Resin and its molded body

Abstract

To provide a resin which has high thermal stability enabling injection molding in a wide temperature region, low birefringence useful as an optical molding material and high moldability while maintaining high heat resistance and a high refractive index useful as the optical molding material.SOLUTION: A resin contains a structural unit represented by formula (1) and a structural unit represented by formula (2), and 40 wt.% or more of the structural unit represented by formula (2) in 100 wt.% of the resin.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a resin having a small absolute value of orientation birefringence, high thermal stability, and a high refractive index and high heat resistance, a resin composition containing this resin, and a molded article made of the resin and suitable as an optical member. [Background technology]

[0002] Polycarbonate resins are used as optical molding materials because of their excellent transparency, dimensional stability, mechanical properties, etc. Patent Document 1 discloses a polycarbonate resin that mainly contains repeating units having a 9,9-bisphenylfluorene skeleton as a polycarbonate resin with excellent optical properties. In the examples of Patent Document 1, a polycarbonate resin is prepared using 2,2'-[9H-fluoren-9-ylidenebis(4,1-phenyleneoxy)]-bisethanol [9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (abbreviation: BPEF)] as a polymerization component.

[0003] Patent Document 2 discloses a thermoplastic resin having a specific divalent oligofluorene structure as a repeating unit. Patent Document 2 discloses, as a second embodiment, a thermoplastic resin having an oligofluorene structure and a structure derived from a dihydric phenol compound in the repeating unit.

[0004] Patent Document 3 discloses a thermoplastic resin having a specific divalent oligofluorene structure as a repeating unit.

[0005] Patent Document 4 discloses a polyester resin in which a dicarboxylic acid unit having an oligofluorene skeleton and a diol unit having a 9,9-bisarylfluorene skeleton are combined. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication No. 10-101787 [Patent Document 2] JP 2017-075256 A [Patent Document 3] JP 2017-075255 A [Patent Document 4] JP 2018-172659 A Summary of the Invention [Problem to be solved by the invention]

[0007] However, the polycarbonate resin described in Patent Document 1 has poor thermal stability because the main skeleton contains carbonate bonds derived from an aliphatic hydroxy compound, and the temperatures at which it can be produced, melt-processed, and used as a molded product may be limited.

[0008] Furthermore, Patent Document 2 describes that the content of the structural units derived from dihydric phenol compounds in the resin is not limited, and that if the content of the structural units derived from dihydric phenol compounds is large, the processability may be impaired, and it is difficult to adjust the balance of physical properties such as optical properties and mechanical properties. For this reason, Patent Document 2 describes that the content of the structural units derived from dihydric phenol compounds in the resin is particularly preferably 30% by weight or less. Furthermore, although the examples in Patent Document 2 list a resin containing a structural unit derived from a dihydric phenol compound, the content is 33.2% by weight, and no specific disclosure is made of a resin containing 40% by weight or more. Moreover, the resins specifically disclosed have large negative orientation birefringence. In other words, Patent Document 2 does not contain any description suggesting that by appropriately selecting the content of structural units derived from a dihydric phenol compound in a resin having a divalent oligofluorene structure as a repeating unit, it is possible to design a resin having small birefringence and high thermal stability in the resulting molded article.

[0009] Furthermore, Patent Document 3 does not limit the content of structural units derived from aromatic dihydroxy compounds such as dihydric phenol compounds in the resin, and it is preferable that the content of aromatic structures other than oligofluorene structural units is 10% by weight or less. Furthermore, the examples of Patent Document 3 disclose only resins with a content of structural units derived from dihydric phenol compounds of 10% by weight or less. In these examples, the resin using isosorbide as the dihydroxy compound has a low refractive index of less than 1.59, and the resin using BPEF as the dihydroxy compound uses an aliphatic hydroxy compound, and therefore has poor thermal stability, possibly limiting the temperatures at which it can be produced, melt-processed, and used in molded products. Patent Document 3 also does not contain any description suggesting that by appropriately selecting the content of structural units derived from a dihydric phenol compound in a resin having a divalent oligofluorene structure as a repeating unit, it is possible to design a resin having small birefringence and high thermal stability of the resulting molded article.

[0010] In addition, although the resin of Patent Document 4 has a high refractive index and low birefringence, since an aliphatic hydroxy compound such as BPEF or 9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]fluorene (abbreviation: BNEF) is used as the diol unit, the thermal stability is poor, and the temperatures for production, melt processing, and use of molded products may be limited.

[0011] An object of the present invention is to provide a resin that has high thermal stability enabling injection molding over a wide temperature range while maintaining high heat resistance and a high refractive index useful as an optical molding material, and that has low birefringence and high moldability useful as an optical molding material, as well as a resin composition containing the resin and a molded product thereof. [Means for solving the problem]

[0012] As a result of intensive research aimed at solving the above-mentioned problems, the present inventors have discovered that at least one resin selected from the group consisting of polyester carbonates and polyesters, which contains a specific divalent oligofluorene structure and a specific amount of a structure derived from an aromatic dihydroxy compound in which a hydroxy group is directly bonded to an aromatic group, has excellent thermal stability and low birefringence, as well as a high refractive index and high heat resistance, and have arrived at the present invention. That is, the gist of the present invention lies in the following [1] to

[17] .

[0013] [1] At least one resin selected from the group consisting of polyester carbonates and polyesters, comprising a structural unit represented by the following formula (1) and a structural unit represented by the following formula (2): A resin containing 40% by weight or more of a structural unit represented by the following formula (2), when the total weight of the resin is taken as 100% by weight.

[0014] [ka]

[0015] (In formula (1), R 11 ~R 13 each independently represents a direct bond or an alkylene group having 1 to 4 carbon atoms which may have a substituent, R 14 ~R 19 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 10 carbon atoms which may have a substituent, an acyl group having 1 to 10 carbon atoms which may have a substituent, an amino group which may have a substituent, an alkenyl group having 2 to 10 carbon atoms which may have a substituent, an alkynyl group having 2 to 10 carbon atoms which may have a substituent, an oxygen atom which has a substituent, a sulfur atom which has a substituent, a silicon atom which has a substituent, a halogen atom, a nitro group, or a cyano group, provided that R 14 ~R 19 At least two adjacent groups among these may be bonded to each other to form a ring.)

[0016] [ka]

[0017] (In formula (2), Ar 1 represents an unsubstituted or substituted aromatic hydrocarbon group having 6 to 88 carbon atoms, or a divalent group having 6 to 88 carbon atoms in which an unsubstituted or substituted aromatic hydrocarbon ring is linked via a direct bond or any linking group, and each of the two oxygen atoms shown in formula (2) is represented by Ar 1 It represents that the ring is directly bonded to the same or different aromatic hydrocarbon rings in the ring.

[0018] [2] The resin according to [1], wherein the content of the structural unit represented by formula (1) is 5% by weight or more when the total weight of the resin is 100% by weight.

[0019] [3] The resin according to [1] or [2], wherein the total content of the structural unit represented by formula (1) and the structural unit represented by formula (2) is 80% by weight or more when the total weight of the resin is 100% by weight.

[0020] [4] The resin according to any one of [1] to [3], wherein the formula (2) is represented by the following formula (3):

[0021] [ka]

[0022] (In formula (3), ring Z 1 , Z 2 R each independently represents an aromatic hydrocarbon ring. 1 , R 2 are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, an oxygen atom having a substituent, a sulfur atom having a substituent, a silicon atom having a substituent, or a halogen atom. a and b are each independently an integer of 0 or more. When a and b are 2 or more, R 1 , R 2If there are multiple R 1 , R 2 may be the same or different. 1 and / or R 2 At least two of the groups may be bonded to each other to form a ring. Y represents a single bond, a hydrocarbon group having 1 to 44 carbon atoms which may contain an aromatic group, O, S, SS, SO, SO 2 or a CO group.

[0023] [5] In the formula (3), Y is a single bond, a hydrocarbon group having 1 to 44 carbon atoms which may contain an aromatic group, S, SS, SO, or SO 2 The resin according to [4],

[0024] [6] In the formula (3), Y is a single bond, S, SS, SO, SO 2 or a group represented by any one of the following formulae (Y1) to (Y3) (wherein the * mark in the following formulae (Y1) to (Y3) represents the ring Z in the above formula (3) 1 , Z 2 The resin according to [5], wherein

[0025] [ka]

[0026] (In formula (Y1), R 3 , R 4 are each independently a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms.

[0027] [ka]

[0028] (In formula (Y2), R 5 R is a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms. 6is an unsubstituted or substituted aromatic hydrocarbon group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, or a halogen atom. c represents an integer of 0 to 5. When c is 2 or more, R 6 If there are multiple R 6 may be the same or different. 6 At least two of the groups may be bonded to each other to form a ring.

[0029] [ka]

[0030] (In formula (Y3), R 7 , R 8 are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, or a halogen atom. d and e are each independently an integer of 0 to 5. When d and e are 2 or more, R 7 , R 8 If there are multiple R 7 , R 8 may be the same or different. 7 and / or R 8 At least two of the groups may be bonded to each other to form a ring.

[0031] [7] The resin according to [6], wherein the formula (3) is at least one selected from the group consisting of the following formulas (3-1) to (3-5):

[0032] [ka]

[0033] (In formulas (3-1) to (3-5), R 1 , R 2, a, and b are defined as in formula (3). 6 , c are defined as in formula (Y2). 7 , R 8 , d, and e are defined the same as in formula (Y2).

[0034] [8] The resin according to [7], wherein the formula (3) is at least one selected from the group consisting of the following formulas (3-6) to (3-10):

[0035] [ka]

[0036] [9] The resin according to any one of [1] to [8], which has a refractive index of 1.59 or more at a wavelength of 589 nm.

[0037]

[10] The resin according to any one of [1] to [9], having an Abbe number vD of 35.0 or less.

[0038]

[11] The resin according to any one of [1] to

[10] , wherein a stretched film made from the resin has an in-plane orientation birefringence of −0.0010 or more and 0.0020 or less at a wavelength of 550 nm.

[0039]

[12] The resin according to any one of [1] to

[11] , which has a 1% thermal weight loss temperature (Td) under nitrogen of 355°C or higher.

[0040]

[13] The resin according to any one of [1] to

[12] , having a glass transition temperature (Tg) of 110° C. or higher and 250° C. or lower.

[0041]

[14] A resin composition comprising the resin according to any one of [1] to

[13] and at least one additive selected from the group consisting of a heat stabilizer, an antioxidant, an ultraviolet absorber, a brightness enhancer, a dye, a pigment, a release agent, a flow modifier, and an impact resistance improver.

[0042]

[15] A resin composition comprising the resin according to any one of [1] to

[13] or the resin composition according to

[14] , and further containing another resin.

[0043]

[16] A molded article obtained by molding the resin according to any one of [1] to

[13] or the resin composition according to

[14] or

[15] .

[0044]

[17] The molded article according to

[16] , which is an optical component.

[0045]

[18] The molded body according to

[17] , wherein the optical component is at least one optical lens selected from the group consisting of an in-vehicle lens, a spectacle lens, a pickup lens, a camera lens, a microarray lens, a projector lens, and a Fresnel lens. Effect of the Invention

[0046] The resin of the present invention has a structural unit represented by the formula (1) and a structural unit represented by the formula (2), and contains the structural unit represented by the formula (2) in a specific ratio, so that the obtained molded article can be designed as a resin with low birefringence and high thermal stability. As a result, the resin has high thermal stability that allows injection molding over a wide temperature range, while maintaining high heat resistance and a high refractive index useful as an optical molding material, and has low birefringence and high moldability useful as an optical molding material.

[0047] The resin of the present invention has high thermal stability, a small absolute value of orientation birefringence, and the birefringence of the resulting molded article is low, and the resin has a high refractive index and high heat resistance. Therefore, the resin of the present invention and the resin composition of the present invention containing the resin can be easily processed into optical components by a method such as injection molding. These optical members have a high refractive index and low birefringence while maintaining high thermal stability and high heat resistance, and are therefore useful as high-performance optical members. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0048] Hereinafter, the present invention will be described in detail with reference to embodiments and examples, but the present invention should not be construed as being limited to the embodiments and examples shown below. In this specification, unless otherwise specified, the symbol "~" is used to mean that the numerical values ​​before and after it are included as the lower and upper limits. Furthermore, the term "structural unit" refers to a partial structure sandwiched between adjacent linking groups in a polymer, and a partial structure sandwiched between a polymerization reactive group present at the end portion of a polymer and a linking group adjacent to the polymerization reactive group.

[0049] In the present invention, the polycarbonate resin refers to a resin in which the structural units constituting the resin contain a portion (carbonate group) in which the structural units constituting the resin are linked by carbonate bonds. The polyester resin refers to a resin in which the structural units constituting the resin contain a portion (ester group) in which the structural units constituting the resin are linked by ester bonds. The resin of the present invention may be a polyestercarbonate resin having a carbonate group and an ester group.

[0050] [resin] The resin of the present invention is at least one resin selected from the group consisting of polyester carbonates and polyesters, which contains a structural unit represented by the following formula (1) (hereinafter may be referred to as "structural unit (1)") and a structural unit represented by the following formula (2) (hereinafter may be referred to as "structural unit (2)"), and is characterized in that, when the total weight of the resin is 100% by weight, it contains 40% by weight or more of the structural unit (2).

[0051] [ka]

[0052] (In formula (1), R 11 ~R 13 each independently represents a direct bond or an alkylene group having 1 to 4 carbon atoms which may have a substituent, R 14 ~R 19are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 10 carbon atoms which may have a substituent, an acyl group having 1 to 10 carbon atoms which may have a substituent, an amino group which may have a substituent, an alkenyl group having 2 to 10 carbon atoms which may have a substituent, an alkynyl group having 2 to 10 carbon atoms which may have a substituent, an oxygen atom which has a substituent, a sulfur atom which has a substituent, a silicon atom which has a substituent, a halogen atom, a nitro group, or a cyano group, provided that R 14 ~R 19 At least two adjacent groups among these may be bonded to each other to form a ring.)

[0053] [ka]

[0054] (In formula (2), Ar 1 represents an unsubstituted or substituted aromatic hydrocarbon group having 6 to 88 carbon atoms, or a divalent group having 6 to 88 carbon atoms in which an unsubstituted or substituted aromatic hydrocarbon ring is linked via a direct bond or any linking group, and each of the two oxygen atoms shown in formula (2) is represented by Ar 1 It represents that the ring is directly bonded to the same or different aromatic hydrocarbon rings in the ring.

[0055] Many polymers have positive intrinsic birefringence, but oligofluorene structural units have negative intrinsic birefringence, and it is believed that by adjusting the ratio of structural units having positive intrinsic birefringence and structural units having negative intrinsic birefringence in the resin, it is possible to make the birefringence of the resin almost zero. Since the oligofluorene structural units have a relatively large negative intrinsic birefringence, the birefringence of the resin can be adjusted to zero with a small content, so that a structural unit derived from an aromatic dihydroxy compound in which a hydroxy group is directly bonded to an aromatic group can be incorporated into the resin, and it is believed that the thermal stability and heat resistance of the resin can be improved. In addition, since this oligofluorene structural unit has a high density of aromatic structures, it is believed that it can be suitably used in cases where a high refractive index is required, such as for optical lens applications.

[0056] The contents of the structural unit (1), the structural unit (2) and other structural units described below in the resin can be determined by the method described in the Examples section below.

[0057] <Structural unit (1)> In the formula (1) representing the structural unit (1), R 11 and R 12 R are each independently a direct bond or an alkylene group having 1 to 4 carbon atoms which may have a substituent. The substituent is not particularly limited as long as it does not impair the effects of the present invention, but is preferably selected from an alkyl group having 1 to 3 carbon atoms and a halogen atom. 11 and R 12 As the alkylene group having 1 to 4 carbon atoms which may have a substituent, for example, the following alkylene groups can be used.

[0058] Straight-chain alkylene groups, such as a methylene group, an ethylene group, an n-propylene group, or an n-butylene group; and branched-chain alkylene groups, such as a methylmethylene group, a dimethylmethylene group, an ethylmethylene group, a propylmethylene group, a (1-methylethyl)methylene group, a 1-methylethylene group, a 2-methylethylene group, a 1-ethylethylene group, a 2-ethylethylene group, a 1-methylpropylene group, a 2-methylpropylene group, a 1,1-dimethylethylene group, a 2,2-dimethylpropylene group, or a 3-methylpropylene group. Chloromethylene group, dichloromethylene group, 1-chloroethylene group, 2-chloroethylene group, 1,1-dichloroethylene group, 2,2-dichloroethylene group, 1,2-dichloroethylene group, 1,1,2-trichloroethylene group, 1,2,2-trichloroethylene group, 1,1,2,2-tetrachloroethylene group, 1-chloro-n-propylene group, 1-chloro-n-butylene group, chloromethylmethylene group, chloroethylmethylene group, chloropropylmethylene group, chloro(1-methylethyl) ) alkylene groups having a chloro group, such as a methylene group, a 1-chloro-1-methylethylene group, a 2-chloro-1-methylethylene group, a 1-chloro-2-methylethylene group, a 2-chloro-2-methylethylene group, a 1-chloro-1-ethylethylene group, a 2-chloro-1-ethylethylene group, a 1-chloro-2-ethylethylene group, a 2-chloro-2-ethylethylene group, or a 2-chloro-1,1-dimethylethylene group; and alkylene groups having a bromo group in which the above-mentioned chloro group is replaced with a bromo group. Here, R 11 and R 12 The positions of the branched chains and substituents in the formula are indicated by numbers assigned so that the carbon atom on the fluorene ring side is at the 1st position.

[0059] R 11 and R 12 The selection of R has a particularly significant effect on the appearance of negative birefringence. The largest negative birefringence is exhibited when the fluorene rings in the oligofluorene structural unit are oriented perpendicular to the main chain direction (stretching direction). In order to bring the orientation state of the fluorene rings closer to the above state and to exhibit large negative birefringence, it is preferable to select R having an alkylene group with 2 to 3 carbon atoms on the main chain. 11 and R12 It is preferable to use R 11 and R 12 It is more preferable to adopt R. When the carbon number is 1, unexpectedly, negative birefringence may not be exhibited. This may be due to the steric hindrance of the carbonate group or ester group, which is the linking group of the oligofluorene structural unit, causing the orientation of the fluorene ring to be fixed in a direction that is not perpendicular to the main chain direction. On the other hand, when the carbon number is too large, the fixing of the orientation of the fluorene ring becomes weak, and the negative birefringence may become weak. In addition, the heat resistance of the resin tends to decrease. From the viewpoints of excellent optical properties and various physical properties, and ease of production, R 11 and R 12 is preferably a linear alkylene group, more preferably a propylene group or an ethylene group, and particularly preferably an ethylene group.

[0060] As shown in the above formula (1), R 11 and R 12 has excellent thermal stability, heat resistance and negative birefringence, since one end of the alkylene group is bonded to a fluorene ring and the other end is bonded to a carbonyl carbon. As described later, specific examples of monomers having an oligofluorene structure include dihydroxy compounds or diester compounds (hereinafter, diesters include dicarboxylic acids), and it is preferable to use a diester compound as a raw material to derive the structural unit (1). From the viewpoint of facilitating production, R 11 and R 12 It is preferable to employ the same alkylene group for each of the groups.

[0061] In the formula (1) representing the structural unit (1), R 13 R is a direct bond or an alkylene group having 1 to 4 carbon atoms which may have a substituent. The substituent is not particularly limited as long as it does not impair the effects of the present invention, but is preferably selected from an alkyl group having 1 to 3 carbon atoms and a halogen atom. 13 As the alkylene group having 1 to 4 carbon atoms which may have a substituent, for example, the following alkylene groups can be used.

[0062] Straight-chain alkylene groups such as a methylene group, an ethylene group, an n-propylene group, or an n-butylene group; and branched-chain alkylene groups such as a methylmethylene group, a dimethylmethylene group, an ethylmethylene group, a propylmethylene group, a (1-methylethyl)methylene group, a 1-methylethylene group, a 2-methylethylene group, a 1-ethylethylene group, a 2-ethylethylene group, a 1-methylpropylene group, a 2-methylpropylene group, a 1,1-dimethylethylene group, a 2,2-dimethylpropylene group, or a 3-methylpropylene group. Chloromethylene group, dichloromethylene group, 1-chloroethylene group, 2-chloroethylene group, 1,1-dichloroethylene group, 2,2-dichloroethylene group, 1,2-dichloroethylene group, 1,1,2-trichloroethylene group, 1,2,2-trichloroethylene group, 1,1,2,2-tetrachloroethylene group, 1-chloro-n-propylene group, 1-chloro-n-butylene group, chloromethylmethylene group, chloroethylmethylene group, chloropropylmethylene group, chloro(1-methylethyl) ) alkylene groups having a chloro group, such as a methylene group, a 1-chloro-1-methylethylene group, a 2-chloro-1-methylethylene group, a 1-chloro-2-methylethylene group, a 2-chloro-2-methylethylene group, a 1-chloro-1-ethylethylene group, a 2-chloro-1-ethylethylene group, a 1-chloro-2-ethylethylene group, a 2-chloro-2-ethylethylene group, or a 2-chloro-1,1-dimethylethylene group; and alkylene groups having a bromo group in which the above-mentioned chloro group is replaced with a bromo group.

[0063] R 13 The alkylene group preferably has 1 to 2 carbon atoms on the main chain, and more preferably has 1 carbon atom. 13 If you adopt R 11 and R 12As in the case of , the fixation of the fluorene rings is weakened, which may lead to a decrease in negative birefringence, an increase in the photoelastic coefficient, and a decrease in heat resistance. On the other hand, the fewer the number of carbon atoms on the main chain, the better the optical properties and heat resistance, but when the 9-positions of two fluorene rings are directly bonded, the thermal stability deteriorates. From the viewpoints of excellent optical properties and various physical properties, and ease of production, R 13 is preferably an unsubstituted linear alkylene group, more preferably an ethylene group or a methylene group, and particularly preferably a methylene group.

[0064] In the formula (1) representing the structural unit (1), R 14 ~R 19 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 10 carbon atoms which may have a substituent, an acyl group having 1 to 10 carbon atoms which may have a substituent, an amino group which may have a substituent, an alkenyl group having 2 to 10 carbon atoms which may have a substituent, an alkynyl group having 2 to 10 carbon atoms which may have a substituent, an oxygen atom which has a substituent, a sulfur atom which has a substituent, a silicon atom which has a substituent, a halogen atom, a nitro group, or a cyano group, provided that R 14 ~R 19 At least two adjacent groups among these may be bonded to each other to form a ring. The substituent here is not particularly limited as long as it does not impair the effects of the present invention, but is preferably selected from an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, and a halogen atom.

[0065] R 14 ~R 19 The alkyl group having 1 to 10 carbon atoms, which may have a substituent, may be linear, branched, or cyclic. As the alkyl group having 1 to 10 carbon atoms, which may have a substituent, for example, the following alkyl groups can be used. Methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl; alkyl groups having a chloro group, such as a chloromethyl group, a dichloromethyl group, a trichloromethyl group, a 1-chloroethyl group, a 2-chloroethyl group, a 1-chloropropyl group, a 1-chloroisopropyl group, a 1-chloro-n-butyl group, a 2-chloro-tert-butyl group, or a 1-chloro-cyclohexyl group; and alkyl groups having a bromo group, in which the above-mentioned chloro group is replaced with a bromo group.

[0066] R 14 ~R 19 Examples of the aryl group having 6 to 10 carbon atoms which may have a substituent include unsubstituted phenyl and naphthyl groups. Examples of those having a substituent include methylphenyl (tolyl), ethylphenyl, propylphenyl, butylphenyl, dimethylphenyl, trimethylphenyl, chlorophenyl, and bromophenyl groups. From the viewpoint of the thermal stability and heat resistance of the resin of the present invention, unsubstituted ones are preferred.

[0067] R 14 ~R 19 Examples of the acyl group having 1 to 10 carbon atoms which may have a substituent include a methanoyl group, an ethanoyl group, a propanoyl group, a butanoyl group, a pentanoyl group, a hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, a benzoyl group, an acrylyl group, a chloroethanoyl group, a dichloroethanoyl group, a trichloroethanoyl group, a bromoethanoyl group, and a fluoroethanoyl group.

[0068] R 14 ~R 19 The amino group which may have a substituent is, for example, an unsubstituted one such as NH 2 Examples of the substituted groups include dialkylamino groups and bis(alkylcarbonyl)amino groups. Examples of the dialkylamino groups include di-C groups such as dimethylamino groups.1-4 Examples of the bis(alkylcarbonyl)amino group include bis(C 1-4 alkyl-carbonyl)amino groups and the like.

[0069] R 14 ~R 19 The alkenyl group having 2 to 10 carbon atoms which may have a substituent may be linear, branched, or cyclic. As the alkenyl group having 2 to 10 carbon atoms which may have a substituent, for example, the following alkenyl groups can be used. ethenyl, propenyl, isopropenyl, n-butenyl, isobutenyl, pentenyl, n-hexenyl, cyclohexenyl, n-heptenyl, n-octenyl, n-nonenyl, n-decenyl; alkenyl groups having a chloro group, such as 1-chloroethenyl, 2-chloroethenyl, 1-chloropropenyl, 1-chloro-n-butenyl, and 2-chloro-cyclohexyl; and alkenyl groups having a bromo group in which the above-mentioned chloro group is replaced with a bromo group.

[0070] R 14 ~R 19 The alkynyl group having 2 to 10 carbon atoms which may have a substituent may be linear, branched, or cyclic. As the alkynyl group having 2 to 10 carbon atoms which may have a substituent, for example, the following alkynyl groups can be used. ethynyl, propynyl, n-butynyl, pentynyl, n-hexynyl, cyclohexynyl, n-heptynyl, n-octynyl, n-nonynyl, n-decynyl; alkynyl groups having a chloro group, such as a chloroethynyl group, a 3-chloropropenyl group, or a 3-chloro-n-butenyl group; and alkynyl groups having a bromo group in which the above-mentioned chloro group is replaced with a bromo group.

[0071] R 14 ~R 19Examples of the oxygen atom having a substituent include a hydroxy group; an alkoxy group, such as a methoxy group, an ethoxy group, a propyloxy group, a hexyloxy group, a cyclohexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, or a decyloxy group; an aryloxy group, such as a phenoxy group or a benzyloxy group; an acyloxy group, such as a methanoyloxy group, an ethanoyloxy group, a propanoyloxy group, a butanoyloxy group, a pentanoyloxy group, a hexanoyloxy group, a heptanoyloxy group, an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a benzoyloxy group, an acrylyloxy group, a chloroethanoyloxy group, a dichloroethanoyloxy group, a trichloroethanoyloxy group, a bromoethanoyloxy group, or a fluoroethanoyloxy group; and an oxygen atom having the same or different benzene rings on a fluorene skeleton as described later as a crosslinking structure.

[0072] R 14 ~R 19 Examples of the sulfur atom having a substituent include a thiol group; alkylthio groups such as a methylthio group, an ethylthio group, a propylthio group, a hexylthio group, a cyclohexylthio group, a heptylthio group, an octylthio group, a nonylthio group, and a decylthio group; arylthio groups such as a phenylthio group and a benzylthio group; a sulfo group; and sulfur atoms having a crosslinking structure with the same or different benzene rings on a fluorene skeleton described later, and a sulfonyl group.

[0073] R 14 ~R 19 Examples of the silicon atom having a substituent of the above include a silyl group, a monomethylsilyl group, a dimethylsilyl group, a trimethylsilyl group, a triethylsilyl group, and silicon atoms having a crosslinking structure with the same or different benzene rings on the fluorene skeleton described below.

[0074] R 14 ~R 19 Examples of the halogen atom include a chlorine atom, a bromine atom, and a fluorine atom.

[0075] R 14 ~R 19When at least two adjacent groups among the above are bonded to each other to form a ring, examples include the following. (a) Two adjacent substituents (R 14 and R 15 , R 15 and R 16 , R 16 and R 14 , R 17 and R 18 , R 18 and R 19 , R 19 and R 17 ) are bonded to each other to form a fused ring that is fused to a single benzene ring. (b) Two adjacent substituents (R 16 and R 17 ) are bonded to each other to form a bridge between the two benzene rings. Specific examples of the above (b) include -O-, -S-, and -SO 2 -, -Si-, -SiH 2 -,-SiMe 2 - or -SiEt 2 -, a bridge structure that links the carbon atoms on two benzene rings is an example.

[0076] The fluorene ring contained in the structural unit (1) is R 14 ~R 19 are all hydrogen atoms, or R 14 and / or R 19 is any one selected from the group consisting of a halogen atom, an acyl group, a nitro group, a cyano group, and a sulfo group, and R 15 ~R 18 is a hydrogen atom. In the former case, the compound containing the structural unit (1) can be derived from fluorene, which is industrially inexpensive. In the latter case, the reactivity of the 9-position of fluorene is improved, so that various derivatization reactions tend to be applicable in the synthesis process of the compound containing the structural unit (1). The fluorene ring is more preferably one of the following: R 14 ~R19 are all hydrogen atoms, or R 14 and / or R 19 is any one selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, and a nitro group, and R 15 ~R 18 is a hydrogen atom, 14 ~R 19 It is particularly preferable that all of are hydrogen atoms. By adopting the above-mentioned configuration, the fluorene ratio can be increased, and steric hindrance between the fluorene rings is unlikely to occur, and desired optical properties derived from the fluorene rings tend to be obtained.

[0077] As the structural unit (1), structural units represented by the following formulae (1A) and (1B) are particularly preferred.

[0078] [ka]

[0079] The resin of the present invention may contain only one type of the structural unit (1), or may contain two or more types.

[0080] The content of the structural unit (1) in the resin of the present invention is preferably 1% by weight or more, more preferably 5% by weight or more, even more preferably 10% by weight or more, and particularly preferably 20% by weight or more, when the total weight of the resin is taken as 100% by weight. If the content of the structural unit (1) is equal to or more than the above lower limit, the effect of reducing the birefringence of the resin due to the inclusion of the structural unit (1) can be effectively obtained. On the other hand, the content of the structural unit (1) in 100% by weight of the resin of the present invention is 60% by weight or less, preferably 56% by weight or less, more preferably 45% by weight or less, from the viewpoint of ensuring the content of the structural unit (2).

[0081] Examples of monomers that serve as resin raw materials for inducing such structural unit (1) into a resin include diester compounds represented by the following formula (11).

[0082] [ka]

[0083] (In formula (11), R 11 ~R 19 is R in the above formula (1). 11 ~R 19 This is the same definition as A. 1 and A 2 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, and A1 and A2 may be the same or different.

[0084] A in the above formula (11) 1 and A 2 When A in formula (11) is a hydrogen atom or an aliphatic hydrocarbon group such as a methyl group or an ethyl group, the polymerization reaction may not occur easily under the polymerization conditions of a polycarbonate resin or a polyester resin that is usually used. 1 and A 2 is preferably an aromatic hydrocarbon group such as a phenyl group or a tolyl group, and is particularly preferably a phenyl group.

[0085] Structural unit (2) In the formula (2) representing the structural unit (2), Ar 1 Ar represents an unsubstituted or substituted aromatic hydrocarbon group having 6 to 88 carbon atoms, or a divalent group having 6 to 88 carbon atoms in which an unsubstituted or substituted aromatic hydrocarbon ring is linked via a direct bond or any linking group. 1 may be a divalent group consisting of one aromatic hydrocarbon ring, or may be one in which two or more aromatic hydrocarbon rings are bonded via a linking group or by a direct bond. Here, the aromatic hydrocarbon ring may be a single ring or a condensed ring. In either case, it is important that the two oxygen atoms in formula (2) are directly bonded to the same or different aromatic hydrocarbon rings, and the thermal stability of the resin is improved by both of the two oxygen atoms being directly bonded to the aromatic hydrocarbon ring.

[0086] It is particularly preferable that the structural unit (2) is a structural unit represented by the following formula (3) from the viewpoint of the balance of various physical properties, such as thermal stability, heat resistance, mechanical properties, and optical properties such as transparency, refractive index, and birefringence.

[0087] [ka]

[0088] (In formula (3), ring Z 1 , Z 2 R each independently represents an aromatic hydrocarbon ring. 1 , R 2 are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, an oxygen atom having a substituent, a sulfur atom having a substituent, a silicon atom having a substituent, or a halogen atom. a and b are each independently an integer of 0 or more. When a and b are 2 or more, R 1 , R 2 If there are multiple R 1 , R 2 may be the same or different. 1 and / or R 2 At least two of the groups may be bonded to each other to form a ring. Y represents a single bond, a hydrocarbon group having 1 to 44 carbon atoms which may contain an aromatic group, O, S, SS, SO, SO 2 or a CO group.

[0089] In the above formula (3), ring Z 1 , Z 2 Each independently represents an aromatic hydrocarbon ring. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, and an anthracene ring. From the viewpoint of improving the fluidity of the resin, the ring Z 1 , Z 2 are each independently preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring.

[0090] R 1 , R2 are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, an oxygen atom having a substituent, a sulfur atom having a substituent, a silicon atom having a substituent, or a halogen atom, provided that a and b are 2 or more and R 1 , R 2 If there are multiple R 1 , R 2 may be the same or different. 1 and / or R 2 At least two of the groups may be bonded to each other to form a ring.

[0091] In the above, the substituent is not particularly limited as long as it does not impair the effects of the present invention, but is preferably selected from an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, and a halogen atom.

[0092] R 1 , R 2 The unsubstituted or substituted alkyl group having 1 to 10 carbon atoms may be linear, branched, or cyclic. Examples of the unsubstituted or substituted alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an n-hexyl group, a cyclohexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, and an n-decyl group.

[0093] R 1 , R 2 Examples of the unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms include unsubstituted phenyl and naphthyl groups. Examples of substituted aromatic hydrocarbon groups include methylphenyl (tolyl), ethylphenyl, propylphenyl, butylphenyl, dimethylphenyl, and trimethylphenyl groups. From the viewpoint of the thermal stability and heat resistance of the resin of the present invention, unsubstituted aromatic hydrocarbon groups are preferred.

[0094] R 1 , R 2 Examples of the unsubstituted or substituted acyl group having 1 to 10 carbon atoms include a methanoyl group, an ethanoyl group, a propanoyl group, a butanoyl group, a pentanoyl group, a hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, a benzoyl group, an acrylyl group, a chloroethanoyl group, a dichloroethanoyl group, a trichloroethanoyl group, a bromoethanoyl group, and a fluoroethanoyl group.

[0095] R 1 , R 2 Examples of the oxygen atom having a substituent include a hydroxy group; an alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, a hexyloxy group, a cyclohexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, a phenoxy group, or a benzyloxy group; 1 and Ring Z 2 and oxygen atoms forming a bridging structure.

[0096] R 1 , R 2 Examples of the sulfur atom having a substituent include a thiol group; an alkylthio group such as a methylthio group, an ethylthio group, a propylthio group, a hexylthio group, a cyclohexylthio group, a heptylthio group, an octylthio group, a nonylthio group, or a decylthio group; an arylthio group such as a phenylthio group or a benzylthio group; a sulfo group; 1 and Ring Z 2 and sulfur atoms and sulfonyl groups which form a cross-linking structure.

[0097] R 1 , R 2 Examples of the silicon atom having a substituent of the formula (I) include a silyl group, a monomethylsilyl group, a dimethylsilyl group, a trimethylsilyl group, and a triethylsilyl group; 1 and Ring Z 2 and silicon atoms forming a bridge structure.

[0098] R 1, R 2 Examples of the halogen atom include a chlorine atom, a bromine atom, and a fluorine atom.

[0099] R 1 and / or R 2 When at least two of the groups are bonded to each other to form a ring, examples include the following. (a) Adjacent R 1 and R 1 are bonded together to form ring Z 1 It forms a fused ring with (b) Adjacent R 2 and R 2 are bonded together to form ring Z 2 It forms a fused ring with (c) R 1 and R 2 is bonded to ring Z 1 and Ring Z 2 and form a cross-linked structure. Specific examples of the above (c) include -O-, -S-, and -SO 2 -, -Si-, -SiH 2 -,-SiMe 2 - or -SiEt 2 -And Ring Z 1 Carbon atom above and ring Z 2 Examples of such structures include bridge structures linking the above carbon atoms (Me represents a methyl group, and Et represents an ethyl group).

[0100] R 1 , R 2 Among these, a methyl group, a cyclohexyl group, a phenyl group, and a naphthyl group are preferable, a methyl group, a cyclohexyl group, and a phenyl group are more preferable, a methyl group and a phenyl group are further preferable, and a methyl group is particularly preferable.

[0101] a and b each independently represent an integer of 0 or greater. Among these, a and b each independently preferably represent an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0102] Y is a single bond, a hydrocarbon group having 1 to 44 carbon atoms which may contain an aromatic group, O, S, SS, SO, SO 2 or a CO group, but from the viewpoint of a balance of various physical properties such as heat resistance, mechanical properties, and a high refractive index, a single bond, a hydrocarbon group which may contain an aromatic group having 1 to 44 carbon atoms, S, SS, SO, or SO 2 and more preferably a single bond, S, SS, SO, SO 2 or a group represented by any one of the following formulae (Y1) to (Y3) (wherein the * mark in the following formulae (Y1) to (Y3) represents the ring Z in the above formula (3) 1 , Z 2 This shows the connection with .

[0103] [ka]

[0104] (In formula (Y1), R 3 , R 4 are each independently a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms.

[0105] [ka]

[0106] (In formula (Y2), R 5 R is a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms. 6 is an unsubstituted or substituted aromatic hydrocarbon group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, or a halogen atom. c represents an integer of 0 to 5. When c is 2 or more, R 6 If there are multiple R 6 may be the same or different. 6 At least two of the groups may be bonded to each other to form a ring.

[0107] [ka]

[0108] (In formula (Y3), R 7 , R 8 are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, or a halogen atom. d and e are each independently an integer of 0 to 5. When d and e are 2 or more, R 7 , R 8 If there are multiple R 7 , R 8 may be the same or different. 7 and / or R 8 At least two of the groups may be bonded to each other to form a ring.

[0109] In the above formula (Y1), R 3 , R 4 are each independently a hydrogen atom, or an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms. The unsubstituted or substituted alkyl group having 1 to 10 carbon atoms may be linear, branched, or cyclic. Examples of the unsubstituted or substituted alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an n-hexyl group, a cyclohexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, and an n-decyl group.

[0110] R 3 , R 4 are each independently preferably a hydrogen atom, a methyl group, an ethyl group, or a cyclohexyl group, more preferably a hydrogen atom, a methyl group, or an ethyl group, further preferably a hydrogen atom or a methyl group, and particularly preferably a methyl group.

[0111] In the above formula (Y2), R 5 is a hydrogen atom, or an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms. The unsubstituted or substituted alkyl group having 1 to 10 carbon atoms may be linear, branched, or cyclic. Examples of the unsubstituted or substituted alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an n-hexyl group, a cyclohexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, and an n-decyl group.

[0112] R 5 As the alkyl group, a hydrogen atom, a methyl group, an ethyl group, or a cyclohexyl group is preferable, a hydrogen atom, a methyl group, or an ethyl group is more preferable, a hydrogen atom or a methyl group is further preferable, and a methyl group is particularly preferable.

[0113] R 6 is an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, or a halogen atom. 6 At least two of the groups may be bonded to each other to form a ring.

[0114] In the above, the substituent is not particularly limited as long as it does not impair the effects of the present invention, but is preferably selected from an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, and a halogen atom.

[0115] R 6The unsubstituted or substituted alkyl group having 1 to 10 carbon atoms may be linear, branched, or cyclic. Examples of the unsubstituted or substituted alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an n-hexyl group, a cyclohexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, and an n-decyl group.

[0116] R 6 Examples of the unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms include unsubstituted phenyl and naphthyl groups. Substituted groups include methylphenyl (tolyl), ethylphenyl, propylphenyl, butylphenyl, dimethylphenyl, and trimethylphenyl groups. From the viewpoint of the thermal stability and heat resistance of the resin of the present invention, unsubstituted groups are preferred.

[0117] R 6 Examples of the unsubstituted or substituted acyl group having 1 to 10 carbon atoms include a methanoyl group, an ethanoyl group, a propanoyl group, a butanoyl group, a pentanoyl group, a hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, a benzoyl group, an acrylyl group, a chloroethanoyl group, a dichloroethanoyl group, a trichloroethanoyl group, a bromoethanoyl group, and a fluoroethanoyl group.

[0118] R 6 Examples of the halogen atom include a chlorine atom, a bromine atom, and a fluorine atom.

[0119] R 6 When at least two of the groups are bonded to each other to form a ring, for example, adjacent R 6 and R 6 are bonded to each other to form a condensed ring condensed to a benzene ring.

[0120] R 6Among these, a methyl group, a cyclohexyl group, a phenyl group, and a naphthyl group are preferable, a methyl group, a cyclohexyl group, and a phenyl group are more preferable, a methyl group and a phenyl group are further preferable, and a methyl group is particularly preferable.

[0121] c represents an integer of 0 to 5. Among these, c is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0122] In the above formula (Y3), R 7 , R 8 are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, or a halogen atom, provided that R 7 and / or R 8 At least two of the groups may be bonded to each other to form a ring.

[0123] In the above, the substituent is not particularly limited as long as it does not impair the effects of the present invention, but is preferably selected from an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, and a halogen atom.

[0124] R 7 , R 8 The unsubstituted or substituted alkyl group having 1 to 10 carbon atoms may be linear, branched, or cyclic. Examples of the unsubstituted or substituted alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an n-hexyl group, a cyclohexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, and an n-decyl group.

[0125] R 7 , R 8Examples of the unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms include unsubstituted phenyl and naphthyl groups. Examples of substituted aromatic hydrocarbon groups include methylphenyl (tolyl), ethylphenyl, propylphenyl, butylphenyl, dimethylphenyl, and trimethylphenyl groups. From the viewpoint of the thermal stability and heat resistance of the resin of the present invention, unsubstituted aromatic hydrocarbon groups are preferred.

[0126] R 7 , R 8 Examples of the unsubstituted or substituted acyl group having 1 to 10 carbon atoms include a methanoyl group, an ethanoyl group, a propanoyl group, a butanoyl group, a pentanoyl group, a hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, a benzoyl group, an acrylyl group, a chloroethanoyl group, a dichloroethanoyl group, a trichloroethanoyl group, a bromoethanoyl group, and a fluoroethanoyl group.

[0127] R 7 , R 8 Examples of the halogen atom include a chlorine atom, a bromine atom, and a fluorine atom.

[0128] R 7 and / or R 8 When at least two of the groups are bonded to each other to form a ring, examples include the following. (a) Adjacent R 7 and R 7 are bonded to each other to form a fused ring that is fused to a benzene ring. (b) Adjacent R 8 and R 8 are bonded to each other to form a fused ring that is fused to a benzene ring. (c) R 7 and R 8 are bonded to form a bridge structure connecting the two benzene rings in formula (Y3). Specific examples of the above (c) include -O-, -S-, and -SO 2 -, -Si-, -SiH 2 -,-SiMe 2- or -SiEt 2 -, and a bridge structure that links carbon atoms on two benzene rings.

[0129] R 7 , R 8 Among these, a methyl group, a cyclohexyl group, a phenyl group, and a naphthyl group are preferable, a methyl group, a cyclohexyl group, and a phenyl group are more preferable, a methyl group and a phenyl group are further preferable, and a methyl group is particularly preferable.

[0130] d and e each independently represent an integer of 0 to 5. Of these, d and e each independently are preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0131] The structural unit represented by the formula (3) is more preferably a structural unit represented by any one of the following formulae (3-1) to (3-5), and particularly preferably a structural unit represented by any one of the following formulae (3-6) to (3-10). Among these, the structural unit represented by any one of the following formulae (3-1), (3-2), (3-4), and (3-5) is even more preferable because the refractive index of the resin is high.

[0132] [ka]

[0133] (In formulas (3-1) to (3-5), R 1 , R 2 , a, and b are defined as in formula (3). 6 , c are defined as in formula (Y2). 7 , R 8 , d, and e are defined the same as in formula (Y2).

[0134] [ka]

[0135] The resin of the present invention may contain only one type of the structural unit (2), or may contain two or more types.

[0136] The content of the structural unit (2) in the resin of the present invention is 40% by weight or more, preferably 50% by weight or more, more preferably more than 50% by weight, even more preferably 51% by weight or more, and particularly preferably 52% by weight or more, when the total weight of the resin is 100% by weight. If the content of the structural unit (2) is equal to or more than the above lower limit, the effect of improving thermal stability and reducing birefringence due to the inclusion of the structural unit (2) can be effectively obtained. On the other hand, the content of the structural unit (2) in 100% by weight of the resin of the present invention is preferably 99% by weight or less, more preferably 95% by weight or less, even more preferably 90% by weight or less, and particularly preferably 80% by weight or less, from the viewpoint of ensuring the content of the structural unit (1).

[0137] Examples of monomers serving as resin raw materials for inducing such structural unit (2) into a resin include dihydroxy compounds represented by the following formulae (3-1A) to (3-5A). The dihydroxy compounds are particularly preferably dihydroxy compounds represented by the following formulae (3-6A) to (3-10A).

[0138] [ka]

[0139] (In formulas (3-1A) to (3-5A), R 1 , R 2 , a, and b are defined as in formula (3). 6 , c are defined as in formula (Y2). 7 , R 8 , d, and e are defined the same as in formula (Y2).

[0140] [ka]

[0141] Specific examples of the starting dihydroxy compound for inducing the structural unit (2) in the resin of the present invention include the following.

[0142] (In the structural unit (2), Ar 1 is an unsubstituted or substituted aromatic hydrocarbon group having 6 to 88 carbon atoms. Benzenediols such as hydroquinone, resorcinol, and catechol; naphthalenediols such as 1,2-dihydroxynaphthalene, 1,3-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, and 2,7-dihydroxynaphthalene;

[0143] (In the structural unit (2), Ar 1 is a divalent group having 6 to 88 carbon atoms in which an unsubstituted or substituted aromatic hydrocarbon ring is linked via a direct bond or any linking group. 1,1'-Bi-2-naphthol, 2,2'-dihydroxy-3,3'-diphenyl-1,1'-binaphthalene, 2,2'-dihydroxy-4,4'-diphenyl-1,1'-binaphthalene, 2,2'-dihydroxy-5,5'-diphenyl-1,1'-binaphthalene, 2,2'-dihydroxy-6,6'-diphenyl-1,1'-binaphthalene, 2,2'-dihydroxy-7,7'-diphenyl 2,2'-dihydroxy-8,8'-diphenyl-1,1'-binaphthalene, 2,2'-dihydroxy-3,3'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-dihydroxy-4,4'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-dihydroxy-5,5'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-dihydro 2,2'-dihydroxy-7,7'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-dihydroxy-8,8'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-dihydroxy-3,3'-di-2-naphthyl-1,1'-binaphthalene, 2,2'-dihydroxy-4,4'-di-2-naphthyl-1,1'- Compounds having a binaphthyl skeleton, such as binaphthalene, 2,2'-dihydroxy-5,5'-di-2-naphthyl-1,1'-binaphthalene, 2,2'-dihydroxy-6,6'-di-2-naphthyl-1,1'-binaphthalene, 2,2'-dihydroxy-7,7'-di-2-naphthyl-1,1'-binaphthalene, and 2,2'-dihydroxy-8,8'-di-2-naphthyl-1,1'-binaphthalene; Biphenol derivatives such as 4,4'-biphenol, 3,3'-dimethyl-4,4'-biphenol, 2,2',6,6'-tetramethylbiphenol, octamethylbiphenol, 3,3'-dichloro-4,4'-biphenol, 2,2',6,6'-tetrachlorobiphenol, octachlorobiphenol, 3,3'-dibromo-4,4'-biphenol, 2,2',6,6'-tetrabromobiphenol, octabromobiphenol, etc.;

[0144] 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 2,2-bis(4-hydroxy-3,5-diethylphenyl)propane, 2,2-bis(4-hydroxy-(3-phenyl)phenyl)propane, 2,2-bis(4-hydroxy-(3,5-diphenyl)phenyl)propane, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, bis(4-hydroxyphenyl)methane, 1,1-bis( 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxyphenyl)pentane, 2,2-bis(4-hydroxyphenyl)pentane, 1,1-bis(4-hydroxyphenyl)hexane, 1,1-bis(4-hydroxyphenyl)heptane, 1,1-bis(4-hydroxyphenyl)octane, 1,1-bis(4-hydroxyphenyl)nonane, 1,1-bis(4-hydroxyphenyl)de 1,1-bis(4-hydroxyphenyl)undecane, 1,1-bis(4-hydroxyphenyl)dodecane, 1,1-bis(4-hydroxyphenyl)tridecane, 1,1-bis(4-hydroxyphenyl)tetradecane, 1,1-bis(4-hydroxyphenyl)pentadecane, 1,1-bis(4-hydroxyphenyl)hexadecane, 1,1-bis(4-hydroxyphenyl)heptadecane, 1,1-bis(4-hydroxyphenyl)octadecane, 1,1-bis(4-hydroxyphenyl)nonadecane, 1,1-bis(4-hydroxyphenyl) 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene, 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene ...1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-3-methylcyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(4-hydroxyphenyl)cyclododecane, Aromatic bisaryl compounds having no fluorene skeleton, such as bis(4-hydroxyphenyl)sulfide, bis(4-hydroxy-3-methylphenyl)sulfide, bis(4-hydroxyphenyl)disulfide, 4,4'-dihydroxydiphenyl sulfoxide, bis(4-hydroxyphenyl)sulfone, 2,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxydiphenyl ketone, 4,4'-dihydroxy-3,3'-dichlorodiphenyl ether, 6,6'-dihydroxy-3,3,3',3'-tetramethyl-1,1'-spirobiindane, and 7,7'-dimethyl-6,6'-dihydroxy-3,3,3',3'-tetramethyl-1,1'-spirobiindane; 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene, 9,9-bis(6-hydroxy-2-naphthyl)fluorene, 9,9-bis(4-hydroxyphenyl)-1,8-diphenylfluorene, 9,9-bis(4-hydroxyphenyl)-2,7-diphenylfluorene, 9,9-bis(4-hydroxyphenyl)-3,6-diphenylfluorene, 9,9-bis(4-hydroxyphenyl)-4,5-diphenylfluorene, 9,9-bis(4-hydroxyphenyl)-1,8-di(1-naphthyl)fluorene, 9,9-bis(4-hydroxyphenyl)-2,7-di(1-naphthyl)fluorene, 9,9-bis(4-hydroxyphenyl)-2,7-di(1-naphthyl)fluorene, 9 ,9-bis(4-hydroxyphenyl)-3,6-di(1-naphthyl)fluorene, 9,9-bis(4-hydroxyphenyl)-4,5-di(1-naphthyl)fluorene, 9,9-bis(4-hydroxyphenyl)-1,8-di(2-naphthyl)fluorene, 9,9-bis(4-hydroxyphenyl)-2,7-di(2-naphthyl)fluorene, 9,9-bis(4-hydroxyphenyl)-3,6-di(2-naphthyl)fluorene, 9,9-bis(4-hydroxyphenyl)-4,5-di(2-naphthyl)fluorene, 9,9-bis(6-hydroxy-2-naphthyl)-2,7-di(2-naphthyl)fluorene, and other bisaryl compounds with a fluorene skeleton; A compound in which the fluorene skeleton of the aforementioned bisaryl compound having a fluorene skeleton is replaced with an anthrone skeleton.

[0145] These dihydroxy compounds may be used alone or in combination of two or more kinds.

[0146] Among the dihydroxy compounds for forming the structural unit (2) listed above, from the viewpoint of a balance of various physical properties such as the thermal stability, heat resistance, mechanical properties, and optical properties such as transparency, refractive index, and birefringence of the resin, preferred are compounds having a binaphthyl skeleton, biphenol derivatives, aromatic bisaryl compounds having no fluorene skeleton, bisaryl compounds having a fluorene skeleton, and compounds in which the fluorene skeleton is replaced with an anthrone skeleton, more preferred are compounds having a binaphthyl skeleton, biphenol derivatives, and aromatic bisaryl compounds having no fluorene skeleton, and even more preferred are biphenol derivatives and aromatic bisaryl compounds having no fluorene skeleton.

[0147] Examples of biphenol derivatives and aromatic bisaryl compounds having no fluorene skeleton for forming the structural unit (2) include: 4,4'-biphenol, 3,3'-dimethyl-4,4'-biphenol, 2,2',6,6'-tetramethylbiphenol, octamethylbiphenol, 3,3'-dichloro-4,4'-biphenol, 2,2',6,6'-tetrachlorobiphenol, octachlorobiphenol, 3,3'-dibromo-4,4'-biphenol, 2,2',6,6'-tetrabromobiphenol, octabromobiphenol, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 2,2-bis(4-hydroxy-3,5-diethylphenyl)propane, 2,2-bis(4-hydroxy-(3-phenyl)phenyl)propane, 2,2-bis(4-hydroxy-(3,5-diphenyl)phenyl)propane, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)butane, 2,2 -Bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxyphenyl)pentane, 2,2-bis(4-hydroxyphenyl)pentane, 1,1-bis(4-hydroxyphenyl)hexane, 1,1-bis(4-hydroxyphenyl)heptane, 1,1-bis(4-hydroxyphenyl)octane, 1,1-bis(4-hydroxyphenyl)nonane, 1,1-bis(4-hydroxyphenyl)decane, 1,1-bis(4-hydroxyphenyl)undecane, 1,1-bis(4-hydroxyphenyl)dodecane, 1,1-bis ...dodecane, 1,1-bis(4-hydroxyphenyl)tridecane, 1,1-bis(4-hydroxyphenyl)tetradecane, 1,1-bis(4-hydroxyphenyl)pentadecane, 1,1-bis(4-hydroxyphenyl)hexadecane, 1,1-bis(4-hydroxyphenyl)heptadecane, 1,1-bis(4-hydroxyphenyl)octadecane, 1,1-bis(4-hydroxyphenyl)nonadecane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bis(4-hydroxyphenyl)diphenylmethane, 2,2-bis(4-hydroxyphenyl)-4-methylpentane, 1,1-bis(4-hydroxyphenyl)-2-ethylhexane, bis(4-hydroxy-3-nitrophenyl)methane, 3,3-bis(4-hydroxyphenyl)pentane, 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene, 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene, 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl) 1,1-bis(4-hydroxyphenyl)-3-methylcyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(4-hydroxyphenyl)cyclododecane, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxy-3-methylphenyl)sulfide, bis(4-hydroxyphenyl)disulfide, 4,4'-dihydroxydiphenyl sulfoxide, bis(4-hydroxyphenyl)sulfone, and 2,4'-dihydroxydiphenyl sulfone are preferred. 4,4'-biphenol, 3,3'-dimethyl-4,4'-biphenol, 2,2',6,6'-tetramethylbiphenol, octamethylbiphenol, 3,3'-dichloro-4,4'-biphenol, 2,2',6,6'-tetrachlorobiphenol, octachlorobiphenol, 3,3'-dibromo-4,4'-biphenol, 2,2',6,6'-tetrabromobiphenol, octabromobiphenol, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 2,2- Bis(4-hydroxy-3,5-dimethylphenyl)propane, 2,2-bis(4-hydroxy-3,5-diethylphenyl)propane, 2,2-bis(4-hydroxy-(3-phenyl)phenyl)propane, 2,2-bis(4-hydroxy-(3,5-diphenyl)phenyl)propane, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxy 1,1-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxyphenyl)pentane, 2,2-bis(4-hydroxyphenyl)pentane, 1,1-bis(4-hydroxyphenyl)hexane, 1,1-bis(4-hydroxyphenyl)heptane, 1,1-bis(4-hydroxyphenyl)octane, 1,1-bis(4-hydroxyphenyl)nonane, 1,1-bis(4-hydroxyphenyl)decane, 1,1-bis(4-hydroxyphenyl)undecane, 1,1-bis(4-hydroxyphenyl)-1 -phenylethane, bis(4-hydroxyphenyl)diphenylmethane, 2,2-bis(4-hydroxyphenyl)-4-methylpentane, 1,1-bis(4-hydroxyphenyl)-2-ethylhexane, bis(4-hydroxy-3-nitrophenyl)methane, 3,3-bis(4-hydroxyphenyl)pentane, 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene, 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene, 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 1,More preferred are 1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-3-methylcyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxy-3-methylphenyl)sulfide, bis(4-hydroxyphenyl)disulfide, 4,4'-dihydroxydiphenylsulfoxide, bis(4-hydroxyphenyl)sulfone, and 2,4'-dihydroxydiphenylsulfone. 4,4'-biphenol, 3,3'-dimethyl-4,4'-biphenol, 2,2',6,6'-tetramethylbiphenol, octamethylbiphenol, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 2,2-bis(4-hydroxy-3,5-diethylphenyl)propane, 2,2-bis(4-hydroxy-(3-phenyl)phenyl)propane, 2,2-bis(4-hydroxy-(3,5-diphenyl)phenyl)propane, )phenyl)propane, bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bis(4-hydroxyphenyl)diphenylmethane, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxy-3-methylphenyl)sulfide, bis(4-hydroxyphenyl)disulfide, 4,4'-dihydroxydiphenylsulfoxide, bis(4-hydroxyphenyl)sulfone, and 2,4'-dihydroxydiphenylsulfone are more preferred, Particularly preferred are 4,4'-biphenol (hereinafter abbreviated as BP), 2,2-bis(4-hydroxyphenyl)propane (hereinafter abbreviated as BPA), 1,1-bis(4-hydroxyphenyl)-1-phenylethane (hereinafter abbreviated as BisAP), bis(4-hydroxyphenyl)diphenylmethane (hereinafter abbreviated as BisBP), and bis(4-hydroxyphenyl)sulfide (hereinafter abbreviated as BPS).

[0148] If 50 mol % or more of the dihydroxy compound used as the raw material of the structural unit (2) is selected from BP, BPA, BisAP, BisBP, and BPS, the dihydroxy compound is easy to use from the standpoint of both safety and cost, and the resulting resin has a good balance of various physical properties such as thermal stability, heat resistance, mechanical properties, optical properties, etc. Among them, BP, BisAP, BisBP, and BPS are more preferable because the refractive index of the resin is high, BPA and BisAP are preferable because the birefringence of the resin is small, and BP, BPA, and BisAP are preferable because the coloring of the resin is small.

[0149] <Other structural units> The resin of the present invention may contain structural units other than the structural unit (1) and the structural unit (2) (hereinafter, sometimes referred to as "other structural units"), and examples of monomers that form other structural units in the resin include aliphatic dihydroxy compounds, alicyclic dihydroxy compounds, dihydroxy compounds containing a condensed ring structure, dihydroxy compounds containing an acetal ring, oxyalkylene glycols, dihydroxy compounds containing an aromatic component, diester compounds, etc. Among these, dihydroxy compounds containing an aromatic component are preferred from the viewpoint of increasing the reaction efficiency.

[0150] (Aliphatic dihydroxy compounds) As the aliphatic dihydroxy compound, for example, the following dihydroxy compounds can be used. Dihydroxy compounds of straight-chain aliphatic hydrocarbons such as ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 1,5-heptanediol, 1,6-hexanediol, 1,9-nonanediol, 1,10-decanediol, and 1,12-dodecanediol; dihydroxy compounds of branched aliphatic hydrocarbons such as neopentyl glycol and hexylene glycol.

[0151] (alicyclic dihydroxy compounds) As the alicyclic dihydroxy compound, for example, the following dihydroxy compounds can be used. dihydroxy compounds which are primary alcohols of alicyclic hydrocarbons, exemplified by dihydroxy compounds derived from terpene compounds such as 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, tricyclodecane dimethanol, pentacyclopentadecane dimethanol, 2,6-decalin dimethanol, 1,5-decalin dimethanol, 2,3-decalin dimethanol, 2,3-norbornane dimethanol, 2,5-norbornane dimethanol, 1,3-adamantanedimethanol, and limonene; Dihydroxy compounds which are secondary and tertiary alcohols of alicyclic hydrocarbons, such as 1,2-cyclohexanediol, 1,4-cyclohexanediol, 1,3-adamantanediol, hydrogenated bisphenol A, and 2,2,4,4-tetramethyl-1,3-cyclobutanediol.

[0152] (Dihydroxy Compounds Containing a Fused Ring Structure) As the dihydroxy compound containing a condensed ring structure, for example, a dihydroxy compound represented by the following formula (IA), exemplified by isosorbide (ISB), isomannide, isoidet, etc., can be used.

[0153] [ka]

[0154] (Dihydroxy compounds containing an acetal ring) Examples of the dihydroxy compound containing an acetal ring include spiro glycol represented by the following formula (IB), dioxane glycol represented by the following formula (IC), and a dihydroxy compound derived from inositol represented by the following formula (ID).

[0155] [ka]

[0156] (In the above formula (ID), R 20 and R 21 each independently represents an organic group having 1 to 30 carbon atoms. These organic groups may have any substituent.)

[0157] In the above formula (ID), preferably R 20 and R 21 R is an organic group having 1 to 30 carbon atoms which may have a substituent. 20 and R 21 Examples of the organic group having 1 to 30 carbon atoms which may have a substituent include alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; straight-chain or branched chain alkenyl groups such as a vinyl group, a propenyl group, and a hexenyl group; cyclic alkenyl groups such as a cyclopentenyl group and a cyclohexenyl group; alkynyl groups such as an ethynyl group, a methylethynyl group, and a 1-propionyl group; aryl groups such as a phenyl group, a naphthyl group, and a toluyl group; alkoxyphenyl groups such as a methoxyphenyl group; aralkyl groups such as a benzyl group and a phenylethyl group; and heterocyclic groups such as a thienyl group, a pyridyl group, and a furyl group. Among these, from the viewpoint of the stability of the resin, alkyl groups, cycloalkyl groups, aryl groups, aralkyl groups, etc. are preferred, and from the viewpoint of the balance between the optical properties, weather resistance, heat resistance, and mechanical properties of the resin, alkyl groups and cycloalkyl groups are particularly preferred.

[0158] (Oxyalkylene glycols) As the oxyalkylene glycol, for example, the following dihydroxy compounds can be used. Diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, polypropylene glycol.

[0159] (Dihydroxy compounds containing aromatic components) As the dihydroxy compound containing an aromatic component, for example, the following dihydroxy compounds can be used. 2,2-bis(4-(2-hydroxyethoxy)phenyl)propane, 2,2-bis(4-(2-hydroxypropoxy)phenyl)propane, 1,3-bis(2-hydroxyethoxy)benzene, 4,4'-bis(2-hydroxyethoxy)biphenyl, bis(4-(2-hydroxyethoxy)phenyl)sulfone, 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene, 9,9-bis(2-(2-hydroxyethoxy)naphthyl)fluorene, 2,2'-bis(2-hydroxyethoxy)-3,3'-dimethyl-1,1'-biphenyl Dihydroxy compounds having an ether group bonded to an aromatic group, such as naphthalene, 2,2'-bis(2-hydroxyethoxy)-6,6'-dimethyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-7,7'-dimethyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-3,3'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-6,6'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-7,7'-diphenyl-1,1'-binaphthalene, etc.:

[0160] As dihydroxy compounds containing an aromatic component that form other structural units, 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene and 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene are preferred in terms of the balance between optical properties, thermal properties, and raw material costs.

[0161] (Diester Compound) As the diester compound, for example, the following dicarboxylic acids can be used. Aromatic dicarboxylic acids such as terephthalic acid, phthalic acid, isophthalic acid, 4,4'-diphenyldicarboxylic acid, 4,4'-diphenyletherdicarboxylic acid, 4,4'-benzophenonedicarboxylic acid, 4,4'-diphenoxyethanedicarboxylic acid, 4,4'-diphenylsulfonedicarboxylic acid, and 2,6-naphthalenedicarboxylic acid; Alicyclic dicarboxylic acids such as 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, and decalin-2,6-dicarboxylic acid; aliphatic dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid; These dicarboxylic acid components can be used as raw materials for polyester carbonate as dicarboxylic acid itself, but depending on the production method, dicarboxylic acid esters such as methyl esters and phenyl esters, and dicarboxylic acid derivatives such as dicarboxylic acid halides can also be used as raw materials. Since the polymerization reactivity of diester compounds is relatively low, from the viewpoint of increasing the reaction efficiency, it is preferable to use less other diester compounds, excluding carbonate esters and diester compounds having an oligofluorene structure unit.

[0162] The dihydroxy compounds and diester compounds for forming the other structural units may be used alone or in combination of two or more kinds depending on the required performance of the resulting resin.

[0163] From the viewpoint of more reliably obtaining the effects of the present invention by containing the structural units (1) and (2), the resin of the present invention, including cases in which other structural units are contained, preferably contains the structural units (1) and (2) in the above-mentioned suitable contents so that the total content of the structural units (1) and (2) in 100% by weight of the resin is 80% by weight or more, particularly 90% by weight or more, and furthermore 95 to 100% by weight. Thus, in the resin of the present invention, it is preferable that the content of other structural units is small, and if the content is high, the thermal stability of the resin may be reduced.

[0164] <Carbonate diester> The carbonate bond, which is a linking group contained in the polycarbonate resin or polyester carbonate resin, which is a preferred embodiment of the resin of the present invention, is introduced by polymerizing a carbonate diester represented by the following formula (4).

[0165] [ka]

[0166] (In formula (4), A 3 and A 4 each represents an aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, 3 and A 4 may be the same or different.)

[0167] A 3 and A 4 is preferably a substituted or unsubstituted aromatic hydrocarbon group, more preferably an unsubstituted aromatic hydrocarbon group. Examples of the substituent of the aliphatic hydrocarbon group include an ester group, an ether group, a carboxylic acid, an amide group, and a halogen atom, and examples of the substituent of the aromatic hydrocarbon group include an alkyl group such as a methyl group or an ethyl group.

[0168] Examples of the carbonic acid diester represented by the formula (4) include diphenyl carbonate (hereinafter sometimes abbreviated as DPC), substituted diphenyl carbonate such as ditolyl carbonate, and dialkyl carbonate such as dimethyl carbonate, diethyl carbonate, and di-tert-butyl carbonate, with diphenyl carbonate and substituted diphenyl carbonate being preferred, and diphenyl carbonate being particularly preferred.

[0169] The carbonate diester may contain impurities such as chloride ions, which may inhibit the polymerization reaction or deteriorate the hue of the resulting resin. Therefore, it is preferable to use a diester that has been purified, as necessary, by distillation or the like.

[0170] In addition, when a polymerization reaction is carried out using both the diester compound represented by the formula (11) and the carbonic acid diester represented by the formula (4), 1 , A 2 and A in the formula (4) 3 , A 4 If all of the A have the same structure, the components released during the polymerization reaction are the same, making it easier to recover and reuse the components. 1 ~A 4 is particularly preferably a phenyl group. 1 ~A 4 When is a phenyl group, the component which is eliminated during the polymerization reaction is phenol.

[0171] When the resin of the present invention has a carbonate structural unit derived from a carbonate diester represented by formula (4), the content of the carbonate structural unit in 100% by weight of the resin of the present invention is preferably 20% by weight or less, particularly 11% by weight or less, and especially 6% by weight or less, from the viewpoint of improving the refractive index of the resin and reducing birefringence while ensuring the necessary amounts of structural units (1) and (2). On the other hand, from the viewpoint of improving the thermal stability of the resin, the content of the carbonate structural unit is preferably 0.1% by weight or more, particularly 0.7% by weight or more, and especially 2.0% by weight or more.

[0172] <Resin characteristics> The resin of the present invention contains the structural unit (2) in an appropriate ratio, which improves thermal stability and reduces birefringence, and contains the structural unit (1), which improves melt fluidity while maintaining high heat resistance and a high refractive index, thereby also reducing birefringence of the molded article.

[0173] The reduced viscosity (η sp / C) is preferably 0.15 or more and 1.20 or less, more preferably 0.17 or more and 0.72 or less, and even more preferably 0.20 or more and 0.60 or less. If the reduced viscosity is equal to or more than the lower limit, the thermal stability, heat resistance, and mechanical strength of the resin are good, and if it is equal to or less than the upper limit, the melt viscosity of the resin is low, the injection moldability is excellent, and the birefringence of the molded product is low.

[0174] The reduced viscosity of the resin is measured by the method described in the Examples section below.

[0175] The refractive index (n D ) is preferably 1.59 or more, more preferably 1.60 or more and 1.70 or less, and even more preferably 1.61 or more and 1.66 or less. If the refractive index is 1.59 or more, the added value of the resin is high when it is used as an optical member such as a lens. In order to obtain a resin with a refractive index exceeding 1.70, it is necessary to excessively increase the content of aromatic rings or the content of S element in the resin of the present invention, and there is a risk that the Tg of the resin becomes excessively high, the thermal stability of the resin decreases, or the mold contamination tendency increases.

[0176] The Abbe number (ν D ) is preferably 35.0 or less, more preferably 11.0 or more and 32.0 or less, and even more preferably 16.0 or more and 27.0 or less. If the Abbe number is small, it is useful as a material for aberration-correcting low Abbe number concave lens used in combination with a high Abbe number convex lens such as COP (cycloolefin polymer).

[0177] Here, the refractive index is rounded off to the third decimal place, and the Abbe number is rounded off to the first decimal place. The refractive index and Abbe number of the resin are measured by the method described in the Examples section below.

[0178] The resin of the present invention preferably has an in-plane orientation birefringence of -0.0010 or more and 0.0020 or less at a wavelength of 550 nm when produced from the resin in a stretched film. If the orientation birefringence of the stretched film is -0.0010 or more, the birefringence of the molded article made of the resin is reduced. On the other hand, if the orientation birefringence of the stretched film is 0.0020 or less, the birefringence of the molded article made of the resin is reduced. The orientation birefringence is more preferably -0.0010 or more and 0.0010 or less, and even more preferably -0.0004 or more and 0.0004 or less.

[0179] The in-plane orientation birefringence of the stretched film at a wavelength of 550 nm is measured by the method described in the Examples section below.

[0180] The resin of the present invention has a high glass transition temperature (Tg) and is excellent in heat resistance. The Tg of the resin of the present invention is preferably 110° C. or higher, more preferably 120° C. or higher, and even more preferably 130° C. or higher. On the other hand, from the viewpoint of ensuring good moldability, the Tg of the resin of the present invention is preferably 250° C. or lower, more preferably 230° C. or lower, and even more preferably 200° C. or lower. The glass transition temperature of the resin of the present invention can be easily adjusted to a range that allows both high heat resistance and good moldability by appropriately selecting the structure and content of the structural unit (2) at will, and therefore the resin of the present invention is suitable for applications that are expected to be exposed to high temperature environments, such as in-vehicle optical lenses.

[0181] The glass transition temperature (Tg) of the resin is measured by the method described in the Examples section below.

[0182] The 1% thermal weight loss temperature (Td) of the resin of the present invention under nitrogen is preferably 355°C or higher, more preferably 356°C or higher, and even more preferably 363°C or higher. The higher the 1% thermal weight loss temperature, the higher the thermal stability and the higher the endurance for use at high temperatures. In addition, the manufacturing temperature can be increased, and the control range during manufacturing can be wider, making manufacturing easier. On the other hand, the lower the 1% thermal weight loss temperature under nitrogen, the lower the thermal stability and the more difficult it is to use at high temperatures. In addition, the control range during manufacturing becomes narrower, making manufacturing more difficult. There is no particular limit to the upper limit of the 1% thermal weight loss temperature under nitrogen.

[0183] The 1% thermal weight loss temperature (Td) of the resin under nitrogen is measured by the method described in the Examples section below.

[0184] [Resin manufacturing method] The polyester resin and polyester carbonate resin of the present invention can be produced by a commonly used polymerization method. For example, they can be produced by a solution polymerization method or an interfacial polymerization method using phosgene or a carboxylic acid halide, or a melt polymerization method in which a reaction is carried out without using a solvent. Among these production methods, it is preferable to produce them by the melt polymerization method, which does not use a solvent or a highly toxic compound, thereby reducing the environmental load and is also excellent in productivity.

[0185] When a solvent is used in polymerization, the solvent may remain in the resin, and the plasticizing effect of the solvent may lower the glass transition temperature of the resin, which may cause quality fluctuations in processing steps such as molding and stretching, which will be described later. In addition, halogen-based organic solvents such as methylene chloride are often used as solvents, and if halogen-based solvents remain in the resin, they may cause corrosion of metal parts when a molded product using this resin is incorporated into an electronic device, etc. Resins obtained by melt polymerization do not contain solvents, which is also advantageous for stabilizing processing steps and product quality.

[0186] When producing a resin by melt polymerization, a monomer having the structural unit described above, a carbonic acid diester, and a polymerization catalyst are mixed and subjected to an ester exchange reaction (also called a polycondensation reaction) under molten conditions, and the reaction rate is increased while removing the elimination components from the system. At the end of the polymerization, the reaction is allowed to proceed under high temperature and high vacuum conditions until the desired molecular weight is reached. When the reaction is complete, the molten resin is removed from the reactor, and the resin of the present invention is obtained.

[0187] In the polycondensation reaction, the reaction rate and the molecular weight of the resulting resin can be controlled by strictly adjusting the molar ratio of all dihydroxy compounds and all diester compounds used in the reaction. The molar ratio of the total amount of the carbonate diester and all diester compounds to the total dihydroxy compounds is preferably adjusted to 0.90 to 1.30, more preferably adjusted to 0.96 to 1.20, and particularly preferably adjusted to 0.98 to 1.10.

[0188] If the molar ratio is too far above or below the range, it is not possible to produce a resin with the desired molecular weight. If the molar ratio is too small, the number of hydroxyl group terminals in the produced resin increases, which may deteriorate the thermal stability of the resin. In addition, a large amount of unreacted dihydroxy compound remains in the resin, which may cause dirt on the molding machine and poor appearance of the molded product in the subsequent molding process. On the other hand, if the molar ratio is too large, the rate of transesterification reaction may decrease under the same conditions, or the amount of remaining carbonic acid diester or diester compound in the produced resin may increase, and these remaining low molecular weight components may also cause problems in the molding process.

[0189] The melt polymerization method is usually carried out in a multi-stage process of two or more stages. The polycondensation reaction may be carried out in two or more stages using one polymerization reactor by sequentially changing the conditions, or may be carried out in two or more stages using two or more reactors by changing the conditions for each stage, but from the viewpoint of production efficiency, it is carried out using two or more, preferably three or more reactors. The polycondensation reaction may be carried out in a batch system, a continuous system, or a combination of a batch system and a continuous system, but from the viewpoint of production efficiency and stability of quality, a continuous system is preferred.

[0190] In polycondensation reactions, it is important to properly control the balance between temperature and pressure in the reaction system. If either the temperature or pressure is changed too quickly, unreacted monomers may be distilled out of the reaction system. As a result, the molar ratio of dihydroxy compounds and diester compounds may change, and a resin with the desired molecular weight may not be obtained. In addition, the polymerization rate of the polycondensation reaction is controlled by the balance between the hydroxyl group terminal and the ester group terminal or carbonate group terminal. Therefore, particularly when polymerization is performed in a continuous manner, if the balance of the terminal groups fluctuates due to the distillation of unreacted monomers, it becomes difficult to control the polymerization rate at a constant rate, and the molecular weight of the resulting resin may fluctuate greatly. Since the molecular weight of a resin correlates with the melt viscosity, when the resulting resin is molded, the melt viscosity may fluctuate, leading to problems such as failure to obtain molded products of uniform dimensions.

[0191] Furthermore, if unreacted monomers are distilled off, not only the balance of the terminal groups but also the copolymerization composition of the resin may deviate from the desired composition, which may affect the mechanical properties and optical properties. Since the optical properties of the resin of the present invention, such as the birefringence and refractive index, are controlled by the ratio of the structural unit (1) to the structural unit (2) in the resin, if the ratio is disturbed during the polycondensation reaction, the optical properties as designed may not be obtained.

[0192] Hereinafter, the melt polycondensation reaction process will be described separately into a stage in which a monomer is consumed to produce an oligomer, and a stage in which polymerization is allowed to proceed up to a desired molecular weight to produce a polymer. Specifically, the following conditions can be adopted as reaction conditions in the first-stage reaction. That is, the internal temperature of the polymerization reactor is set in the range of usually 100° C. or more, preferably 150° C. or more, more preferably 170° C. or more, and usually 250° C. or less, preferably 240° C. or less, more preferably 230° C. or less. The pressure of the polymerization reactor is set in the range of usually 70 kPa or less (hereinafter, pressure refers to absolute pressure), preferably 50 kPa or less, more preferably 30 kPa or less, and usually 1 kPa or more, preferably 3 kPa or more, more preferably 5 kPa or more. The reaction time is set in the range of usually 0.1 hours or more, preferably 0.5 hours or more, and usually 10 hours or less, preferably 5 hours or less, more preferably 3 hours or less.

[0193] The first-stage reaction is carried out while the monohydroxy compound derived from the diester compound generated is distilled out of the reaction system. For example, when diphenyl carbonate is used as the carbonic acid diester, the monohydroxy compound distilled out of the reaction system in the first-stage reaction is phenol. In the first stage reaction, the lower the reaction pressure, the more the polymerization reaction can be accelerated, but on the other hand, the more unreacted monomers are distilled off. In order to simultaneously suppress the distillation of unreacted monomers and accelerate the reaction by reducing the pressure, it is effective to use a reactor equipped with a reflux condenser. It is especially good to use a reflux condenser in the early stages of the reaction when there is a lot of unreacted monomers.

[0194] In the second stage reaction, the pressure of the reaction system is gradually lowered from the pressure of the first stage, and the monohydroxy compound generated is removed from the reaction system, and the pressure of the reaction system is finally set to 5 kPa or less, preferably 3 kPa or less, more preferably 1 kPa or less. The internal temperature is usually set to 210°C or more, preferably 220°C or more, and usually 300°C or less, preferably 290°C or less, more preferably 260°C or less. The reaction time is usually set to 0.1 hours or more, preferably 0.5 hours or more, more preferably 1 hour or more, and usually 10 hours or less, preferably 5 hours or less, more preferably 3 hours or less. In order to suppress coloration and thermal deterioration and obtain a resin with good hue and thermal stability, the maximum internal temperature in all reaction stages is set to 270°C or less, preferably 265°C or less, more preferably 260°C or less.

[0195] The transesterification catalyst (hereinafter, sometimes simply referred to as catalyst or polymerization catalyst) that can be used during polymerization can have a very large effect on the reaction rate and the color tone and thermal stability of the resin obtained by polycondensation. The catalyst used is not limited as long as it can satisfy the transparency, hue, heat resistance, thermal stability, and mechanical strength of the produced resin, and includes basic compounds such as metal compounds of Group 1 or Group 2 (hereinafter, simply referred to as "Group 1" and "Group 2") in the long-form periodic table, basic boron compounds, basic phosphorus compounds, basic ammonium compounds, and amine-based compounds. At least one metal compound selected from the group consisting of metals of Group 2 of the long-form periodic table, lithium, and cesium is preferably used.

[0196] As the Group 1 metal compound, for example, the following compounds can be used, but other Group 1 metal compounds can also be used: sodium hydroxide, potassium hydroxide, lithium hydroxide, cesium hydroxide, sodium hydrogen carbonate, potassium hydrogen carbonate, lithium hydrogen carbonate, cesium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, sodium acetate, potassium acetate, lithium acetate, cesium acetate, sodium stearate, potassium stearate, lithium stearate, cesium stearate, sodium borohydride, potassium borohydride, lithium borohydride, cesium borohydride, sodium tetraphenylborate, tetraphenylborate, potassium tetraphenylborate, lithium tetraphenylborate, cesium tetraphenylborate, sodium benzoate, potassium benzoate, lithium benzoate, cesium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, dicesium hydrogen phosphate, disodium phenylphosphate, dipotassium phenylphosphate, dilithium phenylphosphate, dicesium phenylphosphate, sodium, potassium, lithium, cesium alcoholates, phenolates, disodium salts, dipotassium salts, dilithium salts, and dicesium salts of bisphenol A. Of these, from the viewpoints of polymerization activity and the hue of the obtained resin, it is preferable to use lithium compounds and cesium compounds.

[0197] As the Group 2 metal compound, for example, the following compounds can be used, but other Group 2 metal compounds can also be used. Calcium hydroxide, barium hydroxide, magnesium hydroxide, strontium hydroxide, calcium hydrogen carbonate, barium hydrogen carbonate, magnesium hydrogen carbonate, strontium hydrogen carbonate, calcium carbonate, barium carbonate, magnesium carbonate, strontium carbonate, calcium acetate, barium acetate, magnesium acetate, strontium acetate, calcium stearate, barium stearate, magnesium stearate, strontium stearate. Among these, magnesium compounds, calcium compounds, and barium compounds are preferably used, and from the viewpoint of polymerization activity and the hue of the obtained resin, magnesium compounds and / or calcium compounds are more preferably used, and calcium compounds are most preferably used.

[0198] It is also possible to use, in combination with the Group 1 metal compound and / or Group 2 metal compound, a basic compound such as a basic boron compound, a basic phosphorus compound, a basic ammonium compound, or an amine compound as an auxiliary, but it is particularly preferable to use at least one metal compound selected from the group consisting of metals in Group 2 of the long form periodic table, lithium, and cesium. The amount of the polymerization catalyst is usually 0.1 μmol to 300 μmol, preferably 0.5 μmol to 200 μmol per mol of the total dihydroxy compounds used in the polymerization. When at least one metal compound selected from the group consisting of metals of Group 2 of the long periodic table, lithium, and cesium is used as the polymerization catalyst, particularly when a magnesium compound and / or a calcium compound and / or a cesium compound is used, the amount of the polymerization catalyst is usually 0.1 μmol or more, preferably 0.3 μmol or more, and particularly preferably 0.5 μmol or more per mol of the total dihydroxy compounds. The amount of the polymerization catalyst is preferably 200 μmol or less, preferably 100 μmol or less, and particularly preferably 50 μmol or less.

[0199] In addition, when a polyester resin or a polyester carbonate resin is produced using a diester compound as a monomer, a transesterification catalyst such as a titanium compound, a tin compound, a germanium compound, an antimony compound, a zirconium compound, a lead compound, an osmium compound, a zinc compound, or a manganese compound can be used in combination with or without the basic compound. The amount of these transesterification catalysts used is usually within a range of 1 μmol to 1 mmol, preferably 5 μmol to 800 μmol, and particularly preferably 10 μmol to 500 μmol, in terms of the metal amount, relative to 1 mol of the total dihydroxy compounds used in the reaction.

[0200] If the amount of catalyst is too small, the polymerization rate will be slow, and the polymerization temperature will have to be increased accordingly to obtain a resin with the desired molecular weight. This will increase the possibility that the color of the resulting resin will deteriorate, and the unreacted raw materials will volatilize during polymerization, causing the molar ratio of the dihydroxy compound and the diester compound to be disrupted, and the desired molecular weight may not be achieved. On the other hand, if the amount of polymerization catalyst used is too large, undesirable side reactions will occur, which may cause the color of the resulting resin to deteriorate, or the resin to become discolored or decomposed during molding.

[0201] Among the group 1 metals, sodium and potassium may adversely affect the color if contained in a large amount in the resin. These metals may be mixed not only from the catalyst used but also from the raw materials and reaction equipment. Regardless of the source, the total amount of compounds of these metals in the resin is preferably 2 μmol or less, preferably 1 μmol or less, more preferably 0.5 μmol or less per 1 mol of the total dihydroxy compounds.

[0202] After the resin of the present invention is polymerized as described above, it can usually be cooled and solidified, and pelletized with a rotary cutter, etc. The method of pelletization is not limited, but examples include a method of withdrawing the resin in a molten state from the final polymerization reactor, cooling and solidifying it in the form of a strand, and pelletizing it, a method of supplying the resin in a molten state from the final polymerization reactor to a single-screw or twin-screw extruder, melt-extruding it, and then cooling and solidifying it to pelletize it, and a method of withdrawing the resin in a molten state from the final polymerization reactor, cooling and solidifying it in the form of a strand, pelletizing it once, and then supplying the resin again to a single-screw or twin-screw extruder, melt-extruding it, and then cooling and solidifying it to pelletize it.

[0203] Since the resin of the present invention is preferably used for optical applications, it is preferable that the resin contains little foreign matter. In order to remove foreign matter such as scorch and gel from the resin obtained by melt polycondensation, it is preferable to perform filtration using a filter. In particular, it is preferable to remove residual monomers, by-product phenol, etc. by devolatilization under reduced pressure, and to mix additives such as heat stabilizers and mold release agents, by melt extruding the resin using the above-mentioned vented twin-screw extruder, and then filtering it with a filter.

[0204] The filter may be of any known form, such as a candle type, a pleated type, or a leaf disk type. The aperture of the filter is preferably 50 μm or less, more preferably 40 μm or less, and even more preferably 20 μm or less, in terms of 99% filtration accuracy. When it is particularly desired to reduce foreign matter, the aperture of the filter is preferably 10 μm or less, but if the aperture is small, the pressure loss in the filter increases, which may lead to damage to the filter or deterioration of the resin due to shear heat, so that the aperture is preferably 1 μm or more in terms of 99% filtration accuracy. The aperture of the filter referred to here is determined in accordance with ISO16889.

[0205] The resin filtered through the filter is discharged from the die head in the form of strands, cooled and solidified, and pelletized with a rotary cutter or the like. When the resin is stranded or pelletized in direct contact with the outside air, it is preferable to use a JIS B It is desirable to carry out the experiment in a clean room with a cleanliness level of Class 7, or more preferably Class 6, as defined in IEC 602609-2002.

[0206] In pelletizing, it is preferable to use cooling methods such as air cooling and water cooling, and it is preferable to use air that has been previously removed of foreign matter in the air using a HEPA filter or the like to prevent reattachment of foreign matter in the air. When using water cooling, it is preferable to use water that has been removed of metals in the water using an ion exchange resin or the like and further removed of foreign matter in the water using a water filter. The mesh size of the water filter used is preferably 10 to 0.45 μm, which is a filtration accuracy for removing 99% of the particles.

[0207] The resin of the present invention is at least one resin selected from the group consisting of polyester carbonates and polyesters, containing a structural unit represented by formula (1) and a structural unit represented by formula (2), and containing 40% by weight or more of the structural unit represented by the following formula (2) when the total weight of the resin is taken as 100% by weight. The above-mentioned structural units (1) and (2) may not all be contained in the same polymer molecule. That is, as long as the above-mentioned structural units are contained in a specific amount in the entirety of a plurality of polymer molecules, the resin of the present invention may be a blend resin composed of two or more types of resins. For example, the resin containing both the above-mentioned structural units (1) and (2) may be one or more copolymers containing both the structural units (1) and (2), or may be a mixture of one or more homopolymers or copolymers containing the structural unit (1) and one or more homopolymers or copolymers containing the structural unit (2).

[0208] [Resin composition] The resin composition of the present invention is a mixture of the resin of the present invention with known additives and / or resins other than the resin of the present invention (hereinafter sometimes referred to as "other resins").

[0209] The additives may be any known additives without particular limitation as long as they do not impair the excellent physical properties of the resin of the present invention. Examples of the additives include various additives exemplified as additives that may be contained in the molded product of the present invention described below, and among them, at least one selected from the group consisting of heat stabilizers, antioxidants, ultraviolet absorbers, brightness enhancers, dyes, pigments, mold release agents, flow modifiers, and impact resistance improvers may be used.

[0210] Furthermore, the resin composition of the present invention may contain other resins as long as the excellent physical properties of the resin of the present invention are not impaired. Other resins include thermoplastic polyester resins such as polycarbonate resin, polyester resin, polyester carbonate resin, polyethylene terephthalate resin, polytrimethylene terephthalate, and polybutylene terephthalate resin; styrene-based resins such as polystyrene resin, high impact polystyrene resin (HIPS), acrylonitrile-styrene copolymer (AS resin), acrylonitrile-styrene-acrylic rubber copolymer (ASA resin), and acrylonitrile-ethylene propylene rubber-styrene copolymer (AES resin); polyolefin resins such as polyethylene resin and polypropylene resin; polyamide resin; polyimide resin; polyetherimide resin; polyurethane resin; polyphenylene ether resin; polyphenylene sulfide resin; polysulfone resin; and polymethacrylate resin.

[0211] The other resins may be contained either alone or in any combination and ratio of two or more kinds.

[0212] [Molded body] The molded article of the present invention can be produced by molding a material containing the resin of the present invention or the resin composition of the present invention.

[0213] The shape of the molded article of the present invention is not particularly limited, and examples thereof include a one-dimensional structure (e.g., a line shape, a thread shape, etc.), a two-dimensional structure (e.g., a film shape, a sheet shape, a plate shape, etc.), and a three-dimensional structure (e.g., a concave or convex lens shape, a rod shape, a hollow shape (tube shape), etc.).

[0214] The molded article of the present invention may contain various additives [for example, fillers or reinforcing agents, colorants (for example, dyes and pigments), conductive agents, flame retardants, plasticizers, lubricants, stabilizers (for example, antioxidants, ultraviolet absorbers, heat stabilizers, etc.), release agents, antistatic agents, dispersants, flow control agents, leveling agents, antifoaming agents, surface modifiers, stress reducing agents (for example, silicone oils, silicone rubbers, various plastic powders, various engineering plastic powders, etc.), carbon materials, etc.]. These additives may be used alone or in combination of two or more.

[0215] The molded article of the present invention can be produced by, for example, injection molding, injection compression molding, extrusion molding, transfer molding, blow molding, pressure molding, casting molding, or the like.

[0216] When the molded article of the present invention is produced by such a molding method, the maximum temperature during molding is preferably 400°C or less, more preferably 380°C or less, and even more preferably 360°C or less. If molding is performed at a temperature exceeding the upper limit, bubbles or coloring may occur in the obtained molded article. The maximum temperature during molding is preferably 240°C or more, more preferably 250°C or more, and even more preferably 260°C or more. At a temperature below the lower limit, the fluidity during molding is low, and filling into the mold may be insufficient. The resin of the present invention has high thermal stability and an orientation birefringence close to 0, so that a molded article with low birefringence can be obtained at a wide range of molding temperatures.

[0217] The molded article of the present invention has excellent heat resistance and optical properties (high refractive index, low birefringence, etc.), and can therefore be used as optical members such as optical films, optical lenses, and optical sheets.

[0218] In particular, the resin of the present invention is suitable for injection molding like conventional polycarbonate lenses having BPA as a polymerization component and polycarbonate lenses having BPEF as a polymerization component, and is therefore useful for forming optical lenses. Optical lenses are not particularly limited, but include in-vehicle lenses, eyeglass lenses, pickup lenses, camera lenses, microarray lenses, projector lenses, and Fresnel lenses. In particular, the resin of the present invention has high heat resistance, and can be suitably used even in applications where use in high-temperature environments is expected, such as in-vehicle optical lenses. EXAMPLES

[0219] The present invention will be described in more detail below with reference to synthesis examples and examples, but the present invention is not limited to the following examples.

[0220] The physical properties of the resins produced in the following Examples and Comparative Examples were evaluated by the following methods.

[0221] (1) Composition ratio of structural units in resin The composition ratio of the structural units in the resin was calculated from the composition ratio of each monomer charged during the production of the resin. Another method is to dissolve the resin in deuterated chloroform. 1 The composition ratio can be calculated by measuring H-NMR. Specifically, a resin-d2 chloroform solution is prepared so that the resin concentration is 30 mg / mL, and measurements are performed at 30°C with a relaxation time of 5 seconds and an accumulation count of 128. As an alternative method, the composition ratio can be calculated by subjecting the resin to hydrolysis and measuring the resulting reaction solution by liquid chromatography. The specific method is as follows. Dissolve 0.5 g of resin in 5 mL of dichloromethane. Add 45 mL of methanol and then 5 mL of 25% aqueous sodium hydroxide solution. Heat and reflux at 75°C for 30 minutes while stirring. After cooling, add 7 mL of 17.5% hydrochloric acid and then adjust the volume to 100 mL with methanol and pure water. Measure the adjusted solution using a high-performance liquid chromatograph equipped with an analytical column and detector.

[0222] (2) Reduced Viscosity The resin sample was dissolved in methylene chloride to prepare a resin solution with a precise concentration of 0.6 g / dL. The measurement was performed at a temperature of 20.0°C ± 0.1°C using a Ubbelohde type viscometer manufactured by Moritomo Rika Kogyo Co., Ltd., and the solvent passing time t 0 The time t of the solution passing through the solution was measured. 0 Using the value of and t, the relative viscosity η is calculated using the following formula (i): rel The relative viscosity η rel Using the following formula (ii), the specific viscosity η sp asked for. η rel =t / t 0 (i) η sp =(η - η 0 ) / η 0 = η rel -1 (ii) Then, the obtained specific viscosity η sp Divide by the concentration c [g / dL] to get the reduced viscosity η sp I asked for / c.

[0223] (3) Glass transition temperature (Tg) Using a differential scanning calorimeter DSC6220 manufactured by SII Nanotechnology, about 10 mg of the resin sample was heated at a heating rate of 20°C / min to measure the calorific value, and the extrapolated glass transition onset temperature was determined according to JIS K7121, which is the temperature at the intersection of a straight line extending the low-temperature side baseline to the high-temperature side and a tangent drawn at the point where the gradient of the curve of the stepwise change in the glass transition is maximum. The extrapolated glass transition temperature was defined as the glass transition temperature (Tg).

[0224] (4) 1 %Thermogravimetric reduction temperature (Td) Using a TG / DTA7200 manufactured by SII Nanotechnology, approximately 10 mg of the resin sample was placed in a container and measured under a nitrogen atmosphere (nitrogen flow rate 200 ml / min) from 30°C to 500°C at a heating rate of 10°C / min, and the temperature (Td) at which the weight decreased by 1% was determined.

[0225] (5) Film Forming Approximately 5 g of the resin sample was vacuum-dried at 100°C for more than 2 hours, and then pressed in a heat press with a spacer measuring 150 mm wide, 150 mm long, and 0.1 mm thick at a heat press temperature of 200-260°C, preheated for 1-3 minutes, and pressurized at a pressure of 20 MPa for 1 minute. The sample was then removed together with the spacer and cooled at room temperature to produce a film with a thickness of 100 μm.

[0226] (6) Refractive index (n D ), Abbe number (ν D ) A rectangular test piece 40 mm long and 8 mm wide was cut out from the film prepared by the method (5) to prepare a measurement sample. The refractive index, n C , n D , n F The measurements were performed at 20°C using monobromonaphthalene or a methylene iodide sulfur solution as the interface liquid. Abbe number ν D was calculated using the following formula (iii): ν D =(1-n D ) / (n C -n F ) (iii)

[0227] (7) Preparation of stretched film (5) Cut a piece of film 100 mm long and 70 mm wide from the film produced by method (5). Batch type biaxial stretching device (Island Industrial Co., Ltd. biaxial stretching device BIX-277-AL) ) was used, and the stretching speed was 300% / min, the stretching ratio was 1.5 times, and the stretching temperature was the glass transition temperature of the resin. The free end of the film piece was uniaxially stretched at a transfer temperature of +15°C to produce a stretched film. Ta.

[0228] (8) Measurement of orientation birefringence (Δn) of stretched film The central portion of the stretched film produced by method (7) was cut into a length of 40 mm and a width of 40 mm, and the retardation was measured at a wavelength of 550 nm using a retardation measuring device KOBRA-WPR manufactured by Oji Scientific Instruments Co., Ltd. The orientation birefringence Δn was calculated from the retardation R550 at a wavelength of 550 nm and the film thickness of the stretched film according to the following formula (iv). When the slow axis direction coincides with the stretching direction, Δn is shown as a positive value, and when the slow axis direction coincides with a direction perpendicular to the stretching direction, Δn is shown as a negative value. Δn = R550 [nm] / (film thickness [mm] × 10 6 ) (iv)

[0229] (9) Injection Molding of Plates Using a small injection molding machine (Shinko Celbic C, Mobile, Inc.), the cylinder temperature was adjusted to the temperatures listed in Tables 1 to 3 (Tg+105 to 155°C), and the mold temperature was adjusted to the range of 110 to 150°C, to mold a dumbbell-shaped resin plate with a total length of 75 mm, parallel portion length of 30 mm, parallel portion width of 5 mm, thickness of 2 mm, and gripping portion width of 10 mm.

[0230] (10) Birefringence of injection molded plates The injection-molded plate prepared by method (9) was used as a test piece, which was sandwiched between two polarizers in a crossed Nicol state at the angle at which the polarized color was most strongly expressed, and placed on an observation table. Under the condition that white light was irradiated from behind, the polarized color appearing on the test piece was visually observed, and the degree of birefringence was evaluated according to the following criteria. ◎: No polarization color is seen, or the polarization color is seen only in the 5 mm wide parallel section, and the color is one color. ○: Polarized color is seen only in the 5 mm wide parallel section, and there are two colors. △: Polarized color is seen only in the 5 mm wide parallel section, and there are three or more colors. ×: Polarized color is observed over the entire test piece.

[0231] [Synthesis Example 1: Bis[9-(2-phenoxycarbonylethyl)fluoren-9-yl] Synthesis of methane (hereinafter abbreviated as "2Q")] According to the method described in JP 2015-25111 A, 2Q represented by the following formula (11A) was synthesized.

[0232] [ka]

[0233] [Synthesis Example 2: Synthesis of 1,1-bis(4-hydroxyphenyl)dodecane (hereinafter abbreviated as "BP12A")] BP12A was synthesized by the method described in Example 1 of JP2019-085399A.

[0234] The abbreviations of the compounds used in the following Examples and Comparative Examples are as follows. BisAP: 1,1-bis(4-hydroxyphenyl)-1-phenylethane (Tokyo Chemical Industry Co., Ltd.) BisBP: Bis(4-hydroxyphenyl)diphenylmethane (Tokyo Chemical Industry Co., Ltd.) BPS: Bis(4-hydroxyphenyl)sulfone (Tokyo Chemical Industry Co., Ltd.) BP: 4,4'-biphenol (Tokyo Chemical Industry Co., Ltd.) BP12A: 1,1-bis(4-hydroxyphenyl)dodecane BPA: 2,2-bis(4-hydroxyphenyl)propane (Mitsubishi Chemical Corporation) BPEF: 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (Osaka Gas Chemicals Co., Ltd.) BNEF: 9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]fluorene (Osaka Gas Chemicals Co., Ltd.) DPC: Diphenyl carbonate (Mitsubishi Chemical Corporation) 2Q: Bis[9-(2-phenoxycarbonylethyl)fluoren-9-yl]methane ·PTSB: Catalyst deactivator, paratoluene butyl sulfonate (Tokyo Chemical Industry Co., Ltd.) Adeka STAB 2112: Antioxidant, Adeka STAB 2112 (manufactured by ADEKA) Irg1076: Antioxidant, Irganox 1076 (manufactured by BASF)

[0235] [Example 1] A glass reactor equipped with a reactor stirrer, a reactor heater, and a reactor pressure regulator was charged with 100.0 mol% BisAP, 60.0 mol% DPC, 40.0 mol% 2Q, and a 0.4 mass% aqueous solution of cesium carbonate as a catalyst, with the total amount of cesium carbonate being 2.0 × 10 -3 The raw material mixture was prepared by adding the components so as to obtain the desired mol %.

[0236] Next, the pressure in the glass reactor was reduced to about 50 Pa (0.38 Torr), and then the operation of returning the pressure to atmospheric pressure with nitrogen was repeated three times to replace the inside of the reactor with nitrogen. After nitrogen replacement, the temperature outside the reactor was set to 220°C, and the temperature inside the reactor was gradually raised to dissolve the mixture. Then, the stirrer was rotated at 100 rpm. Then, the pressure inside the reactor was reduced from 101.3 kPa (760 Torr) to 13.3 kPa (100 Torr) in absolute pressure over 40 minutes while distilling off phenol by-produced by the oligomerization reaction of dihydroxy compounds DPC and 2Q carried out inside the reactor.

[0237] Next, the pressure in the reactor was kept at 13.3 kPa, and the transesterification reaction was carried out for 80 minutes while further distilling off phenol. Thereafter, the temperature outside the reactor was raised to 250°C, and the pressure inside the reactor was reduced from 13.3 kPa (100 Torr) to 399 Pa (3 Torr) in absolute pressure over 40 minutes, and the distilled phenol was removed from the system. Furthermore, as the final temperature, the temperature outside the reactor was raised to 260°C, and the absolute pressure inside the reactor was reduced to 30 Pa (about 0.2 Torr), and a polycondensation reaction was carried out. The polycondensation reaction was terminated when the agitator of the reactor reached a predetermined predetermined agitation power.

[0238] Next, the pressure inside the reactor was restored to 101.3 kPa absolute pressure with nitrogen, and then the gauge pressure was increased to 0.2 MPa. The polyester carbonate resin was extracted in the form of strands from the bottom of the reactor. After the strands of resin were obtained, the polyester carbonate resin was pelletized using a rotary cutter. This polyester carbonate resin was evaluated according to the procedures described above, and the results are shown in Table 1.

[0239] [Examples 2 to 6] A polyester carbonate resin was obtained in the same manner as in Example 1, except that the raw materials and conditions for melt polymerization were as shown in Table 1. The polyester carbonate resin was evaluated according to the above-mentioned procedures. The results are shown in Table 1.

[0240] [Comparative Example 1] A polyester resin was obtained in the same manner as in Example 1, except that the raw materials and conditions for melt polymerization were as shown in Table 1. This polyester resin was subjected to various evaluations according to the procedures described above. The results are shown in Table 1.

[0241] [Comparative Example 2] A polycarbonate resin was obtained in the same manner as in Example 1, except that the raw materials and conditions for melt polymerization were as shown in Table 1. This polycarbonate resin was subjected to various evaluations according to the procedures described above. The results are shown in Table 1.

[0242] [Comparative Example 3] A polyester carbonate resin was obtained in the same manner as in Example 1, except that the raw materials and conditions for melt polymerization were as shown in Table 1, and the temperature outside the reactor was set to 230° C. in the step of dissolving the mixture in the reaction vessel. Each evaluation of this polyester carbonate resin was carried out according to the above-mentioned procedures. The results are shown in Table 1.

[0243] [Table 1]

[0244] [Examples 7 and 8] For the resin obtained in Example 1, a plate was produced by the method of (9) above under the conditions of a cylinder temperature and a mold temperature of 150° C. shown in Table 2, and birefringence was evaluated by the method of (10) above. The results are shown in Table 2 together with the results of Example 1.

[0245] [Table 2]

[0246] [Example 9] The same resin as in Example 1 and additive components PTSB, ADK STAB 2112, and Irg1076 were blended and mixed in the ratio (parts by mass) shown in Table 3 below, and then fed to a Japan Steel Works (TEX30HSS) equipped with one vent, and kneaded under the conditions of a screw rotation speed of 160 rpm, a discharge rate of 15 kg / h, and a barrel temperature of 260 ° C. The kneaded product was extruded into a strand-like molten resin, which was quenched in a water tank and pelletized using a pelletizer to obtain pellets of a polyester carbonate resin composition. For this polyester carbonate resin composition, a plate was prepared by the method (9) above under the conditions of a cylinder temperature and a mold temperature of 150 ° C. shown in Table 3, and birefringence was evaluated by the method (10) above. The results are shown in Table 3 together with the results of Example 1.

[0247] [Table 3]

[0248] [Discussion of evaluation results] The polyester carbonate resins of Examples 1 to 6 had small absolute values ​​of orientation birefringence, and the birefringence of the molded articles was small. Furthermore, because of their high Td, they can be melt-processed at a wider range of temperatures, which is advantageous for injection molding. Therefore, they are excellent materials for molded articles, particularly molded articles for optical members. In addition, the refractive index n D Since the Tg is high, it is also suitable for use in applications requiring thin-walled optical lenses, etc. Furthermore, since the Tg is high, it is also suitable for use in applications requiring heat resistance.

[0249] As shown in Examples 7 and 8, the polyester carbonate resin of the present invention can be injection molded under a wide range of temperature conditions and has excellent moldability. Furthermore, regardless of the injection molding conditions, the birefringence of the molded article is always low and the optical properties are excellent.

[0250] As shown in Example 9, the polyester carbonate resin of the present invention can be kneaded with additive components to form a polyester carbonate resin composition. The polyester carbonate resin composition of the present invention can be injection molded, and the molded article has low birefringence.

[0251] On the other hand, the resin of Comparative Example 1 has relatively high Td and Tg, but has a low composition ratio of structural units derived from an aromatic dihydroxy compound in which a hydroxy group represented by formula (2) is directly bonded to an aromatic group, and therefore the orientation birefringence of the stretched film is negatively large and the birefringence of the molded body is large.

[0252] The resins of Comparative Examples 2 and 3 have small birefringence in the molded products, but because they do not contain the structural unit (2), they have low Td and poor thermal stability, which may result in a narrow temperature range for melt processing or a narrow usable temperature range for the molded products, making them inferior as molding materials.

[0253] From the above, the resin of the present invention has a higher Td than the resin of the comparative example, and can be melt-processed and molded at a wide range of temperatures, making it an excellent molding material. In addition, since it has a high refractive index and the birefringence of the molded product is small, it is excellent as a molding material for optical components. Furthermore, it can be designed to have a high Tg, making it excellent as a material for optical components that require heat resistance. [Industrial Applicability]

[0254] The resin of the present invention has high thermal stability, a small absolute value of orientation birefringence, low birefringence of a molded article, and a high refractive index and high heat resistance. Therefore, the resin of the present invention and a resin composition containing the same can be easily processed into optical components by a method such as injection molding. These optical members are excellent in that they have a high refractive index and low birefringence while maintaining high thermal stability and high heat resistance.

[0255] Examples of such optical members include optical lenses, optical films, optical sheets, etc. Examples of optical lenses include vehicle-mounted lenses, eyeglass lenses, pickup lenses, camera lenses, microarray lenses, projector lenses, Fresnel lenses, etc. The resin of the present invention has high thermal stability and high heat resistance, and by appropriately selecting an aromatic dihydroxy compound, it has particularly high heat resistance, and therefore can be suitably used as a material for optical components that are expected to be used in high-temperature environments, such as vehicle-mounted lenses.

Claims

1. A polyester carbonate resin containing a structural unit represented by the following formula (1) and a structural unit represented by the following formula (2): A resin containing 40% by weight or more of a structural unit represented by the following formula (2), when the total weight of the resin is taken as 100% by weight. [Formula 1] (In formula (1), R １１ R 1 to R 12 are each independently an alkylene group having 2 to 3 carbon atoms; １３ is a direct bond or an alkylene group having 1 to 4 carbon atoms which may have a substituent, R １４ ~R １９ are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 10 carbon atoms which may have a substituent, an acyl group having 1 to 10 carbon atoms which may have a substituent, an amino group which may have a substituent, an alkenyl group having 2 to 10 carbon atoms which may have a substituent, an alkynyl group having 2 to 10 carbon atoms which may have a substituent, an oxygen atom which has a substituent, a sulfur atom which has a substituent, a silicon atom which has a substituent, a halogen atom, a nitro group, or a cyano group, provided that R １４ ~R １９ At least two adjacent groups among these may be bonded to each other to form a ring. [chemical 2] (In formula (2), Ar １ represents an unsubstituted or substituted aromatic hydrocarbon group having 6 to 88 carbon atoms, or a divalent group having 6 to 88 carbon atoms in which an unsubstituted or substituted aromatic hydrocarbon ring is linked via a direct bond or any linking group, and each of the two oxygen atoms shown in formula (2) is represented by Ar １ It represents that the ring is directly bonded to the same or different aromatic hydrocarbon rings in the ring.

2. The resin according to claim 1, wherein the content of the structural unit represented by formula (1) is 5% by weight or more when the total weight of the resin is taken as 100% by weight.

3. 3. The resin according to claim 1, wherein the total content of the structural unit represented by formula (1) and the structural unit represented by formula (2) is 80% by weight or more when the total weight of the resin is 100% by weight.

4. The resin according to any one of claims 1 to 3, wherein the formula (2) is represented by the following formula (3): [C3] (In formula (3), ring Z １ , Z ２ R each independently represents an aromatic hydrocarbon ring. １ , R ２ are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, an oxygen atom having a substituent, a sulfur atom having a substituent, a silicon atom having a substituent, or a halogen atom. a and b each independently represent an integer of 0 or more. When a and b are 2 or more and R １ , R ２ If there are multiple R １ , R ２ may be the same or different. １ and / or R ２ At least two of the groups may be bonded to each other to form a ring. Y represents a single bond, a hydrocarbon group having 1 to 44 carbon atoms which may contain an aromatic group, O, S, S-S, SO, SO ２ or a CO group.

5. In the formula (3), Y is a single bond, a hydrocarbon group having 1 to 44 carbon atoms which may contain an aromatic group, S, S—S, SO, or SO ２ 5. The resin of claim 4,

6. In the formula (3), Y is a single bond, S, S—S, SO, SO ２ or a group represented by any one of the following formulae (Y1) to (Y3) (wherein the * mark in the following formulae (Y1) to (Y3) represents the ring Z in the formula (3)). １ , Z ２The resin according to claim 5, wherein [C4] (In formula (Y1), R ３ , R ４ are each independently a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms. [C5] (In formula (Y2), R ５ R is a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms. ６ represents an unsubstituted or substituted aromatic hydrocarbon group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, or a halogen atom. c represents an integer of 0 to 5. When c is 2 or more, R ６ If there are multiple R ６ may be the same or different. ６ At least two of the groups may be bonded to each other to form a ring. [C6] (In formula (Y3), R ７ , R ８ are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted or substituted acyl group having 1 to 10 carbon atoms, or a halogen atom. d and e are each independently an integer of 0 to 5. When d and e are 2 or more, R ７ , R ８ If there are multiple R ７ , R ８ may be the same or different. ７ and / or R ８ At least two of the groups may be bonded to each other to form a ring.

7. The resin according to claim 6, wherein the formula (3) is at least one selected from the group consisting of the following formulas (3-1) to (3-5): [C7] (In formulas (3-1) to (3-5), R １ , R ２ , a, and b are defined as in formula (3). ６ , c are defined as in formula (Y2). ７ , R ８ , d, and e are defined as the same as in formula (Y3).

8. The resin according to claim 7, wherein the formula (3) is at least one selected from the group consisting of the following formulas (3-6) to (3-10): [C8]

9. The resin according to any one of claims 1 to 8, having a refractive index of 1.59 or more at a wavelength of 589 nm.

10. The resin according to any one of claims 1 to 9, having an Abbe number vD of 35.0 or less.

11. The resin according to any one of claims 1 to 10, wherein a stretched film made from the resin has an in-plane orientation birefringence of -0.0010 or more and 0.0020 or less at a wavelength of 550 nm.

12. The resin according to any one of claims 1 to 11, having a 1% thermal weight loss temperature (Td) under nitrogen of 355°C or higher.

13. The resin according to any one of claims 1 to 12, having a glass transition temperature (Tg) of 110°C or more and 250°C or less.

14. A resin composition comprising the resin according to any one of claims 1 to 13 and at least one additive selected from the group consisting of a heat stabilizer, an antioxidant, an ultraviolet absorber, a brightness enhancer, a dye, a pigment, a release agent, a flow modifier, and an impact resistance improver.

15. A resin composition comprising the resin according to any one of claims 1 to 13 or the resin composition according to claim 14, further comprising another resin.

16. A molded article obtained by molding the resin according to any one of claims 1 to 13 or the resin composition according to claim 14 or 15.

17. The molded article according to claim 16, which is an optical component.

18. The molded article according to claim 17, wherein the optical member is at least one optical lens selected from the group consisting of an in-vehicle lens, a spectacle lens, a pickup lens, a camera lens, a microarray lens, a projector lens, and a Fresnel lens.

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