TW202244031A - Thermoplastic resin and optical member - Google Patents

Abstract

The problem to be solved by the present invention is to provide a thermoplastic resin which can have a balance among high refractive index, high heat resistance, and low birefringence and an optical member including the thermoplastic resin. The thermoplastic resin includes repeating units represented by formula (1). (In formula (1), the rings Z (which are the same or different) each represent an aromatic hydrocarbon ring, R1 and R2 each independently represent a hydrogen atom, a halogen atom, or a C1-C20 substituent optionally including an aromatic group, Ar1 and Ar2 each independently represent a polycyclic aromatic hydrocarbon group composed of three or more benzene rings fused together, L1 and L2 each independently represent a divalent linking group, j and k are each independently an integer of 1 or larger, m and n are each independently 0 or 1, and W represents at least one group selected from the group consisting of groups represented by formula (2) and formula (3).) (In formula (3), X represents a divalent linking group.).

Description

Thermoplastic resin and optical member

The present invention relates to a thermoplastic resin capable of balancing high refractive index, high heat resistance, and low birefringence, and a compound having a fennel skeleton (hereinafter also referred to as a fennel compound) that can be used as a raw material of the thermoplastic resin.

The camera module is used in a camera, a video camera or a mobile phone with a camera, a TV phone or a walkie-talkie with a camera, etc. In recent years, the miniaturization of the optical system used in the camera module has been particularly demanded. With the miniaturization of the optical system, chromatic aberration of the optical system becomes a big problem. Therefore, it is known that by combining a highly dispersed optical lens material obtained by increasing the refractive index of an optical lens and reducing the Abbe number, and a low-dispersion optical lens material obtained by reducing the refractive index and increasing the Abbe number, And can compensate (compensate) chromatic aberration.

Conventionally, glass systems used as optical system materials can realize various required optical properties and have excellent environmental resistance, but they have problems such as poor processability. On the other hand, resins that are cheaper than glass materials and have excellent workability can be used for optical parts. In particular, resins having a fennel skeleton or a binaphthyl skeleton are used for reasons such as high refractive index. For example, Patent Document 1 or Patent Document 2 describes the use of a high-refractive-index resin having a refractive index of 1.64 of 9,9-bis(4-(2-hydroxyethoxy)phenyl) fluorine. However, since the refractive index is insufficient, a higher refractive index is required. Also, Patent Document 3 describes a thermoplastic resin having 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)terpene.

Furthermore, in order to achieve a higher refractive index, Patent Document 4 or Patent Document 5 describes a thermoplastic resin in which an aromatic ring is introduced into the fennel skeleton. Although it is effective for a higher refractive index and higher heat resistance, it is known that as The expansion of the conjugation centered on the fennel part increases the refractive index and the birefringence also increases, so there are still problems as an optical component. [Prior Art Literature] [Patent Document]

[Patent Document 1] International Publication No. 2007/142149 [Patent Document 2] Japanese Patent Application Laid-Open No. 7-198901 [Patent Document 3] Japanese Patent Laid-Open No. 2015-86265 [Patent Document 4] International Publication No. 2019/044214 [Patent Document 5] International Publication No. 2020/226126

[Problem to be Solved by the Invention]

The object of the present invention is to provide a thermoplastic resin excellent in balance of high refractive index, high heat resistance, and low birefringence, an optical member including the same, and a novel fennel that can be used as a raw material of such a thermoplastic resin. compound. [Means to solve the problem]

As a result of intensive research to achieve this object, the present inventors have found that the above-mentioned problems can be solved by using a specific compound having a structure obtained by introducing three or more benzene rings into the fennel skeleton and undergoing ring condensation to produce a thermoplastic resin. this invention. That is, the present invention is as follows.

(式中，環Z係(相同或相異地)表示芳香族烴環，R ¹及R ²分別獨立表示氫原子、鹵素原子、可包含芳香族基的碳原子數1~20的取代基，Ar ¹及Ar ²分別獨立為3個以上的苯環經縮環而成的多環芳香族烴基，L ¹及L ²分別獨立表示2價的連結基，j及k分別獨立表示1以上的整數，m及n分別獨立表示0或1，W係選自以下述式(2)及下述式(3)表示之群組之至少一者)。 ≪Aspect 1≫ A thermoplastic resin comprising a repeating unit represented by the following formula (1),

(In the formula, the ring Z system (same or different) represents an aromatic hydrocarbon ring, R1 and R2 independently represent ^{a hydrogen} atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, and Ar ¹ and Ar ² are each independently a polycyclic aromatic hydrocarbon group formed by condensing 3 or more benzene rings, L ¹ and L ² each independently represent a divalent linking group, j and k each independently represent an integer of 1 or more, m and n each independently represent 0 or 1, and W is at least one selected from the group represented by the following formula (2) and the following formula (3).

(式中，X表示2價的連結基)。

(In the formula, X represents a divalent linking group).

≪Aspect 2≫ The thermoplastic resin according to Aspect 1, wherein the aforementioned formula (1) is at least one selected from the group consisting of units represented by the following formulas (1a) to (1d).

(In the formula, the ring Z system (same or different) represents an aromatic hydrocarbon ring, R1 and R2 independently represent ^{a hydrogen} atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, and Ar ¹ and Ar ² are respectively independently polycyclic aromatic hydrocarbons formed by condensing 3 or more benzene rings, L ¹ and L ² independently represent a divalent linking group, j and k independently represent an integer of 1 or more, m and n each independently represent 0 or 1, and W is at least one selected from the group represented by the aforementioned formula (2) and the aforementioned formula (3).

≪Aspect 3≫ The thermoplastic resin according to Aspect 2, wherein the aforementioned formula (1) is the aforementioned formula (1b).

≪Aspect 4≫ The thermoplastic resin according to any one of Aspects 1 to 3, wherein Ar ¹ and Ar ² in the aforementioned formula (1) are phenanthene-type polycyclic aromatic hydrocarbons.

≪Aspect 5≫ The thermoplastic resin according to any one of Aspects 1 to 4, wherein, in the above-mentioned formula (1), Ar ¹ and Ar ² are formed by condensing 3 or 4 benzene rings polycyclic aromatic hydrocarbons.

≪Aspect 6≫ The thermoplastic resin according to any one of Aspects 1 to 5, wherein, in the aforementioned formula (1), Ar ¹ and Ar ² are phenanthrene.

≪Aspect 7≫ The thermoplastic resin according to any one of Aspects 1 to 6, wherein the repeating unit represented by the aforementioned formula (1) is represented by the following formula (4).

(In the formula, the ring Z system (same or different) represents an aromatic hydrocarbon ring, R1 and R2 independently represent ^{a hydrogen} atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, and L ¹ and L2 each independently represent a divalent linking group, j and ^k each independently represent an integer greater than 1, m and n each independently represent 0 or 1, W is selected from the aforementioned formula (2) and the aforementioned formula (3) at least one of the groups indicated).

≪Aspect 8≫ The thermoplastic resin according to any one of Aspects 1 to 7, wherein the repeating unit represented by the aforementioned formula (1) is represented by the following formula (5).

(wherein, L ¹ and L ² independently represent a divalent linking group, m and n independently represent 0 or 1, W is at least one of the groups represented by the aforementioned formula (2) and the aforementioned formula (3) one).

(式中，R ³及R ⁴分別獨立為氫原子、可包含芳香族基的碳原子數1~20的取代基或鹵素原子)。 ≪Aspect 9≫ The thermoplastic resin according to any one of Aspects 1 to 8, wherein X in the above-mentioned formula (3) is selected from the group consisting of phenylene, naphthalenediyl, and the following formula (6) At least one of the indicated bases is used as the repeating unit.

(In the ^formula , ^R3 and R4 are each independently a hydrogen atom, a substituent having 1 to 20 carbon atoms that may contain an aromatic group, or a halogen atom).

≪Aspect 10≫ The thermoplastic resin according to any one of Aspects 1 to 9, wherein, in addition to the repeating unit represented by formula (1), it further contains a group consisting of units represented by the following formulas (7) to (10). At least one of the groups is used as a repeating unit.

(式中，R ⁵及R ⁶分別獨立為氫原子、可包含芳香族基的碳原子數1~20的取代基或鹵素原子)。

(In the formula, R ⁵ and R ⁶ are each independently a hydrogen atom, a substituent having 1 to 20 carbon atoms that may contain an aromatic group, or a halogen atom).

(式中，R ⁷及R ⁸分別獨立為氫原子、可包含芳香族基的碳原子數1~20的取代基或鹵素原子)。

(In the formula, R ⁷ and R ⁸ are each independently a hydrogen atom, a substituent having 1 to 20 carbon atoms that may include an aromatic group, or a halogen atom).

(式中，R ⁹及R ¹⁰分別獨立為氫原子、可包含香族基的碳原子數1~20的取代基或鹵素原子)。

(In the formula, R ⁹ and R ¹⁰ are each independently a hydrogen atom, a substituent having 1 to 20 carbon atoms that may include an aromatic group, or a halogen atom).

(式中，R ¹¹及R ¹²分別獨立為氫原子、可包含芳香族基的碳原子數1~20的取代基或鹵素原子，U係單鍵或2價的連結基)。

(In the formula, R ¹¹ and R ¹² are each independently a hydrogen atom, a substituent with 1 to 20 carbon atoms that may include an aromatic group, or a halogen atom, and U is a single bond or a divalent linking group).

≪Aspect 11≫ The thermoplastic resin according to any one of aspects 1 to 10, wherein the refractive index is 1.650 to 1.800.

≪Aspect 12≫ The thermoplastic resin according to any one of aspects 1 to 11, wherein the specific viscosity is 0.12 to 0.40.

≪Aspect 13≫ The thermoplastic resin according to any one of aspects 1 to 12, wherein the glass transition temperature is 130 to 190°C.

≪Aspect 14≫ The thermoplastic resin according to any one of Aspects 1 to 13, wherein the orientation double refraction is 5.0×10 ^-3 or less.

≪Aspect 15≫ An optical component made of the thermoplastic resin according to any one of aspects 1 to 14.

≪Aspect 16≫ The optical member according to Aspect 15 is an optical lens.

≪Aspect 17≫ A compound having a fennel skeleton represented by the following formula (a).

(In the formula, ring Z represents an aromatic hydrocarbon ring identically or differently, R ¹ and R ² independently represent a hydrogen atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, Ar ¹ and R 2 Ar ² is a polycyclic aromatic hydrocarbon group formed by condensing 3 or more benzene rings, L ¹ and L ² independently represent a divalent linking group, j and k independently represent an integer of 1 or more, m and n respectively independently 0 or 1).

≪Aspect 18≫ The compound having a fennel skeleton according to Aspect 17, wherein the aforementioned formula (a) is at least one selected from the group consisting of compounds represented by the following formulas (a-I) to (a-IV).

(In the formula, ring Z represents an aromatic hydrocarbon ring identically or differently, R ¹ and R ² independently represent a hydrogen atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, Ar ¹ and R 2 Ar ² is a polycyclic aromatic hydrocarbon formed by condensing 3 or more benzene rings, L ¹ and L ² independently represent a divalent linking group, j and k independently represent an integer of 1 or more, m and n respectively independently 0 or 1).

≪Aspect 19≫ The compound having a fennel skeleton according to Aspect 18, wherein the aforementioned formula (a) is the aforementioned formula (a-II).

≪Aspect 20≫ The compound having a fennel skeleton according to any one of Aspects 17 to 19, wherein Ar ¹ and Ar ² in the aforementioned formula (a) are phenanthrene-type polycyclic aromatic hydrocarbons.

≪Aspect 21≫ The compound having a fennel skeleton according to any one of Aspects 17 to 20, wherein, in the above-mentioned formula (a), Ar ¹ and Ar ² are 3 or 4 benzene rings obtained by condensing polycyclic aromatic hydrocarbons.

≪Aspect 22≫ The compound having a fennel skeleton according to any one of Aspects 17 to 21, wherein, in the aforementioned formula (a), Ar ¹ and Ar ² are phenanthrene.

(式中，環Z係相同或相異地表示芳香族烴環，R ¹及R ²分別獨立表示氫原子、鹵素原子、可包含芳香族基的碳原子數1~20的取代基，L ¹及L ²分別獨立表示2價的連結基，j及k分別獨立表示1以上的整數，m及n分別獨立為0或1)。 ≪Aspect 23≫ The compound having a fennel skeleton according to any one of Aspects 17 to 22, wherein the aforementioned formula (a) is represented by the following formula (b).

(In the formula, ring Z represents an aromatic hydrocarbon ring identically or differently, R1 and R2 independently represent ^{a hydrogen} atom, a halogen atom, a substituent with ¹ to 20 carbon atoms that may contain an aromatic group, L1 and L ² each independently represent a divalent linking group, j and k each independently represent an integer of 1 or more, m and n each independently represent 0 or 1).

(式中，L ¹及L ²分別獨立表示2價的連結基，m及n分別獨立為0或1)。 ≪Aspect 24≫ The compound having a fennel skeleton according to any one of Aspects 17 to 23, wherein the aforementioned formula (a) is represented by the following formula (c).

(In the formula, L ¹ and L ² each independently represent a divalent linking group, and m and n are each independently 0 or 1).

≪Aspect 25≫ The compound having a fennel skeleton according to any one of aspects 17 to 24, wherein the refractive index is 1.70 or more. [Effect of the invention]

The thermoplastic resin produced by using the compound having a fennel skeleton of the present invention has an excellent balance of high refractive index, high heat resistance, and low birefringence, so it can be used in optical lenses, discs, optical discs, transparent conductive substrates, Optical components such as optical cards, sheets, films, optical fibers, optical films, optical filters, hard coatings, etc., especially for mobile phones, smart phones, tablet terminals, personal computers, digital cameras, video cameras, car cameras , or the optical lens of any one of the surveillance camera is very useful, therefore, the industrial effect it exerts is particularly special.

[Best Mode for Carrying Out the Invention]

Furthermore, this invention is demonstrated in detail. <Thermoplastic resin> The thermoplastic resin of this invention contains the thermoplastic resin of the repeating unit represented by following formula (1).

(In the formula, the ring Z system (same or different) represents an aromatic hydrocarbon ring, R1 and R2 independently represent ^{a hydrogen} atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, and Ar ¹ and Ar ² are each independently a polycyclic aromatic hydrocarbon group formed by condensing 3 or more benzene rings, L ¹ and L ² each independently represent a divalent linking group, j and k each independently represent an integer of 1 or more, m and n each independently represent 0 or 1, and W is at least one selected from the group represented by the following formula (2) and the following formula (3).

(式中，X表示2價的連結基)。

(In the formula, X represents a divalent linking group).

In the aforementioned formula (1), Ar ¹ and Ar ² are independently polycyclic aromatic hydrocarbon groups formed by condensing 3 or more benzene rings, and are formed by condensing 3 or 4 benzene rings. Polycyclic aromatic hydrocarbons are preferred, and polycyclic aromatic hydrocarbons obtained by condensing three benzene rings are further preferred.

In the aforementioned formula (1), the polycyclic aromatic hydrocarbons of Ar ¹ and Ar ² are preferably formed with a benzene ring condensed into an acene or phenanthrene type, and phenanthrene through condensed rings. The structure of the type is better.

In the aforementioned formula (1), Ar ¹ and Ar ² are preferably anthracene, phenanthrene, pyrene, and chrysene, and are more preferably phenanthrene and anthracene. From the point of view of stability caused by orbital differences, Philippine is better.

The respective bonding positions of Ar ¹ and Ar ² are 1-position and 8-position (following formula (1a)), 2-position and 7-position (following formula (1b)), 3-position and 6-position ( The following formula (1c)), or 4-position and 5-position (following formula (1d)) are preferred, and 2-position and 7-position, 3-position and 6-position, or 4-position and 5-position are preferred, 2 and 7 are better.

(In the formula, ring Z, R ¹ , R ² , Ar ¹ , Ar ² , L ¹ , L ² , j, k, m, n, and W are the same as those of the aforementioned formula (1)).

In the above-mentioned formula (1), as the aromatic hydrocarbon ring represented by the ring Z, in addition to the benzene ring, a condensed polycyclic aromatic hydrocarbon ring having at least a benzene ring skeleton, such as a condensed bicyclic hydrocarbon ring Condensed bi- to tetracyclic hydrocarbon rings such as rings, condensed tricyclic hydrocarbon rings, etc. are preferred.

As the condensed bicyclic hydrocarbon ring system, a C _8-20 indene ring, a naphthalene ring, etc. are preferred, and a C _10-16 condensed bicyclic hydrocarbon ring is further preferred. Also, anthracycline, phenanthrene ring and the like are preferable as the condensed tricyclic hydrocarbon ring system.

Among the rings Z, a benzene ring and a naphthalene ring are preferable, and a naphthalene ring is more preferable from the viewpoint of realizing a higher refractive index.

In the aforementioned formula (1), as specific examples of the aromatic hydrocarbon ring represented by ring Z, 1,4-phenylene, 1,4-naphthalenediyl or 2,6-naphthalenediyl is preferred, 2,6-naphthalenediyl is preferred.

In the aforementioned formula ( ¹ ), R1 and R2 independently represent a ^hydrogen atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, and a hydrogen atom, a methyl group, a phenyl group, a naphthyl group More preferably, a hydrogen atom, a methyl group, and a phenyl group are more preferable, a hydrogen atom and a methyl group are more preferable, and a hydrogen atom is particularly preferable.

In the aforementioned formula (1), L ¹ and L ² independently represent a divalent linking group, preferably an alkylene group with 1 to 12 carbons, and more preferably an alkylene group with 1 to 4 carbons , more preferably ethylenyl. By adjusting the lengths of the linking groups L ¹ and L ² , the glass transition temperature (Tg) of the resin can be adjusted.

In the aforementioned formula (1), W is at least one selected from the group represented by the aforementioned formula (2) and the aforementioned formula (3). When W is the aforementioned formula (2), the aforementioned formula (1) is a carbonate unit, and when W is the aforementioned formula (3), the aforementioned formula (1) is an ester unit.

The aforementioned formula (1) can be obtained from a carbonate precursor such as a dihydroxy compound and carbonate, or a dihydroxy compound and a dicarboxylic acid or an ester-forming derivative thereof.

In the aforementioned formula (1), m and n are independently 0 or 1, preferably 1.

In the aforementioned formula (1), j and k are each independently an integer of 1 or more, preferably an integer of 1 to 4, and more preferably 1.

The repeating unit represented by the aforementioned formula (1) is preferably a repeating unit represented by the following formula (4).

(式中，環Z、R ¹及R ²、L ¹及L ²、j及k、m及n、W係與前述式(1)相同)。

(In the formula, ring Z, R ¹ and R ² , L ¹ and L ² , j and k, m and n, and W are the same as those in the aforementioned formula (1)).

(式中，L ¹及L ²、j及k、m及n、W係與前述式(1)相同)。 Furthermore, the repeating unit represented by the aforementioned formula (1) is also preferably a repeating unit represented by the following formula (5).

(In the formula, L ¹ and L ² , j and k, m and n, and W are the same as the aforementioned formula (1)).

In the aforementioned formula (3), X represents a divalent linking group, preferably a substituent with 1 to 30 carbon atoms that may contain an aromatic group, such as a phenylene group, a naphthalenediyl group, and the following formula ( 6) The group represented is more preferable.

(式中，R ³及R ⁴分別獨立為氫原子、可包含碳原子數1~20的芳香族基的烴基或鹵素原子)。

(In the ^formula , ^R3 and R4 are each independently a hydrogen atom, a hydrocarbon group that may contain an aromatic group with 1 to 20 carbon atoms, or a halogen atom).

In the aforementioned formula ( ⁶ ), ^R3 and R4 independently represent a hydrogen atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, and a hydrogen atom, a methyl group, a phenyl group, a naphthyl group More preferably, a hydrogen atom, a methyl group, and a phenyl group are more preferable, a hydrogen atom and a methyl group are more preferable, and a hydrogen atom is particularly preferable.

The reason why the high refractive index, high heat resistance, and low birefringence, which are the effects of the present invention, can be highly balanced is considered as follows.

Patent Document 4 discloses that 9,9-bis(4-(2-hydroxyethoxy)phenyl)-2,7-bis(2-naphthyl)tilbene (hereinafter also referred to as " BPDN2") and the like are thermoplastic resins obtained by using a compound in which an aromatic group having 6 to 10 carbon atoms is introduced into the branched chain of the fennel skeleton.

This patent document 4 discloses that both the refractive index and the birefringence can be improved by expanding the conjugation between the introduced aromatic group and the oxale moiety. However, the present inventors have newly discovered: "When introducing three or more polycyclic aromatic hydrocarbon-based polymers formed by condensing benzene rings into the branched chain of the polymer with the fennel skeleton, the refractive index can be increased without birefringence. will rise". With the above features, it is possible to solve the problem of the prior art: the trade off between "the effect of increasing the refractive index" and "the increase of birefringence".

From the relationship between the molecular structure and the refractive index known as the Lorentz-Lorenz formula, it can be known that the refractive index of a substance can be increased by increasing the electron density of the molecule and reducing the molecular volume. Based on this theory, resins having a fennel skeleton, which are conventional technologies, have a high refractive index by introducing a large number of aromatic groups into the molecule. At this time, if the aromatic group is introduced in such a way that the conjugated state is expanded, the electron density further increases due to the formation of the conjugated state, and as a result, both the refractive index and the birefringence are increased. That is to say, it is considered that in the control of birefringence, it is necessary to increase the electron density of the molecule in a way that does not expand the conjugated state. In the present invention, by setting the introduced aromatic group as a polycyclic aromatic hydrocarbon group formed by condensing three or more benzene rings, stereo hindrance can be generated, and the conjugated state will not expand, so it is considered possible The high refractive index and birefringence are highly balanced.

In addition, since a large amount of aromatic groups are introduced into the thermoplastic resin of the present invention, heat resistance can be improved, and formability can also be balanced.

The thermoplastic resin represented by formula (1) in the present invention may contain 5 mol% or more, 10 mol% or more, 15 mol% or more, 20 mol% or more, 25 mol% or more, 30 mol% or more of the repeating unit represented by the aforementioned formula (1) , may contain 100 mol% or less, 90 mol% or less, 80 mol% or less, 70 mol% or less, 60 mol% or less, or 50 mol% or less of the repeating unit represented by the aforementioned formula (1). The resin system of the present invention may contain preferably 10 mol% to 100 mol%, preferably 20 mol% to 80 mol%, more preferably 20 mol% to 70 mol%, particularly preferably 20 mol% to 60 mol%, most preferably The repeating unit represented by the aforementioned formula (1) is 20 mol% or more and 50 mol% or less. When the repeating unit represented by the aforementioned formula (1) is within the aforementioned range, it is preferable because the balance between the refractive index, birefringence, heat resistance, and formability is excellent.

The thermoplastic resin of the present invention may further contain at least one member selected from the group consisting of units represented by the following formulas (7) to (10) as a repeating unit.

(式中，R ⁵及R ⁶係與前述式(6)的R ³及R ⁴為相同)。

(In the formula, R ⁵ and R ⁶ are the same as R ³ and R ⁴ of the aforementioned formula (6)).

(式中，R ⁷及R ⁸係與前述式(6)的R ³及R ⁴為相同)。

(In the formula, R ⁷ and R ⁸ are the same as R ³ and R ⁴ of the aforementioned formula (6).

(式中，R ⁹及R ¹⁰係與前述式(6)的R ³及R ⁴為相同)。

(In the formula, R ⁹ and R ¹⁰ are the same as R ³ and R ⁴ of the aforementioned formula (6).

(式中，R ¹¹及R ¹²係與前述式(5)的R ³及R ⁴為相同，U表示單鍵或2價的連結基)。

(In the formula, R ¹¹ and R ¹² are the same as R ³ and R ⁴ in the aforementioned formula (5), and U represents a single bond or a divalent linking group).

The mol ratio of the repeating unit represented by the foregoing formula (1) to the repeating unit of the group formed by the units represented by the foregoing formula (7) to (10) is preferably 95:5 to 5:95, and more The best is 80:20~20:80, more preferably 70:30~30:70. When the molar ratio of the repeating unit represented by the aforementioned formula (1) to at least one repeating unit selected from the group consisting of the units represented by the aforementioned formulas (7) to (10) is within the aforementioned range, except In addition to a high refractive index, birefringence and formability are also excellent in balance, so it is preferable.

＜Physical properties of thermoplastic resins＞ The specific viscosity of the thermoplastic resin of the present invention is preferably 0.12-0.40, more preferably 0.14-0.35, and more preferably 0.16-0.30. When the specific viscosity is within the above range, it is preferable because the balance between formability and mechanical strength is excellent.

The method of measuring the specific viscosity is to measure the specific viscosity (η _SP ) of a solution of 0.7 g of thermoplastic resin dissolved in 100 ml of methylene chloride at 20° C. with an Oswald viscometer, and calculate it by the following formula. Specific viscosity (η _SP )=(tt ₀ )/t ₀ [t ₀ is the falling seconds of dichloromethane, t is the falling seconds of the sample solution]

When measured at a temperature of 20°C and a wavelength of 587.56 nm, the thermoplastic resin of the present invention has a refractive index of 1.650 or more, may be 1.660 or more, 1.670 or more, 1.680 or more, 1.690 or more, or 1.700 or more, and may be 1.800 or less , may be 1.790 or less, 1.780 or less, 1.770 or less, 1.760 or less, or 1.750 or less. The refractive index of the thermoplastic resin of the present invention is preferably 1.650-1.800, more preferably 1.670-1.800, more preferably 1.680-1.800, particularly preferably 1.690-1.800, and most preferably 1.700-1.800 . When the refractive index is above the lower limit, the spherical aberration of the optical lens can be reduced, and the focal length of the optical lens can be shortened.

The thermoplastic resin of the present invention has a high refractive index, but preferably has a low Abbe number.

The Abbe number of the thermoplastic resin of the present invention may be 5 or more, 7 or more, 9 or more, 10 or more, 12 or more, or 14 or more, and may be 24 or less, 23 or less, 22 or less, 21 or less, 20 or less, 19 or less. under or under 18. Abbe's number (νd) is preferably 5-22, more preferably 7-22, and more preferably 10-21.

Here, the Abbe number is calculated from the refractive index of temperature: 20°C, wavelength: 486.13nm, 587.56nm, and 656.27nm using the following formula: νd=(nd-1)/(nF-nC) nd: Represents the refractive index at a wavelength of 587.56nm, nF: Represents the refractive index at a wavelength of 486.13nm, nC: Represents the refractive index at a wavelength of 656.27 nm.

The thermoplastic resin of the present invention may have a glass transition temperature (Tg) of 130°C or higher, 135°C or higher, 140°C or higher, 145°C or higher, or 150°C or higher, or 190°C or lower, 185°C or lower, or 180°C Below, below 175°C, below 170°C. The temperature is preferably 130~190°C, more preferably 140~185°C, and more preferably 140~180°C. When the glass transition temperature is within the above range, it is preferable because the balance between heat resistance and formability is excellent.

In the thermoplastic resin of the present invention, the absolute value of alignment birefringence (|Δn|) is preferably 5.0×10 ^-3 or less, more preferably 4.5×10 ^-3 or less, and 4.0×10 ^-3 or less. Even better, below 3.5×10 ^-3 is particularly good, and below 3.0×10 ^-3 is the best. When |Δn| is within the above range, it is preferable because the optical distortion of the optical lens becomes small.

A film with a thickness of 100 μm obtained from the thermoplastic resin of the present invention is stretched twice at a temperature of Tg+10° C., and the phase difference at a wavelength of 589 nm is measured, and Δn is obtained by the following formula. |Δn|=|Re/d| Δn: alignment birefringence Re: phase difference (nm) d: thickness (nm)

The thermoplastic resin of the present invention preferably has a water absorption rate of not more than 0.25% by mass, more preferably not more than 0.20% by mass, after immersion in water at 23° C. for 24 hours. When the water absorption is within the above-mentioned range, it is preferable because the change in optical characteristics due to water absorption is small.

＜Materials for thermoplastic resins＞ (diol component of formula (1)) The diol component used as the raw material of the formula (1) is mainly a compound having a fennel skeleton represented by the formula (a) of the present invention, and may be used alone or in combination of two or more.

(式中，環Z、R ¹及R ²、Ar ¹及Ar ²、L ¹及L ²、j及k、m及n係與前述式(1)相同)。

(In the formula, ring Z, R ¹ and R ² , Ar ¹ and Ar ² , L ¹ and L ² , j and k, m and n are the same as the aforementioned formula (1)).

The compound represented by the aforementioned formula (a) is preferably a compound having a fennel skeleton represented by the following formula (b).

(式中，環Z、R ¹及R ²、L ¹及L ²、j及k、m及n係與前述式(a)相同)。

(In the formula, the ring Z, R ¹ and R ² , L ¹ and L ² , j and k, m and n are the same as the aforementioned formula (a)).

Furthermore, the compound represented by the aforementioned formula (a) is also preferably a compound having a fennel skeleton represented by the following formula (c).

(式中，L ¹及L ²、m及n係與前述式(a)中者相同)。

(In the formula, L ¹ and L ² , m and n are the same as those in the aforementioned formula (a)).

Representative specific examples of the dihydroxy compound represented by the above-mentioned formula (a) are shown below, but the raw materials used for the above-mentioned formula (1) of the present invention are not limited thereto.

When ring Z is benzene, 9,9-bis(4-hydroxyphenyl)-1,8-bis(9-anthracenyl) represented by the following formulas (a-1) and (a-2) Perylene, 9,9-bis(4-hydroxyphenyl)-1,8-bis(9-phenanthrene) fluorine, 9,9-bis(4-hydroxyphenyl)-1,8-bis(1-pyrene Base) fennel, 9,9-bis(4-hydroxyphenyl)-1,8-bis(1-tolyl) fennel, 9,9-bis(4-hydroxyphenyl)-2,7-bis(9 -Anthracenyl) stilbene, 9,9-bis(4-hydroxyphenyl)-2,7-bis(9-phenanthrenyl) fluorine, 9,9-bis(4-hydroxyphenyl)-2,7- (1-pyrenyl) fluorene, 9,9-bis(4-hydroxyphenyl)-2,7-bis(1-tolyl) fluorine, 9,9-bis(4-hydroxyphenyl)-3,6 -Bis(9-anthracenyl) fluorine, 9,9-bis(4-hydroxyphenyl)-3,6-bis(9-phenanthrenyl) fluorine, 9,9-bis(4-hydroxyphenyl)-3 ,6-bis(1-pyrenyl) fluorene, 9,9-bis(4-hydroxyphenyl)-3,6-bis(1-tolyl) fluorine, 9,9-bis(4-hydroxyphenyl) -4,5-bis(9-anthracenyl) fluorene, 9,9-bis(4-hydroxyphenyl)-4,5-bis(9-phenanthrenyl) fluorine, 9,9-bis(4-hydroxyphenyl) base)-4,5-bis(1-pyrenyl) fluorene, 9,9-bis(4-hydroxyphenyl)-4,5-bis(1-tolyl) fluorine, 9,9-bis(4- (2-Hydroxyethoxy)phenyl)-1,8-bis(9-anthracenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)phenyl)-1,8-bis (9-phenanthrenyl) fluorene, 9,9-bis(4-(2-hydroxyethoxy)phenyl)-1,8-bis(1-pyrenyl) fluorine, 9,9-bis(4-( 2-Hydroxyethoxy) phenyl) -1,8-bis (1-tolyl) fluorene, 9,9-bis (4- (2-hydroxyethoxy) phenyl) -2,7-bis ( 9-Anthracenyl) fluorine, 9,9-bis(4-(2-hydroxyethoxy)phenyl)-2,7-bis(9-phenanthrenyl) fluorine, 9,9-bis(4-(2 -Hydroxyethoxy)phenyl)-2,7-bis(1-pyrenyl) fluorene, 9,9-bis(4-(2-hydroxyethoxy)phenyl)-2,7-bis(1 -tolyl) fluorine, 9,9-bis(4-(2-hydroxyethoxy)phenyl)-3,6-bis(9-anthracenyl) fluorine, 9,9-bis(4-(2- Hydroxyethoxy) phenyl) -3,6-bis(9-phenanthrenyl) fluorene, 9,9-bis(4-(2-hydroxyethoxy)phenyl)-3,6-bis(1- Pyrenyl) fluorine, 9,9-bis(4-(2-hydroxyethoxy)phenyl)-3,6-bis(1-tolyl) fluorine, 9,9-bis(4-(2-hydroxy Ethoxy)phenyl)-4,5-bis(9-anthracenyl) fluorene, 9,9-bis(4-(2-hydroxyethoxy)phenyl)-4,5-bis(9-phenanthrene base) fluorine, 9,9-bis(4-(2-hydroxyethoxy)phenyl)-4,5-bis(1-pyrenyl) fluorine, 9,9-bis(4-(2-hydroxyethyl) Oxy)phenyl)-4, 5-bis(1-tolyl) terpene.

When the ring Z is naphthalene, 9,9-bis(6-hydroxy-2-naphthyl)-1,8-bis(9- Anthracenyl) stilbene, 9,9-bis(6-hydroxy-2-naphthyl)-1,8-bis(9-phenanthrenyl) stilbene, 9,9-bis(6-hydroxy-2-naphthyl)- 1,8-bis(1-pyrenyl) fluorene, 9,9-bis(6-hydroxy-2-naphthyl)-1,8-bis(1-tolyl) fluorine, 9,9-bis(6- Hydroxy-2-naphthyl)-2,7-bis(9-anthracenyl) fluorene, 9,9-bis(6-hydroxy-2-naphthyl)-2,7-bis(9-phenanthrenyl) fluorene, 9,9-bis(6-hydroxy-2-naphthyl)-2,7-bis(1-pyrenyl) fluorene, 9,9-bis(6-hydroxy-2-naphthyl)-2,7-bis (1-tolyl) fluorene, 9,9-bis(6-hydroxy-2-naphthyl)-3,6-bis(9-anthracenyl) fluorine, 9,9-bis(6-hydroxy-2-naphthalene Base)-3,6-bis(9-phenanthrenyl) fluorene, 9,9-bis(6-hydroxy-2-naphthyl)-3,6-bis(1-pyrenyl) fluorine, 9,9-bis (6-Hydroxy-2-naphthyl)-3,6-bis(1-tolyl) fluorene, 9,9-bis(6-hydroxy-2-naphthyl)-4,5-bis(9-anthracenyl) ) fennel, 9,9-bis(6-hydroxy-2-naphthyl)-4,5-bis(9-phenanthrenyl) fluorine, 9,9-bis(6-hydroxy-2-naphthyl)-4, 5-bis(1-pyrenyl) fluorene, 9,9-bis(6-hydroxy-2-naphthyl)-4,5-bis(1-tolyl) fluorine, 9,9-bis(6-(2 -Hydroxyethoxy)-2-naphthyl)-1,8-bis(9-anthracenyl)stilbene, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-1 ,8-bis(9-phenanthrenyl) fluorine, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-1,8-bis(1-pyrenyl) fluorine, 9, 9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-1,8-bis(1-tolyl) fluorene, 9,9-bis(6-(2-hydroxyethoxy) -2-naphthyl)-2,7-bis(9-anthracenyl)fluorene, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-bis(9 -phenanthrenyl) fluorine, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)phenyl)-2,7-bis(1-pyrenyl) fluorine, 9,9-bis (6-(2-Hydroxyethoxy)-2-naphthyl)-2,7-bis(1-tolyl)fluorene, 9,9-bis(6-(2-hydroxyethoxy)-2- Naphthyl)-3,6-bis(9-anthracenyl) stilbene, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-3,6-bis(9-phenanthrenyl) ) fennel, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-3,6-bis(1-pyrenyl) fennel, 9,9-bis(6-(2- Hydroxyethoxy)-2-naphthyl)-3,6-bis(1-tolyl)fluorene, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-4, 5-bis(9-anthracenyl) fluorine, 9 ,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-4,5-bis(9-phenanthrene) fluorene, 9,9-bis(6-(2-hydroxyethoxy) )-2-naphthyl)-4,5-bis(1-pyrenyl) fluorene, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-4,5-bis( 1-tolyl) terrene.

Among them, the following formula (a'-1) represented by the following formulas (a'-1)~(a'-8) is particularly preferred: 9,9-bis(4-hydroxyphenyl)-2,7- Bis(9-phenanthrenyl) fluorine, the following formula (a'-2): 9,9-bis(4-(2-hydroxyethoxy)phenyl)-2,7-bis(9-phenanthrenyl) Perylene, the following formula (a'-3): 9,9-bis(6-hydroxy-2-naphthyl)-2,7-bis(9-phenanthrenyl) fluorine, the following formula (a'-4) : 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-bis(9-phenanthrenyl) fluorine, the following formula (a'-5): 9,9 -bis(4-hydroxyphenyl)-2,7-bis(1-tolyl) fluorine, the following formula (a'-6): 9,9-bis(4-(2-hydroxyethoxy)benzene Base)-2,7-bis(1-tolyl) terpene, the following formula (a'-7): 9,9-bis(6-hydroxy-2-naphthyl)-2,7-bis(1- Tolyl) fluorine, the following formula (a'-8): 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-bis(1-tolyl) fluorine For another preference, the following formula (a'-1): 9,9-bis(4-hydroxyphenyl)-2,7-bis(9-phenanthrenyl) fluorine, the following formula (a'-2) : 9,9-bis(4-(2-hydroxyethoxy)phenyl)-2,7-bis(9-phenanthrene) fluorene, the following formula (a'-3): 9,9-bis( 6-Hydroxy-2-naphthyl)-2,7-bis(9-phenanthrene) fluorene, the following formula (a'-4): 9,9-bis(6-(2-hydroxyethoxy)- 2-naphthyl)-2,7-bis(9-phenanthrenyl) terpene is more preferred, with the following formula (a'-2): 9,9-bis(4-(2-hydroxyethoxy)phenyl )-2,7-bis(9-phenanthrenyl) fluorine, the following formula (a'-4): 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2, 7-bis(9-phenanthrene) fennel. These may be used alone or in combination of two or more.

The purity of the compound with the fennel skeleton of the present invention can be selected from a wide range of 60 to 100%, preferably more than 80%, more preferably more than 90%, more preferably more than 95%, and especially preferably 98%. %above. Purity was measured by HPLC.

The Hazen unit color number (APHA) of a 5% by weight solution of the compound having a fennel skeleton in the present invention dissolved in dimethylformamide is preferably 500 or less, and more preferably 100 or less, More preferably, it is 50 or less. When APHA is 500 or less, since the hue of the compound which has a terpene skeleton becomes favorable, it is preferable.

The compound having a fennel skeleton of the present invention has a refractive index of preferably not less than 1.70, more preferably not less than 1.72, more preferably not less than 1.74. The refractive index is measured as follows: a compound having a terpene skeleton is dissolved in dimethylsulfoxide to prepare a solution of a specified concentration, and the refractive index of the solution of each concentration is measured using a DR-M2 Abbe refractometer manufactured by ATAGO Corporation. The D-line refractive index at 25° C. was measured, and a value extrapolated from the measurement results of each concentration to a concentration of 100% was used as the refractive index (nD) of the obtained compound.

In the compound having a fennel skeleton of the present invention, the content of sulfur element is preferably less than 200 ppm, more preferably less than 100 ppm, more preferably less than 50 ppm, and most preferably less than 30 ppm. When the content of the elemental sulfur is 200 ppm or less, the hue of the compound having the fennel skeleton becomes favorable, which is preferable.

In the compound having a fennel skeleton of the present invention, the content of bromine element is preferably less than 150 ppm, more preferably less than 50 ppm, more preferably less than 20 ppm. When the content of the bromine element is 150 ppm or less, the hue of the compound having the fennel skeleton becomes favorable, which is preferable.

<Manufacturing method of a compound having a fennel skeleton> The production method of the compound having a fennel skeleton of the present invention is not particularly limited. For example, as described in Patent Document 5, it can be produced by the following steps: in the presence of an acid catalyst, fennel represented by the following formula (A) Ketones and the alcohols represented by the following formula (B) are reacted in a reaction solvent to obtain the step of the compound represented by the following formula (C); the compound represented by the following formula (C) and ethylene carbonate are reacted in response to Desirably, in the presence of a base, react in a reaction solvent to obtain a step of a compound represented by the following formula (D); in the presence of a base and a palladium-based catalyst, the compound represented by the following formula (D) A step of obtaining a compound represented by the aforementioned formula (a) by reacting with boric acids represented by the following formula (E) in a reaction solvent.

(式中，X1係1位、2位、3位或4位的取代基，表示鹵素原子，X ²係5位、6位、7位或8位的取代基，表示鹵素原子)。

(wherein, X1 is a substituent at position 1, 2, 3 or 4, representing a halogen atom, and X2 is a substituent at position ⁵ , 6, 7 or 8, representing a halogen atom).

(式中，環Y表示芳香族烴環，R ³表示氫原子、鹵素原子、可包含芳香族基的碳原子數1~20的取代基，o為1以上的整數)。

(In the formula, ring Y represents an aromatic hydrocarbon ring, ^R represents a hydrogen atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, and o is an integer of 1 or more).

(式中，環Z係相同或相異地表示芳香族烴環，R ¹及R ²分別獨立表示氫原子、鹵素原子、可包含芳香族基的碳原子數1~20的取代基，j及k分別獨立表示1以上的整數，X ¹及X ²為鹵素原子)。

(In the formula, ring Z represents an aromatic hydrocarbon ring identically or differently, R1 and R2 independently represent ^{a hydrogen} atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, j and k each independently represents an integer of ¹ or more, and X1 and X2 are halogen atoms ⁾ .

(式中，環Z係相同或相異地表示芳香族烴環，R ¹及R ²分別獨立表示氫原子、鹵素原子、可包含芳香族基的碳原子數1~20的取代基，X ¹及X ²為鹵素原子，L ¹及L ²分別獨立表示2價的連結基，j及k分別獨立表示1以上的整數，m及n分別獨立為0或1)。

(In the formula, ring Z represents an aromatic hydrocarbon ring identically or differently, R ¹ and R ² independently represent a hydrogen atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, X ¹ and R 2 X ² is a halogen atom, L ¹ and L ² each independently represent a divalent linking group, j and k each independently represent an integer of 1 or more, m and n each independently represent 0 or 1).

(式中，Ar ³係3個以上的苯環經縮環而成的多環芳香族烴基)。

(In the formula, Ar ³ is a polycyclic aromatic hydrocarbon group formed by condensing 3 or more benzene rings).

(式中，環Z係相同或相異地表示芳香族烴環，R ¹及R ²分別獨立表示氫原子、鹵素原子、可包含芳香族基的碳原子數1~20的取代基，Ar ¹及Ar ²係3個以上的苯環經縮環而成的多環芳香族烴基，L ¹及L ²分別獨立表示2價的連結基，j及k分別獨立表示1以上的整數，m及n分別獨立為0或1)。

(In the formula, ring Z represents an aromatic hydrocarbon ring identically or differently, R ¹ and R ² independently represent a hydrogen atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, Ar ¹ and R 2 Ar ² is a polycyclic aromatic hydrocarbon group formed by condensing 3 or more benzene rings, L ¹ and L ² independently represent a divalent linking group, j and k independently represent an integer of 1 or more, m and n respectively independently 0 or 1).

The detailed description of the above-mentioned fennelones, alcohols, reaction solvent, acid catalyst, and base or the detailed production method until the above-mentioned formula (D) is obtained is as described in Patent Document 5.

The boric acids used in the present invention are preferably anthraceneboronic acid, phenanthreneboronic acid, pyreneboronic acid, and pyreneboronic acid, more preferably phenanthreneboronic acid, and particularly preferably 9-phenanthreneboronic acid. In addition, boric acid esters or boric anhydrides of these compounds are also included as boric acids. These boric acids may be used alone or in combination of two or more, and may be arbitrarily selected according to the purpose.

Relative to 1 mole of the compound represented by the aforementioned formula (D), the use ratio of boric acids used in the present invention is preferably 1.5-3.0 moles, more preferably 2.0-2.5 moles, and 2.0-2.0 moles. 2.3 moles is especially preferred.

(the carbonate component of the aforementioned formula (1)) As the carbonate component of the unit represented by the said formula (1) used for the thermoplastic resin of this invention, phosgene and carbonate are mentioned. Carbonic acid esters include esters such as an aryl group having 6 to 10 carbon atoms, an aralkyl group, or an alkyl group having 1 to 4 carbon atoms which may be substituted. Specifically, diaryl carbonate such as diphenyl carbonate, xylyl carbonate, bis(chlorophenyl) carbonate, bis(m-tolyl) carbonate, dinaphthyl carbonate, dimethyl carbonate, etc. esters, diethyl carbonate, dibutyl carbonate, dialkyl carbonate such as dicyclohexyl carbonate, ethylphenyl carbonate, alkylaryl carbonate such as cyclohexylphenyl carbonate, or divinyl carbonate, carbonic acid Diisopropenyl carbonate, dienyl carbonate such as dipropylene carbonate, etc., among them, diaryl carbonate is preferable, and diphenyl carbonate is more preferable.

(dicarboxylic acid component of the aforementioned formula (1)) As the dicarboxylic acid component represented by the unit represented by the formula (1) used in the thermoplastic resin of the present invention, it is mainly preferred to use a dicarboxylic acid represented by the formula (b) or an ester-forming derivative thereof.

In the aforementioned formula (b), X represents a divalent linking group, and can be said to be the same as that described in the aforementioned formula (3).

The following are representative specific examples of the dicarboxylic acid represented by the formula (b) or its ester-forming derivative, but the raw materials used for the formula (b) of the present invention are not limited thereto.

As the dicarboxylic acid component used in the thermoplastic resin of the present invention, in addition to 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl, 6,6 '-Diphenyl-2,2'-bis(carboxymethoxy)-1,1'-binaphthyl, 6,6'-dibromo-2,2'-bis(carboxymethoxy)-1, In addition to 1'-binaphthyl, 9,9-bis(2-carboxyethyl) fluorene, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, Aliphatic dicarboxylic acid components such as diacid, methylmalonic acid, ethylmalonic acid, etc., monocyclic aromatic dicarboxylic acid components such as phthalic acid, isophthalic acid, and terephthalic acid, 2 ,6-naphthalene dicarboxylic acid, 2,7-naphthalene dicarboxylic acid, 2,3-naphthalene dicarboxylic acid, 1,4-naphthalene dicarboxylic acid, 1,8-naphthalene dicarboxylic acid, anthracene dicarboxylic acid, phenanthrene Dicarboxylic acid, 9,9-bis(carboxymethyl) fluorine, 9,9-bis(1-carboxyethyl) fluorine, 9,9-bis(1-carboxypropyl) fluorine, 9,9-bis( 2-carboxypropyl) fluorene, 9,9-bis(2-carboxy-1-methylethyl) fluorene, 9,9-bis(2-carboxy-1-methylpropyl) fluorene, 9,9- Bis(2-carboxybutyl) terrene, 9,9-bis(2-carboxy-1-methylbutyl) terrene, 9,9-bis(5-carboxypentyl) terrene, 9,9-bis(carboxy Polycyclic aromatic dicarboxylic acid components such as cyclohexyl) fennel, biphenyl dicarboxylic acid components such as 2,2'-biphenyl dicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 2,6- Alicyclic dicarboxylic acid components such as decahydronaphthalene dicarboxylic acid, such as isophthalic acid, terephthalic acid, 2,6-naphthalene dicarboxylic acid, 2,2'-bis(carboxymethoxy)-1 , 1'-binaphthalene, 9,9-bis(2-carboxyethyl) stilbene are preferred, 2,6-naphthalene dicarboxylic acid, 2,2'-bis(carboxymethoxy)-1,1 '-Binaphthyl and 9,9-bis(2-carboxyethyl) terrene are further preferred. These can be used alone or in combination of two or more kinds. Also, as the ester-forming derivatives, esters such as acid chlorides, methyl esters, ethyl esters, and phenyl esters can be used.

(the components of the aforementioned formulas (7) to (10)) The thermoplastic resin of this invention may further have the repeating unit of said formula (7)-(10), and the dihydroxy compound component used as a raw material of said formula (7)-(10) is shown below. These may be used alone or in combination of two or more.

The dihydroxy compound component used as the raw material of the aforementioned formula (7) of the present invention includes 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene, 2,2'-bis( 2-Hydroxyethoxy)-3,3'-diphenyl-1,1'-binaphthyl, 2,2'-bis(2-hydroxyethoxy)-6,6'-diphenyl-1 ,1'-binaphthyl, 2,2'-bis(2-hydroxyethoxy)-7,7'-diphenyl-1,1'-binaphthyl, 2,2'-bis(2-hydroxyethyl Oxy)-3,3'-dimethyl-1,1'-binaphthyl, 2,2'-bis(2-hydroxyethoxy)-6,6'-dimethyl-1,1'- Binaphthyl, 2,2'-bis(2-hydroxyethoxy)-7,7'-dimethyl-1,1'-binaphthyl.

The dihydroxy compound component that becomes the raw material of the aforementioned formula (8) of the present invention can be exemplified by 9,9-bis(4-(2-hydroxyethoxy) phenyl) fluorene, 9,9-bis(4-(2 -Hydroxyethoxy)-3-methylphenyl) fluorine, 9,9-bis(4-(2-hydroxyethoxy)-3-cyclohexylphenyl) fluorine, 9,9-bis(4- (2-Hydroxyethoxy)-3-phenylphenyl) fluorine, etc., 9,9-bis (4-(2-hydroxyethoxy) phenyl) fluorine, 9,9-bis (4-( 2-Hydroxyethoxy)-3-phenylphenyl) terpine is particularly preferred. These may be used alone or in combination of two or more.

The dihydroxy compound component that becomes the raw material of the aforementioned formula (9) of the present invention includes 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl) fluorene, 9,9-bis( 6-(2-Hydroxyethoxy)-2-naphthyl)-2,7-diphenylferene.

The dihydroxy compound component used as the raw material of the aforementioned formula (10) of the present invention can be exemplified by 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl) Propane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene, 1,1-bis( 4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(4-hydroxyphenyl)cyclohexane, bis(4-hydroxyphenyl)diphenylmethane, 1 ,1-bis(4-hydroxyphenyl)decane, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxy-3-methylphenyl)sulfide, biphenyl, 9,9-bis( 4-Hydroxyphenyl) fluorine, 9,9-bis(4-hydroxy-3-methylphenyl) fluorine, 9,9-bis(4-hydroxy-3-cyclohexylphenyl) Bis(4-hydroxy-3-phenylphenyl) terpene, bis(4-hydroxyphenyl)pyridine, 10,10-bis(4-hydroxyphenyl)anthrone, etc., with 2,2-bis(4- Hydroxyphenyl)propane and bis(4-hydroxyphenyl)sulfide are particularly preferred. These may be used alone or in combination of two or more.

Among the formulas (7)~(10), if it is 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene, 9,9-bis(4-(2-hydroxyethoxy Base) phenyl) fluorine, 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl) fluorine, 9,9-bis(6-(2-hydroxyethoxy)- 2-naphthyl) stilbene, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-diphenyl stilbene, due to the high refractive index and high heat resistance , Low birefringence balance, so it is particularly good.

It can be produced by, for example, a method of reacting a dihydroxy compound component with a carbonate precursor such as phosgene or a carbonic acid diester, or a method of reacting a diol component with a dicarboxylic acid or an ester-forming derivative thereof. The thermoplastic resin of the present invention. The specific example is shown below.

＜Manufacturing method＞ (Manufacturing method of polycarbonate resin) If the thermoplastic resin of the present invention is a polycarbonate resin, it can be obtained by a well-known reaction method, such as reacting a dihydroxy compound component and a carbonate precursor by interfacial polymerization or melt polymerization. When producing polycarbonate resin, catalysts, terminal stoppers, antioxidants, etc. can be used as needed.

(Manufacturing method of polyester resin) When the thermoplastic resin of the present invention is a polyester resin, it can be subjected to an esterification reaction or transesterification reaction between a dihydroxy compound component and a dicarboxylic acid or an ester-forming derivative thereof by a known reaction method per se, and The obtained reaction product may be subjected to polycondensation reaction to obtain a high molecular weight body having a desired molecular weight.

(Manufacturing method of polyester carbonate resin) When the thermoplastic resin of the present invention is a polyester carbonate resin, it can be obtained by reacting a dihydroxy compound component and a dicarboxylic acid or an ester-forming derivative thereof with a carbonate precursor such as phosgene or carbonate. to manufacture. As the polymerization method, the same method as that of the aforementioned polycarbonate resin or polyester resin can be used.

＜Optical components＞ The optical member of the present invention contains the above-mentioned thermoplastic resin. Such an optical member is not particularly limited as long as it is useful for the optical application of the above-mentioned thermoplastic resin, and examples thereof include optical lenses, optical discs, transparent conductive substrates, optical cards, sheets, films, optical fibers, etc. , lens, 稜鏡, optical film, substrate, optical filter, hard coating, etc.

In addition, the optical member of the present invention can be composed of a resin composition containing the above-mentioned thermoplastic resin, and in this resin composition, a heat stabilizer, a plasticizer, a light stabilizer, a polymeric metal inertizer, Additives for flame retardants, lubricants, antistatic agents, surfactants, antibacterial agents, ultraviolet absorbers, mold release agents, etc.

＜Optical lens＞ As an optical member of this invention, an optical lens is mentioned especially. Examples of such optical lenses include optical lenses used in mobile phones, smart phones, tablet terminals, personal computers, digital cameras, video cameras, vehicle cameras, surveillance cameras, and the like.

The optical lens of the present invention can be formed and processed by any method such as injection molding, compression molding, injection compression molding, melt extrusion molding, casting, etc., but injection molding is particularly suitable.

The molding conditions of injection molding are not particularly limited, but the cylinder temperature of the molding machine is preferably 180-320°C, more preferably 220-300°C, and most preferably 240-280°C. Also, the mold temperature is preferably 70-130°C, more preferably 80-125°C, and particularly preferably 90-120°C. The injection pressure is preferably 5~170MPa, more preferably 50~160MPa, and especially preferably 100~150MPa.

The present invention will be described more specifically based on the following examples, but the present invention is not limited thereto. [Example]

[Example 1] 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-two (9-phenanthrenyl) fluorine's synthesis 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-dibromo was synthesized by the method described in Example II-1 of International Publication No. 2020/226126 Bilberry (hereinafter sometimes abbreviated as BNDB).

In a flask equipped with a stirrer, a cooler, and a thermometer, add BNDB35.50g (0.05 mol), 9-phenanthrene boric acid 24.90g (0.11 mol), tetrakis (triphenylphosphine) palladium 0.59g (0.51mmol) ears), 62ml of 2M potassium carbonate aqueous solution, 232ml of toluene, and 76ml of ethanol, and stirred at 80°C for 3 hours. The progress of the reaction was confirmed by HPLC, and the remaining amount of BNDB was confirmed to be 0.0%, and the reaction was terminated. After adding 100 ml of ethyl acetate to the reaction liquid and diluting, it moved to a separatory funnel and washed with distilled water until it became neutral. The washed organic layer was treated with activated carbon, concentrated by an evaporator, and recrystallized. The resulting crystals were recovered and dried under reduced pressure for 12 hours to obtain 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7- A crystal of bis(9-phenanthrene) fennel (hereinafter sometimes abbreviated as BNDPh9). Also, the refractive index of BNDPh9 is 1.745.

[Example 2] Add 13.40 parts by mass (20mol%) of 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-bis(9-phenanthrenyl) fluorine ( hereinafter sometimes referred to as BNDPh9), 26.31 mass parts (80mol%) of 9,9-bis[4-(2-hydroxyethoxy)phenyl] fennel (hereinafter sometimes referred to as BPEF), 16.23 mass parts (101mol%) %) of diphenyl carbonate (hereinafter sometimes abbreviated as DPC), and 6.30×10 ^-5 parts by mass (1.00×10 ^-3 mol%) of sodium bicarbonate at a concentration of 40mmol/L as a catalyst, in nitrogen Heat to 180°C at ambient to melt. Thereafter, the degree of reduced pressure was adjusted to 20 kPa over 5 minutes. Heat up to 250°C at a heating rate of 60°C/hr. After the outflow of phenol reaches 70%, depressurize at 60kPa/hr, and carry out polymerization reaction until the specified power is reached. Remove the resin. The obtained polycarbonate resin was analyzed by ¹ H NMR, and it was confirmed that 20 mol% of the BNDPh9 component was introduced with respect to the total monomer components, and 80 mol% of the BPEF component was introduced with respect to the total monomer components. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polycarbonate resin, and the results are shown in Table 1.

[Example 3~5] A polycarbonate resin was produced in the same manner as in Example 2 except that the ratio of BNDPh9 and BPEF was changed. Table 2 shows the results of evaluating the copolymerization ratio, refractive index, Abbe number, Tg, and Δn using this polycarbonate resin.

[Comparative example 1] Except using 9,9-bis(4-(2-hydroxyethoxy)phenyl)-2,7-diphenylfen (hereinafter "BPDP2") instead of BNDPh9, adopt the same method as in Example 1 to Manufactures polycarbonate resins. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polycarbonate resin, and the results are shown in Table 1. Also, BPDP2 has the following chemical structure.

[Comparative example 2] In addition to using 9,9-bis(4-(2-hydroxyethoxy)phenyl)-2,7-bis(2-naphthyl) fluorene (hereinafter "BPDN2") to replace BNDPh9, the method used in Example 1 Polycarbonate resin was produced in the same manner. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polycarbonate resin, and the results are shown in Table 1. Also, BPDN2 has the following chemical structure.

[Comparative example 3] Except using 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-diphenylfen (hereinafter "BNDP2") instead of BNDPh9, the same method as in Example 1 way to produce polycarbonate resin. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polycarbonate resin, and the results are shown in Table 1. Also, BNDP2 has the following chemical structure.

[Comparative example 4] In addition to using 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-bis(2-naphthyl) fluorene (hereinafter "BNDN2") instead of BNDPh9, the same Polycarbonate resin was produced in the same manner as in Example 1. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polycarbonate resin, and the results are shown in Table 1. Also, BNDN2 has the following chemical structure.

[Example 6] In addition to changing BNDPh9, 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (hereinafter sometimes abbreviated as BHEB), 2,2'-bis(carboxymethoxy base)-1,1'-binaphthyl (hereinafter sometimes abbreviated as BCMB), changing DPC to 1.64 parts by mass (10.2 mol%), and using 1.3×10 ^-2 parts by mass (5.0×10 ^-2 mol%) of titanium tetrabutoxide (titanium tetrabutoxide), the polyester carbonate resin was produced in the same manner as in Example 1. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polyester carbonate resin, and the results are shown in Table 1.

[Examples 7 and 8] A polyester carbonate resin was produced in the same manner as in Example 5 except that the ratios of BNDPh9, BHEB, and BCMB were changed. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polyester carbonate resin, and the results are shown in Table 1.

[Comparative Example 5] A polyester carbonate resin was produced in the same manner as in Example 2 except that BPDP2 was used instead of BNDPh9. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polyester carbonate resin, and the results are shown in Table 1.

[Comparative Example 6] A polyester carbonate resin was produced in the same manner as in Example 2 except that BPDN2 was used instead of BNDPh9. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polyester carbonate resin, and the results are shown in Table 1.

[Comparative Example 7] A polyester carbonate resin was produced in the same manner as in Example 2 except that BNDP2 was used instead of BNDPh9. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polyester carbonate resin, and the results are shown in Table 1.

[Comparative Example 8] A polyester carbonate resin was produced in the same manner as in Example 2 except that BNDN2 was used instead of BNDPh9. The copolymerization ratio, refractive index, Abbe's number, Tg, and Δn were evaluated using this polyester carbonate resin, and the results are shown in Table 1.

The obtained compound having a fennel skeleton and the thermoplastic resin were evaluated according to the following method.

<Compound having a fennel skeleton> (NMR) JNM-ECZ400S manufactured by JEOL Ltd. was used for measurement. The solvent is CDCl ₃ .

(High performance liquid chromatography (HPLC) measurement) Using high performance liquid chromatography L-2350 manufactured by Hitachi, the measurement was performed under the measurement conditions in Table 1 below. Unless otherwise specified in the examples, % means the area percentage value after removing the solvent in the HPLC and correcting it.

(refractive index) The measurement sample was dissolved in dimethyl oxide to prepare a solution of a predetermined concentration, and the refractive index of the solution of each concentration was measured at 25° C. using a DR-M2 Abbe refractometer manufactured by ATAGO Corporation. The value extrapolated to 100% of the concentration obtained from the measurement results of each concentration was used as the refractive index (nD) of the compound obtained in the examples.

<Thermoplastic resin><Copolymerizationratio> The obtained resin was measured by ¹ H NMR using JNM-ECZ400S manufactured by JEOL Ltd., and the composition ratio of each polymer was computed. The solvent is CDCl ₃ .

＜Optical properties＞ (refractive index) A test piece having a thickness of 3 mm of each polymer was prepared and ground, and then the refractive index nd (587.56 nm) at 20° C. was measured using a KALNEW precision refractometer KPR-2000 manufactured by Shimadzu Corporation.

(Abbe number) Abbe's number was calculated by measuring the refractive index at wavelengths of 486.13 nm, 587.56 nm, and 656.27 nm and using the following formula. νd=(nd-1)/(nF-nC) nd: Represents the refractive index at a wavelength of 587.56nm, nF: Represents the refractive index at a wavelength of 486.13nm, nC: Represents the refractive index at a wavelength of 656.27 nm.

(absolute value of alignment birefringence) The thermoplastic resin was dissolved in dichloromethane, cast on a glass dish, and dried sufficiently to produce a cast film with a thickness of 100 μm. The film was stretched twice at Tg+10°C, and the phase difference (Re) at 589nm was measured using the JASCO Co., Ltd. ellipsometer M-220, and the absolute value of the alignment birefringence was obtained according to the following formula (|Δn|). |Δn|=|Re/d| Δn: alignment birefringence Re: phase difference (nm) d: thickness (nm)

＜Glass transition temperature (Tg)＞ The obtained resin was measured with the Discovery DSC25Auto type manufactured by TI INSTRUMENTS JAPAN Co., Ltd. at a heating rate of 20° C./min. Samples are measured at 5-10 mg.

≪Results≫ Table 2 shows the evaluation results of specific examples of thermoplastic resins. Also, the ¹ H-NMR spectrum of BNDPh9 in Example 1 is shown in FIG. 1 , and the ¹ H-NMR spectra of the thermoplastic resins in Examples 2 and 4 are shown in FIGS. 2 to 3 .

It can be seen that Examples 2 to 8 using BNDPh9 have a high refractive index, and can balance heat resistance and birefringence, so excellent results are obtained as optical lenses.

Compared with Examples 2 to 5, the increase in birefringence was improved due to the introduction of aromatic groups in Comparative Examples 1 to 4. Compared with Examples 6-8, Comparative Examples 5-8 are a trade-off between refractive index and birefringence.

Like the repeating unit of formula (1), the fennel skeleton has a structure obtained by condensing three or more benzene rings, so that the increase in polarizability and the expansion of conjugation can be achieved at a high degree, and high refractive index can be achieved. High efficiency, high heat resistance, and low birefringence are effectively balanced. [ Industrial Utilization]

The thermoplastic resin of the present invention is suitable for use in optical materials, specifically optical lenses, optical discs, transparent conductive substrates, optical cards, sheets, films, optical fibers, optical films, optical filters, hard coats, etc. Optical members such as films are particularly useful for optical lenses.

[ Fig. 1 ] ¹ H NMR of 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-bis(9-phenanthrenyl) terpene obtained in Example 1. [ Fig. 2 ] ¹ H NMR of the polycarbonate resin obtained in Example 2. [ Fig. 3 ] ¹ H NMR of the polyester carbonate resin obtained in Example 6.

Claims (25)

A thermoplastic resin comprising repeating units represented by the following formula (1),

(In the formula, the ring Z system (same or different) represents an aromatic hydrocarbon ring, R1 and R2 independently represent ^{a hydrogen} atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, and Ar ¹ and Ar ² are each independently a polycyclic aromatic hydrocarbon group formed by condensing 3 or more benzene rings, L ¹ and L ² each independently represent a divalent linking group, j and k each independently represent an integer of 1 or more, m and n independently represent 0 or 1, and W is at least one selected from the group represented by the following formula (2) and the following formula (3))

(In the formula, X represents a divalent linking group). The thermoplastic resin according to claim 1, wherein the aforementioned formula (1) is at least one selected from the group consisting of units represented by the following formulas (1a) to (1d),

(In the formula, the ring Z system (same or different) represents an aromatic hydrocarbon ring, R1 and R2 independently represent ^{a hydrogen} atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, and Ar ¹ and Ar ² are respectively independently polycyclic aromatic hydrocarbons formed by condensing 3 or more benzene rings, L ¹ and L ² independently represent a divalent linking group, j and k independently represent an integer of 1 or more, m and n each independently represent 0 or 1, and W is at least one selected from the group represented by the aforementioned formula (2) and the aforementioned formula (3). The thermoplastic resin according to claim 2, wherein the aforementioned formula (1) is the aforementioned formula (1b). The thermoplastic resin according to any one of claims 1 to 3, wherein Ar ¹ and Ar ² in the aforementioned formula (1) are polycyclic aromatic hydrocarbons of the phenanthrene type. The thermoplastic resin according to any one of claims 1 to 4, wherein, in the aforementioned formula (1), Ar ¹ and Ar ² are polycyclic aromatic hydrocarbons formed by condensing 3 or 4 benzene rings . The thermoplastic resin according to any one of claims 1 to 5, wherein, in the aforementioned formula (1), Ar ¹ and Ar ² are phenanthrene. The thermoplastic resin according to any one of claims 1 to 6, wherein the repeating unit represented by the aforementioned formula (1) is represented by the following formula (4),

(In the formula, the ring Z system (same or different) represents an aromatic hydrocarbon ring, R1 and R2 independently represent ^{a hydrogen} atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, and L ¹ and L2 each independently represent a divalent linking group, j and ^k each independently represent an integer greater than 1, m and n each independently represent 0 or 1, W is selected from the aforementioned formula (2) and the aforementioned formula (3) at least one of the groups indicated). The thermoplastic resin according to any one of claims 1 to 7, wherein the repeating unit represented by the aforementioned formula (1) is represented by the following formula (5),

(wherein, L ¹ and L ² independently represent a divalent linking group, m and n independently represent 0 or 1, W is at least one of the groups represented by the aforementioned formula (2) and the aforementioned formula (3) one). The thermoplastic resin according to any one of claims 1 to 8, wherein X in the aforementioned formula (3) includes at least one selected from the group consisting of phenylene, naphthalenediyl, and groups represented by the following formula (6) as a repeating unit,

(In the ^formula , ^R3 and R4 are each independently a hydrogen atom, a substituent having 1 to 20 carbon atoms that may contain an aromatic group, or a halogen atom). The thermoplastic resin according to any one of claims 1 to 9, wherein, in addition to the repeating unit represented by formula (1), it further comprises a unit selected from the units represented by the following formulas (7) to (10) at least one of the groups as the repeating unit,

(In the ^formula , ^R5 and R6 are independently a hydrogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, or a halogen atom)

(In the formula, R ⁷ and R ⁸ are each independently a hydrogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, or a halogen atom)

(In the formula, R ⁹ and R ¹⁰ are independently a hydrogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, or a halogen atom)

(In the formula, R ¹¹ and R ¹² are each independently a hydrogen atom, a substituent with 1 to 20 carbon atoms that may include an aromatic group, or a halogen atom, and U is a single bond or a divalent linking group). The thermoplastic resin according to any one of claims 1 to 10, wherein the refractive index is 1.650 to 1.800. The thermoplastic resin according to any one of claims 1 to 11, wherein the specific viscosity is 0.12 to 0.40. The thermoplastic resin according to any one of claims 1-12, wherein the glass transition temperature is 130-190°C. The thermoplastic resin according to any one of claims 1 to 13, wherein the alignment birefringence is 5.0×10 ^-3 or less. An optical component made of the thermoplastic resin according to any one of claims 1-14. The optical member as claimed in claim 15 is an optical lens. A compound having a fennel skeleton represented by the following formula (a),

(In the formula, ring Z represents an aromatic hydrocarbon ring identically or differently, R ¹ and R ² independently represent a hydrogen atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, Ar ¹ and R 2 Ar ² is a polycyclic aromatic hydrocarbon group formed by condensing 3 or more benzene rings, L ¹ and L ² independently represent a divalent linking group, j and k independently represent an integer of 1 or more, m and n respectively independently 0 or 1). A compound having a fennel skeleton as claimed in item 17, wherein the aforementioned formula (a) is at least one selected from the group consisting of compounds represented by the following formulas (aI) to (a-IV),

(In the formula, ring Z represents an aromatic hydrocarbon ring identically or differently, R ¹ and R ² independently represent a hydrogen atom, a halogen atom, a substituent with 1 to 20 carbon atoms that may contain an aromatic group, Ar ¹ and R 2 Ar ² is a polycyclic aromatic hydrocarbon formed by condensing 3 or more benzene rings, L ¹ and L ² independently represent a divalent linking group, j and k independently represent an integer of 1 or more, m and n respectively independently 0 or 1). The compound having a fennel skeleton as claimed in item 18, wherein the aforementioned formula (a) is the aforementioned formula (a-II). A compound having a fennel skeleton as claimed in any one of items 17 to 19, wherein Ar ¹ and Ar ² in the aforementioned formula (a) are polycyclic aromatic hydrocarbons of the phenanthrene type. A compound having a fennel skeleton as claimed in any one of items 17 to 20, wherein, in the aforementioned formula (a), Ar ¹ and Ar ² are polycyclic aromatic compounds formed by condensing 3 or 4 benzene rings. A group of hydrocarbons. The compound having a fennel skeleton as claimed in any one of items 17 to 21, wherein, in the aforementioned formula (a), Ar ¹ and Ar ² are phenanthrene. A compound having a fennel skeleton as claimed in any one of items 17 to 22, wherein the aforementioned formula (a) is represented by the following formula (b),

(In the formula, ring Z represents an aromatic hydrocarbon ring identically or differently, R1 and R2 independently represent ^{a hydrogen} atom, a halogen atom, a substituent with ¹ to 20 carbon atoms that may contain an aromatic group, L1 and L ² each independently represent a divalent linking group, j and k each independently represent an integer of 1 or more, m and n each independently represent 0 or 1). A compound having a fennel skeleton as claimed in any one of items 17 to 23, wherein the aforementioned formula (a) is represented by the following formula (c),

(In the formula, L ¹ and L ² each independently represent a divalent linking group, and m and n are each independently 0 or 1). The compound having a fennel skeleton according to any one of claims 17 to 24, wherein the refractive index is 1.70 or more.

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