium compounds having fluorene, metallocene zirconium compounds having fluorene, and metallocene hafnium compounds having fluorene are preferred. These catalysts can be produced by appropriately selecting conditions according to the methods described in, for example, JP-A-2018-150273 and JP-A-2019-172954.

[0036] The glass transition temperature (Tg) of the cyclic olefin copolymer according to the present invention is, from the viewpoint of improving the balance of moldability, low birefringence, and heat resistance, 150°C or higher, preferably 155°C or higher, more preferably 160°C or higher, even more preferably 165°C or higher, even more preferably 170°C or higher, even more preferably 175°C or higher, and even more preferably 180°C or higher; from the same viewpoint, it is preferably 250°C or lower, more preferably 230°C or lower, even more preferably 200°C or lower, and even more preferably 190°C or lower.

[0037] The glass transition temperature (Tg) of the cyclic olefin copolymer according to the present invention can be measured by a differential scanning calorimeter (DSC). Specific measurement conditions include, for example, using a DSC-7020 manufactured by Hitachi High-Tech Science Corporation, raising the temperature from room temperature to 250°C at a heating rate of 10°C / min under a nitrogen atmosphere, maintaining the temperature for 5 minutes, and then lowering the temperature to -20°C at a heating rate of 10°C / min, maintaining the temperature for 5 minutes. The glass transition temperature (Tg) of the cyclic olefin copolymer can be determined from the endothermic curve obtained when the temperature is raised to 300°C at a heating rate of 10°C / min.

[0038] The intrinsic viscosity η [dl / g] (in decalin at 135°C) of the cyclic olefin copolymer according to the present invention is preferably 0.20 dl / g or more, more preferably 0.23 dl / g or more, even more preferably 0.30 dl / g or more, even more preferably 0.35 dl / g or more, and even more preferably 0.40 dl / g or more, from the viewpoint of further improving the performance balance between moldability and low birefringence, and from the same viewpoint, is preferably 0.75 dl / g or less, more preferably 0.70 dl / g or less, even more preferably 0.60 dl / g or less, even more preferably 0.55 dl / g or less, and even more preferably 0.50 dl / g or less. The intrinsic viscosity η [dl / g] of the cyclic olefin copolymer according to the present invention can be measured in accordance with ASTM J1601, specifically by the method described in the examples.

[0039] The weight average molecular weight (Mw) of the cyclic olefin copolymer according to the present invention, as measured by gel permeation chromatography (GPC), is 50,000 or more, preferably 70,000 or more, more preferably 80,000 or more, even more preferably 90,000 or more, even more preferably 100,000 or more, and even more preferably 110,000 or more, from the viewpoint of further improving the balance of moldability and low birefringence, and from the same viewpoint, is 500,000 or less, preferably 300,000 or less, more preferably 200,000 or less, even more preferably 150,000 or less, even more preferably 130,000 or less, and even more preferably 120,000 or less. In particular, when the Mw of the cyclic olefin copolymer is 150,000 or less, fish eyes are less likely to occur during film formation and the flowability during injection molding is improved, making it suitable for thin injection molding.Furthermore, birefringence is further suppressed, making it more suitable for optical applications, which is more preferable. The weight average molecular weight (Mw) of the cyclic olefin copolymer according to the present invention can be specifically measured by the method described in the examples.

[0040] The molecular weight distribution (Mw / Mn) of the cyclic olefin copolymer according to the present invention is preferably 2.20 or more, more preferably 2.25 or more, even more preferably 2.30 or more, and still more preferably 2.35 or more, from the viewpoint of further improving the balance of moldability and low birefringence, and from the same viewpoint, is preferably 2.50 or less. The number average molecular weight (Mn) of the cyclic olefin copolymer according to the present invention can be specifically measured by the method described in the examples.

[0041] In the case of the cyclic olefin copolymer according to the present invention, from the viewpoint of adjusting the birefringence of the obtained molded article to a more suitable range, when a press-molded article having a thickness of 0.1 mm is produced from the cyclic olefin copolymer according to the present invention and uniaxially stretched, the birefringence of the press-molded article is preferably 10 nm or less, more preferably 8 nm or less, even more preferably 5 nm or less, even more preferably 3.5 nm or less, even more preferably 3 nm or less, even more preferably 1 nm or less, and even more preferably 0.5 nm or less. In this specification, the birefringence of an injection-molded article is the average value (nm) of the phase difference measured at 20 to 35 mm from the gate direction using, for example, a KOBRA CCD manufactured by Oji Scientific Instruments at a measurement wavelength of 650 nm. A 0.1 mm thick press-molded product made of a cyclic olefin copolymer can be obtained, for example, by sandwiching the cyclic olefin copolymer between ultra-heat-resistant polyimide films and vacuum-pressing the cyclic olefin copolymer using a 0.1 mm spacer at 260°C, 10 MPa, and 3 minutes. The uniaxial stretching can be performed at a stretching temperature of Tg + 5°C of the cyclic olefin copolymer and a stretching rate of 3% / min, with a stretching ratio of 1.5 in the uniaxial direction.

[0042] [Cyclic olefin copolymer composition] The cyclic olefin copolymer composition according to the present invention contains the cyclic olefin copolymer according to the present invention described above, and, if necessary, contains other components other than the cyclic olefin copolymer according to the present invention. In this specification, the cyclic olefin copolymer composition according to the present invention is also called a cyclic olefin copolymer composition when it contains only the cyclic olefin copolymer.

[0043] Furthermore, from the viewpoint of further improving the balance of moldability and low birefringence, the content of the cyclic olefin copolymer according to the present invention in the cyclic olefin copolymer composition according to the present invention is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, and even more preferably 98% by mass or more, when the entire cyclic olefin copolymer composition is taken as 100% by mass.

[0044] Examples of other components include resins other than the cyclic olefin copolymer according to the present invention, hydrophilic agents, light stabilizers, heat stabilizers, antioxidants, metal deactivators, hydrochloric acid absorbers, antistatic agents, flame retardants, slip agents, antiblocking agents, antifogging agents, lubricants, natural oils, synthetic oils, waxes, organic or inorganic fillers, secondary antioxidants, mold release agents, etc. Other components can be blended in an amount appropriate to the extent that the object of the present invention is not impaired.

[0045] The cyclic olefin copolymer composition according to the present invention can be obtained by a method of melt-kneading the cyclic olefin copolymer according to the present invention and other components using a known kneading device such as an extruder or a Banbury mixer; a method of dissolving the cyclic olefin copolymer according to the present invention and other components in a common solvent and then evaporating the solvent; or a method of adding a solution of the cyclic olefin copolymer according to the present invention and other components to a poor solvent to cause precipitation.

[0046] [Molded bodies and optical components] The molded article according to the present invention is a molded article containing the above-mentioned cyclic olefin copolymer according to the present invention or the cyclic olefin copolymer composition according to the present invention. The molded article according to the present invention contains the cyclic olefin copolymer according to the present invention, and therefore has a good balance of heat resistance, optical properties (transparency, haze, etc.), chemical resistance, low moisture absorption, etc., and also has an improved performance balance of moldability and low birefringence.

[0047] The molded article according to the present invention contains the cyclic olefin copolymer according to the present invention, and therefore has excellent optical properties such as low birefringence, etc. Therefore, it can be suitably used as an optical component in an optical system that requires highly accurate image identification. Optical components are components used in optical devices and the like, and specific examples include lenses for various sensors, pickup lenses, projector lenses, prisms, fθ lenses, imaging lenses, camera lenses, light guide plates, and lenses for head-mounted displays. From the viewpoint of the effects of the present invention, the optical components can be particularly suitably used for fθ lenses, imaging lenses, sensor lenses, prisms, light guide plates, and lenses for head-mounted displays.

[0048] Furthermore, from the viewpoint of further improving the balance of moldability and low birefringence, the content of the cyclic olefin copolymer according to the present invention in the molded article according to the present invention is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, and even more preferably 98% by mass or more, when the entire molded article is taken as 100% by mass.

[0049] The method for molding the cyclic olefin copolymer according to the present invention or the cyclic olefin copolymer composition according to the present invention to obtain a molded article is not particularly limited, and known methods can be used. Depending on the application and shape, for example, extrusion molding, injection molding, compression molding, inflation molding, blow molding, extrusion blow molding, injection blow molding, press molding, vacuum molding, powder slush molding, calendar molding, foam molding, etc. can be applied. Among these, injection molding and extrusion molding are preferred from the viewpoint of moldability and productivity, and injection molding is more preferred. Furthermore, molding conditions are appropriately selected depending on the intended use or molding method. For example, the resin temperature in injection molding is appropriately selected from the range of, for example, 150°C to 400°C, preferably 200°C to 350°C, and more preferably 230°C to 330°C.

[0050] Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various other configurations can also be adopted. Furthermore, the present invention is not limited to the above-described embodiment, and modifications and improvements within the scope of achieving the object of the present invention are included in the present invention. [Example]

[0051] The present embodiment will be described in detail below with reference to examples, etc. However, the present embodiment is not limited to the descriptions of these examples.

[0052] First, the measurement and evaluation methods used in the examples and comparative examples will be described.

[0053] [Method for measuring the content of each structural unit constituting a cyclic olefin copolymer] Ethylene and tetracyclo[4.4.0.1 2,5 .1 7,10 The content of ]-3-dodecene was measured using an AVANCE IIIcryo-500 nuclear magnetic resonance spectrometer manufactured by Bruker Biospin under the following conditions. Solvent: deuterated tetrachloroethane Sample concentration: 10 w / v% Pulse repetition time: 12 seconds Accumulation count: 256 times Measurement temperature: 120℃ Measured under the above conditions 13 The contents of ethylene and tetracyclododecene were quantified by C-NMR spectroscopy.

[0054] [Intrinsic viscosity [η]] Using a migration viscometer (Rigo Co., Ltd., Model VNR053U), 0.25 to 0.30 g of cyclic olefin copolymer was dissolved in 25 ml of decalin to prepare a sample. The specific viscosity of the cyclic olefin copolymer was measured at 135°C in accordance with ASTM J1601, and the ratio of this to the concentration was extrapolated to a concentration of 0 to determine the intrinsic viscosity [η] of the cyclic olefin copolymer.

[0055] [Glass transition temperature (Tg)] The glass transition temperature (Tg) of the cyclic olefin copolymer was measured under a nitrogen atmosphere using a DSC-7020 manufactured by Hitachi High-Tech Science Corporation. The cyclic olefin copolymer was heated from room temperature to 250°C at a heating rate of 10°C / min and then held for 5 minutes. The temperature was then lowered to -20°C at a heating rate of 10°C / min and then held for 5 minutes. The glass transition temperature (Tg) of the cyclic olefin copolymer was then determined from the endothermic curve when the temperature was raised to 300°C at a heating rate of 10°C / min.

[0056] [Weight average molecular weight (Mw), molecular weight distribution (Mw / Mn)] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the cyclic olefin copolymer were determined by gel permeation chromatography (GPC) using a Waters Alliance GPC 2000 gel permeation chromatograph (high-temperature size exclusion chromatograph) under the following operating conditions: <Devices and conditions used> Measurement equipment: Gel permeation chromatograph Alliance GPC2000 (Waters) Analysis software: Chromatography Data System Empower (trademark, Waters) Column: TSKgel GMH6-HT x 2 + TSKgel GMH6-HT x 2 (inner diameter 7.5 mm x length 30 cm, Tosoh Corporation) Mobile phase: o-dichlorobenzene (=ODCB) (Wako Pure Chemical Industries, Ltd., special grade reagent) Detector: Differential refractometer (built into the device) Column temperature: 140℃ Flow rate: 1.0mL / min Injection volume: 400μL Sampling time interval: 1 second Sample concentration: 0.15% (w / v) Molecular weight calibration: Monodisperse polystyrene (Tosoh Corporation) / molecular weight 495 to 20.6 million

[0057] [Moldability] The cyclic olefin copolymers obtained in the examples and comparative examples were sandwiched between ultra-heat-resistant polyimide films (product name: Upilex, manufactured by Ube Industries, Ltd.) and vacuum-press molded using a 0.1 mm spacer at 260°C, 10 MPa, and 3 minutes. The resulting films were then stretched uniaxially by 1.5 times using an AG-XP (Shimasen Seisakusho) at a stretching temperature of Tg + 5°C of the cyclic olefin copolymer and a stretching rate of 3% / min. After stretching, the films were removed and immersed in ice water for 3 minutes to obtain films for birefringence measurement. Next, the obtained film for birefringence measurement was observed, and the moldability of the cyclic olefin copolymer was evaluated according to the following criteria. A: No visible cracks and 80% or more of the film maintains its shape B: Cracks are visible, but 70% or more of the film maintains its shape C: Cracks are visually observed, and more than 30% but less than 70% of the film does not maintain its shape. D: Cracks are visually observed and 70% or more of the film does not maintain its shape.

[0058] [Birefringence] For the birefringence measurement film obtained above, measuring 80 mm x 15 mm x 0.08 mm thick, the average value (nm) of the phase difference from 20 to 35 mm from the gate direction was determined as birefringence using a KOBRA CCD manufactured by Oji Scientific Instruments at a measurement wavelength of 650 nm.

[0059] Example 1 In a 2.0 L glass reactor that had been thoroughly purged with nitrogen, 900 mL of a 9:1 mixture of cyclohexane and hexane and tetracyclo[4.4.0.1 2,5 .1 7,10 16.2 g of tetracyclododecene (hereinafter simply referred to as "tetracyclododecene"; Mw: 160.2 (g / mol)) was charged, and the liquid and gas phases were saturated with ethylene at 150 L / hr and hydrogen at 0.24 L / hr. 0.9 mmol of MMAO (modified methylaluminoxane) was added. 0.003 mmol of 3,5-bismethylethyl-1-pyrazolate-t-butylcyclopentadienyltitanium dichloride (hereinafter referred to as titanium compound (1); synthesized with reference to JP 2018-150273 A) was then added, followed by 0.012 mmol of triphenylcarbenium tetrakis(pentafluorophenyl)borate (hereinafter referred to as borate compound (1); synthesized with reference to JP 2018-150273 A) to initiate the polymerization reaction.

[0060] Ethylene was continuously supplied at 150 L / hr and hydrogen at 0.24 L / hr. Polymerization was carried out at 50°C under atmospheric pressure for 10 minutes, after which the polymerization was terminated by the addition of a small amount of isobutanol. After polymerization was completed, the reactants were added to 4.5 L of a 3:1 acetone / methanol mixed solvent containing a small amount of hydrochloric acid to precipitate the polymer. After washing with the same solvent, the polymer was dried under reduced pressure at 130°C for 10 hours, yielding 2.19 g of ethylene-tetracyclododecene copolymer. The polymerization activity was 4.38 kg / mmol·hr. The resulting ethylene-tetracyclododecene copolymer (structural unit (A): 56 mol% ethylene, structural unit (B): 44 mol% tetracyclododecene) had an intrinsic viscosity [η] of 0.47 dl / g, an Mw of 119,000 g / mol, and an Mw / Mn of 2.48. The glass transition temperature measured by differential scanning calorimetry (DSC) was 186°C, and the formability of the film for birefringence measurement was good (film formability: A). The birefringence was 0.2 nm. The results are shown in Table 1.

[0061] Example 2 A 500 mL glass reactor, thoroughly purged with nitrogen, was charged with 300 mL of a 9 / 1 cyclohexane / hexane mixed solution and 3.6 g of tetracyclododecene, and the liquid and gas phases were saturated with 90 L / hr of ethylene and 0.24 L / hr of hydrogen. 0.3 mmol of MMAO was added. 0.001 mmol of titanium compound (1) and 0.004 mmol of borate compound (1) were added to initiate polymerization.

[0062] Ethylene was continuously supplied at 90 L / hr and hydrogen at 0.24 L / hr, and the polymerization was carried out at 50°C under atmospheric pressure for 10 minutes. The polymerization was then terminated by the addition of a small amount of isobutanol. After polymerization, the reactants were added to 1.2 L of a 3:1 acetone / methanol mixed solvent containing a small amount of hydrochloric acid to precipitate the polymer. After washing with the same solvent, the polymer was dried under reduced pressure at 130°C for 10 hours, yielding 1.33 g of ethylene-tetracyclododecene copolymer. The polymerization activity was 7.97 kg / mmol·hr, and the resulting ethylene-tetracyclododecene copolymer (structural unit (A): 59 mol% ethylene, structural unit (B): 41 mol% tetracyclododecene) had an [η] of 0.46 (dl / g), a Mw of 104,000 (g / mol), and a Mw / Mn of 2.37. The glass transition temperature measured by DSC was 168°C, and the formability of the film for birefringence measurement was good (film formability: A). The birefringence was 3.1 nm. The results are shown in Table 1.

[0063] Example 3 A 500 mL glass reactor, thoroughly purged with nitrogen, was charged with 300 mL of a 9:1 cyclohexane / hexane mixed solution and 2.7 g of tetracyclododecene, and the liquid and gas phases were saturated with ethylene at 90 L / hr and hydrogen at 0.24 L / hr. 0.3 mmol of MMAO (modified methylaluminoxane) was added. Subsequently, 0.001 mmol of titanium compound (1) and 0.004 mmol of a borate compound were added to initiate the polymerization reaction.

[0064] Ethylene (90 L / hr) and hydrogen (0.24 L / hr) were continuously supplied, and the polymerization was carried out at 50°C under atmospheric pressure for 10 minutes. The polymerization was then terminated by the addition of a small amount of isobutanol. After polymerization completion, the reactants were added to 1.5 L of a 3:1 acetone / methanol mixed solvent containing a small amount of hydrochloric acid to precipitate the polymer. After washing with the same solvent, the polymer was dried under reduced pressure at 130°C for 10 hours, yielding 1.8 g of ethylene-tetracyclododecene copolymer. The polymerization activity was 1.8 kg / mmol·hr. The resulting ethylene-tetracyclododecene copolymer (structural unit (A): 63 mol% ethylene, structural unit (B): 37 mol% tetracyclododecene) had an intrinsic viscosity [η] of 0.53 (dl / g), a Mw of 114,000 (g / mol), and a Mw / Mn of 2.43. The glass transition temperature measured by DSC was 150°C, and the formability of the film for birefringence measurement was good (film formability: A). The birefringence was 7.7 nm. The results are shown in Table 1.

[0065] Comparative Example 1 A 500 mL glass reactor, thoroughly purged with nitrogen, was charged with 300 mL of a 9 / 1 cyclohexane / hexane mixture and 32.4 g of tetracyclododecene. The liquid and gas phases were saturated with ethylene at 90 L / hr and hydrogen at 0.24 L / hr. 0.3 mmol of MMAO was added. 0.00012 mmol of 3,5-bis(t-butyl)-1-pyrazolate-t-butylcyclopentadienyl titanium dichloride (hereinafter referred to as titanium compound (2)) and 0.004 mmol of borate compound (1) were added to initiate polymerization.

[0066] Ethylene (90 L / hr) and hydrogen (0.24 L / hr) were continuously fed into the reactor at atmospheric pressure and 50°C for 10 minutes. The polymerization was then terminated by the addition of a small amount of isobutanol. After polymerization, the reactants were added to 1.2 L of a 3:1 acetone / methanol mixture containing a small amount of hydrochloric acid to precipitate the polymer. After washing with the same solvent, the polymer was dried under reduced pressure at 130°C for 10 hours, yielding 1.54 g of ethylene-tetracyclododecene copolymer. The polymerization activity was 79.36 kg / mmol·hr. The resulting ethylene-tetracyclododecene copolymer (structural unit (A): 56 mol% ethylene, structural unit (B): 44 mol% tetracyclododecene) had an [η] of 0.17 (dl / g), an Mw of 26,100 (g / mol), and an Mw / Mn of 2.10. The glass transition temperature measured by DSC was 182°C, and the formability of the film for birefringence measurement was poor (film formability: D). Birefringence could not be measured. The results are shown in Table 1.

[0067] Comparative Example 2 A 500 mL glass reactor, thoroughly purged with nitrogen, was charged with 300 mL of a 9 / 1 cyclohexane / hexane mixture and 8.4 g of tetracyclododecene, and the liquid and gas phases were saturated with ethylene at 51 L / hr. 0.3 mmol of MMAO was added. 0.000125 mmol of titanium compound (2) and 0.004 mmol of borate compound (1) were added to initiate polymerization.

[0068] Ethylene was continuously supplied at 51 L / hr and polymerization was carried out at 50°C under atmospheric pressure for 10 minutes. The polymerization was then terminated by the addition of a small amount of isobutanol. After polymerization, the reactants were added to 1.2 L of a 3:1 acetone / methanol mixed solvent containing a small amount of hydrochloric acid to precipitate the polymer. After washing with the same solvent, the polymer was dried under reduced pressure at 130°C for 10 hours, yielding 0.84 g of ethylene-tetracyclododecene copolymer. The polymerization activity was 40.37 kg / mmol·hr. The resulting ethylene-tetracyclododecene copolymer (structural unit (A): 64 mol% ethylene, structural unit (B): 36 mol% tetracyclododecene) had an [η] of 3.15 (dl / g), an Mw of 1,290,000 (g / mol), and an Mw / Mn of 2.54. The glass transition temperature (Tg) measured by DSC was 156°C, and film formability for birefringence measurement was normal (film formability: B). The birefringence was 18.3 nm. The results are shown in Table 1.

[0069] Comparative Example 3 A 500 mL glass reactor, thoroughly purged with nitrogen, was charged with 300 mL of a 9 / 1 cyclohexane / hexane mixture and 5.3 g of tetracyclododecene, and the liquid and gas phases were saturated with ethylene at 51 L / hr. 0.3 mmol of MMAO was added. 0.000125 mmol of titanium compound (2) and 0.004 mmol of borate compound (1) were added to initiate polymerization.

[0070] Ethylene was continuously fed at 51 L / hr and polymerization was carried out at 50°C under atmospheric pressure for 10 minutes. The polymerization was then terminated by the addition of a small amount of isobutanol. After polymerization, the reactants were added to 1.2 L of a 3:1 acetone / methanol mixed solvent containing a small amount of hydrochloric acid to precipitate the polymer. After washing with the same solvent, the polymer was dried under reduced pressure at 130°C for 10 hours, yielding 0.68 g of ethylene-tetracyclododecene copolymer. The polymerization activity was 32.98 kg / mmol·hr. The resulting ethylene-tetracyclododecene copolymer (structural unit (A): 67 mol% ethylene, structural unit (B): 33 mol% tetracyclododecene) had an [η] of 4.80 (dl / g), an Mw of 3,520,000 (g / mol), and an Mw / Mn of 2.77. The glass transition temperature (Tg) measured by DSC was 138°C, and film formability for birefringence measurement was normal (film formability: B). The birefringence was 33.0 nm. The results are shown in Table 1.

[0071] [Table 1]

[0072] This application claims priority based on Japanese Patent Application No. 2022-037968, filed March 11, 2022, the disclosure of which is incorporated herein in its entirety.

Claims

1. A structural unit (A) derived from an olefin monomer represented by the following formula (1), A structural unit (B) derived from at least one cyclic olefin monomer selected from the group consisting of a cyclic olefin monomer represented by the following formula (2) and a cyclic olefin monomer represented by the following formula (3), A cyclic olefin copolymer comprising: When the total content of the structural unit (A) and the structural unit (B) in the cyclic olefin copolymer is taken as 100 mol %, the content of the structural unit (A) is 40 mol % or more and 70 mol % or less, and the content of the structural unit (B) is 30 mol % or more and 60 mol % or less, a weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) of 50,000 or more and 150,000 or less; a glass transition temperature (Tg) of 150°C or higher and 190°C or lower; A cyclic olefin copolymer having a molecular weight distribution (Mw / Mn) of 2.20 or more and 2.50 or less. 【Chemistry 1】 (In the formula (1), R ３００ represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 28 carbon atoms. 【Chemistry 2】 (In the formula (2), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, and R ６１ ~R ７８ and R ａ１ and R ｂ１ are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group; R ７５ ~R ７８ may be bonded to each other to form a monocyclic or polycyclic ring, and the monocyclic or polycyclic ring may have a double bond; R ７５ and R ７６ With or R ７７ and R ７８ and may form an alkylidene group.) 【Transformation 3】 (In the formula (3), x and d are integers of 0 or 1 or more, y and z are 0, 1 or 2, and R ８１ ~R ９９ are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group; R ８９ and R ９０ and a carbon atom to which R ９３ or the carbon atom to which R ９１ may be bonded directly or via an alkylene group having 1 to 3 carbon atoms, and when y=z=0, R ９５ and R ９２ or R ９５ and R ９９ may be bonded to each other to form a monocyclic or polycyclic aromatic ring.

2. The cyclic olefin copolymer according to claim 1, wherein the glass transition temperature (Tg) is 165°C or higher.

3. The cyclic olefin copolymer according to claim 1 or 2, which has an intrinsic viscosity η [dl / g] (in decalin at 135°C) of 0.60 dl / g or less.

4. 3. The cyclic olefin copolymer according to claim 1, wherein the cyclic olefin monomer constituting the structural unit (B) comprises at least one cyclic olefin monomer selected from the group consisting of tetracyclododecene, norbornene, and derivatives thereof.

5. The cyclic olefin copolymer according to claim 1 or 2, wherein the olefin monomer constituting the structural unit (A) contains ethylene.

6. A structural unit (A) derived from an olefin monomer represented by the following formula (1), A structural unit (B) derived from at least one cyclic olefin monomer selected from the group consisting of a cyclic olefin monomer represented by the following formula (2) and a cyclic olefin monomer represented by the following formula (3), A cyclic olefin copolymer comprising: When the total content of the structural unit (A) and the structural unit (B) in the cyclic olefin copolymer is taken as 100 mol %, the content of the structural unit (A) is 40 mol % or more and 70 mol % or less, and the content of the structural unit (B) is 30 mol % or more and 60 mol % or less, a weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) of 50,000 or more and 150,000 or less; a glass transition temperature (Tg) of 165°C or higher and 190°C or lower; A cyclic olefin copolymer in which the olefin monomer constituting the structural unit (A) contains ethylene. 【Chemistry 1】 (In the formula (1), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having from 1 to 28 carbon atoms.) 【Chemistry 2】 (In the formula (2), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, R 61 to R 78 and R a1 and R b1 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group, R 75 to R 78 may be bonded to each other to form a monocycle or a polycycle, the monocycle or the polycycle may have a double bond, and R 75 and R 76 or R 77 and R 78 may be bonded to each other to form an alkylidene group.) 【Transformation 3】 (In the formula (3), x and d are 0 or an integer of 1 or more, y and z are 0, 1, or 2, R 81 to R 99 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group, the carbon atom to which R 89 and R 90 are bonded may be bonded directly or via an alkylene group having 1 to 3 carbon atoms to the carbon atom to which R 93 is bonded or the carbon atom to which R 91 is bonded, and when y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic or polycyclic aromatic ring.)

7. A cyclic olefin copolymer according to claim 6, having a molecular weight distribution (Mw / Mn) of 2.20 or more and 2.50 or less.

8. A cyclic olefin copolymer according to claim 6 or 7, having an intrinsic viscosity η [dl / g] (in decalin at 135°C) of 0.60 dl / g or less.

9. A cyclic olefin copolymer as described in claim 6 or 7, wherein the cyclic olefin monomer constituting the structural unit (B) comprises at least one cyclic olefin monomer selected from the group consisting of tetracyclododecene, norbornene, and derivatives thereof.

10. A structural unit (A) derived from an olefin monomer represented by the following formula (1), A structural unit (B) derived from at least one cyclic olefin monomer selected from the group consisting of a cyclic olefin monomer represented by the following formula (2) and a cyclic olefin monomer represented by the following formula (3), A cyclic olefin copolymer comprising: When the total content of the structural unit (A) and the structural unit (B) in the cyclic olefin copolymer is taken as 100 mol %, the content of the structural unit (A) is 40 mol % or more and 70 mol % or less, and the content of the structural unit (B) is 30 mol % or more and 60 mol % or less, a weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) of 50,000 or more and 500,000 or less; A glass transition temperature (Tg) of 150°C or higher, a molecular weight distribution (Mw / Mn) of 2.20 or more and 2.50 or less; A cyclic olefin copolymer having an intrinsic viscosity η [dl / g] (in decalin at 135°C) of 0.60 dl / g or less. 【Chemistry 1】 (In the formula (1), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having from 1 to 28 carbon atoms.) 【Chemistry 2】 (In the formula (2), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, R 61 to R 78 and R a1 and R b1 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group, R 75 to R 78 may be bonded to each other to form a monocycle or a polycycle, the monocycle or the polycycle may have a double bond, and R 75 and R 76 or R 77 and R 78 may be bonded to each other to form an alkylidene group.) 【Transformation 3】 (In the formula (3), x and d are 0 or an integer of 1 or more, y and z are 0, 1, or 2, R 81 to R 99 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group, the carbon atom to which R 89 and R 90 are bonded may be bonded directly or via an alkylene group having 1 to 3 carbon atoms to the carbon atom to which R 93 is bonded or the carbon atom to which R 91 is bonded, and when y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic or polycyclic aromatic ring.)

11. The weight average molecular weight (Mw) is 50,000 or more and 150,000 or less, The cyclic olefin copolymer according to claim 10, wherein the glass transition temperature (Tg) is 150°C or higher and 190°C or lower.

12. A cyclic olefin copolymer according to claim 10 or 11, wherein the glass transition temperature (Tg) is 165°C or higher.

13. A cyclic olefin copolymer described in claim 10 or 11, wherein the cyclic olefin monomer constituting the structural unit (B) includes at least one cyclic olefin monomer selected from the group consisting of tetracyclododecene, norbornene, and derivatives thereof.

14. A cyclic olefin copolymer according to claim 10 or 11, wherein the olefin monomer constituting the structural unit (A) contains ethylene.

15. A structural unit (A) derived from an olefin monomer represented by the following formula (1), A structural unit (B) derived from at least one cyclic olefin monomer selected from the group consisting of a cyclic olefin monomer represented by the following formula (2) and a cyclic olefin monomer represented by the following formula (3), A cyclic olefin copolymer comprising: When the total content of the structural unit (A) and the structural unit (B) in the cyclic olefin copolymer is taken as 100 mol %, the content of the structural unit (A) is 40 mol % or more and 70 mol % or less, and the content of the structural unit (B) is 30 mol % or more and 60 mol % or less, a weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) of 50,000 or more and 500,000 or less; A glass transition temperature (Tg) of 165°C or higher; The intrinsic viscosity η [dl / g] (in decalin at 135°C) is 0.60 dl / g or less, A cyclic olefin copolymer in which the olefin monomer constituting the structural unit (A) contains ethylene. 【Chemistry 1】 (In the formula (1), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having from 1 to 28 carbon atoms.) 【Chemistry 2】 (In the formula (2), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, R 61 to R 78 and R a1 and R b1 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group, R 75 to R 78 may be bonded to each other to form a monocycle or a polycycle, the monocycle or the polycycle may have a double bond, and R 75 and R 76 or R 77 and R 78 may be bonded to each other to form an alkylidene group.) 【Transformation 3】 (In the formula (3), x and d are 0 or an integer of 1 or more, y and z are 0, 1, or 2, R 81 to R 99 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group, the carbon atom to which R 89 and R 90 are bonded may be bonded directly or via an alkylene group having 1 to 3 carbon atoms to the carbon atom to which R 93 is bonded or the carbon atom to which R 91 is bonded, and when y=z=0, R 95 and R 92 or R 95 and R 99 may be bonded to each other to form a monocyclic or polycyclic aromatic ring.)

16. The weight average molecular weight (Mw) is 50,000 or more and 150,000 or less, The cyclic olefin copolymer according to claim 15, wherein the glass transition temperature (Tg) is 165°C or higher and 190°C or lower.

17. A cyclic olefin copolymer according to claim 15 or 16, having a molecular weight distribution (Mw / Mn) of 2.20 or more and 2.50 or less.

18. A cyclic olefin copolymer described in claim 15 or 16, wherein the cyclic olefin monomer constituting the structural unit (B) comprises at least one cyclic olefin monomer selected from the group consisting of tetracyclododecene, norbornene, and derivatives thereof.

19. 16. The cyclic olefin copolymer according to claim 1, 6, 10, or 15, wherein when a press-molded body having a thickness of 0.1 mm is produced from the cyclic olefin copolymer and then uniaxially stretched, the uniaxially stretched press-molded body has a birefringence of 10 nm or less.

20. A cyclic olefin copolymer composition comprising the cyclic olefin copolymer according to claim 1 , 6 , 10 or 15 .

21. The cyclic olefin copolymer according to claim 1, 6, 10 or 15, which can be used for optical parts.

22. A molded article comprising the cyclic olefin copolymer according to claim 1 , 6 , 10 or 15 .

23. An optical component comprising the molded article according to claim 22.

24. The optical component according to claim 23, which is a lens for a head-mounted display.

25. Use of the optical component according to claim 23 for a lens for a head-mounted display.

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